VP, Engineering – Apps, Solutions

League

VP, Engineering steering AI-native transformation for healthcare solutions platform. Leading a large engineering team and setting technical vision and standards.

Posted 4/24/2026full-timeRemote • 🇺🇸 United StatesLead💰 $290,100 - $354,500 per yearWebsite

Tech Stack

Tools & technologies

CloudGoGoogle Cloud PlatformMicroservicesReact

About the role

Key responsibilities & impact

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

What you’ll need

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

Comp & perks

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

ATS Keywords

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Applicant Tracking System Keywords

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Hard Skills & Tools

AI-native deliverymicro-sprint methodologiescapacity managementCI/CDcloud-native engineeringGCPtest automationfull-stack developmentGoReact

Soft Skills

executive presencetrust buildingleadershipcross-functional alignmentperformance managementcustomer relationship managementstrategic thinkingcommunicationteam managementchange management