Sr. Director, Head of Enterprise Sales (Remote) at Inspira Financial

United States

<p>The Senior Director, Head of Enterprise Sales reports to the Managing Director, Head of Market &amp; Enterprise Sales and leads Inspira’s enterprise segment for Health &amp; 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.</p> <p> </p> <p><strong>Duties &amp; Responsibilities:</strong></p> <p>1. Own Enterprise New-Business Growth</p> <p>• Lead and deliver the enterprise new-sales growth strategy for large employers</p> <p>• Own achievement of annual new-business revenue, sales, and growth targets</p> <p>• Establish clear priorities for target markets, employer segments, solutions, and opportunities</p> <p>• Translate company growth objectives into an actionable enterprise sales plan</p> <p> </p> <p>2. Develop and Execute the Enterprise Sales Strategy</p> <p>• Build a comprehensive go-to-market strategy for the large-employer market</p> <p>• Identify the highest-value market opportunities and where the organization should focus resources</p> <p>• Continuously evaluate market dynamics, buyer needs, competitive positioning, and emerging opportunities</p> <p>• Recommend changes to sales strategy, coverage, resources, and capabilities required to accelerate growth</p> <p> </p> <p>3. Lead and Develop a High-Performing Enterprise Sales Team</p> <p>• Lead, coach, develop, and performance-manage enterprise Sales Executives</p> <p>• Establish clear individual expectations, territories, account strategies, and performance goals</p> <p>• Create a strong culture of accountability, urgency, collaboration, and consistent execution</p> <p>• Attract, develop, and retain top enterprise sales talent and build appropriate succession plans</p> <p> </p> <p>4. Drive Pipeline Development and Sales Execution</p> <p>• Establish expectations for pipeline creation, qualification, progression, and conversion</p> <p>• Ensure sufficient pipeline coverage to consistently achieve new-sales objectives</p> <p>• Conduct disciplined pipeline and opportunity reviews focused on actions, barriers, next steps, and probability of close</p> <p>• Personally engage in strategic and complex opportunities where executive involvement can improve the likelihood of success</p> <p> </p> <p>5. Build and Expand Consultant, Broker, and Distribution Relationships</p> <p>• Collaborate with broker consultant relations to execute a deliberate strategy for building relationships with key benefits consultants, brokers, and other distribution partners</p> <p>influencing large-employer purchasing decisions</p> <p>• Increase Inspira’s visibility, credibility, and consideration within the consultant and broker community</p> <p>• Identify and develop new distribution opportunities that create scalable sources of enterprise pipeline</p> <p>• Hold the sales team accountable for building meaningful relationships across priority consulting firms and broker organizations</p> <p> </p> <p>6. Strengthen Strategic Employer Relationships</p> <p>• Build executive-level relationships with prospective large employers and key decision-makers</p> <p>• Position Inspira as a strategic partner rather than simply a product or service provider</p> <p>• Understand employer business objectives, benefits strategies, and financial needs and translate those insights into compelling solutions</p> <p>• Serve as an executive representative of Inspira in important prospect meetings, finalist presentations, and industry events</p> <p> </p> <p>7. Create Strong Sales Operating Discipline</p> <p>• Establish a consistent enterprise sales methodology, cadence, and operating rhythm</p> <p>• Maintain high standards for CRM utilization, opportunity management, account planning, forecasting, and sales activity</p> <p>• Ensure accurate and transparent forecasting of enterprise new business</p> <p>• Use data and leading indicators to identify performance gaps early and take corrective action</p> <p> </p> <p>8. Partner Across the Organization to Win</p> <p>• Collaborate closely with Marketing, Product, Solutions, Operations, Client Management, Finance, and other functions to support enterprise growth</p> <p>• Bring market, prospect, consultant, and competitive intelligence back into the organization</p> <p>• Partner with Product and Marketing to strengthen enterprise value propositions, sales messaging, and competitive differentiation</p> <p> </p> <p>9. Own Competitive and Market Intelligence</p> <p>• Maintain a strong understanding of the competitive landscape across HSA, FSA, HRA, COBRA, and related benefits solutions</p> <p>• Identify changing employer expectations, competitive threats, pricing dynamics, and emerging market opportunities</p> <p>• Translate market intelligence into specific actions for the enterprise sales organization</p> <p> </p> <p>10. Deliver Predictable, Measurable Growth</p> <p>• Establish and monitor KPIs including new revenue, pipeline generation, pipeline coverage, win rate, sales cycle, forecast accuracy, consultant-sourced opportunities, and salesperson productivity</p> <p>• Regularly communicate performance, risks, opportunities, and recommended actions to executive leadership</p> <p>• Take ownership for results—not simply sales activity—and make changes to strategy, talent, coverage, or execution when performance is below expectations</p> <p>• Other duties as assigned.</p> <p> </p> <p> </p><div>Qualifications</div><p><strong>Education &amp; Experience:</strong></p> <p>Minimum required:</p> <p>• 12+ years of progressive sales experience in health insurance, managed care, employee benefits, or consumer directed health, with significant responsibility for new business acquisition</p> <p>• 4+ years leading and developing a sales team, including hiring and performance management</p> <p>• Demonstrated track record closing large, complex employer group business through consultant-led RFP and formal procurement processes</p> <p>• Demonstrated experience carrying enterprise pursuits through internal structuring across product, operations, finance, and legal</p> <p>• Bachelor’s degree in Health Care Management, Business Administration, Marketing, or a related field, or an equivalent combination of education, experience, and training, required</p> <p>Additional preferred:</p> <p>• Experience selling to jumbo or national accounts, including multi-site and multi-state employer groups, preferred</p> <p>• Experience with consumer directed health products (HSA/FSA/HRA/COBRA) and how they are evaluated in enterprise benefits procurement preferred</p> <p>• Established relationships with national benefits consulting firms preferred</p> <p> </p> <p>Skills &amp; Abilities:</p> <p>• A player-coach - credible carrying the largest pursuits personally while genuinely developing sellers rather than closing around them</p> <p>• Expertise in consultative and competitive selling to sophisticated, multi-stakeholder enterprise buying committees, with the judgment to sustain pipeline rigor across long cycles</p> <p>• Executive presence with polished written and verbal communication, and credibility in the boardroom and with senior consultants</p> <p>• Strong commercial and analytical capability, including deal economics, pricing structure, and profitability assessment</p> <p>• Deep understanding of the health insurance, managed care, and health and benefits landscape</p> <p>• Fluency with Salesforce, sales analytics, and AI-powered productivity tools</p> <p> </p> <p>Other Requirements:</p> <p>• Typical schedule is Monday–Friday, with flexibility to work evenings or weekends as needed to support broker leadership engagements and industry events</p> <p>• Travel required (25-40%) for broker and consulting firm leadership visits, executive briefings, and industry events</p> <p>• Ability to provide personal transportation from time to time</p> <p>• Prolonged periods of sitting and operating standard office equipment; occasionally lifts up to 25 pounds</p>