Quick Summary
Senior Engineering Leader, Platform Turnaround & Modernization (Remote)
Why This Role Exists
Sched is a profitable event management platform ($5M ARR, clear path to $15M+), relied upon globally for complex, multi-day events. Currently, engineering execution is the primary constraint. We are seeking an experienced Senior Engineering Leader to execute a focused turnaround, tightening delivery, restoring reliability, and modernizing a long-lived codebase without risking business stability.
This is a rare opportunity for a leader who thrives on resetting engineering organizations, raising quality standards, and driving predictable shipping with real product and revenue backing.
The Mission: Faster, Safer Engineering
Your core mission is to lead an engineering turnaround that significantly increases the company's speed and safety profile. Key objectives include:
- Restoring predictable shipping through clear ownership and defined standards.
- Increasing reliability and operational confidence across the platform.
- Pragmatically modernizing the platform while maintaining product delivery momentum.
- Shaping architecture and data foundations to ensure AI capabilities are built into the product, not layered on later.
- Building an AI-enabled development workflow to operate effectively in an AI-accelerated era.
Success is measured by fewer surprises, clearer timelines, calmer operations, and a platform that the team can evolve quickly and confidently.
Core Focus Areas
Engineering Leadership & Accountability
- Lead a small, mixed team of full-time engineers and contractors.
- Establish clear expectations regarding ownership, quality, and delivery standards.
- Address underperformance and role clarity directly and constructively.
- Cultivate a culture defined by accountability, continuous learning, and follow-through.
Modernization & AI Enablement
- Assess the long-lived PHP codebase to prioritize critical fixes and modernization efforts.
- Implement modernization in phases that actively support business momentum.
- Utilize AI tools (e.g., Copilot, Cursor, Claude) as force multipliers for documentation, refactoring, testing, and design.
- Ensure modernization treats Sched’s event and scheduling data as the long-term context for AI-driven features.
- Enable experimentation with AI-native product capabilities without destabilizing customer experience.
Delivery, Reliability & Business Impact
- Significantly improve observability, incident response, and overall operational confidence.
- Partner closely with Product, Revenue, and Operations teams to align scope, sequencing, and tradeoffs.
- Translate complex technical decisions into clear business implications.
Candidate Profile
This role is ideal for you if:
- You have successfully led or been integral to a real engineering turnaround.
- You enjoy bringing order and clarity to ambiguous situations.
- You can effectively balance pragmatism with ambitious goals.
- You are excited by the challenge of making a legacy system AI-ready.
- You want your work to materially influence company growth.
Compensation and Benefits
This is a 100% remote position with a global team.
- OTE (Base + Variable): $120,000–$190,000 USD (Base salary range: $120,000–$150,000, depending on experience).
- 401(k) plan with a 5% company match.
- Comprehensive medical, dental, and vision coverage through Aetna.
- Life insurance.
- 25 days of Paid Time Off (PTO).
- Schedcations: Company-paid team gatherings in international locations (e.g., Morocco, Japan, Cambodia, Colombia).
- Real ownership, significant influence, and substantial room for growth.