×
Register Here to Apply for Jobs or Post Jobs. X

Manager, Software Engineering, CoCounsel AI Drafting

Job in Toronto, Ontario, C6A, Canada
Listing for: PowerToFly
Part Time position
Listed on 2026-01-11
Job specializations:
  • Software Development
    Software Engineer, Cloud Engineer - Software, Full Stack Developer, Software Architect
Salary/Wage Range or Industry Benchmark: 200000 - 250000 CAD Yearly CAD 200000.00 250000.00 YEAR
Job Description & How to Apply Below

Software Engineering Manager, AI

Replacement:
This position is open due to an existing vacancy to support our evolving business needs.

Are you ready to lead a high-impact engineering team at the intersection of AI and legal technology? Do you thrive in ambiguous, fast-moving environments where you can shape products from the ground up?

We’re looking for a hands‑on Software Engineering Manager to lead the CoCounsel Drafting team – a group of 6–8 senior and lead engineers building our AI‑powered legal drafting engine and skills. This is a 0‑to‑1 role at its core: you’ll shape the future of how attorneys draft, review, and refine legal documents using cutting‑edge AI. While we operate within a large organization, we’ve built a team culture that thinks and moves like a startup.

You’ll have the autonomy to focus on what matters: delivering innovative products with speed and ownership. If you’re energized by ambiguity, take initiative without being asked, and love building new products from scratch – this role is for you.

Why this matters:
Attorneys spend 60‑70% of their time drafting documents. The tools we build are fundamentally transforming the practice of law – giving legal professionals back countless hours to focus on higher‑value work for their clients. We’re deeply committed to our customers’ success, and we’re looking for a leader who shares that passion for making a real difference in how legal work gets done.

About

the Role
  • Lead and develop a high‑performing team of 6–8 senior and lead software engineers, providing hands‑on coaching, mentorship, and career development guidance.
  • Drive technical strategy and execution for AI‑powered legal drafting capabilities, staying close to the code and architecture while guiding your team.
  • Thrive in ambiguity by proactively identifying problems, proposing solutions, and driving decisions without waiting for direction.
  • Partner with Product, Design, and Research to define requirements, prioritize work, and deliver impactful features that solve real customer problems.
  • Embrace 0‑to‑1 thinking by establishing engineering practices, making fast decisions, and building new capabilities from scratch – operating like a startup within a larger organization.
  • Own delivery outcomes by removing blockers and ensuring the team consistently ships high‑quality software.
  • Recruit and retain top talent by building a strong team culture, conducting interviews, and making strategic hiring decisions.
About You
  • Proven 0‑to‑1 experience – you’ve built products or teams from scratch, thrive in ambiguity, and know how to make decisions with incomplete information.
  • 5+ years of software engineering experience with at least 2 years in engineering management or technical leadership.
  • Hands‑on technical leader who stays close to the code – you can review PRs, debug production issues, and make architectural decisions.
  • Startup mentality with enterprise awareness – you move fast and cut through noise while understanding when process matters.
  • Strong technical foundation in our stack: C#, Python, Angular/React, and AWS.
  • Demonstrated proactivity – you identify what needs to be done and drive it forward without waiting to be asked.
  • Customer‑obsessed mindset – you care deeply about the impact your products have on real users.
  • Excellent communication skills with the ability to influence stakeholders across product, design, and executive leadership.

Additional preferred qualifications:

  • Experience with micro‑frontend (MFE) architectures.
  • Background in legal technology, document automation, or enterprise SaaS products.
  • Familiarity with RAG architectures, prompt engineering, or fine‑tuning language models.
  • Experience building and scaling remote‑first engineering teams.
What’s in it For You?
  • Hybrid Work Model:
    We’ve adopted a flexible hybrid working environment (2‑3 days a week in the office depending on the role) for our office‑based roles while delivering a seamless experience that is digitally and physically connected.
  • Flexibility & Work‑Life Balance:
    Flex My Way is a set of supportive workplace policies designed to help manage personal and professional responsibilities, whether caring for family, giving back to the…
Note that applications are not being accepted from your jurisdiction for this job currently via this jobsite. Candidate preferences are the decision of the Employer or Recruiting Agent, and are controlled by them alone.
To Search, View & Apply for jobs on this site that accept applications from your location or country, tap here to make a Search:
 
 
 
Search for further Jobs Here:
(Try combinations for better Results! Or enter less keywords for broader Results)
Location
Increase/decrease your Search Radius (miles)

Job Posting Language
Employment Category
Education (minimum level)
Filters
Education Level
Experience Level (years)
Posted in last:
Salary