Strategic Partnership Sales Director (Remote)

Inspira Financial; Oak Brook (IL); On-site; USD 133,000 - 155,000; Full time

Benefits offered by this job

Healthcare

401K savings plan

Company holidays

Paid time off

Parental leave

Employee assistance program

Job summary

Inspira Financial is seeking a Strategic Partnership Sales Director to sell into large, complex organizations within consumer-directed healthcare (HSAs, HRAs, FSAs, LSAs). You will own the full sales motion end to end, managing a short list of high-value accounts with long sales cycles, supported by an API-first platform and a high-growth team.

The ideal candidate has 5–8+ years of enterprise B2B sales, strong executive presence, and experience navigating cross-functional buying committees.

Qualifications

• 5+ years closing high-ACV, complex B2B deals with multiple stakeholders.
• Bachelor's Degree in Business or Finance preferred.
• Experience with CDH benefits (HSA/HRA/FSA) or ERISA is a plus.

Responsibilities

• Own a focused set of named enterprise accounts and build account strategy to win.
• Lead with discovery and quantify the gap between current and desired state.
• Run deals end-to-end with long cycles and multi-stakeholder buy-in.
• Engage in technical integrations and CFO-level business-case reviews.
• Develop and quantify business cases connecting Inspira’s platform to outcomes.

Skills

Enterprise sales

Executive presence

Gap Selling

API integrations

Salesforce CRM

Education

Bachelor's Degree in Business or Finance

Tools

Salesforce

Job description

Join Us!

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 inspirafinancial.com.

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.

Remote status and role locations are subject to change, and relocation is not provided.

Job Summary & Responsibilities

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.

Preferred Qualifications

• 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

Pay Range

$132,700 -$155,000 per year OTE $310k+

Compensation & Benefits

The compensation for this position will vary depending on factors such as your location, skills and experience. The compensation package may also include incentive and bonus opportunities. Inspira provides industry-leading benefits including, but not limited to: healthcare, 401K savings plan, company holidays, paid time off, parental leave and an employee assistance program.