Our Leadership
Our executives have a long and successful history within the insurance industry. The stability and expertise of our leadership team helps set us apart, allowing us to provide exceptional service to every client we partner with.
Gary Pearl
Chairman/Chief Executive Officer (CEO), Pearl Companies
Gary joined Pearl in 1985 and currently serves as Chairman/Chief Executive Officer (CEO) of Pearl Companies—a role he took on in 1998. Upon the passing of our founder, Jack Pearl, Gary became Chairman in 2018. Gary provides the Pearl team with a wealth of insurance knowledge and experience, which he developed during his years working in various sales, marketing, and operational divisions at both Pearl Insurance and CIGNA Insurance Company (where he started his career). He remains deeply involved in every aspect of the business and is committed to continuing Pearl’s tradition of innovation. Gary also served as President of the Professional Insurance Marketing Association (PIMA) in 2000.
Dennis Dietrich
President, Pearl Companies
Dennis joined Pearl in 2005 and currently serves as President. With a successful background in finances, strategic planning, direct marketing, and mergers and acquisitions, Dennis oversees strategy execution and operational management for Pearl Companies.
Lisa Hoogerwerf
Chief Administrative Officer, Pearl Companies
Lisa Hoogerwerf joined Pearl in 2012 and currently serves as Chief Administrative Officer. Lisa provides strategic leadership and consultative support in guiding the administrative functions of the company to ensure operational efficiency and organizational excellence. She has responsibility for Affinity Support Services, Compliance and Corporate Training. She collaborates and works closely with other key stakeholders to identify opportunities for improvement, implement best practices, support strategic goals, and contribute to the overall success of the organization. Lisa’s extensive HR background in shaping our people strategy and fostering a culture of collaboration, innovation, and inclusion allows her to build a deeper understanding of how operations, resources, and leadership intersect to drive continued growth and success.
Gary Hickey
President & Chief Sales Officer (CSO), Pearl Insurance
Gary has over 40 years of experience in the insurance industry and has worked for Pearl Insurance and its predecessors for over 30 years. In his role as President & Chief Sales Officer (CSO), Gary oversees the sales, marketing, account relations, and operations of our union-based association clients and our personal insurance division. Additionally, Gary leads sales initiatives for our affinity life and health insurance division. Gary is a member of the Professional Insurance Marketing Association (PIMA) and the American Institute of Professional Association Group Insurance Administrators (AIPAGIA).
Jeff Palmer
Chief Technology Officer (CTO), Pearl Insurance
Jeff Palmer, Chief Technology Officer, oversees all of Pearl Insurance’s information technology operations in our Peoria and Albany locations. Prior to joining Pearl, Jeff managed systems application development teams with a focus on web applications as well as on premise and cloud-based systems including ERP systems that managed human resources, sales, finance, and supply operations. With over 25 years of experience in information technology, Jeff manages Pearl Insurance’s information systems through innovation and ingenuity. He oversees all software development and systems support, infrastructure, telephony, help desk, business intelligence, and Pearl’s project management office. Jeff has had an active Project Management Professional (PMP) certification since 2005.
Douglas Fouts
Chief Marketing Officer (CMO), Pearl Insurance
Doug has more than 25 years of marketing experience and has been pivotal in shaping the company’s marketing strategy over the past decade. As the leader of the Pearl Marketing Group, he oversees the planning, development, and execution of all annual marketing campaigns across the Affinity and Business Lines. His responsibilities include conceptualizing and creating marketing materials, leveraging database-driven strategies for targeted and personalized content, and optimizing campaign results across multiple direct marketing channels. Doug also works with leadership to enhance return on investment (ROI), elevate the Pearl brand, and improve the overall effectiveness of marketing efforts. He directs our marketing team, including design, copywriting, corporate communications, database analysis, and web marketing, while collaborating strategically with other departments across the organization. In addition to his marketing expertise, Doug is deeply committed to leadership development, training, and fostering a positive corporate culture at Pearl Insurance.
Martin Greubel
Chief Operating Officer (COO): Affinity, Pearl Insurance
As the Chief Operating Officer, Marty is responsible for the overall operational efficiency and management of client relationships across our Affinity organization. He has been with Pearl for 18 months as Executive Vice President responsible for the client relations team and continues to lead this area. With over 30 years of experience in the Association and Affinity space, Marty’s leadership and knowledge are invaluable to Pearl.
Jake Pearl
Executive Vice President (EVP): Business Insurance Lines, Pearl Insurance
Jake has been with Pearl for 9 years. He started his career with Zurich Insurance, where he spent several years as a Commercial Underwriter focusing on the Garage Liability space. He also worked as a Commercial Lines Producer after joining Pearl Insurance in 2016. Jake started in Pearl’s Kansas City office before moving home to Peoria in 2021. During his tenure at Pearl Insurance, he’s had varying responsibilities including Direct Sales Supervisor, Automotive Aftermarket Practice Group Leader, BIL Brokered Distribution, and BIL Program Retention. Jake’s current responsibilities within Pearl’s Business Insurance Lines include Distribution, Retention, Underwriting, Service Center, Operations, and Carrier Relations.
Anthony Mancuso
Executive Vice President (EVP): Pearl Insurance
Tony joined Pearl Insurance about 18 years ago and has been leading the CSEA Affinity and Personal Lines business, He’s worked 25 years in the insurance industry, with prior responsibilities as VP of Sales, Outside Sales Director, Inside Sales Director Life/Health & Personal Lines, and Outside Sales Producer. His current responsibilities include overseeing the Affinity Life & Health Sales Team, CSEA Sales and Marketing, Personal Lines sales and retention, and CSEA Client Management. Tony is licensed in both Life & Health and Property & Casualty insurance and has significant experience in sales, marketing, client management, and leadership.
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