Senior Software Delivery Program Manager (Talent Pool Building - Toronto)

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.

The Role

As Software Delivery Project Manager, you are responsible for managing multiple concurrent projects and/workstreams in a complex program to facilitate an efficient and successful product implementation and customer onboarding process, with minimal support and supervision.

Your main objective is to proactively and strategically manage new customer implementations, creating end-to-end project plans, facilitating the execution of deliverables, keeping stakeholders informed of status and risks, coordinating actions with internal departments to fulfill client needs, and tracking progress against plan. It is vital to have strong customer facing communication skills and an ability to identify and escalate barriers to project success. You will act as a primary liaison between our customer and League's cross-functional teams. You will be required to manage both technical and non-technical discussions, including clear articulation of issues and risks that arise and translate those issues and risks into actionable deliverables and oversee their resolution.

In this role, you will:

• Act as a strategic and trustworthy partner between your client and League during the onboarding process

• Accountable for the creation and management of one or more project plans, status reports, and risk and issue logs

• Manage program calendar and meeting schedule to track towards timely execution of implementation

• Collaborate with a cross functional team, during a project to inform various stakeholders of upcoming tasks, project status and escalating issues when necessary

• Demonstrate the ability to motivate and guide internal teams to deliver according to plan, including but not limited to:

• Marketing and Communication teams in regards to communications and engagement strategy

• Product and Engineering teams for discovery meetings and delivering to customer requirements

• Operation teams to ensure proper processes are in place post launch

• Lead client discussions on implementation and/or project activities

• Demonstrate core problem solving skills to support the delivery of a successful implementation and product development when faced with uncertainty

• Support identifying dependencies and coordinating with your cross-functional teams to ensure attainment of dependencies and mitigation where appropriate to ensure delivery scheduled adherence

• Support change control processes and governance meetings to ensure alignment and integrity of the project scope and timeline

• Support Testing initiatives across the implementation lifecycle and act as the liaison with the customer for League's testing resources

• Proactively reach out to clients & decision makers to manage expectations and drive accountability

• Manage deliverable and document control process throughout implementation phases

• Capture ongoing and post-onboarding customer feedback, and initiate CSAT survey to contribute to Implementation Team’s ongoing process enhancements

• Foster referenceable clients who are openly willing to speak about their onboarding experience

• Project management best practices and apply tools and processes per internal standard

• Partner with Delivery Lead to communicate and escalate barriers to ensure project success

• Support internal initiatives to develop or improve documentation and processes that contribute to League’s delivery model

About You:

• 3-5 years experience in a high-performance implementation capacity

• 5+ years of project management experience preferred

• Bachelor’s degree or equivalent

• Experience in the healthcare, consumer applications or technology required

What We Offer

• Comprehensive Health Benefits: We prioritize your well-being with complete medical, dental, and vision coverage

• Bonus Program: Be rewarded for your contributions with our performance-based bonus program

• Employee Stock Option Program: Become an owner and share in our success through our stock option program

• Unlimited Paid Time Off: Take the time you need to recharge and maintain a healthy work-life balance

• Spending Accounts: Manage your healthcare and dependent care expenses with tax-advantaged spending accounts

• Wellness Days: Prioritize your mental and physical health with dedicated wellness days throughout the year

• Growth Opportunities: We invest in your future with abundant opportunities for professional development and advancement

• Mentorship Program: Benefit from guidance and support from experienced leaders in your field

Security-related Responsibilities

• Compliance with Information Security Policies

• Compliance with League’s secure coding practice

• Responsibility and accountability for executing League's policies and procedures

• Notification of HR, Legal, Compliance & Security of any incidents, breaches or policy violations

Please note: This is an evergreen role as we are building a talent pool of candidates.

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
$90,000—$110,000 CAD

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 [email protected].

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.

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