Managing Director, Head of Rollover Solutions (Remote)

Join Us!
Take the next step in your journey at Inspira Financial. You will help businesses and individuals thrive today, tomorrow, and into retirement. Become part of a company that is people centric and client obsessed in every interaction; a community of forward-thinking individuals focused on driving results to deliver our mission with an unwavering commitment to integrity. Join us as we strengthen and simplify the health and wealth journey -- relentlessly pursuing better outcomes for all. We believe in finding the best talent! While some roles are based at one of our office locations, remote roles can sit in any of the following states: AL, AZ, FL, GA, IA, IL, IN, MI, MN, MO, NC, NE, PA, SC, TN, TX, UT, VA and WV. Remote status and role locations are subject to change. Relocation is not provided.
Employees within a 90-minute radius of our Oak Brook, IL headquarters are required to adhere to the company in-office work guidelines of 4 days per month minimum from 10 am to 2 pm (1 of the 4 days must be a Monday or Friday).
This requirement does not apply to support specialist positions.
Don't meet every single requirement? Here at Inspira Financial, we believe there is no "perfect" candidate and want to encourage applying even if all the requirements listed aren't met. Our goal is to build an authentic workplace by valuing diversity in our candidates. We work to ensure that our team reflects the diversity of the businesses and clients we serve. We are always looking to expand our growing team with dynamic and enthusiastic individuals. If you enjoy a collaborative, fun environment that champions career development, Inspira Financial is the place for you! We look forward to receiving your application! Check out this Inspira Financial video to learn more about our company!
Inspira Financial provides health, wealth, retirement, and benefits solutions that strengthen and simplify the health and wealth journey. With more than 7 million clients, representing over $62 billion in assets, Inspira works with thousands of employers, plan sponsors, recordkeepers, TPAs, and other institutional partners -- helping the people they care about plan, save, and invest for a brighter future. Inspira relentlessly pursues better outcomes for all with our automatic rollover services, health savings accounts, emergency savings funds, custody services, and more. Learn more at inspirafinancial.com .
We have been recognized for our remarkable growth on lists such as Crain's Fast 50 and Inc. 5000, and for our outstanding workplace culture and benefits with Built In's 2025 Best Places to Work and Gallagher's 2022 Best-In-Class Employer awards.
Job Summary & Responsibilities
The Head of Rollover Solutions is responsible for the overall growth and success of a business unit serving some of the largest employers and retirement plan recordkeepers in the country. This individual will establish strategy and lead a client-facing organization of 20+ individuals to deliver a high level of client growth, satisfaction and retention. The Head of Rollover Solutions will report directly to the EVP Retirement & Wealth, who is responsible for growing the Retirement & Wealth division at Inspira Financial.
The successful candidate will be a strategic, analytical, market-focused and results-driven leader. They will provide leadership and oversight of the National Sales, Strategic Accounts and National Accounts teams while representing the firm effectively to outside parties including clients, strategic partners, industry associations and the media. The Head of Rollover Solutions will work closely with the Head of Marketing and Chief Operating Officer to execute strategy. This individual will ensure the right people, strategic plans and analytics are defined and managed, and that sales and marketing models are in place to profitably grow the Rollover Solutions business. This leader will effectively, efficiently and profitably ensure the seamless support of existing and new business activities.
KEY RESPONSIBILITIES

• Lead the overall Rollover Solutions business, maintaining responsibility for growth, retention, and overall profitability. This includes leading a cross-functional business leader group responsible for overall business unit success.
• Provide leadership of 20+ individuals in the National Sales, Strategic Accounts and National Accounts teams.
• Establish business unit strategy and client engagement (directly and through team oversight), annual planning and budgeting for the business. This will include a review of the current structure and making adjustments as required.
• Engage directly with key clients and strategic partners as the most senior representative of the Rollover Solutions business; effectively negotiate to realize long-term client commitments that support business unit financial goals.
• Redesign and implement standard metrics by salesperson and relationship manager to measure effectiveness in the short-term and long-term.
• Redesign and implement business effectiveness metrics for short-term and long-term sales and profitability goals. These include: team and individual goals, metrics to understand our share of market, win/loss rate, reason for win/loss, and market share, margin.
• Partner with marketing to guide external marketing and PR plans for the business unit
• Redesign high level business metrics and health scorecards for the business and ensure alignment with the scorecards for compensation purposes.
• Design, implement and maintain clear roles and responsibilities between sales and relationship management.
• Assess, redesign, and manage sales incentive plans ensuring alignment with overall business and Inspira Financial success metrics.
• Partner with product teams on the product roadmap to build a plan aligned with long-term needs. Improve engagement, partnership plans and strategy for new products between product and sales teams.
• Partner with EVP Retirement & Wealth to further build-out the Rollover Solutions business plan for industry strategy and acquisition targets based on feedback.
• Partner with marketing on brand and exposure strategy and plan, including conferences, with success metrics outlined.

The Head of Rollover Solutions will be a proven executive with significant experience in the financial services industry, ideally within a retirement-oriented business, who has led successful sales teams in fast-moving and innovative environments. He/she must have demonstrated commercial success in sales leadership roles. He/she will have the ability to interact with senior leadership and will be able to lead change and challenge decisions.
The ideal candidate will be an experienced sales leader who is financially astute and comfortable using data to inform decisions. This person will be a skilled communicator who can collaborate and influence key stakeholders to build their business plans and maintain alignment with the EVP Retirement & Wealth and business unit heads. He/she must possess an "above and beyond" mindset on meeting internal and external client requirements. He/she will need to have excellent people leadership skills, be able to develop future leaders and create a high-performing culture.
Preferred Qualifications
IDEAL EXPERIENCE
• 20+ years of sales management experience in the financial services industry w/ previous experience in Rollover Solutions
• Good understanding of technology and how to use it to improve product offerings.
• Experience with Salesforce and CRM tools as well as Microsoft suite tools.
• Strong academic credentials. Undergraduate degree required; MBA preferred.
CRITICAL LEADERSHIP CAPABILITIES
• Commercial Focus
• Brings a track record of managing or contributing to the sales aspects of a retirement business or other financial services organization.
• Acts to beat profitability or revenue goals, seizing opportunities to push the envelope and take on new commercial options.
• Takes specific steps to increase profit, focusing on growth in known areas of profit generation.
• Sets stretch targets on the commercial metrics as the key performance indicators for the team.
• Experience with and the ability to oversee relevant sales functional areas: regional sales leader, inside sales, relationship managers, and sales coordinators
• Ability to identify, develop and install best-in-class sales processes.
• Ability to understand market trends and the impact of regulation, compliance and technology changes to Inspira's Rollover Solutions business.
• Comfortable communicating and collaborating with various individuals at all levels of the business both internally and externally. Client Orientation
• Ability to define a sales strategy with data analytics that is aligned to Inspira's growth strategy.
• Seeks regular customer feedback and distinguishes patterns specific to categories of customers or other segments, validating with regular customer data-gathering.
• Tailors responses to customers based on specific patterns of differences, revises approach for each customer.
ACHIEVEMENT DRIVE
• Ability to build strong teams that are effective and efficient; results oriented.
• Change agent that has led change efforts that has produced meaningful results.
• Strong planning, organizational and analytic skills combined with task and time management skills.
• Operationally savvy and results oriented, but with the ability to think broadly, strategically and flexibly.
• Sets continually higher goals that are ambitious but realistic for self and team, geared to organizational objectives.
• Focuses on new business opportunities that enable business development targets to be exceeded

• Frequent travel (approximately 35%).
• Role may require prolonged periods of sitting and use of standard office equipment.

Compensation & Benefits
$275,000- $315,000 per year