Sr. Director, Head of Enterprise Sales (Remote)

Join Us!

Take the next step in your journey at Inspira Financial. Guided by our mission to enable better health and greater wealth, we help businesses and individuals thrive today, tomorrow, and into retirement by strengthening and simplifying the health and wealth journey.

Serving more than 7 million clients and representing over $62 billion in assets, Inspira partners with thousands of employers, plan sponsors, recordkeepers, TPAs, and other institutional partners to help the people they support plan, save, and invest for a brighter future. Through solutions including automatic rollover services, health savings accounts, emergency savings, and custody services, Inspira is focused on delivering better outcomes for all. Learn more at inspirafinancial.com.

Our values shape how we show up every day. We Lead with Heart by acting with compassion, empathy, and doing what's right; Cultivate Trust through integrity, transparency, and accountability; Aim Higher by never settling for what's expected and continually raising the standard; and Win Together by collaborating inclusively to achieve the best outcomes.

Our growth and culture haven't gone unnoticed -- we've been recognized on Crain's Fast 50 and Inc. 5000 for remarkable growth, and named to Built In's 2025 Best Places to Work and Gallagher's 2022 Best-In-Class Employer for our workplace culture and benefits.

Don't meet every single requirement? That's okay. We know growth comes from people who are willing to learn and challenge themselves, not just check every box. If you're energized and inspired by meaningful work, continuous development, and being part of a team that turns collective effort into real impact, we want to hear from you. We look forward to receiving your application.

Our office locations are designed to bring people together, foster collaboration, and build meaningful connections. While some roles are based at one of our office locations, remote status and role locations are subject to change, and relocation is not provided.

Job Summary & Responsibilities

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

• 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.
  
  

Preferred Qualifications

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
  
  

Pay Range

$175,800-$225,000 per year

Compensation & Benefits

The compensation for this position will vary depending on factors such as your location, skills and experience. The compensation package may also include incentive and bonus opportunities.

Inspira provides industry-leading benefits including, but not limited to: healthcare, 401K savings plan, company holidays, paid time off, parental leave and an employee assistance program.