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.

The Role

League is seeking an experienced and strategic AVP, Total Rewards & People Operations, to lead the design, governance, and delivery of our global Total Rewards programs and People Operations service model.

This role sits at the intersection of strategy, governance, and execution, with required exposure to Board-level compensation discussions and decision-making. You will shape how League attracts, rewards, and retains talent while ensuring scalable, compliant, and employee-centric people operations.

This role leads a team responsible for enterprise-wide Total Rewards strategy and People Operations service delivery, with a balance of hands-on execution, executive partnership, and delegation through experienced managers and specialists.

As a senior leader within People & Culture, you will partner closely with executive leadership, Finance, Legal, and the Board to evolve compensation, equity, and people operations strategies in line with League’s growth and maturity.

What You’ll Do

Total Rewards & Compensation Strategy

Develop and lead League’s global Total Rewards strategy, including compensation philosophy, pay equity, incentives, benefits, and recognition programs.
Monitor market trends, emerging practices, and regulatory developments to ensure League remains competitive and differentiated as an employer of choice across geographies.
Determine optimal compensation survey data sources and cadence; lead market analysis to ensure alignment with League’s compensation philosophy and business strategy.
Oversee the flawless execution of annual compensation cycles, from budget recommendations and approvals through processing and communications.
Own global health, wellness, and retirement programs, including annual renewals and vendor partnerships.
Design and oversee recognition and reward programs that reinforce League’s values, performance culture, and employee experience.
Lead executive and Board-level compensation strategy and outcomes discussions.
Prepare and present materials for the Board and Compensation Committee.
Serve as a trusted advisor to senior leadership and the Board on compensation governance, risk, competitiveness, and long-term incentive design.
Own and evolve League’s equity compensation strategy, including stock option programs and the future transition to RSUs.
Ensure compliance with all relevant pay equity, pay transparency, and Total Rewards-related legislation.
Leverage advanced analytics and AI-enabled tools to support modeling, pay equity analysis, and executive and Board-level decision-making.

People Operations & Service Delivery

Lead a People Operations function that delivers highly responsive, customer-centric, and efficient services across the employee lifecycle.
Oversee employee inquiries, leave of absence management, and immigration processes.
Establish clear service standards, operating rhythms, and accountability for operational excellence.
Drive adoption of automation and AI-supported workflows while maintaining a high-touch employee experience.
Partner with Finance and People & Culture leadership on annual people-related budgeting and forecasting.
Ensure People & Culture policies are consistent, compliant, and reviewed on an appropriate cadence.

HR Technology, People Analytics & Job Architecture

Lead the advancement of HR technology strategy, maximizing the value of League’s HRIS and related tools.
Identify and implement opportunities to leverage automation and AI-enabled solutions to increase efficiency and insight.
Develop and execute a people analytics roadmap, including executive dashboards and KPIs.
Own and evolve League’s job architecture and leveling frameworks.

Leadership & Strategic Partnership

Provide strategic and hands-on leadership to a multidisciplinary Total Rewards and People Operations team.
Maintain direct involvement in the design and execution of critical initiatives with executive or Board visibility.
Act as the primary People & Culture leader supporting Board and Compensation Committee engagement.
Partner closely with Finance, Legal, and business leaders to align people programs with organizational priorities.

About You

10+ years of progressive HR experience with deep expertise in Total Rewards.
5+ years of people leadership experience.
Experience leading Board- or Compensation Committee-level compensation discussions ( Required )
Strong knowledge of equity compensation, including stock options and RSUs.
Experience adopting AI-enabled HR or analytics tools.
Strong analytical, systems, and change leadership skills.
Ability to influence executives and Board members.
Comfortable operating in a fast-paced, evolving environment.

Why You’ll Love Working at League
At League, you’ll shape how we reward and support our people at a critical stage of growth. We offer competitive compensation and equity, comprehensive benefits, flexible work arrangements, and a culture that values impact, curiosity, and collaboration.

Equal Opportunity
League is proud to be an equal opportunity employer. We are committed to an inclusive and accessible experience for all candidates and employees.

Security - Related Responsibilities

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

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

$171,700—$209,900 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.

Privacy Policy

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AVP, Total Rewards & People Operations

TLDR