Leadership

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Dax Craig

Co-founder and President

Dax is responsible for overseeing Pie's sales, business development, engineering, underwriting, product, and analytics functions. Prior to Pie, Dax was Co-founder and CEO of Valen Analytics, where he oversaw the company’s growth and 2017 sale to Insurity. During his time as a graduate student, he also founded Xertex Technologies, ultimately selling to Centurion Wireless. Dax holds an M.B.A. from the University of Colorado Boulder and a B.S. from the University of Tulsa Collins’ College of Business, where he serves as a member on the Advisory Board. Dax is a proud and long-term member of the Young Presidents’ Organization.
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John Swigart

Co-founder and Chief Executive Officer

John, who was named a 2020 Mid-Atlantic Entrepreneur of the Year, has been responsible for overseeing all aspects of Pie since its establishment in May 2017. He brings over 20 years of experience in tech-enabled insurance and financial services businesses. Prior to Pie, John served on the Esurance executive team for 13 years, where he initially led all of the financial functions from 2000-03 and then became the company’s first Chief Marketing Officer. Under John’s leadership of the marketing team, Esurance premium volume grew from $50 million in 2003 to $1.3 billion in 2013. Esurance was sold to Allstate in 2011 for $1 billion. John holds a B.A. in Economics from Haverford College.
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Ekta Aggarwal

Chief Product Officer

Ekta joined Pie in July 2022 as chief product officer, where she is responsible for scaling the product and design team and driving innovation across the company’s roadmap. Ekta has more than 20 years of experience in delivering rapid product innovation and scalable technologies, and has envisioned, built, and run global web and mobile technology products for some of the largest technology companies in the world. Before Pie, Ekta was the head of product for Microsoft’s Employee Experience Cloud, leading the product and science team for Microsoft Viva. Previously, she was general manager of Collaborative Shopping at Amazon where she oversaw Customer Q&A, Wish List, Share, Conversation service, and other customer experience-driven innovations. During her Amazon tenure, Ekta spearheaded some of the company's most innovative customer experience features including customer Q&A and social shopping experiences like chat within Prime Video watch parties. Ekta holds a M.S. in Operations Research from Boston University and a B.E. from Delhi College of Engineering.
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Thomas Capp

Vice President, Sales and Affinity Partnerships

Tom joined Pie in November 2020 to lead its direct sales and affinity partnership efforts. Most recently, Thomas served as SVP of Business Development at Answer Financial, SVP of Direct Sales at HealthMarkets Insurance Agency, and VP of Sales and Agency Marketing at Esurance. Thomas holds a B.A. in History from Northwestern University and an M.B.A. from Wharton School.
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Melissa Eaton

Vice President, Customer Success

Melissa, who was awarded DBJ's 2021 Outstanding Women in Business award and included in IBA’s Hot 100 list, is responsible for defining and driving Pie's customer success strategy initiatives. She joined Pie in December 2018 with over twelve years of experience in the insurance industry providing leadership in customer experience and customer care. Most recently, Melissa was Vice President of Customer Experience at Esurance where she led the Digital Product Management, Voice of the Customer, and User Experience teams. Under her stewardship, Esurance won two JD Power customer satisfaction awards, and Mercury Insurance recorded the largest annual increase in customer satisfaction points for Claims. Melissa has a B.A. in International Affairs from the University of Colorado Boulder.
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Matt Frazier

Chief Analytics Officer

Matt joined Pie in April 2018 and is responsible for leveraging data to build reliable predictive underwriting and pricing models. Matt joined Pie with over fifteen years of multi-disciplinary experience in the insurance industry. He’s helped successful companies, including First Comp Insurance and AmTrust Financial Services, expand into new and existing markets. Most recently, Matt helped establish strategic growth as the Scoring Officer and VP of Applied Analytics at Valen Analytics. Matt has a B.A. in Philosophy and a B.S. in Business Administration, Management, and Operations from the University of Washington.
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Tom Grossi

Chief Financial Officer

Tom joined Pie in July 2019 and is responsible for developing and implementing the company’s financial strategy. Prior to Pie, he was CFO at Optoro, a senior finance executive at Opower, and a partner at venture capital firm NEA. Tom has extensive experience leading high-growth, venture-backed organizations, including improving their forecasting, planning, and budget processes. Tom earned a B.A. and M.A. in Computer Science from Harvard University and an M.B.A. from Harvard Business School.
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Dimitrius King

Chief Claims Officer

As Pie’s first chief claims officer, Dimitrius is responsible for leading and implementing the company’s claims strategy. Over the past 15 years, Dimitrius has held various strategic and claims leadership roles in both personal lines and commercial lines at Liberty Mutual and The Hartford. His background includes leading in workers’ compensation, group benefits, auto, property, and catastrophe claims organizations. In prior roles, he was responsible for growing and refining multiple departments, which included legacy system transformation for all lines of business, large scale operational restructuring, and fostering high performing environments in order to achieve optimal business outcomes. He has a strong passion for diversity, equity and inclusion and has served as a leader in this space through his work with local and enterprise resource groups. Dimitrius holds a B.A. focused in Criminology from The University of Texas at Arlington.
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Chris Lankford

Senior Vice President, Engineering

Chris joined Pie in May 2021 and is responsible for scaling and operating the Software Engineering organization that is responsible for building Pie’s technology products and services. Chris has spent most of his career working on technology designed to disrupt legacy industries such as healthcare and logistics. Most recently Chris served as CTO at NEXT Trucking where he was disrupting the commercial freight industry. Chris holds a B.S. in Physics from Indiana University.
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Teresa Leon

General Counsel

Teresa joined Pie in July 2019 and is accountable for all compliance and legal functions. She has twenty years of experience in legal services and most recently served as General Counsel for ICW Group Holdings, one of the top 20 workers’ comp carriers in the country. Teresa has an impressive track record of advising and providing counsel to executive management on critical legal issues. She has a B.A. in Archaeology from Florida State University and a J.D. from New England Law Boston.
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Erin Mesick

Vice President, Finance

Erin Mesick joined Pie in June 2022 as vice president of finance, where she oversees the financial planning and analysis team, and is responsible for leading the organization’s strategic finance functions including financial planning, budgeting, forecasting, and KPI reporting. Erin was previously at Realtor.com where she held vice president roles in finance, strategy and operations. Prior to Realtor.com, she held multiple financial leadership roles at hyper-growth, venture-backed companies. She began her career in investment banking and worked in private equity at L Catterton. Erin earned a B.S. in Economics, with concentrations in finance and accounting, from the Wharton School of the University of Pennsylvania, graduating summa cum laude.
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Lauri Putt Needleman

Senior Vice President, People and Talent

Lauri joined Pie in May 2017 is responsible for recruitment, development, benefits, compensation, and coaching for Pie employees (also known as Pie-oneers). Previously, she led people teams at companies including RapidAdvance, AFP Advisors Network, and Fannie Mae. Lauri has a B.A. in Communications: PR & Journalism from the University of Maryland.
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Kelly North

Vice President, Business Development

Kelly joined Pie in April 2022 as vice president of business development, where she oversees the organization’s team responsible for growing and maturing its insurance agency channel. Previously, Kelly worked with national business development and sales teams at Beam Dental, Paycor, and Vivial. Kelly has a B.A. in Organizational Leadership from Northern Kentucky University.
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David Samuels

Chief Commercial Officer

David joined Pie as its first chief commercial officer in April 2022 and is responsible for setting Pie’s operational strategy, and overseeing all premiums generated from our insurance agents and brokers. With over 25 years of experience in sales leadership, customer success, business development, and product marketing within the B2B enterprise and SMB markets, David is adept at leading sales teams to win and guiding organizations to deliver on customer success strategies that accelerate retention and growth. At the core of his experience, David brings a passion for strengthening customer relationships, leading teams and setting high-performance standards. Before joining Pie, David was the chief customer officer at SAP, where he led the Customer Engagement Center and SAP Concur’s Global Client Development organization. David holds a B.S.B.A. from American University - Kogod School of Business.
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Nick Sinigaglia

Chief Accounting Officer

Nick joined Pie Insurance in May 2021 to lead Pie’s accounting and reporting efforts and brings with him decades of experience in high-growth companies. Nick has nearly 30 years of accounting and finance experience having most recently served as the Chief Accounting Officer of Money Mart. Prior to Money Mart, Nick served as the Chief Accounting Officer of OnDeck Capital where he guided the accounting function through an initial public offering and subsequent M&A activity. He began his career in the New York City office of Arthur Andersen specializing in mid-market SEC clients. He holds a B.S. in Accounting from the State University of New York at Albany and is a Certified Public Accountant.
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Amy Stern

Vice President, Reinsurance and Capital Solutions

Amy joined Pie in July 2021 to spearhead Pie's reinsurance and capital strategy. With 20+ years as a traditional and alternative market reinsurance underwriter and broker and experience as the Chief Ceded Reinsurance Officer for AIG, Amy brings extensive risk capital management expertise. Prior to Pie, she was a consultant at FTI, assisting in the launch and compliance efforts of numerous managing general agents and serving as a testifying expert in the broader re/insurance industry. Amy holds both CPCU and ARe designations and a B.A. in Economics from Cornell University.
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Jen Straus

Vice President, People Operations

Jen joined Pie in December 2021 and is responsible for compensation, benefits, people operations and analytics, learning and development, and our people partner function. She has led teams at hyper-growth startups, including Kabbage and Alteryx. She has a Ph.D. in Political Science and was previously a professor at Tulane University in New Orleans.
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Dale Willis

Vice President, New Lines

Dale Willis joined Pie Insurance in April 2021 to oversee Pie’s commercial auto team and efforts. In addition to the near-decade he spent at Progressive Insurance, he carries an extensive background in the insurtech space, most recently as VP of Data Services and Insurance at Netradyne. Dale holds an M.B.A. from Northwestern University’s Kellogg School of Management and a B.S. in Mechanical Engineering from Ohio State.