VP, Engineering (Apps & Solutions)

League Inc.

3h•Hybrid

About The Position

League is at an inflection point, undergoing a delivery transformation to an AI-native, industrialized model while scaling strategic enterprise accounts and new delivery capabilities. This VP role is crucial for shaping the future of engineering operations at League for the next five years. The ideal candidate is a seasoned engineering leader with strong AI conviction, responsible for setting the technical vision, owning end-to-end delivery for an organization of over 50 engineers, and driving an AI-native engineering transformation to enhance speed, reliability, and predictability. This role also involves managing executive-level relationships with League's most strategic enterprise clients and significantly influencing the company's software development direction.

Requirements

15+ years of progressive software engineering experience
8+ years in senior leadership roles managing multiple engineering teams and leaders of leaders
Demonstrated AI conviction and hands-on experience deploying AI-assisted engineering workflows (capacity matching, automated defect classification, PR review, agentic tooling)
Proven track record scaling engineering organizations of 50+ engineers
Experience delivering complex, enterprise-grade SaaS products in a B2B or B2B2C environment
Deep technical fluency in cloud-native architectures (GCP preferred), microservices, and full-stack development (Go, React, mobile)
Exceptional executive presence with the ability to build trust with C-suite stakeholders and enterprise customers
Track record of owning high-stakes customer relationships at the account level
Experience working within HIPAA, PIPEDA, or equivalent regulated data environments
Demonstrated experience managing delivery partners, offshore teams, or hybrid internal/external engineering models
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

Nice To Haves

Health tech or enterprise healthcare SaaS experience strongly preferred

Responsibilities

Lead the AI-native engineering transformation for Apps & Solutions, driving adoption of micro-sprint methodologies, agentic capacity management, and AI-informed delivery decisions across all engineering pods, aiming for over 40% AI-informed delivery decisions.
Build and scale a world-class engineering organization of over 50 engineers, leading through Directors and Engineering Managers, developing the EM cohort, and building a leadership bench for sustained delivery excellence.
Set the technical vision and engineering standards for Apps & Solutions, aligning architecture with business objectives and product roadmap, and championing CI/CD, observability, cloud-native engineering on GCP, and test automation.
Own executive-level customer relationships as the senior engineering sponsor for strategic enterprise accounts, managing escalations, delivery confidence, and client relationships.
Partner at the company-wide level with the CTO, CPO, and CDO to shape technology strategy, architecture, and go-to-market execution, owning P&L accountability for engineering delivery.
Drive cross-functional alignment at the leadership level with the CPO, CTO, and CDO, ensuring engineering decisions align with product roadmaps and delivery capacity, and managing the relationship between engineering velocity and commercial feasibility.
Lead the Apps & Solutions organization through an AI-native delivery transformation, making micro-sprints, agentic capacity management, AI-informed PR review, and defect classification operational realities.
Champion AI tooling adoption across engineering pods (Copilot, LLM-assisted workflows, AI-driven observability) and foster a culture of AI fluency.
Use AI actively in strategic work, including synthesizing delivery data, accelerating architectural thinking, and staying ahead of market and tooling evolution.
Define and own the organization's posture on responsible AI adoption at scale.
Integrate AI into daily workflows and maintain ownership and judgment over AI-generated outputs.
Comply with Information Security Policies, League's secure coding practices, and ensure access management compliance.
Notify HR, Legal, Compliance & Security of any incidents, breaches, or policy violations.