Enterprise Sales Director: Health & Benefits Growth

Inspira Financial Trust, LLC; Oak Brook (IL); Remote; USD 190,000 - 240,000; Full time

Job summary

Inspira Financial Trust, LLC in Oak Brook, IL seeks a Senior Director, Head of Enterprise Sales to lead the enterprise Health & Benefits segment.

You will set GTM strategy, drive new-business revenue, and lead a four-person Enterprise Sales team, cultivating executive-level relationships with large employers and coordinating across Marketing, Product, Solutions, Operations, Finance, Legal, and Client Management.

Responsibilities

• 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
• Develop and Execute the Enterprise Sales Strategy
• Build a go-to-market strategy for the large-employer market
• Identify high-value opportunities and resource focus
• Evaluate market dynamics, buyer needs, and competitive positioning
• Recommend changes to sales strategy and capabilities to accelerate growth
• Lead and Develop a High-Performing Enterprise Sales Team
• Lead, coach, and performance-manage enterprise Sales Executives
• Set clear expectations, territories, and performance goals
• Foster a culture of accountability, urgency, collaboration, and execution
• Attract, develop, and retain top enterprise sales talent with succession planning
• Drive Pipeline Development and Sales Execution
• Para-meter pipeline creation, qualification, progression, and conversion
• Maintain pipeline coverage to achieve new-sales objectives
• Conduct disciplined pipeline reviews and focus on next steps
• Engage in strategic opportunities with executive involvement
• Build and Expand Consultant, Broker, and Distribution Relationships
• Collaborate with broker relations to build relationships with consultants and brokers
• Increase Inspira's visibility and credibility within the consultant community
• Develop new distribution opportunities for scalable enterprise pipeline
• Hold the sales team accountable for relationships with consulting firms and brokers
• Strengthen Strategic Employer Relationships
• Build executive-level relationships with large employers
• Position Inspira as a strategic partner, not just a provider
• Understand employer objectives and translate into compelling solutions
• Represent Inspira in finalist meetings and industry events
• Create Strong Sales Operating Discipline
• Establish a consistent enterprise sales methodology, cadence, and rhythm
• Maintain CRM, opportunity management, planning, forecasting, and activity standards
• Ensure accurate forecasting of enterprise new business
• Use data to identify gaps and take corrective action
• Partner Across the Organization to Win
• Collaborate with Marketing, Product, Solutions, Operations, Client Management, Finance
• Bring market and competitive intelligence into the organization
• Strengthen value propositions and sales messaging with Product and Marketing
• Own Competitive and Market Intelligence
• Understand competitive landscape across benefits solutions
• Identify changing expectations, threats, pricing dynamics, and opportunities
• Translate intelligence into actions for the sales organization
• Deliver Predictable, Measurable Growth
• Establish and monitor KPIs: revenue, pipeline, win rate, forecast accuracy
• Communicate performance and risks to executive leadership
• Take ownership for results and adjust strategy as needed

Job description

Inspira Financial Trust, LLC in Oak Brook, IL seeks a Senior Director, Head of Enterprise Sales to lead the enterprise Health & Benefits segment.

You will set GTM strategy, drive new-business revenue, and lead a four-person Enterprise Sales team, cultivating executive-level relationships with large employers and coordinating across Marketing, Product, Solutions, Operations, Finance, Legal, and Client Management.