Head of Engineering – Remote

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 managing small, distributed teams across geographies

Working knowledge of machine learning, RAG, and other AI concepts, with first-hand experience developing production-grade implementations leveraging these

Strong backend and systems experience, with comfort across the full stack; fluency with Flutter, React, and Java is required

Deep familiarity with modern cloud infrastructure (AWS strongly preferred), automated testing tools (e.g. Playwright, Testrail), logging/monitoring tools (e.g. Datadog, Mixpanel) is required

Comfort using (and enthusiasm for) modern AI-assisted development tools to increase leverage and velocity

Experience in digital health, health-tech, or healthcare services environments strongly preferred

$225,000 – $275,000 a year

Pay & Perks:

💻 Fully remote opportunity

🩺 Medical, dental, and vision insurance

📈 401K retirement plan with company match

🏝️ Up to 20 days of PTO per year + company holidays

👶 Up to 14 weeks of parental leave (12 for non-birthing parents)

🏡 Annual work from home stipend for remote employees