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!

Location: 100% Remote

Reports to: Chief Technology Officer


If you are comfortable operating in a high-growth industry, fast-paced environment and embracing emerging technologies, you will thrive in our environment. Dealer Inspire (DI) will provide you the ability to advance your skills, showcase your talents, contribute with visible value and enjoy your work environment. Our environment is entrepreneurial, our resources are solid, our philosophy is teamwork-oriented and we thrive on grit.

Reporting to the Chief Technology Officer, the VP, Cloud Infrastructure and Security will have a unique opportunity to help lead our business to the next level and beyond. You will provide leadership, development, direction and help instill a DevSecOps culture across the entire engineering team in support of our cloud-based platform, website and technology solutions. 

About the Position

The VP, Cloud Infrastructure and Security, will play a strategic role in bringing a modern vision to engineering.  You will lead the design, build, and operational management of highly secure and scalable sites, platforms and products for Dealer Inspire. Additionally, you will promote, create, execute and reinforce frameworks, best practices and tools that allow DI to develop and deploy secure, high-quality products while driving our future roadmap.

Essential Job Functions:

  • Work with the CTO and other senior technology leadership to deliver a clear technology infrastructure and security strategy to support DI website, platform, and other technology products.
  • Participate in financial forecasting and annual budget planning.
  • Partner with cross-organizational technology leadership and business stakeholders (Cars.com, DealerRater, and FUEL) to ensure delivery of a clear technical roadmap for the platform to support the technical road maps for each product.
  • Translate security concepts into language that is meaningful to varying audiences, including business and technical leaders maintaining a balance between security & usability.
  • Own responsibility for the commercial justification of adopting new technology through clearly defined, measurable value propositions.
  • Ensure industry best practices are being adopted in terms of Infrastructure Architecture, Security, Continuous Delivery and Integration (CI/CD), Deployment, Support and Test automation.
  • Develop and lead product security architecture, security testing, secure design review, security engineering, and reporting.
  • Ensure that security risks are effectively identified using market-leading tools (SAST, DAST, SCA, etc).
  • Automate the build processes for DI, ensuring builds at the team level can be securely achieved in a timely manner.
  • Serve as a thought leader or cultivate thought leadership and subject matter expertise for DevOps and Security industry trends, new and existing technology offerings, and architectural concepts.
  • Establish and enhance KPIs and metrics that ensure a high bar for uptime, and provide deep visibility into the health of the platforms.
  • Provide leadership and direction for standard processes and tools for critical areas including but not limited to: site migration, security and compliance, threat monitoring, and compliance.
  • Select, coordinate, develop, and maintain relationships with vendors.
  • Recruit, build, and play a mentorship role to key engineering personnel, constantly promoting improvement in their professional skills and readying them for the occupation of your position in the future.


Required Skills:

  • Proven success in leadership with focuses on a DevSecOps culture, operational excellence, infrastructure security architecture, risk management and engineering creativity in SaaS environments.
  • Solid technical background, with hands-on DevOps related experience in automated, CI/CD, agile environments delivering infrastructure, monitoring and tooling to high-traffic cloud-based products.
  • Proven experience deploying current technologies including Cloud Services (AWS), microservices and serverless technology.
  • Experience with the full software development lifecycle and delivery(SDLC) using Agile and Scrum practices.
  • Expertise with security technologies and integration such as code scanning, open source scanning, vulnerability analysis, and security for automated deployments.
  • Experience with compliance frameworks and security requirements such as PCI, PII, GLBA, HIPAA, GDPR, SOC 2, ISO 27001, NIST, etc.
  • Proven track record of building, leading, and motivating highly talented remote teams to work in agile, cross-functional environments ensuring that modern technology and processes are implemented.
  • Strong influencing skills leading technology discussions at the senior leadership level
  • Ability to collaborate and manage relationships with other business units, external vendors and stakeholders.
  • Strong work ethic, self-directed and resourceful.
  • Passionate about creating powerful, disruptive technologies that transform how companies do business.

Experience and Education:

  • 10+ years of management experience
  • 5+ years in a leadership/executive role promoting a DevSecOps culture
  • 5+ years managing teams of 10+ multi-disciplined engineering professionals
  • 5+ years of experience with security architecture or security management in complex, cloud-based environments 
  • Bachelor’s Degree in Computer Science, Engineering, or related technical field
  • MBA or Master’s Degree in a technical field a plus
  • CISSP or CISM certification a plus

Benefits & Perks:

  • Health Insurance with BCBS, Delta Dental (Orthodontics coverage available), Vision
  • 401k plan with company match
  • Tuition Reimbursement
  • 18 days paid time off, parental leave, and selected paid holidays
  • Life and Disability Insurance
  • Subsidized gym membership
  • Subsidized internet access for your home
  • Peer-to-Peer Bonus program
  • Work from home Fridays
  • Weekly in-office yoga classes
  • Fully stocked kitchen and refrigerator

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

#LI-LH  #LI-Remote

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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