The art of product roadmapping for early-stage SaaS founders

TL;DR: A great product roadmap is a flexible framework for communicating vision and adapting to customer needs, not a rigid plan. Early-stage founders should maintain three versions (annual for investors, quarterly for customers, and internal for teams) while focusing on solving problems rather than listing features.

As founders, it's easy to see your product roadmap as a long "to-do" list. We often plug it into a project management tool and dutifully work through it each quarter.

I’ve done this—and been a part of organizations that do this—many times over. It taught me a critical lesson: There's an art to creating a good product roadmap. It's often more about the process than the output.

I often reference Winston Churchill's quote: "Plans are of little importance, but planning is essential."

Yes, having a few vehicles for explaining your product and your view of the world matters. But for startups, the process is most important. It's about articulating a vision, prioritizing work against that goal, and adjusting based on customer feedback. The earlier you can start to get cycles in on planning as a team, the more accurate those plans will become over time.

This is an area I’ve spent a lot of time thinking through over the years. Thankfully, I’ve learned a few lessons and frameworks that can, hopefully, save you some time and frustration. Below, I’ll break them down.

Level set: What is a roadmap?

The product roadmap is a strategic communication tool that outlines the vision, direction, and progress of a product over time. It unites everyone around shared goals. It shows when, how, and why your product adapts to customer and market feedback.

Companies often take a feature-based view of their roadmap. They list what they plan to ship over a set time frame. They base discussions on the output of their work.

While this will give you a hit list for your next sprint, the feature-based roadmap falls short in several ways:

1. It can lead to unnecessary features and bloated products
2. It makes you focus on solutions rather than problems
3. It often lacks flexibility and adaptability
4. It can morph into Gantt charts more than actual roadmaps
5. It can make it hard to represent the uncertain timelines inherent in software development

I prefer a problem-based roadmap over listing features, which focuses on customer needs and allows for quick testing of market assumptions. This approach suits startups' iterative nature. It helps you communicate pivots and their impact while working toward your vision.

The relationship between vision, strategy, and roadmap

Before we delve into the specifics of roadmapping, we need to understand how vision, strategy, and roadmap work together:

1. Vision: Your north star. It shapes your company's direction, sets goals, and inspires employees, customers, and stakeholders.
2. Strategy: This outlines the path to your vision. It includes specific actions, initiatives, and approaches and requires a deep understanding of your market, customers, and internal capabilities.
3. Roadmap: This is your plan to execute the chosen strategy. It outlines specific steps, milestones, and timelines and breaks your strategy into actionable tasks.

These three elements are interconnected but distinct. Your vision directs strategy development. Your strategy aligns with it. Your roadmap guides strategy implementation.

When all three levers are equally balanced, your roadmap helps you:

1. Communicate vision and strategy to explain where the product is heading and why. It encapsulates how your product strategy becomes reality.
2. Align teams and stakeholders around the same goals. This will create a shared understanding and boost cross-functional collaboration.
3. Guide decisions on priorities and resource use and inspire and motivate your team.
4. Engage customers and investors to get buy-in and demonstrate market focus, strategy, and value for customers.

The three flavors of roadmaps for your investors, customers, and team

Your roadmap is an iterative version of your product pitch geared toward everyone who cares about what you’re building. People's understanding and support depend on how well you tailor your message to their needs and wants.

I've found that early-stage startups benefit from three types of roadmaps. Each serves a different purpose and audience:

1. Annual roadmap for investors: A high-level strategic document. It shows your vision and long-term plans to investors. and focuses on major milestones and market opportunities for the next 6-12 months.
2. Quarterly roadmap for customers: A tactical roadmap. It shows customers the value and improvements to expect in the next two quarters and builds excitement and shows progress on the solution.
3. Internal roadmap for team alignment: A detailed source of truth. It guides your team's daily work with tasks and resource allocation for the next 6 months.

Let’s take a look at each of these types in a bit more detail.

1. Annual roadmap for investors

Your annual roadmap is your startup's North Star. It guides your trajectory and excites investors about your 12-18 month plans.

This roadmap should answer the following crucial questions for investors:

• What big problems are you solving?
• How will your product capture and expand market share?
• How does your strategy align with long-term industry trends and your company's vision?

In the example above for our work at Clarify, we’ve laid out our major initiatives by quarter through the end of the year, including mile markers for our early access and soft launches.

To answer those questions, there are three main elements that should be included in your investor roadmap:

1. High-level product vision: A clear statement of the future state you're building toward and how your product will evolve to seize market opportunities.
2. Major milestones and features: The significant achievements and capabilities you plan to deliver, focused on business impact rather than technical details.
3. Market opportunity and competitive positioning: An analysis of your target market and how your planned developments will help you capture and defend market share.

When crafting your roadmap, set ambitious goals. They should excite investors but also maintain credibility. Focus on outcomes and account for potential pivots due to market changes and past learnings.

2. Quarterly roadmap for customers

Your quarterly roadmap turns your vision into a plan. It outlines near-term improvements to show progress and excite customers about upcoming features in the next 3-4 months.

This roadmap should answer the following questions for customers:

• What problems will you solve for me in the next few months?
• How will these solutions make my life easier?
• When can I expect to see these improvements?

Our quarterly roadmap breaks down main deliverables month by month for the current quarter, with a preview of tier-one features coming in the next quarter.

To build an effective quarterly roadmap, focus on three main elements:

1. Breaking down annual goals: A clear sequence of problems you'll solve each month, aligned with customer feedback and building toward your bigger vision.
2. Problem prioritization: A structured approach to choosing which customer pain points to address first, based on impact and feasibility.
3. Value communication: A clear articulation of outcomes and benefits, focused on how each solution will improve your customers' work.

When presenting quarterly roadmaps to customers, I balance specificity with flexibility. I share planned solutions for each month and seek feedback on what resonates or might be missing. I've found it effective to present it as: "Here are the key customer problems we're planning to address in October, November, and December. What resonates with you? What's missing?"

3. Internal roadmap for team alignment

Your internal roadmap is your team's daily guide. It breaks down high-level strategy into specific problems and bets to test over the next quarter.

This roadmap should answer the following crucial questions for your team:

• What specific problems are we tackling right now?
• Who is responsible for each piece of work?
• How do our daily tasks connect to our bigger goals?

We use Linear's initiatives feature to track our internal roadmap, breaking down deliverables and GTM activities while mapping dependencies between releases.

To build an effective internal roadmap, focus on three main elements:

1. Granular planning: A detailed breakdown of problems and ideas. It guides daily work and decisions.
2. Resource allocation: Map tasks to teams and individuals. Set realistic timelines and dependencies.
3. Progress tracking: Regular updates and tweaks to keep everyone aligned and moving toward shared goals.

Weekly planning sessions and monthly reviews keep your roadmap relevant and actionable within a quarter's view, since - like fog of war - you have more clarity the closer you get to delivery.

Best practices for first-time founders

Building your first product roadmap can feel like navigating without a compass. After years of building roadmaps at startups and big firms like Amplitude and Atlassian, I've learned that success isn't about a rigid template. It's about embracing principles that keep you focused on what matters.

Here are six best practices to keep in mind that will help you create a high-impact, inspiring roadmaps:

1. Prioritize problems, not just solutions: Explain the problems you're solving, not just the features you're building. This will help you focus on impact and make it easier for customers to understand what you're doing for them.
2. Prioritize based on value and effort: Use frameworks like ICE or RICE to assess customer impact and value. One question we often revisit is: "What will increase the willingness to pay for our product?"
3. Embrace the budgets over estimates: Set budgets for problem-solving, not detailed estimates. This helps us agree on the value of tasks as a team. For example: "We're willing to spend three engineering weeks on this problem.”
4. Leave room for quality and craftsmanship: Build time for refinement and polish into your roadmap. Remember that quality can be a key differentiator, especially as you grow.
5. Use roadmaps as conversation starters: Your roadmap is a tool for discussion, not a binding contract. You should encourage feedback and be open to making adjustments based on new learnings.
6. Balance discovery and delivery: Acknowledge the phases of product development and allow for both exploring new ideas and delivering validated solutions.

Just like your roadmaps themselves, use these as guideposts and feel free to adapt them based on what works best for your team and your customers.

A good roadmap isn't about checking off feature boxes. It's about delivering value efficiently and aligning your team, customers, and investors. From managing stakeholders to adapting to the market, here's how to measure success and tackle roadmap challenges.

Measuring roadmap success and effectiveness

When it comes to measuring the success of your roadmapping process, use a mix of qualitative and quantitative metrics aligned to your overall business goals and user needs. On the qualitative side, you want to see that:

1. Your team is aligned around priorities and direction.
2. Your customers can clearly articulate what you’re building
3. Your investors are inspired by your strategy and bought into your vision.
4. You feel capable of quickly adapting your plans.
5. You are consistently executing against your roadmap.

On the quantitative side, you can look at tracking:

• Customer willingness to pay for planned features
• Time spent in discovery vs. delivery phases
• Delivery rate against budgets
• Customer requests for roadmap items
• Feature adoption after launch

These metrics aren’t set in stone. Regularly gather feedback from your team, customers, and investors and adjust what "good" looks like as your product evolves.

Remember, your roadmap is not a contract. It's a tool for starting conversations, gathering feedback, and aligning expectations. Be prepared to adapt and evolve your roadmaps as you learn and grow.

Embracing flexibility: The key to successful product roadmapping

Creating effective product roadmaps is as much an art as it is a science. It requires a delicate balance of vision and flexibility, detail and high-level strategy. A problem-based approach will help you create better roadmaps that are more flexible, customer-focused, and aligned with your business goals.

Your roadmap is not set in stone. It's a living document that should evolve with your business. Use it to start conversations, gather feedback, and guide your decision-making. With practice, you'll create a roadmapping process that moves your startup forward.

If you have questions about creating your first roadmap as a founder, or advice I didn't cover, I would love to connect.