Technical Writer

League; Toronto; On-site; CAD 81,000 - 92,000; Full time

Job summary

A leading healthcare technology platform in Toronto is looking for a Technical Writer to join their team. This role involves the creation of clear and comprehensive documentation, improving product understanding for customers and internal teams. The ideal candidate has over five years of experience in technical writing, strong skills in collaboration, and the ability to create effective documentation using tools like Confluence and AI. A comprehensive benefits package is also offered, including health benefits and professional growth opportunities.

Benefits

Comprehensive Health Benefits

Bonus Program

Employee Stock Option Program

Unlimited Paid Time Off

Wellness Days

Growth Opportunities

Mentorship Program

Qualifications

• Ability to create and maintain release notes and API documentation.
• Experience developing implementation guides and technical documentation.
• Strong skills in creating visual content such as diagrams and infographics.

Responsibilities

• Collaborate with engineering and product teams to enhance documentation.
• Produce high-quality technical content that is easily searchable.
• Drive a reduction in support tickets via improved documentation.

Skills

Technical writing

Ability to explain complex concepts

Relationship building

Knowledge of JIRA

Experience with cloud platforms

Education

5+ years as a Technical Writer

Familiarity with content authoring tools

Experience in Integrated Development Environment

Tools

Confluence

AI tools

Job description

Founded in 2014, League is the leading healthcare consumer experience (CX) platform, powered by artificial intelligence (AI), reaching more than 63 million people around the world and delivering the highest level of personalization in the industry. Payers, providers, and consumer health partners build on League’s platform to deliver high‑engagement healthcare solutions proven to improve health outcomes. League has raised over $285 million in venture capital funding to date, powering the digital experiences for some of healthcare’s most trusted brands, including Highmark Health, Manulife, Medibank, and Shoppers Drug Mart.

Position Summary

We’re seeking a skilled Technical Writer to join our documentation team and help create clear, comprehensive documentation that helps our customers and internal teams understand and use our platform products and services. This role involves working closely with engineering teams, product managers, and other stakeholders to produce high‑quality, easy‑to‑understand technical content.

In this role, you will:

Documentation Creation and Management:

• Write and maintain release notes for product updates and SDK versions
• Create and update API documentation in collaboration with engineering teams
• Produce implementation guides and technical documentation for developers

Content Strategy and Process:

• Create announcements and communications for product releases
• QA content for accuracy and completeness before publication
• Provide inputs to the content architecture to align with our customers’ information needs
• Collaborate with cross‑functional teams including releases, engineering, and product teams
• Develop best practices, processes, and templates to help our product and engineering teams develop high‑quality technical documentation

Tools and Technology:

• Use AI tools such as Cursor, ChatGPT, and Gemini to help draft content, understand code, and create process efficiencies
• Work with modern documentation platforms and version control systems
• Create visual content including screenshots and multimedia assets

Collaboration and Communication:

• Partner closely with engineering teams and managers to improve documentation quality
• Work with the releases team to coordinate documentation with product launches
• Participate in cross‑team meetings and product demonstrations
• Provide and incorporate feedback on documentation processes and content

Desired Outcomes:

• Create comprehensive, easily searchable content (including tutorials, code examples, and API references) that serves as the primary source of truth for the League platform
• Accelerate ‘Time to First Integration’ for 3rd‑party developers and System Integrators by creating friction‑free onboarding guides and self‑service references
• Drive a measurable reduction in support tickets and engineering inquiries by proactively addressing common implementation friction points in the documentation
• Embed deeply with Product and Engineering teams to capture feature details upstream, ensuring documentation is released in lock‑step with code deployments
• Maintain a workflow that ensures documentation is version‑controlled, automated, and scales alongside our platform’s rapid release cycle

About You:

• You have strong technical writing skills with the ability to clearly explain complex concepts
• You’ve been working as a Technical Writer for cloud and/or platform products for at least five (5) years
• You’re familiar with content authoring tools such as Confluence
• You’re comfortable working within Integrated Development Environment (IDE)
• You have hands‑on experience creating architecture diagrams, infographics, and screenshot markups
• You have experience with JIRA and project management tools
• You have a demonstrated ability to build effective relationships with Engineers and Product Managers

What We Offer

• Comprehensive Health Benefits: We prioritize your well‑being with complete medical, dental, and vision coverage
• Bonus Program: Be rewarded for your contributions with our performance‑based bonus program
• Employee Stock Option Program: Become an owner and share in our success through our stock option program
• Unlimited Paid Time Off: Take the time you need to recharge and maintain a healthy work‑life balance
• Spending Accounts: Manage your healthcare and dependent care expenses with tax‑advantaged spending accounts
• Wellness Days: Prioritize your mental and physical health with dedicated wellness days throughout the year
• Growth Opportunities: We invest in your future with abundant opportunities for professional development and advancement
• Mentorship Program: Benefit from guidance and support from experienced leaders in your field

Application Process

• Submit Your Application: You’ll receive a confirmation email right away.
• Intro Sessions: Learn more about our culture, get alignment on your compensation expectation prior to committing to next steps.
• Take‑home assessment
• Meet the Engineering Team: Dive into technical discussions and learn how you can make an impact at League.
• Final Steps: Meet our cross‑functional team and the hiring managers and share experiences on collaboration.
• Offer and onboarding

Security‑related Responsibilities

• Compliance with Information Security Policies
• Compliance with League’s secure coding practice
• Responsibility and accountability for executing League's policies and procedures
• Notification of HR, Legal, Compliance & Security of any incidents, breaches or policy violations

Salary Range (Canada Applicants Only)

$81,000 - $91,900 CAD

Equal Employment Opportunity Statement

We are committed to equal employment opportunity regardless of race, color, ancestry, religion, sex, national origin, sexual orientation, age, citizenship, marital status, disability, gender identity or Veteran status. If you are an individual in need of assistance at any time during our recruitment process, please contact us at [e-mail].

Use of AI Notice

We are committed to ensuring fairness and transparency throughout our hiring process. League may use Artificial Intelligence (AI) tools to assist in the screening of applicants for this position. Please check out our stance on using AI in recruitment here.

Privacy Policy

Review our Privacy Policy for information on how League is protecting personal data.