Head of Engineering (Full-Time)

About Diana Health:

Diana Health is a network of modern women’s health practices working in partnership with hospitals to reimagine the maternity and women’s healthcare experience. We are restructuring the traditional approach to care to create an experience that is good for patients and good for providers. We do that by combining a tech-enabled, wellness-focused care program that women love with a clinical system that helps us drive continuous quality improvement and ensure work-life balance for our care team. We work with clients across all life stages to empower and support them to live happier, healthier, more fulfilling lives. 

We are an interdisciplinary team joined together by our shared commitment to transform women’s health. Come join us!

Role Description:

Diana Health is seeking a strategic and execution-focused Head of Engineering to lead a high-performing, cross-functional team driving our digital platform strategy.

This role is central to our next chapter of scale—responsible not just for technical oversight, but for aligning engineering with business outcomes, patient experience, and data-driven innovation. You’ll partner closely with product, analytics, and operations teams to ensure Diana Health’s technology is secure, scalable, and deeply aligned with our clinical and operational goals.

You’ll inherit a stable, globally distributed team and a modern mobile tech stack—and take it to the next level with clear systems, sustainable velocity, and strong cross-functional collaboration. This is a critical leadership role at the intersection of engineering excellence and mission-driven impact.

What you’ll do:

• Drive Diana Health’s technical strategy and execution, ensuring scalability, stability, and security of our digital infrastructure.
• Lead and coach a globally distributed engineering team, fostering autonomy, collaboration and accountability for digital solutions.
• Partner closely with Product, Operations, Analytics, Marketing and Executive Leadership to align Engineering with business and patient impact goals.
• Collaborate with product management to support product visioning, scoping and roadmap planning. 
• Guide cross-functional sprint-level planning, execution to quarterly delivery and annual roadmap alignment.
• Architect and own backend systems, mobile platforms, data flows, and integrations with internal & 3rd party vendors/tools (e.g., EHR, CRM, PRM, AI Scribe, self-scheduling etc.)
• Champion a proactive engineering culture of quality, experimentation, and continuous improvement.
• Maintain high standards for security, HIPAA compliance, and data integrity across platforms.
• Support product evaluation and technical vendor selection using engineering lens in collaboration with product leadership.
• Report regularly on delivery performance, engineering KPIs, and team health to executive leadership.

Requirements

• 8-10+ years of experience in software engineering, with at least 3 years in a senior leadership role. 
• Proven success managing remote, cross-functional engineering teams and creating high-performing collaborative delivery cultures.
• Deep technical expertise in modern mobile tech stacks (like Python, React Native and related), cloud infrastructure (AWS preferred), and API first design. 
• Previous experience in regulated industries, ideally healthcare tech; familiarity with HIPAA compliance
• Experience integrating with EHRs or other 3rd party health information systems.
• Demonstrated ability to collaboratively partner with product, analytics, and business teams to shape strategy.
• Strong system thinking, problem solving and communication skills.
• Experience leading vendor evaluations and integration oversight.
• Ability to make decisions and pivot quickly.
• Excited about working in a fast-paced environment.
• Passion for patient-centered technology and women’s health innovation.

Benefits

• Competitive compensation
• Medical, dental, and vision insurance, with an HSA/FSA option
• 401(k) with employer match
• Paid time off
• Paid parental leave 

Diana Health Culture

• Having a growth mindset and striving for continuous learning and improvement
• Positive, can do / how can I help attitude
• Empathy for our team and our clients
• Taking ownership and driving to results
• Being scrappy and resourceful