Sr. Director, Head of Enterprise Sales (Remote)

Inspira Financial; Oak Brook (IL); Remote; USD 180,000 - 270,000; Full time

Job summary

Inspira Financial is seeking a Senior Director, Head of Enterprise Sales to lead the enterprise segment for Health & Benefits. You will drive new-business growth, craft go-to-market strategies, and cultivate executive relationships with large employers.

You will manage a team of four Enterprise Sales Executives and coordinate cross-functional efforts to win high-value opportunities. Success will be measured by new-revenue growth, pipeline coverage, win rate, forecast accuracy, and productivity.

Responsibilities

• Own Enterprise New-Business Growth: lead 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 go-to-market strategy for large-employer market.
• Identify high-value market opportunities and resource focus.
• Evaluate market dynamics, buyer needs, competitive positioning, and opportunities.
• Recommend changes to sales strategy, resources, and capabilities to accelerate growth.
• Lead and develop enterprise Sales Executives; set expectations, territories, and performance goals.
• Build relationships with consultant, broker, and distribution partners to grow enterprise pipeline.
• Strengthen executive relationships with prospective large employers and position Inspira strategically.
• Create sales operating discipline: pipeline, forecasting, and CRM usage.
• Collaborate across Marketing, Product, Solutions, Operations, Finance, Legal, and Client Management to support growth.
• Own competitive and market intelligence across benefits solutions; translate into actions.
• Deliver predictable, measurable growth with KPI tracking and executive updates.
• Partner with Product and Marketing to strengthen value propositions and differentiation.

Job description

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.