BOSSTORQUE × Sperry Tree Care · Prepared March 23, 2026 · Meeting: Wednesday, March 25

Full Project
Roadmap

Every initiative identified since July 2025. Strategic fee structure. 9-month execution plan.
The AI window is open now. The firms that move first lock in the advantage.
Total Initiatives
49
Projects Delivered / Active
13+
Club Members
988
Campaign Conversion
10.15%
Current Margin
8.5%
Target Margin
20–25%
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Executive Summary

This document maps the full 9-month engagement for Sperry Tree Care — April through December 2026. It covers where your business stands today, what BOSSTORQUE is proposing to build, what it costs, and how the partnership model works. It was prepared in one day ahead of Wednesday's meeting. All project estimates beyond the Q2 SOW are initial figures — each requires a scoping session and written approval before work begins.

The foundation is proven. Eight months of work produced 988 Club members at 10.15% conversion, 48.7% open rates, and a retention flywheel you described as the most successful demand generation effort in Sperry's history. This roadmap extends that foundation across 49 sequenced projects — AI phone system, website, paid acquisition, operational tooling, and subscription programs — building on each other across three quarters toward a 20–25% contribution margin target.

The known advisory investment is $57K–$65K over 9 months, with a performance component that activates only when Sperry's contribution margin grows above today's baseline — $0 if results are flat, ~$37.5K at moderate growth. Wednesday's agenda covers the Q2 SOW ready for signature, the full partnership model and its terms, and whatever questions you need answered before moving forward.

Where We Are · March 23, 2026
Campaign Scorecard
B1–B12 deployment complete. B12 sequence ends ~March 27. Final member count in March 30 report. Technical terms are defined on first use throughout this document. Full glossary at the end.
9,730
Contacts deployed · All 12 batches · 99.8% of validated list
988
Club members confirmed in Kit · ~999 Jobber-tagged
10.15%
Overall conversion · Industry avg 1–3%
48.7%
Open rate · Industry avg 22–29%
88.2%
Welcome email open rate · Post-join confirmation
307
SMS opt-ins reconciled · Not yet activated
Batch Performance Summary · B1–B12
B5 Sweet Spot Conversion
27.9%
$7,102 avg LTV · Meta lookalike seed list
B12 Status
Day 6 of 10
Final count ~Mar 27
SMS Opt-In Rate
31.1%
2× industry avg · TCR registration pending
Total Campaign Cost
$8,346
20x–106x projected revenue ROI
Bounce Rate
0.66%
Target <2% ✓
Revenue Projection
$876K–$1.38M
3 scenarios · 988 members · see margin model
What 988 Members Are Worth — Revenue & Profit Impact
ScenarioAssumptionProjected Revenue InfluenceAt 8.5% Margin (Today)At 15% Margin (Target)At 20% Margin (Goal)
Conservative 20% of members book 1 job · $850 avg $167,960 $14,277 $25,194 $33,592
Moderate 35% of members book 1 job · $1,200 avg $415,170 $35,289 $62,276 $83,034
Optimistic 50% of members book avg $1,800 · some multi-job $888,300 $75,506 $133,245 $177,660

Revenue influence = projected bookings from Club members over a 12-month period. Profit shown at three margin levels — current (8.5%), working assumption (15%), and strategic target (20%). These projections apply to the existing 988-member base only and do not include new members, Meta leads, SMS campaigns, or any other revenue stream in this roadmap. All figures are estimates based on Sperry's average job value and B5 Sweet Spot conversion data. Actual results depend on campaign execution, seasonality, and member response rates.

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Why Now Matters More Than Ever
The AI Acceleration Window
This isn't a reason to rush carelessly. It's a reason to execute deliberately — and not wait.

The window for first-mover advantage in trades AI is open right now. It won't stay open indefinitely.

Capabilities that used to take 3–5 years to build — automated lead nurturing, AI phone handling, data-driven customer segmentation, paid social at scale, subscription program infrastructure — are now deployable in weeks. The cost of entry has collapsed. The tools exist. The question is who moves first.

In Lane County tree care, the answer is currently: nobody has moved. Sperry is positioned to be the first established firm in this market to deploy a full AI-enabled revenue engine — Club flywheel, Quo AI receptionist, automated nurture sequences, predictive segmentation, and data-backed paid acquisition. That is a durable competitive advantage, not a temporary one. The customer relationships, the data, and the brand recognition that come from moving first compound over time.

Waiting is not neutral.

Every month of delay on the remaining 35 projects is a month a faster-moving competitor isn't standing still either. Regional consolidators, private equity-backed tree care chains, and tech-forward independents are all deploying these tools. Sperry's 35-year reputation and 10,800-contact database are the most defensible assets in this market — but only if they're activated before the competitive landscape shifts.

Sperry's foundation is already built.

The list is warm. 988 members are enrolled and engaged. The automation infrastructure is live. Every project from here builds on a proven platform — not from scratch. That means Sperry can move faster and cheaper than any competitor starting today. The advantage compounds with every week of execution. The risk of inaction grows with every week of delay.

AI specifically changes three things for tree care businesses — and all three favor moving now.

1. Customer acquisition cost drops dramatically. AI-driven segmentation, retargeting (ads shown to people who've already visited your site), and lookalike audiences (finding new prospects who match your best customers) mean paid ads get more efficient with every campaign cycle. Competitors who start building those data assets later will always be paying more per lead than Sperry.

2. Phone and scheduling leakage becomes eliminable. Quo's Sona AI handles after-hours calls, logs every interaction in Jobber, and routes immediately. The estimate revenue lost to unanswered phones — currently a documented leak in Sperry's business — disappears. Competitors without this lose jobs every day they don't have it.

3. Subscription programs become operationally manageable. The scheduling complexity of recurring care plan visits — the main reason most small tree care operators don't offer them — is now solvable with AI-assisted dispatching and automated customer communication. The firms that build subscription bases now will have the recurring revenue floor that makes them recession-resilient and acquisition-ready. The firms that don't will remain dependent on storm seasons and one-time removal demand.

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Section 01 · Strategic Context
The Margin Opportunity
Revenue growth is the headline. Margin improvement is where the wealth is built. Both are primary goals of this engagement.

Sperry is leaving $345,000/year in profit on the table.

At 8.5% net margin on $3M revenue, Sperry earns $255,000/year in profit. Well-run tree care companies with Sperry's tenure and ISA credentials achieve 20%+ net margin — that's $600,000/year. The gap is $345,000. Every 1% of margin improvement at current revenue is $30,000 in additional annual profit.

⚠ Margin improvement is a primary goal — and it will be significant.

Every project on this roadmap — recurring Club revenue, annual contracts, PHC (Plant Health Care — scheduled fertilization, soil treatment, pest and disease management) programs, smarter pricing, demand smoothing, reduced friction — improves margin as well as revenue. We are explicitly targeting a meaningful improvement from 8.5% toward industry best practice. We will track it, measure it, and factor it into every recommendation. All projections in this deck show profit at 15% margin as a working assumption. Our strategic target is 20–25%.

Margin BenchmarkIndustry RatingAnnual Profit at $3MIncremental vs TodayValue of Each 1% Gained
8.5% (Sperry today)Below Good$255,000$30,000
10%Good$300,000+$45,000/yr$30,000
15%Very Good$450,000+$195,000/yr$30,000
20%Outstanding$600,000+$345,000/yr$30,000
25%Best Practice (est. firms)$750,000+$495,000/yr$30,000

Sources: Lawn & Landscape industry benchmark (10% = good, 15% = very good, 20% = outstanding); ArborNote research (15+ year established firms reach 30–45%); specialized PHC services deliver 30–50%. Sperry's 35-year tenure, ISA credentials, and Lane County market position support targeting 20–25% as a realistic 24–36 month goal.

Revenue Growth + Margin Improvement — With Timeline

Scenarios are mapped to realistic achievement windows based on when the key initiatives that drive each milestone come online. Not a guarantee — a planning frame.

Baseline today: ~$3.0M revenue × 8.5% margin = $255,000/yr in contribution margin. "Incremental" = new profit above that line.

Horizon Scenario Revenue Margin Incremental Profit Above Baseline Total Annual CM What Gets You There
Year 1
End of 2026
Conservative $3.2M 12% +$129,000 $384,000 Club members booking; Spring Pruning campaign; Meta paid leads; SOW Workstream 4 automations closing the follow-up gap. Margin improvement from reduced lead leakage and first recurring revenue.
Year 2
End of 2027
Moderate $3.5M 18% +$375,000 $630,000 Subscription program live with 150–200 members; Cummings list activated; Google Search running; new site driving inbound; PHC service line added; Jobber booking reducing friction. Margin driven by recurring revenue mix and smarter pricing.
Year 3
End of 2028
Optimistic $4.0M 22% +$625,000 $880,000 300+ subscription customers; service area expansion underway; 1–2 acquisitions integrated; VIP annual contracts normalized; PHC at scale. Margin driven by recurring revenue base and service mix shift away from pure removal.
Year 3–5
2028–2030
Best Case $5.0M 25% +$995,000 $1,250,000 Multi-market presence; subscription base at 400–500; dominant regional brand; acquisition playbook proven. Exit valuation at this level: $6.25M–$7.5M at 5–6× EBITDA. This is the exit scenario.

Projections are estimates. Timelines assume consistent execution and no major operational disruptions. Storm years and market conditions will affect pace. Margin improvement depends on pricing strategy, service mix, recurring revenue programs, and operational efficiency gains. The Year 1 conservative scenario is the floor expectation from Q2–Q4 execution of SOW BT-STC-Q2-2026 alone.

These projections assume organic growth within the current service area. Acquisitions and expansion push the ceiling well beyond these numbers.

Every scenario above is based on Sperry's existing operation — same geography, same service lines, same crew capacity. They represent what's achievable by optimizing and marketing what already exists. That alone is a compelling case.

Sperry already operates across Lane and Benton Counties — a two-county service area anchored in Eugene and extending north through Corvallis and Junction City, south through Cottage Grove, and east toward Oakridge. That is a larger and more valuable footprint than most regional competitors. But it also means the adjacent expansion opportunity is proportionally larger. The natural next markets are not just neighboring towns — they are Douglas County to the south (Roseburg), Linn County to the north (Albany/Lebanon), and the southern Willamette Valley corridor connecting them. Each of these markets has aging residential tree canopy, established homeowner bases, and limited ISA-certified competition.

A single acquisition of a $500K–$1M operator in any of these adjacent markets adds revenue immediately — with a customer list, equipment, and crew relationships already in place. Two acquisitions over three years and Sperry is a $5M+ multi-county operation well before the Best Case timeline. But the real multiplier is what happens when those acquired businesses run on Sperry's upgraded infrastructure — the CRM, marketing automation, subscription program, SOPs, and digital presence being built through this engagement. New hub locations inherit the platform instead of building from scratch. That is how a regional tree care company becomes a multi-market brand, and how revenue scales to $8M–$10M+ with the right execution. The scenarios above don't model any of this. They are the organic floor — what happens with disciplined execution inside the current footprint — not the ceiling of what's possible.

Margin compounds with scale independently of everything else. A larger revenue base spreads fixed costs — insurance, equipment, management overhead — across more jobs. At $5M revenue with current cost structure, net margin improves materially from operating leverage (fixed costs stay flat while revenue grows, so profit margin expands automatically) alone, before a single PHC upsell or subscription program is counted. Every acquisition accelerates this dynamic.

And these are only the opportunities we can see today. Every project on this roadmap — Jobber optimization, QuickBooks access, Quo call data, the subscription program buildout, the Cummings integration — will surface additional revenue and margin opportunities that aren't visible yet. The numbers above will look conservative by the time we're 12 months into execution.

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Section 01b · Strategic Growth
Subscriptions, Scale & Market White Space
The biggest lever in tree care is not more campaigns. It's predictable recurring revenue and deliberate expansion into available demand.

Annual subscription programs are industry standard — and Sperry doesn't have one yet.

The highest-margin tree care companies don't wait for customers to call when something is wrong. They sell annual care plans that include scheduled spring and fall visits, plant health care treatments, storm priority response, and arborist access. Monthly or annual billing. This is now standard practice for established regional firms — not a premium differentiator, but a baseline expectation among quality operators.

The business case is straightforward: a customer on a $1,200/year care plan generates predictable revenue regardless of storm activity. The Club's 988 members are the natural target audience. B5 Sweet Spot customers ($7,102 avg LTV (Lifetime Value — total revenue that customer has ever generated for Sperry), 27.9% conversion) are the natural pilot cohort. Even a 10% subscription uptake from Club members generates ~$118K in recurring annual revenue before a single new customer is acquired.

⚠ Subscriptions require operational readiness — staffing and service expansion.

Delivering on a care plan subscription means showing up on a schedule, not just responding to inbound calls. That requires: (1) dedicated scheduling capacity for recurring visits, (2) ISA-certified arborists who can perform PHC treatments (fertilization, soil aeration, pest and disease management, cabling and bracing) that may be outside Sperry's current service mix, and (3) possible hiring to cover the recurring visit volume without displacing storm-response and removal capacity.

This is not a reason to wait. It is a reason to plan deliberately — design the subscription tiers first, estimate the crew capacity required at 10%/20%/30% uptake, and identify which service lines need to be added or contracted. BOSSTORQUE can build the subscription marketing infrastructure; the operational decisions are yours to make with full data in front of you.

This is already being done. Here's how other firms are running it.

These are real programs from operating tree care companies — not hypotheticals. The structure varies but the model is consistent: scheduled annual visits, bundled PHC treatments, priority scheduling, and a guarantee or warranty that removes the customer's risk of saying yes.

Arbor Image Tree Care (Oklahoma City, OK)
Offers a branded "Tree Health Membership" with two tiers: Standard (quarterly visits, 4 annual inspections, deep root feeding spring and fall, insect/fungal/bacterial treatments, soil amendment, dormant oils) and a Premium tier with additional services. Comes with a "Healthy Tree Guarantee" — if a tree they plant dies under the Standard plan, they replace it at no cost. The guarantee requires at least 1 year of continuous program enrollment. Pricing is custom per property after a free inspection. The program is billed as their primary service offering, listed before tree removal in their nav. They market it as "take the work out of your tree maintenance" — predictable monthly cost, no decisions, no surprises.
Source: thearborimage.com/about/healthy-tree-guarantee

Joshua Tree Experts (PA/NJ/CO/TX — franchise)
Offers tiered "Arbor Shield" PHC programs — Standard and Advanced — for trees and shrubs. Standard covers the common local issues: dormant oils, insect treatments, bacterial and fungal treatments, spring and fall deep root feeding, soil amendment and conditioning, complete property evaluations. Advanced adds prescription-level treatments. Pricing is based on quarter-acre residential property and is publicly posted. Customers can pay-as-you-go or prepay the full annual program for a 5% discount — a simple conversion lever. The program is central to their recurring revenue model; they run it across 19+ franchise locations with PHC comprising roughly 30% of total revenue.
Source: joshuatreeexperts.com/plant-health-care-pricing

SavATree (35+ locations, national)
Runs ongoing annual maintenance plans as a core commercial and residential offering — not an upsell. Every client gets a certified arborist assigned for seasonal walkthroughs, proactive pruning, fertilization, disease treatment, and risk assessments on a scheduled calendar. They specifically market the program to commercial property managers by showing how it converts reactive emergency spending into a predictable budget line item. Their PHC-first model is a central reason they've grown to $200M+ in revenue and have been acquired multiple times at premium multiples. SavATree is also actively acquiring regional operators — exactly the competitive threat Lane County needs to prepare for.
Source: savatree.com

Davey Tree Expert Company (national, $1B+)
Runs comprehensive PHC programs across both residential and commercial — using proprietary products (Arbor Green PRO, Phosphorous-free Arbor Green, Arbor Green Xtra plus B) blended for specific regions. Every commercial client is assigned a dedicated arborist for long-term monitoring. Their recurring program revenue is what has enabled 140+ years of continuous operation, including through storm years, recessions, and regional market disruptions. Davey is proof of concept that PHC-anchored recurring revenue is the structural foundation of a durable tree care business at any scale.
Source: davey.com/commercial-services

The business case from industry data: PHC helps tree care professionals develop a recurring revenue model — you can only cut down a tree once, but you can treat trees over and over. PHC programs frequently deliver 30–50% margins, requiring fewer resources but offering expert-level fees. That is the highest-margin service line in tree care, and it compounds year over year as the customer relationship deepens.

Subscription revenue compounding: illustrative model

At $1,200/yr average plan, 10% Club uptake (99 members): $118,800/yr recurring. At 20% (198 members): $237,600/yr. At 30% (296 members): $355,200/yr. These revenues occur independent of storm seasons, marketing spend, and new customer acquisition. They compound annually as the Club grows — and they're the exact type of recurring revenue that drives business valuation multiples at exit.

How much white space is in the current service area?

Sperry already operates across Lane and Benton Counties — a two-county footprint covering Eugene, Springfield, Corvallis, Junction City, Cottage Grove, and Oakridge. Combined population is approximately 500,000 residents across roughly 200,000 households. Conservative penetration assumptions for residential tree care suggest 15–20% of households have a meaningful service need in any given year — roughly 30,000–40,000 addressable households annually in the current service area alone.

Sperry's current customer database of ~10,000 contacts represents approximately 5–6% penetration of that addressable base. There is significant room to grow before hitting a demand ceiling in the existing footprint. The subscription program specifically helps here: predictable recurring visits enable better crew utilization and reduce the feast-or-famine scheduling cycle that currently limits how aggressively Sperry can take on new work. Growth is not unlimited within the current geography — crew capacity and scheduling are real constraints — but Sperry is nowhere near them yet.

Geographic expansion and acquisition as growth levers

Sperry is already a two-county operator. The adjacent opportunity is proportionally larger than a single-county shop would face. To the south: Douglas County (Roseburg) — a market with established residential density, aging canopy, and limited ISA-certified competition. To the north: Linn County (Albany, Lebanon, Sweet Home) — similar profile, underserved. The full southern Willamette Valley corridor, connecting these markets with Sperry's current footprint, is the natural expansion zone.

Competitor acquisition is frequently faster and cheaper than organic entry into a new market — it brings a customer list, equipment, crew relationships, and local reputation simultaneously. Cummings is the first move in this direction. If it executes cleanly — list activated, revenue generated, integration smooth — Sperry has a proven acquisition model it can repeat in Douglas County, Linn County, or anywhere the right opportunity surfaces.

The larger opportunity is what happens when acquired companies and customers are brought under Sperry's upgraded infrastructure and operating model. Every system being built through this engagement — the CRM, the marketing automation, the phone system, the subscription program, the SOPs, the digital presence — is designed to be replicable. A Roseburg operator running on paper and phone calls becomes a significantly more valuable business the day it connects to Sperry's infrastructure. New hub locations don't need to rebuild from scratch. They inherit the platform. That is the difference between acquiring a customer list and building a regional brand — and it is what justifies valuation multiples well beyond what any single-location tree care company commands.

⚠ The competitive window is not permanent. Outside firms are looking at the Willamette Valley.

Regional tree care consolidators and well-capitalized operators — SavATree, BrightView, and franchise operators like Joshua Tree Experts — are actively expanding into secondary Oregon markets. The southern Willamette Valley is an attractive target: two-county population of ~500,000, above-average homeowner income, aging urban canopy, and a fragmented competitive landscape of mostly small independent operators. Cummings closing is exactly the signal that draws outside attention.

Sperry's structural advantages — 35 years of reputation, ISA credentials, community trust, TCIA accreditation, and a 10,000-contact validated database — are real. But they are time-limited advantages. A well-funded operator entering the market with a subscription program, digital infrastructure, and an acquired customer list could establish meaningful presence in Lane or Benton County within 18–24 months. The moves on this roadmap — subscription programs, Cummings acquisition, service area expansion into Douglas and Linn Counties, digital dominance — are also defensive plays. Build the moat before someone builds it around you.

Exit value: what this plan builds toward

Every decision on this roadmap has a dual purpose: improve current-year cash flow and increase business sale value. Tree care businesses without recurring revenue sell at 2–3× EBITDA (Earnings Before Interest, Taxes, Depreciation and Amortization — the standard measure of business profitability used in valuations). Businesses with documented recurring revenue — subscription programs, annual contracts, membership-based retention — sell at 4–6× or higher, because a buyer is acquiring predictable future cash flow, not just equipment and a list.

At $3M revenue with a 20% margin target ($600K EBITDA), the difference between a 2.5× and a 5× multiple is $1.5M vs. $3M in exit proceeds. The subscription program alone — if it generates $250K–$350K in recurring annual revenue — could add $750K–$1.75M to that exit number.

Five additional exit value drivers this plan builds directly:

1. Documented, segmented customer database. Buyers pay for organized, RFM-scored (Recency, Frequency, Monetary — a scoring model that ranks customers by how recently they bought, how often, and how much), validated contact lists. Unorganized goodwill ("we know our customers") does not transfer at a premium — structured data does.

2. Knowledge Vault / SOPs. Key-man dependency on you as owner is the single largest valuation discount buyers apply to owner-operated service businesses. Documented expertise transfers. Tribal knowledge doesn't.

3. Brand and digital presence. SEO authority, review volume, social following, and website conversion infrastructure are transferable assets. They reduce a buyer's cost to maintain revenue post-acquisition.

4. Acquisition history. A business that has successfully integrated a competitor (Cummings) demonstrates a repeatable growth model. Strategic buyers pay a premium for proven acquisition capability — it signals scalability.

5. Technology stack. Automated phone handling, CRM, email marketing, and reporting systems reduce buyer integration cost and risk. They also signal a modern, manageable operation rather than a relationship-dependent one-man show.

None of these are abstract. Every project on this roadmap contributes to at least one of them. The question is not whether to build them — it's whether to build them now, while Sperry controls the timeline, or later, under competitive pressure.

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Section 02 · Immediate Priority
Sign These Now
One consolidated SOW. Four integrated workstreams. Two have hard seasonal deadlines. Every week of delay costs real revenue.

SOW BT-STC-Q2-2026 is on the table and ready for signature.

One consolidated SOW. Four integrated workstreams. $17,000 total — $4,500 at signing, then $2,083/mo through September 1. All deliverables complete by June 30. Two workstreams have hard seasonal deadlines. Every week of delay costs real revenue.

Workstream 1 · Web Security + Phase Zero · $3,500
Workstream 2 · Q2 Member Marketing · $3,500
Workstream 3 · Meta Paid Social · $7,500
Workstream 4 · Lead Warming + Club Welcome · $2,500

Workstream 2 — Spring Pruning deadline

The Spring Pruning campaign targets ~April 20 launch to catch peak pruning season demand. The $72K–$132K revenue influence is front-loaded — delayed launch shrinks the window. At 15% margin, that's $10.8K–$19.8K profit influence. Sign now, start building immediately.

Workstream 1 — Q3 site build dependency

Phase Zero design feeds directly into the Q3 full site build — which is a separate proposal, delivered after Phase Zero is complete. If Phase Zero doesn't start in April, the Q3 launch slips to Q4. The security hardening is also a live risk that can't wait.

The expanded roadmap is a separate conversation.

Everything beyond this SOW — the CM (Contribution Margin — revenue minus direct costs, the basis for the performance fee) performance model, Cummings, Quo, Elder Tree Forum, subscription programs, market expansion, and the full 9-month build — will be addressed as a structured proposal after Q2 is executing. Sign now. Build the bigger picture in April.

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Section 03 · Full Inventory
All 49 Projects
Every initiative identified since July 2025. Of the 13 projects completed or active, several were delivered as part of the engagement without separate billing — foundational work that would have been billed as standalone projects by most firms. Database reconciliation and RFM segmentation, ZeroBounce validation workflow, Kit custom field configuration, Zapier automation build, Home Show landing page and follow-up sequence, LinkedIn post calendar, and weekly reporting infrastructure. At standard agency rates, that work totals approximately $15,000 delivered without a separate invoice. That's how BOSSTORQUE operates: no nickel-and-diming on high-leverage work with minimal incremental effort. Priorities and sequencing are in Section 04 (Timeline).
Foundation — Data, Tech Stack & Infrastructure
6
#01
PowerLeak Assessment
Done
Diagnostic completed July 2025. 5 revenue leaks identified totaling $200K–$400K annual opportunity. Foundation for all subsequent work.
#02
Database Reconciliation + RFM Segmentation
Done
10,800+ records reconciled. Full RFM scoring across VIP, High Value, Medium, Low, Legacy, At-Risk. 9 production batch files. B5 Sweet Spot: $7,102 avg LTV, 27.9% conversion — seed for all future targeting and Meta lookalike audiences.
#03
ZeroBounce Email Validation Workflow
Done
Validation pipeline embedded in every batch. 1,183 invalid/abuse/spam addresses excluded pre-send. Protects domain reputation for all future campaigns permanently.
#04
Kit Setup — Custom Fields, Sequences & Automations
Done
18 custom fields configured and populated. Visual automation live. Tag taxonomy established. Kit/Jobber fully reconciled March 23. Platform is production-ready for all future campaigns.
#05
Zapier Automation: CF7 → Kit → Jobber
Done
6-step Zap live. Club join → Kit tag + field update → Jobber client lookup → Club Member tag → conditional SMS opt-in. End-to-end tested and reconciled.
#06
Google Workspace Migration
Next
Wyatt has completed the server rebuild. The question now is whether to stay on-premise or move email, calendar, contacts, and file sharing to Google Workspace permanently. Up to 10 users. Google Workspace eliminates the server as a single point of failure and removes Sperry's IT dependency entirely. Previously scoped at $6K standalone — now bundled with cloud migration.
Security & Infrastructure
3

The server rebuild is done. Now make a decision that never has to be made again.

Wyatt has rebuilt the server. That buys time — but it doesn't change the underlying situation. Sperry is still running email, the website, calendar, and file storage on physical hardware in a single location. Every day that continues, Sperry carries risk that cloud-hosted businesses don't: a hardware failure takes everything offline simultaneously; a power outage or internet disruption means nobody can access email or files; security patches require manual attention from Wyatt; and the 2020 malware incident is a reminder that on-premise servers are harder to protect than managed cloud infrastructure.

The right move — now, while the server is fresh and before the next issue surfaces — is to migrate everything to the cloud and never think about the server again.

What moves to the cloud — and what that means

Email and calendar → Google Workspace. You, Michele, Asa, Alby, and the full team get professional @sperrytreecare.com email hosted by Google. Shared calendars, contacts, and Drive storage. Accessible from any device, anywhere. No server dependency. $12/user/mo for up to 10 users ($120/mo total) — less than a tank of gas per user per month.

Website → managed cloud hosting. Sperry's WordPress site moves off the physical server to a managed cloud host (WP Engine, Kinsta, or similar). Automatic daily backups. One-click restore. CDN-delivered speed. Automatic security updates. If the server were to fail tomorrow, the website stays up because it's no longer on the server.

File storage → Google Drive. Shared drive for Sperry's documents, photos, contracts, and files. Accessible by the full team. No more emailing files or "where did I save that?" Version history on every document. Searchable from anywhere.

Why this makes sense right now

The hard part is done. Wyatt's rebuild means there's no emergency driving a rushed migration. The migration can be planned and executed cleanly, with data verified before anything is cut over. This is the best possible window — do it deliberately rather than reactively after the next incident.

It removes a permanent operational risk. Physical servers fail. They get compromised. They require someone with Wyatt's expertise available when something goes wrong. Cloud infrastructure is managed by Google and the hosting provider — they have full-time security and infrastructure teams. Sperry gets enterprise-grade reliability without enterprise IT costs.

It enables everything else on this roadmap. Quo phone integration, Jobber booking flow, Meta Pixel (code that tracks website visitors for ad targeting), GA4 (Google Analytics 4 — measures site traffic, leads, and conversions), Kit automation — all of these work better and more reliably when the web infrastructure underneath them is cloud-native and professionally managed.

It costs less than staying on-premise. When you factor in Wyatt's time, hardware maintenance, backup infrastructure, and security management, on-premise hosting at Sperry's scale costs more than $120/mo in Google Workspace plus $30–50/mo in managed web hosting. The cloud is cheaper and better.

#07
WordPress Security + Phase Zero Design
Next
SOW BT-STC-Q2-2026 Workstream 1 — on the table. Security hardening (target: complete by Mar 28): Wordfence Premium, 2FA, plugin audit, automated backups, GA4 + Meta Pixel analytics layer. Phase Zero design (~6 weeks): 3 production comps, feature architecture, Jobber estimate flow. Q3 full site build is a separate proposal after Phase Zero is approved — expected $8K–$15K depending on final scope.
#08
Mail/Web Server Rebuild
Done
Wyatt Cull has completed the server rebuild. The patching and vulnerability backlog is resolved. The previous malware exposure is remediated. The rebuilt server is the foundation — the next decision is whether to keep it on-premise or move to cloud hosting permanently. See Section 03 for the full cloud migration case.
#09
Cloud Migration — Mail, Web & File Servers
Next
The server rebuild is done. The window to move to cloud hosting is now open. This means: website hosting moves off the physical server to managed cloud (faster, auto-scaled, auto-backed-up); email and calendar move to Google Workspace; file storage moves to Google Drive. No more server dependency, no more Wyatt on call for hardware issues, no more single point of failure. The cost to run it is lower than maintaining on-premise hardware. This is the decision to make at the March 25 meeting.
Email Marketing & Customer Retention
10
#10
Sperry Tree Care Club — Full Program
Done
Free loyalty membership. Landing page, 4-email sequence + Legacy variant, welcome automation. 988 members, 56.78% open rate, 10.15% conversion vs. 1–3% industry. The flywheel's foundation.
#11
Full Database Deployment — B1–B12
Done
All 12 batches deployed — 9,730 contacts (99.8% of validated list). B12 sequence completes ~March 27. Final member count in March 30 report. Campaign infrastructure fully proven.
#12
Home Show Landing Page & Lead Capture
Done
Lane County Spring Home & Garden Show (Mar 13–15). Landing page, Kit + Jobber routing, automatic estimate request generation. 68 leads. Michele: every QR form lead was warm and scheduled immediately.
#13
Home Show Follow-Up Sequence
Done
Deployed to all 68 leads. 16 Club Charter Members entering Q2 nurture. Estimate-to-job target 40–60% (warm, self-selected homeowners).
#14
Club Charter Member Nurture (Home Show)
Active
16 Home Show Charter Members in dedicated Q2 nurture track. Converting to booked services and deepening early loyalty.
#15
Q2 Member Marketing + Spring Pruning
Next
SOW BT-STC-Q2-2026 Workstream 2 — on the table. 11-email Club nurture sequence (residential + commercial versions). Spring Pruning broadcast ~April 20. Full Q2 email calendar through June 30. Revenue influence: $72K–$132K. At 15% margin: $10.8K–$19.8K profit influence. Seasonal deadline — April 20 launch window is fixed.
#16
Lead Warming + Club Member Welcome
Next
SOW BT-STC-Q2-2026 Workstream 4 — on the table. 3-email lead warming sequence on every new estimate request (stops when job is booked). 4-email Club welcome on every new member join. Live by April 27. Revenue recovered: $25K–$30K/yr. At 15% margin: $3.75K–$4.5K/yr. Runs permanently once built.
#17
Club Member Benefit Operationalization
Next
12 Club benefits promised to 988 members but not fully delivered: Free Health Checks, Standby Crew Access, Early Warning Alerts, Friends & Family Referral Bonus, Q&A with Arborist, Member Hotline. Scheduling systems and automation behind each benefit needed.
#18
Win-Back Campaign (Lapsed Customers)
Later
Contacts with Last_Service_Date > 12 months, segmented by LTV tier. Next highest-ROI outreach available after B5 Sweet Spot $5K+ LTV non-members. High-LTV lapsed customers are the most recoverable revenue in the database.
#19
Annual Subscription Program (Service Contracts + PHC)
Later
Recurring annual care contracts for VIP and High Value customers. Subscription pricing covers: spring safety check, pruning visit, PHC treatment, priority scheduling, and storm response priority. Monthly or annual billing. Industry standard for established tree care firms — directly smooths seasonality, reduces storm-spike dependency, and enables workforce planning. Requires hiring ISA-certified arborists and possibly adding service lines (fertilization, soil aeration, pest/disease management) beyond Sperry's current portfolio. The subscription base also enables geographic expansion and acquisition activity by providing a predictable revenue floor.
#20
Seasonal Automated Campaigns
Later
Spring, summer, fall, and winter campaigns triggered by date. Once built, runs with minimal maintenance. Core of the marketing calendar and the sustainability of the flywheel long-term.
New Lead Generation & Top-of-Funnel
6
#21
Meta Paid Social — Q2 Residential
Next
SOW BT-STC-Q2-2026 Workstream 3 — on the table. Full campaign build and execution through June 30: account setup, custom and lookalike audiences, static + video creative, Kit landing pages, weekly optimization, A/B testing, retargeting. Ad spend billed to Sperry at cost, no markup. Recommended Q2 spend: $1,500–$2,500/mo. At $70 CPL (Cost Per Lead — ad spend divided by leads generated): ~36 leads/mo → ~107 Q2 leads. At 28% close, $850 avg job: $25K–$32K Q2 revenue.
#22
Storm & Safety Lead Magnet
Later
Opt-in PDF checklist for storm prep. Email capture before download. Promoted via Google/Facebook ads seasonally. Strong fall funnel builder — feeds new contacts into the Club pipeline at near-zero incremental cost.
#23
"Ask an Arborist" Q&A Funnel
Later
Website form: name + email + tree question. Expert email reply. Positions Sperry as go-to authority, captures new contacts at zero ad spend. Leverages your and Alby's expertise at scale.
#24
Neighborhood Spotlight Campaign
Later
Yard signs + door hangers + Facebook geo-targeting around active job sites. Mobile form for name/email capture. Converts job-site visibility into a continuous lead channel. Low cost, high local relevance.
#25
Referral Program
Later
Friends & Family referral bonus already promised as a Club benefit to 988 members. Automated tracking and incentive delivery via Kit/Jobber. Zero ad cost lead source once operationalized.
#26
Cummings Customer List Acquisition
New
Competitor going out of business. See Section 09 for full valuation framework, two acquisition paths, equipment opportunity, and negotiation strategy.
Paid & Organic Social
5
#27
LinkedIn Organic — Tree Care Industry Presence
Active
8-week organic post calendar launched March 23. Sperry's story — 988 Club members, 10.15% conversion, 35 years of expertise — positioned as a model for the industry. Builds Sperry's brand authority with a broader professional audience. Separate from Sperry's direct marketing costs.
#28
LinkedIn Paid — Video + Lead Gen Form
Next
Paid campaign reaching tree care decision-makers in OR/WA/ID/NV/AZ/CA + BC. Activates ~Week 4–5 after organic data builds. $500 Sprint 1 cap. Not a Sperry cost — BOSSTORQUE funds and manages this campaign to amplify Sperry's story to a professional audience.
#29
Google Search — Local Demand Capture
Later
High-intent local search ads for Sperry: "tree removal Eugene OR," emergency storm calls. Activates Q3 after site refresh. Ad spend: $1,500–$3,000/mo (Sperry-funded). Managed by BOSSTORQUE under retainer.
#30
Retargeting — Meta + Google
Later
Meta: website visitors 30d, booking page visitors 30d. Google display retargeting. Builds alongside Q2 Meta campaign. CPL drops 40–60% vs. cold once audiences qualify. Q3 campaigns start cheaper because Q2 work was done.
#31
April 3 Video Shoot — Your Property
New
Production firm directing. Jason attending as observer. You removing your own trees. 5 assets planned. Post-production TBD. See Section 10 for brief and specs.
Website, SEO & Online Presence
4
#32
Website Refresh — Q3 Full Build
Next
Phase Zero (Workstream 1 of current SOW) produces the design comps and feature spec. Q3 full site build is a separate proposal after Phase Zero is approved — expected $8K–$15K. New design, mobile optimization, Jobber estimate booking, Club integration, GA4 + Meta Pixel from Day 1. Phase Zero must start April or Q3 slips to Q4.
#33
SEO — Local Search Optimization
Later
Jobber SEO report (currently 77%), FAQ page, Google Business Profile optimization, Cloudflare, structured data markup. Long-term organic traffic compounding — every dollar invested grows in value over time.
#34
Online Booking Integration
Later
Self-serve estimate scheduling via website → Jobber. Michele's top operational priority. Reduces phone load immediately. Captures after-hours and mobile traffic currently going to voicemail.
#35
Review Generation & Reputation Management
Later
Jobber already handles automated post-job review requests. This project focuses on the strategy layer: review velocity targets, Google + Yelp monitoring, response templates, and linking review volume to local search rankings. Every new review compounds permanently.
AI Systems & Automation
6
#36
Quo Phone System (formerly OpenPhone)
Next
Your priority AI initiative. Full phone system replacement: Sona AI receptionist, shared inbox (Michele/you/Elta), native Jobber integration (every call logs automatically), SMS native, AI call summaries in 60 seconds. $69/mo platform + $25–75/mo Sona credits (realistic volume). BOSSTORQUE implementation: $2,000–$3,000 est. — covers Sona KB build, call flow design (business hours + after-hours + emergency routing), Jobber integration, Zapier automations, TCR registration, testing, and go-live. Note: some unknown scope in the Sona KB build and Zapier automation depth — confirmed at kickoff. Research is done. Ready to scope and sign.
#37
SMS Activation (307 Opt-Ins)
Next
307 opt-ins reconciled, nothing sent. TCR registration required (~$20–25 one-time). Quo handles SMS natively. First campaigns: seasonal reminders + estimate follow-ups. Immediate revenue from a list already built.
#38
Jobber Optimization
Later
Unlock Jobber's underused features: online booking, automated follow-ups, job completion emails, custom reporting. The scheduling + estimate booking Michele wants lives here. High leverage, no additional platform cost.
#39
Estimate Call Coaching (Quo/Sona)
Later
Quo generates AI call scorecard after every estimate call: greeting, needs discovery, objection handling, close rate. Quarterly review with you. Directly improves close rates without adding headcount. Activates after Quo go-live.
#40
BI / Revenue Reporting Dashboard
Later
Revenue by service type, conversion rates, seasonal trends, campaign ROI, margin tracking. Requires QBO access (in progress) and stable upstream data. Essential for measuring margin improvement toward the 20–25% target.
#41
Your Voice Avatar (ElevenLabs)
Later
Clone your voice for the AI receptionist — disclosed to callers as "your AI." ~$99+/mo platform. Deferred pending Quo/Sona live results. High differentiation play — nobody else in Lane County will have this.
Events, Content & Community
5
#42
Elder Tree Forum
Next
Your #1 passion project. Educational event at Owen Rose Garden targeting homeowners 55+ with large legacy trees. Free, educational, zero sales pressure. Scoping with Alby still pending. Target: June/July 2026. Leads to Elder Tree Check-Up funnel.
#43
April 3 Video Shoot — Your Property
New
Production firm directing. Jason attending as observer. You removing your own trees. 5 assets: decision walk-through, process B-roll, before/after, safety moment cut (30–45s), quiet closer. Editing and post-production TBD. Covers Sperry's content needs through Q3 2026.
#44
New Office Open House
TBD
Customer-facing open house upon completion of the new office. Date not yet set — timing tied to office build-out completion. Opportunity to strengthen community ties, showcase the operation, and deepen relationships with existing customers.
#45
Marketing Calendar — Member Communications
Later
Full 12-month editorial calendar: newsletters, seasonal alerts, educational guides, event invites, holiday touches. Delivers on Club benefit promises systematically. Backbone of the flywheel once built.
#46
Sustainability & Carbon Story
Later
Position Sperry as environmental leader aligned with McKenzie River Trust and KLCC partnerships. Carbon impact content for PR and community marketing. Differentiates Sperry from price-competing competitors on values — directly supports premium pricing strategy and margin improvement.
Knowledge, Strategy & Business Development
3
#47
Knowledge Vault / SOP System
Later
Capture your 35 years of expertise: species knowledge, hazard assessment, crew training, pricing rationale, customer communication playbooks. Reduces key-man dependency. Increases business sale value by 30–50%.
#48
Annual Tree Health Assessment Giveaway
Later
Quarterly drawing: entry = name + email. Promotes via social + community boards. Winners get free health check, non-winners get tip sheet + soft offer. Top-of-funnel list builder at near-zero cost.
#49
Cummings Customer List Acquisition
New
Competitor closing. Full analysis in Section 09: list valuation framework, two acquisition paths, equipment opportunity, and negotiation strategy.
↑ Back to Contents
Section 04 · Execution
9-Month Timeline
April – December 2026. Projects build on each other. Discoveries during implementation will surface additional scope. See Section 08 (Scope & Process).
9-Month Engagement · April – December 2026 · Full Picture
Q2 SOW — Sign Now
$17,000
$4,500 at signing · $2,083/mo Apr–Sep
Ongoing Retainer
$18,000
$2,000/mo × 9 months · Fixed, no increases
Additional Boosts (est.)
~$14,000–$15,000
5 projects · Quo phone ($2K–$3K est.) · Cloud migration ($3.5K) · Elder Tree Forum ($2.5K) · Jobber ($3K) · SOPs ($3K) · Initial estimates — each scoped and approved independently before work begins
Q3–Q4 Known + TBD
$8–15K+
Website build ($8–15K est., separate proposal after Phase Zero) · Additional Q3–Q4 boosts expected as execution reveals scope · Not all 9-month work is priced here
Fixed Advisory Fees · 9 Months
$57,000 – $65,000
Known scope only: Retainer + Q2 SOW + 5 boosts + website build · Additional Q3–Q4 projects will be scoped as engagement evolves · Each confirmed via change order before billing
Ad Spend — Sperry-Funded, Separate
$33,500 – $57,500
Meta + Google + LinkedIn · Your budget, zero markup
Performance Fee — Not Included Above
10% of new profit above today's baseline
Only paid when Sperry is making significantly more. If results are flat, this fee is $0. See Section 06 for how it works.
$0 if flat · ~$37.5K at moderate growth · your upside is 9×
Full 9-Month All-In — Fixed + CM Share, Three Scenarios
Flat results
$57K – $65K
Fixed fees only  ·  $0 CM share
Conservative growth
$70K – $78K
+~$12.9K CM share  ·  Sperry keeps $116K new profit
Moderate growth
$94K – $102K
+~$37.5K CM share  ·  Sperry keeps $337.5K new profit
Fixed advisory fees ($57K–$65K) are the factoring-eligible portion — they're committed and measurable. The CM share is contingent: it's paid quarterly from results as they arrive and cannot be pre-paid. See Section 06 for the full justification and how the math works.
All figures are estimates. Each project is separately scoped and requires written approval before work begins. Nothing expands without your sign-off.

Note on this document: This roadmap was prepared in one day as a structured proposal ahead of Wednesday's meeting. All boost project estimates are based on scope visible today — each requires a discovery session and written change order before work begins. Nothing is committed beyond the Q2 SOW until separately scoped and signed.

Important: This timeline represents the best planning view based on scope known today. Each project will surface implementation discoveries that may affect sequencing, effort, and timeline — that is expected and normal for strategic work at this scale. A defined change order process ensures nothing moves without clear agreement on cost and timeline. Dates marked "est." are estimates confirmed at project kickoff.

Apr
2026
Month 1
Sign SOW BT-STC-Q2-2026 — $4,500 deposit, all four workstreams launch immediately
Spring Pruning campaign build — target ~Apr 20 launch
WordPress security hardening begins
SMS activation — TCR registration + first campaign
Quo phone system kickoff — scope + sign
Meta paid campaign live ~Apr 6 (est.)
B12 final member count confirmed (Mar 30 report)
Lead warming + Club welcome sequences built + live
May
2026
Month 2
April 3: Video shoot at your property — production firm directs, Jason observes
Quo go-live — Sona handling after-hours calls
Phase Zero design comps delivered (~May 11 est.)
Cloud migration kickoff — Google Workspace + web hosting (Wyatt coordinates handoff)
Elder Tree Forum — confirm date, venue, Alby co-presenter
Meta Month 1 CPL review — scale or optimize
Retainer and partnership model formal proposal delivered
Cummings — you make first contact
Jun
2026
Month 3
Elder Tree Forum — Owen Rose Garden
Elder Tree Check-Up funnel live
April 3 video assets deployed across LinkedIn + Meta
Cloud migration complete — all mail, web, files on cloud
Q3 site build kickoff (Phase Zero complete)
Club member benefit operationalization begins
SMS campaign #2 to 307 opt-ins
Cummings acquisition — offer and terms
Jul
2026
Month 4
Q3 website launch — new site live
Google Search paid ads launch — local demand capture
Jobber optimization — online booking + follow-ups
Seasonal campaign: summer drought care + elder tree health
Elder Tree Forum ROI — jobs generated + conversions tracked
Cummings list campaign launch (if acquired)
Aug
2026
Month 5
SEO optimization — GBP, FAQ page, Cloudflare, structured data
Review generation automation live
"Ask an Arborist" funnel launch
Win-back campaign — lapsed customers (Last_Service > 12mo)
H1 performance review — revenue and margin vs. baseline
QBO access established — margin tracking begins
Sep
2026
Month 6
Fall campaign launch — peak season push across all channels
Storm & Safety lead magnet deploy
VIP annual service contract campaign (PHC + recurring)
Retargeting fully active — Meta + Google pools warm
Referral program soft launch to Club members
Oct
2026
Month 7
Peak season — all channels firing simultaneously
Knowledge vault / SOP capture begins
First CM share measurement — Q2/Q3 incremental profit calculated
Estimate call coaching: first quarterly scorecard review
Nov
2026
Month 8
Seasonal: winter prep + storm readiness campaigns
BI dashboard build (QBO + Jobber data stable)
Sustainability / carbon story — KLCC + MRT positioning
Club year-one anniversary campaign
Dec
2026
Month 9
Full-year ROI report — revenue, profit, margin vs. baseline
2027 roadmap + SOW planning session
Database re-validation + segmentation refresh
Annual CM share payment — first full-year calculation
Sperry: most recognized tree care brand in Lane County
↑ Back to Contents
Section 05 · Fees & Ad Spend
Investment Summary
Retainer stays at $2,000/mo regardless of how many workstreams are running. As results grow, BOSSTORQUE's compensation grows through the performance model — aligned with Sperry's outcomes, not with project volume. Boosts are one-time project fees. Ad spend is separate, Sperry-funded, BOSSTORQUE-managed.

All figures are estimates based on current scope. Each project will surface implementation discoveries that may require change orders. This is expected and normal for strategic work at this depth. BOSSTORQUE will never expand scope without prior written agreement. All changes are documented, priced, and signed before work begins.

ItemTypeInvestmentNotes
Retainer — Current Rate
BOSSTORQUE Monthly RetainerRecurring$2,000/moCurrent rate. Covers Club ops, LinkedIn organic, reporting, strategy, campaign management, and optimization across all active workstreams. Rate stays fixed as scope expands — BOSSTORQUE's compensation grows through the performance model when Sperry's results grow, not through retainer increases.
Q2 Growth System — SOW BT-STC-Q2-2026 · Ready for Signature
Workstream 1 — Web Security + Phase Zero DesignSOW$3,500Security complete by Mar 28. Phase Zero design comps by early May. Q3 full site build is a separate proposal after approval — expected $8K–$15K. Seasonal dependency — April start required.
Workstream 2 — Q2 Member MarketingSOW$3,50011-email Club nurture (residential + commercial versions) + Spring Pruning ~Apr 20. Revenue influence: $72K–$132K. Profit at 15%: $10.8K–$19.8K. Spring Pruning deadline is fixed.
Workstream 3 — Meta Paid Social Q2SOW$7,500Full campaign build + execution through Jun 30. Ad spend billed to Sperry at cost, no markup. Recommended spend: $1,500–$2,500/mo. Q2 revenue: $25K–$32K. Profit at 15%: $3.75K–$4.8K.
Workstream 4 — Lead Warming + Club WelcomeSOW$2,500Automated sequences live by April 27. 3-email lead warming on estimate requests + 4-email Club welcome on new joins. Revenue recovered: $25K–$30K/yr. Runs permanently once built.
Total Investment$17,000Payment: $4,500 at signing → $2,083/mo April through August → $2,085 September 1. All deliverables complete by June 30, 2026. Final payments run after campaigns are live and data is in hand.
Additional Project Boosts — Q2–Q4 (Initial Estimates · Scoping & Discovery Required)
Quo Phone System ImplementationBoost$2,000–$3,000 est.Sona knowledge base build, call flow design (business hours + after-hours + emergency routing), Jobber integration, Zapier automation setup, SMS TCR registration, testing, go-live. ~2–3 weeks. Some unknowns remain in KB complexity and Zapier depth — range confirmed at kickoff scoping session.
Cloud Migration — Google Workspace + Web HostingBoost$3,500 est.Server rebuild complete (Wyatt). Migration scope: Google Workspace setup (up to 10 users), website migration to managed cloud hosting, Google Drive file migration, DNS cutover, testing. Wyatt coordinates infrastructure handoff. Estimate — scope confirmed at kickoff.
Elder Tree Forum CampaignBoost$2,500 est.Event + registration page + Elder Tree Check-Up funnel + post-forum nurture. Scope confirmed with Alby.
Jobber OptimizationBoost$3,000 est.Online booking, automated follow-ups, job completion emails, custom reporting. Scope defined at discovery.
Knowledge Vault / SOP SystemBoost$3,000 est.Capture your expertise. Crew training framework. Key-man risk reduction. Scope defined at kickoff session.
Platform Costs — Sperry-Owned Subscriptions
Quo Business Plan (3 users) + Sona CreditsPlatform~$95–$145/mo$69/mo base (Business plan, 3 users) + $25–$75/mo Sona AI credits at realistic Sperry call volume. ~10 free calls/mo included; additional calls billed per credit block. TCR SMS registration ~$20–25 one-time + small monthly carrier fee.
Kit (ConvertKit)Platform~$49/moExisting. Scales with list growth.
Google Workspace (up to 10 users)Platform~$120/moProfessional email, calendar, Drive storage for the full team. Replaces on-premise mail server. $12/user/mo.
Managed Cloud Web HostingPlatform~$30–50/moWP Engine, Kinsta, or similar. Replaces website hosting on physical server. Automatic daily backups, CDN, security updates included.
Ad Spend — Sperry-Funded, BOSSTORQUE-Managed
LinkedIn Paid — Sprint 1Ad Spend$500 capBOSSTORQUE-funded campaign amplifying Sperry's story to a professional tree care audience. Not a Sperry cost.
Meta Paid — Q2Ad Spend$2,500–$4,000/mo$7,500–$12,000 over Q2. At $70 CPL: ~36–57 leads/mo. $25K–$32K Q2 revenue. Profit at 15%: $3.75K–$4.8K.
Meta Paid — Q3+ (ongoing)Ad Spend$3,000–$5,000/moQ2 warm retargeting pools → 40–60% lower CPL. Scale as data matures.
Google Search — Q3+Ad Spend$1,500–$3,000/moHighest-intent channel. Activates after site refresh. Storm damage, emergency calls, "arborist near me."
SOW BT-STC-Q2-2026 Total$17,000One SOW, four workstreams, all deliverables by June 30. Ad spend separate at cost.
Additional Boosts (est.)~$14,000–$15,000Initial estimates based on known scope — each project requires a scoping session and written approval before work begins. This is a one-day turnaround document prepared ahead of Wednesday's meeting. All figures subject to discovery and the standard change order process.
Est. Annual Ad Spend at Scale$45K–$84K/yrMeta ($2.5–5K/mo) + Google ($1.5–3K/mo) + LinkedIn ($500–1K/mo). Sperry-funded.
↑ Back to Contents
Section 06 · Strategic Compensation
The Partnership Model
You've seen the retainer + boosts model. This section explains why there's a performance component on top of it — and why that structure is better for Sperry than the alternative.

Why does a performance component exist on top of the retainer and project fees?

Because $2,000/mo is priced at cost, not at value. Running this engagement — the strategy, execution, campaigns, automations, reporting, and platform management across 49 projects — would cost $6,000–$10,000/mo at a full-service growth agency. A fractional CMO with this scope bills $5,000–$8,000/mo. BOSSTORQUE priced the retainer at $2,000/mo to make this accessible to a business at Sperry's scale. That's intentional. But it's only viable if there's a mechanism to participate when the work produces results above the baseline.

Here's the alternative — and why it's worse for Sperry. Without a performance component, the retainer would need to be $4,000–$5,000/mo to price this engagement at fair market value. At $4,500/mo, Sperry pays $54,000/yr whether results come or not. Under the current model, Sperry pays $24,000/yr in retainer — and the performance component only activates when CM exceeds today's baseline by a meaningful amount. If results are flat, total advisory cost is less than half what a comparable market-rate engagement would cost. The CM share is what makes the $2,000/mo retainer sustainable for both sides.

It's also a bet. BOSSTORQUE is accepting below-market fixed fees in exchange for upside that only materializes when the roadmap delivers real results. That isn't standard agency behavior — agencies charge the same rate regardless of whether the campaigns work. Accepting performance risk is a statement: BOSSTORQUE is confident enough in this roadmap to put its own compensation on the line. The pilot already proved the model. 988 members, 10.15% conversion, 48.7% open rates, a flywheel Rob called the most successful demand generation effort in Sperry's history. The performance structure is BOSSTORQUE doubling down on that outcome.

What you're actually buying with the performance fee: alignment. When BOSSTORQUE's compensation grows only because Sperry's margins grow, there is no incentive to run campaigns that look busy but don't move the needle, extend timelines to justify more hours, or recommend tools that add cost without adding revenue. Every decision BOSSTORQUE makes under this structure is filtered through a single question: does this increase Sperry's contribution margin? That's the goal. The fee structure enforces it.

BOSSTORQUE can scale to execute this — and the hard part is already done.

The work that's genuinely difficult to replicate is behind us: the full business diagnostic, 10,800-contact database reconciliation and RFM scoring, platform architecture, automation build, campaign infrastructure, and 8 months of learning exactly how Sperry operates, what its customers respond to, and where the revenue is. That institutional knowledge doesn't exist anywhere else. It took 8 months to build and can't be bought.

What remains is execution — and execution at scale is a capacity decision, not a strategic one. BOSSTORQUE owns every deliverable produced under this engagement — the strategy, the copy, the campaigns, the automations, the reporting. Full stop. When project volume calls for additional capacity, BOSSTORQUE brings in trusted specialists — copywriters, paid social managers, WordPress developers, automation engineers, designers — who are vetted, briefed, and managed by BOSSTORQUE. You never manage them. You never see the seams. The quality standard and the accountability stay in one place: here.

Sperry's intellectual property — customer database, contact records, business intelligence, brand assets, campaign performance data — is treated as confidential at every level of the engagement. Any specialist brought in to support a project operates under confidentiality obligations and accesses only what is necessary to complete their specific scope of work. Sperry's data does not get shared, repurposed, or exposed beyond what the work requires. That is a non-negotiable condition of working with BOSSTORQUE.

The 49 projects on this roadmap represent 2–3 years of deliberate execution at the current pace, or significantly less at higher throughput. The sequencing is already defined. The dependencies are mapped. The platforms are built and tested. When you say "let's move faster," the answer is yes — not "we need to go back to planning."

Performance Component · How It Works
The retainer stays at $2,000/mo — forever.
BOSSTORQUE earns more only when Sperry earns significantly more.
The Trade — What You're Comparing
ALTERNATIVE — Market Rate, No CM Share
$4,500–$5,000/mo
~$54K–$60K/yr retainer · Same whether results come or not · No performance alignment · You carry all the risk
THIS STRUCTURE — Low Fixed + CM Share
$2,000/mo + 10% of new profit
$24K/yr fixed · $0 extra if flat · CM share activates only when Sperry is winning · BOSSTORQUE carries performance risk alongside you
At moderate growth (Year 2): total advisory cost under this model is ~$61,500 — nearly identical to the alternative, except $37,500 of that is only paid because Sperry earned $375,000 it didn't have before.
The Mechanism — Four Steps
01
Set the baseline
Today: ~$3.0M revenue × 8.5% CM = $255,000/year in contribution margin. That's the starting line. BOSSTORQUE earns nothing on this number — it already exists.
02
Measure every quarter
Each quarter: calculate Sperry's actual CM — revenue minus direct costs (labor, materials, equipment) before overhead. Not just campaign revenue. The whole business, because the whole business is the scope.
03
Calculate the delta
Quarterly CM minus the baseline (prorated). If Sperry's CM is at or below $255K annualized, BOSSTORQUE earns $0 from the performance component. Zero.
04
Split 90 / 10
Of every new dollar of profit above the baseline: Sperry keeps $0.90. BOSSTORQUE earns $0.10. Invoice within 10 days of quarter close, after QBO data is confirmed.
Worked Example · Year 2 Moderate Scenario
Revenue
$3.5M
CM at 18%
$630K
Minus Baseline
−$255K
Incremental Profit
$375K
Sperry keeps — 90%
$337,500
New incremental profit, yours to keep
BOSSTORQUE earns — 10%
$37,500
Performance fee, paid quarterly (~$9,375/qtr)
9:1 return on the performance fee. For every $1 Sperry pays BOSSTORQUE in performance fees at this scenario, Sperry keeps $9 in new profit. Total advisory cost including retainer: ~$61,500. New profit kept: $337,500.
Storm-year protection: The baseline uses a rolling 3-year average with a defined storm-year adjustment. Abnormally high-revenue years from storm damage don't permanently inflate the baseline. Sperry doesn't get penalized for weather.
Data source & audit trail: Measured from QBO during the active engagement — BOSSTORQUE holds read-only access while the retainer is live. Each quarter, the CM calculation is exported and co-signed as a PDF that both parties retain permanently. During the 12-month tail, measurement shifts to standard financial documents Sperry already produces: CPA-prepared annual P&L, tax return, or equivalent certified statement covering the tail period. No continued QBO access required — these documents exist regardless of the engagement status and are the cleaner audit trail in any case. The engagement agreement specifies exactly which line items constitute CM so there's no ambiguity when it's time to measure. If Sperry disputes a measurement, either party can request a third-party CPA review — cost split equally.
Term — How Long Does This Run?
Initial Engagement
9 months · Q2–Q4 2026
CM share activates after QBO access is confirmed. Measured quarterly. First measurement: end of Q2 2026.
After Year 1
Annual renewal
Retainer and CM share continue year-to-year. Either party can exit with 60 days written notice. Terms reviewed annually — not unilaterally changed.
If Sperry Exits
12-month tail period
If either party terminates the retainer, the CM share continues for 12 months after the final active month. Measurement during the tail uses CPA-prepared annual financials or the tax return — documents Sperry produces regardless of the engagement status. No continued system access needed. The calculation methodology is locked in the engagement agreement so there's no dispute about the numbers when the time comes. BOSSTORQUE's right to invoice survives termination for the full 12-month window; after that, the obligation expires with no further claims on either side.
No Clawback
Fees are earned quarterly, not pre-paid
Performance fees are invoiced after each quarter closes and QBO data is confirmed — nothing is paid in advance. If a quarter is flat or down, that quarter's fee is $0. There is no clawback of fees already earned in prior quarters. The tail period uses the same measurement method.
HorizonScenarioSperry RevenueMarginIncremental Profit vs TodayPerformance Fee (10%)Retainer ($2K/mo)Total Advisory Cost
Year 1
End 2026
Conservative$3.2M12%+$129,000$12,900$24,000~$36,900
Year 2
End 2027
Moderate$3.5M18%+$375,000$37,500$24,000~$61,500
Year 3
End 2028
Optimistic$4.0M22%+$625,000$62,500$24,000~$86,500
Year 3–5
2028–2030
Best Case$5.0M25%+$995,000$99,500$24,000~$123,500

Retainer shown at current rate ($2,000/mo × 12 months). Performance fee is annual, paid quarterly after measurement. Baseline = 3-year rolling gross profit average with storm-year adjustment. Requires QBO read access — in progress. All figures are estimates.

Cummings — advisory scope and fee

The Cummings opportunity involves work beyond the current retainer scope: structuring the acquisition offer, reviewing consent documentation, building the activation campaign for any list acquired, and managing the Cummings-customer marketing program. BOSSTORQUE's fee for this work will be scoped and agreed separately before any offer is made to Cummings — so Sperry knows exactly what it costs before committing to anything.

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Section 07 · Expectations
Scope, Discovery & Change Orders
What we know now is not everything. How we handle what we learn professionally.

Projects at this scale surface discoveries. That's expected.

Every project on this roadmap is estimated based on known scope today. Sperry's systems — Jobber, QuickBooks, WordPress, the cloud migration — have their own complexity that reveals itself during implementation. Projects also build on each other: what we learn implementing Quo affects the lead warming sequences. What we learn in Phase Zero affects the Q3 site build scope. What we find in QuickBooks affects the margin measurement methodology.

This is not a limitation. It's the nature of strategic systems work at this depth. The goal is to surface discoveries early, price them honestly, and keep you informed throughout. Nothing expands without agreement.

Change Order Process

Any scope expansion beyond a signed SOW triggers a written change order before work begins. Every change order includes: scope description, effort estimate, fee, timeline impact, and rationale. No change order work starts without written approval from you. No exceptions. This protects both sides.

Payment Structure

SOW BT-STC-Q2-2026: $4,500 kickoff deposit at signing (non-refundable), then $2,083/mo April 1 through August 1, final payment $2,085 September 1. All deliverables complete by June 30 — final payments run after campaigns are live and Q2 data is in hand. Retainer monthly in advance. CM performance share measured quarterly, invoiced within 10 days of quarter close. Change orders billed at approval or milestone completion per change order terms.

How to think about these estimates

The fees in this deck are professional estimates based on known scope and comparable project experience. They are not fixed-price guarantees for open-ended strategic work. They are honest starting points with a defined process for managing what changes. BOSSTORQUE's commitment: we will never expand scope without telling you why, showing you what it costs, and getting your approval first. If something is simpler than estimated, the fee adjusts down. If we discover complexity that adds work, a change order is the mechanism. That is the deal on every project.

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Section 08 · New Opportunity
Cummings Acquisition
A local competitor is closing. Three distinct opportunities: customer list, equipment, and market share. All three are time-sensitive.

The Situation

Cummings, a local Lane County tree care competitor, is going out of business. Their closure creates three distinct opportunities for Sperry: (1) acquire their customer database, (2) acquire their equipment at liquidation pricing, and (3) capture their market share through positioning and outreach before a national competitor does. Move before the liquidation is advertised broadly.

You approach directly. Jason advises.

You are better positioned for the initial call. You know the industry, likely know the owner personally or by reputation, and a peer-to-peer conversation will move faster than a consultant making first contact. The goal of the first call: understand list size, consent status, equipment inventory, and wind-down timeline. Jason is available to join calls, structure the offer, advise on valuation and deal terms, and manage the activation campaign for any list acquired.

Five questions for the first call: (1) How many active customers are in the database, and what does "active" mean to them? (2) Were those customers opted into email marketing — is there a written consent record? (3) What equipment is available — full inventory with age and condition? (4) What's the wind-down timeline — how quickly do they need to close out? (5) Are they open to a combined deal (list + equipment) at a package price?

What Data in the List Actually Drives Valuation

Not all lists are equal. These fields determine what you're actually buying.

Before any offer is made, you need to understand what data exists for each customer record. The fields below are what separate a $5/contact list from a $15–20/contact list:

Service frequency: Customers with 2+ visits per year are recurring buyers — not one-time jobs. A list with documented service frequency tells you which contacts are active maintenance relationships vs. emergency-only calls. High-frequency customers are worth 3–5x more per contact than one-time removal clients.

Last service date: Recency matters. A customer last serviced 6 months ago is warm. Last serviced 4 years ago needs reactivation work. Ask for the distribution — what percentage of the list has been serviced in the last 12 months, 1–3 years, 3+ years?

Contact info completeness: Does every record have a phone number? Email? Physical address? A list with phone + email + address for each contact is significantly more valuable than names only. Email specifically enables digital reactivation at near-zero cost — without it, you're limited to direct mail.

LTV per customer: If Cummings has job history in their system (Jobber, ServiceTitan, QuickBooks), ask for average job value and total spend per customer. This is the most direct indicator of list quality. A list averaging $2,000/customer LTV (Lifetime Value — see glossary) is worth more than twice a list averaging $900/customer LTV — and it changes the acquisition math completely.

Geographic concentration: Are most customers clustered in Eugene/Springfield, or spread across the county? Concentration near Sperry's existing service area is more valuable — lower drive time, higher crew utilization, better upsell opportunity. A list heavy in areas Sperry doesn't currently serve well may require crew or service area expansion to activate effectively.

Service type mix: What percentage are removal clients vs. ongoing maintenance? Maintenance customers have recurring revenue potential. Removal-only customers are harder to reactivate. A list skewed toward maintenance contracts is worth a significant premium.

Path A — Buy Opted-In List (Preferred)

Purchase with contractual transfer of email consent rights. Email immediately under existing consent. Requires attorney-reviewed asset purchase agreement with specific consent transfer language.

Valuation: $5–$15 per opted-in contact in a local trades vertical. At 500 contacts: $2,500–$7,500. Up to $20/contact if LTV data shows high-value customers. Open at $5–$8/contact; settle around $10 if the list is clean and consent is documented.

Email immediatelyCleanest pathHigher cost

Path B — Buy Cold List (Low Cost)

Purchase at steep discount as names/addresses only — no consent transfer. Bridge to email via direct mail or CAN-SPAM-compliant cold outreach with a clear opt-in offer. More steps to activation, dramatically cheaper.

Valuation: $0.50–$2.00 per contact. At 500 contacts: $250–$1,000. Counter at $0.50/contact; settle around $1.00. You're buying the ability to introduce Sperry, not the right to email.

Much cheaperDirect mail bridgeMore steps

Equipment — potentially more valuable than the list

Commercial tree care equipment — chippers, bucket trucks, stump grinders, aerial lifts, rigging gear — depreciates heavily on paper but holds real operational value. A closing company almost always prefers a bulk sale: less hassle, faster cash, no logistics overhead. Sperry has significant pricing leverage by offering to take everything at once. You'll know what's worth having. If the equipment list is strong, a combined deal (list + equipment) at a package price gives Sperry maximum leverage and the seller maximum simplicity.

Cummings will think their list is worth more than it is. Here's how to handle that.

Every business owner overvalues their customer list. Cummings built those relationships over years and sees them as loyal, engaged, high-quality customers. The reality is that list quality degrades fast — last service date matters, contact completeness matters, consent status matters — and Cummings probably doesn't have clean data on any of those dimensions. The goal is to get Cummings to reveal the data quality problems before any number is discussed, so you're negotiating from facts, not feelings.

The inoculation sequence — run this before any offer is on the table:

Step 1 — Ask for the data, not the number.
Before you say what you're willing to pay, ask Cummings to pull their customer list and answer the six valuation questions in the section above: service frequency, last service date, contact completeness, LTV per customer, geographic concentration, and service type mix. Frame it as due diligence: "I want to make sure I'm making you a fair offer based on what's actually there." A seller with a strong list will pull it immediately. A seller with a weak list will hesitate, qualify, or deflect. That response alone tells you what the list is worth.

Step 2 — Let the data set the anchor, not emotion.
Once the data is on the table, walk through it matter-of-factly. If 60% of the list hasn't been serviced in 3+ years, that's not a list of 500 customers — it's a list of 200 active customers and 300 names that will need significant reactivation work at Sperry's expense. Reactivation cost (time, campaigns, low initial conversion) is real money that comes off the list's value. "I'd love to pay you for 500 active relationships, but what you've shown me is closer to 200 active and 300 cold. Here's what the math looks like."

Step 3 — Price the activation cost explicitly.
Even a clean, opted-in list of 500 doesn't generate revenue on its own. Sperry will run a re-engagement campaign (design, copy, deployment, follow-up), absorb the time cost of onboarding new customers, and likely see 20–40% of the list unsubscribe or go cold regardless. That activation cost — conservatively $1,500–$2,500 in BOSSTORQUE campaign work plus Sperry's crew time — comes directly off what the list is worth to Sperry. Putting that number in front of Cummings reframes the conversation: "Here's what it will cost me to activate what you're selling. That's not your problem — but it affects what I can pay."

Step 4 — Use the industry benchmark to close the gap.
If Cummings pushes back on price, Cite industry standard rates matter-of-factly: opted-in trades contacts in a local market trade at $5–$15 per contact. That's not your opinion — it's what buyers and sellers agree on. "I'm not trying to lowball you. This is what these lists sell for. If your data shows the quality is there, I'm happy to pay toward the top of that range. What I can't do is pay $30 or $40 per contact for a list that the industry values at $10." Having a number anchored to a market standard removes the personal element and makes the negotiation about data, not relationship.

⚠ The competitive bidder risk — This is important to understand.
The walk-away framing above assumes you are the only buyer. You may not be. Sophisticated acquirers — SavATree, BrightView, PE-backed regional operators, or even a well-capitalized independent — think about customer lists very differently than a local competitor does. They are not asking "what is this list worth to me today?" They are asking "what is the CAC (Customer Acquisition Cost — what it costs to acquire a new customer through advertising and sales) for a comparable new customer in this market, and how does the list price compare to that?"

A national operator with a $150–$300 CAC through paid channels would rationally pay $20–$30 per opted-in contact for a clean local list — because even at that price, the list is cheaper than buying the same customer through Google or Meta. Their LTV model extends over 5–10 years of managed service contracts, not a single job, so they can justify a price that looks absurd to a local operator doing per-job math.

If a sophisticated bidder is already aware of Cummings closing — and they will be, because liquidations surface on industry channels and broker networks — they will move quickly and pay a premium. That premium isn't irrational on their part. It's a strategic land-grab in a market they want to enter, funded by the economics of scale.

What this means for your timing and strategy:
You cannot afford to negotiate slowly. The right move is to make a fast, reasonable offer — anchored to data quality but not artificially low — before a more sophisticated bidder learns the list is available. A $5,000–$8,000 offer on a clean 500-contact opted-in list is fair and defensible. It is also fast, simple, and removes Cummings's incentive to shop the list further. A drawn-out negotiation or a lowball that insults the seller is an invitation for an outside firm to step in and pay more — and capture Lane County customers that Sperry will then spend $150–$300 each to win back through paid advertising.

The goal is not to get the cheapest price. The goal is to get the list before anyone else does, at a price that reflects actual data quality. Those are different objectives, and they lead to different negotiating postures. Negotiate firmly on data quality — but move decisively on price once the quality is confirmed.

BOSSTORQUE's role in the Cummings process

Jason is available throughout: advising on the acquisition structure, reviewing any consent documentation before an offer is made, building the activation campaign for any list acquired, and managing the Cummings-customer marketing program through to first bookings. The scope and fee for this work will be agreed before any offer is extended — no surprises.

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Section 09 · Content
April 3 Video Shoot
Production firm directing and producing. Jason attending to ensure the footage delivers what Sperry's campaigns need across every channel.

Why this footage matters for Sperry

A certified arborist removing trees from your own property — making the same call you make for clients, on your own home — is more compelling than any produced ad. It's proof in the most literal sense, and no amount of ad spend manufactures that story. The production firm handles execution quality. Jason ensures the footage delivers what the campaigns need: the right angles, the right sound bites, and the right technical specs for LinkedIn, Meta, and future paid placements across every channel Sperry runs.

Recommended brief for the production firm — 5 assets

Asset 1 — The Decision Walk-Through (2–3 min): You on camera explaining why these specific trees needed to come down. Your words, your reasoning, your property. Raw, unscripted, direct. Anchor piece for email, nurture sequences, and future ad edits.

Asset 2 — The Process (B-roll): Crew at work, equipment, the removal in sequence. No narration. Used across social and ad creative through Q3–Q4.

Asset 3 — Before/After: Wide establishing shots before and after. Clean, powerful. Meta Feed and website use.

Asset 4 — Safety Moment (30–45s): You to camera: "This is what I see that most homeowners miss." Short-form for LinkedIn paid VIDEO B and Meta Reels.

Asset 5 — The Quiet Closer: You standing in the cleared space. A few words about what protecting a property looks like when done right. Email closer and nurture anchor.

Technical specs — brief the production firm before April 3

Master format: Portrait 9:16 (1080×1920).
LinkedIn 16:9: Navy letterbox bars (#1E3A8A) top and bottom.
Meta Reels/Stories: Portrait source as-is.
Meta Feed 4:5: Center crop (1080×1350).
Raw footage: Minimum 45 minutes across the shoot day.
Audio: Lav mic on you for all on-camera speaking. Normalize to -14 LUFS (LinkedIn) / -16 LUFS (Meta) in post.
Raw footage handoff and editing coordination TBD based on final production arrangement. This footage covers Sperry's content needs through Q3 2026.

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Section 10 · Capacity
Recruiting & Hiring
Revenue growth without crew growth is a ceiling. Building the hiring infrastructure now is what lets Sperry keep pace with the opportunity.

The labor shortage isn't going away. Waiting on apprenticeship pipelines could take a decade.

85% of construction and trades companies report difficulty filling open positions. Skilled trades turnover hit 73% annually in 2025. The average cost to replace one skilled worker is $10,000–$125,000 depending on role and tenure. You can't fix a structural problem with a local solution — and you can't wait it out.

The operators gaining ground right now aren't waiting for the labor market to improve. They're building hiring systems that work in spite of it. Sperry has the credentials, the reputation, and the community standing to be a genuinely attractive employer to the right candidates. The constraint is visibility and process — not desirability. That's fixable, and it's BOSSTORQUE territory.

Six things the best operators are doing differently — and what Sperry needs to build
01
Employer brand first
Top candidates research you before they apply. What do they find? Sperry's TCIA accreditation, ISA credentials, 35-year reputation, and community trust are genuinely differentiating to qualified arborists — but none of it shows up in a way that speaks to a candidate right now. The Q3 website refresh, LinkedIn content, April 3 video assets, and review generation all double as employer brand infrastructure at zero marginal cost. We're building it anyway — it just needs to be pointed at candidates too.
02
Automated recruiting
If your hiring process depends on you being available, you'll always lose the best candidates to someone with a system. Quo handles inbound applicant calls after hours. An automated applicant sequence captures information, sets timeline expectations, and keeps candidates warm through the process. The infrastructure is being built for customer leads — pointing it at recruiting is a configuration change, not a new project.
03
Fast, structured onboarding
Workers who have a bad first two weeks don't stay. The investment made to hire them disappears. Your 35 years of expertise captured in the Knowledge Vault — species identification, hazard assessment, safety protocols, customer communication playbooks — compresses onboarding from six months of shadowing to a structured program new hires can work through from Day 1. Faster time-to-productive means faster capacity growth and lower turnover from undertrained hires.
04
Real retention levers
Advancement tracks, ISA certification support, year-round work stability — these matter more than pay to a growing share of the workforce. Sperry's subscription program and PHC service line create year-round scheduling stability that seasonal removal-only shops can't offer. The Club and subscription model aren't just customer retention tools — they're retention tools for crew who need consistent hours to stay.
05
Upfront screening
Skills assessments and behavioral fit testing aren't overhead — they're the filter between a good hire and an expensive mistake. An ISA-certified arborist generating $250K+ in annual billable revenue justifies a structured screening process. One wrong hire at that level costs more than the entire screening investment. BOSSTORQUE builds the screening system; Sperry's operations team applies it consistently.
06
A bigger recruiting net
Two states away might have exactly who you need. A $5,000 relocation package beats a $50,000 turnover cycle. The right partner here is an industry-specialist recruiter with TCIA connections and Pacific Northwest compensation benchmarks — not a general staffing firm that doesn't know the difference between a climber and a groundsman. ISA-certified arborists in the Pacific Northwest command $28–$45/hour. If Sperry's compensation is below market, it will consistently lose the best candidates. Benchmarking and closing that gap is less expensive than the alternative.

This is consistent with who Sperry already is — not a new direction.

Sperry Tree Care is a family-owned, values-driven company. Environmental stewardship, community trust, and genuine respect for the people who do the work are not marketing language — they are how you have run this business for 35 years. The McKenzie River Trust partnership, the longstanding KLCC sponsorship, the interest in capturing institutional knowledge rather than replacing experienced staff — these are expressions of the same culture.

A strong recruiting and hiring program is the operational expression of those values. Paying competitive wages, building structured onboarding so new crew members feel prepared rather than thrown in, offering ISA certification support and advancement tracks, creating year-round scheduling stability through subscription programs — these aren't just tactics to reduce turnover. They're what it looks like to genuinely respect the people who climb trees for a living in all weather, with a chainsaw, fifty feet off the ground.

You already know this. What's been missing is the system to operationalize it — and the digital infrastructure to make Sperry visible to the candidates who would thrive in that culture. That's the gap this initiative closes.

The connection to everything else on this roadmap

Subscription programs need crew to deliver scheduled visits. PHC service lines need licensed applicators. Geographic expansion into Douglas and Linn Counties needs local crew presence or commutable range. Acquisitions sometimes come with crew — but not always. Every growth scenario on this roadmap answers the same question: do we have the people to do the work? Building the hiring system now means Sperry can say yes to opportunity instead of turning down booked jobs because the crew isn't there.

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Section 11 · Business
Financing the Engagement
You are evaluating three paths. Jason covers factoring cost. The goal is to capture the opportunity window without waiting for perfect conditions.

Option A — Cash

Pay from operating cash flow. Simplest structure, no fees, no debt. Best if spring revenue is strong. Recommended if AR collections are solid entering peak season.

Option B — Factoring

Sell outstanding invoices at a small discount (2–5%) for immediate cash. Jason absorbs the factoring fee — Sperry receives full invoice value. Fastest path to liquidity without debt.

Option C — Loan

Business line of credit or SBA loan. Lower cost than factoring over time. Best for larger boosts where ROI payback justifies carrying cost. Less flexible than factoring for immediate cash needs.

Recommendation

Start with factoring for Q2 SOW liquidity, then transition to cash as campaigns generate return. The engagement should be self-funding within 90–120 days of full Q2 execution — the Spring Pruning campaign's $72K–$132K revenue influence and Meta Q2's $25K–$32K direct revenue cover the $17,000 SOW investment several times over. Don't let financing be the reason the window closes.

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Reference
Terms & Definitions
Acronyms, financial terms, and marketing terminology used in this document.
Financial Terms
TermDefinition
EBITDAEarnings Before Interest, Taxes, Depreciation, and Amortization. A standard measure of business profitability and the basis for valuation multiples (e.g., 5× EBITDA means the business sells for 5 times its annual EBITDA).
CM / Contribution MarginRevenue minus variable costs (labor, materials, direct costs). Distinct from net profit margin, which also deducts fixed overhead. Used here as the basis for the performance fee measurement.
Net Profit MarginWhat's left after all costs — labor, equipment, overhead, insurance, taxes — as a percentage of revenue. Sperry's current margin is approximately 8.5%. Industry "outstanding" benchmark is 20%.
LTVLifetime Value. Total revenue a customer has generated over their entire relationship with Sperry. B5 Sweet Spot average LTV: $7,102.
RFMRecency, Frequency, Monetary. A segmentation model that scores customers by how recently they purchased, how often they purchase, and how much they spend. Used to prioritize which contacts to target first.
ROIReturn on Investment. Revenue generated divided by cost invested. The Tree Care Club campaign cost $8,346 and projects $876K–$1.38M in revenue influence — 23×–83× ROI.
PHCPlant Health Care. Scheduled, proactive tree and shrub treatments: fertilization, soil aeration, pest/disease management, deep root feeding. Margins typically 30–50% — the highest-margin service line in tree care.
Operating LeverageThe margin improvement that results from spreading fixed costs across more revenue. As Sperry grows revenue, costs like insurance and management overhead don't grow proportionally — so margin improves automatically.
Tree Care Industry Terms
TermDefinition
ISAInternational Society of Arboriculture. The industry's primary certification body. ISA Certified Arborist is the professional credential that signals trained, accountable tree care expertise.
TCIATree Care Industry Association. The industry trade organization. TCIA Accreditation (held by Sperry) is the highest recognition for safety, ethics, and professionalism in tree care operations.
TRAQTree Risk Assessment Qualification. An ISA credential for certified risk assessment of trees — used by Alby and others on the Sperry team.
ASCAAmerican Society of Consulting Arborists. A separate professional designation for arborists who provide expert consulting, appraisal, and legal testimony services.
PHC Applicator LicenseState-required license to apply pesticides, herbicides, and certain soil treatments commercially. Required to deliver advanced PHC service tiers.
Marketing & Digital Terms
TermDefinition
CPLCost Per Lead. Total ad spend divided by number of leads generated. Target CPL for Sperry's Meta campaigns: under $70. Lower CPL = more leads for the same budget.
CTACall to Action. The specific action you're asking a reader to take — "Request a Free Estimate," "Join the Club," "Book Now." Every email and ad has one primary CTA.
A/B TestTesting two versions of something (subject line, ad creative, CTA) simultaneously to see which performs better. Runs continuously through Q2 Meta campaign to improve results over time.
Open RatePercentage of recipients who opened an email. Sperry's campaign open rate is 48.7%. Industry average for service businesses: 22–29%.
Conversion RatePercentage of contacts who took the desired action (joined the Club). Sperry's campaign conversion: 10.15%. Industry average for re-engagement campaigns: 1–3%.
Lookalike AudienceA Meta ad targeting feature that finds new people who share characteristics with an existing high-value group (e.g., B5 Sweet Spot customers). Used to find new leads who look like Sperry's best customers.
RetargetingShowing ads specifically to people who have already visited Sperry's website or engaged with prior ads. Higher intent audience = lower CPL and higher conversion rate than cold outreach.
Meta Pixel / Conversions APICode installed on Sperry's website that tracks visitor behavior and reports back to Meta — enabling accurate ad targeting and measurement. Installed as part of Workstream 1 security sprint.
GA4Google Analytics 4. Website tracking platform that measures traffic sources, page views, and conversion events (estimate requests, Club signups). Installed alongside the Meta Pixel in Workstream 1.
TCR RegistrationThe Carrier Registry — a one-time registration (~$20–25) required before businesses can send SMS marketing messages via US mobile carriers. Required to activate Sperry's 307 opt-ins.
Sequence / AutomationA series of emails or messages sent automatically based on a trigger (e.g., joining the Club, submitting an estimate request). Works 24/7 without manual intervention once built.
Kit (ConvertKit)Sperry's email marketing platform. Handles Club member sequences, campaign broadcasts, segmentation (residential vs. commercial), and automation triggers connected to Jobber.
ZapierAutomation tool that connects Sperry's platforms. Current live Zap: website form submission → Kit tag → Jobber estimate creation, automatically and instantly.
SOWStatement of Work. A formal agreement defining project scope, deliverables, timeline, and fees. The current document on the table is SOW BT-STC-Q2-2026.
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