Problem → Goal → Feature → Metric
“Unclear Rx pricing” → “Increase price transparency” → “Rx Item Page” → “+40% Rx page visits QoQ”

“A roadmap isn’t a wish list — it’s your north star.”
That single line could summarize the decades of collective wisdom that experienced product managers carry.

In a recent talk, Hudson, Senior Product Manager at Walmart Labs, shared how he builds, aligns, and executes complex product roadmaps for cross-platform healthcare and pharmacy experiences across Walmart’s app and website. But what stood out wasn’t just the scale of Walmart’s operation — it was the clarity of thinking behind every product decision.

This post distills Hudson’s approach into a comprehensive, actionable guide — whether you’re managing your first startup MVP or orchestrating enterprise-scale platforms.

1. The True Purpose of a Product Roadmap

A roadmap isn’t just a list of features. It’s a strategic story that connects what your team is doing now to where you want your product — and your users — to be next.

Hudson defines a roadmap as:

“A compilation of all the ideas that feed into the future iterations of your product.”

But more importantly, it’s a communication device and a source of truth.

A great roadmap should:

• Reflect the product vision. It narrates where the product is and where it’s going.
• Communicate alignment. It becomes the most frequently referenced document inside the organization.
• Stay simple. No one reads complicated charts. Executives, designers, and engineers should all understand it at a glance.
• Anchor the team. Once aligned, it eliminates constant re-alignment meetings and “priority drift.”

A roadmap isn’t a technical document. It’s a narrative artifact that says: “Here’s what we’re doing, why it matters, and how it fits into our larger mission.”

2. Where Great Product Ideas Come From

One of the biggest misconceptions in Silicon Valley — and among junior PMs — is that the product manager must come up with all the ideas.

Hudson debunks that myth:

“Good ideas come from everywhere — customers, engineers, marketing, even Sally from Starbucks.”

He breaks down idea sources into several channels:

The PM’s real job isn’t idea generation — it’s idea filtration.
A skilled PM says “no” more often than “yes.” They weigh ideas against:

• The core value of the product.
• The long-term strategic vision.
• The company’s mission.

That’s how you prevent chasing shiny objects — short-term wins that derail long-term impact.

3. Start With the Problem, Not the Solution

Hudson emphasizes a foundational PM principle: Start with the problem.

“I’ve seen product managers get so anchored to a solution that they forget what they’re solving for.”

Every roadmap item must begin with:

1. The problem: What pain point are we addressing?
2. The customer: Who experiences this problem and why?
3. The benefit: What measurable value do they gain?
4. The alignment: How does it tie to the company mission?

Example: Walmart’s Pharmacy Experience

• Problem: Customers don’t know what prescription prices they’ll pay at Walmart.
• Solution: Build an “Rx Item Page” showing detailed medication information and transparent pricing.
• Goal: Increase price transparency and trust.
• Alignment: Supports Walmart’s mission of “Save money. Live better.”

This clarity ensures every roadmap item contributes to both customer value and organizational strategy.

4. Building the Roadmap Collaboratively

The biggest shift in Hudson’s process is how he creates a roadmap: collaboratively.

“Kick things off by having collaborative roadmap sessions with your stakeholders.”

Stakeholders may include:

• Engineering (tech feasibility)
• Design (UX/UI implications)
• Business strategy (revenue, compliance)
• Marketing (go-to-market support)
• Store operations (offline-online experience)

The key is to get buy-in early, not after you’ve already defined everything.
Why? Because alignment is easier to build than to repair.
It’s better to have a debate in the ideation stage than during development.

How to Run a Collaborative Roadmap Session:

1. Set the context. PM comes in with a clear product vision and 2–3 proposed goals.
2. Invite input. Allow debate on problems, not personal opinions.
3. Surface themes. Group similar ideas into “themes” like “improve refill experience” or “expand healthcare knowledge base.”
4. Filter ideas. Eliminate noise by referencing goals and customer value.
5. Record rationale. Capture why ideas were kept or discarded — it helps defend future trade-offs.

This approach fosters alignment, creativity, and ownership across teams.

5. Prioritization — The Benefit/Effort Matrix

Every roadmap eventually hits a wall: too many ideas, too little bandwidth.

Hudson’s favorite framework is the Benefit–Effort Matrix.

You plot every feature by:

• Y-axis: Customer or business benefit (value).
• X-axis: Technical effort (cost).

This creates four zones:

To plot accurately, you need both:

• Tech estimates — “t-shirt sizing” (S, M, L, XL) from engineering.
• Business context — how the feature contributes to OKRs.

“If engineers are sizing, they’re not coding — so keep it lightweight.”

6. Defining ‘Benefit’ Correctly

“Benefit” isn’t a one-size metric.

Hudson splits it into:

• Customer benefit: How much does this improve user experience?
• Business benefit: How does it drive growth, retention, or revenue?

Example:

• A “Family Prescription Linking” feature might not acquire new users, but it adds immense value for existing customers — customer benefit high, business benefit moderate.
• A “Referral Program” may not help existing users, but it drives acquisition — business benefit high, customer benefit moderate.

The PM’s job is to balance both.
Roadmaps that over-optimize for only one dimension — user happiness or growth — eventually stagnate.

7. Setting Goals and OKRs

Each feature or initiative on a roadmap should ladder up to Objectives and Key Results (OKRs).

Think of it as:

Problem → Goal → Feature → Metric.

For example:

• Objective: Improve medication price transparency.
• Key Result: Increase Rx page visits by 40% QoQ.
• Feature: Add itemized pricing details to the prescription landing page.

This traceability ensures that every task connects back to business impact.

8. The Quarterly Roadmap Format

Among various templates, Hudson prefers the Quarterly Release Roadmap.

It’s clean, time-boxed, and communicates well across departments.

Structure:

• Rows: Features or themes (e.g., “Prescription Refill Flow,” “Rx Item Page”)
• Columns: Quarters (Q1, Q2, Q3, Q4)
• Cells: Delivery target per feature
• Confidence fades: Certainty decreases for features farther into the future.

Example:

Why it works:

• Helps marketing plan campaigns.
• Keeps engineering focused by quarter.
• Makes executives comfortable with clarity and confidence levels.

9. Handling Roadmap Adjustments

But what happens when the real world changes?
A competitor launches a new feature. Leadership demands a pivot. A metric suddenly falls off a cliff.

Hudson’s answer: react with context, not panic.

“If you react too quickly, it probably means you never had a strong vision to begin with.”

Here’s how he advises handling shifts:

1. Acknowledge trade-offs. Every new request displaces an existing priority.
2. Communicate impact. “If we add this now, Feature B will slip to next quarter.”
3. Keep transparency. Stakeholders should never be surprised.
4. Track metrics. If performance disappoints, diagnose which features failed — not the whole roadmap.
5. Don’t abandon the vision. A bad quarter isn’t a reason to burn the plan.

This principle — flexible on tactics, firm on vision — separates average PMs from great ones.

10. Tools and Collaboration Systems

To maintain visibility and shared context across teams, Hudson uses:

• Confluence for hosting live roadmap pages.
• JIRA for epics, sprints, and backlog tracking.
• Quarterly updates to keep roadmap freshness without overhauling constantly.

Real-time dynamic roadmaps sound tempting, but Hudson warns:

“Too agile can become chaotic. You want adaptability, not volatility.”

11. Measuring Success — Metrics and Analytics

No roadmap is complete without measurement.

Hudson advises:

• Define success metrics early. Before development, decide what success looks like.
• Engage analytics late. Tagging happens when the build is ready, but notify analytics teams early.
• Measure both usage and behavior. Success isn’t just “feature used” but “feature delivering intended value.”
• Analyze drop-offs. If users abandon the flow midway, you have a UX problem, not a feature problem.

Typical product metrics include:

• Activation rate
• Retention / repeat usage
• Funnel conversion drop-off
• Time-to-task completion
• Net Promoter Score (NPS)
• Uptime and bug rate

But above all, metrics should answer a decision, not decorate a dashboard.

12. Handling Bugs, Tech Debt, and Maintenance

Every PM battles the invisible monster: tech debt.

“Bugs don’t stop happening,” Hudson reminds.

He classifies bugs into four severity levels:

1. P1: Critical — stop everything, fix now.
2. P2: Major — must fix before next release.
3. P3: Minor — UX or visual issues; fix in backlog.
4. P4: Cosmetic or negligible — can wait.

He never ships with P1 or P2 open.

To account for ongoing tech debt, he builds a 10–30% buffer into roadmap bandwidth.
That margin prevents production fires from derailing future sprints.

13. Roadmap Conflicts — The Real-World Trade-Offs

Product management is negotiation under pressure.

Common conflicts Hudson outlines:

Every PM eventually faces these trade-offs.
The only way to navigate them is alignment + data + clarity.

14. Gantt Roadmaps for Dependencies

When multiple teams or dependencies exist (backend, iOS, Android, web), Hudson uses a Gantt-style roadmap.

This highlights:

• Duration: How long each team is committed.
• Overlap: Which teams work concurrently.
• Bandwidth visibility: Prevents resource overbooking.

While more detailed, it’s useful for internal planning — not for exec overviews.

15. Handling Team Bandwidth and Resource Shifts

What if engineers leave mid-project?

“Something has to give — scope, timeline, or bandwidth.”

Possible actions:

• Bring in consultants or contractors temporarily.
• Borrow engineers from teams with idle capacity.
• Cut or postpone lower-priority features.
• Reassess OKRs to match new velocity.

There’s no magic fix — only transparent communication and controlled reprioritization.

16. Continuous Improvement — Sprint Retrospectives

Every sprint ends with a retrospective:

• What worked well?
• What didn’t?
• What can we improve next time?

Hudson sees retros as vital for team morale and process learning, not just technical feedback loops.

He notes that formal “release retrospectives” after big launches could add even more institutional learning — something many teams still do informally.

17. Leadership Alignment and Strategic Priorities

At Walmart Labs, priorities cascade from the top.

Leadership defines top company OKRs — e.g., “Double customer acquisition” or “Improve online pharmacy satisfaction.”
Each PM then maps their roadmap to these themes.

That alignment ensures no roadmap exists in a vacuum.

But it also means difficult conversations when two initiatives both support different top-level goals. In those moments:

• Refer to OKR hierarchy.
• Evaluate which initiative moves the needle more.
• Make trade-offs based on measurable business outcomes.

18. Dealing with Executive Overrides

Sometimes leadership — even the CEO — drops a new initiative mid-cycle.

Hudson’s tactic:

“You can say yes, but make the trade-offs visible.”

In other words:

“We can add this feature, but it pushes Feature X to next quarter, delaying benefit Y.”

This transforms reactive demands into informed decisions, protecting both your team and roadmap integrity.

19. The Human Side — What Makes a Great Product Manager

At the end of his talk, Hudson answered what every aspiring PM wants to know: What skills actually matter?

His answer is refreshingly simple:

1. Passion for the product. You must care about the space you’re in. The product becomes your life.
2. Empathy for users. Know the customer’s problem better than they do.
3. Appreciation for technology. You don’t have to code, but you must understand dependencies and feasibility.
4. Communication. Most of your job is alignment — not ideation.
5. Judgment. Know when to say no.

He adds:

“Usually there’s a passion area for you to serve — choose a product that genuinely excites you.”

20. The Product Roadmap: Your North Star

A roadmap, at its best, is a manifestation of conviction and clarity.
It tells your organization — and yourself — not just what to build, but why you’re building it.

Hudson closes with a reminder every PM should print above their desk:

“The roadmap is your vision. It’s where you’re going, and why you’re going there.
Once alignment is set, you can finally sleep better.”

And one final caution:

“Don’t overpromise. Don’t speculate. Keep it realistic. Always build buffer.”

Because at the end of the day, product management isn’t about predicting the future — it’s about navigating it with purpose.

Key Takeaways — The PyUncut Framework Inspired by Hudson

Final Thoughts

Hudson’s approach strips away the buzzwords and brings product management back to its essence: clarity, alignment, and value.

A roadmap isn’t a Gantt chart. It’s a strategic compass — one that keeps teams moving toward the same horizon, even when the weather changes.

Whether you’re managing a billion-dollar e-commerce product or a fledgling app, the discipline remains the same:

• Listen widely.
• Prioritize wisely.
• Communicate clearly.
• Build deliberately.

And above all, never forget why the roadmap exists in the first place —
to deliver real, measurable, human value.