Head of AI Engineering & Enablement

Tebra only initiates contact with candidates via email from an official Tebra email address (@tebra.com, @patientpop.com, or @kareo.com) or through our applicant tracking system, Greenhouse. We will only ask you to provide sensitive personal information through our official application portal — not via social media or text message. We do not conduct interviews via instant messaging.

About The Role

We are hiring a hands‑on player coach to lead AI across how Tebra runs as a company. You will be building alongside a small team of one to two engineers while simultaneously leading process re‑engineering engagements with functional leaders. You will ship code, design agents and re‑engineer workflows, while also leading the team around you.

With a small team, this role will focus on our internal operations — not the AI in our product. It covers how every function works, how fast we move, and how much leverage each person has. As we scale toward $300M+ in ARR, the goal is to decouple growth from headcount and build an operation that runs leaner as it gets bigger.

Most of the value comes from re‑engineering the work itself, so you will pair deep engineering and applied AI skill with strong business judgment and a relentless focus on outcomes.

Your Area of Focus

AI Strategy & Use Case Discovery

• Work with the CEO, CFO, and CPO to identify where AI can drive the greatest efficiency and operating leverage across the organization, and prioritize accordingly.
• Audit and re‑engineer business processes before automating them, so we improve how the work is done and not just how fast it runs.
• Build and maintain an AI Opportunity roadmap that prioritizes use cases by ROI, feasibility and strategic impact in partnership with the functional leaders.

Build the Hardest Workflows

• Perform deep‑dive assessments to identify the highest‑impact efficiency opportunities across all operating functions — then build them, don't just document them.
• Design and build high‑value internal agents and automations that address the hardest problems inside our operating functions. Stay hands‑on in the build yourself; this is not a role where you commission others and review outputs.
• Own the shared patterns for retrieval, agent design, and secure system‑of‑record connectivity — including MCP servers, agent‑to‑agent orchestration, and API integrations — with permission‑aware access across Gong, Salesforce, NetSuite, Snowflake, Slack, and Workato.
• Design multi‑agent systems where specialized agents hand off to each other across workflow steps, not just single agent automation.
• Build and maintain the organizational context layer, the connective tissue that makes Tebra queryable; meeting capture, knowledge connectors, MCP servers into our core systems and permission aware retrieval so agents and people have a single source of truth.
• Develop and maintain a library of reusable skills, frameworks, and how‑to guides, allowing one person’s breakthrough workflow to scale to the entire organization and the programs to compound over time.
• Own the full lifecycle from rapid prototyping to production‑grade deployment, including monitoring, evaluation frameworks, error handling, and iteration based on real usage data.

Governance

• Define the approved tools, data‑handling rules, build standards, and a shared reference architecture for AI across Tebra's operating functions, in partnership with Legal and Security.
• Own how agents are deployed and monitored once live, ensuring full HIPAA compliance and strict adherence to our data privacy and security policies for PHI, without slowing teams down.
• Stand up an AI risk register, acceptable use policy, and audit trail standards for all production agents, and maintain them as the tooling landscape evolves.

Enable the Functions

• Partner with each function to find high‑value use cases and help them build and ship the more routine, accessible agents themselves.
• Coach AI owners inside each function, and run enablement and fluency programs so adoption scales beyond the central team.
• Build genuine on‑ramps for less‑technical teams: role‑specific training, prompt libraries, office hours, and ready‑to‑use templates that make AI approachable across every level of the org.
• Continuously identify emerging AI tooling, methodologies, and agent frameworks — evaluate new models and techniques to keep Tebra ahead of the curve.

Your Professional Qualifications

Technical Foundation

• 8+ years in software engineering, applied AI, or technical product roles, with a meaningful stretch spent hands‑on and building in production — not directing from a distance.
• An engineering background you still use. You can read and write code and ship production systems, not only manage people who do.
• Deep applied AI experience designing and deploying multi‑agents systems, RAG pipelines, agent‑to‑agent orchestrations, MCP servers, and API integrations into systems of record, and LLM‑based workflows in production.
• Hands‑on experience shipping AI in a HIPAA‑regulated or comparable environment — working within BAAs, maintaining audit trails, and keeping PHI out of non‑covered tools.

Business & Operational Judgment

• A track record on operationally focused technology projects — workflow automation, systems integration, internal tooling — that demonstrably changed how a business runs.
• Strong business acumen. You can sit with a function leader, understand their workflow end‑to‑end, and translate it into the right automation — including knowing when the right answer is to redesign the process first.
• A process re‑engineering instinct, with the judgment to fix the work before automating it.

Change Leadership & Adoption

• A proven track record of driving adoption and behavior change within non‑technical teams — not just shipping the tools, but building champions, running training, and sustaining usage until it becomes a habit.
• Experience leading a small team and coaching others to build while staying hands‑on yourself.
• Excellent communication. You can brief the CEO and pair with an engineer on the same day, and those conversations feel equally natural.

Our Values

Start with the Customer: We get to know our customers — and their patients — and look at the world through their lens.

Keep It Simple: Healthcare is too complex. We aim to simplify it for everyone.

Stay Entrepreneurial: We reject the status quo and solve problems with creativity, perseverance, and a bias to action.

Better Together: We are diverse, humble, and collaborative. We put the team first and win together.

Celebrate Success: Life is short and joy is underrated. We take time to have fun and celebrate success.

About Tebra

Tebra is the only all‑in‑one EHR+ platform built exclusively for independent healthcare practices. Designed to replace the clunky, fragmented tools built for corporate systems, Tebra connects EHR software, billing, automation, telehealth solution, and marketing — so providers can spend less time on admin and more time with patients. More than 42,000 private practices trust Tebra to streamline operations, increase revenue, and reduce burnout — helping clinicians leave work on time and rediscover their purpose. Learn more at

Perks & Benefits

United States: In addition to our healthcare benefits, we also offer amazing perks! Need work from home basics? We offer a discount through Dell! We also offer a number of resources to help you keep your mind and body healthy. Check out Gympass for a great workout, or Telus Employee Assistance Program to find mental health resources, along with other resources for everyday occurrences.

Costa Rica: To assist with all of life’s needs, Tebra also offers a wellness and childcare subsidy and a University/Education discount! We also offer a number of resources to help you keep your mind and body healthy. Check out Gympass for access to health and fitness apps, or Telus Employee Assistance Program to find mental health resources, along with other resources for everyday occurrences.

Compensation

Zone 1 (National Average): $224,000 USD - $256,000 USD

Compliance & Privacy Disclosures

NOTE: Tebra is an equal opportunity employer. All applicants will be considered for employment without attention to age, race, color, religion, sex, sexual orientation, gender identity, national origin, veteran or disability status.

California residents who apply or are recruited for a job with us: please carefully review our California‑specific Privacy Notice under the California Consumer Protection Act here:

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As part of our commitment to a fair and efficient hiring process, Tebra utilizes BrightHire, an interview intelligence platform, for our phone and video screenings. This technology records and transcribes interviews to help us ensure consistency, reduce bias, and make more informed hiring decisions. By applying for this position, you acknowledge that your interview may be recorded.