[All remote jobs](https://jobicy.com/jobs.md)[![Pylon logo](https://jobicy.com/data/server-nyc0409/galaxy/mercury/2026/11/3f9f8b3a3cdb-221.webp)](https://jobicy.com/company/pylon.md)[Pylon](https://jobicy.com/company/pylon.md) # Technical Oversight – Processing AI Summary Pylon is seeking a senior mortgage operations specialist to oversee loan processing for originating customers. The role owns issue resolution across the loan lifecycle, identifies disclosure and compliance risks, and coordinates with underwriting, closing, product, engineering, and external vendors. Candidates need substantial hands-on experience with mortgage files, TRID, Loan Estimates, Closing Disclosures, and loan-structure review. This is a high-accountability position in a fast-moving startup focused on automating mortgage infrastructure.[Apply for this job](#job-application)[View company](https://jobicy.com/company/pylon.md)ShareRemote from[USA](https://jobicy.com/job-region/usa.md)SalaryUndisclosedDepartment[Product & Operations](https://jobicy.com/categories/management.md)EmploymentFull TimeExperienceSeniorPublished12 Nov 2026Apply before12 Dec 2026Listing views42Application actions1Application toolkit ## Make your next move. Prepare your resume, explore your fit, and draft a cover letter for this opportunity. Opportunity details ## About this role. About [Pylon](https://jobicy.com/company/pylon.md) 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 Show more [Apply now >](https://jobicy.com/jobs/161538-technical-oversight-processing.md) > Annual salary information is not provided for this position. Explore salary ranges for similar roles in our [Salary Directory ›](https://jobicy.com/salaries.md) * ![Upload CV](data:image/svg+xml;base64,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) ### Upload your resume now To unlock remote work opportunities and be discovered by global employers. 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 5/5EasyHard ### Pace & Pressure 5/5RelaxedFast-paced ### Autonomy Level 5/5GuidedFull ownership ### Communication Load 5/5IndependentCollaborative AI insightThe role requires at least seven years of mortgage operations experience plus independent judgment on complex loan, disclosure, and compliance issues. It combines customer-facing escalation ownership with cross-functional operational and product feedback responsibilities in an ambiguous startup environment. ## Salary analysis Estimated compensation compared with the broader US market for similar roles. Estimated job median (per year)Market rate$130,000US market range (per year)$110k–$155k0$170.50k AI insightThe yearly pay period is inferred from the job context; it was not explicitly stated by the employer. No base salary is disclosed. The annual compensation figures are estimated for a senior US-based mortgage processing and operational oversight role requiring deep TRID, disclosure, and end-to-end loan lifecycle expertise; the yearly period is inferred from the full-time US professional role context. ## Core skills Skills and capabilities most closely associated with this opportunity. [Mortgage processing](https://jobicy.com/jobs?search_keywords=Mortgage%20processing.md)[Loan lifecycle management](https://jobicy.com/jobs?search_keywords=Loan%20lifecycle%20management.md)[TRID compliance](https://jobicy.com/jobs?search_keywords=TRID%20compliance.md)[Loan Estimates](https://jobicy.com/jobs?search_keywords=Loan%20Estimates.md)[Closing Disclosures](https://jobicy.com/jobs?search_keywords=Closing%20Disclosures.md)[Mortgage disclosures](https://jobicy.com/jobs?search_keywords=Mortgage%20disclosures.md)[Loan-to-value analysis](https://jobicy.com/jobs?search_keywords=Loan-to-value%20analysis.md)[Loan file review](https://jobicy.com/jobs?search_keywords=Loan%20file%20review.md)[Risk identification](https://jobicy.com/jobs?search_keywords=Risk%20identification.md)[Escalation management](https://jobicy.com/jobs?search_keywords=Escalation%20management.md)[Customer communication](https://jobicy.com/jobs?search_keywords=Customer%20communication.md)[Cross-functional collaboration](https://jobicy.com/jobs?search_keywords=Cross-functional%20collaboration.md)[Operational documentation](https://jobicy.com/jobs?search_keywords=Operational%20documentation.md)[Workflow improvement](https://jobicy.com/jobs?search_keywords=Workflow%20improvement.md)[Mortgage underwriting coordination](https://jobicy.com/jobs?search_keywords=Mortgage%20underwriting%20coordination.md) Sample interview questionsHow do you identify and prioritize risks in a mortgage loan file before they delay closing?I review the file against product eligibility, LTV, income and asset documentation, disclosure timing, and outstanding conditions. I prioritize risks by their potential impact on compliance, redisclosure requirements, closing dates, and borrower experience, then assign clear owners and deadlines for resolution. Describe your experience with TRID disclosures and redisclosure triggers. I have worked with Loan Estimates and Closing Disclosures throughout the loan lifecycle, validating timing requirements, tolerance categories, and material changes. When a change may trigger redisclosure, I document the facts, confirm the applicable requirement with the right stakeholders, and communicate the revised timeline clearly to the customer. How would you handle a broker escalation involving an incorrect loan input that may affect closing? I would first confirm the facts and assess the downstream effect on underwriting, disclosures, and closing. I would explain the required correction professionally, coordinate the internal teams needed to implement it, and provide the broker with a concise action plan and status updates until the issue is closed. How do you turn recurring operational problems into product improvements? I document the pattern, quantify its operational impact, and separate user errors from workflow or system gaps. I then provide product and engineering with representative examples, expected behavior, edge cases, acceptance criteria, and practical guardrails that can prevent recurrence. What does strong ownership mean in a fast-moving mortgage operations environment? Strong ownership means treating a problem as mine from identification through closure, even when multiple teams are involved. I proactively surface blockers, make sound decisions within my authority, escalate only when needed, and ensure that customers and internal partners understand the next steps and final outcome. Next step ## Apply now. 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