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Sales Leader Interview Series – Dan Dionne

Leading a Team Through a Crisis

Dan Dionne is currently the Director of Sales at CarGurus, where he has held numerous sales management roles over the last six years. Prior to joining CarGurus, Dan spent three years as a buyer at Brookstone in some of the company’s largest product sectors. 

We sat down with Dan to discuss the pandemic from both a sales rep and managerial perspective, and got some great anecdotes on email automation and sales coaching.

How do you recommend that sales managers get the most out of their one-on-one meetings in a remote environment?

When it comes to managing remote reps, one of the new challenges that has arisen is holding people accountable to their goals. The one-on-one conversations that we used to have face-to-face are a lot different when you are on the phone. On top of that, you now have to schedule time to hold those conversations. One way of adapting to this situation is through notetaking and follow-up emails. Take notes on those conversations and put them in your follow-up emails, so that when you come to your next one-on-one or coaching conversation, you can bring up the email and really check if they’ve accomplished everything that they wanted to. 

What advice do you have for reps suddenly having to sell through a crisis?

Just take it day-by-day. I think when the pandemic started, everyone hit the panic button, and basically said, “all right, it’s getting harder to sell, how am I going to hit my quota?” Just focus on making the first connection, and worry about the quota another time. 

I think regardless of the situation or what’s stacked up against you, reverse engineer your goals. How many calls do you have to make to schedule a demo? How many demos do you need to secure a deal? Stick to the basics. Everyone always looks to those big homerun deals to reach their quota in one deal. You have to remember that 20 nickels still make one dollar, so if you have to get 20 deals, then you have to get 20 deals. 

Another thing is when you’re face-to-face you can really read somebody or grade how good of a salesperson they are. That’s changed completely. At least for the next two or three years we’re going to need to figure out how to read someone through a screen, rather than reading someone who’s sitting six feet in front of you.

What is one of the more interesting prospecting methods you’ve seen work?

I’ve seen reps email their entire contact book with a blank email, which then got more responses than any in-depth email—which is insane. They’ll get a response that says, “Hey, this was blank.” Then they call back and say, “Sorry about that, I forgot to put what I was going to tell you”, and all of a sudden they are in a demonstration. It’s an amazing thing that I’ve seen happen. I like mass communication because you never know what you’re going to get out of it. 

What do you wish you knew about sales coaching when you first started leading a team?

I think coaching all comes down to listening and notetaking. These simple, basic things that we all think are just normal day-to-day activities are some of the more important things that we can do as coaches. But you need to listen first before you can do anything. You can’t assume you know what their problem is. You have to listen first, and then react. 

Coaching isn’t just walking around, asking what deals are coming in. When I worked in a start-up environment deals were coming in so fast. Now, coaching is having your reps bring their top five deals and spending 30 minutes talking to them about those deals and the best strategies.

Thanks, Dan, for the great insight and advice! Stay tuned next week for another post in our Sales Leader Interview Series, and check out the BuyerSight Blog for more great interviews with other leading sales experts.

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