Leadership in the Dealership

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Aug 2026

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About the show

Welcome to Leadership in the Dealership — an Upstart podcast where automotive innovation meets insightful conversations. We help dealers improve their customer and employee experience by tapping into the minds and experiences of the industry’s top leaders. We’ll also explore cutting-edge trends shaping the auto industry across digitization and customer experience, both online and in the showroom. Ready to meet your hosts and catch a sneak peek of what's to come? Check out the trailer. The views, thoughts, and opinions expressed in this podcast are those of the hosts and guests and do not necessarily reflect the official policy or position of Upstart. Any content provided by the hosts or guests is for informational purposes only and is based on their own experiences and perspectives.

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60 recent

August 19, 2026Episode 6220 min

Too much tech? How to Audit Your Dealership Tech Stack

How do you know if your dealership has too many technology platforms?If your team is re-entering the same customer information into multiple systems, chasing data across disconnected tools or paying for platforms that overlap, your tech stack may be creating more work than it solves. Danielle Mills Walden and Phillip Greer break down how dealerships can take a closer look at the systems they already have before adding the next shiny tool.They get into CRM hygiene, integrations, F&I, digital retail, AI and why a tool can be great on its own but still create friction if it does not communicate with the rest of your stack. They also discuss why AI should be layered onto clean processes and reliable data, not used as a shortcut around broken ones. In this conversation: How to audit your dealership tech stack Why data re-entry is a sign your systems are not working together How disconnected tools can cost your team time and money What to ask vendors before adding new technology Why CRM data quality matters When AI actually belongs in your dealership workflow How to spot duplicate tools before you pay for another one Before you add another platform, make sure you know what your current stack is actually doing for you. Subscribe for more real conversations about dealership operations, technology and leadership from Leadership in the Dealership. #Automotive #CarDealers #DealershipTechnology #CRM #ArtificialIntelligence

August 5, 202626 min

When Something Goes Wrong, Everything Matters

Every dealership has problems. A delivery gets delayed. A repair takes longer than expected. Financing changes. A customer leaves frustrated. The dealerships customers remember are not the ones that avoid those moments. They're the ones that know how to recover from them. In this episode of Leadership in the Dealership, Danielle Mills Walden and Phillip Greer break down what great customer recovery actually looks like. Through real stories and firsthand experiences, they discuss why communication, transparency and follow-through often matter more than getting everything right the first time. They cover: • Why customer recovery starts before the complaint • How simple communication can prevent negative reviews • What dealers can learn from Carvana's customer experience • Why giving customers options builds trust • The mistakes that turn small problems into lost customers • How transparency creates long-term loyalty No dealership gets it right every time. The difference is what happens next. 👇 Subscribe for more conversations that help you build a better dealership. #Automotive #CarDealers #CustomerExperience #DealershipLeadership #LeadershipInTheDealership

July 22, 202619 min

TikTok Is the New Car Salesperson

Who's Influencing Your Customers First? Most buyers don't start their car search at a dealership anymore. They're spending hours on TikTok learning what to ask, what to avoid and how to negotiate before they ever step onto your lot. Danielle Mills Walden and Phillip Greer break down why social media has become one of the biggest influences on the car-buying journey, and what dealerships can do to stay part of the conversation. The stores earning trust today aren't just waiting for customers to find them. They're showing up where customers are already looking. You'll learn: Why TikTok has become a search engine for car buyers How Gen Z researches dealerships before visiting Why dealer-created content matters more than polished ads How transparency impacts your online reputation Practical ways dealerships can connect with today's buyers Whether you're a dealer principal, general manager, sales leader or marketer, this conversation offers practical strategies for earning trust in a world where customers are more informed than ever. 👍 Like this video if you enjoyed it. 🔔 Subscribe for new episodes of Leadership in the Dealership every week. #LeadershipInTheDealership #Automotive #CarSales #Dealership #AutoRetail #TikTokMarketing #GenZ #DigitalMarketing

July 8, 202619 min

More Profit or More Sales? What Actually Wins?

Every dealership wants to make more money. But is the smartest move maximizing profit on every deal or moving more inventory? In this episode of Leadership in the Dealership, Danielle Mills Walden and Phillip Greer break down the strategy behind gross versus volume and why the best operators know when to switch between the two. They discuss: • When it makes sense to maximize gross • When volume becomes the smarter play • How inventory and OEM incentives should shape your strategy • Why holding out for more profit can sometimes cost you money • How affordability is changing the way dealerships buy and sell inventory • What today's market means for both dealers and car buyers The best strategy isn't picking one side. It's knowing when the market tells you to change. 👍 Like, subscribe and let us know in the comments: Are you Team Gross or Team Volume? #LeadershipInTheDealership #Dealership #Automotive #AutoRetail #CarSales #FandI #DealerStrategy

June 24, 202615 min

The Motor Oil Supply Risk You Should Be Watching

Everyone is talking about gas prices. But what if the bigger risk is motor oil? In this episode of Leadership in the Dealership, Danielle Mills Walden and Phillip Greer discuss how global supply disruptions could impact synthetic oil, service departments and the products dealers rely on every day. They get into: • Why motor oil and gas prices are not the same conversation • How supply disruptions can impact service departments • What dealers should be doing now to prepare • Why fixed ops may feel the effects before anyone else • How to communicate with customers during periods of uncertainty • What service leaders should be watching in the months ahead This isn't a prediction about where gas prices go next. It's a conversation about preparedness. Because when a key service-lane product becomes harder or more expensive to source, the dealers who plan ahead will be in a much better position than the ones reacting later. 🎧 Like, subscribe and let us know what topics you'd like us to cover next. #LeadershipInTheDealership #Automotive #Dealership #FixedOps #ServiceDepartment #AutoRetail #Cars #MotorOil #AutomotiveIndustry

June 10, 2026Episode 5723 min

2.4 Million Lease Returns Are Coming. Now What?

Not every lease return is a problem. In fact, some dealers are hoping those vehicles come back. Low-mileage, well-maintained lease returns can be some of the most attractive used vehicles on the lot. The challenge is what happens when millions of them hit the market at the same time. In the latest episode of Leadership in the Dealership, Danielle Mills Walden and Phillip Greer break down what dealers should be thinking about as lease returns continue to rise, how EV leases factor into the equation, and why structure matters just as much as credit when it comes to getting deals done. "The problem wasn't the buyer. The problem was the structure." The dealers preparing for this shift now will have more options when those vehicles start showing up.

June 10, 2026Episode 5628 min

The Future of Car Buying Isn’t One Offer

Most dealerships still structure deals around a single approval and a single offer. But customers don’t shop that way anymore. In this episode of Leadership in the Dealership, Danielle Mills Walden and Phillip Greer sit down with Ben Atkinson, VP of Auto Lending at Upstart, to break down why multi-offer financing is changing the dealership experience and what it means for dealers moving forward. They get into: • Why “single-single” financing feels outdated • How multi-offer lending creates more flexibility • Why choice changes the customer experience • The trust problem still hurting dealerships today • How AI and modern lending tools are reshaping approvals • Why the future is about working with the customer, not against them Because at the end of the day, “the customer and the dealer should feel like they’re working together. The dealers adapting to this shift are already closing more deals.

May 13, 2026Episode 5536 min

From $198 to $1,000… Why Does Everything Feel So Expensive Right Now?

In 2016, you could lease a vehicle for under $200 a month. Today, that same payment is pushing $1,000. And it’s not just one thing driving it. Inventory is stacking. Tariffs are quietly working their way into costs. Gas prices have jumped fast. And OEMs are still reacting to where the market was, not where it’s going. Your customers are feeling all of it. They’re hesitating more. Looking harder at used. Taking longer to make decisions. “People are hesitating in ways they didn’t before.” In this episode of Leadership in the Dealership, Danielle Mills Walden and Phillip Greer break down how these forces are colliding and what it means for how deals are getting done right now. Because this isn’t just about higher prices. It’s about how those prices are changing behavior at the desk. Catch it early, or you’ll feel it in your deals.

April 29, 2026Episode 5424 min

Stop Using AI Like This (Start Winning More Deals)

Most dealerships are already using AI in their CRM. But they’re using it to do more of the same thing, faster. More follow-ups. More templates. More “just checking in” emails. And customers can tell. In this episode of Leadership in the Dealership, Danielle Mills Walden and Phillip Greer break down where AI follow-up goes wrong and how dealers are actually using it to improve communication, not just automate it. They get into: • Why most CRM emails feel generic • How to use AI without sounding like AI • The “be me, but better” approach to communication • Where automation helps and where it hurts • How AI can improve speed without killing authenticity • How it’s changing F&I, lending and approvals “If you’re not contacting them well, they’re not telling their friends about you.” This isn’t about using more AI. It’s about using it where it actually works. Stop being "that guy" at the airport talking to his phone like a crazy person and start winning at the dealership. Here is how to use the "AI touch" to get them in the door without sounding like a robot.

April 15, 2026Episode 5318 min

Why Trade-Ins Are Killing Your Deals (And What Dealers Are Missing)

The trade-in process is slowing deals down and costing dealerships opportunities they should be closing. This episode breaks down the math, the friction and what dealers can do to improve the process. Phillip Greer and Danielle Mills Walden unpack why trade-ins have become one of the most challenging parts of the modern car deal and how dealerships can approach them differently. In this episode: • The impact of negative equity and how it shows up in today’s deals • How instant appraisal models are reshaping customer expectations • The cost of longer deal times and what it means for the customer experience • Why incremental improvements can drive better results • Why experience matters more than ever in the dealership process Connect: Website: www.leadershipinthedealership.ai LinkedIn: Danielle Mills Walden LinkedIn: Phillip Greer #dealership #automotive #autoretail #cardealer This podcast is powered by Upstart.