Vice President of Sales Operations, League
$225-275k
Consumer experience platform for healthcare
Be an early applicant
Consumer experience platform for healthcare
501-1000 employees
Be an early applicant
$225-275k
501-1000 employees
Company mission
To power next-generation healthcare experiences with a platform built to enable CX transformation.
Role
Who you are
- Bachelor’s degree in Business Administration, Finance, Analytics, or a related field; advanced degree preferred
- 10+ years of progressive experience in Sales Operations, Revenue Operations, or GTM Operations, including senior leadership roles
- Proven experience supporting complex B2B sales organizations, ideally within healthcare technology, health plans, or enterprise SaaS
- Experience with building SalesOps function at startups or publicly-traded companies
- Deep expertise in forecasting, territory and quota design, pipeline management, and sales analytics
- Strong systems experience, including Salesforce and related sales productivity and BI tools
- Demonstrated ability to lead and scale high-performing operations teams
- Exceptional analytical, problem-solving, and executive communication skills
- Strong business acumen with the ability to influence senior stakeholders and drive change
- Experience partnering closely with Sales leadership while maintaining operational objectivity and rigor
- 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 a strategic, data-driven, and highly collaborative VP, Sales Operations to enable and accelerate revenue growth through world-class go-to-market planning, operational rigor, and performance management
- Reporting directly to the Chief Revenue Officer, this leader will own the design, execution, and continuous optimization of League’s sales operating model
- The VP, Sales Operations will partner closely with Go-to-Market, Product, Product Marketing, Engineering, Marketing, and Finance teams, to ensure predictable growth, scalable processes, and exceptional execution across the full revenue lifecycle
- As a core member of League’s Growth Leadership Team—alongside the Chief Revenue Officer, Chief Business Officer, VP Sales, VP Account Management, VP Solution Engineering, and SVP International—this role will have significant influence on League’s growth strategy and operational excellence as the company scales
- This is a high-impact opportunity to shape how League grows and delivers value to customers while improving the health and well-being of millions
- You'll own and evolve League’s end-to-end sales operating model, including territory design, capacity planning, quota setting, and coverage strategy
- Partner with GTM leadership to translate growth strategy into executable plans and operational priorities
- Establish best-in-class forecasting processes, pipeline hygiene standards, and inspection cadences to ensure accuracy and predictability
- Deliver clear, actionable insights on performance trends, risks, and opportunities to executive leadership
- Design, document, and continuously optimize sales processes across the customer lifecycle (new business, expansion, renewals, upsells and cross-sells)
- Partner with Sales Enablement to ensure teams have the right tools, playbooks, and insights to execute effectively
- Define and align with strategic company KPIs and CRO’s objectives, dashboards, and reporting across bookings, pipeline, win rates, cycle times, and productivity
- Use data to identify inefficiencies, inform decisions, and drive continuous improvement
- Own CRM strategy (e.g., Salesforce) and sales productivity tools, ensuring strong adoption, data integrity, and scalability
- Partner with IT to evaluate, implement, and optimize systems that support growth
- Act as a connective leader across Sales, Account Management, Finance, Marketing, Product, and Operations to align incentives, processes, and outcomes
- Support pricing, packaging, and deal governance in partnership with Finance and Legal
- Build, lead, and mentor a high-performing Sales Operations team, fostering a culture of accountability, rigor, and continuous learning
- Ensure access management is performed in compliance with the employee's role and responsibilities
- Responsibility and accountability for executing League's policies and procedures within the department/ team
- Notification of HR, Legal, Compliance & Security of any incidents, breaches or policy violations
- Compliance with Information Security Policies
Application process
- 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.
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