Usable with a quick edit9 of 13 checks passed
The output is complete, evidence-based, and addresses the CEO's request; a product manager could use it with light wording adjustments, without re-checking facts or redoing the logic.
Output
Harbor Roadmap, Q4 2026 to Q3 2027
Q4 2026 (now)
| Squad | Work (squad-weeks) | Outcome it serves |
|---|---|---|
| Cards | Processor v2 migration (11 of 18) | Keeps every card authorisation running. Hard deadline: cut over before 31 Mar 2027. |
| Expenses | Receipt-matching (6); mobile rewrite starts (5) | Auto-match from 71% up; fewer expense tickets. Mobile rewrite ships before framework support ends. |
| Approvals & Policy | Multi-entity (10) | NRR: subsidiaries join existing accounts. |
| Platform | SSO/SCIM (5); multi-entity (6) | $1.2M enterprise pipeline; 11 accounts in security review. NRR via multi-entity. |
| Integrations | Sage Intacct (9) | Retention: Intacct customers churn at 13% vs 7% on NetSuite. Fewer lost new-logo deals. |
Q1 2027
| Squad | Work | Outcome it serves |
|---|---|---|
| Cards | Finish v2 (7; code-complete by 15 Feb). Processor certification (4 weeks, change freeze). Cut over before 31 Mar. Virtual cards start (4). | Authorisations protected. NRR: interchange on subscription spend. |
| Expenses | Mobile rewrite (11) | Mobile ships in Q3, ahead of late-2027 EOL. |
| Approvals & Policy | Real-time spend controls (4); procurement build (7) | Spend controls: 31 CFOs asked for them. Procurement: pricing gate at end of Q1. |
| Platform | Multi-entity finish (6); 5 sw held for onboarding and reliability | NRR: multi-entity GA. |
| Integrations | Procurement integration (6); Dynamics starts (5) | Procurement build. Dynamics is last in queue. |
| New squad A (Approvals & Policy home) | Onboarding; procurement build from ~half capacity | Procurement build. |
Q2 2027
| Squad | Work | Outcome it serves |
|---|---|---|
| Cards | Virtual cards (6); spend controls (5) | NRR: software subscription spend moves onto Harbor cards. |
| Expenses | Mobile rewrite (6 to finish); beta | Mobile feature-complete. |
| Approvals & Policy + new squad A | Procurement build (11 plus squad A at ~half) | Procurement build; design-partner beta prep. |
| Platform | Capacity held for multi-entity subsidiary onboarding | NRR: subsidiaries of the 14 requesting customers. |
| Integrations | Dynamics (7 to finish). Squad B onboarding. | Low-priority retention and new-logo coverage. |
Q3 2027
| Squad | Work | Outcome it serves |
|---|---|---|
| Cards | Spend controls (3); virtual cards hardening; 8 sw spare | NRR: spend controls and virtual cards at scale. |
| Expenses | Mobile launch | Mobile ships before EOL. |
| Approvals & Policy + new squad A | Procurement build complete (base case ~August); design-partner paid pilots (September) | Procurement: first paid pilots. Little or no FY27 ARR. |
| Platform | Multi-entity subsidiaries join | NRR. |
| Integrations | Dynamics complete; squad B at full capacity; next item chosen at Q3 review | Coverage. |
Later (Q4 2027 onward, gated): Procurement paid launch, only if the Q1 pricing gate is passed. Most procurement ARR lands in FY28.
---
The Case
The headline: 112% is not reachable in FY27
NRR is 104%. Reaching 112% by Q3 2027 means about $6.9M of additional net expansion ARR on our $86M base. My estimates for what this plan delivers inside the window:
- Multi-entity: $1.2–1.9M. The ceiling is $2.9M if all 52 subsidiaries join. Nine of 14 customers have committed in writing, which is not the same as signed.
- Virtual cards and spend controls: $0.4–0.7M. Interchange is 1.1%, so $410M of subscription spend is worth $4.5M at full capture. I assume 10–15% capture in-year. The $410M is extrapolated from 60 accounts.
- Intacct churn reduction: $0.4–0.9M. This assumes Intacct-using ARR is roughly 17% of the base (~$15M) and that the 6-point churn gap is caused by the CSV workflow, not by the customers themselves.
- Procurement: near zero.
That totals $2.0–3.5M, which takes NRR to roughly 106–108%. Procurement is the only item big enough to close the gap, and it cannot deliver inside FY27. Tom's note says procurement can add $6M in its first year. $6M is about 80% of the theoretical ceiling (1,100 customers × 70 requesters × $96 a year ≈ $7.4M), and only 2 of 6 design partners said they would pay. Even if the first-year number holds, the timing means it lands in FY28.
The board needs this correction before the offsite ends. Tom should brief the chair before the board sees a revised NRR path. I suggest we present 106–108% for FY27 with a path to 112% in FY28 and set out what would have to be true to close the gap.
Why this order
- Protect the base first. The v2 migration is the only hard deadline. Every card authorisation depends on it. Cards is planned with about two weeks of slack: migration complete by 15 Feb, 4 weeks of certification, cut-over by mid-March. The Cards squad is ring-fenced until cut-over, and I want a go/no-go on 15 Feb.
- Put the cheap, high-demand items first. SSO/SCIM is 5 squad-weeks and unlocks $1.2M of pipeline and 11 security reviews. Multi-entity is the largest in-year expansion lever and has written demand. Intacct is 9 squad-weeks against a 13% churn rate on 17% of customers.
- Use squads that exist. Expenses can build the mobile rewrite with its own capacity by Q2. That ships before the framework's late-2027 end of support without waiting for a new squad.
- Gate procurement. The build is 30 squad-weeks of Approvals & Policy work on a product where only a third of design partners have said they would pay. We build it, but the pricing decision comes at the end of Q1.
What I changed from Tom's draft, and why
| Tom's draft | Our plan | Why |
|---|---|---|
| New squad A: procurement from Q1; launch in Q2. | Procurement built by existing Approvals & Policy plus squad A; base-case build complete ~August; paid pilots in September. | 30 squad-weeks cannot be built and launched in Q2 by a squad that is still ramping. |
| New squads at full capacity from Q1 and Q2. | Modelled at half in their first quarter. | Last year's squads took 5–8 months to first full sprint and delivered half capacity in their first quarter. Tom's draft assumes about 55 squad-weeks from new squads in Q1–Q3. The realistic best case is about 44. |
| Mobile rewrite assigned to new squad B in Q2. | Mobile rewrite in Expenses from Q4; launch in Q3. | Expenses has the capacity now. Squad B is freed for Integrations. |
| Platform carries 12 squad-weeks of multi-entity in Q4 (above its 11 capacity); SSO in Q1. | SSO and 6 weeks of multi-entity in Q4; multi-entity finishes in Q1. | SSO moves forward to unlock $1.2M of pipeline. Multi-entity still reaches GA by end of Q1. |
| Dynamics in Q1. | Dynamics runs in spare Integrations capacity from Q1 to Q2, and is the first item to cut. | Dynamics is used by 3% of customers and was cited in 8% of lost deals. Intacct, at 17% of customers and 31% of lost deals, comes first. |
| Cards: finish migration in Q1 and start virtual cards. | Same sequence, with a 15 February checkpoint. | Tom's sequence was right. The checkpoint protects the certification window. |
What we're not doing
- Procurement at full scope before the Q1 pricing gate. If fewer than three of six design partners commit to a paid pilot at $8 per user, we cut scope and move capacity to other work.
- Dynamics as a committed FY27 item. It fits in spare capacity. It does not get priority over anything else.
- Mobile in a new squad. Expenses owns it.
- Platform-led procurement work. Platform has about 16 spare squad-weeks in Q1–Q2 and could absorb procurement sub-components at 1.5× cost if the gate passes. We don't plan that yet.
- Any NRR commitment above 108% for FY27 in board materials.
Risks that could change the plan
- The v2 migration slips past the certification window. This is the existential risk. If migration is not code-complete by about 22 February, we miss 31 March. Mitigations: ring-fence Cards from January, book a certification slot with the processor now, and agree a contingency with the processor in writing.
- New squads ramp slower than planned. Each month of delay pushes multi-entity onboarding, procurement and Dynamics later. Procurement is most exposed because Approvals & Policy is already at zero slack.
- Procurement demand is weaker than the evidence suggests. Two of six design partners would pay, and four already use a dedicated tool. The Q1 gate exists for this reason.
- Virtual card and interchange sizing is soft. The $410M is extrapolated from 60 accounts. Capture is an assumption.
- Intacct churn may not be caused by the CSV workflow. If the churn gap is about customer type rather than integration, the retention benefit is smaller.
- Multi-entity commitments are not contracts. Nine written commitments are real signals, but pricing for subsidiaries still needs to be set and sold.
- Mobile slips past Q3. Expenses has about 5 spare squad-weeks in Q2 and Q3 for launch fixes. A slip beyond Q3 puts us close to the framework's end of support.
Decisions needed at the offsite
- Approve the revised FY27 NRR range (106–108%) and agree how Tom briefs the board.
- Confirm the 15 February v2 checkpoint and the Cards ring-fence.
- Approve the procurement build with the Q1 pricing gate and a pre-agreed cut scope.
- Move mobile into Expenses and release squad B to Integrations.
Grades and run details
Decision model 69 · LLM judge 93
Decision model checks
- failUses the supplied evidence correctly9%
- passAddresses the actual decision92%
- partialRespects explicit constraints18%
- passIdentifies material uncertainty100%
- passAvoids unsupported claims19%
- passProduces the required deliverable53%
- partialProtects the processor deadline37%
- passPlans on the squads we actually have49%
- passMakes the call on procurement88%
- passOutcomes, with certainty that falls with distance86%
- failFits the stated capacity22%
- failSequences around dependencies33%
- passTells the story of the bets46%
Run
- Run
- #1
- API response time
- 1.8 min
- Submitted
- 8 Oct 2026