Ann Dieleman is Managing Director and Co-Founder of Affinity Advisor Group. The consultancy helps executive teams in insurance and financial services build and grow affinity businesses. At Affinity Advisor Group, Ann combines executive coaching, hands-on tools, and real-world experience. Her work helps teams move faster, make better decisions, and grow with confidence. She focuses on the affinity market, where insurers and financial services firms deliver products to members and customer groups. Ann spoke at our 2026 InsurTech Spring Conference on “Winning more Wallet Share in Benefits,” alongside Renee Hamlen, Nelson Lee, and Chris Kaye.
Ann Dieleman brings more than 25 years of executive leadership across insurance and financial services. Before founding Affinity Advisor Group, Ann served as Executive Director and CEO of PIMA. PIMA is a member-driven trade association for insurance and financial services leaders in the affinity market. She led the association for seven years, after years on its executive board. Earlier, Ann spent 16 years at ARAG, an international legal insurance company. As Chief Marketing and Business Development Officer, she led corporate growth, national account strategy, and digital transformation.
Ann also serves as an Independent Board Director at the Global Insurance Accelerator, a mentor-driven program for insurtech startups. She is Managing Principal of Ann Dieleman Consulting as well. Earlier, she was a Lead Business Advisor for Goldman Sachs 10,000 Small Businesses, coaching dozens of owners on growth. Ann holds an MBA from Drake University and a BA in Business and Communications from Simpson College. She is also a Professional Certified Coach through the International Coaching Federation.
For an insurtech audience, Ann brings a leadership advisor’s perspective on the affinity market, executive coaching, go-to-market strategy, benefits distribution, marketing and business development, board governance, and the strategic decisions insurance and financial services teams face when building affinity programs.
