Product-market fit (PMF) is one of the most cited and least understood milestones in building a technology company. For InsurTech founders, the stakes are even higher. Insurance is a relationship-driven, regulation-heavy, slow-to-adopt industry. Getting to PMF is not just about building a product people want; it is about building one that carriers, MGAs, and brokers can actually adopt.
At a recent ITA webinar, Phil Reynolds, repeat SaaS founder, 21-year CEO, and co-founder of DevStride, walked through his framework for navigating the path to PMF. Drawing on hard-won lessons from building and scaling InsurTech companies, Phil shared an agile, structured approach that any InsurTech team can apply.
Here is what he covered.
Why PMF Is So Hard to Reach
The goals of PMF are clear: deliver real value to customers, enable scalable growth, establish a competitive advantage, and hit the leading indicators that signal you have actually achieved it. The challenge is that most teams stall long before they get there.
Phil outlined the six most common obstacles InsurTech founders face on the path to PMF:
- Misidentifying true customer needs, building for assumed pain rather than confirmed pain
- Iterating with limited resources and few (or zero) customers to validate against
- Misaligning product development with actual market needs
- Slow feedback loops that compound bad assumptions over time
- Failing to adapt when market dynamics shift
- Sacrificing quality for speed, or vice versa
An Agile Framework for Achieving PMF
Phil’s framework organizes the path to PMF into six interconnected disciplines. None of them are one-time activities. They are ongoing, cycling loops that reinforce each other as your product and market understanding evolve.
1. Definition and Confirmation
Before writing a line of code, define your product by the problem it solves, not the features it delivers. This means conducting genuine customer research to validate (or reject) your hypothesis, identifying your total addressable market (TAM), and developing a clear product positioning statement.
Phil used Geoffrey Moore’s Crossing the Chasm positioning framework as a template: a structured exercise that forces you to name your target audience, acknowledge the gap your product fills, and differentiate against existing alternatives. This positioning statement becomes the test you hold every product decision against.
Also critical at this stage: name the competition honestly. Pretending you have no competitors does not sharpen your thinking. It just delays the conversations you will have to have anyway
2. Customer-Centric Planning
Early-stage planning should be low-fidelity and customer-driven. Phil’s team used Figma wireframes before building anything, established a Product Advisory Council (PAC) to get structured input from target users, and ran rigorous discovery calls to surface real needs rather than assumed ones.
A Proof of Concept (POC) comes next, not to impress investors, but to generate real feedback from real users under realistic conditions. The POC is a learning tool, not a sales tool.
3. Fast Iteration and Adaptation
Speed matters, but only if you are iterating against the right signals. Phil walked through a 13-step process for moving from POC to MVP: starting with a clear hypothesis, prioritizing assumptions by risk, defining success criteria, simplifying ruthlessly, and repeating the cycle of measure, iterate, and scale gradually.
The key discipline here is maintaining a living product roadmap that reflects what you are learning, not just what you originally planned. Market dynamics shift. Early adopters surface edge cases. Emerging technologies like AI open up new capabilities. Your roadmap should move with reality
4. Cross-Functional Collaboration
PMF is not a product team problem. It is an organizational alignment problem. understanding of the customer and the value proposition. Phil also emphasized the strategic value of partnerships and alliances, particularly in insurance where distribution relationships and carrier trust are often the decisive competitive factor.Marketing, sales, product, and support all need to be operating from the same
5. Measuring Progress
You cannot manage what you do not measure. Phil separated PMF metrics into two tiers. Basic metrics include retention rate, Net Promoter Score (NPS), growth rate, Customer Acquisition Cost (CAC), Customer Lifetime Value (CLV), and churn rate. Beyond the basics, teams should track activation rate, Time to Value (TTV), feature adoption rate, expansion revenue, and virality/referral rate.
The pattern that matters most: are customers staying, expanding, and telling others? That combination of retention, expansion, and referral is the clearest leading indicator of PMF.
6. Continuous Improvement
PMF is not a finish line. It is an ongoing calibration between what your product does and what your market needs, and both of those things keep moving. Phil’s team sustains continuous improvement through multiple feedback channels: a Product Advisory Council, pilot customers, user champions, support ticket analysis, feature request tracking, NPS surveys, usability testing, and regular customer interviews.
They also run A/B testing across every surface, including product features, marketing messaging, website copy, and social content. The goal is not to be clever; it is to replace assumptions with data at every opportunity.
The DevStride Case Study: What a Real PMF Journey Looks Like
Phil did not just present theory. He walked through DevStride’s own PMF journey, including the failures.
DevStride grew out of Phil’s experience co-founding BriteCore, an InsurTech company launched in 2009. After significant growth and an agile transformation, the team missed a critical delivery deadline in 2020, a failure that surfaced a deeper operational problem: there were no adequate project and portfolio management (PPM) tools built for teams like theirs.
That pain, lived, confirmed, and measurable, became DevStride’s founding hypothesis. The data backed it up: 25% of projects fail outright across the industry, 32% of project time is consumed by rework, and 55% of organizations have no formal PPM approach.
The market opportunity was clear too. The PPM SaaS market was valued at $6 billion and growing at 23% CAGR, on track to reach $716 billion by 2028, driven by AI, economic pressure to consolidate point solutions, and falling costs to build powerful B2B platforms.
DevStride’s positioning crystallized around a specific gap in the market: simple work management tools like ClickUp, Trello, and Jira do not scale. Enterprise PPM platforms like Planview and Jira Align are too heavy and too expensive for mid-market teams. No provider was delivering predictability to organizations with 10 to 1,000 contributors managing complex portfolios.
That is the gap DevStride is built to fill: a fully integrated agile solution combining people, process, and technology that gives mid-market teams the portfolio visibility and predictability previously only available to the enterprise.
How the Right Tool Accelerates PMF
One of the more practical insights from Phil’s session was how much a purpose-built tool can accelerate the PMF journey itself, not just help you build the product faster, but help you stay structured and aligned through the chaos of early-stage iteration.
DevStride is designed to support all six PMF disciplines: from problem definition and customer-centric planning, to fast iteration tracking, cross-functional collaboration, metrics reporting, and continuous improvement loops. For InsurTech teams managing complex product roadmaps against carrier requirements, regulatory timelines, and shifting customer expectations, that kind of integrated visibility is not optional. It is what keeps a founding team from flying blind.
The Bottom Line
Product-market fit in InsurTech is earned, not declared. It requires disciplined problem definition, sustained customer engagement, fast and honest iteration, aligned teams, rigorous measurement, and an organizational culture that treats improvement as permanent rather than as a phase.
Phil’s framework is practical, repeatable, and grounded in real experience, not just building SaaS, but building specifically in the insurance industry, where the path from idea to adoption is longer and harder than most founders expect.
ITA members can take advantage of a free one-hour PMF consultation with the DevStride team, plus a three-month trial subscription that includes up to eight hours of guided setup and support. If you are working through any of the challenges Phil described, it is a practical next step.
Frequently Asked Questions
What is product-market fit (PMF) in InsurTech?
Product-market fit in InsurTech means your solution is solving a real, confirmed pain point for a specific segment of the insurance market, whether that is carriers, MGAs, brokers, or another buyer, and that segment is adopting, retaining, and expanding use of your product. In insurance, PMF is harder to achieve than in most industries because sales cycles are long, stakeholder alignment is complex, and incumbent systems are deeply embedded. The clearest indicators of PMF are strong retention, expansion revenue, and unprompted referrals.
How long does it take to reach product-market fit in insurance technology?
There is no universal timeline, but InsurTech companies should plan for a longer runway than typical SaaS. Insurance buyers move cautiously, procurement cycles can span six to eighteen months, and integration requirements with legacy core systems add complexity. DevStride’s own journey took from 2020 through 2024 to move from idea to go-to-market, with meaningful iteration at every stage. Founders who reach PMF faster typically do so by narrowing their initial target segment, validating assumptions earlier, and building structured feedback loops from day one.
What metrics indicate product-market fit for a SaaS InsurTech company?
The strongest PMF signals for InsurTech SaaS companies are retention rate, Net Promoter Score (NPS), expansion revenue, and referral rate. Beyond those, teams should monitor Customer Acquisition Cost (CAC), Customer Lifetime Value (CLV), Time to Value (TTV), and feature adoption rate. A healthy pattern looks like: customers staying on the platform, paying more over time, and actively referring others. If you are seeing high churn or low activation despite strong initial sales, that is a signal that PMF has not been confirmed yet.
What is a Product Advisory Council and why does it matter for PMF?
A Product Advisory Council (PAC) is a structured group of target customers and subject matter experts who provide ongoing input into your product roadmap. Rather than relying on ad hoc feedback from sales calls or support tickets, a PAC gives you a repeatable, high-quality signal from the people whose problems you are trying to solve. For InsurTech founders, a PAC that includes experienced insurance operators, such as underwriters, program managers, or compliance leads, can dramatically shorten the time it takes to confirm or reject a product hypothesis.
How does agile methodology support the path to product-market fit?
Agile methodology supports PMF by creating short, structured cycles of build, measure, and learn. Rather than spending months building toward a fixed spec, agile teams release incrementally, gather real user feedback, and adapt quickly. For InsurTech startups, this matters because your assumptions about what carriers or MGAs need are often wrong in important ways that only become visible once real users interact with real software. Agile frameworks like SAFe, Scrum, and Kanban, when applied with genuine discipline, reduce the cost of being wrong and increase the speed at which you converge on what actually works.
