Chip Perry & Steve Greenfield: Past, Present, & Future of Innovation in Automotive

In this special episode of Cue the Next Leader, VINCUE President Danny Zaslavsky sits down with two industry titans: Chip Perry, founder of Autotrader.com, and Steve Greenfield, former VP of Product and Business Development at Autotrader.com and current founder and General Partner of Automotive Ventures, where they talked about evolution of technology in automotive and what they see as next in inventory intelligence and operations.

Together they visited VINCUE headquarters to meet the team, learn more about our technology and operations, and advise our leadership on the past, present, and future of automotive. This episode provides a special look back at the original digital transformation that Chip and Steve shepherded into automotive, and their unique perspective on the industry landscape now and in the future.

Through his family’s dealership, Danny grew up using the very solutions that Chip and Steve had the courage and vision to create. Just like any other dealer in the country at the time, Danny’s perception of buying and selling cars was shaped by the strategies and tools these two men architected.

Now in a similar position, redefining an industry at VINCUE, Danny is grateful to count Chip as a friend and mentor, someone who constantly challenges him to stay curious and precise in every move at VINCUE. An acronym shared by Chip to Danny, DISC or “Does it sell cars,” provides the mindset behind a lot of the moves and decisions made by Danny at VINCUE.

Now think back, it’s 1997, and solutions for merchandising, syndication, and inventory management didn’t even exist yet. Chip’s idea was to help dealers simply reach the car buying public in a new way instead of advertising individual cars in newspapers, he wanted visibility for dealers’ entire lots 24/7.

Steve Greenfield, who led acquisitions at AutoTrader, helped the company bring dealers solutions they hadn’t even imagined yet, much like VINCUE today. Together, they found ways to break down silos by connecting vendors back to the core platform, building value across the entire ecosystem.

In the early days of AutoTrader, the focus wasn’t on monetization, it was on solving real problems for consumers, dealers, and OEMs through digital innovation. That product-first mindset led to a wave of acquisitions aimed at adding value, not building an empire. But as more tools flooded the market, the industry created a new problem: fragmentation. Dealers became overwhelmed by disconnected systems and redundant software.

Today, platforms like VINCUE are reversing that trend, bringing essential solutions under one roof to eliminate logins, simplify workflows, and reduce the pain of tool overload.

While the automotive industry will always be surrounded by noise and change, there’s still plenty of opportunity for “disruptors”, like VINCUE, to change and evolve the business. Steve Greenfield believes one thing has always remained true: dealers are some of the best entrepreneurs out there. They know how to spot opportunities and adapt quickly, as long as they stay focused on what they can control.

That’s exactly where VINCUE fits in. Instead of reacting to every new trend, VINCUE empowers dealers to take action in the areas that matter most: sourcing smarter, pricing more competitively, and merchandising more creatively. It’s about giving dealers control where it counts, and opening up new pockets of profitability they might not reach otherwise.

When Danny asked, “What would you say to the people who are still fighting old patterns, and how do you get them to be curious enough to understand that there is a better way forward? Steve answered in two parts.

He explained that dealers need to stay open to change, just like they eventually did with the PC, internet, and iPhone. He believes AI is the next big shift, and those who embrace it early will gain a competitive edge. Steve sees this as a chance to not only increase operational efficiency but also strategically gain market share, emphasizing that VINCUE’s close dealer collaboration and startup mindset position it well to drive this future innovation.

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