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.

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 Product Roadmap

Prepared by: Staff PM, Harbor For: Executive Team Review (CEO, CFO, CRO, CTO)

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Part 1: The FY27 Roadmap (Q4 2026 – Q3 2027)

Our roadmap is structured into horizons (Now, Next, Later) to account for squad capacity constraints, hiring lead times, and critical infrastructure dependencies. Every initiative directly maps to our core FY27 mandate: raising NRR from 104% to 112%.

NOW (Q4 2026)

Focus: Mandatory infrastructure, unblocking enterprise sales security requirements, and protecting existing revenue.

• Cards Squad (11 squad-weeks):
• Processor v2 API Migration (11/18 sw used): Commencing the mandatory migration off the retiring v1 API.
• Platform Squad (11 squad-weeks):
• SSO and SCIM Provisioning (5 sw): Directly unblocks $1.2M in enterprise pipeline and clears 11 existing account security reviews (CRO request).
• Multi-Entity Foundation (6/12 sw used): Architectural groundwork for parent-subsidiary accounts.
• Integrations Squad (11 squad-weeks):
• Sage Intacct Integration (9 sw): Addresses our highest-churn segment (13% churn vs. 7% on NetSuite) and eliminates a major barrier in lost new-logo deals (31% of losses).
• Spillover buffer (2 sw).
• Expenses Squad (11 squad-weeks):
• Receipt-Matching Improvements (6 sw): Bumps auto-match above 71% to reduce the most common support ticket category.
• Mobile App Rewrite - Phase 1 (5/22 sw used): Early scoping and architecture on the CTO's supported framework upgrade.
• Approvals & Policy Squad (11 squad-weeks):
• Multi-Entity Approval Workflows (10 sw): Pairing with Platform to enable cross-subsidiary governance.
• Spillover buffer (1 sw).

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NEXT (Q1 2027)

Focus: Completing technical debt, launching high-value expansion modules, and integrating critical ERPs.

• Cards Squad (11 squad-weeks):
• Processor v2 API Migration - Completion (7/18 sw used): Finalising code before the March 31 deadline, entering the 4-week certification freeze.
• Virtual Cards for Software Subscriptions - Initiation (4/10 sw used).
• Integrations Squad (11 squad-weeks):
• Microsoft Dynamics Integration (12 sw adjusted to 11 sw capacity via minor scoping): Expanding our enterprise ERP footprint.
• Platform Squad (11 squad-weeks):
• Multi-Entity Support - Completion (6/12 sw used): Finalising multi-subsidiary entity structures.
• Expenses Squad (11 squad-weeks):
• Mobile App Rewrite - Phase 2 (11/22 sw used): Core feature porting and UI overhaul.
• New Squad A (Hired Dec 2026, delivering at ~50% capacity = ~5.5 sw):
• Procurement Module - Phase 1 (5.5/30 sw used): Setting up core purchase requests and initial approval logic.

(Note: During Q1, the card processor runs 4 weeks of certification testing. No changes can be deployed to card flows during this time).

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LATER (Q2 – Q3 2027)

Focus: Unlocking high-margin card spend, launching the flagship procurement add-on, and modernizing mobile infrastructure.

• Q2 2027 (Squads operating at full scale, plus New Squad B onboarding):
• Cards Squad: Virtual Cards for Software Subscriptions (6 sw remaining) & Real-time Spend Controls (8 sw).
• New Squad A (Procurement): Procurement Module - Phase 2 (18 sw total across Q2).
• Expenses Squad: Mobile App Rewrite - Phase 3 / Launch Preparation (11 sw remaining of 22).
• New Squad B (Hiring initiated Q1, arriving Q2, delivering ~5.5 sw): Deployed to accelerate Procurement integrations (Integrations/A&P support).

• Q3 2027 (Fully ramped capacity across 7 squads):
• Cards Squad: Real-time Spend Controls rollout and optimization.
• New Squad A & B: Procurement Module Launch, GA, and initial adoption drives.
• Expenses Squad: Mobile App GA (satisfying CTO's late-2027 framework deprecation timeline).
• Platform / A&P / Integrations: Cross-functional adoption loops for Procurement, Multi-Entity, and Dynamics/Intacct.

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Part 2: The Case for the Roadmap

1. Why This Order? (Balancing Reality and Ambition)

Our mandate is clear: raise NRR to 112% by the end of Q3 2027. To achieve this, we must unlock high-value expansion vectors (Procurement, Virtual Cards, Multi-Entity) while shoring up retention leaks (Sage Intacct churn, mobile app obsolescence, enterprise security blocks).

However, ambition must bow to physics. Tom’s draft roadmap contained a fatal flaw: it assumed new squads would ship code on day one and deliver 100% capacity immediately. Historical data at Harbor proves that newly approved squads take 5 to 8 months to reach their first full sprint and deliver roughly 50% capacity in their first quarter.

Furthermore, Tom’s draft scheduled the Procurement module to launch in Q2 2027 using a brand-new squad. Under realistic hiring timelines (approving the first squad in September means they only start shipping in earnest in Q1 at half-capacity), that timeline was impossible.

We have ordered this roadmap to respect three non-negotiable constraints: 1. The Card Processor Hard Deadline: On March 31, 2027, our processor kills the v1 API. If we do not finish the 18 squad-weeks of migration and the 4-week certification freeze by then, our card processing halts entirely—crushing 58% of our revenue. 2. Realistic Squad Ramp-Up: New Squad A (approved September) is phased in realistically for Q1 (delivering ~5.5 squad-weeks) and hits full stride in Q2. New Squad B is phased in for Q2. 3. Sequence of Dependencies: Virtual Cards and Real-time Spend Controls technically require the v2 API. Therefore, they cannot launch until Q2, immediately following the Q1 v2 migration and certification window.

2. What We Changed from Tom’s Draft and Why

• Shifted Procurement Timelines and Squad Allocation: Tom’s draft had New Squad A building and launching Procurement in Q1/Q2. Given historical hiring lags and the massive scope of Procurement (30 sw for Approvals & Policy + 6 sw for Integrations), we have stretched Procurement development across Q1 (New Squad A partial capacity) and Q2 (full capacity + New Squad B support), targeting a GA in Q3. Trying to rush it in Q2 would result in a broken launch or squad burn-out.
• Shifted Real-Time Spend Controls and Virtual Cards to Q2: Tom scheduled virtual cards in Q1. Because virtual cards and spend controls depend on the v2 API, and the processor locks us out for 4 weeks of certification testing during Q1, these items are now correctly sequenced for Q2 deployment, ensuring zero downtime risk.
• Brought Forward Enterprise Security & Retention Fixes (Q4): We moved SSO/SCIM, Sage Intacct, and receipt-matching improvements into Q4. Why? Because NRR isn't just about selling new modules; it's about stopping the bleeding. Sage Intacct users churn at nearly double the rate of NetSuite users (13% vs 7%), and Intacct blocks 31% of new-logo deals. Fixing this now preserves our base. Similarly, securing $1.2M in enterprise pipeline via SSO/SCIM in Q4 directly supports our growth goals without waiting for unproven modules.

3. What We Are Not Doing (And Why)

To protect focus and deliver on our NRR targets, we are explicitly declining or deferring several candidate items: * Alternative ERP Integrations (Beyond Intacct and Dynamics): While long-tail ERP requests exist, our data shows Intacct (17% of customers, high churn) and Dynamics (enterprise blocker) are the revenue levers that matter. Other ERPs are deferred to FY28. * Ad-Hoc Feature Requests from QBRs: While 26 out of 60 top customers asked for software virtual cards, we are delivering that. However, we are saying no to custom reporting suites and bespoke workflow builders requested by individual accounts until multi-entity and procurement are fully bedded down.

4. Risks That Could Change the Plan

1. Card Processor Certification Delays: * Risk: The processor’s 4-week certification window uncovers critical bugs on our side, forcing us to rewrite v2 migration code during the freeze. * Mitigation: We have front-loaded the 18 squad-weeks of migration work into Q4 and early Q1 to ensure we submit for certification well ahead of the March 31 hard stop. 2. Hiring Velocity for New Squads: * Risk: Tech talent market tightening could delay the onboarding of New Squad A and B engineers. * Mitigation: If hiring slips by a quarter, New Squad B’s intake is dropped, and the Procurement launch slips from late Q2 to mid-Q3. We would backfill critical path items by temporarily reallocating the Platform squad. 3. Procurement Adoption Skepticism: * Risk: Design partner feedback indicates that 4 out of 6 design partners already use dedicated procurement tools and need strong convincing to switch. Tom’s assumption of $6M ARR in Year 1 may be aggressive if attach rates lag. * Mitigation: At $8/user/month (impacting ~10% of employees at a 700-employee average customer = ~$6,700 ARR per customer), we need roughly 90 enterprise customers adopting it in Year 1 to hit the $6M target. Success hinges on Customer Success and Sales enablement, which begins in Q2 alongside build completion.