Company: League

Location: Toronto, ON

Expected salary: $149300 – 182500 per year

Job date: Wed, 27 Aug 2025 22:43:38 GMT

Job description: About LeagueFounded 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 SummaryThis is a pivotal leadership role designed for a strategic, execution-obsessed Product Marketer ready to build a world-class growth enablement function. You will be the architect of a program that dramatically increases the productivity and effectiveness of our revenue teams. You’ll be the driving force behind a collaborative, data-driven approach to enablement, with a mission to ensure our Go-to-Market (GTM) teams are equipped, trained, and empowered to deliver exceptional value to our prospects & customers.You will report directly to the AVP of Product Marketing and work closely with GTM leadership. Your ultimate goal is to build and scale a world-class enablement function that empowers our teams with the knowledge, tools, and content they need to effectively sell and expand our solutions.In this role, you will:

• Architect the Enablement Strategy & Roadmap: In close partnership with GTM leadership, define the vision, strategy, and priorities for the Growth Enablement function. Build and own the comprehensive enablement strategy and calendar to align with revenue goals.
• Curate a World-Class Content Library: Partner with Upstream/Downstream PMMs who own creation of assets to curate a dynamic library of high impact sales resources. The library will include pitch decks, battlecards, demo scripts, case studies, and ROI tools, ensuring they are always fresh, accessible, and effective.
• Deliver High-Impact Training & Programs: Lead the design and delivery of engaging training programs, from new hire onboarding to continuous learning. Own the agenda and execution for major GTM events like the quarterly Growth Summits and the annual Sales Kick-Off (SKO).
• Pioneer AI-Powered Enablement: Lead the charge in leveraging AI to create and deliver cutting-edge enablement programs. This includes exploring and implementing solutions for personalized, just-in-time learning, role-playing simulations, and intelligent content recommendations.
• Measure and Optimize for Impact: Define and track the KPIs that matter. Go beyond content usage to measure direct impact on business outcomes like win rates, sales cycle length, and deal size.
• Leverage Healthcare Product Marketing Expertise: Bring your expertise in healthcare to the product marketing lifecycle and collaborate with your direct team and cross-functional teams to accelerate League’s growth.

Team CollaborationYou will be a core member of our Product Marketing leadership team, working alongside the Director of Product Marketing for Upstream and the Director of Product Marketing for Downstream. While they own the GTM strategies for their respective areas and are responsible for core content, you will establish the enablement strategy and execution plan for the entire team, ensuring our go-to-market efforts are seamlessly supported with best-in-class enablement.About You:

• 8+ years of product marketing experience, with a proven track record of success in sales and partner enablement in enterprise sales or prior experience in sales in an enterprise setting.
• Demonstrated experience in building and executing an enablement strategy from the ground up in a fast-paced B2B SaaS environment.
• Must have experience in the healthcare technology or digital health industry. Credibility with sales teams who sell into payers, providers, or large employers is essential.
• A passion for and experience with leveraging technology, particularly AI, to scale and modernize enablement programs.
• Exceptional ability to translate complex product capabilities into simple, compelling, and value-driven training.
• A bias for action and a strong sense of ownership.
• Strong analytical skills with a data-driven approach to measuring impact and ROI.
• Excellent communication, presentation, and collaboration skills, with the ability to influence stakeholders at all levels.

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$149,300—$182,500 CADOur 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 .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:Recognize and Avoid Employment scams. Practice safe job searching. Scammers are getting craftier and leveraging fake job postings to get personal information. Know the warning signs and protect yourself from scammers. Learn more .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 .Privacy PolicyReview our for information on how League is protecting personal data.

League Overview

Founded in 2014, League is a leading healthcare consumer experience platform utilizing AI to serve over 63 million people globally, focusing on personalized healthcare solutions. The platform supports payers, providers, and consumer health partners to enhance health engagement, backed by over $285 million in funding, benefiting notable organizations like Highmark Health and Shoppers Drug Mart.

Position Summary

League is seeking a strategic Product Marketer to bolster its growth enablement function. This leadership role involves developing a comprehensive strategy to enhance productivity among revenue teams and ensuring the Go-to-Market (GTM) teams are equipped with necessary tools and training. Key responsibilities include:

• Enablement Strategy & Roadmap: Shape the vision and priorities for growth enablement in alignment with revenue goals.
• Content Library Development: Collaborate with PMMs to create impactful sales resources.
• Training Program Delivery: Design and implement training for onboarding and continuous learning.
• AI Integration: Leverage AI for innovative enablement programs and personalized learning.
• Impact Measurement: Assess key performance indicators affecting business outcomes.
• Collaboration: Work with the Product Marketing leadership team to align enablement strategies.

Qualifications

Candidates should possess 8+ years in product marketing, with experience in sales enablement within enterprise settings, preferably in healthcare technology. The ideal candidate will demonstrate a strong understanding of sales processes, technological proficiency, and analytics capabilities.

Compensation

The salary range for this role in Canada is CAD $149,300—$182,500, exclusive of bonuses and benefits.

Diversity Commitment

League values diverse backgrounds and seeks the best candidates, emphasizing equal employment opportunities.

Application Process

Interested candidates can expect a confirmation email post-application, followed by a review from a recruiter. If there’s alignment, the recruiter will reach out to discuss the next steps.

For further information about League, potential candidates are encouraged to explore company resources on hiring, privacy policies, and the use of AI in recruitment.