VP Benefits Operations & Strategy

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 Vice President, Benefits Operations & Strategy, provides thoughtful leadership across benefits consulting operations, analytics, and enablement to drive performance, scalability, and client impact. This role integrates advanced financial analysis, data systems, and technology-driven solutions to enhance decision-making, streamline workflows, and strengthen Consultant and Account Manager readiness. Partnering closely with regional leadership, carriers, and cross‑functional teams, the VP leads strategic initiatives, supports innovative solution development, and ensures accurate, insight-driven client deliverables. The position plays a critical role in aligning business strategy, operational excellence, and talent readiness to accelerate retention, growth, and market competitiveness.

Essential Duties and Responsibilities (include but are not limited to):

• Designs and delivers targeted training and fast-track onboarding programs for Consultants and Account Managers, building financial acumen, benefits knowledge, and client readiness to strengthen team performance and accelerate retention outcomes.
• Drives the ideation and implementation of productivity-enhancing tools and processes, identifying opportunities to streamline workflows, automate analysis, and improve decision-making through advanced technology and AI-enabled solutions.
• Leads and accelerates special projects and strategic operational initiatives, serving as a cross-functional subject matter expert who connects financial insight, system integration, and business strategy to move priorities forward.
• Partners with regional leadership on the development and rollout of small-group solution offerings, including active participation in pilot programs, feedback loops, and iterative product refinement.
• Partners with market leadership to assess, develop, and scale the NY client service team, contributing to hiring decisions, onboarding programs, and career development pathways for AMs and BCs.
• Collaborates with market and regional leadership to design and implement the NY service delivery model for the core segment, including team structures, role clarity, capacity benchmarks, and operational standards that support profitable growth.
• Contributes to the identification, piloting, and adoption of AI-enabled solutions across the NY market, partnering with regional and national leadership to scale tools that improve consultant efficiency and client outcomes. 
• Supports the deployment and adoption of EOS (Entrepreneurial Operating System) across the market, contributing to metric development, scorecard accountability, and cross-functional alignment.
• Supports implementation and ongoing optimization of data systems, ensuring data integrity, reporting accuracy, and alignment with evolving business processes and team needs.
• Applies financial modeling, forecasting, and scenario analysis expertise to support strategic planning, internal initiatives, and the development of client solutions — bringing analytical rigor to key business decisions.
• Drafts and reviews financial exhibits, cost projections, and benefit plan analyses for quarterly and annual client meetings, ensuring accuracy and strategic relevance.
• Produces and reviews client utilization reports and monthly reporting deliverables, leveraging carrier reporting tools to surface actionable insights and plan design opportunities.
• Analyzes utilization patterns and industry benchmarks to identify plan design improvements and validate client competitiveness in the market.
• Maintains strong carrier partner relationships and ensures market information is accurate, current, and organized within internal systems.
• Provides support and strategic input on carrier negotiation processes, ensuring market competitiveness and alignment with client strategy. 

Qualifications, Skills and Requirements:

• Ability to analyze data and recognize analytical patterns
• Strong verbal and written communication skills
• Presentation skills
• Ability to effectively handle multiple and changing client priorities and deadlines
• Excellent interpersonal skills
• Ability to thrive in a fast-paced environment

Education, Training and Experience:

• 10+ years of experience in employee benefits, with demonstrated leadership in team development, operational strategy, or practice building. 
• Bachelor’s degree, required; Business, Finance, Math, Accounting, or related field, preferred
• Proficient in all Microsoft Office products, required
• Intermediate to advanced proficiency in Microsoft Excel, required
• Experience in the healthcare industry working for a group insurance carrier, broker or consultant, preferred
• Knowledge of group insurance including medical, dental, CDHP, pharmacy, life and disability products, strongly preferred
• Experience with database applications, a plus

The typical base pay range for this role nationwide is $200,000 to $250,000 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!