Gregory Phillips, Deputy General Counsel at Auction.com, has won a 2026 HousingWire Insiders Award. Over the past year, Phillips cleared the legal path to scale SmartSale®, structured the AI agreements that keep the company’s tools running, and advocated with lawmakers and agency staff to improve federal mortgage programs.
“Being named a 2026 HousingWire Insider is a genuine honor,” said Phillips. “It’s a reflection of both the legal team I get to work alongside and a company full of operators, technologists, and leaders who keep pushing this industry forward.”
Scaling SmartSale
Phillips built the legal structure under SmartSale, Auction.com’s program for private sellers who want speed, transparency, and an alternative to foreclosure. Since SmartSale’s formal rollout, overall lead flow has grown 97% year-over-year, and leads have grown more than 1,000% year-over-year from April 2025 to April 2026. SmartSale was named a 2026 HousingWire Tech100 winner and a MortgagePoint Tech Award winner.
Aligning AI use with client requirements
As major financial institution clients discussed broad AI restrictions, Phillips served as lead counsel and worked on each set of terms into carve-outs that satisfy regulatory requirements while preserving Auction.com’s ability to use AI internally. Every request was resolved without disrupting the company’s AI program, and the process now exists as a repeatable framework new clients can follow.
Shaping federal housing policy
For the past seven months, Phillips has spent much of each day advocating with members of Congress, legislative staff, federal and state lobbyists, and industry stakeholders, with a focus on industry programs. As recent federal policy changes created uncertainty across the industry, he helped interpret the changes and proposed approaches to align servicers, agencies, and homeowners without adding regulatory risk. He has framed the effort around a principle broader than any single company’s interest: that federal housing policy should reward transparency and accountability and keep homeowners’ options for loss mitigation, home retention, or an informed transition central.
A record across the platform
Phillips has been at Auction.com since 2011, when he built the legal framework for the live foreclosure auction business at launch. Since then, he has developed and operationalized the Claims Without Conveyance of Title (CWCOT) and CWCOT Second Chance programs, and he designed the architecture that made remote bidding possible for foreclosure sales. Independent analysis published in 2025 estimates that CWCOT has saved the Federal Housing Administration’s (FHA) Mutual Mortgage Insurance Fund more than $10 billion compared with the older conveyance model, and CWCOT now accounts for more than 80% of all FHA dispositions.
“Greg is the person we count on to take our most ambitious, most heavily regulated ideas and find the responsible path to yes,” said George Lane, Chief Legal Officer at Auction.com. “Whether he is scaling SmartSale, getting our AI program right with our clients, or representing the industry’s interests in policy discussions, his judgment is steady and his standards are high.”
Leadership at the intersection of law and operations
Phillips treats regulatory risk as a problem to solve rather than a reason to wait, which is often why a launch on novel ground reaches production. He has mentored two direct reports through bar admission, one of whom now serves as in-house counsel at Auction.com, and supported another in earning real estate licenses.
For Auction.com’s industry partners, the award reflects the legal groundwork behind the programs they rely on.