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FY27 Product Roadmap: Path to 112% NRR

To: Tom Achebe (CEO), CFO, CRO, CTO From: Staff PM Subject: Pre-read: Proposed Q4 2026 – Q3 2027 Product Roadmap

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1. The FY27 Roadmap (Q4 2026 – Q3 2027)

To hit 112% NRR by the end of Q3 2027, we need $6.88M in net expansion ARR (8% of our $86M base). Because expansion revenue only counts toward Q3 NRR if it is live, rolled out, and generating spend before the end of Q3, this roadmap front-loads our highest-conviction NRR drivers and protects our core card infrastructure.

Note on Capacity: Each existing squad has 11 squad-weeks (SW) per quarter. Cross-squad work incurs a 1.5× penalty (e.g., 4 SW of native work takes 6 SW for a borrowing squad). New squads are modeled using our historical hiring baselines: 6 months to onboard and 50% capacity (5.5 SW) in their first active quarter.

Q4 2026: Clear the Decks & Lock In Quick Wins

• Cards: Processor v2 Migration (11 of 18 SW). Outcome: Protect 58% of Harbor’s revenue ahead of the March 31 hard deadline.
• Approvals & Policy (A&P): Multi-Entity Support (10 of 10 SW). Outcome: Unlock $2.9M ARR subsidiary expansion pipeline.
• Platform: Multi-Entity Support (11 of 12 SW). Outcome: Same as above; ships in week 1 of Q1.
• Integrations: Sage Intacct Integration (9 of 9 SW). Outcome: Slash gross churn from 13% to ~7% across 17% of our customer base (~$880k ARR saved) and remove the blocker in 31% of lost new-logo deals.
• Expenses: Receipt-Matching Improvements (6 of 6 SW); begin Mobile App Rewrite (5 of 22 SW). Outcome: Cut our #1 support ticket driver to free up engineering on-call capacity; start retiring late-2027 mobile framework debt.

Q1 2027: Cutover v2 & Launch Multi-Entity

• Cards: Finish Processor v2 Migration (3 SW in Weeks 1–3), Freeze for Certification (Weeks 4–7), Cutover (Week 8). Start Virtual Cards for SaaS (8 of 10 SW, built on v2 environment). Outcome: Zero card downtime on March 31; pull Virtual Cards launch into early Q2.
• A&P: Assist Cards on Processor v2 Migration (6 SW = 4 native Cards SW in Weeks 1–6); Real-Time Spend Controls (4 of 4 native SW). Outcome: Crucial cross-squad assist ensures Cards hits the Feb 1 code freeze for v2 certification.
• Platform: Finish Multi-Entity (1 of 12 SW); SSO & SCIM Provisioning (5 of 5 SW); Multi-Entity customer onboarding & scale hardening (5 SW). Outcome: Ship Multi-Entity in January for immediate CS expansion selling; unlock $1.2M new-logo pipeline and protect 11 enterprise renewals.
• Integrations: Microsoft Dynamics Integration (11 of 12 SW). Outcome: Retain the 3% of base on Dynamics and remove the 8% new-logo blocker.
• Expenses: Mobile App Rewrite (11 of 22 SW). Outcome: Hit 73% completion on mobile debt retirement without hiring dependencies.

Q2 2027: Capture the $410M Card Spend Opportunity

• Cards: Finish Virtual Cards for SaaS (2 of 10 SW—Ships April); Real-Time Spend Controls (8 of 8 SW—Ships June). Outcome: Capture share of the $410M in off-Harbor software spend ($4.5M total interchange pool) requested by 43% of top customers; give 52% of top CFOs the point-of-sale controls needed to move remaining company spend to Harbor.
• A&P: Spend Controls integration support & policy templates (4 SW); Discovery & v2 Architecture for Light Vendor/PO Workflows (7 SW). Outcome: Ensure rapid adoption of Spend Controls; re-architect our procurement approach (see The Case below).
• Integrations: Finish Dynamics (1 of 12 SW); ERP syncing for Virtual Cards & Multi-Entity (10 SW). Outcome: Ensure seamless reconciliation for expanded multi-entity and SaaS card spend.
• Platform: Card spend limit notifications, alerting & multi-entity RBAC (11 SW). Outcome: Drive self-serve adoption of Virtual Cards across existing accounts.
• Expenses: Finish Mobile App Rewrite (6 of 22 SW—Ships May); Card spend receipt automation (5 SW). Outcome: Retire framework support risk 6 months ahead of CTO deadline.
• New Squad A (Ramping: 5.5 SW): Build self-serve migration tools for recurring SaaS bills to Virtual Cards. Outcome: Accelerate time-to-interchange for Virtual Cards.

Q3 2027: Drive Adoption to Lock In 112% NRR

• Cards & Platform: Automated SaaS vendor detection (flagging invoice spend in ERP to convert to Virtual Cards) & card limit auto-top-ups. Outcome: Maximize interchange realization before Q3 closes.
• A&P, New Squad A (11 SW) & New Squad B (5.5 SW): Build redesigned intake-to-card workflows (issuing single-use PO virtual cards upon approval). Outcome: Monetize approval workflows via interchange and seat expansion rather than competing head-on with entrenched procurement suites.
• Integrations & Expenses: In-app onboarding and bulk-provisioning tooling for Multi-Entity subsidiaries. Outcome: Help CS close the remaining 52 subsidiaries before EOY.

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2. The Case for This Roadmap

Why This Order? (The Math to 112% NRR)

To add $6.88M in net ARR by the end of Q3 2027, we must prioritize high-margin revenue protection and high-velocity expansion that can land in H1 2027: 1. Stop the bleeding via Intacct & SSO (+$0.9M to $1.1M ARR retained): NRR is a net number; every dollar of churn avoided is a dollar of expansion we don't have to sell. 17% of our base (~$14.6M ARR) uses Intacct via CSV and churns at 13% vs. 7% for NetSuite. Fixing this in Q4 saves ~$880k/yr in gross churn and unlocks 31% of lost deals. Pairing this with SSO/SCIM in Q1 secures 11 enterprise accounts under security review. 2. Ship Multi-Entity in week 1 of Q1 (+$1.8M to $2.9M ARR): 9 top customers have committed in writing to add subsidiaries once live. Sizing all 52 subsidiaries in the top-60 cohort equals $2.9M ARR—and more exist across our other 1,040 customers. Shipping in January gives CS three full quarters to close and onboard these entities. 3. Unleash Card Spend in Q2 (+$2.5M to $3.5M ARR): Our customers spend $410M/yr on software off-Harbor. At 1.1% net interchange, that is a $4.51M high-margin revenue pool sitting inside our existing base. Nearly half (26 of 60) of our largest accounts are actively asking for Virtual Cards for subscriptions, and 31 CFOs want Real-Time Spend Controls. Unlike new modules that require procurement cycles and legal sign-off, turning on virtual cards for existing customers generates interchange revenue the day a card is swiped.

Combined with our baseline 104% NRR ($3.44M), capturing just half of our conservative targets across these three pillars puts us at 112.5% NRR ($96.8M ARR) by Q3.

What Changed from Tom’s Draft—and Why

1. Resolving the March 31 Card Processor Crisis Tom’s draft had the Cards squad doing the 18-SW v2 migration across Q4 and Q1. However, Cards only has 11 SW per quarter. Furthermore, the processor requires a 4-week certification freeze before the March 31 cutover. To cut over by March 31, code must be finished by February 26 (Week 8 of Q1). In 19 weeks of calendar time, the Cards squad only has ~17.5 SW of capacity—leaving zero margin for error and pushing Virtual Cards into late Q2/Q3. * The Fix: In Q1, Approvals & Policy gives 6 SW of capacity (yielding 4 native SW at the 1.5× cross-squad rate) to the Cards team. This finishes all 18 SW of v2 code by the end of January, allowing certification in February, safe cutover in early March, and pulling Virtual Cards forward by 6 weeks.

2. Replacing the $6M Procurement Bet with Card Expansion Tom’s draft relies on Procurement to add $6M ARR in year one. The customer and capacity math does not support this: * The Revenue Math: At $8/month ($96/yr) for the 10% of employees who raise purchase requests (70 users per average 700-person customer), 100% adoption across all 1,100 customers would only generate $7.39M ARR. To hit $6M in Year 1, we would have to sell an unbuilt add-on to 81% of our entire customer base in two quarters. Yet in our design partner trial, 4 of 6 customers already had a procurement tool and refused to switch, and only 2 (33%) were willing to pay. Realistic Year-1 ARR is ~$500k–$900k. * The Capacity Math: Procurement requires 30 SW from A&P and 6 SW from Integrations. Tom assigned this to "New Squad A" starting in Q1. Last year, our new squads took 5 to 8 months to reach their first sprint, and delivered 50% capacity in their first quarter. Approved in September, Squad A won't run a sprint until Q2 2027 (delivering ~5.5 SW), and as a brand-new squad working in A&P's domain, they face the 1.5× ramp penalty. Assigned to Squad A, a 36-SW Procurement module would not ship until Q1 2028—contributing $0 to FY27 NRR.

3. De-risking the Mobile App Rewrite Tom assigned the 22-SW Mobile Rewrite to "New Squad B" in Q2. Approved in September, Squad B likely won't start until Q3 2027 at half capacity (5.5 SW), missing the CTO’s late-2027 framework end-of-life deadline. By keeping our existing Expenses squad on Mobile starting in Q4 (after a 6-SW sprint on Receipt Matching), we complete the rewrite in Q2 2027 with zero hiring dependency.

What We Are Not Doing

• We are not building a standalone, 36-SW Procurement Module in H1. We cannot justify starving Multi-Entity and Spend Controls to build a module that 67% of design partners rejected and that cannot ship in time to impact FY27 NRR. Instead, in Q2/Q3, we will explore lightweight PO-to-Virtual-Card workflows that drive card spend rather than competing with Coupa or Zip.
• We are not counting on un-hired squads for critical-path H1 deliverables. New Squads A and B are scheduled for Q2 and Q3 respectively, focused on adoption tooling and H2 expansion where hiring delays won't threaten our board target or infrastructure deadlines.

Key Risks That Could Change This Plan

1. Processor v2 Certification Rejections: If the processor finds bugs during the 4-week February certification window, our freeze extends and delays Virtual Cards. Mitigation: By using A&P to help finish the build in January, we buy a 4-week buffer before the March 31 cliff.
2. Cross-Squad Ramp Friction: Having A&P take on 4 SW of Cards work (costing 6 SW) in Q1 requires clean work partitioning. Mitigation: Cards will own the core v2 authorization webhooks; A&P will own isolated migration scripts and fallback testing.
3. Slower Multi-Entity Sales Cycles: While 9 accounts gave written intent, parent-subsidiary contract addendums can stall in legal. Mitigation: CS and Finance must pre-negotiate subsidiary pricing addendums with the 14 target accounts in Q4 so we can bill immediately upon the January release.

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 — Q4 2026 to Q3 2027

Planning basis: Each existing squad has about 11 roadmap squad-weeks per quarter. Figures below are the candidate-work estimates; capacity not assigned to a feature is deliberately held for launch, customer activation, fixes and contingency. New squads are not counted at full capacity until their ramp is proven.

New Squads A and B: Plan for onboarding and ramp, not full feature capacity. When productive, use them for bounded rollout, quality or activation work. No committed launch depends on their availability.

Case for the plan

Why this order

The board’s priority is to move NRR from 104% to 112% by the end of Q3, primarily through expansion in existing customers. The plan therefore favors credible opportunities to retain customers or deepen their use of Harbor, while keeping some room for new-logo needs.

First, v2 is a hard dependency and a hard deadline. All authorisations still run through v1, which retires on 31 March. The 18 Cards squad-weeks consume 11 weeks in Q4 and seven in Q1. That leaves time to finish implementation before the processor’s four-week certification and to keep the required freeze during testing. Virtual cards and real-time controls must wait until certification is complete.

Next, multi-entity has concrete expansion evidence: 14 of the 60 largest customers asked, and nine have said in writing that they would add subsidiaries. The $2.9M ARR estimate assumes all 52 subsidiaries join, so it is an upside case, not a commitment. Completing the Platform and Approvals & Policy work across Q4 and Q1 creates a path to test that demand with real rollouts.

Virtual cards are the first post-migration Cards feature because 26 large customers asked for them and Finance estimates $410M of annual subscription spend is currently elsewhere. At Harbor’s 1.1% net interchange, full capture would represent about $4.5M in annual interchange revenue, but that is a ceiling, not a forecast: the spend estimate is extrapolated, and adoption and capture are unknown. Real-time controls follow, with coordinated work across Cards and Approvals & Policy. The 31 CFO requests are strong demand evidence, but the plan avoids trying to fit both features into Cards’ 11-week quarterly capacity.

Intacct comes before Dynamics. Intacct is used by 17% of customers through CSV, and those customers have higher observed gross revenue churn than customers on NetSuite. That comparison is correlational, but it supports addressing a retention risk. Dynamics has lower existing use (3%) and a more limited new-logo case, but the 8% of lost deals citing it justifies completing the 12-week integration after Intacct.

SSO/SCIM is a relatively small, five-week Platform investment tied to five enterprise deals representing $1.2M of pipeline and 11 existing security reviews. It supports commercial outcomes without displacing the larger expansion bets.

What changed from Tom’s draft

• Removed procurement from committed build and launch. Six design partners are not enough evidence for the board’s $6M first-year ARR claim: only two said they would pay, and four already use another tool. At the proposed price, an average 700-employee customer would generate about $6,720 ARR if 10% of employees were buyers. Reaching $6M would require roughly 893 such customer equivalents. We should validate willingness to switch and pricing before committing 30 Approvals & Policy and six Integrations squad-weeks.
• Corrected the hiring assumption. Prior squads took five to eight months from approval to a first full sprint and delivered about half capacity in their first quarter. The plan does not count either new squad at full capacity in Q1 or Q2, or make a feature dependent on them.
• Made the v2 critical path explicit. The migration spans Q4 and Q1, with implementation targeted ahead of March certification. Tom’s draft did not protect that freeze clearly enough.
• Sequenced Cards work to fit capacity. Virtual cards and real-time controls require 18 Cards squad-weeks together, more than one quarter’s 11-week capacity. They are sequenced across Q2 and Q3.
• Started the mobile rewrite with the existing Expenses squad. The work is 22 weeks, so starting in Q1 targets completion in Q2 without relying on an unproven new squad.

What we are not doing

We are not committing to build procurement, starting a mobile rewrite with a new squad at assumed full capacity, or taking on another major integration or platform feature in Q3 without evidence from the launches above. New-logo work remains in the plan, but expansion and retention come first.

Risks that could change the plan

• Processor timing: Any migration slip puts card authorisations at risk. Track delivery and certification weekly; protect the Q1 card schedule and do not pull dependent features forward.
• Expansion may not materialize: Multi-entity interest and card requests do not guarantee adoption or spend migration. Track subsidiary activation, card spend moved, and controls usage—not just releases.
• Commercial estimates are uncertain: The $2.9M multi-entity estimate and $4.5M card-spend ceiling are not forecasts. Procurement’s $6M claim is especially unsupported by current evidence.
• Mobile has little slack: The 22-week rewrite fills two quarters of Expenses capacity. Scope growth, delivery delays or an earlier-than-expected framework deadline would require replanning.
• Hiring, integration and cross-squad delivery may slip: Ramp timing is uncertain; the Intacct churn difference may not be caused by the integration; and spend controls depend on coordinated Cards and Approvals & Policy work.

This roadmap gives Harbor credible bets aligned to the NRR goal, but it does not establish that the 112% target is guaranteed. We should review expansion and retention indicators at each quarterly planning checkpoint and change the plan if customer evidence or delivery risk materially shifts.