Head of Talent

About the role

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.

What You'll Own

• 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).
• 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.
• 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.
• 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.
• 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.
• 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.

What We're Looking For

• 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.
• Bonus: 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.

Your First 90 Days

• 30 days: Learn the bar. Sit in on interviews, audit the current pipeline and spend, map open roles against our growth plan, and identify where we're losing candidates and money.
• 45 days: Stand up the in-house sourcing motion, replace the most expensive contingent dependencies, ship a structured interview process and scorecards for engineering, and tighten onboarding.
• 60 days: Have a measurable, compounding pipeline for engineering and key functions, a clear hiring plan and budget for the next phase of growth, and the first hires of your own team in motion.

What You Get

• 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.
• Cheap compensation: competitive base + meaningful equity.