Strategic Partnership Sales Director (Remote)

Inspira Financial Trust, LLC in; Oak Brook (IL); Remote; USD 133,000 - 155,000; Full time

Job summary

Inspira Financial is seeking a Strategic Partnership Sales Director to sell into 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 own the full sales motion end to end with an API-first platform.

The ideal candidate has 5–8+ years in enterprise sales, the ability to navigate buying committees, and experience with Salesforce.

Qualifications

• 5–8+ years closing high-ACV, complex B2B deals with multiple stakeholders.
• Experience owning named enterprise accounts.
• 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.

Responsibilities

• Own a focused set of named enterprise accounts: map stakeholders, identify business problems, quantify cost of inaction, and build the account strategy to win.
• Lead with discovery, not decks. Apply a Gap Selling approach to surface and quantify gaps and build urgency.
• Build multi-threaded relationships across product, operations, technical, compliance, and legal stakeholders; align buying committees.
• Run deals end to end across 9+ month cycles: discovery, solution design, business case, procurement, legal review, close.
• Engage in technical integration conversations and CFO-level business case reviews; run 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 pipeline data and forecast with confidence; know what’s real and what’s required to advance.
• Use AI responsibly to accelerate value delivery and build trust internally and with client organizations.

Skills

Executive presence

Communication skills

Gap Selling

Salesforce experience

APIs & demos

Education

Bachelor's Degree in Business or Finance

Tools

Salesforce CRM

APIs

Job description

Strategic Partnership Sales Director (Remote)

#26-1444

Work Location Type

Home Based

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. WeLead with Heartby acting with compassion, empathy, and doing what's right;Cultivate Trustthrough integrity, transparency, and accountability;Aim Higherby never settling for what's expected and continually raising the standard; andWin Togetherby 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.

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 organization s.

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+

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.

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This Company is an Equal Opportunity Employer, and does not discriminate on the basis of race, gender, ethnicity, religion, national origin, age, disability, veteran status, or on any other basis prohibited by law. Information on race, gender and national origin will only be used for statistical and recordkeeping purposes, and will not be used in making any employment decisions. All information provided will be kept separate from your expression of interest. Providing this information is strictly voluntary, and you will not be subjected to any adverse action or treatment if you choose not to provide this information. If you do not choose to answer these questions, we ask that you select "Decline to Identify" for each question. Thank you for your voluntary cooperation.

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