Leadership

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.

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.

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.

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.

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.

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.

Brenton joined Pie in April 2024 as VP of Product and brings nearly 15 years of leadership experience across product management, insurance, e-commerce, and market research. He was most recently a Sr. Director of Product Management for Global Supplier & Merchandising Platforms at Wayfair, where he led a team of 300+ technologists focused on the data, systems, and workflows that power a majority of Wayfair's end-to-end operations. Prior to Wayfair, he worked in innovation strategy and product management at Liberty Mutual Insurance, and led custom quantitative research engagements for many Fortune 100 clients with Kantar. He holds a B.A. in International Marketing and a M.S. in Resource Economics from UMass, Amherst.

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.