Oliver James · 1 day ago
VP of Sales – Employee Benefits
United States
Full-time
Remote
Director/Executive
$175K/yr - $200K/yr
8+ years expOliver James is a growing TPA operating in the employee benefits and healthcare space, and they are seeking a VP of Sales to lead and scale sales operations across the organization. This role involves defining go-to-market strategy and ensuring measurable, predictable, and scalable sales execution while shaping priorities and enabling teams to convert opportunities into long-term client relationships.
Staffing & Recruiting
No H1B
Responsibilities
Overall sales strategy and execution with a primary focus on broker and consultant channels
Development and expansion of national and regional broker relationships
Definition of broker engagement models, value positioning, and sales cadence
Revenue forecasting, pipeline management, and performance accountability
CRM strategy and adoption, ensuring clean data, visibility, and actionable reporting
Sales analytics, KPI definition, and insight-driven decision making
Alignment with marketing on broker-facing campaigns, events, and enablement
Coaching and leadership of sales and business development resources
Executive-level oversight of sales-to-implementation handoff and deal quality
Qualification
Required
8+ years of progressive sales leadership experience, ideally within employee benefits, healthcare, insurance, or TPA environments
Demonstrated success building and scaling broker-driven revenue channels
Strong understanding of broker economics, decision-making drivers, and competitive dynamics
Proven experience leading CRM-driven sales organizations (Salesforce)
Highly analytical, with the ability to translate data into strategic action
Executive presence with experience partnering closely with Presidents, CEOs, or Boards
Comfortable owning outcomes, not just strategy
Company
Oliver James
At Oliver James, we deliver flexible hiring solutions tailored to your business needs across financial services, professional services, commerce & industry.
501-1000 employees
Funding
Current Stage
Late StageLeadership Team
Alexia Bunker
VP - Client Partnerships
Dominic Reilly
Principal Business Partner
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