Pie Insurance is a leader when it comes to small business insurance. Launched in 2017, the insurtech covers more than 38 US states and Washington DC, and is known for its strong company culture and innovative products that are disrupting the SMB insurance marketplace.
We caught up with Dax Craig to find out how he’s navigating today’s tricky environment – and which leadership skills and strategies are proving successful.
Tell us about your average day. What does your role entail on a daily basis?
At a high level, I oversee many aspects of Pie, including analytics, business development, customer service, direct sales, marketing, payroll operations, premium audit, and underwriting, so my day-to-day involves a mix of strategic planning and team management.
On any given day, you can find me checking in with my leadership team and reviewing progress on key initiatives and our OKRs (objectives and key results), meeting with individual team members to discuss ongoing projects and provide guidance, as well as meeting with external partners and stakeholders. I also ensure I have periods of focus time blocked on my calendar to think about large initiatives and the future state of the business, not just the day to day tasks.
Ultimately, when I’m at work, I’m having a blast. Insurance isn’t an industry that’s known for being fun, but at Pie, I’m truly enjoying the ride and the challenges that come with building a brand new kind of insurance company that does right by small businesses.
How did you get interested in the insurance space – and why?
Prior to founding Pie, I was the founder and CEO of Valen Analytics, where we offered data science solutions to traditional insurance carriers. Over time, I became increasingly frustrated because potential clients did not understand the value data science could bring to their organisation and many customers simply weren’t using Valen’s solutions to their full potential.
My frustration sparked the idea to create my own insurance company that built data science into the fabric of the business. I was introduced to my now co-founder John Swigart, former CFO and CMO of Esurance, and we saw a huge gap in the small business commercial insurance market. We recognised small businesses were consistently overlooked and overcharged by traditional insurance companies, often up to 30 percent. We founded Pie in 2017 to solve this problem and well, the rest is history!
You have a lot of experience in successful startups. If you could advise your younger self on new business propositions and opportunities, what would you say and why?
If I were to advise my younger self, I would say creating a company with an amazing culture doesn’t happen by happenstance. It takes hard, intentional work in order to build the right team carefully.
At a previous company, I hired mostly based on expertise and brought in the most qualified candidates I could. I made the mistake of not hiring people who could help build and expand our culture, and it nearly ruined the company. It took years to rebuild and weed out the culture misfits and I learned how important it is to have a company foundation built on core values. Above knowledge and expertise, to build a successful and sustainable company, all team members must align with the company values, operating principles, and overarching mission.
At Pie, I took my lessons from hiring at previous companies and put them into action. One of our first hires was actually a head of people and talent. I wanted to ensure we built people and culture into the core of the business and it’s paid off immensely. Pie’s culture is so vibrant and inclusive which is a direct reflection of the type of people we hire.
Pie was launched in 2017 – not long before the pandemic. How did you manage that period in terms of customer issues and adjustments? Tell us what strategies you employed.
In March 2020, when the COVID-19 pandemic made a rapid and significant impact on the U.S. economy, Pie’s cornerstone mission—to serve small businesses—was immediately called into action. First, Pie was open for business two hours after moving from the offices to people’s homes. Since we already operated 100 percent in the cloud, we were able to seamlessly continue serving our customers from home. Many insurance carriers and their agents were unable to quickly help their small business clients because they had on-premise technology.
In order to help as many customers as possible at the onset of the pandemic, we rebuilt our processes to better serve and educate our customers and partners on options and resources we could offer to help them. We immediately called all of our customers proactively, helping them adjust, pause, and/or postpone payments. The team processed thousands of account-level changes during the crisis, while navigating the complexity of workers’ comp regulations and temporary state-specific orders. In many instances, we reduced customers’ premiums to a single dollar, enabling them to save money at a critical time and also ensuring they wouldn’t lose coverage or have a difficult time renewing their policies in the future.
Additionally, we provided educational content for our customers throughout the pandemic, including safety tips, loan options, and information about planning for their business reopening. This hands-on approach required collaboration across all customer-facing teams at Pie, from marketing to sales to customer success, in order to best serve our small business customers.
This effort was especially impactful for customers who do not have an insurance agent and relied on Pie to be the insurance expert for their business. Rather than just sending an automatic email notice like many companies chose to do, we found that sometimes the most impactful thing for a customer was to call them proactively to understand their challenges and provide solutions.
What has the fallout of that situation been for your customers – and how should insurers be supporting small businesses in these turbulent times, in your opinion?
Now that COVID-19 disruptions are mostly behind us, a new set of challenges have emerged — inflation and labor shortages are creating uncertainty as businesses work to regain their footing. At Pie, we know that a critical part of knowing what small businesses need comes down to understanding the issues they are facing.
Small businesses are trying to run a business, and they often don’t have a lot of time or resources to monitor regulatory changes or shop around for better insurance rates. As partners who serve small businesses, it’s essential to recognize that owners need to be supported and given personalized attention and service – not just in the wake of challenging times – at all times.
Historically, small businesses have been neglected by traditional insurance companies—making it difficult to get covered. Insurers can help small business owners by providing the right insurance. Many insurance companies do not cover businesses if their premiums are too small. We can all help by providing accurate and fair pricing, easy-to-navigate solutions and excellent customer service. It’s also vital to ensure that agents are equipped with the tools and education they need to succeed and be a trusted partner. Agents play a vital role by identifying coverage needs, detecting gaps in customers’ current coverage, and solving issues quickly.
Insurers should also support small businesses in tactical, meaningful ways by hiring small businesses for day-to-day needs like event planning, catering, landscaping, etc. These choices add up and have a tangible impact on local businesses.
Outside of the insurance world, I strongly believe it’s also important we take care of the small businesses in our own backyards. We all need to support the owners and employees who make up our communities. You can do this by leaving a positive review of a business and shop small and locally as often as you can.
Are the current financial challenges (inflation etc) small business insurers are facing, something that could potentially damage the sector?
It’s difficult to predict the extent of the impact the current financial environment will have on small business insurers, but the insurance industry as a whole is highly regulated and has a long history of adapting to changing economic conditions and market trends. The impact of inflation and other financial challenges can also vary widely depending on the specific market and the individual insurer. We strongly believe that small businesses are incredibly resilient, adapt well to changing environments, and will weather future economic hurdles.
What’s your take on the investment space right now? Can scaling insurtechs still expect megarounds? Or will it be a while before that side of things recovers?
While there was a slowdown in funding in recent years, the sector has continued to grow, and there are still opportunities for scaling insurtechs to secure large rounds. In order for that to happen though, insurtechs must show their ability to deliver sustainable positive unit economics and profitable bottom lines. I don’t foresee the industry experiencing the funding exuberance we saw 2019-2022 but there will be a crop of insurtech 2.0s like Pie that will continue to scale, have profitable underwriting, and raise strong capital rounds.
In your opinion, what’s the most important thing all company leaders should consider at this time?
As a leader, I’ve leaned into stepping back and listening more to my employees, our customers, and our partners in order to build trust and loyalty. The pandemic completely changed my workplace mindset and view of my role as a business leader. I realised that to manage through influence effectively, it’s important to engage with team members at all levels like never before. As company leaders, we must be prepared to share stories of our own humanity to build understanding into the company culture.
At Pie, given our fast pace of growth, it is critical that I do less talking and more listening to ensure our culture remains strong. We’re building world-class teams of experts, and my job is to support and amplify their hard work while always advocating for the voice of the customer to deliver the best products and experiences possible.
In addition, I highly suggest leaders consider leaning into remote work if they haven’t yet. The pandemic changed how we operate at Pie and by hiring outside of physical office locations, we’ve improved retention, increased hiring rates, and drastically widened the pool of candidates. We’ve accomplished this while maintaining a strong, values-driven culture. Flexible work is here to stay, and industry leaders need to adapt to protect and advance their businesses. Today’s talent will continue to demand the flexibility to work from anywhere and business leaders who want to drive growth must embrace remote work to attract the best candidates.
What’s on the agenda for Pie Insurance over the next 12 to 18 months? Are there any interesting projects you can tell us about?
In late 2022, we announced a partnership with Ford Motor Credit Company to launch Ford Pro Insure, a new commercial auto insurance product powered by Pie. This partnership delivers customised commercial auto coverage and services to small businesses to help reduce fleet costs. We’ve already launched in Illinois and will be rolling out to additional states this year.
In February of this year, we transitioned into an A- (excellent) AM Best rated, full-stack carrier, which will allow us to scale even faster across the country.
We expect both of these large initiatives will benefit our customer significantly over the next 12 to 12 months.
How do you spend your downtime and stay grounded? Do you have any unusual hobbies?
I am in fact an avid skier and enjoy spending time outdoors in my free time. I live in the perfect state that offers me tons of opportunities to get outside and engage in activities like skiing, hiking, and biking. I am a measured thrill seeker and generally only seek out thrills I know are safe.
What’s next for Dax Craig?
I love what I am doing and see what’s next for Pie as the same as what’s next for me. I’ve never been as focused and motivated in my career as I am right now. Pie is the company I’ve always wanted to build, and I feel an exciting amount of pressure to keep our momentum going at a healthy and sustainable rate. I want Pie to become a household name and the number one insurance provider for small businesses nationwide. In order to do that, I need to continue pushing myself and Pie and growing as a leader.
Pie has grown from a team of two to well over 400 team members, and we have a company culture like no other. I want to create more amazing partnerships like our latest one with Ford and continue celebrating my team’s milestones and accomplishments. Most importantly, I want to continue enjoying every minute of the journey.
Five things to know about Pie Insurance
#1 Pie Insurance offers workers’ compensation insurance to small businesses with fewer than 500 employees. The company uses advanced algorithms and data analytics to price policies based on the specific risks of each business.
#2 The application process for Pie Insurance is entirely online and can be completed in minutes. The company’s technology allows it to provide instant quotes to most businesses that apply. In addition to online, Pie works with agents to provide coverage to their small business clients
#3 Pie Insurance’s policies are underwritten by Sirius America Insurance Company, a subsidiary of Sirius Group. In addition to serving as an MGA for Sirius Point, Pie recently transitioned to a full stack carrier and is rated A- (Excellent) by AM Best
#4 The company’s technology platform allows businesses to manage their policies, report claims, and access other insurance-related services online, making the process more convenient and efficient.
#5 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 also expanded its operations to cover 38 states and Washington DC in the US and 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 and doubled its total capital raised. It was the largest round of financing for any US based P&C insurtech company in 2022
Interview by Joanna England
