Vice President, Engineering (Toronto, ON)
League
Toronto, ON, Canada
CAD 232,400-290,500 / year
Posted on Aug 20, 2025
About League
Founded in 2014, and with a total funding currently at $220 million; League is a platform technology company powering next-generation healthcare consumer experiences. Payers, providers, consumer health partners and employers build on League’s platform to deliver high-engagement, personalized healthcare experiences consumers love. Millions of people use solutions powered by League to access, navigate and pay for care.
The Role
We're looking for a highly skilled and experienced Vice President, Engineering to lead our team at League. This role demands a unique combination of technical depth, strategic leadership, and a customer-centric mindset. As our VP, Engineering within our Apps & Solutions team, you will be responsible for the overall technical direction and delivery of our client solutions, ensuring our teams are building and shipping high-quality output efficiently.
In this role, you will:
- Provide Technical Leadership: You'll be the technical expert, responsible for the overall client solution architecture and ensuring our teams maintain a high standard of technical excellence. You should have a strong technical background to effectively guide and mentor your team
- Drive Engineering Excellence: You will implement and refine effective team processes and rituals, establish systems for visibility (including key performance metrics), and ensure a culture of high-quality and efficient delivery
- Lead and Develop Your Team: You'll be a people leader who can build and manage a high-performing engineering organization. While you will hire and empower people to drive the day-to-day, you will need to have a deep understanding of their work to ensure they succeed
- Foster Cross-Functional Collaboration: You will be the key engineering partner for our product and customer teams, setting our engineers up for success. This includes the ability to push back and negotiate on scope, timelines, and technical requirements
- Manage Client Services: You will work directly with our customers, managing their expectations, handling escalations, and successfully negotiating de-escalation. You'll also be responsible for managing project delivery within budget, ensuring accurate estimations and scope management
- Embrace Complexity: This role is for a leader who thrives in a fast-paced environment with many parallel initiatives. You must be able to process a high volume of information and manage multiple projects simultaneously
About You:
- Strong technical skills with a proven track record of architecting solutions.
- Exceptional engineering leadership skills with experience in driving effective team processes and a focus on high-quality delivery.
- A natural people leader who is adept at building and developing high-performing teams.
- Extensive client services experience including managing customer relationships, handling escalations, and managing project delivery.
- High information processing ability and the capacity to handle many parallel tasks.
Nice to have:
- Experience in the health tech industry.
- Proven experience scaling an organization in a fast-paced environment.
Security-related Responsibilities
- 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
- Compliance with Information Security Policies
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
$232,400—$290,500 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 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
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 here. 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.
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.