Retirement and Wealth - Sr. Support Specialist (Remote)

Inspira Financial; Oak Brook (IL); On-site; USD 27,000 - 32,000; Full time

Benefits offered by this job

Healthcare benefits

401K plan

Paid time off

Parental leave

Job summary

Inspira Financial is seeking a Sr. Support Specialist to manage high-level customer communications via email, chat, and text, focusing on complex financial products such as FSA, HSA, COBRA, and Rollover plans.

You will collaborate with internal departments to resolve client inquiries and contribute to policy development. Ideal candidates will have 2–4 years in customer service and 3+ years in financial services, with Salesforce experience and strong written communication.

Qualifications

• Must have 2-4 years of experience in customer service/call center
• 3+ years of experience in financial services preferred
• Experience with health reimbursement accounts such as FSA, HSA, COBRA or R&W knowledge preferred
• Proficient with Microsoft Office and multiple systems

Responsibilities

• Respond and resolve incoming and outgoing accountholder emails, chats, voice calls, or texts.
• Manage escalated client situations and assist Managers with follow-up with accountholders.
• Understand processes, timelines, and next steps with accountholder with clear language.
• Troubleshoot issues related to completing required forms and online guidance.
• Provide feedback and recommendations on processes and technology to internal teams.
• Mentor new Support Specialists; support new applications and tools.
• Support Teams Leads and Managers as needed.
• Demonstrate alignment with company values in interactions.

Skills

Customer service

Financial services experience

Salesforce/Service Cloud

Bilingual language skills

Written communication

Multi-channel support

Problem solving

Attention to detail

Education

High School Diploma or equivalent

Bachelor’s degree preferred

Tools

Salesforce/Service Cloud

Job description

Join Us!

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.

Our office locations are designed to bring people together, foster collaboration, and build meaningful connections. While some roles are based at one of our office locations, remote status and role locations are subject to change, and relocation is not provided.

Job Summary & Responsibilities

The Sr. Support Specialist is responsible for ownership of additional communications channels with accountholders or members who reach our contact center primarily through email, chat, or text. The role provides valuable advanced-level support and education on products like Flexible Spending Accounts (FSA), Healthcare Savings Accounts (HSA), COBRA (H&B) or Automatic Rollover/Direct Rollover plans (R&W). The Sr. Support Specialist will typically handle more complex or delicate issues, including time sensitive or escalated cases.

The role also assumes the primary responsibility of interacting with all the necessary internal Inspira departments to resolve client requests or answer any inquiries related to their account activity and investments. Through excellent verbal and written communications, the individual in this position develops, strengthens, and maintains a positive relationship with our clients and firm associates.

The Sr. Support Specialist also assists other senior members of the ACES Department in developing and updating internal Policies and Procedures. This role involves assisting Team Leads and Managers with mentoring new team members as well as supporting all staff on any new applications or tools. A Sr. Support Specialist is a Subject Matter Expert (SME) in all areas of their division at Inspira.

Duties & Responsibilities

• Respond and resolve incoming and outgoing accountholder emails, chats, voice calls, or texts.
• Manage escalated client situations and assist Managers with following up with accountholders.
• Understand and be able to articulate processes, timelines, and next steps with accountholder with clear, common language
• Strong ability to troubleshoot issues related to completing required forms and assisting with online guidance.
• Ability to provide feedback and recommendations on processes and technology to our internal teams, both written and orally
• Assist with mentoring new Support Specialists
• Assist with supporting Support Specialists on new applications and tools
• Provide support and assistance to Support Specialists, Team Leads, and Managers as needed.
• Provide feedback and suggestions to the training team
• Showcase alignment with our company values in every interaction with accountholders and team members
• Participate in pilots, UAT, and other new programs as needed
• Other duties as assigned

The typical schedule for this position is Monday through Friday, from 9:30 a.m. CT to 6 p.m. CT or 10:30 a.m. CT to 7 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:

• High School Diploma or equivalent required
• Bachelor’s degree preferred
• 2-4 years of experience in customer service/call center required
• 3+ years of experience in financial services industry preferred

Skills & Abilities

• Knowledge and experience with health reimbursement accounts such as Flexible Spending Accounts (FSA), Healthcare Savings Accounts (HSA), and COBRA (H&B) required OR knowledge and experience with retirement accounts and IRS rules and regulations (R&W) required
• Experience with Salesforce/Service Cloud required
• Bilingual language skills are preferred.
• Ability to work in a high-volume environment, support multiple channels – email, chat, voice and/or text.
• Possesses expert written and verbal communication skills.
• Detail-oriented, organized, and dependable -- these are small teams, dependability and accountability are key!
• Energetic, client service focused individualwho consistently demonstrates patience and empathy
• Ability to apply relationship building skills to internal and external clients.
• Proactive approach to resolving issues.
• Active Listening Skills
• Takes accountability with great follow through skills.
• Ability to solve complex issues, both independently and in a collaborative team environment with a focus on FCR (first call resolution)
• Strong computer aptitude; proficient in Microsoft suite of products, keyboarding of 50 WPM+
• Strong problem-solving skills and ability to multi-task and ability to navigate several systems simultaneously to support servicing the client.
• 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.

Other Requirements

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

Pay Range

$19.50/hr-$23.50/hr

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.