VP Benefits Operations & Strategy

OneDigital•New York, NY

20h•$200,000 - $250,000

About The Position

OneDigital is a people-focused organization at its core, specializing in employee benefits. They assist over 100,000 employers in providing health, pharmacy, long and short-term disability, vision, dental, and other insurance solutions, distinguishing themselves with comprehensive services, technology-based tools, and a dedicated team of advisors. The Vice President, Benefits Operations & Strategy, is a leadership role responsible for driving performance, scalability, and client impact across benefits consulting operations, analytics, and enablement. This position involves integrating advanced financial analysis, data systems, and technology solutions to improve decision-making, streamline workflows, and enhance the readiness of Consultants and Account Managers. The VP will collaborate with regional leadership, carriers, and cross-functional teams to lead strategic initiatives, support innovative solution development, and ensure accurate, insight-driven client deliverables, ultimately aligning business strategy with operational excellence and talent readiness to boost retention, growth, and market competitiveness.

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
10+ years of experience in employee benefits, with demonstrated leadership in team development, operational strategy, or practice building.
Bachelor’s degree, required
Proficient in all Microsoft Office products, required
Intermediate to advanced proficiency in Microsoft Excel, required

Nice To Haves

Business, Finance, Math, Accounting, or related field (for Bachelor's degree), preferred
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

Responsibilities

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.