VP, Engineering

Strive Health•Quinte West, ON

1d•$173,000 - $231,000•Hybrid

About The Position

At Strive Health, patients come first. We’re on a mission to transform chronic conditions by identifying risk earlier, coordinating thoughtful care, and supporting people through every stage of their health journey. Our work reduces emergency visits, improves outcomes, and helps patients live fuller lives. You’ll work alongside passionate Strivers who care deeply about making an impact, show up for one another as One Team, and find ways to elevate the everyday. If you’re looking for meaningful work where your contributions truly matter, you’ll feel right at home at Strive! We are seeking a VP of Engineering to lead Strive’s software engineering organization through its next phase of scale, operating rigor, and AI-enabled modernization. This leader will ensure that product vision is realized through excellent execution, while building the systems, standards, and culture required for predictable delivery, strong cross-functional partnership, and durable technical quality. As a key member of the engineering organization and product development leadership team, you will help shape our team’s practices, talent, and architecture as Strive modernizes its platform, scales AI-enabled workflows, and improves the experiences of clinicians, patients, and internal stakeholders. We are looking for a candidate with strong leadership judgment, an entrepreneurial spirit, and excitement for the challenges that come with building and scaling a category-creating healthtech solution.

Requirements

14+ years combined of related education and software engineering experience, with significant time leading engineering organizations through scale, complexity, and organizational change.
8+ years as a people leader, with a proven track record of attracting, hiring, managing, developing, and aligning an engineering organization, including managing through engineering managers and directors.
Demonstrated success improving delivery predictability, execution rigor, and engineering quality across multiple teams or product areas.
Experience building, delivering, and maintaining multi-year technology roadmaps that support company strategy, product roadmaps, and platform modernization.
Experience building and evolving engineering operating mechanisms, including planning, estimation, sprint or flow management, release processes, quality controls, and incident response.
Strong written and verbal communication skills, with the ability to represent engineering credibly at the executive level and across highly cross-functional stakeholder groups.
Strong systems thinking, sound judgment, and problem-solving skills, including the ability to simplify complexity and make practical tradeoffs under ambiguity.
Internet Connectivity - Min Speeds: 3.8Mbps/3.0Mbps (up/down): Latency <60 ms.
Ability to travel and be onsite to meet business needs.

Nice To Haves

Significant experience as a technology leader in a growth-minded corporation, with at least 8 years in an engineering management role.
Experience in healthcare, healthtech, value-based care, or another regulated environment where privacy, compliance, and operational reliability materially shape engineering decisions.
Experience modernizing legacy systems or leading engineering through major platform transitions, interoperability-heavy environments, or complex integration work.
Experience introducing AI-enabled ways of working in engineering or digital product organizations, with a focus on measurable productivity and quality gains rather than novelty.
Experience partnering with product leadership and business stakeholders to deliver increasing value while balancing speed, quality, risk, and long-term maintainability.
High level of integrity and dependability with a strong sense of urgency, accountability, and results orientation.
Strong communication, negotiation, and influence skills, including the ability to lead with professionalism and sound judgment in sensitive cross-functional contexts.
Action-oriented and innovative, with the ability to translate broad goals into achievable steps and execution systems.
A commitment to quality that incorporates not only immediate delivery requirements, but also long-term reliability, scalability, and strong user experience.
Consistent track record of working across team boundaries to deliver excellent user experiences and durable technical outcomes across the stack.

Responsibilities

Recruit, develop, and manage top engineering talent capable of delivering high-quality, reliable, secure, and effective technology.
Coach engineering managers and senior individual contributors to become stronger leaders, operators, and technical partners, while building clear growth paths across the organization.
Build and continuously improve the engineering operating system across planning, estimation, sprint execution, release readiness, incident management, and post-launch follow-through.
Improve delivery predictability, throughput, and transparency so that engineering commitments are realistic, measurable, and well-communicated to stakeholders.
Develop and drive standards across software design, testing, code review, observability, security, privacy, compliance, and production support.
Partner closely with Digital Product, Analytics, Data Science, Clinical, Operations, Security, Legal, and executive leadership to help translate business priorities into executable roadmaps and high-impact technical plans.
Help define the architecture and delivery approach required to move Strive from fragmented point solutions toward a cleaner, more composable, and more AI-ready platform stack.
Support major modernization initiatives, including EHR and workflow platform evolution, data integration, interoperability, and engineering patterns that enable faster iteration without sacrificing reliability.
Build practical AI leverage inside engineering by standardizing where tools like coding assistants, summarization, documentation generation, debugging support, and architecture support improve quality and speed.
Put thoughtful guardrails, review expectations, and measurable outcomes around AI usage so that engineering gains real leverage rather than noise or rework.
Work effectively with external partners and consultants when helpful, while retaining clear internal ownership of architecture, prioritization, standards, and long-term maintainability.
Define the optimal engineering organization structure, leadership bench, and talent mix needed to support growth, delivery flexibility, and long-term platform evolution.
Help teams understand product vision and walk in the clinician’s shoes, delivering workflows and capabilities that make Strive Health programs more seamless, effective, and efficient.
Meet in person with internal and/or external stakeholders to facilitate team and business priorities and opportunities. Business travel may be required for opportunities to connect with stakeholders, serve patients, and attend Strive-sponsored team events.