Sr. Technical Project Manager (Remote Opportunity)

First American • Santa Ana, IL

1d • Remote

About The Position

Join a team that puts its People First! As member of First American's family of companies, Mortgage Solutions provides lenders with solutions to originate, close and service quality loans. Since 1889, First American (NYSE: FAF) has held an unwavering belief in its people. They are passionate about what they do, and we are equally passionate about fostering an environment where all feel welcome, supported, and empowered to be innovative and reach their full potential. Our inclusive, people-first culture has earned our company numerous accolades, including being named to the Fortune 100 Best Companies to Work For® list for eleven consecutive years. We have also earned awards as a best place to work for women, diversity and LGBTQ+ employees, and have been included on more than 50 regional best places to work lists. First American will always strive to be a great place to work, for all. For more information, please visit www.careers.firstam.com. Be part of a transformative, high-visibility initiative at the center of First American's technology strategy. We are modernizing a mission-critical document generation platform that serves mortgage origination clients across the country. This legacy monolithic platform — currently running on-premises in a data center — is being completely re-architected into a cloud-native, microservices-based system. The program spans three concurrent engineering workstreams and more than 40 engineers, making this one of the most complex and consequential technology programs underway at the company. We are seeking a Senior Technical Project Manager who thrives at the intersection of engineering, business stakeholders, and program delivery. This is not a coordinator role — this person will be a strategic delivery leader who partners closely with engineering managers, architects, and product owners to drive execution, surface risk early, and keep 40+ engineers aligned and unblocked across three parallel workstreams.

Requirements

• Bachelor's degree in Computer Science, Engineering, Information Systems, or a related technical field; equivalent work experience will be considered.
• 8+ years of experience in technical project or program management, with at least 3 years managing large-scale platform modernization, re-architecture, or cloud migration programs.
• Demonstrated experience leading programs with 30+ engineers across multiple concurrent workstreams.
• PMP certification required; PgMP or equivalent program-level certification strongly preferred.
• CSM (Certified Scrum Master) or SAFe certification preferred.
• Solid working knowledge of microservices architecture, cloud-native design patterns, and distributed systems — sufficient to engage meaningfully with engineers and architects, ask the right questions, and understand technical tradeoffs.
• Familiarity with cloud platforms (AWS, Azure, or GCP) and the operational considerations involved in migrating from on-premises data center environments.
• Understanding of API design, service decomposition strategies, and the challenges of brownfield-to-greenfield migration including strangler-fig patterns, data migration, and dual-run operations.
• Experience with DevOps tooling, CI/CD pipelines, and modern software delivery practices; ability to track engineering health metrics (cycle time, deployment frequency, defect rates) as proxy indicators of delivery health.
• Expert-level command of Agile and hybrid delivery methodologies; ability to operate across Scrum, Kanban, and SAFe frameworks simultaneously.
• Proven ability to build and maintain integrated program schedules with complex cross-workstream dependencies.
• Strong command of program management tools including Jira, Confluence, Smartsheet, MS Project, or equivalent.
• Experience managing program budgets, forecasting costs, and producing financial variance reports.
• Track record of managing risk in large, high-stakes programs where failure carries significant business or client impact.
• Proven experience planning and executing client migrations or platform transitions in a B2B environment — coordinating directly with external clients, not just internal teams. (Required)
• Demonstrated ability to build and manage client migration wave plans, runbooks, and cutover playbooks for multi-account migration programs. (Required)
• Experience designing and managing structured UAT and testing programs with external clients — including test planning, environment coordination, defect lifecycle management, and formal sign-off processes. (Required)
• Comfort operating as a client-facing representative of an engineering program; ability to communicate technical migration concepts clearly and confidently to non-technical business audiences. (Required)
• Exceptional written and verbal communication skills; ability to translate engineering complexity into clear, concise business language for executive audiences.
• Strong facilitation skills for steering committees, cross-functional working sessions, and technical decision meetings.
• Demonstrated ability to build trust and influence without authority across matrixed engineering and business organizations.
• Comfort with ambiguity and organizational complexity; ability to create structure and clarity in fast-moving programs.
• Track record of holding teams and stakeholders accountable while maintaining collaborative, productive working relationships.

Nice To Haves

• Prior exposure to document generation systems, origination platforms, or financial services technology is a strong plus.
• Experience managing dual-run or parallel-operation periods during platform cutover, including output validation strategies and confidence-gate frameworks. (Strongly Preferred)
• Familiarity with financial services or mortgage industry client onboarding processes, compliance considerations, or data sensitivity requirements relevant to platform migrations. (Strong Plus)
• Experience managing migration pipelines across many accounts simultaneously, including wave scheduling, readiness tracking, and client-level status reporting. (Preferred)

Responsibilities

• Own end-to-end delivery of a multi-year legacy platform modernization program, spanning three parallel workstreams: legacy decomposition, microservices build-out in the cloud, and client migration/cutover.
• Define and maintain a master program roadmap, integrating workstream-level sprint plans into a single coherent view of progress, dependencies, milestones, and risks.
• Establish and operate a structured program cadence including workstream standups, cross-team syncs, steering committee reviews, and executive status reporting.
• Drive release and deployment planning in coordination with engineering leads, DevOps, and infrastructure teams to manage data center decommission timelines and cloud cutover windows.
• Partner with product, architecture, and engineering leadership to maintain a prioritized and realistic backlog, ensuring commitments are grounded in team capacity.
• Actively manage cross-workstream dependencies — including shared services, data contracts, API versioning, and integration checkpoints — to prevent blockers before they impact delivery.
• Facilitate alignment across three engineering workstream leads, ensuring sequencing of work is logical, risks are shared, and decisions are made at the right level with the right people.
• Identify and resolve resource contention, scheduling conflicts, and technical integration bottlenecks across teams.
• Track program-level scope changes, assess impact to schedule and budget, and escalate or adjust plans as needed.
• Proactively identify technical, operational, and business risks inherent in a brownfield-to-cloud migration at scale; develop mitigation and contingency plans.
• Maintain a living RAID log (Risks, Assumptions, Issues, Dependencies) and drive resolution ownership across stakeholders.
• Escalate blockers and decisions that require senior leadership attention; prepare crisp briefings with clear options and recommendations.
• Facilitate Go/No-Go decision gates for major milestones including cloud environment readiness, workstream integrations, and client cutover events.
• Serve as the primary communication bridge between engineering teams and business stakeholders including product leadership, mortgage operations, client services, and executive sponsors.
• Produce and deliver high-quality program status reports, executive dashboards, and milestone summaries tailored to the audience.
• Establish and enforce lightweight but effective governance frameworks appropriate for a large agile engineering program.
• Partner with the PMO to ensure the program meets standards for budget tracking, change control, and reporting cadence.
• Own the end-to-end client migration program plan — from initial migration readiness assessment through phased onboarding, parallel run, cutover, and legacy decommission — ensuring each client transitions on a clear, agreed-upon timeline with minimal disruption.
• Serve as the primary point of coordination between internal business stakeholders (mortgage operations, client services, product, compliance, and support) and external mortgage origination clients throughout the migration lifecycle.
• Build and maintain per-client migration runbooks, cutover checklists, and rollback plans in partnership with engineering leads and client-facing teams; ensure all parties understand their roles and responsibilities at each gate.
• Develop and manage a structured client testing program including UAT planning, test environment provisioning coordination, defect triage, sign-off workflows, and resolution tracking — working jointly with clients and internal QA teams.
• Facilitate client onboarding kickoffs, migration planning workshops, and regular status syncs; produce client-facing status communications and escalation reports tailored for non-technical audiences.
• Coordinate dual-run operations — managing the period where clients operate on both legacy and cloud platforms simultaneously — including parallel output validation, discrepancy reporting, and confidence-building checkpoints before full cutover.
• Track client migration pipeline across all accounts; maintain a migration wave schedule that balances engineering capacity, client readiness, and business priority; escalate schedule risks to leadership with clear options and recommendations.
• Partner with client services and account management to manage client expectations, address concerns proactively, and ensure a white-glove migration experience that reinforces client confidence in the platform transition.
• Champion a delivery culture of transparency, accountability, and continuous improvement across all three workstreams.
• Facilitate retrospectives, lessons learned sessions, and process improvement cycles to increase delivery velocity over time.
• Support onboarding of new engineers and workstream leads into program norms, tooling, and ways of working.
• May be required to perform duties outside of normal work hours based on business needs.

Benefits

• Based on eligibility, First American offers a comprehensive benefits package including medical, dental, vision, 401k, PTO/paid sick leave and other great benefits like an employee stock purchase plan.

What This Job Offers

• Job Type: Full-time
• Career Level: Mid Level
• Number of Employees: 5,001-10,000 employees