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Senior Director of Learning, Development & Employee Experience

CarGurus, Cambridge, MA

Find and share automotive knowledge


Car shopping is complicated. At CarGurus, we use data and technology to make it simple, giving people the tools they need to confidently find, buy, finance, or sell a car. The best part? Our work makes a real impact. We’re the most-visited car-shopping site in the US and we are growing fast in our international markets. Ready to come along for the ride?

CarGurus is looking for a Senior Director, Learning, Development & Employee Experience to join the People & Talent Team. Not only is this an exciting role but an exciting time to join us as we continue to build a diverse and inclusive learning and employee experience at CarGurus. The role is suited to a passionate individual, who will lead a team responsible for designing, developing and delivering learning and leadership development programs within the organization. In addition, this role will oversee our employee experience efforts across the company including, Diversity, Equity, Inclusion and Belonging, Internal Communications and Employee Engagement.

There are innumerable ways to learn, grow and excel professionally. We will review all applications and take a broad look at the experience of each applicant. We want to get to know you and the unique strengths you will bring to the role. This said, we are most likely to be interested in your candidacy if you can demonstrate the majority of the qualifications and experiences listed. We know that no person ever fits the exact profile of any job description. If you feel this role connects to your skills and purpose, we encourage you to bring your diverse experiences in applying for this role!

What You'll Do:

  • Lead a team that inspires an organization-wide culture of learning, growth and belonging across a global organization
  • Act as an ambassador for CarGurus’ Core Values, Leadership Principles and Commitments to Diversity, Equity, Inclusion and Belonging
  • Lead the learning & development team including onboarding, professional development, and leadership development
  • Partner with organizational leadership and P&T leadership to ensure a comprehensive and well-rounded learning program
  • Work with the training team to assess the training needs of the organization and help craft and develop new training materials to meet those needs
  • Oversee the development of innovative manager development programs including new manager training, online resources, toolkits and mentorship programs
  • Partner with Manager of DEI to develop the strategic roadmap for Diversity, Equity, Inclusion and Belonging and manage DEI team – as well as the cross-functional Diversity, Inclusion and Belonging Advisory Team
  • Collaborate with business leaders on development activities (speakers/activities/leader led trainings) that are aligned with employee development, leadership, culture, and DEI
  • Manage internal communications and employee engagement team (including internal comms platforms and roadmap, employee engagement survey and broad survey strategy)
  • Liaising with People and Talent teams (recruiting, total rewards, HR operations), be responsible for the design, development, and global rollout of learning and DEI resources, programs and events
  • Build communication processes to ensure consistent and clear communication
  • Work with Legal and HR to build compliance training

Who You Are:

  • 8-10 years of professional work experience in Learning and Organizational Development, Diversity, Equity, Inclusion, and/or Employee Engagement
  • Ability to lead organization-wide initiatives
  • Collaborator. You have the ability to bring diverse groups of individuals at varying levels of leadership together to work towards a common goal
  • You can balance moving quickly with designing thoughtful approaches to employee development, engagement and belonging
  • Proven expertise in curriculum design and development and ability to develop and coach team members to develop high quality adult learning
  • Great organizer and good at creating order out of uncertainty
  • Excellent facilitation skills and training experience that you can develop in team members and organizational partners
  • Have a growth mentality and ability to adapt and lead in a rapidly-changing environment
  • Superior communication skills, excellent verbal capacity and strong writing skills
  • Experience leading a complex team with related but diverse priorities
  • Ability to prioritize multiple, large-scale initiatives simultaneously
  • Shown efficacy handling diverse partners including executives, employee groups, external vendors, & consultants
  • Experience acting as a consultant to internal or external partners, with the ability to encourage action in others
  • Experience in building strong relationships that cultivate the spirit of innovation, improvement, and collaborative solutions and developments.
  • Workplace training and education; organizational development practices; and ability to use knowledge and skills to plan effective organizational interventions
  • Knowledge of Adult Learning Principles and the effectiveness of instructing methods such as classroom training, simulations, demonstrations, on-the-job training, meetings, conferences, workshops and online learning tools
  • Ability to tailor approaches to nuances of global business with offices in multiple countries

CarGurus Culture: 

At CarGurus, we invest in our people’s professional growth with everything from learning and development programs to tuition reimbursement. Want to work on projects that expand your skill set without sacrificing your work/life balance? You got it. We also strive to provide perks and benefits that employees actually care about like free lunch, commuter subsidies, and more. That includes equity in the company—our way of showing that we want you here for the long haul.

We work hard every day to build the world’s most trusted and transparent automotive marketplace, but trust and transparency don’t just apply to our consumers. They extend to our talent, too. We aim to create a workplace where everyone feels they can bring the ultimate expression of themselves and their potential—where you don’t just fit, you thrive. We don’t discriminate based on race, color, religion, national origin, age, sex, marital status, ancestry, physical or mental disability, veteran status, gender identity, or sexual orientation.

In addition to the US, CarGurus operates sites in Canada and the UK. We have offices in Cambridge, MA; Detroit, MI; Dublin, Ireland; San Francisco, CA and London, UK. Check out our careers page to learn more.

About CarGurus

At CarGurus, we believe a transparent car shopping experience is better for shoppers and sellers alike, and we innovate constantly to deliver on that promise. Today more than 20 Million (and growing) unique monthly visitors use our site and our mobile app to find their next car. With headquarters in Cambridge, MA, CarGurus has that "start-up feel"​ (we dislike meetings, play lots of foosball, have catered lunches and fun company outings—the list goes on). Unlike many start-ups, however, we have the advantage of being profitable (since 2010!) with sustained revenue growth. CarGurus is an engineering-driven company with a passion for data, and that drives everything from the speed at which we launch new products to the spirit of innovation that drives our company’s culture.

Want to learn more about CarGurus? Visit CarGurus's website.