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Sr. Director, Account Executive (Remote

Remote / Online - Candidates ideally in
Oak Brook, DuPage County, Illinois, 60523, USA
Listing for: Inspira Financial
Remote/Work from Home position
Listed on 2026-08-13
Job specializations:
  • Management
    Client Relationship Management, Account Manager
Job Description & How to Apply Below
Position: Sr. Director, Account Executive (Remote)

Sr. Director, Account Executive

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.

This leader serves as the executive sponsor for key clients, a trusted strategic advisor to C-suite stakeholders, and a regional growth champion. Success is defined by client retention, revenue growth, account expansion, and the development of a high-performing team aligned to Inspira Financial's mission of helping participants achieve their healthcare financial wellness goals.

Client Relationship Management & Executive Sponsorship
  • Serve as executive sponsor for key enterprise accounts, maintaining senior-level engagement across client organizations including C-suite, HR, Finance, and Benefits leaders.
  • Build and sustain trusted advisor relationships with client contacts, benefits consultants, brokers, health plan partner account teams, and third-party vendors to strengthen the overall client ecosystem.
  • Lead structured quarterly business reviews (QBRs) and annual strategy sessions, presenting program performance data, benchmarking insights, and forward-looking roadmaps.
  • Proactively identify client concerns or service gaps and serve as the client's internal advocate within Inspira Financial to ensure timely resolution and a best-in-class experience.
  • Develop deep familiarity with each client's industry, HR and benefits landscape, corporate objectives, and workforce demographics to deliver highly relevant and customized solutions.
Team Leadership & People Development
  • Manage and develop a team of 5–8 direct reports (Account Executives and Team Leads), along with their respective client-facing teams across a defined region.
  • Provide regular, timely feedback; set meaningful performance goals; and actively support the professional growth of each team member.
  • Lead hiring, onboarding, and training processes to build a high-performing, client-focused organization.
  • Direct daily workflow, resource allocation, and prioritization across the team and department.
  • Coach, mentor, and challenge team members in ways that inspire them to reach their full potential and deliver exceptional client outcomes.
  • Develop team metrics, execution plans, and budgets aligned to the broader regional strategy established by the Managing Director.
Regional Growth & Retention Strategy
  • Develop and execute a comprehensive growth and retention strategy for the region, establishing a strong foothold with key health plan partners, brokers, and affiliated organizations.
  • Champion all cross-sell and conversion initiatives across the region, ensuring proper communication flow and accountability throughout the team.
  • Drive account expansion by identifying opportunities to grow Inspira Financial's product footprint within each client — including HSAs, FSAs, HRAs, COBRA, Direct Bill, Commuter Benefits, and Lifestyle Spending Accounts (LSAs).
  • Monitor financial, profitability, and usage targets across the portfolio; prepare and coach team members to conduct QBRs that thoroughly explain metrics and analytics for each account.
  • Lead renewal negotiations with a focus on maintaining profitability while demonstrating the long-term value of Inspira Financial's platform and service model.
  • Maintain a high working knowledge of the client base, key contacts, and pricing for renewals to ensure effective execution of retention strategy and revenue protection.
Strategic Consulting & Advisory
  • Engage enterprise clients in consultative dialogue around their overall benefits strategy, CDH program performance, healthcare cost management goals, and employee financial wellness objectives.
  • Provide data-driven recommendations on CDH account adoption best practices, employer and member contribution strategies, and plan design optimization.
  • Stay current on regulatory developments, IRS guidance, and industry trends affecting HSAs, FSAs, HRAs, COBRA, and related programs; proactively educate clients on organizational implications.
  • Deliver thought…
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