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.

• 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

• 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

• 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

• 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

• 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

• 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,…