Chief of Staff, Operations

About Pylon

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.

About the role

We’re hiring a Founding Chief of Staff to help drive Pylon’s growth and execution. You’ll work directly with the CEO and leadership team on the company’s 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. You’ll wear many hats and have a seat at the table as we scale across product, GTM, capital markets, partnerships, and operations.

You will

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 company’s 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 don’t exist yet

Help create structure and process—but only where it meaningfully accelerates the business

About you

4–6 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 : you’re 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

Why this role matters

As the founding member of the BizOps team, you’ll be at the center of Pylon’s 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 built—this is it.

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