The $13 trillion mortgage industry at the core of the American economy runs on broken assembly lines with human-powered workflows, stitched-together software, and a series of capital markets intermediates. The costs to originate are at an all time high despite foundational shifts in technology.
Pylon is rewiring mortgages from the ground up. We are building the only API-first, programmatic infrastructure that fully automates credit, compliance, capital, and operations. For the first time, originators can build and scale mortgage businesses entirely through software, not people. Our team comes from Stripe, Better, and Affirm, and we are backed by Conversion Capital, QED, Citi, Fifth Wall, Peter Thiel, and the founders of Ramp, Mercury, Blend, and others.
Were hiring a Founding Chief of Staff to help drive Pylons growth and execution. Youll work directly with the CEO and leadership team on the companys most critical priorities: owning strategic initiatives, unblocking day-to-day operations, and helping the business scale faster and more intelligently.
This is a high-impact, high-visibility role for someone who thrives in ambiguity, loves solving hard cross-functional problems, and wants to help build a generational company from the earliest stages. Youll wear many hats and have a seat at the table as we scale across product, GTM, capital markets, partnerships, and operations.
Lead high-priority initiatives across the business, from strategy through execution, across product, ops, GTM, and capital
Serve as a thought partner to the CEO and leadership team, surfacing insights and driving execution at the companys core
Build and improve operating cadences across functions (e.g., planning, OKRs, hiring processes, board materials)
Identify and solve operational bottlenecks to improve execution velocity and alignment
Support special projects such as fundraising, strategic partnerships, or new product rollouts
Dive into the weeds when needed to get things across the finish line, especially where playbooks dont exist yet
Help create structure and processbut only where it meaningfully accelerates the business
46 years of experience in high-performing, analytical environments (e.g., top-tier consulting, VC-backed startups, investment banking, or equivalent roles)
Experience in a BizOps, Chief of Staff, or generalist role at a high-growth startup is a major plus
Exceptionally structured thinker and communicator; you turn chaos into clarity
Unafraid of messy problems and incomplete data and comfortable making calls without certainty
Known as someone who executes relentlessly and can be trusted to own complex work end-to-end
Strong written communicator and comfortable synthesizing findings for execs, investors, and cross-functional teams
Scrappy and resourceful: you do what it takes to get the job done and move the business forward
Low ego, high agency: youre excited to roll up your sleeves and do unglamorous work if it means accelerating the mission
Bonus: Familiarity with mortgage, lending, or capital markets is great, but not required
As the founding member of the BizOps team, youll be at the center of Pylons most important decisions and initiatives. This is an opportunity to work alongside exceptional people, build foundational systems from the ground up, and help shape the future of one of the most valuable and least modernized industries in the U.S.
If you want to be in the room where the company is builtthis is it.
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