Lead Software Engineer, CoCounsel AI Drafting

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** Lead Software Engineer, CoCounsel AI Drafting page is loaded## Lead Software Engineer, CoCounsel AI Drafting remote type:
Hybrid locations:
Canada, Toronto, Ontario time type:
Full time posted on:
Posted Todayjob requisition :
JREQ
195767

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

Lead Software Engineer, AIWe're looking for a Lead 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 architect LLM-powered drafting flows - orchestrating 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
** In this opportunity as a Lead Software Engineer, AI, you will:
• Design and build AI-powered features for legal document drafting, working across the full stack from backend services to frontend experiences  
• Architect LLM-integrated systems - designing prompt orchestration, AI pipelines, and the integration layers that connect AI capabilities to user-facing products  
• Design for reliability and observability in AI systems, ensuring low-latency responses and high-quality outputs within the drafting engine  
• Drive technical decisions by evaluating trade-offs, proposing architectures, and leading implementation of complex systems  
• Thrive in ambiguity by proactively identifying problems, proposing solutions, and driving decisions without waiting for direction  
• Collaborate cross-functionally with Product, Design, and Research to define requirements and deliver impactful features that solve real customer problems  
• Mentor and elevate the team by sharing knowledge, reviewing code, and raising the bar for engineering excellence  
• Embrace 0-to-1 thinking by building new capabilities from scratch - operating like a startup within a larger organization  
• Own quality and delivery by writing well-tested, maintainable code and ensuring the team ships reliably
** About You
** You're a fit for the role of Lead Software Engineer, AI if you have the following required qualifications:
• 7+ years of software engineering experience with a track record of delivering complex, high-impact systems  
• Experience building and deploying applications powered by LLMs - you understand the unique challenges of AI-integrated systems  
• Proven 0-to-1 experience - you've built products from scratch, thrive in ambiguity, and know how to make decisions with incomplete information  
• 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  
• Experience leading technical initiatives and influencing engineering direction without formal authority  
• 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 include:
• Experience with microfront end (MFE) architectures  
• Background in prompt engineering, vector databases, or fine-tuning language models  
• Experience in legal technology, document automation, or enterprise SaaS products#LI-ES1
* ** 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…