Leadership team
Drew DiGiorgio
President & CEO
As President & CEO of Wellfleet, Drew DiGiorgio is driving expansion and diversification of product offerings by providing unique health care solutions that improve quality of care and expand choice for our members.
With a degree in Business Administration and insurance broker experience, Drew joined Wellfleet in 1995. He managed the company’s PPO network prior to leading the Student Health Sales, Marketing, Client Relations, and Underwriting teams. Under Drew’s leadership as Sales Director and President, Wellfleet enjoyed impressive company growth and increased market share, which attracted Berkshire Hathaway to add Wellfleet to its well-regarded portfolio of companies.
Drew was named President & CEO of Wellfleet in 2015, and in 2017, Wellfleet expanded its TPA services to include insured products. He continues to drive Wellfleet’s growth by leading the expansion into Workplace Benefits products and the creation of its custom-built administration platform, Lighthouse; enhancing Student Health product offerings and administration; and supporting an emerging Special Risk division.
Karen Matys
Chief Operating Officer
As COO, Karen is laser-focused on Wellfleet’s operational excellence and customer centricity. Karen joined Wellfleet in 2009 and has over 30 years’ experience in the healthcare industry. She oversees the Claims, Customer Service, Support Services, Plan Configuration & Quality, Student Health Enrollment & Waiver, and Workplace Claims & Customer Care departments.
She’s an experienced administrator for fully insured and self-funded employer sponsored plans, HRA & FSA, student accident and sickness, intercollegiate sports, special risk, limited medical and ancillary benefit plans. Karen has successfully steered Wellfleet through its expansion from a TPA to an insurance carrier, streamlining operations while implementing impactful quality improvements that enhance the customer experience. Prior to joining Wellfleet, Karen was the VP of Operations at Pioneer Management Systems.
Aaron Krieger
Chief Legal Officer
As Chief Legal Officer, Aaron is focused on mitigating risk and maintaining compliance amidst a complex legal landscape.
He oversees the Legal Department, which includes the Regulatory, Compliance, Filing/Product, Appeals and Internal Audit teams.
Aaron has over a decade of in-house legal experience in the insurance industry. He joined Wellfleet in 2021 from MedPro, where he was Corporate & Regulatory Counsel.
Before earning his law degree at Indiana University, Aaron served in the Air Force for 6 years, earning the non-commissioned officer rank of Staff Sergeant. He chairs the Military Families Group, an Employee Resource Group (ERG) for all MedPro employees.
Carlo Ciotoli
Sr. VP for population health & CMO
As Senior VP of Population Health and Chief Medical Officer, Carlo Ciotoli works to facilitate the adoption of Wellfleet’s Triple Aim approach of better health outcomes and better care, with lower costs. Carlo leads the Provider and Network Management teams and works closely with the Healthcare Optimization team to provide clinical oversight of services, quality, and access to care for students while managing healthcare costs.
Carlo is a cum laude graduate of the University of Pennsylvania, received his M.D. degree from New York University and earned his Master of Public Administration in Health Policy and Management from NYU’s Wagner School of Public Service. He is board certified in Internal Medicine.
Brian Judy
EVP of Student Health
As EVP of Student Health, Brian Judy leads the charge of providing student-focused insurance solutions amidst an ever-changing health and wellness landscape.
Brian joined Wellfleet in 2023. He has 19 years of experience in the industry, most recently as Regional VP of Business Development at Academic Health Plans and Risk Strategies, and prior to that, as VP and Head of Student Insurance at both USI and Wells Fargo Insurance Services. Brian leverages his consultant background to create trusted partnerships with universities and ensure the solutions Wellfleet offers align with the needs of our customers.
Jennifer Stevens
VP of Healthcare Optimization
As VP of Healthcare Optimization, Jennifer Stevens works to deliver effective clinical and cost-containment programs and processes embedded within Wellfleet’s Student Health insurance products and operations.
Jennifer’s team includes Pharmacy, Clinical Support, Payment Integrity, and Medical Economics units that implement strategies to improve services, quality, and access to care for students while managing and conserving healthcare claim costs.
Jennifer joined Wellfleet in 2015 to grow its Medical department and led the creation of Wellfleet Rx, our student-focused pharmacy solution. She has more than 14 years of experience in the healthcare and pharmacy industries. Jennifer holds a Master of Health Administration/Informatics from the University of Phoenix, a Bachelor of Science in Psychology/Neuroscience from UMass Amherst, and a Women in Leadership Certificate from the University of Vermont.
Aaron Chalifoux
IT Director
As the RTE and IT Director, Aaron oversees our application development teams across all Lines of Business (LOB).
His responsibilities encompass development, quality assurance, Agile methodologies, and production support. He also serves as a key client liaison for select strategic accounts.
Aaron joined Wellfleet in 2016 following the acquisition of AIG’s Educational Markets business. With over 15 years of experience in insurance application development, he brings a wealth of expertise to his role. Prior to joining Wellfleet, Aaron served as Manager of Application Development at AIG.
Jim Foley
VP of Product & Underwriting
As Vice President of Product & Underwriting, Jim is responsible for Wellfleet’s product portfolio, product positioning, and pricing strategies to ensure long term success. Jim was hired in 2018 to lead Workplace product innovation/development and underwriting, and his oversight later expanded to include product innovation, implementation, and underwriting for all three Wellfleet divisions.
Jim has more than 25 years of experience in workplace benefits including leadership roles in product, underwriting, and strategy at Unum, Voya, Humana, and Manhattan Life.
He holds an MBA in Marketing from Indiana University’s Kelley School of Business and earned his undergraduate degree from North Dakota State University. Prior to entering the insurance industry, Jim was a military intelligence officer in the Army.
Brad Ober
VP & Chief Actuary
As VP and Chief Actuary, Brad helps minimize Wellfleet’s financial risk by using data, mathematics, and financial models to ensure that insurance policies are properly priced, and reserves are appropriately set.
Brad joined Wellfleet in 2016 with 15 years of experience as an actuary, having previously served as VP, Chief Actuary, and Appointed Actuary for Reserve National Ins. Co. (Kemper, Inc.) in Oklahoma City.
Brad is a Fellow of the Society of Actuaries (FSA). He holds a Bachelor’s in Mathematics from the University of Oklahoma and a Master’s in Predictive Analytics from Northwestern University.
Brian Haas
Director of Special Risk
As Director of Special Risk, Brian Haas oversees distribution and servicing of Intercollegiate Sports, K-12 and Participant Accident products, leading the way to profitably expanding this division.
Brian has over 35 years of experience in the Special Risk industry, with a background in sales, underwriting, account management and operations. Prior to joining Wellfleet in 2023, Brian was the Director of Life, AD&D and Special Risk Products for Prudential Insurance.
Brian is a graduate of Rutgers University. He earned the CEBS Designation in 2007 and has served in various roles at the local and national levels for the International Society of Employee Benefit Plans. He also served in various board positions for the American Special Risk Association. Brian is also an Eagle Scout and is in the Eagle Scout Hall of Fame.
Patricia Coughlin
Human Resources Director
As Human Resources Director, Patricia Coughlin builds a team of employees empowered to deliver Wellfleet’s mission and strategic goals.
Patricia has more than 25 years of experience in HR and Operations management. Prior to joining Wellfleet in 2017, she was an HR Manager at New England Business Associates (NEBA).
Her team manages a full HR program, including recruitment, onboarding, compensation, compliance, performance management, professional development, and employee recognition and engagement. Patricia strives to identify opportunities for process improvement to implement positive, functional changes within the company.
Patricia has a bachelor’s degree in business management from Westfield State University and holds a PHR (Professional in Human Resources) certificate.
Jay Fearrington
VICE PRESIDENT OF
BUSINESS INTEGRATION
As VP of Business Integration, Jay is responsible for mitigating risk through corporate oversight of critical vendors/business partners and for cultivating change management for Student Health and Special Risk initiatives.
Jay joined Wellfleet in 2016. His background combines many years in executive roles focused on project management, business development, account management, and sales in industries ranging from IT and insurance to manufacturing. Jay has a BA and an MBA from the University of North Carolina.
Ben Larsen
Digital Experience Officer
As Digital Experience Officer, Ben is focused on centralizing and strengthening Wellfleet’s digital approach and strategies.
Ben oversees Wellfleet’s digital strategy, user experience, and digital product management. Previously, he led Wellfleet’s marketing and communications, including all brand, advertising, and content.
Ben is an experienced content creator, agency consultant, and marketing strategist with more than 20 years of experience in the media and marketing worlds. Ben previously worked for ESPN, MassLive.com, and a Connecticut-based technology firm while offering digital, content, and marketing consultancy to clients across the country.
Ben has a bachelor’s in Communications and Journalism from Salem State University.
Matt Lazzareschi
Marketing Leader
Josh Parsons
Head of financial
Planning & Analysis
As Head of Financial Planning & Analysis, Josh oversees Wellfleet’s budgeting and financial forecasting and analysis through the design and implementation of predictive and analytical models and facilitates development and monitoring of organizational initiatives and key performance metrics.
Josh joined Wellfleet in 2012. He has been with Wellfleet for his entire professional career, having begun with the company as a Junior Accountant after completing his Bachelor of Science, majoring in accounting, from Western New England University. His history and growth with the company provides a deep understanding of the organization’s systems and procedures.
Jennifer Picard
Internal Communications Manager
As Internal Communications Manager, Jennifer enhances the Wellfleet employee experience by sharing news and info, and leading internal communications and events.
Jennifer joined Wellfleet in 2015, bringing 13 years of experience as a journalist and 7 years’ experience as a manager for communications & fundraising at nonprofits. She has a bachelor’s degree in journalism from Northeastern University.
At Wellfleet, Jennifer is co-chair of WE CARE, serves on the Diversity, Inclusion and Belonging Committee, and is active with several MedPro Employee Resource Groups (ERGs), including as a board member of MedPro Pride. She and her spouse live in Western Massachusetts.
