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 Client Success, Originations Oversight and Supervision 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
Pylon
https://pylon.com