VP, Engineering

What You'll Do

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.

The Day to Day

• 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.

Minimum Qualifications

• 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.

Preferred Qualifications

• 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.

Annual Salary Range: $173,000 - $231,000. This position is also eligible for a target annual bonus of 30%