VP, Head of Enterprise Sales (Remote)

About the role

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.

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 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.
• 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.
• 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.
• 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.
• 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.
• 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.
• 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.
• 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.
• 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.

Qualifications

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.

Additional Preferred

• Experience selling to jumbo or national accounts, including multi-site and multi-state employer groups.
• Experience with consumer directed health products (HSA/FSA/HRA/COBRA) and how they are evaluated in enterprise benefits procurement.
• Established relationships with national benefits consulting firms.

Skills

• 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