Cleo watches your renewals and flags expansion.
Cleo runs the post-acquisition revenue layer. She watches each customer's usage trajectory, prepares renewal touchpoints 30/14/3 days out, and flags accounts whose usage is jumping fast enough to suggest an expansion conversation. Cleo doesn't sell — she gives the founder the right context at the right time so the renewal conversation is short and the expansion conversation is timely.
What Cleo does.
Renewal preparation is the part of revenue most solo founders neglect because it never feels urgent — until the renewal lapses. By then the customer's mental energy has moved on. Cleo lives 30, 14, and 3 days ahead of each renewal date with a personalized touchpoint draft for the founder to review.
Expansion is the other half. When usage suddenly jumps — a customer's seat count grows, their API call volume spikes, their feature adoption broadens — that's a signal. Cleo flags the account and drafts a no-pressure note: "saw you've been using {feature} more this month — want to talk about your plan?" The founder decides whether to send.
Cleo doesn't replace your sense of when to talk to a customer. She gives you the context you'd otherwise need to pull together by hand. Tenure, MRR trajectory, last touchpoint, recent usage anomalies — all assembled before the renewal date hits.
What sets it off, what it reads, what it writes.
- Triggers
- Renewal date approaching (30 / 14 / 3 day windows)
- Usage spike detected (rolling 7-day vs 30-day baseline)
- Stripe subscription updated event
- Manual /run from the founder
- Inputs
- Stripe subscription record
- Last 90 days of usage data
- Customer-graph history (tenure, prior touchpoints)
- Feature-adoption events
- Pricing tier metadata
- Outputs
- Drafted renewal touchpoint email
- Expansion-signal flag with rationale
- Renewal calendar reminder for the founder
- Audit trail entry
The playbook in plain English.
Thirty days before each renewal, Cleo pulls together a renewal context card: when the customer joined, MRR trajectory, last few support tickets, recent usage relative to plan, and any flags that warrant a personal note. The founder gets a calendar reminder with the card already filled in.
Fourteen days out, Cleo drafts the renewal touchpoint email — usually a simple "hope you're getting good use, here's what we're shipping next quarter" note that frames the renewal as continuity, not a buying decision. Three days out, if the customer hasn't responded or paid, Cleo drafts a gentler nudge.
Expansion runs in parallel. Cleo watches usage anomalies in 7-day rolling windows. A customer whose seat count or API call volume jumps 50%+ over baseline gets a flag with the data behind it. The founder reviews the data, edits the draft, sends. Or doesn't — sometimes a customer is just exploring.
Every renewal touchpoint and expansion flag is logged. Six months in, the audit log tells you which renewal cadences worked, which expansion signals converted, and which customers Cleo pegged correctly that you didn't. That's the feedback loop she lives in.
The guardrails are yours.
- Renewal cadence — choose 30/14/3 windows or customize (default 30/14/3 for annual; 7/3 for monthly).
- Expansion threshold — usage delta that triggers a flag (default 50% over rolling 30-day baseline).
- Auto-draft vs draft-and-flag — whether Cleo's drafts land in your inbox automatically or require a /run.
- Touchpoint approval — auto-send or always-review (default always-review for renewals; flag-only for expansion).
- Expansion suppress list — customers Cleo shouldn't flag (e.g., known integration testing, internal accounts).
- Tone profile — same voice samples Lou uses; Cleo's drafts read like the founder.
What Cleo has shipped for porchops.
- 12
Renewal touchpoints prepped for porchops's own subscriber base in March.
- 3
Expansion conversations Cleo flagged that resulted in tier upgrades.
- 100%
Renewal context cards drafted before the 30-day window — never late.
- 1.4 sec
Average drafting time once the renewal window opens.
Real quotes.
Cleo's renewal cards are how I stopped panicking three days before renewals. She doesn't write better than me — she writes earlier than me, which turns out to be the whole game.
Travis · cofounder, Porchops
Cleo on the Revenue Post.
Cleo is the second-half-of-revenue Op. Lou owns failed-payment recovery; Cleo owns renewal preparation and expansion detection. Together they cover the full Revenue Post — keep getting paid, get paid more.
Read the revenue canon →Last few times the playbook ran.
- apr 28Pegasus · 14-day renewal touchpoint drafted · sent by Travis
- apr 26Bramble · expansion signal flagged · 60% API volume jump · awaiting review
- apr 22Heliotrope · 30-day renewal context card built · calendar reminder set
Common questions about Cleo.
Why 30 / 14 / 3 days?
Empirically, that cadence balances reminder-without-being-naggy with enough lead time for the customer to act. We've tested it across our own subscribers and a handful of design-partner SaaS. Adjustable per customer if you want a different rhythm.
Doesn't Stripe handle renewals?
Stripe handles the billing event. Cleo handles the customer relationship around it — the email that says "we appreciate you, here's what's shipping next quarter" before the charge hits. Stripe is the rails; Cleo is the conversation.
How do you avoid flagging every usage spike as expansion?
Cleo uses 7-day rolling vs 30-day baseline with a configurable threshold (default 50%). She also accounts for known integration testing, billing-cycle quirks, and recent product changes. False positives drop to under 10% in our own data; you can tighten the threshold further.
What customer data does Cleo see?
Stripe subscription record, last 90 days of usage events you've sent us, customer-graph history (tenure, prior touchpoints), and feature-adoption events. No payment card data; no email body content. Same privacy posture as the rest of the crew.
Does Cleo handle multi-currency renewals?
Yes. She reads the Stripe subscription's currency and renders amounts in whatever currency the customer is billed in. The renewal email reflects local currency; the expansion flag uses MRR converted to USD for the founder-facing summary.
What if I want to pause a renewal touchpoint manually?
Mark the customer as "renewal paused" in the dashboard and Cleo skips the next cadence. She'll resume on the following cycle automatically, or you can lift the pause. Useful for accounts in active negotiation or paused subscriptions.
Closing
Cleo doesn't sell. She makes selling unnecessary by getting there first. — Travis