Director, Platform Sales

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:

League’s digital health footprint is strategically scaling. Building on the proven success among our market-leading customers and partners in Canada and the US, our Go-to-Market team is expanding and seeking a Director, Platform Sales to help us achieve this next phase of growth.

As a Director, Platform Sales , you will be a core part of the Go-to-Market team working across priority segments including public sector, healthcare providers, insurers, pharmacy retailers and digital health innovators. You will be responsible for leading complex enterprise-scale business development and sales initiatives with prospects and carry a quota for our consumer experience platform sales.

Working in collaboration with other parts of the Go-to-Market team (including Solution Engineering, Partnerships, Product Marketing), you will strategize, scope and design impactful customer partnerships that power the digital transformation of their consumer, member or patient experience.

In this role you will:

• Focus on expanding League’s footprint in Canada and building on the success of existing customer relationships. • Lead and own the end-to-end sales process for target platform strategic accounts including formulating sales strategy, driving revenue growth and developing new customer relationships. • Leverage your own relationships to build pipeline, and work in partnership with the Business Development and Marketing teams to run account-based marketing campaigns that lead to closed revenue and quota attainment. • Successfully achieve and exceed budgeted sales objectives, and maintain sales forecast in an accurate and thorough manner. • Negotiate complex software and professional services agreements from initial stages through to completion. • Create demand by leveraging healthcare industry expertise and what the priorities from C-level executives are, uncovering business problems and matching them to our solution. • Work collaboratively with League Executives and Go-to-Market leaders to build the story and tailored materials for meetings with prospective accounts. • Work with the Go-to-Market leadership team to create and improve sales processes and buyer journeys, especially in new industry verticals. • Proactively identify and communicate product needs of Powered by League prospects and industry verticals to executive and product leadership. • Ensure and monitor successful handoffs of accounts from the sales process and into customer strategy and delivery. • 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

About you:

• 8+ years of experience in ‘Platform as a Service’ (PaaS) or ‘Software as a Service’ (SaaS), digital transformation and consumer & patient engagement sales within the Healthcare industry required
• Selling AI-powered solutions is also a requirement
• Previous experience in a consulting role focusing on digital health and consumer experience is a significant asset
• Knowledge of the healthcare industry, especially public healthcare services and provincial/territorial health plans
• A history of successful quota attainment in a complex sales environment
• Ability to win the support of key C-Suite stakeholders in large corporations
• Proficiency with Salesforce and sales acceleration tools
• Experience developing exceptional documentation for client presentations and webinars
• Bachelor's degree in Business or equivalent experience

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

$160,000 — $200,000 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