Director/Sr. Director Engineering- Clinical AI + Care Delivery

Location: Palo Alto, California, United States, San Francisco, California, United States Director of Engineering, Clinical AI & Care Delivery Location: San Francisco Bay Area | Hybrid, 2 days/week in our San Francisco or Palo Alto office About Midi Health: Midi Health is transforming healthcare for women in midlife, delivering expert, personalized care through a virtual-first platform built around the needs of women in perimenopause and menopause. Technology is central not only to the patient experience, but to how our clinicians deliver exceptional care at scale. We believe AI will fundamentally reshape care delivery — reducing administrative burden, improving clinical workflows, and giving providers better tools to focus their time where it matters most: with patients. The Role: We’re looking for a Director of Engineering, Clinical AI & Care Delivery to lead the engineering teams behind the systems and tools that power Midi’s clinicians, medical assistants, and care workflows. This is a true player-coach role at the intersection of AI, healthcare, and software engineering. You’ll lead and develop a high-performing engineering team while staying close to the technology — shaping architecture, reviewing code, experimenting with AI and agentic systems, and helping your team solve complex problems. You’ll also be a senior engineering partner to Product, Clinical, Operations, Data Science, and other leaders across Midi. We expect our engineering leaders to think beyond their immediate teams and help shape how technology and AI can transform care delivery as Midi scales. What You’ll Own: Lead the engineering roadmap and execution for Midi’s clinician-facing tools, care delivery systems, clinical workflows, and AI-powered automation. Identify opportunities to use AI and agentic systems to automate workflows, augment clinicians, and improve the efficiency and quality of care delivery. Build and lead high-performing engineering teams with a culture of ownership, accountability, speed, and high technical standards. Stay hands-on through architecture decisions, code reviews, prototyping, and AI-assisted development. Partner closely with Product, Clinical, Operations, and Data Science to translate complex care delivery problems into scalable technical solutions. Drive engineering quality, velocity, reliability, and operational health across your area. Hire, mentor, and develop engineers and engineering leaders as the organization grows. Collaborate with engineering leaders across Midi on architecture, technical strategy, and company-wide engineering priorities. Help define how Midi uses AI and modern development tools to fundamentally rethink how healthcare is delivered. What We’re Looking For: Deep software engineering foundation. You’ve spent meaningful time as a senior individual contributor building sophisticated applications and systems. Proven engineering leadership. You have 5+ years of engineering management experience and have led organizations of 10+ engineers. Player-coach mindset. You’re comfortable operating at the leadership level while remaining technically credible and close enough to the work to help your team make better decisions. Applied AI experience. You’ve recently used AI coding agents or AI/LLM technologies to build something meaningful and have a practical understanding of what these technologies can — and cannot — do. Strong systems thinking. You can take complex, multi-step human workflows and think creatively about how technology and AI can make them dramatically better. Executive-level communication and judgment. You can confidently partner with senior technical, clinical, and operational leaders and communicate complex tradeoffs clearly. Exceptional cross-functional instincts. You naturally build trust with stakeholders who may approach problems very differently from an engineer. First-principles thinking. You ask the right questions, communicate clearly, and align early rather than building in isolation. Strong ownership mindset. You close loops, take accountability for outcomes, and step into problems rather than waiting for someone else to solve them. Nice to Have: Experience with AI/ML engineering, LLM-powered products, agentic systems, or workflow automation. Experience building internal tools or software for complex operational users. Experience with Python, Django, React, and AWS. Experience in healthcare or another highly regulated environment. Familiarity with EHRs such as Athenahealth, clinical workflows, or HIPAA-regulated systems. Experience building AI products where accuracy, reliability, human oversight, and trust are critical. Why Midi: This is an opportunity to work at the frontier of AI and healthcare while solving very real problems for clinicians and patients today. You’ll help determine how Midi uses technology to scale exceptional care — from automating repetitive workflows to building entirely new ways for clinicians and AI to work together. If you’re excited about building exceptional engineering teams, staying close to the technology, and applying AI to some of healthcare’s hardest operational problems, we’d love to hear from you. At Midi Health, we are committed to pay transparency and equity. The estimated salary range for this role is $230,000-325,000 per year, based on factors such as experience and skills. In addition to base salary, employees are eligible for a wide range of benefits and equity in the company, We believe in fair and competitive compensation practices that align with our values of equity and inclusion. If you have any questions about how we determine pay, we’re happy to discuss further in the hiring process. #li-JA1 At this time, Midi is unable to provide visa sponsorship. All Candidates must be authorized to work in the United States without current or future sponsorship needs. Please note that all official communication from Midi Health will come from an @joinmidi.com email address. We will never ask for payment of any kind during the application or hiring process. If you receive any suspicious communication claiming to be from Midi Health, please report it immediately by emailing us at careers@joinmidi.com . Midi Health is an Equal Opportunity Employer. We are committed to pay equity and ensure that all qualified applicants receive consideration for employment without regard to race, color, religion, sex, sexual orientation, gender identity, national origin, disability, or protected veteran status. Our compensation philosophy is based on fair, objective criteria and the impact of the role, regardless of an applicant’s salary history. Please find our CCPA Privacy Notice for California Candidates here .