Senior AI Enablement Engineer

At Counterpart Health, we are transforming healthcare and improving patient care with our innovative primary care tool, Counterpart Assistant. By supporting Primary Care Physicians (PCPs), we are able to deliver improved outcomes to our patients at a lower cost through early diagnosis and longitudinal care management of chronic conditions. We are seeking an Sr. AI Enablement Engineer to join our team. In this role, you will evaluate, configure, and deploy AI-powered tools that make our operations, product, support, implementations, sales, and other teams faster and more effective. You will work closely across the organization to identify high-leverage opportunities for AI tooling, from coding assistants and workflow automation to internal copilots and productivity tools, and make them work reliably and securely in our environment. This is a hands-on role embedded with the teams that run our business. The tools and technology exist — the hard part is sitting with people, understanding their workflows, and getting the right solutions into their hands. Sometimes that means configuring an off-the-shelf product, sometimes it means writing a little code or wiring up an MCP server. You will serve as the go-to resource for AI tooling across the product organization, staying current on the rapidly evolving landscape and translating new capabilities into practical workflows. As a Senior AI Enablement Engineer, you will: Evaluate and bring on new AI tools and platforms, assessing fit for the team's workflows, managing setup and configuration, and driving adoption across the product organization. Lower the barrier to entry for non-engineers to leverage AI tools by packaging environments, simplifying setup, and removing infrastructure friction that blocks adoption. Solve the IT and security challenges required to deploy AI tools in a healthcare environment, setting up authentication flows, managing access patterns, and ensuring compliance with organizational security standards. Collaborate across the business—including product, engineering, design, IT, operations, commercial, and leadership teams—to identify workflows that can be accelerated with existing AI capabilities and get those tools running for the team. Create documentation, guides, and training materials that make it easy for non-technical team members to adopt and get value from new tools. Troubleshoot and maintain the AI tooling stack, diagnosing issues independently and iterating on configurations based on team feedback. Success in this role looks like: You ship tools that people actually use. The team's daily workflows visibly improve because of the tooling you've introduced and enabled. You become the person the team comes to when they want to know "is there an AI tool for this?" — and you can get it running securely and quickly. You reduce friction in tool adoption. New AI capabilities go from "interesting demo" to "the team uses this every day" because you handle the infrastructure, security, and onboarding. You proactively identify opportunities. You don't wait to be asked — you see a workflow that could be faster, find the right tool, and make it available. You manage your own work independently, communicating progress and surfacing blockers early without needing regular direction. You build trust across teams by delivering reliable, well-documented, and secure tooling setups and being responsive to feedback. You should get in touch if: You are automating everything you touch with AI today. We don’t care if you’re in engineering, product, IT, or anything else. We care that you are building daily and fast. You are deeply familiar with the current AI tooling landscape, LLMs, coding assistants, automation platforms, API integrations, and understand what it takes to deploy them in an organizational setting. Build small tools, scripts, and integrations — including MCP servers and lightweight automations — to bridge the gap between off-the-shelf AI products and the way our teams actually work. You're comfortable working across enterprise infrastructure like containers, cloud platform administration, endpoint management, identity management, and compliance tooling. You are a self-starter who thrives with autonomy. You identify barriers to adoption, solve the infrastructure problem, and get the tool into people's hands. You communicate clearly and can translate technical capabilities into practical value for non-technical teammates. Benefits Overview : Financial Well-Being : Our commitment to attracting and retaining top talent begins with a competitive base salary and equity opportunities. Additionally, we offer a performance-based bonus program and regular compensation reviews to recognize and reward exceptional contributions. Physical Well-Being : We prioritize the health and well-being of our employees and their families by offering comprehensive group medical coverage that include coverage for hospitalization, outpatient care, optical services, and dental benefits. Mental Well-Being : We understand the importance of mental health in fostering productivity and maintaining work-life balance. To support this, we offer initiatives such as No-Meeting Fridays, company holidays, access to mental health resources, and a generous annual leave policy. Additionally, we embrace a remote-first culture that supports collaboration and flexibility, allowing our team members to thrive from any location. Professional Development : We are committed to developing our talent professionally. We offer learning programs, mentorship, professional development funding, and regular performance feedback and reviews. Additional Perks: Reimbursement for office setup expenses Flexibility to work from home, enabling collaboration with global teams Paid parental leave for all new parents And much more! About Counterpart Health: In 2018, Clover Health set out to do something unprecedented: build a clinically intuitive, AI-enabled solution that fits within physicians' workflows to help support the earlier diagnosis and management of chronic conditions. Years later, that vision is a reality, with thousands of practitioners using Counterpart Assistant during patient visits to improve disease management, reduce medical expenses, and drive success in value-based care. With an exceptional team of value-based care and technology experts, Counterpart Health is driving value-based care at the speed of software. Counterpart Health is a subsidiary of Clover Health. From Clover’s inception, Diversity & Inclusion have always been key to our success. We are an Equal Opportunity Employer and our employees are people with different strengths, experiences, perspectives, opinions, and backgrounds, who share a passion for improving people's lives. Diversity not only includes race and gender identity, but also age, disability status, veteran status, sexual orientation, religion and many other parts of one’s identity. All of our employee’s points of view are key to our success, and inclusion is everyone's responsibility. #LI-REMOTE Pursuant to the San Francisco Fair Chance Ordinance, we will consider for employment qualified applicants with arrest and conviction records. We are an E-Verify company. Final pay is based on several factors including but not limited to internal equity, market data, and the applicant’s education, work experience, certifications, etc. A reasonable estimate of the base salary range for this role is: $140,000 — $175,000 USD