Run quarterly strategy sessions
Deliver a structured review every ninety days.
Airshow The Headliner
Charles
Business Strategist
Quarterly business reviews for service businesses that have outgrown the seat-of-the-pants stage. 90 days of data turned into a written strategic briefing and an AI strategist you can question line by line — no meeting to schedule.
What Charles does
Charles is the Airshow tier's strategist — the one Wingman whose whole job is to step back from the day-to-day and look at the business as a whole. Every 90 days, our backend pulls everything that happened in your account — every lead, every won deal, every lost one, every workflow, every dollar spent — and runs it through an AI analysis built around the metrics that matter for your trade. You get a written revenue-leak audit, a 90-day action plan with specific moves, and an interactive strategy session where you can ask Charles about any number, pressure-test any recommendation, and drill into the plan — on your own time, no meeting to book. It's quarterly strategic thinking, delivered by an AI that has already read your whole account cover to cover.
Capabilities
Built to do this every day.
01
Quarterly revenue-leak audit
We pull 90 days of leads, deals, calls, and conversations and identify where money is leaking out — quote-to-close drops, missed-call patterns, source ROI, dead-pipeline value. Delivered as a written briefing at the start of each quarter.
02
90-day action plan
Three to five specific, sequenced moves with owners and dates. Not 'do better marketing' — 'add a 48-hour quote-follow-up touch to Harper, expected to recover $X based on your Q1 close rate gap.'
03
Interactive AI strategy session
Open Charles any time and talk through the briefing — ask about any number, pressure-test a recommendation, or drill into the action plan. It's the quarterly review without the meeting: the strategist has read your whole account and answers on demand, no scheduling.
04
Vertical-specific benchmarks
Your numbers compared against anonymized aggregates from other Growth Wingman customers in your trade. Plumbers benchmark against plumbers, salons against salons.
05
Cross-Wingman pattern review
Charles reviews how your other Wingmen are performing — Harper's conversion rate, Stella's review velocity, Reva's reactivation lift — and surfaces what to tune.
06
Mid-quarter progress check
Six weeks in, Charles re-reads your numbers, flags what's moved and what's stalled on the action plan, and emails you the pulse. Ask follow-up questions any time throughout the quarter.
On the job
Just a glimpse of what Charles handles.
Charles turns quarterly strategy from a half-day think-session into a steady, data-driven set of decisions about where to grow next.
Instead of running the business on instinct alone, you sit down each quarter to a clear read on what's working, what's not, and where the next dollar comes from.
You focus on running the shop and serving the customers. Charles handles the structured review, the recommendations, and the follow-through.
Pull last quarter's numbers
Surface revenue, jobs, and growth metrics by quarter.
Spot growth opportunities
Identify the services and segments to lean into.
Spot drag areas
Surface what's slowing the business down.
Recommend strategic moves
Name three concrete moves to make this quarter.
Build quarterly OKRs
Translate strategy into measurable goals.
Set quarterly checkpoints
Schedule the touchpoints that keep the plan moving.
Watch goal progress weekly
Track each goal each week and flag where it slips.
Flag execution stalls
Alert you when a goal hasn't moved in two weeks.
Review team capacity
Surface where the team is over-stretched.
Review fleet utilization
Track how each truck and tech is utilized.
Review margin by service
Show which services make money and which don't.
Show revenue mix
Reveal what share of revenue each service represents.
Segment customers by tier
Group customers by value, frequency, and lifetime spend.
Review customer concentration
Flag when one customer or segment dominates revenue.
Recommend strategic direction
Point to the channel or segment worth doubling down on.
Review market position
Show where you stand against local competitors.
Identify your moat
Name the things competitors can't easily copy.
Pitch new service lines
Suggest services adjacent to what you already offer.
Recommend expansion zones
Pinpoint geographic areas worth opening up.
Surface satisfaction trends
Show NPS and review trend lines quarterly.
Flag concentration risks
Surface dependencies that could hurt if they shift.
Run quarterly checklists
Walk through a structured review of every area.
Lock in next-quarter goals
Convert recommendations into specific commitments.
Draft the strategy brief
Write the quarterly brief in plain English.
Validate assumptions
Stress-test the assumptions behind each recommendation.
Forward decisions to you
Hand the final call on every recommendation to you.
Investigate metric drops
Drill down when a quarterly metric moves unexpectedly.
Send the quarterly brief
Email the recap and recommendations on day one of the quarter.
Send mid-quarter check-ins
Email a mid-quarter pulse on progress.
Track year-over-year performance
Compare this quarter to the same quarter last year.
Repeat what worked
Surface initiatives worth running again this quarter.
Flag execution blind spots
Catch goals that lack a clear owner or plan.
Translate numbers into stories
Explain metrics in language that's easy to act on.
Recommend hire-vs-train calls
Help decide when to add headcount or invest in the team.
Refine next-quarter language
Edit goals so they're specific and measurable.
Hold you to the plan
Send accountability nudges as deadlines approach.
Carry forward open items
Keep unfinished work visible into the next quarter.
Document each decision
Capture the why behind every strategic call.
Alert on strategy drift
Ping you when execution starts to drift from the plan.
In the field
Real scenarios.
First briefing after a strong quarter
You had your best quarter ever and you can't tell whether it was the new ad spend, the Wingmen, or just seasonality.
Charles's briefing isolates which channel drove the lift, what your unit economics actually look like at the new volume, and whether your team capacity can hold if you keep pushing. The action plan gets specific about the two or three things to double down on and the one thing to stop spending money on.
Year-three plateau
Revenue has been flat for two quarters running and you can feel the team starting to drift.
Charles audits the funnel end to end and finds the leak — usually quote-stage or no-show, sometimes a reactivation gap. The 90-day plan is a sequenced set of changes (often one new Wingman, one workflow tune, one operational fix) with a revenue recovery estimate per move so you know what to chase first.
Considering adding capacity
You're thinking about hiring a second tech / second chair / second crew and you're not sure if the demand is really there.
Charles pulls the trailing-90 demand-vs-capacity numbers, models the load if a new hire came on, and tells you straight whether you're under-capacity, at capacity, or chasing a spike. If the answer is 'hire,' you also get the workflow updates needed to route work to the new person.
What you'll connect
Integrations
Required connections need to be wired before Charles can fly. We'll guide you through every one during onboarding.
- ✓
Your Wingman dashboard (full read)
So we can pull every metric we need
- +
Stripe or QuickBooks Optional
Lets the audit work off actual revenue, not just won-deal value
- +
Google Business Profile Optional
For reputation + local SEO signals in the briefing
What gets deployed
Inside the build
When your estimate is accepted, our system automatically deploys these artifacts to your Wingman dashboard. No copy-paste, no manual setup.
- Quarterly data-pull worker that snapshots 90 days of your into a reporting bundle
- AI-generated revenue-leak briefing (PDF, written for the owner — not a dashboard dump)
- 90-day action plan document with sequenced moves, owners, and revenue impact estimates
- Interactive AI strategy session — ask Charles about any number or recommendation on demand, no scheduling
- Automated mid-quarter progress check (week 6) emailed to you
- Private channel (email or in-app chat) for ad-hoc owner questions throughout the quarter
Ideal for
Established service businesses doing $1M+ a year who've stopped growing by accident and want a structured, quarterly look at where the next dollar comes from.
FAQ
Common questions.
Is there a human in this, or is it all AI? +
It's all AI — that's the point. Charles reads your entire account cold and turns 90 days of data into a written briefing and a 90-day plan, then stays available to talk it through whenever you want. No scheduling, no waiting on a person, no hour-long call to sit through.
What's different from the standard tier Wingmen? +
Every other Wingman runs the day-to-day — answering, booking, following up. Charles steps back every 90 days and looks at the whole business: what's working, what's leaking, where the next dollar comes from. Same AI foundation, different altitude.
When do I get the briefing and plan? +
Your written briefing and 90-day action plan land within the first 5 business days of each quarter. The mid-quarter progress check lands around week 6. In between, Charles is available any time to question a number, test an idea, or check progress on the plan.
Can I ask Charles questions between quarters? +
Yes — that's the whole idea. The briefing is the starting point, not the entire product. Open Charles any time to drill into a number, pressure-test a recommendation, or see how the action plan is tracking.
Can I add Charles without running the rest of Growth Wingman? +
Technically yes, but it's worth less without the operational layer underneath. The audit is best when Harper, Stella, Reva and the rest are running — there's more data to read and the action plan can actually execute.
Pairs well with
Build a crew.
Harper
Sales Strategist
Texts every missed-call lead within 5 minutes. Runs a 5-step personalized chase that stops the second they book. Pings you the second a lead goes hot.
Learn about Harper →
Stella
Reputation Manager
Fires the review-request SMS at the perfect moment after every job, auto-replies to positives, and pings you in 5 minutes when a negative one lands.
Learn about Stella →
Ready to hire Charles?
Tell us about your business and we'll send a tailored proposal with Charles configured for your industry — within one business day.