League is one of the fastest-growing technology companies in Canada and the leading healthcare experience platform. That gap costs health plans and health systems money, and it costs people their health. Health plans and health systems trust us to do this at scale.

You're the most senior growth marketing hire on a team that's re-building its demand generation engine. You'll be marketing into two of the most sought-after B2B buyer groups in health tech: payers with long procurement cycles and multiple clinical/financial stakeholders, and providers balancing patient experience against margin pressure. If you want to prove you can build and run demand gen at enterprise scale, in a category where the sales cycle actually tests your craft, this is that proving ground.

You're inheriting a full, well-funded MarTech stack - Salesforce, Pardot, Bizible, Demandbase, and Qualified - and the website itself, but the job isn't to just run any of it as-is. We want someone who rebuilds how that stack operates to be agentic-first: designing AI agents that pull signal to plan campaigns, launch and sequence them across channels, and continuously test and optimize without manual hand-offs between tools.

Own and optimize our tech stack and website

Own pipeline generation across paid search, paid social (LinkedIn), SEO, content, lifecycle/email, and account-based marketing

Continuously test messaging, creative, and campaign structure - and bring examples of non-boilerplate campaigns that actually moved pipeline

Own reporting: define KPIs and dashboards, and keep pipeline numbers trusted by Sales

Strategically partner cross-functionally with Sales, Product Marketing and Revenue Operations

Compliance with Information Security Policies

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

7+ years in B2B demand generation or growth marketing, with real ownership of pipeline outcomes - not just campaign support

Enterprise background: you've marketed to large, complex organizations with long sales cycles and multiple stakeholders; Hands-on across the full stack: paid search, paid social (LinkedIn), SEO, content, and account-based marketing

Fluent in the pipeline metrics that matter here - MQL/SQL/SQO conversion, pipeline contribution, cost per opportunity - not just CAC/LTV/ROAS

Real experience building AI agents or automations, not just prompting a chatbot - bonus if you already gravitate toward MCP-first, Salesforce-native tools

Bonus: experience with ABM platforms like Demandbase or 6sense

Bonus: experience in HealthTech, FinTech, InsurTech, or other large enterprise-focused products

CANADA APPLICANTS ONLY: The Canada-specific compensation range below for this full-time position is exclusive of bonus, equity and benefits. 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. 145,000-$170,000 CAD

We expect all employees regardless of role or level to thoughtfully leverage AI to improve the quality, speed, and impact of their work.

drafting, analysis, coding, research, or process automation)





Apply judgment and accountability when using AI by reviewing outputs for accuracy, bias, and quality before use

Identify opportunities to improve how work gets done from personal productivity to team-level workflows by leveraging AI effectively

Operate with strong data responsibility and security awareness, especially when working with sensitive or regulated information

Individual Contributors: Use AI to improve personal productivity and quality of output

Senior ICs / Managers: Ability to balance efficiency with quality and sound judgment

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. We have a mix of office-centric roles based in our vibrant Toronto office, and remote-eligible roles based anywhere in Canada or US. 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. League may use Artificial Intelligence (AI) tools to assist in the screening of applicants for this position.

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📌 Market Chief Marketing Officer - Full Time (Winnipeg)
🏢 Neura Market
📍 Winnipeg