VP, Engineering – Apps, Solutions

🕒 April 24

🇺🇸 United States – Remote

💵 $290.1k - $354.5k / year

⏰ Full Time

🔴 Lead

🖥 Software Engineer

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League

WebsiteLinkedInAll Job Openings

501 - 1000 employees

Founded 2014

⚕️ Healthcare Insurance

☁️ SaaS

🤖 Artificial Intelligence

Healthcare Insurance • SaaS • Artificial Intelligence

League is a leading healthcare technology company that provides a platform designed to transform the healthcare consumer experience. Its platform offers digital infrastructure for data-driven, personalized consumer interactions, enhancing engagement and satisfaction for health plans, payers, and providers. League's solutions focus on creating innovative member experiences, acting as a digital destination for consumer health, and providing omni-channel patient experiences. With a focus on data security and compliance, the platform supports personalized care and modernizes healthcare interactions using data and AI. Additionally, League collaborates with partners to enrich the healthcare ecosystem and facilitates technology teams in developing their own solutions through its developer program.

📋 Description

• Lead the AI-native engineering transformation for Apps & Solutions — drive the adoption of micro-sprint methodologies, agentic capacity management, and AI-informed delivery decisions across all engineering pods; set a target of 40%+ AI-informed delivery decisions across the portfolio and build the operating model that makes it real, not aspirational • Build and scale a world-class engineering organization — lead 50+ engineers through multiple Directors and Engineering Managers, manage through leaders of leaders, develop the EM cohort as a performance management discipline, and build the leadership bench that sustains delivery excellence through growth and change • Set the technical vision and engineering standards — define the architecture direction for Apps & Solutions aligned with League's business objectives and product roadmap; champion CI/CD, observability, cloud-native engineering on GCP, and test automation practices that drive measurable quality improvement across all squads • Own executive-level customer relationships — serve as the senior engineering sponsor for League's most strategic enterprise accounts; own escalation management, delivery confidence, and the executive relationships that determine whether clients stay, expand, or churn • Partner at the company-wide level — work alongside the CTO, CPO, and CDO to shape technology strategy, architecture decisions, and go-to-market execution for enterprise customers; own P&L accountability for engineering delivery across the Apps & Solutions portfolio • Drive cross-functional alignment at the leadership level — work closely with the CPO, CTO, and CDO to ensure engineering decisions are tightly coupled to product roadmap commitments and delivery capacity; own the relationship between engineering velocity and commercial feasibility before commitments leave the building.

🎯 Requirements

• 15+ years of progressive software engineering experience, including 8+ years in senior leadership roles managing multiple engineering teams and leaders of leaders • Demonstrated AI conviction — you lead AI-native delivery in practice, not just in aspiration; you have hands-on experience deploying AI-assisted engineering workflows (capacity matching, automated defect classification, PR review, agentic tooling) and a track record of pulling engineering organizations forward on AI adoption • Proven track record scaling engineering organizations of 50+ engineers and delivering complex, enterprise-grade SaaS products in a B2B or B2B2C environment; health tech or enterprise healthcare SaaS experience strongly preferred • Deep technical fluency in cloud-native architectures (GCP preferred), microservices, and full-stack development (Go, React, mobile) — you engage credibly with engineers on architectural trade-offs without losing your strategic altitude • Exceptional executive presence with a demonstrated ability to build trust with C-suite stakeholders and enterprise customers; track record of owning high-stakes customer relationships at the account level, not just in QBRs • Experience working within HIPAA, PIPEDA, or equivalent regulated data environments is required at this level — you understand the compliance obligations that come with handling PHI and have built engineering practices that treat security and data governance as foundational, not afterthought • Demonstrated experience managing delivery partners, offshore teams, or hybrid internal/external engineering models; comfort holding external teams to the same quality bar as internal engineers.

🏖️ Benefits

• Health insurance • Retirement plans • Paid time off • Flexible work arrangements • Professional development • Bonuses • Stock options • Equipment allowances • Wellness programs