Remote Director Store Design Jobs in Chicago, IL

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.

Education & Experience:

Required

• 15+ years of experience in consumer-directed benefits, account management, or strategic enterprise sales within the insurance, financial services, or employee benefits industry.
• 10+ years of experience leading account management or enterprise sales teams, with demonstrated success building and scaling high-performing organizations.
• 3+ years of consultative and strategic selling experience with a proven track record of retaining and growing complex, multi-stakeholder enterprise accounts.
• Deep familiarity with health insurance, consumer-directed healthcare (CDH), and benefit account types including HSA, FSA, HRA, COBRA, and commuter programs.
• Proven ability to build executive-level relationships and navigate organizational complexity across HR, Finance, Benefits, and C-suite stakeholders.
• Strong negotiation, communication, and presentation skills with the ability to tailor messaging for executive, operational, and technical audiences.
• Bachelor's degree in Business, Healthcare Administration, Finance, Marketing, or equivalent combination of education and experience.
• Proficiency with Salesforce CRM and Microsoft Office Suite (PowerPoint, Excel, Word).
• Ability to travel 25-50% for client meetings, QBRs, broker events, and industry conferences.

Preferred

• Experience managing accounts with 5,000+ employees or $50M+ in plan assets.
• Experience working with national brokers and consultants (e.g., Mercer, Aon, WTW, Gallagher) or health plan carrier partners.
• Knowledge of benefits administration platforms, data analytics, and reporting tools.
• CEBS, CBP, or other benefits-related professional certification.

Skills & Abilities:

• Demonstrated ability to perform and lead in complex, high-stakes situations with multiple competing priorities.
• Ability to effectively delegate while maintaining realistic expectations on timelines and quality.
• Excellent analytical skills with a proactive, solutions-oriented mindset.
• Strong interpersonal and collaboration skills; adept at building trust across diverse stakeholders.
• Experience presenting complex data, educational material, and compelling business stories to both clients and internal teams.
• Strong organizational discipline with a drive to meet deadlines and deliver results.
• An affinity for accuracy, efficiency, and continuous improvement.
• An aptitude for prioritization and managing multiple initiatives simultaneously.
• A drive to learn and apply new concepts quickly in a fast-evolving industry.

Other Requirements:

• Typical schedule: Monday-Friday, 8AM-5PM CT; ability to work evening or weekend hours during peak periods.
• Employees within a 90-minute radius of Oak Brook, IL headquarters are required to adhere to Company in-office guidelines of 4 days per month minimum from 10AM-2PM (1 of the 4 days must be a Monday or Friday).
• Frequent travel required (25%-50%).
• Ability to provide personal transportation for training and client meetings.
• Prolonged periods of sitting and operating standard office equipment.
• Occasionally lifts up to 25 pounds.