Assistant Vice President of Total Rewards & People Operations, League
CA$171.7-209.9k
OTE
The Canada-specific compensation range for this full-time position is exclusive of bonus, equity and benefits
More information about location
4 days a week in office
Consumer experience platform for healthcare
Be an early applicant
Consumer experience platform for healthcare
501-1000 employees
Be an early applicant
CA$171.7-209.9k
OTE
The Canada-specific compensation range for this full-time position is exclusive of bonus, equity and benefits
More information about location
4 days a week in office
501-1000 employees
Company mission
To power next-generation healthcare experiences with a platform built to enable CX transformation.
Role
Who you are
- 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
- 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
What the job involves
- 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
- 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
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
Our take
Health benefits are a top requirement for anyone seeking a new job in the US today, but classic one-size-fits-all plans are no longer regarded fit for service. League's platform - for payers, providers, consumer health businesses, and employees - connects all benefits in one HIPAA-compliant place, to enable all bodies involved with health benefits to provide better customer healthcare experiences.
League is already one of the bigger players in the employee wellness space, having capitalised on the recently accepted correlation between employee health and productivity to secure huge clients like Uber, Shopify and Unilever. The company has seen significant investment, which will support the scaling of its platform-as-a-service offering. With more than 63 million contracted users, it is securing its position as the leading digital infrastructure for an integrated health ecosystem.
Freddie
Company Specialist at Welcome to the Jungle
Insights
-4% employee growth in 12 months
Company
Funding (last 2 of 4 rounds)
Feb 2022
$95m
SERIES C
Jul 2018
$47.1m
SERIES B
Total funding: $171.1m
Company benefits
- Flexible medical and dental plans
- 401(k) and RRSP matching programs
- Health, lifestyle, learning and family spending accounts
- Employee stock option program (ESOP)
- Generous leaves (including parental and sabbatical)
- Flexible time off
Company HQ
Entertainment District, Toronto, ON
Leadership
Michael Serbinis
(Founder & CEO)Founder of DocSpace and Kobo. Experience as CEO for Three Angels Capital and Board Director for Vector Insitute, among other prominent business leadership roles.
Salary benchmarks
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