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Open nowFirst seen 5 days ago

Strategic Partnership Sales Director (Remote)

Inspira Financial36 open roles

Where
Oak Brook, IL, USA
Work mode
Remote
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Your applicationOpen nowStrategic Partnership Sales Director (Remote)Inspira Financial · Oak Brook, IL, USA

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The clock on this job

Early applications get read.

12.3% of postings close within 7 days. Measured by our own scanner across the market. Inspira Financial postings stay open a median of 1 days.

Share of postings closed within
  1. 2.1%1 day
  2. 4.5%3 days
  3. 12.3%7 days
  4. 19.3%14 days
  5. 35.6%30 days
  6. 58.1%60 days
This job: first seen 5 days ago

Inspira Financial median: 1 days open

The posting

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.
  • Experience & Skills: 5–8+ years closing high-ACV, complex B2B deals with multiple stakeholders; experience owning named enterprise accounts Strong executive presence and communication/presentation skills Disciplined Gap Selling practitioner who leads with the problem, builds urgency from the inside out, and qualifies out of deals that aren’t real Benefits or CDH experience — HSA/HRA/FSA administration, TPAs, or benefits platforms; familiarity with ERISA, IRS rules for CDH accounts, or ACA compliance is a plus Technically fluent: able to understand integrations, run your own demos, and engage credibly with engineering and product stakeholders on an API-first platform Self-sufficient and comfortable operating with autonomy and accountability, without a large support organization to lean on Strong collaboration skills with a bias toward action and ownership A drive to learn and apply new concepts quickly Experience with Salesforce CRM preferred Education & Experience: 5+ years of experience in consumer benefits sales industry. Bachelor's Degree in Business or Finance preferred.

Other Requirements:

  • Infrequent travel (50%) Ability to provide personal transportation from time to time
  • Occasionally lifts up to 25 pounds
  • Prolonged periods of sitting at a desk and working on a computer
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