Leadership

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.

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.

Kris joined Pie in July 2023 as vice president of reinsurance and is responsible for developing Pie’s reinsurance programs, building and strengthening relationships with key broker partners, and will serve as Pie’s strategic liaison with AM Best.

Kris brings more than 25 years of insurance industry experience to Pie, including most recently spending 9 years at TD Insurance/TD Bank in Canada where he was Vice President of Reinsurance, Corporate Insurance, Underwriting, and Investments. He has a wealth of experience leading reinsurance, corporate insurance, and actuarial teams focusing on both strategic priorities and analytic excellence. Kris has worked in actuarial consulting, primary insurance and reinsurance companies throughout his career. Kris holds a B.S. in Applied Mathematics and Economics from University of California, Berkeley and is a Fellow of the Casualty Actuarial Society.

Josh Brost joined Pie in September 2022 as vice president of marketing, where he is responsible for all aspects of marketing including direct marketing, partner marketing, public relations, brand, lifecycle marketing, media, and talent branding. Josh brings nearly 20 years of diverse marketing experience to the Pie team. Most recently Josh led digital and integrated marketing at Bolt, and prior to that he led the growth and integrated campaigns team within the Modern Work marketing organization at Microsoft. Josh holds a Bachelors degree in Journalism from Metropolitan State University of Denver.

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.

Samantha Elizondo joined Pie in October 2022 as vice president of claims operations, where she is responsible for building out Pie’s quality, shared services, training, contact center, and special investigations unit. Samantha brings over 17 years of experience in the financial industry to the Pie team. Most recently Sam grew her career from team leader to assistant vice president over the course of 10 years at The Hartford. Sam holds a B.S. in Biology from the University of Texas San Antonio.

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.

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.

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.

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.

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.

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.

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.

Rick Poulin joined Pie in September 2022 as vice president of underwriting, where he is responsible for overseeing the company’s business planning, forecasting, and loss and expense management. Rick brings the team more than 20 years of experience in the insurance industry, including more than a decade at Travelers. Most recently at Travelers, Rick was the company’s vice president of workers’ comp where he was responsible for product development, line management, strategy and profitability across the entire line of business. Rick holds a Bachelors degree in Mathematics and Political Science from the University of Vermont.

Arash joined Pie in April 2023 as vice president of data science, where he oversees the analytics team. Arash 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.

Arash brings more than 15 years of experience to Pie as an expert of ethical and responsible application of AI and Machine Learning, specifically within the insurance and finance industries. Prior to joining Pie, Arash was the Head of Machine Learning Platform and Responsible AI at GEICO, and has also held senior data science roles at GEICO, Kemper and Capital One. He holds a PhD in Systems Engineering and Engineering Management from The George Washington University.

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.

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.

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.

Jaime Gilliam-Swartz joined Pie in February 2023 as vice president of services and operations, where she is responsible for overseeing the company’s customer success, operations, and premium audit functions. Jaime brings over 25 years of diverse experience across voice-of-customer programs, customer experience, and shared service operations. Prior to Pie, Jaime led service-focused teams at companies like Eventbrite, Lyft, Intuit, GE and Accenture. Jaime holds a Bachelor’s degree in International History from West Point and served 5 years in the US Army as a communications officer.

As Pie's vice president of workers' compensation claims, Carla Woodard is responsible for planning and directing all aspects of Pie’s workers' comp claims functions and teams. This includes managing and implementing strategic internal claims and TPA programs.

Carla brings over 25 years of claims management experience to the Pie team. Most recently, she spent 15 years at Employers Insurance as the director of claims operations. While there, she managed claims teams, designed claims processes, and led the implementation of claims management software. Carla holds a Bachelor’s degree in English from the University of LaVerne.