Technical Oversight - Processing

The $13 trillion mortgage industry at the core of the American economy runs on broken assembly lines with human-powered workflows, stitched-together software, and layers of capital markets intermediaries. Origination costs are at an all-time high despite foundational shifts in technology.

Pylon is rewiring mortgages from the ground up. We are building the only API-first, programmatic infrastructure that fully automates credit, compliance, capital, and operations. For the first time, originators can build and scale mortgage businesses through software, not people.

Our team comes from Stripe, Better, and Affirm, and we’re backed by Conversion Capital, QED, Citi, Fifth Wall, Peter Thiel, and the founders of Ramp, Mercury, Blend, and others.

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.

• 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
  

• 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

• 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

• 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

• 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

• 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

• 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

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