Sr. Director, Head of Enterprise Sales (Remote)

Inspira Financial•Oak Brook, IL

29d•Remote

About The Position

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.

Requirements

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
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

Nice To Haves

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

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.