Head of Engineering

At Pylon, we’re re-wiring the entire mortgage stack from application to loan settlement with programmatic infrastructure.

As our Head of Engineering, you’ll lead a team of talented engineers in designing, building, and scaling the company’s multi-product platform. This is a hands-on leadership role where you’ll help set technical direction, mentor engineers, and collaborate cross-functionally to deliver robust, scalable solutions to enterprise customers.

We're in search of people who find difficult problems invigorating and who fit well into a high-performing team built on mutual respect and reliance. This is a high-impact position for someone who thrives in a startup environment, enjoys solving technical challenges, and is excited to help shape the future of Pylon.

About you

Partnering closely with our CTO, you will:

• Set the course—together. Shape the engineering roadmap in partnership, balancing speed, quality product, and reliable architecture that compounds.

• Reinforce high performance. We hold a high bar for talent and expect you to elevate it. You'll have hard conversations and push the team to deliver exceptional results.

• Keep us shipping on time. You enable the team to execute on schedule by sweating the details and making high quality, on-the-fly decisions.

• Scale the team. Help recruit top-tier technical talent. Exceptional engineers respect you and want to follow what you do next.

• Own uptime & trust. Ensure we meet enterprise-grade SLAs and compliance requirements—Pylon is business-critical infrastructure for our customers.

• Bridge the business. Work cross-functionally with Product, Capital Markets, and Compliance to translate complex mortgage workflows into elegant APIs that delight developers.

• Stay hands-on. Dive into code reviews, prototypes, or thorny production issues when needed; technical credibility is non-negotiable.

• Represent Engineering. Communicate engineering priorities and risks to the broader team and customers translating deep tech into crisp business value.

• Lead our forward-deployed motion. Some customers partner with us to help the build on our APIs. You'll manage those projects and build the playbook.

• Do your life's work. We seek those who are here to build a generational business through craftsmanship. You must have a deep desire to win.

About the Team

What we’re not:

• Building a CRUD app:

  • We’re building a platform that’s only possible due to deep technology investments and thinking hard from first principles. Cargo-culting what’s come before won’t be sufficient.

  • If you’re looking to do mostly plumbing / lego piece assembling, Pylon may be very frustrating for you.

• A GPT wrapper:

  • Mortgage is a sprawling mess of problems that demand precision, and there isn't one tool that solves every one of them. We use LLMs, but we've reached for tools in multiple disciplines like mixed-integer linear optimization and programming language research.

• An easy job:

  • We’re building a lot of things from the ground up for the first time. Working at Pylon is like a research project where you have to ship to intelligent, opinionated customers regularly.

  • It’s basically guaranteed you’ll be handed a task that is too difficult for you to do. You might fail sometimes. You might have no idea where to start. Our team leans heavily on each other, but there’s no getting around the difficulties.

What we are:

• A small team:

  • We don’t have an army of engineers. If you find something is broken, you are probably the best one to fix it

  • All the code we write has to punch above its weight in maintainability and toil reduction

  • If you have a good idea, you have much more ability to put it into action than at a large company

  • We need generalists: specialization is for big companies that already have everything figured out. If you’re smart, flexible and like getting into everything, we want you.

• Working in a regulated space:

  • Mortgage is regulated both federally and at the state level.

  • We move fast, but breaking things isn’t an option.

About the Job

Basics

• Job title: Head of Engineering

• Stock options: own meaningful equity

• Health insurance, dental, vision, etc

Our technology stack:

• Typescript front and backend

• Web components

• GraphQL

• PostgreSQL

• NestJS web framework

• Nx build system

• Sagittarius

• AWS stack using CDK for declarative infrastructure

• General philosophy: monolith until it hurts. If we can do something without introducing a new service, we will

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.