Buying a house contains a peculiar act of emotional misdirection. First comes the browsing: bright kitchens, improbable closets, a deck that makes everyone briefly believe they are the sort of person who owns matching outdoor cushions. Then an offer is accepted and the mood changes. The dream acquires a document checklist. The document checklist acquires a deadline. Somewhere between income verification and the appraisal, joy puts on a lanyard and begins speaking in acronyms. Greg Schwartz has spent the second act of his career staring at this switch. His company, Tomo Mortgage, exists to make it less abrupt.
Schwartz came to the problem after 12 years at Zillow, where he helped turn a young real-estate website into a marketplace business of formidable scale. He joined as vice president of sales in 2007, became chief revenue officer, then chief business officer, and finally president of media and marketplaces. The progression sounds tidy in retrospect. The beginning was anything but. He left a strong job at Time Inc. and CNN for an unknown startup whose name sounded, as he later joked, as if it had something to do with a pillow. The offer involved an 80 percent pay cut and regular travel from New York to Seattle. His first answer was no.
His partner, Lisa, urged him to reconsider. Schwartz eventually managed the rather impressive feat of wooing himself into the job. It became the defining apprenticeship of his career. Zillow began with banner ads and an unruly question: how would a free home-search site become a business? Schwartz built sales teams, shaped products, and worked on the Premier Agent operation that connected agents with potential customers. When he left in late 2019, the company he described had 195 million monthly visitors, 5,300 employees and $1.3 billion in revenue. The unreasonable risk had become a very reasonable biography.
A career spent near expensive decisions
The ostrich lifts its head
Schwartz's farewell to Zillow was titled “My Gap Year and the Ostrich,” though he bargained himself down to a gap half-year almost immediately. It was unusually candid corporate valedictory writing. He thanked the founders, credited Lisa with pushing him toward the original gamble, promised time for Seattle civic work, and suggested friends contact him during ski season in Whistler. Then came the closing line: “Ok time for me to get on my bike.” The bike was literal. Mountain biking remains one of his preferred ways to leave a screen behind.
The pause did not cure him of startups. He had written that he still had another rocket-ship-like company in him. The interesting part was choosing where to point it. Zillow had made looking for a home legible and addictive, yet the transaction beyond the search still caused worry for buyers, sellers, agents, and loan officers. Schwartz saw unfinished business in the mortgage, the moment when a consumer's largest purchase is routed through processes that can feel opaque, repetitive and strangely indifferent to the closing date printed on the contract.
“Our job at Tomo is to smooth out the very jagged edges of the mortgage process.”Greg Schwartz
In 2020 he and Carey Armstrong, another former Zillow executive, co-founded Tomo. The partnership divided the challenge in a useful way. Armstrong brought deep product and housing experience. Schwartz brought revenue, marketplace and customer strategy. They raised a $70 million seed financing announced in 2021. The size of the check attracted attention, but the operating premise was almost domestic: a person buying a home should not have to carry the lender's inefficiency in the form of higher fees, a worse rate or a missed date.
A service business wearing software
Tomo is a nonbank direct lender, not a broker. Its technology automates document work, verification, sales assistance and portions of underwriting, while people remain available for the parts where judgment and reassurance matter. Schwartz's phrasing is plain: computers should do what computers do well, leaving humans to do what humans do well. It is not a manifesto for removing service. It is an attempt to stop trained people from spending their days shepherding paper piles.
That distinction matters because a mortgage is not merely a rate. To the borrower, it is also a clock. A competitive price loses some charm when the appraisal stalls, the requested document changes, or the closing date becomes a theory. Tomo's promise bundles rate, fees and predictability. Schwartz has described traditional mortgage as the catastrophe of the real-estate transaction. The theatrical word suits the emotional stakes: nobody remembers an efficient closing party, but everybody remembers the truck idling outside a house they cannot yet enter.
The name carries the service thesis. Tomo was pulled from omotenashi, a Japanese idea associated with wholehearted hospitality; reverse the first four letters and Tomo appears. It is a rather elegant name for a lender trying to anticipate needs instead of merely reacting to alarms. The company has experimented accordingly, including appraisal coverage and a natural-language home-search product that lets shoppers describe a house with more personality than a row of filters can accommodate.
Schwartz developed one of the better pieces of product research through repetition. He would ask agents and brokers a magic-wand question: if they could fix one thing about mortgage, what would it be? “Fix appraisals” kept coming back, sometimes with what he called a friendly-ish shout. The question is almost comically simple. Its usefulness lies in asking it often enough to hear which complaint arrives with extra force. A dashboard can show a funnel. A shouted answer can show where dignity has left the funnel.
Learning to matter without scale
Founding Tomo also demanded an identity adjustment. At Zillow, a product change could reach a vast audience. At a startup, Schwartz observed during a 2026 industry panel, nobody cares except the founders, hopefully their colleagues, and perhaps their mothers. He said it took years to recalibrate. This is the sort of admission that makes a second act believable. Executive experience transfers. Distribution does not. A respected title cannot make a borrower arrive, trust a lender, upload a bank statement, and tell a friend.
The timing supplied further instruction. Tomo opened for business in June 2021, then mortgage rates climbed and purchase-loan margins tightened. In 2022, the company reduced its workforce by nearly a third. Schwartz addressed the decision publicly and tied it to preserving enough runway for the mission. There was no charming metaphor available. A young lender built for purchase mortgages had met the cycle, and the cycle was not taking questions.
Tomo kept rebuilding. The company invested in automation and AI across sales and loan production. It reported 3.5 times year-over-year mortgage-volume growth during 2024, then raised a $20 million Series B in March 2025 from a group that included Ribbit Capital, DST Global, NFX, Progressive Insurance and Citi Ventures. By 2026, Schwartz said Tomo was approved to lend in 41 states. The trajectory did not erase the hard middle. It made the middle part of the operating system.
Rebuilding the machine
The customer at the center of the room
Schwartz's colleagues describe him as warm, engaging, sharp and possessed of more energy than a hallway strictly requires. They also have an office contest of sorts around who can be the most homebuyer-focused person on the team, a title associated with their CEO and apparently available for theft. The details fit his public style. He speaks in tactile phrases: jagged edges, magic wands, paper piles. Finance has ample vocabulary for making a customer disappear. Schwartz keeps dragging the person back into the sentence.
His argument for transparency is equally commercial. When buyers understand what they are paying and why, trust becomes an advantage. Tomo has made rate comparison and the absence of lender fees central to its pitch. Its 2025 research estimated that American borrowers would collectively pay $11 billion more than necessary that year because mortgage offers vary and comparisons are difficult. The conclusion was gloriously unromantic: shop around. A lender telling customers to compare lenders is either confident, reckless, or both in a productive proportion.
Away from Tomo, Schwartz has served on the CarGurus board since 2018 and sits on its Audit Committee. The connection is apt. Cars and houses are infrequent, expensive purchases wrapped in listings, intermediaries, financing and asymmetrical information. His earlier career at DoubleClick, Yahoo and CNNMoney taught him how attention becomes a business. Zillow taught him how a marketplace earns scale. Tomo asks the later, harder question: once attention has found the dream, who takes responsibility for getting the customer through the door?
There is still an outdoorsman inside the operator. The official version includes mountain-bike trails, skiing and beach time with his family. The more revealing version is the 2019 sign-off, when a long corporate chapter ended and he simply got back on his bike. Schwartz did not ride away from real estate for long. He circled back to its least photogenic hour, when the cushions and kitchen have vanished behind a loan estimate. His wager is that this hour can be designed with the same care as the search that came before it. The paperwork may never become charming. Fewer surprises would be charm enough.