AI Innovation Leader, Employee Benefits - Remote

Employee Benefits is the core of our business and at our heart we are a people-focused organization. Every day, we help over 100,000 employers give their employees peace of mind by providing health, pharmacy, long and short-term disability, vision, dental and other insurance solutions. What makes us unique is that we can surround our clients with more services and more technology-based tools and a team of advisors that simply cares more than anyone else. 

If you want a career giving people the reassurance that they can have access to the health care they need for themselves and their loved ones, join OneDigital.

Our Newest Opportunity: 

Summary:

The AI Innovation Leader is the embedded innovation leader for an assigned practice, driving practice-specific application of AI in partnership with OneDigital’s central AI Product Team. The role exists to accelerate AI adoption within the practice without adding to the National Practice Leader’s operational load.

The AI Innovation Leader is the connective tissue between the practice and the AI Product Team — translating practice priorities into a use case pipeline, leading practice-embedded builders, and driving adoption through OneDigital’s internal support functions (L&D, Change Management, Communications, Marketing, and the Project Management Office). They are accountable for AI outcomes within the practice. They are not accountable for building enterprise AI infrastructure, authoring governance policy, or personally executing training, change, or marketing work.

AI is a new and fluid space, and OneDigital’s approach to AI development within the practices will evolve as tools mature, use cases emerge, and the market shifts. This role requires a leader who is energized by that ambiguity — comfortable operating without a fixed playbook, adjusting strategy as the landscape changes, and partnering with the AI Product Team to shape an approach that will itself continue to change over time.

Essential Duties and Responsibilities:

The AI Innovation Leader is directly accountable for the following — the work does not happen without them:

• Practice AI Roadmap. Develop and maintain a rolling AI roadmap specific to the practice, aligned to enterprise AI strategy and practice growth priorities.
• Use Case Identification and Prioritization. Identify, evaluate, and sequence AI use cases with the highest business and client impact for the practice (e.g., benefits benchmarking and plan design analytics for EB; submission intake and placement workflow for P&C; compliance research and policy review for HR Consulting).
• Business Case Development. Translate AI opportunities into clear business cases for the National Practice Leader, practice leadership, and clients.
• Leadership of Practice-Embedded Builders. Provide day-to-day direction, priority-setting, and performance oversight to AI builders within the practice, with technical architecture and oversight from the AI Product Team.
• Adoption and Outcomes. Own practice-level adoption, active usage, and business impact — ensuring AI tools are integrated into core workflows and generating measurable value.
• Field Engagement and Feedback Loop. Serve as the visible face of AI within the practice — communicating new tools and capabilities in terms that resonate with consultants, energizing the field around practical value, and surfacing friction, ideas, and unmet needs back to the AI Product Team to refine tools, approaches, and roadmap.
• NPL ↔ AI Product Team Integration. Serve as the single point of integration between the National Practice Leader and the AI Product Team — surfacing practice needs, aligning on build-vs.-buy decisions, and ensuring the practice’s voice is represented in enterprise AI planning.
• Practice AI Narrative. Define the external AI story for the practice — shaping client-facing positioning, thought leadership, and business development messaging, in partnership with Marketing and Business Development.

What This Role Partners With

The AI Innovation Leader does not personally execute in the following areas but shares accountability by defining requirements, providing SME input, and driving the practice’s priorities through partner teams:

• AI Product Team — tool selection and procurement, technical architecture, security, data/IT integration, centralized builds, and governance application.
• Learning & Development — role-specific AI training curricula and practice-wide enablement programs.
• Change Management — stakeholder analysis, adoption planning, and transition support.
• Internal Communications — staff messaging, leadership alignment, and change narratives.
• Marketing — external thought leadership, case studies, and client-facing AI content.
• Project Management Office — pilot execution, rollout coordination, and timeline discipline.
• Peer AI Innovation Leaders — cross-practice learning and reusable solutions across Employee Benefits, P&C, and HR Consulting.

What This Role Informs and Enables

The AI Innovation Leader provides expertise and direction but is not the policy or decision owner in these areas:

• Enterprise AI Governance. Represents the practice on governance matters and applies enterprise policy within the practice; does not author enterprise policy.
• Enterprise Tool Selection. Contributes practice requirements and use cases; final architecture and procurement decisions sit with the AI Product Team.
• Risk and Compliance Frameworks. Ensures practice-level adherence to enterprise AI risk standards; does not own the framework itself.

Measurement Areas

The AI Innovation Leader will be accountable for leading or delivering against the following areas. Specific targets, baselines, and timelines will be established collaboratively with the National Practice Leader and AI Product Team following the first 90 days in role:

• Practice AI roadmap delivery and milestone progress
• Adoption and active usage of AI tools across the practice
• Workforce AI literacy and role-based enablement completion
• Productivity or quality improvement in priority workflows
• Use case pipeline health (active pilots, production deployments)
• AI contribution to business development and client pursuits
• Change health indicators (staff sentiment, engagement)
• Practice-level compliance with enterprise AI governance standards

Core Competencies

• Translation — converts fluently between business language and AI capability in both directions.
• Practice Fluency — deeply understands the practice’s service model, client needs, and economic drivers.
• Influence Without Authority — drives outcomes through matrixed teams and peer partners.
• Execution Discipline — moves use cases from idea to pilot to production with rigor.
• Change Leadership — builds buy-in, manages resistance, sustains adoption.
• Hands-on Technical Fluency — personal experience using and prototyping with current AI tools (e.g., custom GPTs, Copilot agents, low-code automation platforms). Able to mock up proofs of concept, evaluate model outputs critically, and credibly direct technical builders. Working knowledge of LLM capabilities, agentic workflows, and data readiness concepts preferred.
• Field-Facing Communication and Curiosity — communicates AI capabilities in practical, “what’s in it for me” terms that energize consultants; listens actively, asks sharp questions, and consistently brings field insight back to refine tools, training, and roadmap.
• Adaptability — thrives in ambiguity and evolves approach as the AI landscape, tooling, and practice needs change.
• Executive Presence — credible with senior leadership, consultants, and clients.

Qualifications, Skills and Requirements:

• 8+ years of progressive experience in insurance brokerage, benefits consulting, HR advisory, or a closely adjacent professional services domain
• 3+ years in a leadership, strategy, or innovation role
• Demonstrated experience leading technology adoption, digital transformation, or organizational change initiatives
• Hands-on experience using AI tools in a work context — including prompt engineering, evaluating model outputs, and building prototypes with custom GPTs, Copilot agents, or low-code automation platforms (e.g., Power Automate, Zapier)
• Experience operating in a matrixed organization, influencing across practice, product, and corporate functions

Education, Training and Experience:

• Bachelor’s degree required; advanced degree (MBA, MS, or equivalent) preferred
• AI/ML coursework, certifications, or formal training in AI strategy or digital transformation valued but not require

Other:

Reports To

• National Practice Leader (solid line)
• AI Product Team leadership (dotted line)

Direct / Matrix Reports

• Practice-embedded AI builders (with technical oversight from the AI Product Team)
• Key Internal Partners
• AI Product Team
• Peer AI Innovation Leaders (Employee Benefits, P&C, HR Consulting)
• Practice leadership team and regional/office leaders within the practice
• Learning & Development
• Change Management
• Internal Communications
• Marketing
• Project Management Office

Key External Relationships

• AI platform and vendor partners (in coordination with AI Product Team)
• Industry associations relevant to the practice
• Clients, in an advisory and thought leadership capacity

The typical base pay range for this role nationwide is $100,000-$160,000 per year.  

Your base pay is dependent upon your skills, education, qualifications, professional experience, and location. In addition to base pay, some roles are eligible for variable compensation, commission, and/or annual bonus based on your individual performance and/or the company’s performance.  We also offer eligible employees health, wellbeing, retirement, and other financial benefits, paid time off, overtime pay for non-exempt employees, and robust learning and development programs. You will receive reimbursement of job-related expenses per the company policy and may receive employee perks and discounts. 

To learn more, visit: www.onedigital.com/careers  

OneDigital is an equal opportunity employer. Not only as a matter of standard, but to honor and celebrate our differences. We believe that the power of ONE starts with you. We are committed to cultivating and preserving a culture that celebrates diversity, insists on equity and inclusion, and connects us. Ensuring our people feel seen, valued, respected, and supported is fundamental to our core values and business goals.

OneDigital provides equal employment opportunities to all employees and applicants for employment regardless of their: veteran status, uniformed servicemember status, race, color, religion, sex, sexual orientation, gender identity, age (40 and over), pregnancy (including childbirth, lactation and related medical conditions), national origin or ancestry, citizenship or immigration status, physical or mental disability, genetic information (including testing and characteristics) or any other category protected by federal, state or local law (collectively, “protected characteristics”). A copy of the Federal EEO poster is linked here.

Pursuant to local Fair Chance Ordinances, we will consider qualified applications with arrest or conviction records for employment. For applicable candidates, the following ordinances are linked here to inform you of your rights as an applicant:

City and County of San Francsico

City of Los Angeles

County of Los Angeles

Employment decisions shall comply with all other applicable federal, state and city/county laws prohibiting discrimination in employment. OneDigital complies with all criminal history inquiry [or ‘ban the box’] laws in California, Connecticut, Colorado, Hawaii, Illinois, Maine, Maryland, Massachusetts, Minnesota, New Jersey, New Mexico, Oregon, Rhode Island, Vermont and Washington.

In short, we believe in hiring the most qualified applicant for the position, regardless of background.

If you have questions about our hiring policies and practices, we would be happy to discuss upon receiving your application. We hope to welcome you to OneDigital and look forward to hearing from you.

OneDigital understands the immense responsibility and opportunities provided by Artificial Intelligence. We utilize advanced Artificial Intelligence [AI] technologies to enhance our recruitment process. This includes using AI to filter candidates based on their qualifications and to rediscover potential candidates from our existing applicant pool. Our AI systems help us efficiently identify the best fit for our open positions, ensuring a streamlined and effective hiring experience. However, AI does not replace the humans in our process. If you have concerns about our use of AI, you may opt out where laws allow.

Thank you for your interest in joining the OneDigital team!