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. Want to learn more? Check us out here!


This Chief Technology Officer will be experienced in leading world-class engineering organizations, owning both the strategic architectural platform while understanding how to build a lean engineering culture and aligning DI technology to the broader CARS technical direction. The right individual will be experienced in scaling technology teams and creating and delivering the technical architecture and infrastructure to support a great experience across a broad customer base.

This CTO will be the main driver in the planning, development, and implementation of DI’s application architecture, technology stack on the various platforms; and scaling those for the immediate future as well as broader. Also will be responsible for creating DI engineering best practices and technical philosophy and aligning those to that of CARS. As well as identifying and streamlining areas of overlap including support infrastructure, vendors etc; to create a best in class technology organization across all of CARS brands. 

This leader will be passionate about driving significant growth, self-starting, dynamic and able to promote a lean/agile culture. As well as developing outstanding technical leaders within Dealer Inspire to take on broader organizational opportunities.   The Chief Technology Officer will report into the CEO of Dealer Inspire with a dotted line to the CARS Chief Technology Officer.  This role will be instrumental in delivering a fantastic experience for current and future consumers.



  • Has led the organizational development and growth of engineering functions; strong ability to identify, hire, build and scale a world class engineering team 
  • Has executed successful technical strategies around building and scaling high quality platforms and systems.
  • Deep experience in consumer applications or SaaS solutions, as well as strong experience in systems engineering infrastructure, specifically related to performance, sustainability, scalability and security.  
  • Product “instincts”, having a sense of the relationship between product and engineering regarding design, experience, and partnerships
  • Success in an entrepreneurial environment, ideally within a start-up or high growth technology company.
  • Partner with business leaders across the company to effectively meet business objectives and execute on overall strategy.
  • Lead and inspire the engineering organization through connecting business goals to their work
  • Experience being the technology spokesperson and evangelist representing the company in external forums, conferences, etc.
  • Work with engineering, and  product management to develop innovative solutions that meet customer needs with respect to functionality, performance, scalability, reliability, security, realistic implementation schedules, and adherence to development goals and principles
  • Attract, lead, coach, develop and inspire top engineering talent in industry
  • Ensure there is a strong and driven culture that focuses on accountability and performance, with clear line of sight between organization strategy and individual goals
  • Highly analytical and structured thinker with an excellent ability to put complex ideas into clear frameworks and to use data to drive strategic objectives and priorities
  • Be a team player with excellent communication skills who thrives in a collaborative, entrepreneurial environment
  • Strong personal initiative and self-starter mentality. Needs to be able to thrive in a rapidly changing, fast-paced entrepreneurial environment

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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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