About
Heath Silverman is a repeat founder, product executive, and strategic operator with a track record of building and scaling technology businesses. As Co-Founder and CEO of Stessa, he built a category-leading asset management platform for residential real estate investors, growing it to serve hundreds of thousands of investors tracking more than $150 billion in real estate assets on the platform.
Heath led Stessa through its acquisition by JLL and later through its next chapter, culminating in its acquisition by Roofstock. This rare two-transaction journey gives him firsthand experience building strategic value, navigating complex M&A, and scaling a company across multiple ownership environments.
As Chief Product Officer at Roofstock, Heath led product strategy, including a company-wide AI transformation. Previously, he was Vice President of Worldwide Business Development and Marketing at Edmodo, where he scaled the platform to more than 70 million teachers and students across 190+ countries. He has also held leadership roles spanning product, sales, marketing, and business development at Amazon, Intel, and multiple startups. Drawing on experience across startups, scaled platforms, and global technology companies, he advises founders on product strategy, AI transformation, growth, strategic positioning, and exit readiness.
"The best exits start with real product strength, disciplined execution, and the right positioning. I help founders build the product foundation and strategic narrative to drive meaningful outcomes."
Schedule a call with an Exitwise advisor to learn more about engaging Heath to Maximize Your Exit™.
Previous Exits
Stessa Sold to JLL
Valuation: Undisclosed
Jones Lang LaSalle (JLL) acquired Stessa in 2018 to help investors better manage income property portfolios. The transaction marked JLL Spark’s first acquisition and validated Stessa’s position as an innovative software platform for real estate investors.
Stessa Acquired by Roofstock from JLL
Valuation: Undisclosed
Following the JLL acquisition, Heath continued to scale Stessa, strengthen its market position, and expand its strategic relevance within the real estate ecosystem. That progress culminated in Roofstock’s acquisition of Stessa from JLL in 2021. By combining Stessa’s asset management software with Roofstock’s single-family rental marketplace, the transaction created a more integrated ownership experience, bringing greater transparency and simplicity to investors buying and managing rental properties.
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Todd Sullivan
CEO, Exitwise
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