About this role.
League is seeking a senior, hands-on growth marketing leader to rebuild its enterprise demand-generation engine for healthcare payers and providers. The role owns pipeline generation, the marketing technology stack, website performance, campaign experimentation, attribution, and trusted reporting. It requires deep B2B enterprise marketing experience across paid search, LinkedIn, SEO, content, lifecycle marketing, and account-based marketing. The director will also lead AI-native workflow and AI Engine Optimization initiatives while partnering closely with Sales, Product Marketing, and Revenue Operations. This is a high-autonomy builder position with substantial strategic and executional responsibility.
Role DNA
A quick view of the complexity, pace, ownership and collaboration implied by the job description.
Job Complexity
5/5Pace & Pressure
5/5Autonomy Level
5/5Communication Load
5/5Salary analysis
Estimated compensation compared with the broader CA market for similar roles.
Core skills
Skills and capabilities most closely associated with this opportunity.
Cover letter sample
Dear Hiring Team,
I am excited to apply for the Director, Growth Marketing role at League. My background in enterprise B2B demand generation includes building integrated pipeline programs across paid media, ABM, lifecycle, content, SEO, and sales-aligned reporting for complex buying committees.
I would bring a builder mindset to redesigning League’s demand-generation engine, combining rigorous experimentation with practical AI automation to improve speed, signal quality, and pipeline outcomes. I am particularly motivated by the opportunity to market a healthcare platform that improves follow-through in care while partnering closely with Sales, Product Marketing, and Revenue Operations.
I would welcome the opportunity to discuss how I can help League create a scalable, AI-native growth function.
Sample interview questions
I would begin with ICP segmentation, buying-committee mapping, baseline funnel conversion analysis, and channel-attribution validation. I would then prioritize a small number of measurable plays by segment, establish shared pipeline definitions with Sales and Revenue Operations, and launch a testing roadmap across paid, ABM, lifecycle, and high-intent website experiences.
I would design a governed workflow in which agents consolidate account, intent, CRM, and campaign data; identify priority audiences and signals; propose campaign actions; and monitor performance. Human review, clear approval gates, data-access controls, and documented quality checks would ensure automation improves execution without creating compliance or brand risk.
I would use a multi-touch view that combines sourced pipeline, influenced pipeline, stage conversion, velocity, cost per opportunity, and account engagement. For enterprise buying cycles, I would also evaluate progression among target accounts and buying groups rather than over-relying on lead volume or last-touch attribution.
I would align on ICP tiers, account ownership, qualification criteria, pipeline-stage definitions, SLAs, and a recurring operating cadence. Joint account reviews and transparent dashboards help surface gaps quickly, while shared campaign plans ensure Marketing programs support the sales team's active priorities.
I would start by analyzing the audience's vendor-research questions, existing brand visibility, content gaps, and technical accessibility. The program would pair authoritative, evidence-based content with structured site improvements, expert perspectives, and measurement of referral quality, branded search, and target-account engagement from AI-driven discovery channels.
About League
League is one of the fastest-growing technology companies in Canada and the leading healthcare experience platform. Getting healthcare is often the easy part — finishing it is where things fall apart: people book the appointment and skip the follow-up, fill the prescription and stop taking it, get the referral and never make the call. That gap costs health plans and health systems money, and it costs people their health. League closes that gap — identifying what each person needs to do next, clearing what’s in their way, and getting it done, for the 70 million+ people whose care already runs through our platform. Health plans and health systems trust us to do this at scale. Organizations like Manulife, SCAN, Geisinger, and Medibank on the payer side, and Baptist and Shoppers Drug Mart on the provider side.
Position Summary:
This is a builder role, not a maintainer role — equal parts strategy and execution. You’re the most senior growth marketing hire on a team that’s re-building its demand generation engine. You’ll have the budget, a team, and direct access to leadership to do it.
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.
What You’ll Do:
- 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
- Own the AI-Native Workflow strategy and AI Engine Optimization (AEO): as buyers increasingly use LLMs to research vendors, you have ideas on how to build League’s presence in those results
- Strategically partner cross-functionally with Sales, Product Marketing and Revenue Operations
Security-Related Responsibilities
- Compliance with Information Security Policies
- 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
What You’ll Bring:
- 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; payer or provider experience is a strong plus
- 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
- Strategic and hands-on: you’re equally excited to set the plan and execute it
- 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. 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
$145,000—$170,000 CAD
AI Fluency & Ways of Working
At League, we are an AI-native organization. We expect all employees regardless of role or level to thoughtfully leverage AI to improve the quality, speed, and impact of their work.
What this means in practice:
- Use AI tools as part of your daily workflow to enhance productivity, problem-solving, and decision-making (e.g., drafting, analysis, coding, research, or process automation)
- Apply judgment and accountability when using AI by reviewing outputs for accuracy, bias, and quality before use
- Continuously learn and adapt as new AI tools and capabilities emerge, incorporating them into your ways of working
- 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
How this scales by level:
- Individual Contributors: Use AI to improve personal productivity and quality of output
- Senior ICs / Managers: Integrate AI into team workflows and improve processes
- Leaders: Drive AI adoption at the organizational level and shape how work is done across teams
What we look for:
- Demonstrated experience using AI tools in a practical, responsible way
- Curiosity and openness to experimenting with new technologies
- Ability to balance efficiency with quality and sound judgment
Our 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 recruitinginfo@league.com.
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:
- Learn about our platform, leadership team and partners
- Highmark Health, Google Cloud, League: new digital front door to seamless care
- Former Providence President and Workday EVP of Corporate Strategy join League Board of Directors
- League raises $95 million USD in Series C to build world’s leading healthcare CX platform
- Forbes x League: The Platformization Of Healthcare Is Here
- Fast Company x League: If we want better innovations in healthtech, we need more competition
Work Location:
We have a mix of office-centric roles based in our vibrant Toronto office, and remote-eligible roles based anywhere in Canada or US. Each job posting will indicate where the role will be based. 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. We are committed to fostering a meaningful work environment and connections for all Leaguers regardless of location.
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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 here.
Privacy Policy
Review our Privacy Policy for information on how League is protecting personal data.
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