Build a roadmap

Harbor Roadmap, Q4 2026 to Q3 2027

Pre-read for the planning offsite. Prepared from Tom's draft.

Part 1: The roadmap

Planning assumptions - Each existing squad has 11 squad-weeks of roadmap capacity a quarter. Work done in another squad's area costs 1.5×. - The two new squads are planned at the dates our history supports, not the approved dates. Last year's squads took 5 to 8 months from approval to their first full sprint. - Squad A: 0 weeks in Q1, about 5 in Q2 (half capacity), about 11 in Q3. - Squad B: 0 weeks in Q2, about 5 in Q3. - Nothing committed depends on either new squad. - The fiscal year runs Q4 2026 (Oct to Dec) through Q3 2027 (Jul to Sep).

Squad plan by quarter (squad-weeks in brackets)

Items, outcomes and key dates

NRR bridge: what this plan plausibly delivers by end of Q3 2027

Moving NRR from 104% to 112% needs about $6.9M of additional net expansion (8 points of $86M).

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Part 2: The case for it

The short version

Tom's draft has the right ingredients. It does, however, have three problems:

1. No buffer on the processor deadline. The migration has no room to slip against a date that could stop every card authorisation.
2. Key work sits on squads we won't have. Procurement and the mobile rewrite depend on new squads that history says won't exist at full capacity until Q3 at the earliest.
3. Procurement can't carry the goal. It is expected to deliver the NRR target, but the evidence doesn't support $6M and the timing puts almost none of it inside the measurement window.

This plan protects the deadline first. It then sequences the levers with the strongest evidence so they land early enough to count. Even so, product alone likely gets us to 107% to 110%, not 112%. The exec team should know that now, not in Q3.

Why this order

1. The processor migration comes first, with buffer.

Every authorisation runs through v1, so a missed cutover puts most of our revenue at risk. On Tom's draft: - Cards alone finishes the 18 weeks around late February. - The 4-week certification then ends in the last days of March. - That leaves under a week of slack, with December holidays not counted and no room for a failed certification.

Lending 5 Platform weeks in Q4 changes this: - Code complete moves to about 31 January. - Cutover lands around 1 March. - We have roughly four weeks of buffer.

This also means virtual cards can't "start in Q1" as the draft says. During certification nothing on our card stack can change. Cards will do design and sandbox work in Q1 and start production work after cutover.

2. Multi-entity and virtual cards next, because they have the best evidence and they land in time.

NRR is measured at the end of Q3, so anything launching after about June barely counts. Our two strongest levers are: - Multi-entity: 9 customers have committed in writing to add subsidiaries, which is about $1.5M to $2.9M. - Virtual cards: a $4.5M ceiling. 26 of our 60 largest customers asked for them.

Multi-entity ships in February. Virtual cards ship in May. Real-time spend controls follow in July because they share the Cards squad. They matter to 31 CFOs, but we haven't sized them.

3. Retention work runs in parallel, because it is cheap.

• Intacct: 9 weeks of work. It addresses a segment churning at nearly twice our NetSuite rate and appears in 31% of lost deals. The integration only reduces churn if customers actually move off CSV, so I added a Q1 migration push with CS.
• SSO and SCIM: 5 weeks of work. It protects 11 accounts and unblocks $1.2M of pipeline.

4. Procurement is real but gated, and it is not the FY27 lever.

What I changed from Tom's draft, and why

1. Migration buffer. Platform lends 5 weeks in Q4. The cost is that multi-entity moves from December to February. I think that trade is clearly right, because the downside of a missed cutover is existential.

2. New squads planned realistically. - Squads approved in September reach their first full sprint between February and May, based on last year's 5 to 8 months. - Each then runs at half capacity for a quarter. - Squad A realistically gives about 5 weeks in Q2. Squad B gives nothing before Q3. - I've kept every committed item on the existing five squads. The new squads are upside.

3. Procurement moved to Approvals & Policy and gated. - A&P owns the domain, has capacity after multi-entity, and was left without work in the draft. - Build starts in Q1. At the end of March we need signed paid-pilot commitments from about 10 customers beyond the two design partners, or we redirect A&P. - GA lands around September. If Squad A arrives on time, it accelerates the work.

4. The $6M procurement figure needs resetting with the board. - At $8 per user per month and 10% of our ~770,000 employees raising requests, the ceiling is about $7.4M a year if every customer adopts. $6M therefore implies about 81% adoption. - Only 2 of 6 design partners said they'd pay. The other four already use a dedicated tool. - At a one-in-three adoption rate, procurement is worth about $2.5M at full run-rate, reached over years, and less than $0.3M inside FY27. - I recommend Tom and the CFO correct this at the next board touchpoint, before the board starts tracking it.

5. Mobile rewrite moved to Expenses, starting in Q4. - Expenses owns the app and the draft left it idle after Q4. - The rewrite finishes by May, and the old app is retired by September. - This gives the CTO's deadline real margin. Leaving it on Squad B would risk missing it.

1. Spend controls now include the A&P work (4 weeks). The draft omitted this.

1. Dynamics moves from Q1 to May. The Intacct customer migration goes first, because Intacct matters roughly five times more by customer count and lost deals.

What we're not doing

• Not claiming procurement drives FY27 NRR. We are also not building past the March gate without paid commitments.
• Not starting virtual cards or anything else on the card stack before cutover.
• Not putting any deadline-critical or NRR-critical work on unhired squads.
• Not adding new-logo-only features beyond Intacct, Dynamics and SSO, which also serve retention. New logos come second this year, as the board set.
• Not filling the Q3 reserve on Platform and Integrations. That slack absorbs migration fallout, integration hardening and new-squad onboarding. If the migration goes cleanly, we can release it to card-spend adoption work at Q2 planning.

Risks that could change the plan

1. Certification fails or needs a second round. A re-run would consume the entire buffer. - Book the certification slot now. - Run a pre-certification dry run in January. - Ask the processor in writing for a contingency extension and an emergency-fix protocol for the freeze window. - If code complete slips past mid-February, pull more Platform capacity immediately.

2. The $410M software-spend figure is extrapolated from our 60 largest accounts. Smaller customers may put proportionally less software spend on cards. - In Q4, validate it with AP data from about 20 mid-sized customers. - If it halves, virtual cards is worth about $0.4M to $0.8M in window and spend controls rises in priority.

1. Multi-entity conversion comes in below the written commitments. CS should agree subsidiary onboarding plans with the 9 customers in Q1, before the feature ships.

1. Real-time spend controls sit on the authorisation path. A latency problem could cause false declines. Platform supports this work in Q3, and we should launch in stages.

1. Hiring slips further. This doesn't threaten committed dates, but procurement would stay in Q3 and our adoption capacity shrinks.

1. The procurement gate fails. A&P redirects to deeper spend controls and multi-entity policy features, both of which feed card spend.

1. The mobile framework end-of-support date is only "late 2027". The CTO should confirm the exact date.

Decisions we need at the offsite

1. Approve Platform's Q4 loan to Cards, accepting that multi-entity moves to February.
2. Agree the board message on procurement, and the gate criteria behind it.
3. Close the NRR gap. This plan lands about 107% to 110%. Closing the remaining $1.5M to $4M needs commercial levers the CRO and CFO own, such as CS-led card activation, packaging and pricing, and a multi-entity sales motion beyond the 9. Otherwise we tell the board now that 112% is a stretch.
4. Authorise the processor extension request.