Mortgage Underwriter

Pylon
Canada
Hybrid

Who this role is best for

Geared toward candidates with deep mortgage underwriting expertise comfortable with acting as a subject matter expert in a fast-paced, collaborative fintech environment.

Best fit for

  • Candidates with hands-on underwriting experience across multiple loan types and a background in fintech or automation.
    — “Experience working on mortgage products within a fintech environment is strongly preferred.”
  • Individuals who thrive in high-agency, debate-driven cultures and take ownership of outcomes.
    — “The people who thrive here have high agency, strong opinions, and a track record of delivering outcomes without direction.”
  • Candidates who can balance compliance rigor with a focus on platform scalability and efficiency.
    — “Comfortable operating in highly regulated industry whilst optimizing for performance.”

Things to consider

  • The role demands a high level of autonomy and initiative, with no explicit mention of mentorship or structured guidance.
    — “We’ll push you to articulate your choices, and defend them where necessary.”

How to stand out

  • Highlight your ability to provide actionable feedback to engineering and product teams during interviews.
    — “You’ll work directly with customers on complex files and give hands-on feedback to our product and engineering teams.”
  • Emphasize your experience with automated underwriting systems and your ability to optimize them.
    — “You’ll act as the expert human judgment behind our automated Decisioning engine.”
  • Showcase your track record of managing third-party fulfillment partners effectively.
    — “Ability to oversee numerous 3rd party fulfillment partners, ensuring high quality, on-time originations.”
Pace · SteadyCollaboration · MediumAutonomy · MediumDecision Impact · Team

Derived from job-description analysis by Serendipath's career intelligence engine.

What success looks like

  • underwriting residential mortgage files
  • issuing clear conditions
  • conducting 2nd level reviews
Typical background
expert-level knowledge of mortgage lending process

Skills & requirements

Required

Mortgage UnderwritingLoan OriginationComplianceCustomer Service

Preferred

Automated Systems OversightFlexible Software Approach

Stack & domain

Mortgage UnderwritingLoan OriginationComplianceRegulatory GuidelinesCustomer ServiceSoftware First Approach3rd Party FulfillmentMortgage OriginationFintechCommunicationCollaborationProblem-solvingStrategic ThinkingTeamworkMortgageUnderwritingRegulatory Compliance

About the role

Original posting from Pylon via Ashby

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.

ABOUT THE ROLE

We’re seeking an entrepreneurial Mortgage Underwriter to join our Platform team. You’ll underwrite loans end to end and act as the expert human judgment behind our automated Decisioning engine, which ensures efficient, compliant loan origination.

You’ll work directly with customers on complex files and give hands-on feedback to our product and engineering teams. That feedback helps the platform handle more underwriting automatically over time.

We are not a traditional mortgage lender. If you’re excited about working with flexible automated systems with rigorous oversight that can scale, this role is for you.

ABOUT YOU

  • Possess expert-level knowledge of the entire mortgage lending process, detailed underwriting knowledge specific to loan requirements and comprehensive understanding of federal, state, and regulatory guidelines related to residential mortgage lending.
  • Comfortable operating in highly regulated industry whilst optimizing for performance. You build with a compliance first lens, respect regulations, continuously review, and update processes as needed.
  • Obsess over the customer and uphold the highest standard. You build for our customers and their borrowers, doing whatever it takes to make them successful on the platform.
  • Adhere to a scalable software first approach, operational workaround last. You surface issues, lead discussions around long-term solutions, document them, and manage temporary manual workarounds if needed.
  • Ability to oversee numerous 3rd party fulfillment partners, ensuring high quality, on-time originations. You build deep relationships and drive consistent results.
  • Have strong, principled opinions that you’re willing to defend. We have a culture of vigorous discussion and debate on decisions. We’ll push you to articulate your choices, and defend them where necessary.
  • Have great ideas, and lots of them. You should see opportunities all around you to make the product and team better. We’ll provide the environment to act on those ideas.

KEY RESPONSIBILITIES

  • Underwrite residential mortgage files across Conventional, Jumbo, Non-QM, and Government products, reviewing credit, income, assets, and collateral against guidelines.
  • Issue clear, accurate conditions and clear them promptly to reduce reconditioning and unnecessary submission turns.
  • Conduct 2nd level reviews, handle exceptions, and manage escalations to ensure quality control.
  • Regularly assess and enhance our Underwriting Systems to ensure smooth file flow, high quality, regulatory compliance and efficiency.
  • Act as a subject matter expert, aiding decision-making and driving product improvement.
  • Work closely with internal teams, partners, and engineering to drive product improvements and optimize the fulfillment infrastructure.
  • Maintain a comprehensive understanding of mortgage origination and regulations to ensure compliance.

REQUIREMENTS

  • 3+ years of experience in underwriting across diverse loan types, including Conventional, Jumbo, Non-QM, and Government across purchase and refinance.
  • Experience working on mortgage products within a fintech environment is strongly preferred.

Source: Pylon careers (Ashby)

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