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Founded Year



Series D | Alive

Total Raised


Last Raised

$315M | 1 yr ago

About Pie Insurance

Pie Insurance operates a platform for workers' compensation insurance. It matches price with risk across a broad spectrum of small business types that offer sustainable insurance to small business owners. The firm was founded in 2017 and is based in Washington, DC.

Headquarters Location

1615 L Street NorthWest Suite 620

Washington, DC, 20036,

United States


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Pie Insurance's Product Videos

Pie Insurance's Products & Differentiators

    Workers' Comp Insurance

    Pie combines innovative technology, sophisticated analytics, and industry expertise to provide small businesses and the partner agents who serve them with simple, trusted, and affordable workers’ comp insurance coverage.

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Research containing Pie Insurance

Get data-driven expert analysis from the CB Insights Intelligence Unit.

CB Insights Intelligence Analysts have mentioned Pie Insurance in 4 CB Insights research briefs, most recently on Aug 24, 2021.

Expert Collections containing Pie Insurance

Expert Collections are analyst-curated lists that highlight the companies you need to know in the most important technology spaces.

Pie Insurance is included in 6 Expert Collections, including SMB Fintech.


SMB Fintech

1,584 items



4,237 items

Companies and startups that use of technology to improve core and ancillary insurance operations. Companies in this collection are creating new product architectures, improving underwriting models, accelerating claims and creating a better customer experience



8,095 items

Companies and startups in this collection provide technology to streamline, improve, and transform financial services, products, and operations for individuals and businesses.


Fintech 250

500 items

250 of the most promising private companies applying a mix of software and technology to transform the financial services industry.


Silicon Valley Bank's Fintech Network

88 items

We mapped out some of SVB's biggest clients, partnerships, and sectors that it serves using CB Insights’ business relationship data from SVB’s profile to uncover just how important it is to the fintech universe. The list is not exhaustive.


Insurtech 50

50 items

Latest Pie Insurance News

Pie Insurance Expands Leadership Team with Appointments of Four Industry Experts

Aug 25, 2023

Carla Woodard, Jaime Gilliam-Swartz, Arash Sadati and Kris Bagchi join Pie’s leadership team as Vice Presidents. Pie Insurance  (Washington, D.C.), an InsurTech specializing in workers’ compensation insurance for small businesses, has announced the appointment of four industry experts to its leadership team. Carla Woodard was promoted to vice president of claims, Jaime Gilliam-Swartz was appointed to vice president of customer service and operations, Arash Sadati as vice president of data science and Kris Bagchi as vice president of reinsurance. More than a Century of Combined Experience Woodard, Gilliam-Swartz, Sadati and Bagchi bring more than 100 years of combined experience to Pie across claims, customer service and technology-focused roles at industry-leading companies. “All of these leaders bring a customer-centric mindset to Pie to help deliver on its mission of enabling small businesses to thrive by making commercial insurance affordable and as easy as pie,” a statement from Pie Insurance says. As vice president of claims, Woodard is responsible for overseeing Pie’s workers’ compensation claims function, including claim adjudication and subrogation. She brings more than 25 years of claims management experience to the leadership team, including most recently as director of claims at Pie. She previously spent 15 years at Employers Insurance as director of claims automation and workforce experience products. Jaime Gilliam-Swartz, VP, Services and Operations, Pie Insurance. Gilliam-Swartz is responsible for overseeing the company’s customer service, operations and premium audit functions as Pie’s VP, customer service and operations. She brings more than 25 years of diverse experience leading voice-of-customer programs, customer experience teams and shared service operations at companies like Eventbrite, Lyft, Intuit, GE and Accenture. As VP, data science, Sadati oversees the analytics team and is responsible for advancing Pie’s AI and Machine Learning capabilities and collaborating cross-functionally across the organization to drive product innovation through these technologies. He brings more than 15 years of experience to Pie as an expert in the ethical and responsible application of AI and Machine Learning, including his most recent role at GEICO. Kris Bagchi, VP, Reinsurance, Pie Insurance. As VP, reinsurance, Bagchi is responsible for developing Pie’s reinsurance programs, building and strengthening relationships with key broker partners. Bagchi brings more than 25 years of insurance industry experience including most recently spending nine years at TD Insurance/TD Bank in Canada where he was Vice President of Reinsurance, Corporate Insurance Underwriting and Investments. Adding Immediate Value Arash Sadat, VP, Data Science, Pie Insurance. “We’ve been extremely intentional when appointing new leadership team members at Pie,” comments John Swigart, co-founder and CEO, Pie Insurance. “We look for strategic experts who’re not only passionate about supporting small businesses, but who add immediate value to transforming the small commercial insurance industry. Carla, Jaime, Arash and Kris are poised to help Pie capitalize on our steady growth and realize our goal of becoming the number one preferred small business insurance provider on the market.” Anthony R. O’Donnell // Anthony O'Donnell is Executive Editor of Insurance Innovation Reporter. For nearly two decades, he has been an observer and commentator on the use of information technology in the insurance industry, following industry trends and writing about the use of IT across all sectors of the insurance industry. He can be reached at or (503) 936-2803. Leave a Comment

Pie Insurance Frequently Asked Questions (FAQ)

  • When was Pie Insurance founded?

    Pie Insurance was founded in 2017.

  • Where is Pie Insurance's headquarters?

    Pie Insurance's headquarters is located at 1615 L Street NorthWest, Washington.

  • What is Pie Insurance's latest funding round?

    Pie Insurance's latest funding round is Series D.

  • How much did Pie Insurance raise?

    Pie Insurance raised a total of $621M.

  • Who are the investors of Pie Insurance?

    Investors of Pie Insurance include Greycroft, Gallatin Point Capital, Acrew Capital, Allianz X, Centerbridge Partners and 9 more.

  • Who are Pie Insurance's competitors?

    Competitors of Pie Insurance include Hourly and 5 more.

  • What products does Pie Insurance offer?

    Pie Insurance's products include Workers' Comp Insurance.

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Looking for a leg up on competitive, customer and technology insights?
CB Insights puts confidence and clarity into your most strategic decisions.
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Trusted by the world's smartest companies to:
  • Predict emerging trends
  • See competitors' playbooks
  • Stalk the smart money
  • Identify tomorrow's challengers
  • Spot growing industries
  • Kill analyst data work
Let's see how we can help you!
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Compare Pie Insurance to Competitors

Next Insurance Logo
Next Insurance

Next Insurance is a company that focuses on providing insurance services, specifically tailored to the needs of small businesses. The company offers a range of insurance products including general liability insurance, workers’ compensation insurance, professional liability insurance, and commercial property insurance among others. These products are designed to cover a wide range of incidents and risks, providing protection for businesses in sectors such as food and beverage, retail, fitness, real estate, and many more. The company was founded in 2016 and is based in Palo Alto, California.

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Cerity is an Austin, TX-based insurance tech startup that is developing software that uses artificial intelligence to match worker's compensation policies to small businesses that otherwise wouldn't get them.

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Cowbell Cyber is a cyber risk insurance provider for small and medium-sized enterprises (SMEs). The company delivers cyber insurance policies customized to the needs and identified risk exposures of each organization and uses risk signals, artificial intelligence (AI), and technology to provide solutions to agents and brokers. It was founded in 2019 and is based in Pleasanton, California.

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Superscript provides business insurance services. The company offers general, management, and professional insurance coverage. It offers insurance products such as public liability insurance, business interruption insurance, cyber insurance, healthcare professional insurance, and more. Superscript was formerly known as Digital Risks. The company was founded in 2014 and is based in London, United Kingdom.


Assureful is an insurance company that provides a range of insurance products and services for e-commerce businesses. The company provides smart insurance for private label brands, retail arbitrage, resellers, wholesalers, aggregators, and more. It was founded in 2020 and is based in Spokane, Washington.

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Hiscox is a specialist insurance company. It offers errors and omissions, cyber and data security, media liability, entertainment production risk, general liability, professional liability, crime, ransom, terror, and property insurance through brokers and directly online to small businesses.

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