Engineering Manager – Modernization & AI Enablement

Engineering Manager – Modernization & AI Enablement Location: Remote Role Type: Full-Time Reports To: CEO THE OPPORTUNITY Sched is a profitable $5M ARR event management platform on a path to $15M+. We’re evolving our engineering organization to blend strong technical leadership with modern, AI-assisted development practices. We’re looking for an Engineering Manager who can guide a small team through the realities of a 15+ year legacy system while helping us move toward a more efficient, AI-enabled future. This role is hands-on enough to understand the system, but senior enough to lead people, set standards, and partner across the business. If you enjoy modernizing systems, improving engineering workflows, and coaching engineers to get more leverage with modern tools; this role is an excellent fit. THE MISSION Your mission is to increase engineering throughput and product reliability without linearly increasing headcount. You’ll do this by combining: • clear technical leadership • structured modernization work • pragmatic use of AI-assisted development tools (Copilot, Cursor, Claude, Replit, etc.) This is about making the work faster, safer, and more predictable. FIRST 30 DAYS: ESTABLISH REALITY Before we accelerate anything, we need a clear map of the system. In your first three months, you will: • Assess the current PHP codebase and infrastructure • Identify legacy areas, high-risk sections, and modernization priorities • Document technical debt in a way the business can act on • Define where AI tools can realistically speed up documentation, refactoring, and testing • Establish a predictable development workflow that blends human judgment + AI output • Build a modernization plan we can execute in phases alongside normal product work This creates the foundation for the company’s next stage of growth. KEY RESULT AREAS 1. Engineering Leadership & Team Development • Lead and coach a small engineering team with clear expectations • Help engineers adopt and use AI tools effectively • Build a culture of accountability, learning, and ownership • Hire, retain, and develop strong talent Outcome: A team that ships predictably, works collaboratively, and uses modern tooling with confidence. 2. Technical Delivery & Modernization • Improve the health of our legacy PHP system through structured cleanup and documentation • Reduce technical debt in a prioritized, business-aligned manner • Use AI tools for code explanations, prototypes, tests, and refactors • Work with Product to scope work realistically and unblock roadmap items Outcome: A more stable, understandable system with fewer surprises and faster delivery. 3. Reliability, Observability & Security • Strengthen logs, monitoring, and alerting • Partner with Business Operations to ensure secure use of AI tools • Reduce incident frequency and improve time-to-resolution • Maintain strong on-call and incident management practices Outcome: Higher reliability and more predictable customer experience. 4. Cross-Functional Collaboration • Work closely with Product to align on scope, sequencing, and priorities • Partner with Sales and Customer Success to understand customer needs and unblock revenue • Plan around Schedmin and other internal tools so product work, back office workflows, and data all stay in sync • Identify where automation or lightweight middleware solves problems faster than core engineering • Communicate tradeoffs clearly to business partners Outcome: Engineering becomes a trusted, proactive partner to every team. CORE REQUIREMENTS • Experience leading engineers in a SaaS environment (1–3 years is great if your IC background is strong) • Strong technical foundation in PHP or similar web stacks • Experience modernizing or refactoring legacy systems • Comfortable jumping into code when needed • Deeply integrates AI into daily engineering workflows so it’s a default part of how you design, code, review, and communicate • Clear, proactive, and direct communicator who surfaces risks early, thinks upstream, and translates impact for internal and external users • Strong prioritization, sequencing, and tradeoff skills; can explain what moves now versus later and why • Bias toward action and iterative improvement Apply tot his job