Pie Insurance
Pie Insurance Innovation & Technology Culture
Frequently Asked Questions
Pie was built on an innovative premise: that workers' compensation for small businesses was broken, and that Pie’s technology and data-driven approach could change the system. That founding instinct for innovation hasn't faded as the company has grown. Pie continues to invest in technology-driven improvements to the customer experience, underwriting processes, and claims management, and Pie-oneers say that appetite for innovation is visible in how the company approaches problems day to day.
Leadership encourages cross-functional experimentation and gives teams room to move quickly on new ideas rather than running every decision through layers of approval. For Pie-oneers who want to work on hard problems and see their solutions actually ship, Pie's size and growth stage offer a pace of innovation that's harder to find at larger, more entrenched insurers. The combination of an underserved market and genuine investment in technology makes Pie a place where innovative work translates into real-world impact.
Pie operates with a modern, cloud-native technology stack designed to scale with the business and support a fully distributed team. Pie-oneers describe internal tools as fast, reliable, and well-integrated, which matters in a company where engineering, operations, and customer-facing teams need to move in sync. Leadership invests consistently in infrastructure upgrades, enterprise grade AI systems, and productivity tools, which means the tech environment keeps pace with the company's growth rather than lagging behind it.
For engineers and technical Pie-oneers, working at Pie means working with current frameworks, contributing to a product that serves a large and growing customer base, and having real ownership over meaningful parts of the system. The technology isn't just modern for an insurance company; it's built with the same rigor and standards Pie-oneers would expect from any serious tech-forward business.
Technology is central to what Pie is and how it operates, not a support function sitting off to the side. The engineering and product teams are core contributors to the company's competitive position, and that's reflected in how they're resourced, how much ownership they have, and how closely they collaborate with all business functions. Pie's technology culture values craftsmanship, speed, and impact equally, and Pie-oneers describe an environment where good technical decisions get made for the right reasons.
Beyond the engineering team, Pie has built a culture where technology fluency is valued across the organization. Tools are chosen thoughtfully, processes are automated where automation makes sense, and the company operates with the expectation that good technology and strategic use of AI makes everyone's job better. For people who care about working somewhere technology is taken seriously as a craft and a business driver, Pie delivers on that.
Pie Insurance Employee Perspectives
What tools support your day-to-day work?
I have many different tools that help support my day-to-day work. At Pie, we leverage the Google software suite with Zoom, which is obviously critical for day-to-day work. We also leverage Jira, Confluence and other Atlassian tools for our project management, documentation and software incident response.
At a personal level, I leverage Claude Enterprise and Claude Code heavily for my work as a leader. This lets me pull analytics from Jira and our other metrics tools, like Github, AWS and others, to understand team performance and bottlenecks. As a leader, I’m also forced to context-switch a lot between meetings and topics. To support this, I’ve built up automation through Claude, Google Calendar and my note-taking app Obsidian to manage my notes, action items and calendar in order to stay on top of all my projects.
I, as a leader, also use Claude Code to rapidly understand different parts of our product for any support and technical questions. As I no longer perform software development day to day, these types of tools can let me understand pieces of our software much more quickly.
How does your team experiment?
As an insurance tech company, we leverage the Agile methodology. This focuses on small, iterative development processes across our organization, not just in technology. This also lets us perform experiments to test and learn quickly in the business, but this happens the most in engineering and product design.
For technology, we generally let teams experiment with new technology, processes or ways of working before bringing those results back to leadership and the larger group. This can be new software paradigms, new AI products, etc. The experiments are then presented at team all-hands, technology all-hands or staff meetings for others to discuss and adopt if successful.
Another big function we have at Pie Insurance is our bi-yearly hackathon. These are two-day events where everyone in the company is encouraged to bring ideas to our technology teams for rapid prototyping over two days. These ideas and experiments are then presented to different leaders, including the CEO, which are judged and could be immediately implemented into our products.
How does Pie Insurance adapt to change?
Where we can, especially in technology, we use the Kotter Model for change management to help drive change. This consists of creating urgency, enlisting champions, removing friction and sustaining acceleration, to name a few steps. We have used this model to force change in our AI adoption methodology. Through our product and company needs, we drove urgency, reduced friction by ensuring open access to tools and tokens, and also enlisted AI champions across the organization to mentor and bring others along. We then leveraged data available in some of our analytics tools, like developer intelligence platform DX, to see improved utilization and output from individuals.
For larger corporate-level change, we generally put together a “taskforce” that meets weekly to leverage data to drive changes within an organization or process. We leverage our enterprise data warehouse and data engineering and analytics team to provide this information. We are currently running a taskforce around some operational improvements specific to premium audit.
What People Are Saying About Pie Insurance
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Process Innovation: Feedback suggests Pie has built API-driven distribution, a partner portal, automated underwriting workflows, and payroll-integrated billing that reduce friction in workers’ comp and embedded channels. Evidence indicates these capabilities have supported multi-channel adoption and policy growth.
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Emerging Technology Adoption: The company is described as an early adopter of AI and advanced analytics across underwriting and claims on a modern, cloud-native stack to improve speed and efficiency. Feedback suggests ongoing investment by internal data science teams and enterprise-grade AI systems is core to its model.
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Innovation Operating Model: Pie’s transition from an MGA to issuing on its own carriers enables greater underwriting autonomy and faster product iteration. Embedded partnerships, including OEM-linked programs, demonstrate a diversified, technology-enabled go-to-market approach.
Pie Insurance's Tech Stack
