Scout InsurTech Spotlight with Phil Reynolds

Phil Reynolds is the CEO and Co-Founder of DevStride, the only project and portfolio management platform that orchestrates agile workflows alongside critical delivery timelines. He previously founded and scaled BriteCore, a leading core system for Property & Casualty insurers, where he spent nearly two decades transforming how insurance companies deliver technology. Phil was interviewed by Michael Fiedel, Co-Founder at Scout InsurTech and Co-Founder at PolicyFly, Inc.

Phil, can you expand on the depth with which you've dealt with delivery in the insurance industry?

“I spent 20 years building a full-stack core administration solution called BriteCore. We started with a basic quoting system for a group of small mutuals in 2005. At the time, we knew nothing about insurance. Our first real test was with Nixa Farmers Mutual, where we built a working solution by embedding ourselves on-site: interviewing team members daily and manually reconstructing their underwriting logic using sticky notes across office walls.

That kind of field-based customer discovery became our playbook. Eventually, we expanded beyond quoting into full policy, claims and billing systems, with deep integration to regulatory, financial and operational workflows. To do that well, we earned our CPCUs, studied insurance deeply and partnered with a core group of mutuals to co-develop what became BriteCore.

Working with capital-constrained insurers forced us to become ruthlessly efficient. That experience taught me how to blend product discovery, customer intimacy and structured delivery into a repeatable process. It laid the foundation for everything I do today at DevStride.”

What did you immediately love about the insurance industry, and what angered you the most?

“I fell in love with the mission. Most of our customers had been around for over 100 years. These were companies created to protect farms, families and communities. There was a deep sense of stewardship, holding the line for future generations.

But that long-term mindset came with a tradeoff: a strong resistance to change. For example, when we launched BriteApps (mobile apps for policyholders) adoption was painfully slow despite clear ROI. Insurers wanted to innovate, but inertia was a real hurdle. Still, once they made the leap, results followed. In some cases, we saw 10–20 percent growth in DWP following a mobile rollout. The lesson? Innovation has to be both culturally relevant and operationally feasible.”

What’s your perspective on timelines and delivery, particularly from a product point of view?

“There’s a joke in tech: ‘We’ll be live in June,’ knowing full well it’ll be December. But that’s not funny. It’s a cultural norm built around low accountability. I reject that.

At DevStride, we’ve proven that you can deliver software with precision. We’ve helped clients shrink delivery variance from six months to less than one week. That doesn’t happen by accident. It requires education, discipline and the right tooling. Technology projects fail not because they’re hard but because the problem and plan aren’t defined clearly enough.”

What are some of the challenges that disrupt the insurance industry's ability to consistently deliver faster, especially for projects that currently take one to two years?

“There are three big things. The first is the unknown current state. Many insurers don’t fully understand what their legacy systems actually do. That makes any transformation effort a leap of faith.

The second is regulatory volatility. Compliance requirements change often, and if your vendor isn’t proactively tracking regulators, you’ll always be behind.

Finally, there’s vague execution plans. When IT leaders say things like ‘we’ll take care of it,’ that’s a red flag. Precision matters. Delivery requires clearly defined roles, outcomes and milestones.”

You mentioned reducing a six-to-nine-month project to a week. What has to change for the insurance industry to experience that kind of improvement?

“Templating. Institutional memory. Playbooks.

If every project is a reinvention of the wheel, you’re doing it wrong. Success comes from capturing what works, whether that’s in code, process or decision-making, and building muscle memory across the organization. At DevStride, we help companies encode their best practices into reusable patterns.”

How does doing something new affect your timeline and approach?

“Insurers are in the risk business, not the R&D business. They shouldn’t be first-movers on every trend. Instead, they should partner with firms like ours that are plugged into the innovation frontier and know when a technology is ready to cross the chasm.

Blockchain in 2016? Mostly hype. Mobile apps in 2018? Absolutely critical. AI in 2025? It’s ready. We’re now helping clients operationalize AI for planning, summarization and decision support in a secure and regulated environment.”

If you're a leadership team looking at past failures or missed timelines, what should be the next step to move things in a better direction?

“Start by getting clarity. At DevStride, we help insurers define what they actually need, why they need it and how to go get it. That doesn’t mean pushing our software; it means aligning outcomes with strategy.

Whether the solution involves new technology, better tools or process redesign, the key is having a partner who understands both insurance and technology deeply. When you get that right, delivery becomes deterministic, not aspirational.”

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