Target: the MRR ladder in WHAT-TO-DO-AND-AVOID.md. The realistic range is $1k–5k MRR by month 24. Tier B ($20k+) is a ~1–3% outcome.
Rule: nothing in a later phase starts until the current phase's gate is hit. Gates and pivot rules are in WHAT-TO-DO-AND-AVOID.md. The detail for days 1–90 is in 08-90-day-plan.md.
Gate figures are shown as ~15 hrs/week / full-time.
Phase 1: Prove the pain (Months 0–3) → Gates G1, G2
| Track | Work |
|---|
| Customers | 10–15 buyer calls. 3–5 paid concierge pilots of the question window. |
| Product | Teams v1: anonymous post and reply, moderation queue, upvotes, question window, ranked host view, answers posted back. No identity stored. |
| Platform | Partner Center, publisher verification, SaaS offer linked to the app, Store submission. |
| Distribution | "How anonymity works" page, IT security one-pager, 4 exact-search guides, 10 Microsoft Q&A answers. |
| Pricing | Team $29 / Business $79 / Organisation $199 per month. Annual at 10× monthly. Pilots get founding pricing locked for 12 months. |
| Exit | 3 / 5 paying organisations, Store submission accepted, ≥2 question windows each |
Phase 2: Make the Store work (Months 4–6) → Gate G3
| Track | Work |
|---|
| Product | Anonymous polls, recurring schedule, minimum-anonymity threshold, retention setting, monthly admin summary email. |
| Platform | Publisher attestation. A request-template flow for users whose IT blocks the app. |
| Distribution | 8 guides live. Ask every organisation with 3 windows for a Store review. Contact 5 Microsoft 365 consultancies about referrals (20% recurring). |
| Metrics | Trials a month, IT approval rate, trial-to-paid, windows per organisation, source of each trial. |
| Exit | $500 / $1k MRR, ≥15% trial-to-paid, ≥50% IT approval within 14 days |
Phase 3: Renewal and depth (Months 7–12) → Gate G4
| Track | Work |
|---|
| Product | Answer archive tab, admin analytics (no identities), Excel/PowerPoint export, duplicate grouping (text similarity first). |
| Distribution | Double down on whichever source brings the most paying trials: Store, search or consultancies. |
| Ops | Help centre, templated replies, in-app onboarding. Target ≤1 ticket per 10 paying organisations a month. |
| Decision | If the Store brought under 30% of paying organisations, prepare the Slack port (pivot A). |
| Exit | $1.5k / $3k MRR, ≤3% monthly logo churn, 10 / 15+ reviews, ≥40% on annual |
Phase 4: Second surface or steady state (Months 13–24) → Gate G5
| Track | Work |
|---|
| Product | Slack port on the same backend, if G4 passed and ≥5 prospects asked for Slack. Plan for 10 active installs before review, a review of up to 10 weeks, the no-impersonation rule and the no-LLM-training rule. Translation for multinational tenants. |
| Platform | Microsoft 365 Certification only if a 2,000+ organisation will pay ≥$400/month for it. |
| Distribution | The best channel from months 1–12, plus the Slack Marketplace listing. |
| Checkpoint | Month 18: $2.5k / $5k MRR. Missing it means dropping the Slack port and running the Teams app on minimal hours. |
| Decision at month 24 | Above target with churn ≤3%: aim for $10k in year 3. $1–4k: run it on a few hours a month, or sell it (Acquire.com median 3.9× profit). Below $1k: stop. |
| Exit | $4k / $7k MRR, profitable |
Revenue path (illustrative, not a forecast)
| Month | Paying organisations (~15 hrs/week) | MRR (~15 hrs/week) | Paying organisations (full-time) | MRR (full-time) |
|---|
| 3 | 3 | ~$150 | 5 | ~$250 |
| 6 | 8 | ~$500 | 15 | ~$1k |
| 12 | 22 | ~$1.5k | 43 | ~$3k |
| 18 | 36 | ~$2.5k | 72 | ~$5k |
| 24 | 57 | ~$4k | 100 | ~$7k |
This assumes blended ARPU rising from ~$50 (pilots and small teams) to ~$70, monthly logo churn of ~3% after month 6, and at least 40% of new paying organisations from the Store and search. If churn runs above 5%, this path doesn't work. Fix renewal before adding the Slack port.
Budget guardrails (bootstrapped)
- Hosting, database, monitoring and tools below $100 a month until $2k MRR, and below 5% of revenue after.
- Zero paid acquisition before month 6. After it, only channels with payback under 3 months.
- Any AI feature must run under a no-retention agreement, with disclosure, and cost under 2% of revenue.
- No paid certification spend unless a signed buyer is waiting for it.