VP, Sales Operations

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 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.

What you'll do:

Go-To-Market Strategy & Planning

• 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.

Forecasting, Pipeline & Performance Management

• 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.

Sales Process & Enablement Optimization

• 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.

Data, Analytics & Insights

• 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.

Systems & Tools Ownership

• 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.

Cross-Functional Leadership

• 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.

Team Leadership

• Build, lead, and mentor a high-performing Sales Operations team, fostering a culture of accountability, rigor, and continuous learning.

Security-Related Responsibilities

• 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

What you'll bring: 

• 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 health