Lead, AI Software Engineer

As a Lead AI Software Engineer, you will serve as a senior individual contributor and player-coach in the AI CoE, partnering across Technology and the business to embed AI into how Strive builds products and delivers care-supporting tools. You will also help reshape the software development lifecycle itself. We are moving toward behavior-driven and spec-driven development, expanding our use of skills, agents, and MCP servers, and rethinking the merge request process so that AI-assisted code reviews coach junior engineers as well as critique their work. You will help define those changes — and then help the rest of engineering to adopt them. Because the AI CoE sits at the intersection of product, engineering, and clinical strategy, you will work closely with Product Management, the VP of Engineering, the VP of Product, and the Chief Technology Officer, as well as clinical and business stakeholders, to identify where thoughtful application of AI can produce real gains for the business and for the patients we serve. The Day to Day

• Coach and upskill engineers across Strive on AI-assisted coding, agentic workflows, and modern context engineering practices, with a focus on safe, repeatable patterns that teams can adopt independently. - Lead the rollout, configuration, and ongoing maturation of our AI-assisted development tooling (e.g., Claude Code), including experimentation with skills, agents, and MCP servers, and translating findings into best practices. - Help define and evangelize behavior-driven and spec-driven development practices, including AI-readable specs, architecture diagrams, and architecture decision records (ADRs) that make intent and context clear to both humans and AI. - Partner with engineering leadership to introduce AI-assisted code reviews into our GitLab merge request workflow, including patterns that provide coaching feedback for junior engineers while maintaining high quality and safety. - Design and build reference implementations of AI-forward applications — generative, agentic, and RAG-based — that demonstrate what is possible and create reusable patterns, libraries, and templates for other teams. - Collaborate with Product, the VP of Engineering, the VP of Product, the CTO, and other leaders to identify, prioritize, and sequence high-leverage AI opportunities in the product and platform roadmap. - Work closely with security, compliance, and data teams to ensure that AI tools and applications handling PHI and other sensitive data adhere to Strive’s security, privacy, and governance requirements. - Communicate complex AI topics clearly to non-technical audiences (including clinical and business stakeholders and senior executives), translating technical trade-offs into language that supports informed decision-making. - Contribute to standards and documentation for AI usage across engineering, including coding guidelines, prompt and context patterns, agent/skill catalogs, and runbooks for common AI-assisted workflows. - Meet in person with internal stakeholders to facilitate team and business priorities/opportunities, including training sessions, workshops, and demos, as needed. Minimum Qualifications

• 7+ years of experience in software engineering, data engineering, machine learning engineering, or a closely related field, preferably in healthcare or other regulated technology environments. - 2+ years of hands-on experience building and operating AI-powered systems (e.g., generative AI, agentic workflows, RAG applications), beyond surface-level usage of coding assistants. - Internet Connectivity - Min Speeds: 3.8Mbps/3.0Mbps (up/down); Latency < 60 ms. - Ability to travel and be onsite to meet business needs (up to 10% travel). Preferred Qualifications

• Demonstrated, hands-on experience with intermediate-to-advanced usage of AI-assisted coding tools (such as Claude Code, GitHub Copilot, Cursor, or similar), including configuration, prompt/context strategies, developing your own skills and subagents, and integration into the SDLC. - Strong Python skills with experience building cloud-based data and AI workflows (e.g., microservices, data pipelines, or orchestration using tools like AWS services, Airflow, or Step Functions). - Experience designing and implementing at least one flavor of Retrieval-Augmented Generation (e.g., vector RAG) and working familiarity with alternatives (graph or hybrid RAG), including when to apply each pattern. - Proven experience mentoring and coaching other engineers — providing design, code, and workflow feedback that improves both outcomes and skills over time. - Ability to communicate complex technical and AI concepts clearly to both technical and non-technical stakeholders, including clinicians and business leaders. - Hands-on experience with multiple AI coding assistants and frameworks (e.g., Codex, Cursor, GitHub Copilot, Gemini CLI), and familiarity with emerging spec-driven and agentic frameworks (e.g., GSD, Superpowers, Claude Flow). - Experience designing or consuming MCP servers, custom tools/skills, and multi-agent orchestration patterns in production or pre-production environments. - Strong context engineering instincts — shaping the SDLC (specs, ADRs, architecture diagrams, commit messages, runbooks) so that the why and what of a change are automatically available to AI agents. - Experience building generative or agentic AI applications that interact with real users (internal or external), including UX considerations, guardrails, and monitoring for safety and quality. - Practical experience with vector embeddings, knowledge graphs, or similar techniques for knowledge-base RAG systems, ideally supporting non-technical users such as clinical teams. - Strong AWS background, including experience with foundational services used in data and AI workflows (e.g., Lambda, containers, eventing/queues, data lakes, Redshift, Glue) and infrastructure-as-code (AWS CDK preferred). - Experience working with healthcare data standards (e.g., HL7 FHIR) and clinical stakeholders. - Familiarity with GitLab-based workflows (or transferable GitHub experience), including CI/CD, code review practices, and introducing new tooling or quality gates into an existing SDLC. About You

• You are energized by coaching and mentoring — you enjoy helping others build intuition about AI tools, not just handing them answers. - You are a curious, lifelong learner who actively explores emerging AI capabilities and thoughtfully evaluates when and how to apply them in a production environment. - You communicate politely, clearly, and precisely, and you are comfortable translating between deeply technical discussions and executive- or clinician-friendly language. - You celebrate diversity, equity, and inclusion, and you enjoy collaborating with colleagues from a wide range of backgrounds and disciplines. - You are self-motivated and detail-oriented, with a bias toward action and shipping incremental value safely. - You are team-first: you value shared wins, give and receive feedback openly, and help foster a culture of trust, fun, innovation, and continuous improvement. Annual Base Salary Range: $108,500 - $163,200. This position is also eligible for a target annual bonus of 10%

Final compensation will be determined based on location, experience, and qualifications. At this time Strive Health is unable to provide work visa sponsorship. Please apply even if you feel you do not meet all qualifications. If you require reasonable accommodation in completing this application, interviewing, completing any pre-employment testing, or otherwise participating in the employee selection process, please direct your inquiries to talentacquisition@strivehealth.com. We do not accept unsolicited resumes from outside recruiters/placement agencies. Strive Health will not pay fees associated with resumes presented through unsolicited means.