Head OF Engineering

Building Healthcare That Remembers Every time you call a doctor's office, the system forgets you the moment you hang up. You wait on hold, explain everything from scratch, get bounced between lines, and hope someone follows up. Everyone has felt this. No one should have to. At Assort Health, we're building one continuous conversation for every patient. An AI agent that knows who you are, remembers how you like to be reached, and carries that context from your first symptom to your full recovery. What began as the first voice AI agent to schedule a specialty appointment has become the largest proprietary specialty dataset in healthcare: 240 million patient interactions, 62,000 care protocols, 1.6 million decision pathways. We went from 15 people in 2025 and will cross 250 by the end of 2026. Revenue is up 20x in 15 months and we've raised $222 million, including a recent $120 million Series C at a $1.2 billion valuation. We've also been named to the Forbes Cloud 100 and the 2026 Enterprise Tech 30 as the only healthcare AI company on the list! Healthcare spends $1.1 trillion a year on administration instead of care. If you want to help change that, About the Role As the Head of Forward Deployed Engineering at Assort Health, you'll build and lead the team responsible for turning our AI agent platform into production systems for our largest and most complex healthcare customers. Your team sits at the intersection of engineering, product, and customer success — owning the technical implementation of health system deployments, custom EHR integrations, and workflow builds that bring AI agents to life. You'll scale the FDE organization from a small team to 10+ engineers, establish repeatable deployment patterns, and create the feedback loop that turns field learnings into platform improvements. What You'll Do Scale the Forward Deployed Engineering team, including hiring, coaching, and developing a high-performing organization. Own end-to-end technical delivery for our most strategic customers. Partner closely with cross-functional teams to translate customer needs into scalable technical solutions and influence product roadmap based on field insights. Establish deployment patterns, best practices, and internal tooling that enable the FDE team to move faster and scale more efficiently. Drive the field-to-product feedback loop — identify patterns across implementations that should become platform features and work with product engineering to build them. Be hands‑on when it matters: lead technical discovery with strategic accounts, debug production issues, and set the technical bar for the team. What We're Looking For 5+ years of software engineering experience, with 2+ years leading customer‑facing technical teams Track record of scaling technical implementation or deployment teams in fast‑growing B2B or enterprise software companies Strong technical fundamentals with hands‑on ability to design, build, and debug production systems alongside your team Exceptional at balancing customer needs, technical feasibility, and engineering velocity — you know when to build custom vs. push for platform solutions Experience building repeatable processes and tooling to scale implementation work Outstanding communicator who can interface with C‑suite healthcare executives, technical teams, and internal stakeholders Willingness to travel to customer sites and be embedded with healthcare organizations during critical implementations Benefits & Perks for Assorties Competitive Compensation – Including salary and employee stock options so you share in our success. Lifelong Learning – Annual budget for professional development, plus training opportunities to help you grow. Office Setup Stipend – We’ll outfit your in-office workspace so comfy as it's productive. Top‑Tier Health Coverage – Medical, dental, and vision insurance, because your health comes first. Flexible PTO – We trust you to take the time you need to recharge and come back ready to crush it. Meals & Snacks – Lunch, dinner, and snack breaks that fuel great ideas. Fitness Stipend – Your wellness matters. We reimburse monthly membership costs to support your health. Commuter Benefits – We cover eligible transportation costs to make your trip to work easier. 401(k) – Build your retirement savings. How We Work & What We Value Our team at Assort Health moves fast, stays focused, and is fueled by a desire to serve our customers and patients. Our company values guide how we work—they are present in how we show up, make decisions and work together to move our mission forward. We bring a Day One Drive , relentlessly striving to improve, keep a 5-Star Focus , as our customers are our lifeblood, always Answer the Call , remembering that ownership and accountability are paramount, and show up with One Pulse , because we are one team, with one rhythm and one result. Our team is growing and we are looking for motivated, hardworking, and passionate talent. If you want to make healthcare accessible for everyone, we’d love to hear from you! Please note: the Assort Health Talent Team will only email you from an assorthealth.com email address. #J-18808-Ljbffr