Sr. Director, Head of Enterprise Sales; Remote

The Senior Director, Head of Enterprise Sales reports to the Managing Director, Head of Market & Enterprise Sales and leads Inspira's enterprise segment for Health & Benefits - the largest employer group segment. The role owns new-business growth for the enterprise segment: setting the go-to-market strategy, leading and developing a team of four enterprise Sales Executives, and driving the pipeline discipline needed to hit new-business revenue and growth targets.

The Senior Director builds on the consultant, broker, and distribution relationships that create scalable enterprise pipeline, and personally cultivates executive-level relationships with prospective large employers, positioning Inspira as a strategic partner rather than a product or service provider. The role also leads the highest-value pursuits, which run through consultant-led RFP processes over extended cycles and require coordinated work across Marketing, Product, Solutions, Operations, Finance, Legal, and Client Management.

Success is measured against new-business revenue, pipeline coverage and win rate, forecast accuracy, consultant-sourced opportunities, and salesperson productivity.

• 1. Own Enterprise New-Business Growth
  • Lead and deliver the enterprise new-sales growth strategy for large employers
  • Own achievement of annual new-business revenue, sales, and growth targets
  • Establish clear priorities for target markets, employer segments, solutions, and opportunities
  • Translate company growth objectives into an actionable enterprise sales plan
• 2. Develop and Execute the Enterprise Sales Strategy
  • Build a comprehensive go-to-market strategy for the large-employer market
  • Identify the highest-value market opportunities and where the organization should focus resources
  • Continuously evaluate market dynamics, buyer needs, competitive positioning, and emerging opportunities
  • Recommend changes to sales strategy, coverage, resources, and capabilities required to accelerate growth
• 3. Lead and Develop a High-Performing Enterprise Sales Team
  • Lead, coach, develop, and performance-manage enterprise Sales Executives
  • Establish clear individual expectations, territories, account strategies, and performance goals
  • Create a strong culture of accountability, urgency, collaboration, and consistent execution
  • Attract, develop, and retain top enterprise sales talent and build appropriate succession plans
• 4. Drive Pipeline Development and Sales Execution
  • Establish expectations for pipeline creation, qualification, progression, and conversion
  • Ensure sufficient pipeline coverage to consistently achieve new-sales objectives
  • Conduct disciplined pipeline and opportunity reviews focused on actions, barriers, next steps, and probability of close
  • Personally engage in strategic and complex opportunities where executive involvement can improve the likelihood of success
• 5. Build and Expand Consultant, Broker, and Distribution Relationships
  • Collaborate with broker consultant relations to execute a deliberate strategy for building relationships with key benefits consultants, brokers, and other distribution partners influencing large-employer purchasing decisions
  • Increase Inspira's visibility, credibility, and consideration within the consultant and broker community
  • Identify and develop new distribution opportunities that create scalable sources of enterprise pipeline
  • Hold the sales team accountable for building meaningful relationships across priority consulting firms and broker organizations
• 6. Strengthen Strategic Employer Relationships
  • Build executive-level relationships with prospective large employers and key decision-makers
  • Position Inspira as a strategic partner rather than simply a product or service provider
  • Understand employer business objectives, benefits strategies, and financial needs and translate those insights into compelling solutions
  • Serve as an executive representative of Inspira in important prospect meetings, finalist presentations, and industry events
• 7. Create Strong Sales Operating Discipline
  • Establish a consistent enterprise sales methodology, cadence, and operating rhythm
  • Maintain high standards for CRM utilization, opportunity management, account planning, forecasting, and sales activity
  • Ensure accurate and transparent forecasting of enterprise new business
  • Use data and leading indicators to identify performance gaps early and take corrective action
• 8. Partner Across the Organization to Win
  • Collaborate closely with Marketing, Product, Solutions, Operations, Client Management,…