VP, Engineering (Apps & Solutions)

Position Summary

League is at an inflection point. We’re executing a delivery transformation — moving from reactive implementation to an AI-native, industrialized delivery model — at the same time as we’re scaling our most strategic enterprise accounts and standing up new delivery capabilities. This VP role is a defining hire: you’ll shape how engineering operates at League for the next five years, not just manage what exists today.

You are a seasoned engineering leader who leads with AI conviction — someone who doesn't just adopt AI practices but pulls the entire engineering organization forward through them. As VP Engineering, Apps & Solutions at League, you'll set the technical vision, own end-to-end delivery across a 50+ engineer organization, and drive an AI-native engineering transformation that makes League's delivery faster, more reliable, and more predictable. You'll own executive-level relationships with League's most strategic enterprise clients and be a defining voice in how League builds software for the next five years.

In this role you will:

• 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.

About you:

• 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

Desired Outcomes 

• Developer throughput and predictability: PR throughput per developer sustained at or above industry p75, with a clear trajectory toward p90
• Developer Experience Index (DXI): measurable quarter-over-quarter improvement, with named actions and owners
• Engineering quality: defect rate below p75 benchmark, high/critical incident rate below 10 per month, incident resolution SLA attainment at 100%
• Test automation coverage: 80%+ across the portfolio with quarterly delivery milestones
• AI-informed delivery: 40%+ of engineering delivery decisions AI-assisted within 12 months
• Customer satisfaction: NPS and CSAT scores for strategic enterprise accounts trending positive

AI Fluency (Core Competency)

• Lead the Apps & Solutions org through an AI-native delivery transformation — micro-sprints, agentic capacity management, AI-informed PR review and defect classification are operational realities under your leadership, not future-state aspirations
• Champion AI tooling adoption across engineering pods (Copilot, LLM-assisted workflows, AI-driven observability) and build a team culture where AI fluency is expected at every level of the engineering org
• Use AI actively in your own strategic work — synthesizing delivery data, accelerating architectural thinking, staying ahead of market and tooling evolution
• Define and own the org's posture on responsible AI adoption at scale — what to build with, what to evaluate carefully, and where human judgment must remain primary
• Integrate AI into your daily workflow, not just occasional use
• Maintain strong ownership and judgment over AI-generated outputs

Security-Related Responsibilities

• Compliance with Information Security Policies
• Compliance with League's secure coding practice
• 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

• 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

• 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

• 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