Technical Oversight

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 a Technical Oversight - Processing with deep mortgage operations experience and strong independent judgment. This is not a traditional customer support or relationship-only role. You will act as a senior operational partner to our originating customers, owning issue resolution end-to-end and ensuring loans move cleanly, compliantly, and predictably through the lifecycle.

You will work directly with customers while collaborating closely with underwriting, processing, product, and engineering to reduce errors, prevent rework, and improve system-driven workflows. This role is ideal for someone who has worked inside the loan file, understands where mortgages break, and is motivated to help build scalable, automated systems that eliminate those failures over time.

We are not a traditional mortgage lender. If you’re excited about operating with rigor today while helping design the future of automated mortgage infrastructure, this role is for you.

Key Responsibilities

Client & Origination Ownership

• Act as a operational point of contact for originating customers, owning issue resolution from identification through closure

• Guide customers through the full loan lifecycle, providing clear, accurate direction on requirements, timelines, disclosures and next steps

• Own the operational health of assigned loans end-to-end, ensuring files progress on schedule and close on time by proactively identifying blockers, driving resolution, and coordinating across internal teams and customers.

• Proactively manage customer expectations to reduce inbound escalations and uncertainty

Operational Judgment & Risk Prevention

• Independently evaluate loan scenarios to identify potential structural, disclosure, or compliance risks before they escalate

• Catch missing, inconsistent, or incorrect inputs that could lead to redisclosures, delays, or downstream rework

• Provide firm, professional guidance to customers when corrections or process adherence are required

Cross-Functional Collaboration

• Partner closely with underwriting, processing, and closing teams to ensure clean handoffs and aligned execution

• Serve as a trusted escalation point, reducing leadership involvement by resolving complex or high-stakes issues directly

• Coordinate with third-party vendors to ensure issues are addressed efficiently, quickly and accurately

Systems & Product Feedback

• Identify recurring patterns, edge cases, and workflow gaps that impact loan quality or customer experience

• Collaborate with Product and Engineering to help define requirements, guardrails, and operational acceptance criteria

• Contribute real-world mortgage insight to improve automation, tooling, and system-driven decisioning

Documentation & Quality

• Maintain clear, accurate documentation of customer interactions, decisions, and follow-ups

• Ensure customer-facing communication aligns with regulatory requirements, internal standards, and operational best practices

Qualifications

• 7+ years of mortgage industry experience, with hands-on roles in processing, underwriting, or a similar operational function

• Direct experience working loans from application through CTC and closing

• Hands-on experience with mortgage disclosures, including preparing, reviewing, or validating LEs and CDs, with a strong working knowledge of TRID timing, tolerance categories, and re-disclosure triggers.

• Ability to independently sanity-check loan structure, including LTV, product eligibility, and basic compliance considerations

• Prior experience serving as an escalation point for brokers, borrowers, or loan officers

• Comfortable operating in fast-moving, ambiguous environments where processes are still being built

• Excellent written and verbal communication skills, with the ability to explain complex mortgage concepts clearly and confidently

• High attention to detail paired with strong problem-solving instincts and sound judgment

What This Role Is Not

• This is not a call-center or script-based customer support role

• This is not a traditional CSM focused only on relationship management

• This is not a sales or loan officer role — there are no commissions or volume-based incentives

• This role requires independent mortgage judgment, ownership, and accountability

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