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Integration and Financial Systems Manager

About Us: 

Dealer Inspire was acquired by in February 2018.  It 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.  This role will be based in our Naperville, IL office and will have periodical visits to the downtown Chicago office.  We have a dynamic culture, start-up office environment, benefits of a larger organization and a grit and get stuff done mentality.  This short video should provide you with some context as to our culture and work environment

Job Description:

This is an exciting and dynamic role for an innovative leader who embraces a fast pace environment, a collaborative team approach and thrives in the ability to transform a successful start-up environment to a more scalable mid-size company. The Manager, Integration and Financial Systems will be responsible for all aspects of the architecture, design, implementation and execution of the financial billing system and the migration from QuickBooks to PeopleSoft.  This leader will be instrumental in change management and process improvement transforming the current state to the future state as we modernize our financial systems and create a foundation for scale.  

This leader will understand the business needs, learn the current processes, identify areas of opportunity and design new processes to achieve scale, compliance, simplicity and delight our clients with outstanding results.  A solid understanding of financial processes, internal controls, Peoplesoft, Salesforce, Quickbooks and financial management is preferred.  The ability to conceptualize an end state, align the business toward the end goal, communicate a path forward and articulate and design a roadmap for execution is essential.  A successful individual will be an effective partner to various stakeholders across the business, the ability to understand needs, constraints and timelines and the tenacity to deliver on results.

This leader will develop financial processes, set procedures, integrate with the parent company’s financial systems and lead the overall integration of the billing system from QuickBooks to PeopleSoft.  A successful leader will be a quick study of the landscape, will have a strong opinion, will be well versed with data driven recommendations and will be comfortable with executive interaction.  The Integration and Financial Systems Manager will report to the COO and will have a significant voice in the evolution of the financial systems.


  • Quickly understand and learn the current billing process and complete a process map of current state
  • Interview stakeholders and incorporate their input into the design of a new billing process 
  • Architect and roadmap the design and implementation of the new billing system
  • for scale and efficiency
  • Build a billing process and system with the PeopleSoft team ensuring compliance with internal controls, segregation of duties and scalability.
  • Document processes and procedures for the new billing system.
  • Identify opportunities for improvement and refinement of key financial processes and procedures
  • Develop and implement processes for internal controls over financial reporting that will scale with the growing company
  • Develop cross-functional relationships through-out the organization to understand current trends of the business
  • Special projects on an as-needed basis
  • This role will not have any direct reports but will work directly with the COO, accounting team, sales team, performance management team, OEM team and FP&A Manager at Dealer Inspire as well as the Director of Corporate Accounting and Reporting at

Required Skills:

  • Ability to understand process, systems, opportunities and paint a future state vision and align the organization to execute
  • Ability to partner with the Salesforce team to drive billing efficiencies, comply with controls and build a foundation for scalability
  • Strong focus on accuracy and high attention to detail
  • Ability to effectively research and compile data from financial reporting systems, databases, spreadsheets, and other data sources
  • Knowledge of billing systems and appropriate skills in financial analysis and reporting
  • Ability to manage and balance multiple priorities and urgent requests effectively, with the ability to quickly adapt for changing business needs
  • 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

Required Experience: 

  • Bachelor’s degree or higher in Accounting or Business Administration
  • 5-7 years of progressive accounting, financial systems experience 
  • Public company experience is preferred but not required
  • Demonstration of achievement and leadership


  • Health Insurance with BCBS
  • 401k plan with company match
  • 10 days paid time off, 4 days of sick leave and selected paid holidays
  • Dental, Life and Disability Insurance
  • Subsidized gym membership
  • Subsidized internet access for your home
  • Peer to Peer Bonus program
  • Work from home Fridays
  • Stocked fridge with snacks and more!
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