Sr. Implementation Manager (Remote)

About Us

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. Our values shape how we show up every day:

• 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;
• Win Together by collaborating inclusively to achieve the best outcomes.

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. We relentlessly pursue better outcomes for all with our automatic rollover services, health savings accounts, emergency savings funds, custody services, and more.

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.

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.

About the Role

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 positive relationships with our clients and firm associates. This role provides focused service from pre-sale consultation through initial post-sale client administration, fostering strong, long-term partnerships with customers and the consulting community.

Responsibilities

• Direct all aspects of customer benefit plan installation for new and existing high-profile, large, complex customers of PayFlex's products and services.
• Develop and execute an implementation strategy consistent with customer expectations, creating, managing, and tracking detailed project plans and issue logs outlining required actions, responsible parties, and assigned target dates.
• Act as the single point-of-contact for benefit plan implementation; mediate and coordinate 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 (e.g., 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 the impact of client-requested exceptions and develop reasonable alternatives to satisfy client needs while minimizing impact on systems and operations; identify, communicate, and track cost-sensitive items not included as part of the standard process.
• Collaborate on the review, analysis, and development of recommendations for the design of complex account and benefit structures based on client 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; identify opportunities for cross-sales and account rounding of additional PayFlex products and services throughout the implementation process.
• Effectively manage implementation team dynamics and provide direction/coaching to fellow team members, ensuring the success of the overall implementation process; engage 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 new product offerings and software applications, and 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 and Client Onboarding policies and desktop procedures.
• Utilize sound judgment to escalate issues that may require intervention by the Manager.
• Prepare team statistics and reports.
• Manage special projects and suggest and implement improvements to internal processes.
• Perform other duties as assigned.

Qualifications

• Years of Experience: 5-7 years.
• Degree: Bachelor’s Degree in Business, Communications, Finance, or related field.
• Skills & Abilities:
  • Strong relationship and communication skills.
  • Bilingual language skills preferred.
  • High level of knowledge regarding IRAs and applicable IRS code.
  • Action-oriented—motivated by challenging opportunities and thrives in fast-paced environments.
  • High level of composure—must be cool under pressure and respond in a patient and professional manner.
  • Operate efficiently with a high degree of accuracy.
  • Consistent, sound decision-making capabilities—must make good decisions using a 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

$76,000-$83,000 per year.

Benefits

• Healthcare.
• 401K savings plan.
• Company holidays.
• Paid time off.
• Parental leave.
• Employee assistance program.
• Incentive and bonus opportunities.