Director of Information Technology at CarGurus in Boston, MA

Who we are

At CarGurus (NASDAQ: CARG), our mission is to give people the power to reach their destination. We started as a small team of developers determined to bring trust and transparency to car shopping. Since then, our history of innovation and go-to-market acceleration has driven industry-leading growth. In fact, we're the largest and fastest-growing automotive marketplace, and we've been profitable for over 15 years.

What we do

The market is evolving, and we are too, moving the entire automotive journey online and guiding our customers through every step. That includes everything from the sale of an old car to the financing, purchase, and delivery of a new one. Today, tens of millions of consumers visit CarGurus.com each month, and ~30,000 dealerships use our products. But they're not the only ones who love CarGurus-our employees do, too. We have a people-first culture that fosters kindness, collaboration, and innovation, and empowers our Gurus with tools to fuel their career growth. Disrupting a trillion-dollar industry requires fresh and diverse perspectives. Come join us for the ride!

Role overview

The Director of Information Technology (IT) is a strategic leader responsible for being a change agent for innovation, optimizing IT assets (software, hardware, and people), and ensuring the alignment of IT solutions with business goals and objectives. This role requires a visionary approach to technology adoption, a deep understanding of cutting-edge IT trends, and the ability to lead a high-performing team in a fast-paced, agile environment. The Director of IT will work closely with senior leadership to develop and implement technology strategies that enhance operational efficiency, security, and scalability.

This individual will leverage the company's strategic objectives to develop robust team-level and individual contributor goals, manage and mentor a team of IT professionals, and ensure the effective delivery of technology solutions.

They will oversee corporate IT Systems Administrations, Solutions, and Service Desk teams which operate both inside and outside the United States.

What you'll do

Leadership & Team Management

Foster a culture of innovation, agility, and collaboration while holding team members accountable for their deliverables
Develop and implement training programs and user documentation to empower employees to leverage IT tools effectively
Lead IT and corporate policy adoption and alignment with business stakeholders
Build and manage high-performing IT teams with clear goals, key performance indicators (KPIs), and a focus on continuous improvement
Provide leadership with frequent updates, including successes, challenges, and strategic recommendations
Act as a primary point of escalation for IT-related issues, ensuring swift resolution and minimal disruption
Be a thought partner to team members on the development of comprehensive system/application documentation, including requirements, processes, and procedures
Develop and coach senior staff, fostering an inclusive and high-performing work environment
Conduct performance assessments including individual and team opportunities for increased impact and effectiveness
Manage relationships with technology vendors, partners, and contractors
Manage IT budget in collaboration with senior management and our FP&A partner ensuring alignment with the company's financial and strategic goals
Assume leadership of IT Software Governance Committee to drive decisions and actions

Technology Strategy & Execution

Develop annual strategic roadmap to enhance business capabilities and efficiencies
Oversee the development and execution of the IT strategies and manage multiple large scale projects concurrently
Lead the adoption of automation, and AI-driven technologies to enhance operational efficiency for corporate IT applications
Confirm that cybersecurity requirements are implemented to protect company IT assets and meet compliance with industry regulations
Optimize IT infrastructure, ensuring high availability, scalability, and cost-effectiveness
Negotiate vendor contracts and service level agreements to maximize value
Identify emerging information technologies to keep the company at the forefront of innovation keeping our IT ecosystem modernized
Develop business cases for major system implementations, upgrades, and technology investments
Establish IT governance frameworks and best practices to ensure data integrity, security, and compliance
Define and monitor KPIs to track IT performance, encouraging continuous improvement
Ensure timely delivery of IT projects, addressing risks, dependencies, and resource constraints
Plan and execute IT communication strategies, keeping stakeholders informed of key developments
Maintain a strong understanding of Identity Access Management and Governance (IAM/IAG) and Privileged Access Management (PAM) standards
Act as the team's primary point of contact for escalated issue (system/staff) resolution, resource capacity and quarterly planning

What you'll bring

Bachelor's or Master's degree in Information Technology, Computer Science, or related field
10 years of experience in IT leadership roles within a technology-driven environment; this is not a step-up role, have to been there and done it before
Strong experience in system administration, infrastructure, solutions engineering, IT service desk operations
Solid understanding of Agile methodologies, modern IT service management practices and proven track record of implementation of them on a large team.
Have worked with Cybersecurity and Enterprise Applications team and can comprehend and converse about those areas
Proven experience leading IT transformation and digital innovation initiatives
Ability to align IT strategy with business objectives, ensuring technology drives company success
Experience managing IT budgets, vendor relationships, and technology investments
Strong leadership, communication, and stakeholder management skills
Strong project management skills with the ability to lead large-scale initiatives, on time and budget
Commitment to continuous learning, staying updated with the latest IT trends and industry best practices
Ability to develop and coach senior staff, fostering an inclusive work environment
Strong understanding of functional goals with the ability to positively influence team efficiency
Effective communication and interpersonal skills, with the capability to collaborate with others
Ability to prioritize and act quickly on priorities if we need to pivot

Working at CarGurus

We reward our Gurus' curiosity and passion with best-in-class benefits and compensation, including equity for all employees, both when they start and as they continue to grow with us. Our career development and corporate giving programs, as well as our employee resource groups (ERGs) and communities, help people build connections while making an impact in personally meaningful ways. A flexible hybrid model and robust time off policies encourage work-life balance and individual well-being. Thoughtful perks like daily free lunch, a new car discount, meditation and fitness apps, commuting cost coverage, and more help our people create space for what matters most in their personal and professional lives.

We welcome all

CarGurus strives to be a place to which people can bring the ultimate expression of themselves and their potential-starting with our hiring process. We do not discriminate based on race, color, religion, national origin, age, sex, marital status, ancestry, physical or mental disability, veteran status, gender identity, or sexual orientation. We foster an inclusive environment that values people for their skills, experiences, and unique perspectives. That's why we hope you'll apply even if you don't check every box listed in the job description. We also encourage you to tell your recruiter if you require accommodations to participate in our hiring process due to a disability so we can provide the appropriate support. We want to know what only you can bring to CarGurus. #LI-Hybrid