Lead Forward Deployed Product Manager

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.

Every customer runs their mortgage business a bit differently. They have their own systems, teams, and ways of serving borrowers, and Pylon only works if it fits into how they actually operate.

We’re hiring a Lead Forward Deployed PM to embed with our most strategic customers, learn their business from the inside, and build Pylon into the way they work. You’ll spend time with their loan officers, operations teams, and engineers, figure out how loans really move through the organization, and map out how to put Pylon at the center of it.

This is a senior role. You’ll work directly with customer executives and technical leaders, take charge of complicated, high-stakes projects, and push them to real results, even when that means asking customers to change how they work.

You’ll also be the link between our customers and our product team. What you learn in the field will shape what we build, and how quickly you get customers live will have a direct impact on Pylon’s growth.

• Embed with strategic customers, on site and remotely, to understand their teams, systems, and full mortgage workflow

• Map how each customer works today, figure out where Pylon adds the most value, and put together a plan that gets them live quickly

• Own each integration from scoping and solution design through data mapping, configuration, testing, and launch, working with their engineers and ours

• Find the manual steps, workarounds, and bottlenecks in each customer’s process and replace them with Pylon

• Write and ship code yourself, including integrations, scripts, configurations, internal tools, and agents on our platform, and commit changes to our core codebase when a customer needs them

• Bring what you learn back to the product team. You’ll figure out which requests are one-offs and which should become part of the core platform, and work with product to build them

• Be the person accountable for each engagement. You’ll work directly with customer executives and technical leaders to set goals, get everyone aligned, make the hard calls, and hold both sides to the results

• Advise customer leadership on how to modernize their mortgage operations, and work with GTM and Account Management to support deals, grow relationships, and make sure customers succeed

• Define and track what success looks like for each customer, including time to go live, adoption, loan volume, and efficiency gains

• Build playbooks and reusable tools so every integration goes faster than the last

• Set the standard for how Pylon deploys, and help hire, mentor, and grow the forward deployed team

• Use AI in your day-to-day work

• You have strong opinions and you’ll defend them, including with customers. We argue about decisions a lot here, and we’ll ask you to explain your thinking and stand behind it. We also expect you to change your mind when someone shows you you’re wrong.

• You’re ruthless about priorities. Customers will ask for everything. You focus on what gets them live and what creates the most value, and you’re comfortable saying no to good ideas that come at the wrong time.

• You’re comfortable in a heavily regulated market. Compliance is non-negotiable for us. We work with regulators to push the industry forward and get better outcomes for borrowers. We play by the rules, and we play to win.

• You care a lot about our customers and their borrowers, and you hold a high bar for them. We’ll do whatever it takes to make them successful on Pylon.

• You default to software over manual work. One of our guiding principles is that anything in the backend mortgage process done by a human is a bug, and you’ll see more of these bugs than anyone else at Pylon. When we need a temporary workaround, you flag it, write it down, and push for the real fix.

• You’re good with people. You’ll work with everyone from loan officers and operations teams to engineers and executives, at our customers and inside Pylon, and you know how to build real relationships and get results through them.

• You have a lot of ideas. You notice things that could be better about the product, our customers, and the team, and we’ll give you room to act on them.

• You’re willing to get into the weeds. You can learn mortgage quickly enough to sound like a 20-year veteran, and you can learn each customer’s business as well as their own team knows it.

• 8+ years in software, in roles like forward deployed engineering, solutions engineering, technical product management, or management or implementation consulting

• You’ve led complicated, high-stakes enterprise projects from scoping through launch and delivered measurable business results

• You’ve worked directly with C-suite executives and senior technical leaders, and they listen to you

• You’re comfortable taking charge in the room, delivering hard news, and keeping large groups aligned

• You write code and are comfortable committing to a production codebase, working directly with customer engineering teams, and working with APIs and data

• You’re great at understanding complicated business workflows and turning what you learn into clear product requirements

• You’re comfortable with ambiguity and with juggling several customers at once

• You can write SQL

• You’ve built or deployed 0-1 enterprise software in a regulated industry

• You’re willing to travel regularly to customer sites

• Nice to have: mortgage, lending, or fintech experience, or experience with mortgage systems like loan origination systems

We don’t expect you to be a mortgage expert on day 1. Over time, though, you’ll need to become one of the most trusted mortgage experts on the team to do this job well.

Must live in or be willing to relocate to Palo Alto (CA) or New York City.