Senior AI Enablement Engineer

ABOUT PIVOTAL HEALTH

Pivotal Health is the leading technology platform that helps healthcare providers get paid fairly in an increasingly complex reimbursement landscape.

Today, many providers face persistent underpayment from health insurance companies, despite delivering high-quality care. While processes like IDR (Independent Dispute Resolution) were designed to promote fairness, they’re often administrative-heavy, time-consuming, and difficult to navigate without the right tools.

Pivotal Health combines software, data, and service into a seamlessly integrated, AI-driven platform that simplifies these complex reimbursement workflows. We help providers efficiently dispute underpaid claims, reduce administrative burden, and recover the reimbursement they’re entitled to; without adding more work to already stretched teams.

Our full-service IDR solution is just the starting point. We’re building solutions that enable providers to operate with clarity, control, and confidence across the reimbursement journey.

ABOUT THE ROLE

We’re hiring a Senior AI Enablement Engineer to help make Pivotal dramatically better at using AI across the organization.

This role sits on the AI/ML Engineering team and reports to the Head of AI/ML Engineering, but the scope is intentionally cross-functional. You will work closely with operations, customer success, product, engineering, and other internal teams to identify where AI can create leverage, prototype practical solutions, and help those teams adopt new capabilities successfully.

This is not a pure training role and it is not a pure platform role. It is a blend of consulting, building, enablement, and execution. The right person can spot repetitive work, understand how teams actually operate, move quickly to create a useful AI-powered solution, and then help that solution become durable through better tooling, patterns, and education.

We want someone who is truly AI-first in how they work. You should be a power user yourself, with strong judgment about where AI can create meaningful gains and where it is not the right answer.

WHAT YOU’LL DO

• Partner directly with internal teams to identify high-leverage opportunities for AI-powered workflows and automation.

• Build lightweight but useful AI solutions for internal users, then help turn the best ones into repeatable capabilities.

• Improve onboarding and enablement paths that help non-technical or less-technical teams use AI effectively.

• Develop patterns, starter workflows, templates, and guardrails that make AI adoption easier across the company.

• Work with the AI platform team to translate field needs into better internal tooling and reusable primitives.

• Act as a forward-deployed partner who helps unblock teams creatively and pragmatically.

• Run workshops, office hours, demos, or embedded enablement efforts where needed, but always anchored in real work and real outcomes.

• Help define what great AI-enabled work looks like across functions, not just inside engineering.

• Use AI deeply in your own workflow and model strong, practical usage patterns for others.

WHAT SUCCESS LOOKS LIKE

In the first 6 to 12 months, strong outcomes in this role would include:

• multiple internal teams becoming meaningfully more effective through AI-powered workflows

• a clearer onboarding path for employees learning how to use AI well at Pivotal

• reusable patterns and internal capabilities that reduce one-off AI experiments

• new internal tools or lightweight applications that unlock real operational leverage

• stronger feedback loops between internal users and the AI platform team

• a noticeable increase in the organization’s confidence and sophistication in using AI

WHO YOU ARE

• You are highly fluent with AI tools and use them deeply in your own day-to-day work.

• You are technical enough to build real solutions, not just recommend them.

• You enjoy helping other people become more effective and can work well with both technical and non-technical teammates.

• You have strong product and workflow instincts and can identify where automation or AI can actually change outcomes.

• You are comfortable in ambiguous environments where part of the job is finding the highest-leverage problems.

• You can move fluidly between prototyping, advising, teaching, and building.

• You care about practical adoption, not just technical possibility.

WE’D BE ESPECIALLY EXCITED IF YOU HAVE

• experience building AI-powered internal tools, workflow automations, copilots, or operational software

• experience in forward-deployed engineering, solutions engineering, internal tooling, or enablement roles

• experience working closely with operations, customer success, or business teams to improve workflows

• experience building with LLMs, agents, retrieval systems, or low-code / app-builder style tools

• experience creating onboarding materials, playbooks, templates, or internal training that actually gets used

• experience in startups or high-velocity environments where teams need leverage quickly

• experience in healthcare or other operationally dense industries

WHY THIS ROLE IS INTERESTING

• You’ll have influence across the whole company, not just within one product team.

• The work is unusually high leverage because success improves how many other people operate.

• You’ll get to blend building, enablement, and problem-solving in a way that most roles do not.

• The team is early enough that strong patterns and habits can still spread quickly.

• You’ll help shape what an AI-first company actually looks like in practice.

EXAMPLE TECHNICAL ENVIRONMENT

Our current environment includes technologies and patterns like:

• internal AI and agent systems

• Python services and internal tooling

• product and operational workflows with structured data and automation

• emerging platform capabilities for experimentation, observability, prompt management, and reusable AI tooling

You do not need to match this stack perfectly, but you should be comfortable learning quickly and building useful things in this kind of environment.

WHY YOU’LL LOVE WORKING HERE

We’re a collaborative, low-ego team on a mission to make healthcare reimbursement fairer for providers. While we primarily hire around our core hubs–Los Angeles and New York–we remain open to exceptional talent outside those regions. Remote and hybrid flexibility varies by role and team, and is outlined in each job description.

If you’re excited by solving complex problems and making a real-world impact, we’d love to hear from you.

Benefits Include:

• Competitive compensation, including equity

• Full health, dental, and vision coverage

• Retirement savings plan through 401(k)

• Flexible time off

• Opportunities for company-wide connection and events

Ready to Make an Impact?

We’re building something meaningful; and we want you on the team.

Bring your ideas, curiosity, and drive, and let’s transform healthcare reimbursement together.

EMPLOYMENT INFORMATION

Work Authorization

Candidates must be authorized to work in the United States without current or future employer sponsorship.

Equal Employment Opportunity

Pivotal Health is an Equal Opportunity Employer. We celebrate diversity and are committed to creating an inclusive environment for all employees. We do not discriminate on the basis of race, color, religion, sex, gender identity or expression, sexual orientation, national origin, age, disability, veteran status, or any other legally protected status.

Reasonable Accommodations

Pivotal Health provides reasonable accommodations for qualified individuals with disabilities in accordance with applicable laws. If you need assistance during the application or interview process, please let us know.

Background Checks

Employment is contingent upon successful completion of applicable background checks, where permitted by law.

At-Will Employment

Employment with Pivo