Sr. Director, Head of Enterprise Sales (Remote)

Inspira Financial Trust, LLC; Oak Brook (IL); A distancia; USD 190.000 - 240.000; Jornada completa

Descripción de la vacante

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.

Responsabilidades

• 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

Descripción del empleo

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.

Duties & Responsibilities:

• 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, Finance, and other functions to support enterprise growth
  • Bring market, prospect, consultant, and competitive intelligence back into the organization
  • Partner with Product and Marketing to strengthen enterprise value propositions, sales messaging, and competitive differentiation
• 9. Own Competitive and Market Intelligence
  • Maintain a strong understanding of the competitive landscape across HSA, FSA, HRA, COBRA, and related benefits solutions
  • Identify changing employer expectations, competitive threats, pricing dynamics, and emerging market opportunities
  • Translate market intelligence into specific actions for the enterprise sales organization
• 10. Deliver Predictable, Measurable Growth
  • Establish and monitor KPIs including new revenue, pipeline generation, pipeline coverage, win rate, sales cycle, forecast accuracy, consultant-sourced opportunities, and salesperson productivity
  • Regularly communicate performance, risks, opportunities, and recommended actions to executive leadership
  • Take ownership for results-not simply sales activity-and make changes to strategy, talent, coverage, or execution when performance is below expectations
  • Other duties as assigned.