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
- 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% Final compensation will be determined based on location, experience, and qualifications.
