Sr. Director, Account Executive (Remote)

Join us at Inspira Financial, where we enable better health and greater wealth by helping businesses and individuals thrive today, tomorrow, and into retirement. Guided by our mission, we strengthen and simplify the health and wealth journey. Our values shape how we show up every day: Leading with Heart through compassion and integrity, Cultivating Trust with transparency and accountability, Aiming Higher by continually raising standards, and Winning Together through inclusive collaboration. We tackle both complex challenges and everyday tasks, turning collective effort into life-changing impact.

We believe in finding the best talent. While some roles are office-based, remote roles can be located in AL, AZ, FL, GA, IA, IL, IN, MI, MN, MO, NC, NE, PA, SC, TN, TX, UT, VA, or WV. Remote status and locations are subject to change, and relocation is not provided. Employees within a 90-minute radius of our Oak Brook, IL headquarters must adhere to in-office guidelines of 4 days per month (10 AM–2 PM, with one day being a Monday or Friday), except for support specialist positions.

At Inspira Financial, we value growth and collaboration. If you're energized by meaningful work and continuous development, we invite you to apply—even if you don’t meet every requirement. We look forward to your application.

About the Role

The Sr. Director, Account Executive will report to the Managing Director, Account Management. This role combines strategic client ownership with people leadership, overseeing a team of Account Executives and Team Leads responsible for managing, retaining, and growing a portfolio of enterprise-level national accounts. As the executive sponsor for key clients, you’ll serve as a trusted strategic advisor to C-suite stakeholders and a regional growth champion. Success is measured by client retention, revenue growth, account expansion, and the development of a high-performing team aligned with Inspira Financial’s mission.

Responsibilities

• Client Relationship Management & Executive Sponsorship
  • Serve as executive sponsor for key enterprise accounts, maintaining senior-level engagement with C-suite, HR, Finance, and Benefits leaders.
  • Build and sustain trusted advisor relationships with clients, benefits consultants, brokers, health plan partners, and third-party vendors.
  • Lead structured quarterly business reviews (QBRs) and annual strategy sessions, presenting performance data, benchmarking insights, and forward-looking roadmaps.
  • Proactively identify client concerns or service gaps and advocate internally for timely resolution.
  • Develop deep familiarity with each client’s industry, HR/benefits landscape, corporate objectives, and workforce demographics to deliver customized solutions.
• Team Leadership & People Development
  • Manage and develop a team of 5–8 direct reports (Account Executives and Team Leads) and their client-facing teams across a defined region.
  • Provide regular feedback, set performance goals, and support professional growth.
  • Lead hiring, onboarding, and training to build a high-performing, client-focused team.
  • Direct workflow, resource allocation, and prioritization across the team.
  • Coach and mentor team members to inspire exceptional client outcomes.
  • Develop team metrics, execution plans, and budgets aligned with regional strategy.
• Regional Growth & Retention Strategy
  • Develop and execute a comprehensive growth and retention strategy for the region, establishing partnerships with health plans, brokers, and affiliated organizations.
  • Champion cross-sell and conversion initiatives, ensuring accountability across the team.
  • Drive account expansion by identifying opportunities to grow Inspira’s product footprint (HSAs, FSAs, HRAs, COBRA, Direct Bill, Commuter Benefits, LSAs).
  • Monitor financial, profitability, and usage targets; prepare and coach team members for QBRs.
  • Lead renewal negotiations with a focus on profitability and long-term value.
  • Maintain working knowledge of client base, key contacts, and pricing for renewals.
• Strategic Consulting & Advisory
  • Engage enterprise clients in consultative dialogue about benefits strategy, CDH program performance, healthcare cost management, and employee financial wellness.
  • Provide data-driven recommendations on CDH adoption, contribution strategies, and plan design optimization.
  • Stay current on regulatory developments and industry trends affecting HSAs, FSAs, HRAs, COBRA, and related programs; educate clients on implications.
  • Deliver thought leadership at client, broker, and industry events.
• Internal Collaboration & Operations
  • Partner with Client Success, Implementation, Product, Compliance, and Marketing teams to ensure seamless service delivery.
  • Lead and coordinate responses to RFPs and renewal questionnaires.
  • Maintain accurate records in Salesforce CRM.
  • Provide feedback to product and business development teams on client needs and market trends.
  • Participate in new business development activities (presentations, on-site visits, capability demonstrations).
  • Work cross-functionally to deliver on strategic initiatives.

Requirements

• Education & Experience
  • 15+ years in consumer-directed benefits, account management, or strategic enterprise sales within insurance, financial services, or employee benefits.
  • 10+ years leading account management or enterprise sales teams, with demonstrated success scaling high-performing organizations.
  • 3+ years of consultative selling experience with complex, multi-stakeholder enterprise accounts.
  • Deep familiarity with health insurance, CDH, and benefit account types (HSA, FSA, HRA, COBRA, commuter programs).
  • Proven ability to build executive-level relationships and navigate organizational complexity.
  • Strong negotiation, communication, and presentation skills for diverse audiences.
  • Bachelor’s degree in Business, Healthcare Administration, Finance, Marketing, or equivalent experience.
  • Proficiency with Salesforce CRM and Microsoft Office Suite (PowerPoint, Excel, Word).
  • Ability to travel 25–50% for client meetings, QBRs, broker events, and conferences.
• Preferred Qualifications
  • Experience managing accounts with 5,000+ employees or $50M+ in plan assets.
  • Experience with national brokers/consultants (e.g., Mercer, Aon, WTW, Gallagher) or health plan partners.
  • Knowledge of benefits administration platforms, data analytics, and reporting tools.
  • CEBS, CBP, or other benefits-related certifications.
• Skills & Abilities
  • Ability to lead in complex, high-stakes situations with competing priorities.
  • Strong delegation skills with realistic expectations on timelines and quality.
  • Excellent analytical skills and a proactive, solutions-oriented mindset.
  • Strong interpersonal and collaboration skills; adept at building trust across stakeholders.
  • Experience presenting complex data and compelling business stories.
  • Organizational discipline to meet deadlines and deliver results.
  • Affinity for accuracy, efficiency, and continuous improvement.
  • Aptitude for prioritizing multiple initiatives in a fast-evolving industry.
• Other Requirements
  • Typical schedule: Monday–Friday, 8 AM–5 PM CT; occasional evening/weekend work during peak periods.
  • Employees within a 90-minute radius of Oak Brook, IL must adhere to in-office guidelines (4 days/month, 10 AM–2 PM, including one Monday or Friday).
  • Frequent travel (25–50%).
  • Ability to provide personal transportation for training and client meetings.
  • Prolonged sitting and standard office equipment use; occasional lifting up to 25 pounds.

Pay

$160,000–$195,000 per year.

Benefits

• Industry-leading healthcare benefits.
• 401K savings plan.
• Company holidays and paid time off.
• Parental leave.
• Employee assistance program.
• Incentive and bonus opportunities.