Senior / Staff Software Engineer, AI Tech Strike Team

Waabi • Toronto, ON

6d • $165,000 - $265,000 • Hybrid

About The Position

Waabi is building a dedicated AI Technical Strike Team to establish centralized best practices for working with AI across Waabi with the aim of maximizing productivity. This team is looking for hands-on senior software engineers to build the AI tooling, agents, and workflows that accelerate how Waabi works. As a Software Engineer on the AI Tech Strike Team, you will design, build, and ship the tools that compound the productivity of every team at Waabi. The team will own a mix of core tooling work and deployed engagements, where members of the team work closely with functions across Waabi to understand their pain points and co-design AI workflows to maximize productivity.

Requirements

• 5+ years of software engineering experience, with a track record of shipping tools, platforms, or products used by large internal or external user bases.
• Deep, hands-on familiarity with the current generation of AI coding tools and agents (Claude Code, Cursor, Copilot, Codex, or similar), and demonstrated experience building and shipping AI-powered products, agents, or workflows — including prompt engineering, evals, tool use, and integrating LLMs into production systems.
• Strong proficiency in Python (or another common programming language), and comfort working across modern build systems, CI/CD pipelines, and developer infrastructure.
• Strong product instincts and judgment: you can identify high-leverage problems across a diverse set of teams, scope pragmatic solutions, and ship things that actually get adopted.
• Strong written and verbal communication skills, comfortable operating with a high degree of autonomy in ambiguous, fast-moving territory and influencing engineers, researchers, and business partners.
• Passionate about self-driving technologies, frontier AI, and using AI to push the boundary of what a small, world-class team can accomplish.

Nice To Haves

• Prior experience in a developer productivity, platform engineering, or AI tooling role, ideally with exposure to ML, robotics, or autonomous systems infrastructure (e.g., training pipelines, simulation tooling, large monorepos).
• Experience working effectively with non-engineering stakeholders — translating business workflows into technical solutions for functions like Finance, Commercial, Marketing, HR, Legal, and Operations.
• Experience building AI workflows or automation for business functions outside of engineering (e.g., finance automation, marketing operations, HR workflows).
• Experience deploying and operating AI systems in security- and IP-sensitive environments.
• Contributions to open-source AI tooling, agent frameworks, or developer tools.

Responsibilities

• Design, build, and ship custom internal tooling, agents, and workflows tailored to Waabi — supporting our autonomy codebase, simulation environments, ML training pipelines, and research workflows, as well as agents and automations for business teams.
• Integrate and extend third-party AI tools — from coding assistants and agents (e.g., Claude Code, Cursor, GitHub Copilot) to AI tools for non-engineering functions — building the integrations, configurations, and internal extensions that make them work well for Waabi.
• Evaluate new AI tools, models, and agent frameworks as they emerge, run structured pilots, and provide clear technical recommendations that inform build-vs-buy decisions.
• Partner directly with engineers, researchers, and business teams to understand their workflows, prototype solutions quickly, and iterate based on real usage.
• Build observability around AI tooling at Waabi — tracking usage, adoption, cost, and quality — so we can prioritize with data and understand impact.
• Implement the guardrails for responsible AI tooling at Waabi in partnership with Security, Legal, IT, and Infrastructure.
• Drive adoption of the tools you build through documentation, enablement, office hours, and hands-on support — helping every team get more out of their tools every week.

Benefits

• Competitive compensation and equity awards.
• Health and Wellness benefits encompassing Medical, Dental and Vision coverage (for full-time employees only).
• Unlimited Vacation.
• Flexible hours and Work from Home support.
• Daily drinks, snacks and catered meals (when in office).
• Regularly scheduled team building activities and social events both on-site, off-site & virtually.

What This Job Offers

• Job Type: Full-time
• Career Level: Senior
• Education Level: No Education Listed