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.

Education & Experience:

Minimum required:

• 12+ years of progressive sales experience in health insurance, managed care, employee benefits, or consumer directed health, with significant responsibility for new business acquisition

• 4+ years leading and developing a sales team, including hiring and performance management

• Demonstrated track record closing large, complex employer group business through consultant-led RFP and formal procurement processes

• Demonstrated experience carrying enterprise pursuits through internal structuring across product, operations, finance, and legal

• Bachelor’s degree in Health Care Management, Business Administration, Marketing, or a related field, or an equivalent combination of education, experience, and training, required

Additional preferred:

• Experience selling to jumbo or national accounts, including multi-site and multi-state employer groups, preferred

• Experience with consumer directed health products (HSA/FSA/HRA/COBRA) and how they are evaluated in enterprise benefits procurement preferred

• Established relationships with national benefits consulting firms preferred

Skills & Abilities:

• A player-coach - credible carrying the largest pursuits personally while genuinely developing sellers rather than closing around them

• Expertise in consultative and competitive selling to sophisticated, multi-stakeholder enterprise buying committees, with the judgment to sustain pipeline rigor across long cycles

• Executive presence with polished written and verbal communication, and credibility in the boardroom and with senior consultants

• Strong commercial and analytical capability, including deal economics, pricing structure, and profitability assessment

• Deep understanding of the health insurance, managed care, and health and benefits landscape

• Fluency with Salesforce, sales analytics, and AI-powered productivity tools

Other Requirements:

• Typical schedule is Monday–Friday, with flexibility to work evenings or weekends as needed to support broker leadership engagements and industry events

• Travel required (25-40%) for broker and consulting firm leadership visits, executive briefings, and industry events

• Ability to provide personal transportation from time to time

• Prolonged periods of sitting and operating standard office equipment; occasionally lifts up to 25 pounds