Technical Writer

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 recruitinginfo@league.com.

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.

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