Senior Applied AI Engineer for Enterprise AI Systems

Urban Ridge Supplies; Toronto; Hybrid; CAD 191,000 - 318,000; Full time

Benefits offered by this job

401k with employer match

Medical, dental, vision insurance

Monthly wellness stipend

Free lunch in NYC office

Citi Bike + pre-tax commuter benefits

Parental leave (12 weeks) with 4-week

Job summary

Headstart seeks an experienced engineer to own client engagements end-to-end, from discovery to production of AI systems across multiple domains. You will translate enterprise problems into concrete technical scopes and ship reliable AI solutions, contributing to platform patterns and infrastructure.

Expect collaboration across teams, code reviews, and a high standard of engineering excellence. The role values strong full-stack ability with Python, SQL/NoSQL, and optional React/Next.js, plus

Qualifications

• 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.

Responsibilities

• 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.

Skills

Full-stack depth

End-to-end ownership

Client-facing/discovery

AI tools usage

Distributed systems design

Startup/early-hire experience

Tools

Python

SQL/NoSQL

React/Next.js

Job description

Headstart seeks an experienced engineer to own client engagements end-to-end, from discovery to production of AI systems across multiple domains. You will translate enterprise problems into concrete technical scopes and ship reliable AI solutions, contributing to platform patterns and infrastructure.

Expect collaboration across teams, code reviews, and a high standard of engineering excellence. The role values strong full-stack ability with Python, SQL/NoSQL, and optional React/Next.js, plus