Technical Oversight - Underwriting

Pylon; San Francisco (CA); On-site; USD 120,000 - 160,000; Full time

Benefits offered by this job

Meaningful early-stage equity

Top-tier healthcare

401(k) programs

Flexible Time Off

Hardware Allowance

Annual off-sites

At-cost Mortgages

Job summary

Pylon in San Francisco is looking for a Technical Oversight – Underwriting professional to manage third-party fulfillment providers and ensure compliant loan origination. You will build high-quality workflows and be a key player in shaping the platform.

Ideal candidates will have over 10 years of experience in various loan types and a deep understanding of regulatory requirements. Pylon offers a dynamic work environment with opportunities to make a significant impact.

Qualifications

• 10+ years of experience in underwriting and managing teams.
• Proven track record in developing workflows and quality control measures.
• Experience managing strategic 3rd party fulfillment partners.

Responsibilities

• Develop and implement underwriting workflows and SOPs.
• Oversee day-to-day operations with fulfillment partners.
• Conduct second-level reviews and manage escalations.

Skills

Expert-level knowledge of mortgage lending process

Visionary leadership

Compliance and regulatory knowledge

Customer-focused approach

Ability to build strong relationships

Job description

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 buildingAmerica’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 a 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.