Build a roadmap

Harbor FY27 roadmap — planning-offsite proposal

Q4 2026–Q3 2027

Objective: Raise NRR from 104% to 112% through expansion in existing customers. Protect card continuity first, then deliver the best-supported expansion opportunities. Treat procurement as a gated investment—not a committed $6M forecast.

1. Roadmap

Planning assumptions

• Each existing squad has 11 squad-weeks per quarter, after support and on-call.
• Neither new squad is required to deliver this plan. Hiring is upside, not committed capacity.
• Numbers below are squad-weeks. Adoption work and reserves are timeboxed allocations, not additional feature estimates.
• Procurement production work proceeds only if the commercial gate below passes. Otherwise, its allocations go to expansion activation and remain available for replanning.

Delivery gates

Processor gate — non-negotiable - Allocate identifiable, independently executable migration work to Platform in Q4. - Complete migration code by early/mid-February, then freeze Harbor-side changes for the processor’s four-week certification. - Target cutover in mid-March, leaving contingency before 31 March. - If certification or implementation slips, pause card feature work and reallocate capacity immediately.

Procurement gate — decision by the end of Q4 Approve production funding only with: - Signed paid-pilot commitments at a validated price and requestor count—not general expressions of interest. - Evidence that customers with dedicated procurement tools will switch, or a clearly defined segment that does not require displacement. - A bottom-up expansion pipeline and pilot success criteria covering adoption, willingness to pay and implementation effort.

If the gate passes, the plan supplies the full estimate without hiring: 28 Approvals & Policy weeks + 3 Platform weeks at 1.5× = 30 equivalent weeks, plus 6 Integrations weeks. Target a Q3 launch, not a Q2 launch. If it fails or arrives late, do not start the full build; return to the exec team with revised scope and timing.

Outcome scorecard

Finance, Product and CS should maintain a monthly, existing-customer expansion bridge:

Do not count pipeline, enabled subsidiaries or estimated spend as realized NRR.

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2. The case for this plan

Why this order

First, protect the business we already have. Every card authorization depends on the retiring processor API, and interchange represents 58% of revenue. The migration is not an ordinary roadmap item. Tom’s allocation of 11 Cards weeks in Q4 leaves seven weeks in Q1, followed by four calendar weeks of certification. That is too little schedule margin once effective capacity and the certification freeze are considered.

Moving three Platform weeks into Q4 migration work produces two equivalent Cards weeks. Cards then has five implementation weeks remaining in Q1. This buys a realistic certification window and a cutover buffer. We should not schedule virtual cards into that buffer.

Next, pursue expansion with the strongest customer evidence. Multi-entity has nine written commitments among 14 requesting customers. The identified opportunity is $2.9M ARR across 52 subsidiaries, although that is a ceiling—not a forecast. We should validate pricing, rollout requirements and which subsidiaries are covered by the nine commitments before booking expected revenue.

Virtual cards address a substantial identified spend pool. At 1.1% net interchange, capturing all $410M of estimated software spend would generate approximately $4.5M annually. Capturing 25–50% would generate roughly $1.1M–$2.3M, before considering rollout timing. These are scenarios, not forecasts: the spend estimate is extrapolated, and invoice spend may not be readily cardable.

Virtual cards precede real-time controls because they offer a direct, measurable spend-capture opportunity. Controls follow to broaden CFO confidence and adoption. If customer testing shows controls are a prerequisite for moving software spend, we should reverse their order.

Retention and security are part of the expansion strategy. Intacct serves 17% of customers; its CSV cohort has materially higher gross revenue churn than the NetSuite cohort. That does not prove integration causes the difference, but it supports prioritizing Intacct over Dynamics. SSO/SCIM is relatively small and addresses security reviews at 11 existing accounts, as well as new-logo pipeline. Receipt matching similarly offers a bounded investment against a known support burden.

What changed from Tom’s draft

1. Removed assumed hiring capacity. Last year’s squads took five to eight months to reach a first full sprint and delivered roughly half capacity in their first quarter. Full-capacity squads in Q1 and Q2 are not a dependable planning assumption.

1. Made multi-entity delivery feasible. Its Platform estimate is 12 weeks, so it cannot fit wholly into an 11-week Q4. With migration assistance included, Platform delivers eight weeks in Q4 and four in Q1.

1. Gated procurement and moved any launch to Q3. Two of six design partners expressing willingness to pay is insufficient evidence for a full production commitment, particularly when four already have procurement tools.

At the proposed price, an average customer has about 70 requestors and generates $6,720 annually. Reaching $6M requires approximately 893 average-sized customers—81% of our current base. Larger customers or different packaging could change that calculation, but the prototype evidence does not support Tom’s forecast. A first-year ARR claim also should not be treated as revenue available by Q3.

1. Funded the mobile rewrite with the existing Expenses squad. It is necessary lifecycle work, not the leading NRR investment. Scheduling its 22 weeks across Q2 and Q3 meets the known support horizon without depending on a new squad.

1. Added explicit activation capacity. Shipping is not expansion. Subsidiary onboarding, integration migration and card-spend conversion require attention after launch.

What we are not doing

• Dynamics this year: only 3% of customers use it, versus 17% on Intacct; its new-logo evidence is also weaker.
• An unconditional procurement build or $6M revenue commitment.
• A Q2 procurement launch funded by unstaffed squads.
• New mobile feature scope beyond the rewrite.
• Filling every reserve with another launch. Remaining capacity is deliberately available for activation, technical uncertainty and measured opportunities.

Risks that could change the plan

Processor execution: Cross-squad assistance must be genuinely separable work. If it is not, the CTO must secure qualified help or displace other work immediately. Certification failure overrides all discretionary card work.

Commercial conversion: Written multi-entity intent is not a contract; estimated software spend is not captured spend. CS and Finance must validate both before treating them as the expansion bridge.

Procurement: Passing the commercial gate earns production funding, not a $6M forecast. Implementation complexity or weak paid-pilot adoption could still stop or narrow the investment.

Retention assumptions: Intacct’s churn association may reflect customer mix rather than integration quality. Measure adoption and renewal outcomes rather than assuming the six-point difference is recoverable.

NRR sufficiency: Moving from 104% to 112% represents roughly $6.9M of additional annualized cohort revenue against an $86M reference base, subject to Finance’s actual cohort calculation. The evidence does not yet prove this roadmap closes that gap. Before the offsite, Finance and CS should build a customer-level bridge covering expansion, contraction, churn and timing, without double-counting opportunities.

Hiring and technical estimates: Earlier hiring can accelerate a validated bottleneck. Estimate changes or a nearer mobile-support deadline can force reprioritization. Neither should quietly expand the committed scope.

Harbor FY27 roadmap: expand existing customers first

For the planning offsite | Q4 2026–Q3 2027

Recommendation: protect card continuity, unlock committed subsidiary expansion, then bring more existing-customer spend onto Harbor. Treat procurement as a commercial hypothesis to validate—not as committed revenue or a committed launch.

Board outcome: raise NRR from 104% to 112% by the end of Q3 2027. This roadmap supports that goal; the available evidence does not yet establish a credible revenue bridge all the way to 112%.

1. Proposed roadmap

Planning rules

• Commit against the five existing squads, each with 11 squad-weeks per quarter. Neither new squad is on the critical path.
• Numbers below are squad-weeks. Named feature estimates come from the pack; remaining capacity is an allocation ceiling for rollout, validation, hardening or contingency, not an estimate for additional features.
• Cross-squad delivery uses the stated 1.5× cost.
• Adoption work targets expansion and retention in existing accounts. It is not a placeholder for additional module builds.

Critical-path checks

• Processor migration: Q4 delivers 11 Cards weeks + 4 equivalent weeks from Expenses = 15. Q1 delivers the final 3, reaching the required 18. The February certification target creates margin before the hard retirement date.
• Certification freeze: no changes to the certified implementation during the four-week processor window. Before committing dates, confirm the precise freeze scope, book the processor slot and agree cutover acceptance criteria.
• Multi-entity: Approvals & Policy completes its 10 weeks in Q4; Platform completes 11 + 1. Therefore this is a Q1 launch, not a Q4 launch.
• Spend controls: Expenses spends 12 actual weeks across Q2–Q3 to deliver 8 Cards-equivalent weeks; Approvals & Policy supplies its 4 weeks in Q2. Work begins only after v2 is live.
• New squads: plan no committed output until teams are staffed and their ramp is observed. Use initial capacity for bounded adoption, testing or hardening work; allocate larger scope only after a delivery review.

Outcome scorecard

CS, Sales and Finance should turn these into named-account activation targets and a revenue bridge at the offsite. We should not invent conversion forecasts from the current pack.

2. The case for the plan

Why this order

First, protect the revenue engine. Every card authorisation uses an API retiring on 31 March, and interchange represents 58% of revenue. Tom’s migration occupies 18 of Cards’ 22 available weeks across Q4 and Q1, but must also leave four calendar weeks for certification. Quarterly capacity alone does not prove that schedule is safe.

Borrowing six Expenses weeks moves four Cards-equivalent weeks into Q4. That leaves only three planned migration weeks in Q1 and creates room for defects and certification. Receipt matching slips slightly; card continuity takes precedence.

Second, prioritise expansion with identifiable buyers. Multi-entity has the strongest evidence of a concrete expansion action: nine parents have committed in writing. The full 52-subsidiary opportunity is $2.9M ARR, but we cannot treat that total as committed or infer how many subsidiaries the nine parents represent. Launch in Q1, then sell and onboard—not merely ship.

Third, pursue spend expansion in parallel. Virtual cards have a direct connection to software spend currently outside Harbor. Controls address the most frequently expressed card need in the QBRs and may make finance teams comfortable moving more spend onto Harbor. Borrowing Expenses capacity costs four additional squad-weeks versus specialist delivery, but avoids serialising both products through Cards and supports an early-Q3 controls launch.

The $410M software-spend estimate implies a $4.51M annual net-interchange ceiling at 1.1%, before accounting for capture rates, timing or spend that cannot move from invoice to card. It is an opportunity, not a forecast. Both features may affect the same spend; we will not double-count it.

Fourth, remove retention and expansion friction. Intacct serves 17% of existing customers, versus 3% for Dynamics. The 13% versus 7% churn difference is an association, not proof the integration causes better retention, but it supports prioritising Intacct. SSO/SCIM is relatively small and addresses 11 existing-account security reviews. Receipt matching targets the largest expense support problem.

What changes from Tom’s draft

• Hiring no longer funds commitments. Historical time to the first full sprint was five to eight months, with half-capacity delivery in the first quarter. September approvals do not justify a full squad in Q1 and another in Q2. Further, new squads taking specialist work incur the stated transfer cost.
• Migration gains early borrowed capacity and an explicit certification window. Virtual cards no longer competes with the deadline in Q1.
• Multi-entity launches in Q1. Platform’s 12-week estimate exceeds one quarter’s 11-week capacity.
• Procurement moves from committed launch to commercial validation. Its revenue claim is not supported by current evidence.
• Controls gets borrowed delivery capacity. This creates an earlier adoption window without relying on hiring.
• Dynamics and the mobile rewrite leave the committed horizon. The freed capacity supports existing-customer outcomes and schedule resilience.

Why procurement is not the anchor

At the proposed price, an average customer has 70 requester seats and contributes:

70 × $8 × 12 = $6,720 ARR.

Reaching $6M ARR requires approximately 893 average-sized customers—81% of today’s customer base. Only two of six design partners said they would pay; neither is described as a signed commitment. Four already have a competing tool.

The estimated build is 30 Approvals & Policy weeks plus six Integrations weeks, before any additional cross-squad cost. That is too large a bet to anchor this year’s NRR target without stronger evidence.

Validation should seek paid commitments, actual seat counts and evidence of a differentiated switching reason. It is not an unbudgeted production build. A successful gate triggers an explicit investment decision, identifying displaced work and a capacity-backed launch date.

What we are not doing

We are not committing to procurement launch or its $6M claim, Dynamics, or a 22-week mobile rewrite in this horizon. We are also not inventing new feature scope to consume every available week.

The mobile support deadline remains real. By Q3, the CTO must establish the exact end-of-support date and a funded maintenance, upgrade or rewrite path. If continued safe operation requires starting earlier, it returns as a mandatory trade-off—not an assumed new-squad assignment.

Risks that could change the plan

The largest execution risks are processor certification availability, migration work that cannot be delegated, and underestimated multi-entity or controls complexity. Validate the processor work split immediately; any threat to certification displaces discretionary work first.

The largest commercial risk is insufficient expansion capture. At an illustrative $86M opening cohort, an eight-point NRR improvement represents $6.88M more retained/expanded ARR than a 104% outcome. Finance must reconcile the actual cohort and baseline. Even the full multi-entity and software-card opportunity totals only $7.41M before timing, conversion and overlap effects. This plan does not justify promising 112%.

Review the revenue bridge after Q1 launches. Weak activation should shift capacity toward removing proven adoption blockers. Strong paid procurement evidence, an earlier mobile security deadline, or demonstrated new-squad capacity can justify a replan—but none should silently become an assumption today.