Strategic Partnership Sales Director (Remote)

IF
Inspira Financial

Sales & Business Development

Oak Brook, IL, USA

Posted on Sep 16, 2026

Inspira is looking for a Strategic Partnership Sales Director to sell into the heart of complex organizations within consumer-directed healthcare — HSAs, HRAs, FSAs, and LSAs. This is not a volume role. You will carry a short list of high-value, named accounts and be expected to go deep: building real relationships, understanding the business problems beneath the surface, and closing strategic deals where the cycles are long and the outcomes are significant. You will own the full sales motion end to end, supported by a genuinely differentiated, API-first platform, an underserved market, and a team that moves fast.  

 

Inspira is an innovative, growing company disrupting the health spending benefits market. We are seeking team members looking to grow with us. At Inspira, we believe in empowering colleagues to deliver a smarter health benefits platform. We seek professionals who have demonstrated experience using AI responsibly to accelerate delivering value to customers, improving client experience, and solving complex problems more efficiently 

 

Enterprise sales experience of 5–8+ years closing high-ACV, complex B2B deals required, ideally within the consumer-directed health benefits industry. The ideal candidate will have a proven ability to build multi-threaded relationships, navigate complex buying committees, and turn cold strategic accounts into long-term, seven-figure partnerships. 

 

Duties & Responsibilities: 

 

  • Own a focused set of named enterprise accounts: map the stakeholders, identify the business problems beneath the surface, quantify the cost of inaction, and build the account strategy required to win each one. 
  • Lead with discovery, not decks. Apply a Gap Selling approach to surface and quantify the gap between a prospect’s current and desired state and use it to build urgency and move deals. 
  • Build multi-threaded relationships and champions across product, operations, technical, compliance, and legal stakeholders, and create alignment across buying committees that don’t always agree. 
  • Run deals end to end across 9+ month cycles: discovery, solution design, business case development, procurement, legal review, and close. 
  • Engage credibly in both technical integration conversations and CFO-level business case reviews, running your own product demos on an API-first platform. 
  • Develop and quantify business cases that connect Inspira’s platform to measurable outcomes for each prospect. 
  • Maintain clean, accurate pipeline data and forecast with confidence — knowing which opportunities are real and what is required to advance each one. 
  • Use AI responsibly to accelerate value delivery and solve complex problems more efficiently, and build strong relationships and trust both internally and within client organizations.