Senior Director, Software Engineering

GoodLeap•Austin, FL

About The Position

GoodLeap's B2B organization builds the technology that powers the GoodLeap Pros platform — the end-to-end software contractors use to run their businesses, accessed through the Pros web and mobile clients, APIs, MCPs, and the DeDe agent. Within B2B, Pros Financing & Payments owns every point-of-sale financing and payments capability contractors and their customers touch: underwriting, submissions, approvals, pricing, funding, and payments, along with the product configuration and documents infrastructure that supports them. The Senior Director of Software Engineering will lead the Funding & Payments engineering team, owning the architecture, delivery, and operational health of the systems that decide, fund, and process contractor transactions. This is a hands-on technical leadership role for someone who can architect resilient, high-throughput financial systems while building and scaling the team accountable for them.

Requirements

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

Nice To Haves

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

Responsibilities

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
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
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
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