In 2017, Pie Insurance was just a handful of colleagues in a coworking space. As the small team worked together to reimagine workers’ compensation insurance for small businesses, the company began to chart a path toward growth rooted in innovation, serving customers and staying committed to its employees.
“I, of course, had big dreams and a vision of what we could become,” Co-Founder and President Dax Craig said. “I could not be more excited about what we have achieved to date. From working with one agency partner to over 4,000, and from our first customer to serving tens of thousands of small businesses across the country, driving Pie’s growth has been career-defining. Yet, in so many ways we are just at the beginning of our journey.”
Craig went on to explain that the opportunities before the organization are bigger than Pie itself — in his eyes, the company has the chance to continue to shift its entire industry.
“Through Pie, I want to fundamentally change how the insurance industry operates,” he said. “I want insurance to be a customer-centric industry. This means putting customer needs first and doing the right thing, especially when no one is watching. By focusing on the customer first, in an industry that often prioritizes compliance and internal needs, we can do good and build great businesses.”
He continued, “There is a huge gap in the insurance market for small businesses, because they have been historically underserved. Small businesses have been systematically ignored and overcharged because incumbent insurance carriers and agents have found it too difficult and costly to serve them. At Pie, we are leveraging technology and data science to deliver accurately priced policies and a simple process for agents. By prioritizing our customers’ need for easy to access and affordable insurance, I believe we will become the number one place small businesses go when shopping for commercial insurance.”
“I believe Pie will become the number one place small businesses go when shopping for commercial insurance.”
Pie’s Balanced Approach to Growth
Over the last six years, one thing is clear to Craig — growth isn’t just about getting bigger; it’s about getting smarter.
“We approach problems differently than traditional insurance carriers, by focusing on finding new solutions through a first principles approach rather than using established methods,” he said. “Our use of advanced data science allows us to create a more fair and equitable system for small businesses by pricing policies more accurately. As a result, small businesses only pay what their unique business should and no longer have to subsidize their less safe counterparts.”
He added, “Getting smarter means we are never satisfied with the status quo and are constantly testing and learning across everything we do. From vastly improving our quote processing times to constant refining of pricing algorithms, we are always searching for ways to innovate and find new efficiencies.”
Since its founding, Pie has expanded its workers’ compensation line to 38 states and Washington, D.C., and added commercial auto insurance. But the key to this growth has been Pie’s ability to scale with a long-term strategy built on a data science and technology-first approach and a workforce of dedicated “Pie-oneers,” as the team members are affectionately known.
Director of Workers’ Compensation Claims Paul Gladden shared a similar perspective on sustainable growth, emphasizing that it’s not just about the bottom line.
“Being new to the insurance tech world when I joined Pie, I envisioned that the company’s growth plans would be primarily centered around scaling and acquiring market share,” he said. “What has surprised and delighted me is the company’s focus on achieving scale and growing the business within a model that truly prioritizes its customers and the quality of the services offered.”
Adapting for Efficiency
At Pie, this investment in its team includes integrating cutting-edge technologies to drive operational efficiency.
“This allows our team to focus on strategic, high-impact work rather than getting bogged down by minute tasks,” Craig explained.
Senior Director of Field Underwriting Heather Chase echoed the sentiment of reimagining underwriting workflows and operating processes to serve both customers and agency partners more quickly and efficiently. Chase is focused on process improvement and automation, enabling her team of underwriters to streamline work and focus on more complex, value-added tasks.
According to Chase, digital transformation, self- serve capabilities and lightning-quick response times are the three key trends driving decisions for Pie’s partners.
“Our agents are looking for integrations with Pie’s and their agency management systems to provide a seamless exchange of information to allow them to service their clients quickly and efficiently,” she explained. “Small business owners are looking for affordable insurance coverage and quick claim processing and their agents are looking for streamlined, online solutions that provide instant quotes and simplified policy management.
“We have public APIs our partners connect to and integrations with agency tools like IVANS that provide a seamless flow of information between Pie and our agency partners,” she continued. “Staying agile and responsive to those trends ties in to our purpose — empowering small businesses to thrive.”
Chase went on to explain, “We are continuously pushing ourselves to be data based, forward-thinking and customer-first. We believe that being innovative, personalized, efficient and easy puts us at the forefront for growth in the small business marketplace.”
“We are continuously pushing ourselves to be data based, forward-thinking and customer-first.”
Building a Future-Focused Team
Growth at Pie is not just about expanding the business; it’s about investing in people. The company has developed internal resources to ensure that its teams have the skills they need to meet the changing demands of the industry. Craig emphasized the importance of continuous learning and development, with internal training programs, mentorship opportunities and regular performance reviews helping Pie-oneers align their development goals with the company’s evolving needs.
This investment in people is central to Pie’s long-term growth strategy. “Our approach ensures that we remain adaptable and resilient in an ever-changing economy and industry,” said Craig.
Pie’s leaders are united in their vision of fostering an environment where every team member understands their purpose, sees the impact of their work and feels empowered to contribute to the company’s success.
Gladden, who has witnessed Pie’s focus on upskilling its team members, shared, “Ensuring my team’s skill set grows in line with the evolving needs of the business is a top priority. We invest heavily in ongoing training programs, including both technical training and soft skills development. Mentorship and cross-functional projects are another resource we emphasize. By giving employees opportunities to work across different departments, we foster knowledge sharing and broaden industry expertise.”
As Pie looks to the future, Craig believes that now is the perfect time to accelerate growth.
“With continued advancements in technology and Pie-oneers on our team who are driven to innovate and serve our customers, I am confident that Pie will continue to scale,” he says.
“With continued advancements in technology and Pie-oneers on our team who are driven to innovate and serve our customers, I am confident that Pie will continue to scale.”
Pie has already established itself as a major player in the small business insurance market, but the company is far from resting on its laurels. With a strong foundation, innovative technology and a team of dedicated professionals, Pie’s journey is a testament to what happens when you invest in your customers and your people.
