Press & Media

Judi Hart is Chief Executive Officer of We Insure, where she leads a national franchise network of independent insurance agencies and the corporate team that supports them. Appointed CEO in July 2025, she joined We Insure in 2024 as Executive Vice President of Operations after six years in senior leadership at parent company PEAK6, where her roles included Chief Operating Officer, Chief People Officer, and Chief Executive Officer of PEAK6 EdTech. Earlier in her career, Judi spent 16 years leading people and culture for some of the world's most recognized brands — serving as Director of Human Resources at Apple, where she oversaw a global media organization of 3,500 employees, and as Vice President of People and Culture at Beats Electronics, helping scale the company from 25 to 750 employees ahead of its acquisition by Apple. She is a graduate of the University of Southern California.

Jay Wolfberg has served as President of We Insure since September 2023, and he leads with the perspective of someone who has built a We Insure agency from the ground up. In 2013, Jay co-founded 2 Jays Insurance Group in Delray Beach, Florida, growing it from a brand-new book of business into the top-producing We Insure agency in the country before stepping down from ownership to lead the organization nationally. He began his insurance career at The Hartford and later served as Director of Sales at PuroClean, where he built a high-performing B2B sales team and helped drive the brand's franchise expansion. As President, Jay focuses on We Insure's three primary customers — agency owners, policyholders, and carrier partners — supporting the growth of existing agencies while expanding the company's footprint nationwide. He holds a Bachelor of Science in Business and Psychology from Nova Southeastern University.

Joe Kurtz is Executive Vice President of Insurance Operations at We Insure, where he leads the operational backbone of the company's fast-growing independent agency franchise network — the systems, processes, and service standards that keep policyholders protected and agency owners supported. With 25 years of experience spanning IT, operations, distribution, claims, and policy administration, Joe brings a rare, full-spectrum view of the insurance business and a data-informed, customer-first approach to solving its most entrenched problems. He is equally comfortable leading a boardroom strategy session and rolling up his sleeves on an operational fix. Naturally curious and always looking for a fresh angle, Joe is helping shape the next chapter of growth at We Insure.

Taylor Luiso is Executive Vice President of Strategy at We Insure, a role he has held since January 2025. He works closely with the executive team to chart the company's long-term growth, bringing capital-markets discipline and transaction experience to how We Insure evaluates expansion, investment, and market opportunities for its franchise network. Before joining We Insure, Taylor spent nearly five years as a trader at PEAK6 Capital Management in Chicago, where he honed the data-driven, decisive approach he now applies to strategic planning. He began his career at Ernst & Young LLP in the firm's Transaction Advisory practice. Taylor is based in Chicago.

Erica Ostrander is Vice President of Markets & Franchise Success at We Insure, where she oversees carrier relations, franchise operations, and the strategic initiatives that help franchise owners across the network grow their businesses. A former We Insure agency owner herself, Erica pairs firsthand agency experience with executive leadership — she knows the franchise model from both sides of the table, and she applies that perspective to strengthening carrier partnerships, improving operational excellence, and creating opportunities for franchise success nationwide. She holds the Registered Professional Liability Underwriter (RPLU) designation. Beyond We Insure, Erica serves as President of the Junior League of Greater Orlando and as Executive Director of the Independent Insurance Agents of Central Florida (IIACF), reflecting her commitment to advancing both her community and the independent insurance industry.

Sonja Broach is Head of Technology and Senior Director at We Insure, where she leads engineering, product, and IT strategy for the company's franchise agency platform and corporate technology organization. She brings more than 25 years of technology leadership across insurance, fintech, energy, healthcare, and e-commerce, including senior engineering roles at GoodLeap, Sunrun, VillageMD (Walgreens), Braintree (PayPal), and Groupon. Throughout her career, Sonja has built a consistent track record of scaling engineering teams, modernizing platforms, and translating AI and automation into measurable business results. At We Insure, she has driven the company's shift toward a technology-first product organization — delivering production systems that generate meaningful operational savings while strengthening security, compliance, and platform reliability across the franchise network.

Cassie Massey is Director of Human Resources at We Insure, where she supports every stage of the team member journey — building culture and driving people strategies that connect directly to business goals. She brings 15 years of insurance industry experience across human resources and talent acquisition, including a decade in leadership roles creating and developing high-performing people teams. Cassie believes HR leadership isn't policy enforcement or compliance management — it's human work, focused on building cultures where people feel respected, seen, and developed. She is also energized by AI and the future of work, thinking critically about how emerging technology can enhance, rather than replace, human-centered talent strategies.