Hometap Appoints Jesse Silverman as General Counsel and Josh Berg as Chief Product Officer as It Enters Its Next Stage of Company Growth

Executive appointments align with Hometap’s ongoing expansion across product and regulatory engagement

BOSTON--(BUSINESS WIRE)--Hometap, the Boston-based financial technology company pioneering home equity financing solutions, today announced two senior appointments to its executive leadership team, welcoming Jesse Silverman as General Counsel and Josh Berg as Chief Product Officer. Silverman will report to Hometap Chief Executive Officer, Jeffrey Glass, and Berg will report to Hometap President and Chief Operating Officer, Sarah Dekin.

These strategic hires reflect Hometap’s continued investment in building a durable foundation for growth as the company develops its product platform and continues its engagement with regulators and industry participants. Berg and Silverman join Hometap’s leadership team to oversee product development and the company’s legal and compliance functions as the company advances its homeowner-focused solutions and shapes best practices across the home equity investment market.

“Hometap’s growth has been driven by a focus on building solutions that reflect the financial realities homeowners are navigating today,” said Jeffrey Glass, CEO of Hometap. “These leadership additions help ensure our approach to homeowner-first product development continues to evolve while maintaining the standards and practices that support trust across the industry.”

Jesse Silverman, General Counsel

Silverman joins Hometap as General Counsel with extensive experience advising financial services and fintech companies on state and federal regulatory matters. He began his career in senior roles in state government at the Connecticut Department of Banking and at the Consumer Financial Protection Bureau, where he helped establish the agency’s Office of Enforcement. His experience also includes serving as General Counsel and Chief Compliance Officer for several fintechs. Most recently, he served as outside counsel to several financial technology companies, guiding them from early product development through market deployment and integrating compliance programs across departments. At Hometap, Silverman will lead the company’s legal and compliance functions and advise the executive team on regulatory engagement, corporate governance, and the management of outside counsel.

“As home equity solutions become more widely used, clear standards and strong consumer protections are increasingly important,” said Silverman. “Hometap has taken an active role in engaging with regulators and policymakers, and I look forward to helping advance legal and compliance frameworks that protect consumers and support the long-term health of the industry.”

Josh Berg, Chief Product Officer

Berg joins Hometap as Chief Product Officer with more than a decade of experience helping high-growth tech companies scale their products and product organizations, most recently serving as Vice President of Product at ResortPass and previously as Chief Product Officer at ezCater. Prior to that, he held senior product leadership roles at CarGurus, where he led consumer product and digital retail, and at Wayfair, where he led the storefront product team across U.S. and international brands. Across these roles, Berg focused on simplifying complex user experiences and building products that earn consumer trust. At Hometap, Berg will lead the company’s product and design organizations, overseeing product strategy, homeowner experience, and the evolution of the homeowner-facing platform.

“Our role is to meet homeowners where they are and help them understand the choices available to them,” said Berg. “Hometap has built a strong foundation of homeowner-first solutions, and I'm excited to help scale and evolve our platform to serve homeowners' changing needs."

Berg and Silverman join Hometap amid the company’s continued growth, following a 2025 milestone of surpassing $2 billion in home equity investments deployed to more than 22,000 homeowners and a $50 million funding round later that year.

About Hometap

Founded in 2017, Hometap is a Boston-based fintech company on a mission to make homeownership less stressful and more accessible. Starting with its industry-leading home equity investment product, the company has helped over 24,000 homeowners across the U.S. access their home equity without taking on additional monthly payments or selling their home. Hometap expanded its suite of innovative financial products and services in 2022, introducing a centralized dashboard that enables homeowners to easily track their home equity, receive guidance and support from experts, and protect and grow the value of their home. Learn more at hometap.com.