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How CarGurus’ “AI Forward” Is Rewiring Company Culture

Sarah Johnson

Walking through many offices today, you'll hear the same buzzwords: AI revolution, digital transformation, future of work. For most organizations, though, this excitement doesn’t always reach employees in day-to-day tasks. At CarGurus, that gap is closing fast.

In October 2024, CarGurus rolled out “AI Forward,” a 20-person cross-functional task force aiming to make artificial intelligence more accessible, relevant, and useful at every level. With representatives from product, tech, legal, sales, and more, the initiative is part innovation hub, part culture incubator—helping the company turn AI hype into everyday impact.

🎯 From Corporate Urgency to Practical Action

When Sarah Rich, a senior principal data scientist at CarGurus, began spearheading AI Forward, she saw something familiar: layers of both excitement and confusion. On one hand, executives were eager; on the other, employees didn’t always know where to begin. Sound familiar? It’s the difference between talking about AI and actually using it.

“To keep momentum, we had to meet people where they are,” Rich explained. Some employees already had ideas for using AI, others were curious but cautious, and a few thought, “This isn’t for my job.” So AI Forward tailored the support accordingly—offering everything from open ‘jam sessions’ for creative exploration to assigned, guided tasks for more structure.

🧪 Practical Programs that Empower

The initiative has fostered a diverse mix of touchpoints:

  • Office hours and collaborative jam sessions, especially for engineers exploring tools like Cursor and Windsurf.

  • A focused AI Coding Week, where developers were encouraged to adopt an AI-enhanced workflow on real tasks.

  • Workshops for non-technical teams, teaching how AI can speed up tasks like contract reviews or data analysis.

  • One-on-one coaching, where early experimenters acted as mentors to their peers.

Instead of leaving employees to flounder, AI Forward built a support structure. Think of it as a gym for AI fluency, not a one-off consulting session.

💡 The Three Stages of Adoption

According to CarGurus’ internal data, employee interaction with AI typically moves through three phases:

  1. Peak excitement – Employees are optimistic, perhaps overly so, after hearing about AI’s potential.

  2. Mid-level disappointment – Initial enthusiasm turns into frustration when tools don’t deliver instantly.

  3. Strategic utility – Gradually, people find real use-cases that enhance their work without threatening their role.

This evolution—especially when supported through group discussions and coaching—shifts sentiment from skepticism to constructive adoption.

📊 Measuring Real Success

AI Forward doesn’t just watch usage stats. It tracks:

  • Tool frequency: How often people are trying out AI.

  • Confidence levels: Whether employees feel secure in using it.

  • Sentiment: Do they view AI as helpful or threatening?

  • Efficiency gains: While useful, it's not the sole indicator. AI’s real win is creating better products or processes, not just doing things faster.

This nuanced approach acknowledges that AI is more than a productivity hack—it’s a mindset shift.

🤝 Winning Hearts and Minds

A crucial element of the program: emotional safety. When teams feel their job is secure—even as AI becomes part of their toolkit—they’re more open to exploration. Rich emphasized the importance of fostering a supportive environment.

“AI can be disruptive. If you ignore people's fears, it's tone-deaf,” she said. AI Forward has intentionally built in checkpoints to discuss challenges, share frustrations, and celebrate small wins. The result? Greater resilience and shared ownership.

🌱 What AI Forward Has Learned So Far

  • Adaptability beats one-size-fits-all: Jam sessions work well for some teams, while others prefer structured piloting.

  • Mentorship matters: Early adopters act as champions, lowering resistance among their peers.

  • Iteration is key: Let people experiment first, analyze results next, then scale the tools that worked.

  • Emotional intelligence is strategic: Supporting people emotionally is as important as tech support.

🧭 Blueprint for Other Companies

CarGurus believes this human-first, team-centered model can work beyond their walls. For other organizations looking to build momentum with AI, Sarah Rich offers clear advice:

  • Start small and inclusive. Make exploration optional, supported, and non-threatening.

  • Create space for experimentation. Whether it’s scheduled sessions or internal hackathons, people need time to learn.

  • Track more than ROI. Tool use, emotional response, and confidence are powerful indicators.

  • Prioritize support. Co-creation, mentoring, and patience matter more than flashy tech demos.

🏁 The Human Core of AI Transformation

In the end, AI Forward isn’t just about rolling out new tools—it’s about reshaping how CarGurus thinks and works. By prioritizing emotion and interaction, the initiative is proving that people—and not just technology—are at the heart of successful innovation.

The outcome? Employees are now more engaged, confident, and open to experimentation. They're not just hearing about AI—they’re applying it. They're not afraid of AI—they’re reshaping it.

When a company matches curiosity with structure, and hype with heart, transformation feels empowered—not imposed. And that's a model worth noticing.

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