Sr. Accounting Billing Specialist (Remote)

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.
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.
Join us on our journey as we work together to take on the complex and the everyday--turning collective effort into life-changing impact that enriches lives and helps build a better future. Learn more at inspirafinancial.com.
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? That's okay. At Inspira Financial, we know growth comes from people who are willing to learn, challenge themselves, and aim higher. We value individuals who lead with heart, cultivate trust, and collaborate to win together. If you're energized by meaningful work, continuous development, and being part of a team that turns collective effort into real impact, Inspira Financial could be the right next step in your journey. We look forward to receiving your application.
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 Sr. Accounting Billing Specialist is responsible for accurately processing and reviewing billing transactions, executing invoices, and ensuring contract-based billing accuracy within the accounting framework. This role partners closely with internal departments to resolve billing inquiries and support operational and financial reporting needs. The position also supports the Billing Team Lead and accounting leadership through involvement in system enhancements, audit support, and cross-functional initiatives impacting billing and accounting operations.
Duties & Responsibilities:

• Prepare and process daily, monthly, quarterly, and annual invoices.
• Review and audit invoices prior to client release to ensure accuracy.
• Interpret client contracts and fee schedules for correct billing setup.
• Set up new clients in the accounting system for billing.
• Process termination cases within established SLAs.
• Respond promptly to billing inquiries and requests via email, instant message, and Salesforce.
• Assist Account Managers with billing questions, corrections, and adjustments.
• Support annual audits (financial statements, regulatory reporting, SOC-1).
• Assist with billing integrations during acquisitions to ensure smooth transitions.
• Contribute to developing and improving departmental policies, procedures, and workflows.
• Support the Billing Team Lead and accounting leadership with special projects and ad-hoc analyses.
• Participate in the daily workflow and operations of the billing department.
• Perform other duties as assigned within the nature and level of work.

Preferred Qualifications
Education & Experience

• Bachelor's Degree in Accounting, Finance, or related field
• A minimum of five (5) years of experience in billing, accounting, or related financial operations

Skills & Abilities

• Advanced proficiency in Microsoft Excel (pivot tables, advanced formulas)
• Strong analytical and problem-solving skills
• Excellent written and verbal communication skills
• Strong organizational, planning, and time-management capabilities
• Ability to collaborate effectively at all levels within the organization
• Experience with Sage/Intacct preferred

Other Requirements

• Standard schedule is Monday through Friday from 8:00 a.m. to 5:00 p.m. Central Time. Additional hours may be required during peak periods
• Employees within a 90-minute radius of Oak Brook, Illinois must work onsite at least four days per month between 10:00 a.m. and 2:00 p.m. Central Time, including one Monday or Friday each month
• Occasional travel up to five percent may be required, including the ability to use personal transportation for trainings or meetings

Compensation & Benefits
$23.00/hr-$25.00/hr