ABOUT THE ROLE

LEAP Legal Software is hiring a Personal Injury Content Lead. The ideal candidate is a practicing personal injury lawyer with deep tort and Accident Benefits (AB) experience who will help shape how LEAP’s software empowers personal injury lawyers and practitioners across Canada. This role combines practical litigation knowledge with a passion for innovation in legal technology, ensuring our products are intuitive, efficient, and built for the realities of a PI practice. Whether you act for injured claimants or for insurers, your experience is welcome here, and familiarity with both sides of the file is an asset.

This role will use your experience running files from intake through Superior Court of Justice trials and Licence Appeal Tribunal (LAT) hearings to develop and refine automated matter types, documents, and workflows that mirror how PI lawyers and support staff actually work — from pleadings, AB applications and affidavits to discovery, records and deadline management, and trial or hearing preparation. As a subject-matter expert, you’ll collaborate with our Content Developers and Form Teams to design content that saves time and modernizes how PI law firms deliver legal services. Please note that this role includes presenting LEAP’s PI-specific tools and software to the PI and insurance bar, and we’re looking for someone who enjoys networking and being a visible voice in that community.

**This role is hybrid, working in our Toronto office 3 days/week.**

About LEAP

LEAP leads the world in cloud-based legal practice management software. More than 100,000 lawyers and their staff in small and medium-sized law firms use our software. You’ll be one of over 1,000 smart, caring and ambitious LEAPsters across Australia, Canada, the United States, the United Kingdom, the Republic of Ireland, Poland and New Zealand. Things move fast here, and you’ll be in good company.

KEY RESPONSIBILITIES AND ACCOUNTABILITIES

• Lead content innovation: Conduct legal research to identify opportunities to enhance LEAP’s tort and AB content and automation, including Ontario tort practice, LAT procedure, and developments in appellate decisions.
• Client communication and feedback: Engage with PI clients, gather feedback, and work cross-functionally with our Forms, Development, and Product teams to bring your insights to life.
• Enhance matter types: Oversee and continuously improve LEAP’s Personal Injury matter types, covering both tort and AB files, to ensure seamless workflows from intake through trial or hearing.
• Modernize Personal Injury practice: Curate and expand LEAP’s library of automated forms and documents, including LAT and Superior Court materials, ensuring they accurately populate with client data and support records and deadline management.
• Work with AI tools: Develop intelligent AI prompt templates and leverage LEAP’s AI capabilities to generate draft affidavits, demand and AB correspondence, and other documents — revolutionizing how PI lawyers prepare materials.
• Present and network: Present LEAP’s PI-specific tools and software at conferences, CLEs, and events, and build relationships with the PI and insurance bar.
• Drive new projects: Support strategic content initiatives through research, analysis, and project management, helping deliver best-in-class products to our clients.

Requirements

REQUIRED QUALIFICATIONS

• LL.B. or J.D. degree with active membership in good standing with the Law Society of Ontario or another Canadian Law Society.
• Minimum 4+ years’ experience in extensive tort and AB experience.
• Experience appearing at LAT case conferences and hearings.
• Preferably, exposure to appeals of LAT decisions at the appellate court level.
• Has run files from intake through Superior Court of Justice trials and LAT hearings.
• Has instructed clerks and associates on records and deadline management.
• Strong legal research, drafting, and analytical skills.
• A genuine passion for legal technology and innovation — experience using practice management or document automation software is an asset.
• Excellent communication and collaboration skills — you enjoy working across teams and departments and networking with the PI and insurance bar.
• Comfort presenting LEAP’s PI-specific tools and software to external audiences.
• Strong organizational and project management abilities with a focus on quality and detail.
• A proactive, curious mindset — you love finding smarter, simpler ways to get things done.
• Ability to travel occasionally for conferences and other work-related initiatives.

Benefits

What you'll get

Why work at LEAP?

There are endless opportunities within our business to progress and grow your career and full training is provided so an aptitude and hunger to learn is essential. We offer:

• Competitive compensation with a base salary range of $130,000-$140,000 CAD
• Excellent group insurance benefits
• RRSP with employer matching
• Generous Paid Time Off (PTO), including starting at 4 weeks’ vacation, sick days, floater/personal days and volunteer days
• Hybrid working model at our beautiful and modern downtown Toronto office as well as work from home days
• Collaborative and inclusive work environment filled with learning and support
• The skills of a practising lawyer without the billable hours
• Work-life balance – While there may be times that extended hours are required, this is generally a ‘9-5’ role

At LEAP,

We care about what we do and the people we work with

We continually improve to be the best

We NEVER EVER GIVE UP!

At LEAP we are committed to fostering an inclusive and accessible environment. We are dedicated to building a workforce that reflects the diversity of the community in which we live, including those with disabilities. LEAP is committed to providing accommodations in all parts of the hiring process. If you require accommodation, we will work with you to meet your needs.