Scout InsurTech Interview with DevStride

DevStride is a project and portfolio management platform. They seek to orchestrate agile workflows alongside critical delivery timelines. Michael Fiedel sat with CEO and Co-Founder, Phil Reynolds, to learn more about how DevStride is impacting the industry.

Who are your clients?

We serve two main groups in the insurance space. One group is insurance technology companies that build and support core systems. The other is insurance carriers that need to coordinate across many internal teams during major implementation projects. These projects often require policy, billing, claims, data warehousing and other departments to move in sync, which is incredibly difficult to manage using something like Jira. Our platform was designed to solve this problem.

What does your product do?

DevStride gives teams the ability to manage work using layered Kanban boards. Each board can represent a small part of a larger effort, and all of those boards can be stitched together into a Gantt-style master timeline. When someone updates a single board, the entire delivery schedule updates automatically, showing what impact that change has on other parts of the project.

We integrate with tools like GitHub, Slack, Jira and Azure DevOps. That way, engineering teams can stay in their preferred environments, and we pull their data into DevStride. Delivery managers can then see and manage the full picture without asking engineers to change tools. We also use OpenAI to process incoming work items. For example, we can take a messy ticket, apply custom prompts based on the work type and then reformat or escalate it automatically. This helps us remove a ton of friction in project workflows and keeps everything moving smoothly.

Was the company born from within or outside the industry?

The company came from within the industry. I’ve worked in insurance technology for a long time and have personally felt the pain of these implementation challenges. I know what it’s like to live inside Jira, to manage hundreds of tickets and to try to coordinate across siloed teams. I built DevStride because I wanted a better way to manage and deliver complex technical work in this space.

What growth metrics have you accomplished over the last 12 months?

Right now, we’ve got traction with a number of smaller players who love the product. They’ve found it really useful, and it’s helping them a lot. But, I want to take things further. I’m aiming to land more visible, high-profile customers. These would be the kinds of clients that are willing to go public with a partnership announcement. I almost got there with a major Guidewire implementation, and I’m still chasing that kind of outcome. The goal is to go from “this is useful” to “this is essential and worth talking about.”

Within your domain, what is the current challenge that the industry is facing?

The biggest challenge I see is siloed teams. In an implementation, you’ve got a policies team, a claims team, maybe a data team, and they’re all working separately. No one is managing the dependencies between them. This creates massive delays and cost overruns. The cycle times stretch out because one team finishes late and that pushes the others back. What we do is help sequence all of these activities in a way that keeps everyone aligned and moving toward the same goal.

How does DevStride take a unique approach to providing value?

What makes us different is how we handle coordination. We don’t just manage tasks within a team. We show how work from different teams connects and impacts each other. Our layered Kanban system and master delivery timeline give visibility into everything. And since we integrate tightly with tools teams are already using, we don’t ask anyone to change how they work.

On top of that, we use AI to clean up and enrich work item descriptions. For example, we can flag unclear requirements, escalate problems and format submissions before they even hit engineering. This saves time and cuts down on the back-and-forth that slows projects down.

What inspired the team to start this company?

I’ve always been frustrated by how many things in enterprise work are harder than they need to be. We just accept it. We assume it’s always going to be painful. Whether it's tax season or software delivery, the inefficiencies are everywhere. I got tired of watching teams struggle to deliver because of broken processes. That’s what drove me to build DevStride. I wanted to solve something that should have been solved a long time ago.

Can you share any goals for the next 12 months?

Over the next year, my top priority is to bring certainty to project outcomes. I want people to stop guessing about delivery dates. I want them to know. Our mission is to remove the ambiguity and give teams confidence in their timelines. As far as specific goals go, I’d love to land three major implementation wins. These would be big, complex projects that we help turn around. That’s how we’ll prove our value and build the kind of proof points that make people take notice.

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