💰 Windsor Sync
Windsor Keeler — VP Finance, Churn/Retention, Data. Updated: April 19, 2026
🎯 Windsor's 90-Day Mission: Churn dashboard. Monthly revenue report. Customer.io implementation. Surface problems proactively — don't wait to be asked. Brian needs to see real-time unit economics before Sam.ai launches in May. If the current business is bleeding, Windsor is the first to know and the first to raise the alarm.
🚨 Communication Gap (Apr 19): Windsor has been silent 35+ days as of early April. Engineering app scorecards unreviewed 20+ days. If this pattern continues, it needs to be addressed directly in the 1-on-1. Brian needs proactive weekly finance updates, not radio silence.
📊 Key Metrics Windsor Owns
-1.0%
MRR Growth (Feb)
Churn: -$933K · New: +$673K
$16.3M
Subscription ARR
32.6% to $50M goal
77%
Customers at $0 GMV
$485K MRR from $0 sellers
🔥 #1 Priority: Pricing Sprint + Annual Push
~20,700 customers at ≤$79/mo. Angle: "Go annual, your price is locked for 12 months no matter what happens with pricing." At 5% take rate = $1M+ in upfront cash. This is NOT a price increase — it's a lock-in with a price-stability promise.
Windsor's job: model the exact offer, the revenue impact, and the break-even. Sam Lemon executes the campaign once Brian greenlights.
This can launch THIS MONTH — completely independent from the full pricing overhaul.
❓ Model the annual push offer and bring Brian a recommendation this week.
New tiers: T0 ($99/yr), T1 ($99/mo), T2 ($199/mo), T3 ($499/mo+). Windsor + Zach own financial modeling. Brian makes the final call on features-per-tier + Sam.ai pricing relationship.
Critical constraint: Do NOT raise prices on existing customers until Sam.ai adds value to the equation. MRR is already declining — premature price hikes accelerate churn.
❓ How does the Sam.ai freemium tier interact with the new SamCart tiers? Model both together.
Before Sam.ai launches with a free tier, Brian needs to know what free costs per user per month and at what usage level they must upgrade for the economics to work. AI token costs are real — model the break-even.
Inputs needed: avg AI credits consumed per user/month (Justin has this), token cost per credit, projected free:paid conversion rate.
❓ This is needed BEFORE May soft launch. When can Brian see the model?
📉 #2 Priority: Stop the MRR Bleed
MRR is declining. 77% of paying customers have $0 sales. $485K MRR (51%) comes from customers doing nothing on the platform. Windsor needs to deliver:
1. Churn cohort analysis — who's leaving, when, and why
2. Retention by segment — which customer types stick?
3. Early warning system — flag at-risk accounts before they cancel
4. Monthly churn report — delivered proactively to Brian, not on request
❓ When can Brian expect the first churn cohort report?
🚀 Active Projects
Constant in-app promos to lower churn + drive ARPA. Blocked on PostHog/Snowflake connection. Windsor owns the data pipeline side — once connected, enables behavioral triggers for at-risk customers, upsell nudges, and dormant user reactivation.
❓ Status of PostHog/Snowflake connection? What's blocking it?
SamPay processing revenue is not in Metabase. Windsor estimates total revenue (sub + processing) is ~$30M ARR. Need Finance to surface this as a standalone Metabase card so Brian can see true revenue, not just subscriptions.
New 4-tier pricing: T0 ($99/yr CU), T1 ($99), T2 ($199), T3 ($499+). Windsor + Zach leading eng/finance modeling. Impact analysis on existing customer base needed before migration begins.
Before Sam.ai launches, Brian needs a unit economics model: AI token costs per user, break-even on free tier, LTV projections by plan tier. This determines whether freemium is viable or financial suicide.
❓ Brian needs this BEFORE May soft launch. Can Windsor model AI token costs?
📋 What Brian Needs from Windsor
Weekly Deliverables
1. Weekly MRR report — subscription + processing, by business unit (eCom, Typeset, CU)
2. Churn alert — any week where net MRR is negative, flag immediately
3. CAC/LTV by segment — break down by customer persona. Which customers are worth acquiring?
4. Sam.ai financial model — freemium viability, token cost projections, pricing scenarios
♟️ Backlog
Break down CAC and LTV by customer persona (Sarah/Mike/Victoria). Go all-in on the best segment.
Lock existing base + cash injection for Sam.ai. ~20,700 addressable customers ≤$79/mo. $1M+ projected at 5% take rate.
22+ days unreviewed. Need to unblock eng hiring pipeline — this is critical for Sam.ai velocity.