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Technical Oversight – Underwriting

AI Summary
Pylon is seeking a senior mortgage underwriting leader to oversee third-party fulfillment partners and build scalable, compliant loan-origination operations. The role combines underwriting subject-matter expertise with workflow design, quality control, escalation management, vendor oversight, and collaboration with engineering teams. The successful candidate will establish SOPs, SLAs, checklists, productivity standards, and automated processes across conventional, jumbo, non-QM, government, purchase, and refinance loans. This is a high-ownership position in a fast-moving fintech environment that requires deep knowledge of residential mortgage regulations and strong operational judgment.
Remote from
USA
Salary
Undisclosed
Employment
Full Time
Experience
Senior
Published
Apply before
13 Dec 2026
Listing views
50
Application actions
2
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Opportunity details

About this role.

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 Technical Oversight – Underwriting. This role involves both strategic oversight and hands-on management of third party fulfillment providers to ensure efficient, compliant loan origination while enhancing systems and workflows for high-quality, scalable operations.

You will be instrumental in shaping the future of our platform, developing underwriting workflows, standard operating procedures, and quality control measures. You will provide tactical guidance to engineering teams, emphasizing scalable human out of the loop solutions.

We are not a traditional mortgage lender. If you’re excited about building 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.

  • You are a visionary leader with a clear perspective on building scalable, modular origination infrastructure.

  • 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:

  • Develop and implement underwriting workflows, SOPs, SLAs, checklists, and QC measures to ensure high-quality and efficient loan underwriting.

  • Regularly access and enhance our Underwriting Systems to ensure smooth file flow, high quality, regulatory compliance and efficiency.

  • Oversee day-to-day operations with fulfillment partners, ensuring consistent loan delivery.

  • Define and monitor productivity standards and performance goals and ensure that they are met on a monthly, quarterly and annual basis.

  • Conducting 2nd level reviews, handling exceptions, and managing escalations to ensure quality control.

  • Act as a subject matter expert, aiding decision-making and driving product improvement.

  • Working closely with internal teams, partners, and engineering to drive product improvements and optimize the fulfillment infrastructure.

  • Provide technical and guideline training, recommend areas of improvement, and conduct ongoing training as needed.

  • Maintain a comprehensive understanding of mortgage origination and regulations to ensure compliance.

Requirements

  • 10+ years of experience in underwriting and managing underwriting teams across diverse loan types, including Conventional, Jumbo, NON-QM, GOVT across purchase and refinance.

  • Proven track record in developing underwriting workflows, SOPs, SLAs,and QC measures.

  • Proficiency in configuring Underwriting Systems for efficiency,quality and compliance.

  • Proven track record in managing and leading de-centralized underwriting teams.

  • Experience in the management of strategic 3rd party fulfillment partners.

  • Experience working on mortgage products within a fintech environment is strongly preferred.

Benefits

  • Ownership: Meaningful early-stage equity in Pylon.

  • Healthcare: Top-tier medical, vision & dental with support for dependents.

  • 401(k): Ability to save for your future.

  • Flexible Time Off: Be on when you’re on and off when you’re off.

  • Hardware Allowance: $2,000 to fix up your workspace.

  • Annual Off-sites: Fully paid for team off-sites in beautiful corners of the world.

  • At-cost Mortgages: We’ll help you finance your next home when you’re ready.

Apply now >

This job listing has been manually reviewed by the Jobicy Trust & Safety Team for compliance with our posting guidelines, including verification of the company's legitimacy, accuracy of job details, clarity of remote work policy, and absence of misleading or fraudulent content.

Role DNA

A quick view of the complexity, pace, ownership and collaboration implied by the job description.

Job Complexity

5/5
EasyHard

Pace & Pressure

5/5
RelaxedFast-paced

Autonomy Level

5/5
GuidedFull ownership

Communication Load

5/5
IndependentCollaborative
AI insightThe position requires more than 10 years of underwriting leadership experience and accountability for compliance, quality, vendors, and scalable systems. It demands independent decision-making in a highly regulated, high-growth mortgage fintech environment.

Salary analysis

Estimated compensation compared with the broader US market for similar roles.

Estimated job median (per year)Market rate
$190,000
US market range (per year)$160k–$230k
AI insightThe yearly pay period is inferred from the job context; it was not explicitly stated by the employer. No base salary was disclosed. The annual compensation estimate is an AI-generated USD market estimate for a senior US mortgage underwriting and operations leadership role; the yearly cadence is inferred from the full-time senior professional context.

Core skills

Skills and capabilities most closely associated with this opportunity.

Sample interview questions
How have you designed underwriting workflows that improve both quality and turnaround time?

I start by mapping the full file lifecycle, identifying decision points, handoffs, exception paths, and rework sources. I then define clear eligibility rules, checklists, SLAs, escalation thresholds, and QA sampling, measuring results through turn times, defect rates, and investor or audit findings.

How would you manage quality across decentralized third-party fulfillment partners?

I would establish consistent operating standards, scorecards, calibration sessions, and file-level QA reviews across all partners. Regular performance reviews, root-cause analysis, documented corrective actions, and transparent escalation processes help maintain accountability and consistent borrower outcomes.

Describe your approach to second-level underwriting reviews and exceptions.

I evaluate exceptions against documented credit policy, investor guidance, regulatory requirements, compensating factors, and overall risk. My approach is to make decisions traceable, consistently documented, and suitable for audit while escalating policy gaps that require broader governance decisions.

How do you balance compliance requirements with automation and operational efficiency?

I treat compliance rules as product and workflow requirements rather than as manual checks added at the end of the process. I partner with technology teams to encode controls, maintain audit trails, automate validations, and preserve human review for high-risk or ambiguous scenarios.

What metrics would you use to evaluate an underwriting operation?

I would monitor turn time, approval and suspense rates, defect and rework rates, SLA attainment, exception volume, post-close findings, partner productivity, and borrower-impact indicators. These metrics should be segmented by loan type, channel, partner, and underwriter to identify actionable performance patterns.

This analysis is generated from the job description. Salary estimates, role characteristics and sample answers are guidance, not employer-provided facts.
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