Skip to Main Content

Job Title


Manager, Software Engineering, CoCounsel AI Drafting


Company : PowerToFly


Location : Toronto, Ontario


Created : 2026-01-31


Job Type : Full Time


Job Description

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? Were looking for a handson Software Engineering Manager to lead the CoCounsel Drafting team a group of 68 senior and lead engineers building our AIpowered legal drafting engine and skills. This is a 0to1 role at its core: youll shape the future of how attorneys draft, review, and refine legal documents using cuttingedge AI. While we operate within a large organization, weve built a team culture that thinks and moves like a startup. Youll have the autonomy to focus on what matters: delivering innovative products with speed and ownership. If youre 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 6070% 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 highervalue work for their clients. Were deeply committed to our customers success, and were 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 highperforming team of 68 senior and lead software engineers, providing handson coaching, mentorship, and career development guidance. Drive technical strategy and execution for AIpowered 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 0to1 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 highquality software. Recruit and retain top talent by building a strong team culture, conducting interviews, and making strategic hiring decisions. About You Proven 0to1 experience youve 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. Handson 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. Customerobsessed 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 microfrontend (MFE) architectures. Background in legal technology, document automation, or enterprise SaaS products. Familiarity with RAG architectures, prompt engineering, or finetuning language models. Experience building and scaling remotefirst engineering teams. Whats in it For You? Hybrid Work Model: Weve adopted a flexible hybrid working environment (23 days a week in the office depending on the role) for our officebased roles while delivering a seamless experience that is digitally and physically connected. Flexibility & WorkLife 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 community, or finding time to refresh and reset. This builds upon our flexible work arrangements, including work from anywhere for up to 8 weeks per year, empowering employees to achieve a better worklife balance. Career Development and Growth: By fostering a culture of continuous learning and skill development, we prepare our talent to tackle tomorrows challenges and deliver realworld solutions. Our Grow My Way programming and skillsfirst approach ensures you have the tools and knowledge to grow, lead, and thrive in an AIenabled future. Industry Competitive Benefits: We offer comprehensive benefit plans to include flexible vacation, two companywide Mental Health Days off, access to the Headspace app, retirement savings, tuition reimbursement, employee incentive programs, and resources for mental, physical, and financial wellbeing. Culture: Globally recognized, awardwinning reputation for inclusion and belonging, flexibility, worklife balance, and more. We live by our values: Obsess over our Customers, Compete to Win, Challenge (Y)our Thinking, Act Fast / Learn Fast, and Stronger Together. Social Impact: Make an impact in your community with our Social Impact Institute. We offer employees two paid volunteer days off annually and opportunities to get involved with probono consulting projects and Environmental, Social, and Governance (ESG) initiatives. Making a RealWorld Impact: We are one of the few companies globally that helps its customers pursue justice, truth, and transparency. Together, with the professionals and institutions we serve, we help uphold the rule of law, turn the wheels of commerce, catch bad actors, report the facts, and provide trusted, unbiased information to people all over the world. Additional Recruitment Information Our use of AI within the recruitment process: Thomson Reuters utilizes Artificial Intelligence to support parts of our global recruitment process. The AI system is a supporting tool, but a human makes the final decision on whether you are considered for the role. Equal Employment Opportunity As a global business, we rely on the unique backgrounds, perspectives, and experiences of all employees to deliver on our business goals. To ensure we can do that, we seek talented, qualified employees in all our operations around the world regardless of race, color, sex/gender, including pregnancy, gender identity and expression, national origin, religion, sexual orientation, disability, age, marital status, citizen status, veteran status, or any other protected classification under applicable law. Thomson Reuters is a proud Equal Employment Opportunity Employer providing a drugfree workplace. We make reasonable accommodations for applicants with disabilities and for sincerely held religious beliefs in accordance with applicable law. #J-18808-Ljbffr