Head of Engineering

👋 Meet knownwell, weight-inclusive healthcare for all. Join a dynamic company that is changing the way obesity care is delivered. We offer weight management, primary care, nutrition counseling, and health coaching. Our care model combines in-clinic and virtual care to bring support to patients where and when they need it.
Backed by $50M in funding—including a $25M round led by CVS Health Ventures with support from a16z Bio + Health, Flare Capital, MassMutual, and Intermountain Ventures—we’re scaling fast and expanding access to evidence-based obesity care nationwide.
knownwell is seeking a hands-on Head of Engineering to lead the design, build, and evolution of our healthcare technology platform. This role is ideal for a senior engineering leader who still loves to code, thrives in early-stage environments, and wants to directly shape how modern healthcare services are delivered.
You will own end-to-end engineering execution—from architecting and building integrations with core healthcare systems (e.g., athenahealth APIs) to writing production code using the latest AI-assisted development tools, to hiring and leading a small, high-impact engineering team. You’ll partner closely with Product, Clinical, Data, and Operations leaders to ensure our technology meaningfully improves patient care and clinical workflows.

Roles & Responsibilities:

• Architect and build core components of knownwell’s healthcare services platform, including integrations with athenahealth’s scheduling, billing, and clinical workflows
• Write production-grade code yourself, leveraging modern AI coding tools (e.g., Cursor, Claude Code, Github Copilot, etc.) to move fast without sacrificing quality
• Make pragmatic architecture decisions that balance speed, scalability, security, and compliance in a healthcare environment

Platform & Systems Ownership
• Own full-stack delivery across backend services, frontend applications, infrastructure, and DevOps; experience with Flutter, React, and Java is required
• Ensure HIPAA-compliance as well as strong data privacy and security practices, leveraging a “secure by design” mentality and holding others accountable for the same
• Build processes to ensure application keys and certificates are maintained, avoiding single points of failure
• Monitor and optimize AWS cloud spend, as well as other cloud-based services, balancing performance and cost

Execution & Delivery
• Own the full engineering execution rhythm (planning, estimation, standups, reviews, retros)
• Partner with Product to translate roadmap into clear technical plans, milestones, and execution plans
• Drive predictable delivery through tight feedback loops, clear ownership, and a bias toward shipping
• Proactively identify risks and technical constraints, and course-correct quickly with open communication to partners and stakeholders
• Build and foster a culture of continuous improvement, leveraging modern approaches such as automated testing, CI/CD, and XP to enable quick iteration
• Identify and manage tech debt in a deliberate, strategic way, partnering with Product to balance long-term risk management with near-term business needs

Team Building & Development
• Hire, mentor, and lead a highly effective engineering team (which may include internal engineers and offshore contractors) with varying levels of experience
• Provide coaching, feedback, performance management, and professional development, with clear leveling, expectations, and ownership across engineers and projects
• Establish lightweight but strong engineering standards around code quality, testing, observability, and reliability
• Foster a culture of ownership, speed, continuous learning, and patient-centered thinking

Cross-Functional Partnership
• Work closely with Product, Clinical, Operations, and Data teams to deeply understand care delivery needs
• Translate real-world clinical and operational problems into scalable technical solutions
• Communicate clearly with both technical and non-technical stakeholders

Innovation & AI Enablement
• Actively explore and adopt emerging AI and automation tools to accelerate development and improve internal workflows
• Identify opportunities where AI can meaningfully enhance clinical operations, documentation, triage, or patient experience

Qualifications:

• 10+ years of software engineering experience, with meaningful time spent as a hands-on builder
• Experience leading engineering efforts at early- to growth-stage companies, including hiring and manag