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Sr. Implementation Manager, Health & Benefits (Client Onboarding, Remote)

Inspira Financial
Oak Brook, IL Remote Full Time
POSTED ON 10/15/2026
AVAILABLE BEFORE 11/12/2026
Join Us!

Take the next step in your journey at Inspira Financial. Guided by our mission to enable better health and greater wealth, we help businesses and individuals thrive today, tomorrow, and into retirement by strengthening and simplifying the health and wealth journey.

Serving more than 7 million clients and representing over $62 billion in assets, Inspira partners with thousands of employers, plan sponsors, recordkeepers, TPAs, and other institutional partners to help the people they support plan, save, and invest for a brighter future. Through solutions including automatic rollover services, health savings accounts, emergency savings, and custody services, Inspira is focused on delivering better outcomes for all. Learn more at inspirafinancial.com.

Our values shape how we show up every day. We Lead with Heart by acting with compassion, empathy, and doing what's right; Cultivate Trust through integrity, transparency, and accountability; Aim Higher by never settling for what's expected and continually raising the standard; and Win Together by collaborating inclusively to achieve the best outcomes.

Our growth and culture haven't gone unnoticed -- we've been recognized on Crain's Fast 50 and Inc. 5000 for remarkable growth, and named to Built In's 2025 Best Places to Work and Gallagher's 2022 Best-In-Class Employer for our workplace culture and benefits.

Don't meet every single requirement? That's okay. We know growth comes from people who are willing to learn and challenge themselves, not just check every box. If you're energized and inspired by meaningful work, continuous development, and being part of a team that turns collective effort into real impact, we want to hear from you. We look forward to receiving your application.

Remote status and role locations are subject to change, and relocation is not provided.

Job Summary & Responsibilities

The Sr. Implementation Manager will report to the Sr. Manager, Client Management in the CDB Client Services Department. This role is responsible for coaching, training and mentoring team members, assisting with the development, reviewing, and updating of policies and desktop procedures, and discussing, testing, and implementing new product offerings and new software applications. Through verbal and written communications, the ideal incumbent will develop, strengthen, and maintain a positive relationship with our clients and firm associates. This role is also responsible for providing focused service from pre-sale consultation through initial post-sale client administration fostering strong, long-term partnerships with customers and consulting community. This role will direct all aspects of customer benefit plan installation for new and existing high profile, large, complex customers of PayFlex's products and services. The incumbent will develop and execute an implementation strategy consistent with customer expectations. Ultimately creating, managing and tracking detailed project plans and issue logs outlining required actions, responsible parties and assigned target dates associated with the delivery of the services and projects.

  • Act as the single point-of-contact for benefit plan implementation; mediates and coordinates resolution of all project deliverables and implementation related issues
  • Ensure implementation strategy is administered in accordance with all performance guarantee arrangements
  • Partner with all key stakeholders (i.e., sales/service staff, consultants, plan sponsors, and other internal business units) to proactively identify and address critical implementation issues ensuring customer expectations are consistently satisfied or exceeded
  • Evaluate impact of client-requested exceptions and develops reasonable alternatives to satisfy client’s needs while minimizing impact on systems and operations; Identifies, communicates and tracks cost sensitive items not included as part of the standard process
  • Collaborate on review, analysis and development of recommendations for the design of complex account and benefit structures based on client’s objectives and PayFlex’s systems, administration and reporting requirements
  • Participate in high profile client finalist meetings representing the capabilities of the organization’s implementation services process; identifies opportunities for cross sales and account rounding of additional PayFlex products and services throughout the implementation process
  • Effectively manage implementation team dynamics and provides direction/coaching to fellow team members ensuring success of the overall implementation process; engages team members to follow-through on their responsibilities and tasks
  • Assist the Manager in monitoring activities such as:
  • Meeting established service levels
  • Designing and testing of new product offerings and new software applications
  • Providing backup support for team members and supervisors
  • Maintain a positive work atmosphere with the team and internal departments
  • Assist in developing, updating, and reviewing internal Institutional Client Success, Client Onboarding policies and desktop procedures
  • Utilize sound judgment to escalate issues that may require intervention of the Manager
  • Prepare team statistics and reports
  • Manage special projects
  • Suggest and implement improvements to internal processes
  • Other duties as assigned.

Preferred Qualifications

Years of Experience:

  • 5-7 years of experience . Degree:
  • Bachelor’s Degree in Business, Communications, Finance, or related field . Certification: N/A . Skills & Abilities:
  • Strong relationship and communication skills
  • Bilingual language skills preferred
  • Possess a high level of knowledge regarding IRAs and applicable IRS code
  • Action oriented - should be motivated by challenging opportunities and thrive in fast paced environments
  • High level of composure - must be cool under pressure and in challenging situations and respond in a patient and professional manner
  • Operate efficiently with a high degree of accuracy
  • Consistent, sound decision making capabilities - must make consistently good decisions using blend of knowledge, experience and analysis
  • High level of ethics and values - must act in accordance with an appropriate set of core beliefs and within Inspira's personal code of conduct.
  • Experience in solving complex issues, both independently and in a collaborative team environment
  • Excellent analytical skills with a proactive nature
  • Proficiency in Microsoft Excel, Word (including mail merge) and Outlook
  • Experience with Salesforce CRM and Trust Accounting Systems preferred
  • Strong collaboration skills

Pay Range

$76,000-$83,000 per year

Compensation & Benefits

The compensation for this position will vary depending on factors such as your location, skills and experience. The compensation package may also include incentive and bonus opportunities.

Inspira provides industry-leading benefits including, but not limited to: healthcare, 401K savings plan, company holidays, paid time off, parental leave and an employee assistance program.

Salary : $76,000 - $83,000

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