Sr. Director, Account Executive (Remote)

IF
Inspira Financial

Sales & Business Development

Oak Brook, IL, USA

Posted on Aug 8, 2026

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 leadership by representing Inspira Financial at client, broker/consultant, and industry events, webinars, and conferences.

Internal Collaboration & Operations

  • Partner closely with Client Success, Implementation, Product, Compliance, and Marketing teams to ensure seamless delivery of services and solutions for enterprise accounts.
  • Lead and coordinate responses to RFPs and renewal questionnaires, assembling appropriate internal resources, messaging, and competitive positioning.
  • Maintain accurate, up-to-date records of client interactions, pipeline activities, and account plans within Salesforce CRM.
  • Provide structured feedback to product and business development teams on client needs, competitive dynamics, market trends, and emerging opportunities.
  • Participate in new business development activities including finalist presentations, on-site visits, and capability demonstrations.
  • Work cross-functionally to deliver on strategic initiatives and shared company goals.