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Dax Craig


Dax Craig: A Trailblazer in the Insurtech Industry

Dax Craig, the Co-founder and President of Pie Insurance Services, boasts an impressive educational background with an M.B.A. from the University of Colorado Boulder. He also holds a B.S. degree from The University of Tulsa Collins College of Business. Beyond his academic achievements, Dax actively participates on the Advisory Board of his alma mater. His leadership roles extend to the Young Presidents’ Organization and the Board of Directors at IMIDEX, an Israeli-based tech firm.

In 2020, Dax became a pivotal figure in the Colorado Inclusive Economy. This initiative strives to cultivate a more diverse, equitable, and inclusive business environment across the state.

The Genesis of Pie Insurance

Dax’s venture into the insurance industry began with Valen Analytics. As CEO, he provided data science solutions to traditional insurance carriers. However, he encountered resistance as clients failed to grasp the benefits of data science. This challenge ignited his ambition to establish Pie Insurance with John Swigart in 2017. Their mission was clear: to address the unfair treatment and overpricing of small businesses in the insurance market.

A Day into Dax’s Helmsman Seat

As President, Dax Craig’s responsibilities are vast. He oversees analytics, business development, customer service, direct sales, marketing, payroll operations, premium audit, and underwriting. His daily activities involve strategic oversight and hands-on team leadership. He dedicates time to both immediate tasks and long-term strategic thinking.

Pie Insurance’s Exponential Success

Under Dax’s leadership, Pie Insurance has become the fastest-growing workers’ compensation insurer in the U.S., with operations in 38 states and Washington, D.C. The company’s recent achievements include:

  • A nearly 30% expansion of its partner agent network.
  • Securing a $315-million Series D funding round.
  • Collaborating with Ford Motor Credit Company to introduce Ford Pro Insure.

Pie Insurance: A Deep Dive into Its Success

Pie Insurance offers workers’ compensation insurance to small businesses with fewer than 500 employees. The company leverages advanced algorithms and data analytics to price policies based on each business’s specific risks.

The application process for Pie Insurance is entirely online and can be completed in minutes. The company’s technology enables it to provide instant quotes to most businesses that apply. Additionally, Pie collaborates with agents to provide coverage to their small business clients.

Pie Insurance’s policies are underwritten by Sirius America Insurance Company, a subsidiary of Sirius Group. Recently, Pie transitioned to a full stack carrier and is rated A- (Excellent) by AM Best, reflecting its reliability.

The company’s technology platform allows businesses to manage their policies, report claims, and access other insurance-related services online. This makes the process more convenient and efficient for customers.

Since its founding, Pie Insurance has raised approximately US$615 million in funding from investors, including Greycroft, SVB Capital, and Aspect Ventures. The company has expanded its operations to cover 38 states and Washington DC in the US. It has received positive reviews for its easy-to-use platform and affordable pricing. In September 2022, Pie raised $300 million in a Series D round, doubling its total capital raised. This was the largest round of financing for any US-based P&C insurtech company in 2022.

Dax Craig’s Insights: Leading in the New Normal

Dax Craig believes the most important thing for leaders today is to listen more. He has learned to step back and listen to his employees, customers, and partners. This approach builds trust and loyalty. The pandemic has reshaped his perspective on leadership. He has realized that effective influence management requires engaging with team members at all levels.

At Pie, the fast pace of growth necessitates more listening and less talking to preserve their culture. They’re assembling world-class teams of experts. Dax’s role is to bolster their hard work and advocate for the customer to deliver top-notch products and experiences.

Moreover, Dax suggests leaders embrace remote work if they haven’t already. The pandemic has altered operations at Pie. By hiring beyond physical office locations, they’ve enhanced retention, boosted hiring rates, and significantly expanded their candidate pool. They’ve achieved this while maintaining a robust, values-driven culture.

Flexible work is here to stay, and industry leaders must adapt to safeguard and grow their businesses. Today’s talent will continue to demand the flexibility to work from anywhere. Business leaders aiming for growth must welcome remote work to attract the best candidates.


“It’s vital to ensure that agents are equipped with the tools and education they need to succeed and be a trusted partner.”

Also Read: The Most Prominent Leaders in the Insurance Industry, 2024


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