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Harbor Roadmap, Q4 2026 to Q3 2027

Q4 2026 (now)

Q1 2027

Q2 2027

Q3 2027

Later (Q4 2027 onward, gated): Procurement paid launch, only if the Q1 pricing gate is passed. Most procurement ARR lands in FY28.

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The Case

The headline: 112% is not reachable in FY27

NRR is 104%. Reaching 112% by Q3 2027 means about $6.9M of additional net expansion ARR on our $86M base. My estimates for what this plan delivers inside the window:

• Multi-entity: $1.2–1.9M. The ceiling is $2.9M if all 52 subsidiaries join. Nine of 14 customers have committed in writing, which is not the same as signed.
• Virtual cards and spend controls: $0.4–0.7M. Interchange is 1.1%, so $410M of subscription spend is worth $4.5M at full capture. I assume 10–15% capture in-year. The $410M is extrapolated from 60 accounts.
• Intacct churn reduction: $0.4–0.9M. This assumes Intacct-using ARR is roughly 17% of the base (~$15M) and that the 6-point churn gap is caused by the CSV workflow, not by the customers themselves.
• Procurement: near zero.

That totals $2.0–3.5M, which takes NRR to roughly 106–108%. Procurement is the only item big enough to close the gap, and it cannot deliver inside FY27. Tom's note says procurement can add $6M in its first year. $6M is about 80% of the theoretical ceiling (1,100 customers × 70 requesters × $96 a year ≈ $7.4M), and only 2 of 6 design partners said they would pay. Even if the first-year number holds, the timing means it lands in FY28.

The board needs this correction before the offsite ends. Tom should brief the chair before the board sees a revised NRR path. I suggest we present 106–108% for FY27 with a path to 112% in FY28 and set out what would have to be true to close the gap.

Why this order

1. Protect the base first. The v2 migration is the only hard deadline. Every card authorisation depends on it. Cards is planned with about two weeks of slack: migration complete by 15 Feb, 4 weeks of certification, cut-over by mid-March. The Cards squad is ring-fenced until cut-over, and I want a go/no-go on 15 Feb.
2. Put the cheap, high-demand items first. SSO/SCIM is 5 squad-weeks and unlocks $1.2M of pipeline and 11 security reviews. Multi-entity is the largest in-year expansion lever and has written demand. Intacct is 9 squad-weeks against a 13% churn rate on 17% of customers.
3. Use squads that exist. Expenses can build the mobile rewrite with its own capacity by Q2. That ships before the framework's late-2027 end of support without waiting for a new squad.
4. Gate procurement. The build is 30 squad-weeks of Approvals & Policy work on a product where only a third of design partners have said they would pay. We build it, but the pricing decision comes at the end of Q1.

What I changed from Tom's draft, and why

What we're not doing

• Procurement at full scope before the Q1 pricing gate. If fewer than three of six design partners commit to a paid pilot at $8 per user, we cut scope and move capacity to other work.
• Dynamics as a committed FY27 item. It fits in spare capacity. It does not get priority over anything else.
• Mobile in a new squad. Expenses owns it.
• Platform-led procurement work. Platform has about 16 spare squad-weeks in Q1–Q2 and could absorb procurement sub-components at 1.5× cost if the gate passes. We don't plan that yet.
• Any NRR commitment above 108% for FY27 in board materials.

Risks that could change the plan

1. The v2 migration slips past the certification window. This is the existential risk. If migration is not code-complete by about 22 February, we miss 31 March. Mitigations: ring-fence Cards from January, book a certification slot with the processor now, and agree a contingency with the processor in writing.
2. New squads ramp slower than planned. Each month of delay pushes multi-entity onboarding, procurement and Dynamics later. Procurement is most exposed because Approvals & Policy is already at zero slack.
3. Procurement demand is weaker than the evidence suggests. Two of six design partners would pay, and four already use a dedicated tool. The Q1 gate exists for this reason.
4. Virtual card and interchange sizing is soft. The $410M is extrapolated from 60 accounts. Capture is an assumption.
5. Intacct churn may not be caused by the CSV workflow. If the churn gap is about customer type rather than integration, the retention benefit is smaller.
6. Multi-entity commitments are not contracts. Nine written commitments are real signals, but pricing for subsidiaries still needs to be set and sold.
7. Mobile slips past Q3. Expenses has about 5 spare squad-weeks in Q2 and Q3 for launch fixes. A slip beyond Q3 puts us close to the framework's end of support.

Decisions needed at the offsite

1. Approve the revised FY27 NRR range (106–108%) and agree how Tom briefs the board.
2. Confirm the 15 February v2 checkpoint and the Cards ring-fence.
3. Approve the procurement build with the Q1 pricing gate and a pre-agreed cut scope.
4. Move mobile into Expenses and release squad B to Integrations.

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.

Part 1: Product Roadmap (Q4 2026 – Q3 2027)

``` ==================================================================================================== SQUAD Q4 2026 Q1 2027 Q2 2027 Q3 2027 ==================================================================================================== Cards Processor v2 Migration Finish v2 (Wks 1-7) Virtual Cards for SaaS Real-Time Controls (11 wks) API Freeze/Cert (W8-11) (6 wks remaining) (Cards: 3 wks) Virtual Cards Prep Real-Time Controls Interchange Optimization (4 wks) (Cards: 5 wks) & Scaling (8 wks) ---------------------------------------------------------------------------------------------------- Platform Multi-Entity: Core Multi-Entity: Wrap-up Platform Scaling & Cross-Entity Reporting Data Architecture (1 wk) Org Hierarchies & Enterprise Admin (11 wks) SSO & SCIM (5 wks) (11 wks) (11 wks) Hardening (5 wks) ---------------------------------------------------------------------------------------------------- Approvals & Multi-Entity: Policy Multi-Entity: Release Real-Time Controls: Procurement Discovery Policy & Approval Routing (2 wks) Policy Engine (4 wks) & Scoping (MVP) (10 wks) A&P Rule Engine Complex Approval Rules (Approvals: 11 wks) Buffer (1 wk) Upgrades (9 wks) (7 wks) ---------------------------------------------------------------------------------------------------- Integrations Sage Intacct Native Sage Intacct GA (2 wks) MS Dynamics Integration MS Dynamics GA (3 wks) Integration MS Dynamics Integration (Integrations: 10 wks) ERP Webhooks & Custom (9 wks) + Buffer (2 wk) (Integrations: 2 wks) Sync (8 wks) ---------------------------------------------------------------------------------------------------- Expenses Receipt Auto-Match Mobile App Rewrite: Mobile App Rewrite: Mobile App GA & Optimization (6 wks) Phase 1 Core Workflows Phase 2 Parity/Release Expense Policy Polish Mobile Prep (5 wks) (11 wks) (11 wks) (11 wks) ---------------------------------------------------------------------------------------------------- New Squad A [Hiring / Onboarding] [Ramp / Training] Procurement Foundation Procurement Workflows (A&P Focus) (Ramped: ~5.5 wks) (Full capacity: 11 wks) ---------------------------------------------------------------------------------------------------- New Squad B [Hiring / Pipeline] [Hiring] [Onboarding / Ramp] Integrations / Core (Ecosystem Focus) (Ramped: ~5.5 wks) ==================================================================================================== ```

Squad-by-Squad Outcomes

• Cards:
• Processor v2 Migration: Protects 100% of Harbor’s card-authorisation volume ($49.9M existing ARR) against the hard 31 March 2027 processor shutoff; unlocks v2 capabilities required for virtual cards and real-time controls.
• Virtual Cards for Software Subscriptions: Captures existing customer SaaS spend currently paid via invoice/other cards ($410M addressable pool), directly driving interchange revenue to expand NRR.
• Real-Time Spend Controls: Enables 31 top-tier CFO accounts to enforce budgets at point-of-sale, unlocking enterprise card issuance and shifting unmanaged invoice spend to Harbor cards.
• Platform:
• Multi-Entity Architecture: Unlocks $2.9M contracted expansion ARR across 52 non-Harbor subsidiaries of top accounts.
• SSO & SCIM Provisioning: Unblocks $1.2M in enterprise pipeline and closes compliance gaps for 11 critical renewal accounts.
• Approvals & Policy:
• Multi-Entity Approvals: Delivers cross-subsidiary approval chains required to close existing multi-entity commitments.
• Real-Time Policy Engine: Co-delivers immediate POS budget validation with the Cards squad.
• Procurement Discovery & MVP Architecture: Reframes procurement around verified buyer demand without starving committed delivery.
• Integrations:
• Sage Intacct Integration: Halves the 13% annual churn rate of the 17% of Harbor customers on Intacct (retaining ~$875k ARR annually) and addresses Harbor's #1 new-logo loss reason (31% of lost deals).
• Microsoft Dynamics Integration: Expands ERP coverage for mid-market accounts, removing friction for 3% of existing customers and 8% of pipeline.
• Expenses:
• Receipt-Matching Improvements: Drives match rate above 71%, eliminating Harbor’s highest-volume support ticket category and improving user retention.
• Mobile App Rewrite: Eliminates framework deprecation risk ahead of the late-2027 vendor cutoff without stealing capacity from revenue-generating squads.

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Part 2: The Case for the Roadmap

Executive Summary

To achieve our board-approved target of 112% NRR by Q3 2027 ($86M ARR base expanding by ~$6.9M), Harbor must focus on the highest-probability, shortest-time-to-value expansion levers within our current 1,100 customers: multi-entity expansion ($2.9M ARR), capturing existing software spend via virtual cards ($1.3M–$2.2M ARR), and plugging Sage Intacct churn ($875k ARR retained).

Tom’s draft relied on an unbuilt Procurement module to generate $6M ARR in FY27. Ground-level capacity, vendor deadlines, and design partner data show that strategy carries severe revenue and operational risk. The proposed roadmap secures our existential card processor deadline, resolves major customer expansion requests, and establishes realistic hiring and product timelines.

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What Changed from Tom’s Draft and Why

#### 1. Realignment on Procurement ($6M ARR Myth vs. Reality) * The Math: Harbor has 1,100 customers averaging 700 employees (770,000 total users). With 10% raising purchase requests (70 users/account) at $8/user/month ($96/year), an adopting customer generates $6,720 ARR. To generate $6M ARR, 893 out of 1,100 customers (81% of our entire base) would have to buy and deploy a v1 module in under 9 months. * The Customer Signal: 4 out of 6 design partners already use dedicated tools (e.g., Coupa, Zip) and explicitly stated they will not switch. Only 2 of 6 expressed willingness to pay. * The Decision: Procurement cannot carry our FY27 NRR goal. We have reallocated primary capacity to guaranteed expansion drivers (Multi-Entity and Virtual Cards), while initiating a structured discovery and phased MVP build with Squad A.

#### 2. Realistic Hiring Capacity * Tom’s Assumption: Squad A operates at 100% capacity in Q1 2027 (11 squad-weeks) and Squad B in Q2 2027 (11 squad-weeks). * Historical Reality: Approvals to first full sprint took 5–8 months historically, delivering ~50% capacity in quarter one. Squads approved in September 2026 will not reach operational productivity until late Q1 / early Q2 2027. * The Decision: No critical-path milestone or revenue target in Q4 or Q1 relies on unhired squads. Existing squads carry core commitments; Squad A ramps on Procurement foundations in Q2 (delivering ~5.5 squad-weeks) and reaches full delivery in Q3.

#### 3. Strict Compliance with the 31 March 2027 Processor Deadline * The Constraint: The v1 API deprecates on 31 March 2027. Migrating takes 18 squad-weeks plus a mandatory 4-week processor certification freeze during which our codebase cannot change. * Execution Window: The 4-week certification must run in March 2027. Cards code complete must occur by Week 7 of Q1 2027. * The Allocation: Cards dedicates all 11 squad-weeks in Q4 2026 and 7 squad-weeks in Q1 2027 (18 weeks total). During the 4-week March freeze, the Cards squad transitions to architectural prep for Virtual Cards, avoiding wasted idle time.

#### 4. Resequencing Multi-Entity, SSO/SCIM, and Sage Intacct * Multi-Entity (Platform + Approvals): Prioritised immediately in Q4. 14 of our 60 largest accounts requested this; 9 have signed written commitments to add 52 subsidiaries ($2.9M ARR). Shipping in early Q1 allows two full quarters of rollout and revenue recognition. * Sage Intacct (Integrations): 17% of our customers use Intacct via CSV, churning at 13% vs. NetSuite’s 7%. Cutting churn across these 187 accounts ($14.6M ARR base) saves ~$875k in ARR retention while eliminating our top sales loss reason (31% of lost deals). * SSO & SCIM (Platform): Sequenced for Q1 immediately following core Multi-Entity work. For a 5-week lift, this unlocks $1.2M in stalled enterprise pipeline and secures 11 major renewals.

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How this Roadmap Hits 112% NRR

By the end of Q3 2027, this roadmap expands our $86M base by $7.0M+ in recurring expansion and retained ARR, exceeding the board's 112% target ($6.88M incremental):

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What We Are Not Doing (And Why)

1. Not building Procurement as a hasty monolith in Q1: Building a broad module against negative design-partner feedback on an imaginary timeline would burn 36 squad-weeks with minimal revenue return. We are building the data model and workflows methodically using Squad A once ramped.
2. Not assigning the Mobile Rewrite to an unhired squad: Tom assigned this 22-week project to Squad B in Q2. Squad B will not be staffed in time. Instead, the Expenses squad owns mobile: they finish Receipt Matching in Q4 (improving our #1 support issue) and execute the mobile rewrite across Q1 and Q2, completing it comfortably before late-2027 framework retirement.
3. Not prioritising Microsoft Dynamics over Sage Intacct: Dynamics accounts for only 3% of our customer base and 8% of lost deals (vs. Intacct’s 17% base and 31% deal loss). Dynamics is scheduled for Q2 after Intacct is fully deployed.
4. No cross-domain squad thrashing: Squads working out of domain suffer a 1.5× productivity penalty. We kept all squads focused within their domain expertise rather than forcing Expenses or Integrations to build Cards or Approvals features.

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Risks and Mitigation Strategies

1. Card Processor Certification Delay: * Risk: Processor testing slips past 4 weeks, threatening the 31 March v1 shutoff. * Mitigation: We complete Harbor development by Week 7 of Q1 (mid-February), yielding a two-week safety buffer before the freeze. Cards works closely with processor engineers weekly starting in Q4. 2. Multi-Entity Delivery Bottlenecks: * Risk: Multi-Entity touches both Platform (12 wks) and Approvals & Policy (10 wks); cross-squad misalignment could delay Q1 rollout. * Mitigation: The technical spec and API contract between Platform and A&P will be finalized in Sprint 1 of Q4, enabling independent parallel development. 3. Hiring Lags for Squad A and B: * Risk: Talent acquisition takes longer than the historical 5–8 months. * Mitigation: The baseline revenue plan (Multi-Entity, Virtual Cards, Intacct, SSO) relies entirely on our five existing squads. Squad A’s onboarding pace dictates the launch timing of Procurement, not the attainment of our 112% NRR target.