Engineering Manager

Why this role exists (and why now)

Sched is a profitable, $5M ARR event management platform with a clear path to $15M+. Customers rely on us to run complex, multi-day, multi-track events around the world.

The business is healthy. The product is proven.

Engineering execution is the constraint today, which makes it the biggest opportunity to unlock the company’s next chapter.

Fixing this unlocks a different future for the company: faster delivery, higher confidence in execution, and a platform the business can evolve quickly and responsibly in an AI-accelerated world.

We’re hiring a senior engineering leader to run a focused turnaround: tighten delivery, restore reliability, and modernize a long-lived codebase without putting the business at risk.

This role is for someone who has done this kind of work before and knows what it takes:

• clarifying ownership and expectations
• raising quality and delivery standards
• making tough calls on scope, people, and process
• modernizing in phases that keep customers stable
• getting a team shipping predictably again

If you’re looking for a mature, already-scaled engineering org, this will feel frustrating.

If you’ve led a reset and you want to do it again with a real product and real revenue, this is a rare opportunity.

The mission

Your mission is to lead an engineering turnaround that makes the company meaningfully faster and safer.

You will:

• restore predictable shipping through clear ownership and standards
• increase reliability and operational confidence
• modernize the platform pragmatically while continuing to ship product
• shape architecture and data foundations so AI can be built into the product, not layered on later
• build an AI-enabled development workflow and prepare the platform to operate effectively in an AI-accelerated era of software development

Success looks like fewer surprises, clearer timelines, calmer operations, and a platform the team can evolve quickly with confidence.

What you’ll focus on

Engineering leadership & accountability

• Lead a small, mixed team of full-time engineers and contractors

• Establish clear expectations around ownership, quality, and delivery

• Address underperformance and role clarity directly and constructively

• Build a culture of accountability, learning, and follow-through

  Outcome: a team that ships predictably and takes responsibility for results

Modernization & AI enablement

• Assess a long-lived PHP codebase and identify what truly matters to fix

• Modernize in phases that support business momentum

• Use AI tools (Copilot, Cursor, Claude, etc.) as force multipliers for documentation, refactoring, testing, and design

• modernize in a way that treats our event and scheduling data as long-term context for AI-driven features

  • avoids brittle architectures that block AI adoption later
  • enables experimentation with AI-native product capabilities without destabilizing customers
  • assumes AI will be implicit in future product decisions, not a side initiative
  • Outcome: A platform that’s easier to change, safer to ship, and set up for AI-native product work, with Sched’s event and scheduling data treated as the long-term advantage.

Delivery, reliability & business impact

• Improve observability, incident response, and operational confidence

• Partner with Product, Revenue, and Ops to align scope, sequencing, and tradeoffs

• Translate technical decisions into clear business implications

  Outcome: fewer surprises, clearer timelines, and stronger execution across the company

This job is not for you if…

• You’re looking for a fully mature, well-oiled engineering organization
• You avoid tough people or ownership decisions
• You prefer consensus over decisiveness when delivery slips
• You optimize for shiny tech rather than business outcomes
• You want influence without accountability

This job is for you if…

• You’ve led or been part of a real engineering turnaround
• You enjoy bringing order to ambiguity
• You can balance pragmatism with ambition
• You’re excited by making a legacy system AI-ready
• You want your work to materially change how a company grows

What we offer

• OTE (base + variable): $120k–$190k USD
• Base salary range: $120k–$150k depending on experience
• 401(k) with 5% match
• Medical, dental, and vision through Aetna
• Life insurance
• 25 days PTO
• 100% remote, global team
• Schedcations: company-paid team gatherings in places like Morocco, Japan, Cambodia, and Colombia. Part work, part adventure.
• Real ownership, real influence, and room to grow with the company

Hiring process

• Initial screen: Alignment on role, expectations, and compensation
• Deep dive: CEO conversation and cross-functional panel
• Working session: A practical walkthrough of a real scenario from our world, followed by references and an offer if it’s a mutual yes