Loan number one is a modest quantity to celebrate. It fits on a spreadsheet without troubling the formatting. Yet when Jason Harris announced that Button Finance had originated its first home equity loan in 2020, the small number came with a much longer preparation: roughly ten months of building the company. Before there could be a borrower, there had to be a lender.
Harris paired two accomplishments in that announcement. The team had built a pricing engine. It had also secured mortgage origination licenses. Put those items side by side and the founding story acquires its particular shape. Calculation and permission had to arrive together. A promising piece of software still needed the legal ability to do the thing its screen proposed.
That is a useful place to meet Harris, the New York-based founder and CEO. His business deals with something familiar enough to sound simple: homeowners borrowing against equity in their houses. His career has taken him through several of the institutions that make such borrowing possible, from investment banking and mortgage securities to investment and lending operations. Button puts those experiences on the same desk.
The view from the other end of a mortgage
Harris began his career at Jefferies, working in mergers and acquisitions for financial technology companies and asset managers. He later traded agency and non-agency residential mortgage-backed securities at Amherst Pierpont. Before founding Button, he also worked at Flatiron Investors and served as vice president of operations at PeerIQ. That sequence crosses advisory work, markets, investing and the machinery of a financial business.
A mortgage changes character depending on where you encounter it. A household sees a monthly obligation. A securities trader sees exposure to pools of loans. An operations executive has to consider how information gets from one stage to another. Harris had worked around several of those perspectives before becoming responsible for an enterprise that begins with the individual application.
His educational background includes finance and accounting at NYU Stern. Public professional records also list iOS development study at Flatiron School in 2015. The combination is a small but telling detail in a career that kept moving between finance and technology. Learning how a mobile product is made and understanding how a loan is valued concern different parts of the same eventual transaction.
It would be too tidy to turn every earlier job into a deliberate rehearsal for Button. Careers rarely supply such obliging stage directions. What the sequence does establish is practical familiarity with both financial assets and financial businesses. By 2019, when Button was founded, Harris was moving from work around those businesses into running one of his own.
- JefferiesFintech M&A
- Amherst PierpontMortgage securities
- Flatiron InvestorsVenture investing
- PeerIQOperations
An application with an unusually candid ambition
The borrower problem was explicit in Button’s early recruiting description. A home could be a family’s largest asset while still offering too few ways to access its equity, particularly for borrowers outside prime credit categories. Harris’s company set out to make that access easier. The aspiration concerned the awkward distance between owning an asset and having usable money.
At Money 20/20 in 2021, he offered a product vision with rather less ceremony than the average financial services presentation:
“We want to make it so you can borrow money sitting on the toilet on your phone.”
Jason Harris · 2021
The location does considerable editorial work. It strips the transaction of appointment books, imposing desks and ceremonial paperwork. There is no need to imagine Harris delivering a solemn lecture on convenience when his own chosen image is so efficiently undignified. The ambition was an application ordinary enough to use in an ordinary, if unglamorous, moment.
Convenience also needed a route to customers. In that same conversation, Harris argued that brokers still mattered because borrowers needed to feel informed and comfortable. He saw room for technology and an intermediary together. His preference leaves a human role inside a digital process, particularly where a customer wants help understanding a substantial commitment.
By February 2022, that position had a staffing consequence. Button hired senior account manager Amanda Niswonger to expand its mortgage broker network, alongside account executive Brendan Breitinger. Harris emphasized Niswonger’s industry relationships. The person proposing a phone-based borrowing experience was also hiring people whose value included knowing other people.
The business underneath the button
The product itself helps explain that combination. A home equity loan lets a homeowner borrow against the property’s value. A second lien can sit behind an existing first mortgage. For someone with a first mortgage they want to retain, that creates a different route from replacing the original loan to take out additional cash. The new borrowing still brings its own repayment obligation.
Button offers home equity loans and lines of credit, with fixed and floating rate options. Its website describes combined loan-to-value limits, meaning the existing liens count alongside the new borrowing. Such details are the substance beneath the convenient interface. A short application cannot make the underlying obligations disappear.
The company’s public team includes underwriting, closing, account management and mortgage operations alongside technology. Ashish Dole, its technology and AI architect, has a background in securitized products trading and risk management. The staffing gives Harris’s idea a physical form: people evaluating files, building models and handling the steps between an inquiry and a funded loan.
Another glimpse of his operating concerns appeared in 2023, when he discussed how a lender should respond to an unexpected CFO departure. He stressed acting promptly, deciding which duties an interim executive must cover and identifying the capabilities required in a replacement. Outside providers could help maintain essential finance functions while the search continued.
Those comments were general advice, rather than an announcement about a departure at Button. They nevertheless show where Harris directed his attention when asked about leadership disruption: responsibilities, continuity and specialist knowledge. Someone has to keep the accounts working while everyone else discusses the succession. It is a less photogenic side of entrepreneurship, with an excellent claim on the calendar.
From the first file to the capital markets
In October 2021, Button announced a $2 million seed round. Entities advised by Hildene Capital Management participated, with the money intended for hiring and further technology development. The first-loan milestone had become a business seeking additional capacity. The connection with Hildene would reappear at a later stage.
Harris marked another kind of progress in a public post about the Goldman Sachs transaction GSMBS 2025-CES1. He said $60 million of Button’s older loans were included, making Button the deal’s second-largest contributor. He thanked the team. The figure describes loans in that transaction, rather than the company’s revenue or the amount it had raised from investors.
That distinction matters to his story. The former mortgage securities trader was now discussing loans originated by his own company entering a capital markets transaction. The connection between the beginning and the later milestone is unusually concrete. The instruments he once traded and the business he now operated belonged to the same financial chain.
In May 2025, Button closed a $5 million Series A led by Hildene, with existing investors also participating. Harris described the business as profitable and cash flow positive, and said the financing would support growth while limiting shareholder dilution. The emphasis was as much on how the company financed itself as on the size of the cheque.
The company also reported more than 60 employees and monthly volume that had nearly tripled in six months. Those were company-reported measures at the time of the announcement. They give a dated picture of the operation Harris was running, rather than a permanent description of its size. A funding announcement is a snapshot; the next month still requires running the business.
Round sizes, shown on the same scale. These figures represent company financing, not personal wealth.
The next chapter has other people’s names on it
By June 2026, Button was describing a broader operation, including correspondent programs, wholesale home equity and first-lien Non-QM offerings. It added Bill Twombly to lead fully delegated operations, Jenine Fitter as vice president of client relations and Patrick Kandianis as vice president of business development. Harris linked the hires to supporting growth and serving lending partners.
Their backgrounds explain the selection. Twombly brought experience building a delegated platform at Onslow Bay Financial. Fitter’s career crossed ratings, mortgage finance, capital markets and institutional relationships. Kandianis had led business development at Better Mortgage and partnership sales at Figure Lending. Each appointment addressed a different requirement of a lender working through other lenders and intermediaries.
Harris was also listed on the June 2026 Non-QM conference agenda for a discussion of direct, wholesale and correspondent origination. In July, industry coverage addressed Button’s entry into the Non-QM market. The progression extends the question he faced at the beginning: how to turn an available financial product into a repeatable business with customers, partners and the capacity to process their work.
There is a pleasing imbalance between his most memorable product description and the work around it. On the customer’s side, a phone and a few undisturbed minutes. On the company’s side, licensing, pricing, underwriting, financing and experienced colleagues. Harris’s public milestones keep returning to that second side of the transaction.
The first loan remains a useful measure of everything that followed. It was small enough to count exactly and complicated enough to require ten months of preparation. Harris could finally point to a completed transaction. For a founder building a lender, that was the moment the application became somebody’s loan.