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Six years after HousingWire first celebrated its Tech Trendsetters, this retrospective delves into the enduring legacies and evolving paths of its inaugural honorees. These individuals, initially lauded for their groundbreaking contributions to housing technology in 2019, have continued to sculpt the future of the mortgage and real estate industries. Their journeys from pioneering roles to establishing new ventures and driving digital transformation underscore the dynamic nature of proptech and fintech. The profound impact of these visionaries is evident in the innovative products, companies, and strategies they have championed, demonstrating a sustained commitment to technological advancement within the sector. As the industry evolves, the groundwork laid by these original trendsetters continues to inform and inspire the next generation of innovators.

Erik Bernhardsson, a standout from the 2019 cohort, initially gained recognition as the Founder and CTO of Better.com. There, he revolutionized mortgage processing by developing an automated loan origination system that significantly reduced reliance on traditional loan officers. Under his guidance, Better.com processed nearly $4 billion in loans, reaching a monthly production of $350 million. In 2021, Bernhardsson transitioned from Better.com to launch Modal Labs in New York City. As its Founder and CEO, he now spearheads the creation of sophisticated machine learning infrastructure tools, empowering data teams across various industries with advanced analytical capabilities.

Stacy Hoover, another distinguished honoree, made her mark as the Head of Product at Reali in 2019. Her leadership was instrumental in implementing a scalable market expansion model and introducing an AI-driven Price Predictor tool. She also played a pivotal role in the acquisition of Lenda, an online mortgage lender, and fostered strategic alliances with firms like Hippo Insurance and Lemonade to broaden customer benefits. Today, Hoover serves as the Chief Product Officer at Ellevest, a financial services platform tailored for women, a position she assumed in July 2022. Prior to this, she held a Senior Director of Product role at The RealReal and other key product leadership positions at Reali until March 2021, consistently driving innovation in financial technology.

Mike Cagney, recognized in 2019 as the CEO of Figure Technologies, was at the forefront of integrating blockchain technology into home equity, mortgage, and secondary market lending. His current endeavors include serving as Executive Chairman of Figure Technology Solutions and CEO of Figure Markets, roles he adopted following a significant corporate restructuring in 2024, which spun off Figure Lending. Figure Markets is actively preparing for an initial public offering (IPO), having reported robust revenue growth of 22% year-over-year and achieving profitability in the first half of 2025, signaling continued strong performance in decentralized finance.

Gary Beasley, celebrated as CEO and Co-Founder of Roofstock in 2019, was honored for his visionary approach to transforming single-family rental (SFR) investment. His leadership has been crucial in the expansion of Roofstock's marketplace dominance, further solidified by a merger with Mynd in 2024. Beasley's consistent innovation and impact within the housing sector earned him additional accolades as a HousingWire Vanguard in both 2019 and 2020.

Briana Ings, formerly Briana Whelan, received recognition as Director of Product at Snapdocs in 2019. She spearheaded the development of the company’s digital closing platform, integrating lending and settlement services through automation and AI to streamline hybrid and eClosings. Her innovations reduced in-person closing times dramatically, often to as little as ten minutes. Currently, Ings is the Chief Product Officer at Snappt Inc., a leading document verification platform for the multifamily housing sector. Under her product leadership, Snappt has analyzed over 12 million documents, successfully preventing more than $1.8 billion in potential bad debt, and continues to set benchmarks for fraud prevention in real estate leasing.

The trajectories of these initial Tech Trendsetters vividly illustrate their sustained influence and adaptability within the ever-evolving landscapes of mortgage and real estate technology. Their ongoing contributions highlight a persistent drive to innovate and reshape industry practices. These leaders not only laid significant groundwork for digital transformation but continue to actively participate in pioneering new solutions and strategies. Their careers serve as a testament to the powerful impact of visionaries in propelling technological progress and setting new standards for efficiency and user experience in critical economic sectors.