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Posted May 4, 2026

Senior Machine Learning Engineer (Small Language Models)

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About League
 

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

League is seeking a Senior ML Engineer to join our AI Models team, focused on advancing innovation in small language models (SLMs) and applied AI systems.

This role sits at the intersection of research and engineering, with a strong emphasis on experimentation, model development, and applied system design. You will work closely with AI leadership to explore, prototype, and operationalize new approaches to domain-specific language models that power League’s healthcare platform.

Unlike a traditional engineering role, this position is R&D-focused, designed for someone who can:

You will contribute to building League’s next generation of AI capabilities, while partnering with platform and product teams to bring high-impact innovations into production.


In this role, you will:

Model Development & Experimentation

Applied AI & Systems Integration

Data & Training Strategy

Evaluation & Model Quality

AI-Native Development Practices

Cross-Functional Collaboration

About you: 


AI Fluency & Ways of Working


At League, we are an AI-native organization. We expect all employees regardless of role or level to thoughtfully leverage AI to improve the quality, speed, and impact of their work.

What this means in practice:
How this scales by level:
What we look for:


Security-Related Responsibilities

CANADA APPLICANTS ONLY: The Canada-specific compensation range below for this full-time position is exclusive of bonus, equity and benefits. This range reflects the minimum and maximum target for base salaries for the position across all Canadian locations. The salary range is intentional to account for the performance and career progressions a Leaguer will experience in the role throughout their time at League. Where in the band you may land is determined by job-related skills/experience. Your recruiter can share more about the specific salary range specific to your skills and experience during the hiring process.

Compensation range for Canada applicants only
$154,600$189,000 CAD
Our employees come from different backgrounds, and we celebrate those differences. We are looking for the best candidates for our open roles, but do not expect applicants to meet every qualification in order to be considered. If you are excited about what you could accomplish at League and believe you can add value to our team, we would love to hear from you.

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 [email protected].

Our Application Process:
 
Applying to a role you love can be exhausting, and understanding the next steps can feel vague and uncertain. You have done the hard part of submitting your application; let's do ours by sharing potential next steps
  • You should receive a confirmation email after submitting your application.
  • A recruiter (not a computer) reviews all applications at League.
  • If we see alignment with League's needs, a recruiter will reach out to learn more about your goals. The recruiter will also share the team-specific interview process depending on the roles you are exploring.
  • The final step is an offer, which we hope you will accept!
  • Prior to joining us, we conduct reference and background checks. Additional checks could be required for US Candidates, depending on the role you are exploring.
Here are some additional resources to learn more about League:

Work Location:

We have a mix of office-centric roles based in our vibrant Toronto office, and remote-eligible roles based anywhere in Canada or US. Each job posting will indicate where the role will be based. Regardless of the role’s posted location, all Toronto-area Leaguers (living within 65 km of our downtown HQ) collaborate in-office Monday through Thursday. Depending on your distance to the office, you’ll enjoy 10 or 20 Flexible Remote Days each quarter for focus and deep-work time. We are committed to fostering a meaningful work environment and connections for all Leaguers regardless of location.

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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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