Director, Enterprise Applications

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

We are looking for a forward-thinking Director of Enterprise Applications who thrives in a dynamic environment, driving application innovation, strategic alignment, and operational excellence.

The Director of Enterprise Applications is a transformative leader responsible for steering the strategic direction while ensuring the execution of cutting-edge enterprise-wide business applications solutions at global scale. As a proactive change leader, the Director will foster a culture of continuous improvement, guiding cross-functional teams through digital transformation initiatives, ensuring alignment with organizational goals, and delivering measurable business value.

The Director will collaborate closely with senior leadership, business units, and technology teams to ensure effective solutions delivery, operational efficiency, scalability, and security.

This individual will lead the Enterprise Applications team, foster innovation, optimize application portfolios, and ensure robust governance and compliance.

Who you are

Leadership & Strategic Alignment

• Develop and execute a strategic roadmap for enterprise applications, aligning technology solutions with the company's long-term business objectives.
• Provide visionary leadership, fostering innovation, collaboration, accountability, and continuous improvement within the Enterprise Applications team.
  Build, manage, and mentor high-performing teams, clearly defining roles, responsibilities, and key performance indicators (KPIs).
• Leverage deep expertise in Artificial Intelligence (AI) to champion innovation and lead the team in identifying, developing, and deploying cutting-edge AI-driven solutions that enhance business performance and operational efficiency
• Act as a senior advisor and strategic partner to executives and departmental leaders, providing recommendations and guidance on application-related strategies.

Enterprise Application Management

• Oversee the planning, implementation, and continuous improvement of enterprise application solutions, including CRM, FinTech, MarTech and other business-critical enterprise platforms.
• Lead large-scale enterprise application projects, including system upgrades, integrations, migrations, and process automation.
• Drive application modernization initiatives, emphasizing cloud solutions, automation, AI, and emerging technologies to enhance organizational efficiency and agility.
  Establish robust governance, compliance frameworks, and best practices to ensure data integrity, cybersecurity, regulatory compliance, and operational reliability.

Operational Excellence

• Monitor and optimize the performance, availability, scalability, and cost-effectiveness of the enterprise application portfolio.
• Set clear performance metrics and regularly evaluate application effectiveness, driving continuous improvements and proactive resolution of issues.
• Ensure timely delivery of application projects, effectively managing risks, dependencies, and resource constraints.
• Coordinate closely with cross-functional IT teams (Infrastructure, Cybersecurity, BI/Data Analytics) to ensure cohesive delivery and alignment of enterprise-wide solutions.

Vendor Management & Budget Oversight

• Manage strategic vendor partnerships, negotiate contracts, and ensure delivery against service-level agreements.
• Develop and manage the enterprise applications budget, ensuring strategic alignment and optimal allocation of resources.
• Develop clear business cases to justify investments in enterprise application enhancements, integrations, and major implementations.

Communication & Collaboration

• Serve as the primary point of escalation for enterprise application issues, maintaining clear communication with stakeholders regarding resolution timelines and impacts.
• Communicate clearly and consistently with all stakeholders, providing regular updates on strategic initiatives, risks, progress, and application performance.
• Foster strong working relationships with business stakeholders, ensuring enterprise applications continuously support business needs.

What you'll bring

• Bachelor's degree (Master’s preferred) in Information Technology, Computer Science, Business Administration, or related field.
• Minimum of 10+ years in senior leadership roles, specifically managing enterprise application portfolios, including CRM, FinTech, MarTech and other business-critical enterprise platforms.
• Proven track record of successfully leading complex enterprise application implementations, integrations, migrations, and digital transformation initiatives.
• Extensive experience with cloud-based enterprise application solutions, SaaS implementations, and application lifecycle management.
• Deep knowledge of enterprise application architecture, integration methodologies, and related cybersecurity best practices.
• Strong business acumen with demonstrated ability to align technology strategies to organizational objectives and outcomes.
• Proven experience managing large-scale vendor relationships, negotiating favorable terms, and overseeing substantial budgets.
• Exceptional strategic planning, analytical thinking, problem-solving, and decision-making skills.
• Excellent leadership, communication, and stakeholder management capabilities, with the ability to effectively articulate complex technical strategies to non-technical audiences.
• Commitment to continuous learning, staying abreast of emerging trends, technologies, and best practices in enterprise application management and governance.

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