Engineering Manager – Modernization & AI Enablement

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

THE OPPORTUNITY

Sched is a profitable event management platform ($5M ARR, targeting $15M+). We are evolving our engineering organization to integrate strong technical leadership with modern, AI-assisted development practices.

We are seeking an Engineering Manager capable of guiding a small team through the challenges of a 15+ year legacy system while driving the transition toward an efficient, AI-enabled future. This role requires a blend of hands-on technical understanding, senior leadership skills, standard setting, and cross-business partnership.

If you excel at modernizing systems, improving engineering workflows, and coaching engineers to leverage modern tools, this role is an excellent fit.

THE MISSION

Your primary mission is to increase engineering throughput and product reliability without requiring linear headcount growth. You will achieve this by combining:

• Clear technical leadership.
• Structured modernization work.
• Pragmatic use of AI-assisted development tools (Copilot, Cursor, Claude, Replit, etc.).

The goal is to make the work faster, safer, and more predictable.

FIRST 30 DAYS: ESTABLISH REALITY

To build the foundation for the company’s next stage of growth, your first three months will focus on assessment and planning:

• Assess the current PHP codebase and infrastructure.
• Identify legacy areas, high-risk sections, and modernization priorities.
• Document technical debt clearly for business stakeholders.
• Define where AI tools can realistically accelerate documentation, refactoring, and testing.
• Establish a predictable development workflow blending human judgment and AI output.
• Build a phased modernization plan executable alongside normal product work.

KEY RESULT AREAS

1. Engineering Leadership & Team Development

• Lead and coach a small engineering team with clear expectations.
• Help engineers effectively adopt and utilize AI tools.
• 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.
• Collaborate 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 systems.
• 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 to keep product work, back office workflows, and data synchronized.
• 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 beneficial if IC background is strong).
• Strong technical foundation in PHP or similar web stacks.
• Experience modernizing or refactoring legacy systems.
• Comfortable jumping into code when necessary.
• Deeply integrates AI into daily engineering workflows for design, coding, review, and communication.
• 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; ability to explain execution rationale.
• Bias toward action and iterative improvement.