VP, Software Engineering

Guild is hiring a VP of Engineering to lead their product, platform, and foundational engineering teams. This role involves setting technical direction, improving delivery processes, and developing talent while fostering an inclusive engineering culture.

Responsibilities:

• Set technical and organizational direction across product, platform, and foundational engineering — turning Guild’s business strategy into a clear roadmap and putting your teams’ effort where it matters most
• Own how the organization plans and ships — estimation, release readiness, and incident response — improving predictability and throughput with lightweight process, and clearing the blockers that slow teams down
• Balance shipping solid, reliable software with placing growth bets — deciding when to harden core systems and pay down tech debt, and when to fund the experiments that open new growth for members and employer partners
• Own the internal platform and foundational engineering — DevOps, shared services, CI/CD, and testing — so product teams can ship without wrestling the plumbing and the systems underneath stay reliable and secure
• Lead through ambiguity to outcomes — bring clarity to messy problems, decide with incomplete information, and keep teams focused on measurable impact as priorities shift
• Develop leaders and talent — coach and grow multiple Directors and Engineering Managers, set clear expectations, give frequent and actionable feedback, and create stretch opportunities so your people do the best work of their careers
• Build an inclusive, sustainable engineering culture — psychologically safe teams, a modern and AI-forward way of working, and a pace people can keep
• Partner across the company — work closely with Product, Design, and Data & AI engineering leaders, and represent engineering with executives and key vendors (e.g., AWS, Auth0) to align technical investment with company priorities

Requirements:

• Proven ability to lead a multi-team engineering organization at the VP level — setting direction across several domains and owning outcomes across both product and platform engineering
• Demonstrated people-leadership as a manager of managers — you set clear standards, drive execution and remove blockers, grow talent through frequent, actionable feedback, and build psychologically safe, inclusive teams
• Comfort operating in ambiguity and driving to outcomes — you simplify complexity, make practical trade-offs with incomplete information, and orient teams around measurable impact rather than activity
• Deep technical credibility — you can weigh architectural decisions on their merits and earn the trust of senior engineers — plus the judgment to balance reliable, cost-aware systems with room for growth bets
• Strong cross-functional partnership — you build trust with Product, Design, and peer engineering leaders, and explain technical strategy and trade-offs clearly to both engineers and executives
• Experience scaling consumer or B2B2C growth-product engineering and/or internal developer platforms in a high-growth environment
• Familiarity with a modern AWS serverless stack (e.g., Lambda, Aurora), GraphQL, and the tooling that supports an AI-native software development lifecycle
• Experience leading engineering through an AI-native transformation — building with AI as a first class citizen, agentic workflows, and platform guardrails responsibly
• Background partnering with Data/AI engineering to ship AI-native product experiences