Head of Talent

Pylon • San Francisco, CA

1d • Onsite

About The Position

About Pylon
America’s $13T mortgage market is one of the most important financial systems in the world. It underwrites the middle class and is the mechanism through which millions of families build wealth. But while every other financial instrument has been simplified to an API call, mortgages are still assembled by hand.
We started from zero and created the first vertically integrated mortgage platform that turns origination into a single API.
Publicly traded companies and the country’s largest originators are already building on Pylon. Revenue is compounding monthly. We’re backed by Peter Thiel, Conversion Capital, QED, Citi, Fifth Wall, and the founders of Ramp, Blend, and Mercury.
Working at Pylon isn’t for those seeking comfort. The people who thrive here have high agency, strong opinions, and a track record of delivering outcomes without direction. Many of us are former founders. We move quickly, challenge each other directly, and take full ownership of results. It’s hard work, but it will be worth it.
Join us in building America’s mortgage rails.
Why this role exists
We've outgrown an agency-and-contractor approach to hiring. It's expensive, it's fragmented, and it doesn't compound. We need someone to build Pylon's talent function as a real, owned, in-house engine: one that consistently lands exceptional engineers and operators, faster and cheaper than the market, and makes Pylon a place those people never want to leave.
You will be our first dedicated talent leader. You're not inheriting a machine; you're building one. If you do this well, you become one of the highest-leverage people in the company.

Requirements

• You've built or substantially scaled an in-house talent function at a high-growth startup (ideally somewhere between seed and Series C), and you've done it for technical, hard-to-fill engineering roles in a competitive market.
• You are high agency and a player-coach. You can personally source and close a brilliant, hard-to-get engineer and design the process that lets ten other people do it. You don't wait for a system to exist; you build it.
• You think from first principles and you're contrarian-and-correct. You have strong opinions about hiring, you're right more than you're wrong, and you'll push back on leadership when you should.
• You can sell a hard mission. You make ambitious people want to take a risk, and you tell Pylon's story in a way that resonates with the best.
• You are data-driven about pipeline, conversion, comp, and headcount, comfortable owning the numbers in a board and investor context.
• You care about culture and retention as much as req-filling. You measure success in great people who stay and do their best work, not just offers signed.
• You thrive in-person, in ambiguity, at intensity. This is a hard, fast, high-stakes environment. You read "this will be hard" as a feature, not a warning.

Nice To Haves

• Experience in fintech, infrastructure, or regulated industries.
• A track record of cutting agency/contingent spend by building internal sourcing.
• Experience standing up and managing offshore/distributed sourcing teams.
• You've helped a company scale through a period of rapid growth and capital raises.

Responsibilities

• Build the in-house talent engine. Stand up sourcing, pipeline, and full-cycle recruiting as an internal capability. Wean us off contingent agencies and per-hire fees, build a sourcing motion that compounds, and hire/lead a small team (recruiters, sourcers, including offshore support) as volume demands.
• Steward the culture. As we scale into our next phase of growth, you are a primary guardian of who we are: put customers first, think big, practice craftsmanship, deliver results. Protect the bar and the culture as the headcount grows.
• Make engineering hiring the priority. Mortgages may be the hardest problem in tech: real money, real regulatory complexity, real stakes. Our engineers own entire systems, not tickets, and work across AI/ML and operations research. Your first mandate is landing more of them. Then scale the same rigor across GTM, operations, compliance, and G&A.
• Own the full funnel and raise the bar. From first touch to signed offer: structured interviewing, calibrated scorecards, fast and decisive process, and a relentlessly high bar. Speed and craftsmanship are not in tension here; we expect both.
• Build the employer brand and candidate experience. Make Pylon's story impossible to ignore to the people we want, and make every candidate interaction reflect "craftsmanship in everything," including the ones we don't hire. Own our careers' presence and how we show up in the market for talent.
• Own onboarding, ramp, and retention. Hiring is half the job; keeping people is the other half. Standardize onboarding so new hires are productive on day one, and build the rituals, growth paths, and feedback loops that make great people stay and do their life's work here.
• Run the systems and the numbers. ATS, hiring metrics, time-to-fill, pipeline health, headcount planning with leadership, comp and leveling frameworks, and the HR/onboarding ops stack (e.g. Rippling). Bring data, not vibes.

Benefits

• Substantial ownership. Be a founder, not just an employee, with meaningful equity in Pylon.
• Comprehensive health, dental, and vision for you and your dependents.
• Access to Pylon's industry-leading home financing rates.
• 401(k) and financial planning support.
• The chance to build the team behind America's mortgage rails, and to make Pylon the place where the best people in the country want to do their life's work.
• Compensation: competitive base + meaningful equity.

What This Job Offers

• Job Type: Full-time
• Career Level: Entry Level
• Education Level: No Education Listed