Dealer Inspire (DI) is a leading disruptor in the automotive industry through our innovative culture, legendary service, and kick-ass website, technology, and marketing solutions. Our mission is to future-proof local dealerships by building the essential, mobile-first platform that makes automotive retail faster, easier, and smarter for both shoppers and dealers. Headquartered in Naperville, IL, our team of nearly 600 work friends are spread across the United States and Canada, pushing the boundaries and getting **** done every day, together.

DI offers an inclusive environment that celebrates collaboration and thinking differently to solve the challenges our clients face. Our shared success continues to lead to rapid growth and positive change, which opens up opportunities to advance your career to the next level by working with passionate, creative people across skill sets. If you want to be challenged, learn every day, and work as a team with some of the best in the industry, we want to meet you. Apply today!

Dealer Inspire is a CARS brand. CARS includes the following brands: Cars.com, Dealer Inspire, DealerRater, FUEL. Want to learn more? Check us out here!


Dealer Inspire is looking for a Senior Billing Manager to join our growing Finance organization and to fully manage the processes and people responsible for all client billing operations.  The ideal candidate has a passion for finding solutions and creating processes that support strategic opportunities for our company.  This role is responsible for designing, implementing and enforcing policies and procedures, as well as streamlining effective billing processes across the organization.  

The Senior Billing Manager will be a key stakeholder and leader in an upcoming billing system conversion, which will result in more efficient billing processes and alignment of systems with our Parent organization.

Dealer Inspire is an innovative technology leader that has been rapidly increasing its market share by providing progressive automotive dealer websites, digital retailing and messaging platforms products as well as marketing services including paid, organic, social and creative services.

Responsibilities include:

  • Managing the completion, accuracy, and timeliness of monthly billing
  • Leading the hiring, training and continual coaching and development of the Billing Specialists
  • Identification and implementation of process improvements to streamline the billing process
  • Being a key stakeholder and leader in an upcoming billing system conversion
  • Completion of SOX controls
  • Managing the preparation and analyzing the results of revenue related reconciliations
  • Assisting with annual financial statement and internal control audits
  • Working cross-functionally with the Program Manager, Business Intelligence and Sales teams on various billing related issues
  • Create and distribute periodic billing metrics and ah-hoc reports to Senior Leadership
  • Commitment to customer service excellence


  • Strong leadership skills
  • Deep understanding of subscription billing and financial concepts
  • Ability to perform strategic planning and priority setting for a Billing department
  • Ability to manage and balance multiple priorities and urgent requests effectively, with the ability to quickly adapt for changing business needs
  • Ability to seek out new methods and be willing to incorporate them into existing practices
  • Focus on accuracy and high attention to detail
  • Ability to effectively research, compile, and analyze data from financial reporting systems, databases, spreadsheets, and other data sources
  • Demonstrated ability to work both independently and collaboratively
  • Ability to work additional hours to meet periodic workload peaks and complete assignments in accordance with established deadlines
  • Passionate, energetic, approachable with a positive, low-ego, can-do demeanor
  • Ability to communicate effectively, both verbally and in writing, with all levels of management and external parties
  • Excellent problem solving and decision-making skills
  • Strong Excel skills (i.e. filters, pivot tables, v-lookups, count-ifs)

Required Experience:

  • Bachelor’s degree or higher in Accounting or Finance
  • 7+ years of Billing and Finance experience in a high-growth subscription based organization
  • 3+ years of management experience
  • Proven track record for improving processes and problem solving
  • Experience with Salesforce CPQ preferred

Benefits & Perks*:

  • 18 days of paid time off, plus select paid holidays
  • Paid Volunteer Day & Paid Pet Wellness Day
  • Work from home Fridays
  • Fully stocked kitchen and refrigerator
  • Robust Health Insurance Options: BCBS, Delta Dental, EyeMed
  • 401k plan with company match
  • Subsidized internet access for your home
  • Subsidized gym membership
  • Weekly in-office yoga classes
  • Parental Leave
  • Life & Disability Insurance
  • Tuition Reimbursement

*Not a complete, detailed list. Benefits have terms and requirements before employees are eligible. 


We are an equal opportunity employer and value diversity at our company. We do not discriminate on the basis of race, religion, color, national origin, gender, sexual orientation, age, marital status, veteran status, or disability status.


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We're focused on creating career chemistry for our team, and that means building a culture where diversity is a priority. All CARS employees are encouraged to bring their whole, authentic self to work every day, including their talents, passions, and unique ideas. Across all our brands, we encourage our teams to stay open, and combine their different backgrounds, experiences, and worldviews to deliver better results.
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