Build a roadmap

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.

Part 1: Roadmap, Q4 2026 to Q3 2027

Planning basis: Five existing squads at 11 squad-weeks a quarter (55 a quarter). The two new squads are counted as zero in the commitments (see the case). Lending between squads is costed at 1.5×. Figures in brackets are squad-weeks of the named squad.

Q4 2026: Protect the card rail, start entities

Q1 2027: Cut over, ship entities, start controls

Q2 2027: Virtual cards, procurement beta

Q3 2027: Launch and land

About 60 of 220 squad-weeks are deliberately uncommitted, mostly in Q3.

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Part 2: The case (≈1,150 words)

The short version

The order is set by one thing we can't negotiate and by the evidence for everything else. The processor retires v1 on 31 March, every authorisation runs through it, and interchange is 58% of revenue. Cards does nothing else until cutover. After that, work is ordered by evidence and cost per squad-week.

The plan gets our exit run-rate to roughly 109–111% NRR, not reliably 112%. We should tell the board that now rather than in Q3.

Why this order

1. v2 first, with real slack. Tom's draft has Cards doing 18 weeks at 11 a quarter, so build finishes around late February. Four weeks of certification then ends around 25 March, about a week before a deadline that would stop all card authorisation. My plan ring-fences Cards in Q4 and has Integrations, which does API work daily, lend 6 weeks (≈4 Cards-weeks). Code is complete in late January, certification runs in February, and we keep about five weeks of slack.

2. Multi-entity next. It has the best evidence we hold. Nine of 14 requesting customers said in writing they'd add subsidiaries, which means ~33 of the 52 subsidiaries, or ~$1.9M ARR. Customer Success's $2.9M assumes all 52 join. The cost is 22 weeks, and it is a direct "more entities" lever.

3. Intacct, then SSO. 17% of customers (~187) use Intacct via CSV and churn at 13% against 7% on NetSuite. If the integration closes that gap, it retains ~$0.9M a year for 9 weeks of work. That assumes average ARR of $78k and that the gap is causal, which is unproven. Intacct also appears in 31% of lost deals. SSO and SCIM costs 5 weeks and covers $1.2M of pipeline plus 11 existing accounts' security reviews. Dynamics is 12 weeks for 3% of customers and 8% of lost deals, and it serves new-logo growth, so it is stretch.

4. Controls before virtual cards. Both need v2 live, so both follow cutover. 31 CFOs asked for real-time controls against 26 for virtual cards. The 4 Approvals & Policy weeks for controls fit in Q1, before procurement takes that squad's capacity. Virtual cards is the only card item we can size: $410M × 10–25% capture × 1.1% ≈ $0.5–1.1M. The $410M is extrapolated from our 60 largest accounts, so it is probably high. This is a judgment call. Swapping the order is cheap, but the Approvals & Policy slot would collide with the procurement build.

5. Procurement: build it, resize the promise. At $8 × 10% of a 700-person company's employees, a customer pays $6,720 a year. Even 100% attach across 1,100 customers is $7.4M, so $6M needs ~890 customers (81%). Two of six design partners would pay (33%), and four already own a procurement tool. At 10–33% attach, year-one ARR is $0.7–2.5M, and with GA in Q3 only a small part lands before Q3 ends. It is still worth building: it is our only new paid module, it recurs, and it matches the board's "more modules" lever. But it is not a path to 112% on its own.

The arithmetic: 8 points of NRR on $86M is ~$6.9M. Sized items total roughly $4–6M of exit run-rate: entities $1.9M, Intacct $0.9M, virtual cards $0.5–1.1M, and procurement $0.7–2.5M (mostly after Q3). Controls and SSO retention are unsized upside. Recognised NRR at Q3 will lag run-rate because late launches haven't ramped.

What I changed from Tom's draft

• New squads count as zero. Last year's three squads took 5, 6 and 8 months from approval to first full sprint, then delivered half capacity in their first quarter. From a September approval, squad A is likely in seat between February and May and squad B later. A realistic ~5 weeks in Q2 and ~11 in Q3 for A, plus ~5 in Q3 for B, is about 22 weeks, against 55 in the draft. Even at Tom's capacity, procurement (36 weeks) couldn't launch in Q2, because squad A would have 22 weeks by the end of Q2.
• Procurement moves to Approvals & Policy. They own the domain and, in the draft, have no work after Q4. Expenses and Platform lend 9 weeks each (≈6 A&P-weeks each) to get a beta by the end of Q2 and GA in Q3. New squads join as upside.
• Mobile moves to Expenses. The draft puts it on squad B, which may not exist until Q3. Expenses has ~38 uncommitted weeks, and the rewrite ships in Q3, ahead of the late-2027 framework cutoff.
• Controls before virtual cards (point 4 above).
• Intacct GA moves from Q4 to Q1 to fund the v2 help. The cost is roughly one quarter of a ~$0.9M-a-year benefit, about $0.2M.
• Q3's "everyone else: adoption" is replaced by a held reserve, because adoption isn't squad work and Q3 launches can't move FY27 NRR much.
• A procurement checkpoint is added at the end of Q1 (see risks).

What we're not doing

• Dynamics, beyond a stretch start in Q2–Q3.
• A Q2 procurement launch, or putting the $6M figure in front of the board.
• Any new Cards scope before cutover.
• A mobile rewrite staffed by a squad that doesn't exist yet.
• Planning on capacity from squads we haven't hired.

Risks that could change the plan

1. Processor timeline. If v2 isn't code-complete by 31 January, Platform joins Cards and controls and virtual cards slip a quarter. Two asks for this month: a written fallback or extension from the processor, and confirmation that feature work behind flags is allowed during the certification freeze (my assumption). Book the certification slot now.
2. Procurement demand. At the end-of-Q1 gate I propose requiring at least 10 signed paid commitments at $8 from ~30 accounts approached (≈$67k ARR). If we miss it, we cut scope and redirect Approvals & Policy and the lenders to multi-entity rollout and card-spend work. The threshold is my proposal and is open to debate.
3. The NRR target itself. Exec decision: hold 112% as a Q3 recognised-NRR target, or restate it as an exit run-rate target, which I think is achievable only with upside from controls and procurement.
4. Evidence quality. The $410M is extrapolated from our largest accounts. The Intacct churn gap is a correlation. The multi-entity sizing rests on 14 of 60 customers. Any could be off by a factor of two.
5. Lending efficiency. The 1.5× penalty is an average. Expenses and Platform have less procurement context, and if they're slower than assumed, GA slips into Q4.
6. Hiring. If squad A lands in February, procurement GA can move earlier. If squad B lands late, nothing in the plan changes.
7. Mobile date. The CTO should confirm the exact end-of-support date and whether an in-place upgrade avoids a 22-week rewrite. Q4's scoping work answers this.

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.