[Remote] Sr. Director, Head of Enterprise Sales (Remote)

Note: The job is a remote job and is open to candidates in USA. Inspira Financial is hiring a Senior Director, Head of Enterprise Sales to lead new-business growth for its Health & Benefits enterprise segment. The role sets the go-to-market strategy, develops a team of enterprise sales executives, builds consultant and broker relationships, and leads complex employer pursuits and sales operations.

Responsibilities

• 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
• 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, 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
• 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
• 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
• 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
• 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
• 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
• 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
• 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

Skills

• 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
• 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
• 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

Company Overview