Retirement and Wealth - Support Specialist Team Lead (Remote)

Posted 2 Days Ago
Hiring Remotely in Chicago, IL, USA
In-Office or Remote
20-26 Hourly
Senior level
Fintech
Inspira Financial's innovative financial wellness solutions help people plan, save, and invest.
The Role
Leads support center specialists by providing real-time guidance, resolving escalated accountholder issues, coaching and training team members, monitoring service and quality goals, and supporting performance reviews. The role also tests new products and software, updates policies and training materials, answers client inquiries, improves service efficiency, and manages special projects. The schedule is Monday through Friday, 11:30 a.m. to 8:00 p.m. CT, with seven weeks of training.
Summary Generated by Built In
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 primary function of this role is to provide live, real-time assistance to support center specialists, which includes providing guidance in a digital work environment and being the first point of contact for all team members. Team Leads are also the first point for resolving escalated customer issues, which can include speaking to the accountholder, researching the reason for escalation, owning the resolution, and providing feedback and recommendations to the business. This role is also responsible for coaching/mentoring and refresher training of all members of the Support Department. This role will also involve providing feedback, conducting testing, implementation of new technology, software applications and product offerings. The Team Lead position assists in the review of all internal Policies and Procedures and training materials. Through verbal and written communications, the individual in this position develops, strengthens, and maintains a positive relationship with our accountholder team members, and firm associates.
Duties & Responsibilities:
  • Assist the Manager in monitoring activities of the Support team including but not limited to:
  • Providing front line assistance to the team
  • Being the first point for escalation and providing de-escalation coaching to team members
  • Coach the team to meet their quality and survey goals
  • Meeting established service levels
  • Coaching/Training team members, including providing feedback for mid-year and annual performance reviews.
  • Design and test new product offerings and new software applications.
  • Providing backup support for employees and managers
  • Maintain a positive work atmosphere with the team and internal departments.
  • Review and resolve complex accountholder requests
  • Assist in updating, and reviewing internal Policies and Procedures
  • Guide Team members to utilize Digital Coach tool in their workflow
  • Manage escalated client calls and assist managers with following up with account holders
  • Provide answers to client inquiries regarding Inspira's products, services, and fees
  • Provide direct feedback to team members on areas of opportunities to enhance services provided to the accountholder. Participate in providing feedback for mid-year and annual reviews.
  • Utilize sound judgment to escalate issues that may require intervention of the manager
  • Provide answers to accountholder inquiries regarding Inspira's products, services, and fees.
  • Maintain a professional approach to client service, consistent with Inspira's protocol and service levels.
  • Recommend and implement ways to improve efficiency and quality.
  • Manage special projects
  • Other duties as assigned

The typical schedule for this position is Monday through Friday, from 11:30 a.m. to 8:00 p.m. CT. Training for this position is 7 weeks. Training Schedule:
  • Tier 1 Training - 3 weeks (Following the Training Schedule from 8 a.m. CT to 4:30 p.m. CT)
  • Tier 1 Call Lab - 2 weeks (Following the Regular Schedule from 11:30 a.m. CT to 8 p.m. CT)
  • Tier 2 Training - 1 week (Following the Training Schedule from 8 a.m. CT to 4:30 p.m. CT)
  • Tier 2 Call Lab - 1 week (Following the Regular Schedule from 11:30 a.m. CT to 8 p.m. CT)

Preferred Qualifications
Education & Experience:
  • Bachelor's degree in business, Communications, or related field
  • 5-7 years of applicable experience

Skills & Abilities:
  • Knowledge and experience with Retirement Accounts and IRS rules and regulationsfor R&W OR knowledge of reimbursement accounts like FSA and HRA for H&B
  • Able to transfer knowledge and coach in a 1-1 setting
  • Energetic, client service focused individual
  • Possesses strong written and verbal communication skills.
  • Able to apply relationship building skills to internal and external clients.
  • Has strong computer aptitude; proficient in Microsoft suite of products
  • Display timely and accurate decision making.
  • Strong problem-solving and decision-making skills and ability to multi-task, and ability to navigate several systems simultaneously to support servicing the client.
  • Is detail-oriented, organized, and dependable
  • Active Listening skills
  • Innovative Thinker
  • Patience/empathy
  • Proactive approach to resolving issues
  • Be able to work in a high volume, fast paced environment
  • Takes accountability with great follow through skills
  • Ability to maintain the highest quality of service and professionalism.
  • Possess a cheerful outlook and be able to perform well in a collaborative team environment.
  • Ability to solve complex issues, both independently and in a collaborative team environment with a focus on FCR (first call resolution)
  • Working knowledge of Salesforce/Service Cloud preferred
  • Working knowledge of trust accounting systems preferred, including some familiarity with investments (R&W only)
  • Bilingual language skills are preferred.

Other Requirements:
  • Ability to work overtime when needed.
  • Prolonged periods of sitting at a desk and working on a computer

Compensation & Benefits
$20.45/hr-$25.50/hr

Skills Required

  • Bachelor's degree in business, Communications, or a related field
  • 5-7 years of applicable experience
  • Knowledge and experience with retirement accounts and IRS rules and regulations, or reimbursement accounts such as FSA and HRA
  • Ability to transfer knowledge and coach individuals one-on-one
  • Strong written and verbal communication skills
  • Strong problem-solving and decision-making skills
  • Ability to work in a high-volume, fast-paced environment
  • Working knowledge of Salesforce Service Cloud
  • Working knowledge of trust accounting systems and familiarity with investments for retirement and wealth support
  • Bilingual language skills
  • Ability to work overtime when needed
  • Ability to sit for prolonged periods and work at a computer

What the Team is Saying

Hugh
Rachel Nielsen
Albert
Rebecca Karnoscak
Lauren Schulz
Oliver Siafa

Inspira Financial Compensation & Benefits Highlights

  • Leave & Time Off Breadth — The package advertises substantial PTO, 10 paid holidays, and dedicated volunteer time off, alongside paid parental leave. These provisions indicate broad time-away support across multiple leave types.
  • Retirement Support — A 401(k) with a “generous” employer match is highlighted, with tax-advantaged accounts (HSAs/FSAs) administered in-house to simplify savings. This combination supports longer-term financial security and ease of use.
  • Wellbeing & Lifestyle Benefits — Offerings include a mindfulness/meditation app subscription, pet insurance, and other lifestyle perks. These additions round out the core benefits with everyday wellbeing support.

Inspira Financial Insights

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The Company
HQ: Oak Brook, IL
1,805 Employees
Year Founded: 2000

What We Do

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.

Why Work With Us

Inspira Financial is a leading financial services company offering specialized financial wellness solutions to employers, institutions, advisors, and individuals.

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Inspira Financial Offices

Remote Workspace

Employees work remotely.

Typical time on-site: None
HQOak Brook, IL
Accruit an Inspira Financial Solution
Longwood, FL
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