Senior Software Engineer

Department: Engineering

Location: New York, NY, Toronto, Canada

Compensation: $200K • Offers Equity

Employment Type: FullTime

About the company

Headstart is built for people who want to think like founders. We work inside real enterprises ($100M+ ARR) shipping production AI systems that change how they operate. Every engagement is a different industry, a different problem, and a different set of constraints. You leave each one knowing that business deeply.

We've built our own agent Friday, which powers the majority of how we deliver. We're bootstrapped, cash-flow positive, and growing fast.

Why join us

The engineers who thrive at Headstart are the ones who want to understand how businesses work, not just how code works. We take the work seriously and the culture deliberately. Pay is transparent, weekends are yours, and we don't confuse long hours with good work.

About the role

• Own client engagements end-to-end, from technical discovery and scoping through to production

• Work directly with enterprise clients, translating ambiguous business problems into concrete technical scope

• Ship production AI systems across multiple domains and stacks: agents, LLM workflows, document processing, and the infrastructure that makes them reliable

• Contribute to Friday and the Headstart Platform via patterns, skills, and infrastructure that compound across every engagement

• Raise the bar for the engineers around you through code review, pairing, and shared standards

Your background

• 5+ years of engineering experience with a track record of owning systems end-to-end

• Comfortable in client-facing situations, running discovery, earning trust quickly, and shaping what gets built

• Your instincts and standards are contagious and teammates adopt them naturally

• You use AI tools constantly, creatively, and with good judgment about when not to

• Proven full-stack depth: backend services (Python), datastores (SQL/NoSQL), optionally React/Next.js

• Experience designing distributed systems, APIs, data pipelines, or developer productivity infrastructure at scale

• Bonus if you’ve been a founding engineer or startup early hire, with history building production products from scratch

• Bonus if you’re NYC based — we have a loft office in Soho and provide lunch and snacks

Note: Even if you don't meet all the requirements, we still encourage you to apply. This role offers extensive benefits, a base salary of $200,000 USD plus competitive equity compensation, 401k with employer match, fully covered medical, dental, and vision premiums, monthly wellness stipend, free lunch everyday in our NYC office, Citi Bike + pre-tax commuter benefits, and 12 weeks parental leave with an optional 4-week ramp-up at a 50% schedule.

While this position is listed as hybrid in NYC or Toronto, we are open to considering fully remote candidates based in the US or Canada for the right fit.