Senior Software Engineer, CoCounsel AI Drafting

PowerToFly; Toronto; Hybrid; CAD 105,000 - 155,000; Full time

Job summary

A leading technology company based in Toronto is seeking a Senior Software Engineer to develop AI-powered legal drafting tools. In this role, you will design and implement features that revolutionize how attorneys create documents, working on both frontend and backend systems. The ideal candidate will have extensive software engineering experience, particularly with AI applications, and be proficient in C#, Python, and cloud technology such as AWS. The role offers a competitive salary range of CAD 105,000 - CAD 155,000, along with flexible work arrangements and comprehensive benefits.

Benefits

Flexible hybrid work model

Flexible vacation

Mental Health Days off

Tuition reimbursement

Employee incentive programs

Qualifications

• 4+ years of software engineering experience with a track record of delivering complex systems.
• Experience building applications powered by LLMs.
• Full-stack capability comfortable owning features end-to-end.

Responsibilities

• Design and build AI-powered features for legal document drafting.
• Build LLM-integrated systems with prompt orchestration.
• Collaborate with Product, Design, and Research teams.

Skills

Software engineering experience

Building applications powered by LLMs

Full-stack development

C#

Python

Angular/React

AWS

Excellent communication skills

Tools

Micro-frontend architectures

Prompt engineering

Vector databases

Enterprise SaaS products

Job description

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

Senior Software Engineer, AI

Are you ready to shape the future of legal technology with AI? Do you thrive in ambiguous, fast‑moving environments where you can build products from the ground up?

We’re looking for a Senior Software Engineer to join the CoCounsel Drafting team. In this role, you’ll be hands‑on designing and building the systems that transform how attorneys draft, review, and refine legal documents. You’ll work across the full stack—building AI pipelines, prompt layers, and frontend experiences into a seamless product. You’ll have the autonomy to focus on what matters: solving hard technical problems and shipping impactful products. If you’re energized by ambiguity, take initiative without being asked, and love building new products—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 an engineer who shares that passion for making a real difference in how legal work gets done.

About the Role

• Design and build AI‑powered features for legal document drafting, owning features end‑to‑end across backend services and frontend experiences
• Build LLM‑integrated systems—implementing prompt orchestration, AI pipelines, and the integration layers that connect AI capabilities to user‑facing products
• Contribute to reliability and observability in AI systems, ensuring low‑latency responses and high‑quality outputs within the drafting engine
• Collaborate on technical decisions by evaluating trade‑offs, proposing solutions, and implementing complex systems
• Thrive in ambiguity by proactively identifying problems, proposing solutions, and driving work forward without waiting for direction
• Collaborate cross‑functionally with Product, Design, and Research to deliver impactful features that solve real customer problems
• Own quality and delivery by writing well‑tested, maintainable code and shipping reliably

About You

• 4+ years of software engineering experience with a track record of delivering complex, high‑impact systems
• Experience building applications powered by LLMs—you understand the unique challenges of AI‑integrated systems
• Full‑stack capability—comfortable owning features end‑to‑end across backend services and frontend applications
• 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 collaborate across engineering, product, and design

Additional Preferred Qualifications

• Experience with micro‑frontend (MFE) architectures
• Background in prompt engineering, vector databases, or fine‑tuning language models
• Experience in legal technology, document automation, or enterprise SaaS products

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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 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 work‑life balance.
• Career Development and Growth: By fostering a culture of continuous learning and skill development, we prepare our talent to tackle tomorrow’s challenges and deliver real‑world solutions. Our Grow My Way programming and skills‑first approach ensure you have the tools and knowledge to grow, lead, and thrive in an AI‑enabled future.
• Industry Competitive Benefits: We offer comprehensive benefit plans to include flexible vacation, two company‑wide 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, award‑winning reputation for inclusion and belonging, flexibility, work‑life 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 pro‑bono consulting projects and Environmental, Social, and Governance (ESG) initiatives.
• Making a Real‑World 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.

Our use of AI within the recruitment process Thomson Reuters utilizes Artificial Intelligence (AI) to support parts of our global recruitment process. Unless you opt‑out, our AI system will assess the information provided by you and compare it to the requirements listed for the role, and present the result to our recruitment personnel for further review. The AI system acts as a supporting tool, but there is always a human making the decision if you will be considered for the role.

Thomson Reuters complies with local laws that require upfront disclosure of the expected pay range for a position. The base compensation range varies across locations. For Ontario, Canada, the base compensation range for this role is $105,000 CAD – $155,000 CAD. Base pay is positioned within the range based on several factors including an individual’s knowledge, skills and experience with consideration given to internal equity. Base pay is one part of a comprehensive Total Reward program which also includes flexible and supportive benefits and other wellbeing programs. This role may also be eligible for an Annual Bonus based on a combination of enterprise and individual performance.

About Us

Thomson Reuters informs the way forward by bringing together the trusted content and technology that people and organizations need to make the right decisions. We serve professionals across legal, tax, accounting, compliance, government, and media. Our products combine highly specialized software and insights to empower professionals with the data, intelligence, and solutions needed to make informed decisions, and to help institutions in their pursuit of justice, truth, and transparency. Reuters, part of Thomson Reuters, is a world leading provider of trusted journalism and news.

We are powered by the talents of 26,000 employees across more than 70 countries, where everyone has a chance to contribute and grow professionally in flexible work environments. At a time when objectivity, accuracy, fairness, and transparency are under attack, we consider it our duty to pursue them. Sound exciting? Join us and help shape the industries that move society forward.

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 proud to be an Equal Employment Opportunity Employer providing a drug‑free workplace.

We also make reasonable accommodations for qualified individuals with disabilities and for sincerely held religious beliefs in accordance with applicable law. More information on requesting an accommodation here.

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More information about Thomson Reuters can be found on thomsonreuters.com