×
Register Here to Apply for Jobs or Post Jobs. X

Sr. Director, Head of Enterprise Sales; Remote

Remote / Online - Candidates ideally in
Oak Brook, DuPage County, Illinois, 60523, USA
Listing for: Inspira Financial
Remote/Work from Home position
Listed on 2026-10-15
Job specializations:
  • Sales
    Director of Sales
  • Management
Salary/Wage Range or Industry Benchmark: 180000 - 225000 USD Yearly USD 180000.00 225000.00 YEAR
Job Description & How to Apply Below
Position: 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

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…
To View & Apply for jobs on this site that accept applications from your location or country, tap the button below to make a Search.
(If this job is in fact in your jurisdiction, then you may be using a Proxy or VPN to access this site, and to progress further, you should change your connectivity to another mobile device or PC).
 
 
 
Search for further Jobs Here:
(Try combinations for better Results! Or enter less keywords for broader Results)
Location
Increase/decrease your Search Radius (miles)
0
200
Filters
Education Level
Experience Level (years)
Posted in last:
Salary