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.

---

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 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).

---

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.

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.

---

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.

---

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.

---

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):

---

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.

---

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.