Engineering Manager – Modernization & AI Enablement

Engineering Manager – Modernization & AI Enablement

Join to apply for the Engineering Manager – Modernization & AI Enablement role at SCHED
.

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.

Location: Remote
Role Type: Full-Time
Reports To: CEO

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

• 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.

• 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.

• 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. Outcome:
Engineering becomes a trusted, proactive partner to every team.

• 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

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

Seniority Level

Mid‑Senior level

Employment Type

Full‑time

Job Function

Software Development

Additional Information

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