Apply on company website New York, NY; Toronto, Canada Hybrid Full-time USD 265,000 / year

HEADSTART is hiring a Staff, Applied AI Engineer

Responsibilities

  • Lead multiple client projects from initial planning through to live implementation
  • Develop quick prototypes without compromising long-term system stability, security, or ease of maintenance
  • Manage several active projects simultaneously, adapting to different technologies and industry contexts
  • Help shape the future of internal tools by identifying and building high-impact platform improvements
  • Guide client direction by redefining challenges, setting priorities, and determining optimal solutions
  • Serve as the technical expert during sales discussions and project scoping sessions
  • Elevate team performance by mentoring peers and improving the quality of every initiative

Benefits

  • Comprehensive benefits package
  • 401k retirement plan with employer contributions
  • Employer-paid medical, dental, and vision insurance
  • Monthly allowance for wellness activities
  • Daily complimentary meals at the NYC office
  • Citi Bike membership and pre-tax transit benefits
  • 12 weeks of parental leave with optional phased return at half-time

Work Arrangement

Hybrid — NYC, Toronto

Other

  • Applicants who don’t meet every listed requirement are still encouraged to apply.
  • Although the role is advertised as hybrid in NYC or Toronto, fully remote candidates in the US or Canada may be considered for exceptional matches.
Job Details
Location New York, NY; Toronto, Canada
Work mode Hybrid
Employment Full-time
Salary USD 265,000 / year
Department Engineering
Category other
Posted 7 months ago
Application On company website
About company
HEADSTART logo

We build custom AI systems.

We use deterministic software and LLMs to create flexible, understandable systems designed for human oversight, not rigid automation.

We start by deeply understanding your company, your perspective, and your constraints to deliver meaningful business outcomes.

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