Senior Director, Software Engineering

Strategic Leadership & People Management 

• Lead and grow the Funding & Payments engineering team, with a defined path to expanding ownership across the full Pros Financing & Payments engineering organization 

• Mentor engineering managers and senior ICs, building a high-performance, accountable engineering culture 

• Own hiring, calibration, and career development for a team operating in an expanding domain 

• Define and communicate a multi-quarter engineering roadmap tied to underwriting, funding, and payments outcomes 

Technical Leadership 

• Own the architecture and reliability of systems spanning underwriting decisioning, submission and approval workflows, funding, and payments processing 

• Guide technical decisions across a distributed, event-driven services ecosystem supporting high-volume, time-sensitive financial transactions 

• Set and enforce engineering standards for security, compliance, and auditability appropriate to a regulated lending and payments environment 

• Champion modern engineering practices — including AI-assisted and agentic development workflows — to raise team velocity and quality 

Cross-Functional Execution 

• Partner with Product, Risk, Compliance, and Operations to align engineering delivery with contractor-facing financing and payments outcomes 

• Own delivery across initiatives spanning multiple services and teams, balancing speed, risk, and system stability 

• Define and track KPIs across financing/payments transaction volume, submission-to-close conversion, and fraud/delinquency risk metrics 

Process & Platform Maturity 

• Drive CI/CD, observability, and deployment automation across the Financing & Payments service estate 

• Manage technical debt and platform scalability as transaction volume and product surface area grow 

• Establish the operating rigor — on-call, incident response, SLAs — required for systems that gate real money movement 

• 10+ years of engineering experience, including 5+ years in technical leadership roles managing managers and cross-functional teams 

• Proven track record leading engineering for complex, regulated fintech, lending, or payments platforms 

• Deep experience with distributed, event-driven microservices architectures supporting high-volume transactional systems 

• Experience with underwriting/decisioning systems, loan origination or servicing pipelines, or payments processing infrastructure 

• Strong grasp of cloud-native architecture (AWS or equivalent), API design, and modern CI/CD practices 

• Track record of scaling an engineering organization through growth — hiring, structuring teams, and expanding scope 

• Excellent stakeholder management and communication skills, comfortable operating across Product, Risk, and Compliance 

• Experience in point-of-sale financing, home improvement/solar lending, or contractor-facing fintech 

• Experience integrating AI or agentic tooling into the software development lifecycle to improve engineering throughput 

• Background scaling a platform team from a single product line into a broader organization — mirroring this role's growth path