About League

League is a platform technology company powering next-generation consumer health experiences. Established in 2014, League's platform delivers highly personalized experiences that help people get more out of their health benefits while helping employers and organizations achieve better outcomes. Millions of people use products built on League's platform to access, navigate, and pay for care.

Position Summary

We are looking for a seasoned and highly capable Vice President, Engineering to lead our Apps & Solutions engineering organization. This is a senior leadership role that sits at the intersection of technical excellence, strategic delivery, and customer partnership.

The ideal candidate brings deep external client-facing experience, a strong foundation in technical engineering, and a proven ability to lead and scale high-performing engineering teams. You are as comfortable in a boardroom managing client escalations as you are in a technical design review - and you bring clarity and confidence to both.

Essential Duties & Responsibilities

Technical Leadership

Own the overall client solution architecture and set the technical direction for the Apps & Solutions team
Maintain and uphold a high bar for technical excellence across all engineering output
Actively guide, mentor, and support engineering leaders and individual contributors

Engineering Excellence

Implement and continuously refine team processes, rituals, and delivery frameworks
Establish robust systems for visibility, including engineering KPIs and performance metrics
Champion a culture of quality, accountability, and efficient delivery

People Leadership

Build, manage, and develop a high-performing, multi-layered engineering organization
Hire and empower leaders to drive day-to-day execution while maintaining strong organizational awareness
Coach and develop talent at all levels with thoughtfulness and intentionality

Cross-Functional Collaboration

Serve as the primary engineering partner for Product and Customer teams
Confidently negotiate on scope, timelines, and technical requirements to protect delivery integrity
Build trusted, collaborative relationships with peers across the organization

Client Services & Delivery Management

Manage direct client relationships with professionalism, managing expectations and navigating escalations effectively
Oversee project delivery within budget, ensuring accurate estimation and disciplined scope management
Represent engineering in client-facing conversations with clarity and credibility

Operational Complexity

Thrive in a fast-paced, high-volume environment with multiple parallel initiatives
Demonstrate high information-processing capability and sound prioritization judgment

Required Qualifications

Strong technical background with a proven track record of architecting and delivering complex solutions
Exceptional engineering leadership experience, including driving team processes focused on quality and delivery
Demonstrated success building and developing high-performing engineering teams
Extensive client services experience: relationship management, escalation handling, and project delivery ownership
High capacity for managing complex, parallel workstreams with composure and precision

Nice to Have

Experience in the health tech/software dev industry
Proven track record of scaling engineering organizations in high-growth, fast-paced environments

Key Competencies & Attributes

Genuinely aligned with League's mission to improve health outcomes through technology
Strategic mindset - able to focus self and team on the highest-impact priorities
Clear and effective communicator across diverse technical and non-technical audiences
Resilient and adaptable in dynamic, ambiguous environments
Results-driven with a high-performance orientation
Intellectually curious with a commitment to continuous learning and improvement