Roadmap Planning

Purpose: Build a shared, prioritized view of what to build next and why, grounded in customer problems and business strategy

How to run this meeting

Start with customer problems, not solutions. The most common failure mode in roadmap planning is walking in with a feature list and then reverse-engineering reasons to build it. Instead, spend the first 20–30 minutes reviewing actual customer signals: support tickets, sales call recordings, NPS verbatims, churned account interviews. Let the problems surface the ideas — not the other way around.

Use a scoring framework like RICE (Reach, Impact, Confidence, Effort) or ICE to make prioritization legible and less political. The goal is not to let the algorithm decide — it's to make your assumptions explicit so you can argue about them directly rather than arguing about the conclusion. When two items are close in score, the discussion about why reveals the real disagreement about strategy.

Leave 20–30% of the roadmap deliberately unplanned. This is not slack — it's a principled allocation for discovery work, fast-follow improvements, and things you don't know yet. Teams that plan every quarter to 100% capacity end up shipping what they planned 6 months ago while the world has moved on. The unplanned space is where you stay responsive to what you learn.

Before the meeting

• Compile customer signals from the past quarter: support volume by theme, NPS verbatims, sales win/loss data, customer advisory board feedback
• Pull current RICE or equivalent scores for all candidate items
• Review what was on last quarter's roadmap and what actually shipped
• Identify any hard constraints (regulatory deadlines, platform dependencies, contractual commitments)
• Send candidate items to attendees at least 48 hours in advance for async review

Meeting Details

• Date:
• Facilitator:
• Attendees:
• Duration: 2–3 hours

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Market Context

What is happening externally that should shape what we build? Competitive moves, regulatory changes, macro trends.

• Competitive: Stripe launched their embedded finance suite in January — two enterprise prospects mentioned it in recent sales calls as a benchmark for what they expect
• Regulatory: PCI DSS 4.0 compliance deadline is September 2026 — certain items on this roadmap are non-negotiable
• Market signal: Developer-first tooling continues to be a key differentiator in mid-market; companies with > 5 engineers are increasingly evaluating on SDK quality and documentation, not just pricing

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Customer Signals

Themes from actual customer feedback. Tie each theme to evidence — don't paraphrase without a source.

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Proposed Roadmap Items

All candidate items under consideration. Each should be a problem statement, not a feature name.

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Impact vs. Effort

Visual mapping of the candidate items. Use this to facilitate prioritization discussion.

High Impact
    |
    |  Multi-currency (Q2)        Onboarding (Q2)
    |  PCI compliance (Q2)
    |                  Webhooks (Q2)
    |
    |                        Bulk import (Q3)
    |
    |  RN SDK (Q4)        Analytics (Q3)
    |
Low Impact
    +--------------------------------
    Low Effort                High Effort

Key prioritization decisions:

• Multi-currency is highest RICE score and directly tied to churn prevention — Q2 commit
• PCI compliance is non-negotiable regardless of score — Q2 commit
• Onboarding ranked above Webhooks on reach and strategic importance despite similar scores
• React Native deferred to Q4 — low reach in current customer base, high effort

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Timeline

High-level view of what ships when. This is a roadmap, not a sprint plan — quarters are the unit.

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Decisions

Explicit decisions made during this session. Record the rationale — future you will want to know why.

• Multi-currency moved to Q2 committed: Churn data and pipeline impact made this the clearest prioritization call of the session. @product-lead owns delivery.
• React Native deferred to Q4: Current customer base is predominantly web-first; low RICE score confirmed. Will revisit if partnership inquiry converts.
• Analytics dashboard moved to stretch Q3: Low customer signal relative to effort; prioritizing items with direct revenue impact first.
• Developer onboarding is Q2 stretch, not commit: Engineering capacity constrained by PCI work; promoted to Q3 commit if onboarding work doesn't start by April.

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Action Items

Follow-up

Share the roadmap with the full company — not just engineering and product. Sales, customer success, and support teams need to know what's coming and when, so they can set accurate expectations with customers. The roadmap should be a living document, reviewed and updated at the start of each quarter. Establish a clear process for how new requests get evaluated against the current roadmap — without a process, every inbound request becomes a derailment risk. The next roadmap planning session should begin with a candid review of what shipped, what didn't, and what you learned.