League is hiring a Technical Delivery Project Manager (Talent Pool Building)

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 a Technical Delivery Project Manager, you support the successful execution of internal technical workstreams required for customer delivery. You serve as the day-to-day liaison between internal technical teams (e.g., Data Engineering, Data Science, Integrations, R&D) and the customer-facing delivery team. You coordinate technical requirements, gather inputs from customers, help translate requirements into internal technical tasks, manage supporting documentation, and ensure technical deliverables are completed on time. In this role, you work closely with the Delivery Lead and functional technical leads to ensure alignment, visibility, and smooth execution of technical dependencies. You apply strong working knowledge of tools like Jira and foundational technical literacy to understand and communicate risks, issues, and timelines. You operate with growing independence while receiving guidance for complex or ambiguous matters. One specific area of responsibility is to manage League’s customer-facing data product called Analytics Objects (AOs), which is a recurring data export of complex KPIs configured to meet a wide range of customer requirements. Your responsibilities include: In this role, you are expected to: Technical Workstream Coordination Coordinate technical tasks and dependencies across Data, Engineering, R&D, and other internal technical teams. Translate customer requirements into clear Jira tickets or internal work items. Maintain visibility into task progress, blockers, and timelines. Manage Data Products Coordinate launch of Analytics Objects (AOs) and other data products to customers. Manage the configuration of AOs and other data products to suit customer use cases. Manage customization requests and recommend existing solutions to customers as needed. Coordinate with product managers on custom solutions. Customer Engagement & Requirements Gathering Attend customer-facing technical requirement meetings as a supporting point of contact. Document technical requirements and ensure internal technical teams understand expected outcomes. Communicate updates, risks, and next steps back to customer-facing stakeholders. Jira & Tooling Ownership Support maintaining Jira boards, grooming tasks, updating statuses, and ensuring accurate workflow progression for tasks related to customer delivery. Support reporting on technical delivery progress and timelines. Risk & Issue Management Identify and flag risks or blockers related to technical workstreams. Escalate issues to the Delivery Lead or technical leads as needed. Technical Delivery Support Support internal test cycles, data validation activities, and technical documentation requirements. Understand and articulate the impact of deviations from standard practices. Process & Documentation Maintain technical requirement documentation, task tracking, and workstream-level artifacts. Contribute feedback to help improve technical delivery processes and tooling. About You: 3+ years in SaaS technical coordination, technical support, or data operations. Working knowledge of data platforms (Airflow, BigQuery, Looker, or similar). Strong proficiency with Jira for workflow tracking and ticket management. Foundational understanding of SaaS architectures, APIs, data pipelines, or ETL. Experience collaborating with Data teams, R&D, or technical SMEs. Experience managing projects with complex technical dependencies. 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: We’re always excited to connect with exceptional talent. This posting is part of our proactive talent community efforts. While there may not be an immediate opening, we review applications on an ongoing basis and reach out as opportunities arise. 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