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.