About the role- Lead and own multiple client engagements end-to-end, from ideation and technical discovery through to production
- Prototype rapidly while ensuring long-term reliability, maintainability, and security
- Balance multiple concurrent engagements, context-switching between different technical stacks and business domains
- Contribute to the Headstart Platform roadmap by identifying and delivering the highest-leverage investments across our tooling and infrastructure
- Shape client strategy by reframing problems, influencing priorities, and defining what the right path forward looks like
- Be the technical authority in sales and scoping conversations
- Grow the engineers around you and raise the floor of every project you work on
Your background- 7+ years of professional software engineering experience with a track record of owning complex, high-stakes systems end-to-end
- Been the technical authority in rooms with executives and clients and have shaped what got built, not just built what you were told
- Experience creatively applying AI in the development lifecycle, and knowing when not to
- Enjoys a fast-paced and collaborative environment
- Have owned client relationships at the executive level: running discovery, navigating difficult conversations, and earning trust quickly
- Proven full-stack depth: backend services (Python), datastores, React/Next.js, optionally ML
- 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 $240,000 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.
