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. 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. #J-18808-Ljbffr Inspira Financial Trust, LLC