How Jake Dunlap Sells: Live in the Gaps and Become “Buddies” With AI

Paul Petrone

Breaking through the noise with relevant, insights-based content.

May 13, 2024

How Jake Dunlap Sells: Live in the Gaps and Become “Buddies” With AI

Jake Dunlap started selling in college. Telemarketing, specifically, selling vacation packages over the phone.

He took the job because it paid well. But as he got into it, he found out two things about himself:

Unlike most people, he wasn’t bothered by the rejection that comes with sales. “I never took it personally,” Jake said. “I just saw it as another data point.”
More importantly, he found sales fascinating.

After graduation, he took a job selling season tickets for the Tampa Bay Rays baseball team. There, he met an older salesperson who suggested he start reading sales books.

He did. That’s when his fascination about sales turned into a calling.

“I started reading these sales books and I was, man, this is so much more of an art and a science than I originally thought,” Jake said. “And as sales has continued to evolve, it just continues to get more exciting, candidly. I just don’t ever get tired of it.”

It shows. Jake has spent his whole career in sales. Since 2012 he’s run his own sales consulting business, Skaled. And, in April, he published his first sales book, “The Innovative Seller: Keeping Pace in an AI and Customer-Centric World.”

In our ‘How I Sell’ interview with Jake that passion shone through, as he spoke on everything from how the industry is changing to his favorite discovery question to how he’s using AI to transform his own sales process. Let’s dive in:

1. What drives you?

What drives me now is I’m very adamant and excited about where sales is headed. Right now, I believe there’s a clear line-of-sight where we can take sales to meet customers where they are more effectively.

That might sound like a business-y answer, but I truly do love sales. And not what I imagine most people think is sales, but instead what I believe sales really is. Which is helping people make a decision, whether it’s to work with you or not, and to consult them and understand their business and have empathy about where they are.

I think customer behavior is changing a lot. And I’m driven by what’s next. I’m driven by being a voice to get people to that next step.

2. What's your sales philosophy, in three sentences or less?

Sales is about helping a customer make the best decision for their business. Hopefully, that decision is to work with us, if there is a strategic need. But, if not, it’s to help them get on the right path and consult them on trends in the marketplace.

3. How can sellers today make their prospecting stand out?

The most beautiful part is the bar is lower than ever. Especially when it comes to email or InMail messaging.

I’ll use myself as an example. I get sales emails all the time. Do you know the amount of those that actually show that the salesperson understands what a CEO of a professional services business does and is going through?

I’d say maybe one or two a quarter. Most of the time, at best, I’ll get “I saw you got your MBA from Arizona State, go Devils.”

Executives take meetings with people that make them smarter. If you can't even demonstrate a basic understanding of my job, I won't consider taking a meeting with you.

So, I think the bar is lower than ever. If you just take the time to write out the trends in their space – or get Chat GPT to show you what the trends in the space are – and show them where the puck is going and how you can help them get there, you’ll get meetings.

And you need to be specific. It isn’t enough to know what the challenges of a VP of operations in manufacturing are, for example. Because the challenges of a VP of operations in industrial manufacturing are far different than the challenges of a VP of operations in consumer packaged goods manufacturing.

Again, Chat GPT can help here. Ask it what the challenges are in that specific industry.

Point is, if you show people that you understand their day-to-day and you understand their challenges, you will cut through the noise. And you will win.

4. What's your favorite discovery question?

What are the top two or three priorities for your business over the next two quarters?

This is the one I enjoy teaching the most because it immediately has an impact. I’ve had people come up to me after I teach it and say that one question has helped them so much.

Here’s why it works. You can’t ask a senior executive their top goals or priorities for the year. Many won’t even know where to start. The human brain struggles with that question.

It’s similar to if I were to ask you what you’re up to in June. That’s not easy to answer. But, if I ask you what are the top two things you’re most excited about in June, I bet your mind has a specific answer.

So, by asking the discovery question with a specific number over a specific timeframe, you get a much more targeted answer. And then, by starting with the business priorities, you’re able to have a much more strategic conversation, versus what most people start with.

Then, once I understand the priorities, I need to find the gap. But sometimes people won’t feel a gap; they think everything is good.

I can’t sell if they don’t feel a gap. So, in that situation, I’ll ask if I can circle back in 30-45 days, if some of these problems start to occur. And I pick problems that are very likely to happen based on my experience, as then that gap will start to reveal itself.

If they are already feeling a gap or know that something isn’t as strong as they’d like it to be, now we can have a real conversation. Because that’s what sales is, it’s filling that gap.

5. How should sellers be using AI?

From all my learning, what I’ve realized is it’s not thinking, “What’s our Generative AI strategy?” A better way for everyone to think about it is – “What is my typical, day-to-day workflow, and where can GAI add incremental value?”

And, the fastest and first part that every seller should look at is preparation and research.

I can ask Chat GPT, “I have a meeting coming up with (this company). Here’s the products that we sell (insert copy from our product page), here’s the person I’m selling to (copy-and-paste their LinkedIn profile). Based on that, build a discovery call prep sheet that helps me quickly identify the top three trends for companies in that space and where we might be able to help.”

In three seconds, you have your discovery call prep.

Or, “Here’s this company’s annual report (upload annual report). Where are the biggest opportunities for us based on the products we sell?”

Bottom line, Generative AI can be your co-pilot. It can save you hours and hours a week, especially if you work in mid-market or enterprise sales, in research alone.

That’s where I recommend everyone start. And then a bonus use-case is for your own training and development, as you can use it to get up-to-speed on any persona or industry.

For example, I can have it create a 15-question trivia game that’ll make me smarter on having conversations with CFOs in consumer packaged goods. Or, the same prompt but for mid-market private manufacturing companies.

You can use it to start training yourself, right there.

As you use it more and more, you’ll start to see how it can fit more and more into your workflows. And know it’s only going to get better.

So, I see it as a buddy, or an on-demand thought partner that’s going to foundationally change how we solve problems. And that’s where the have and have-nots are going to start to really pop up; with the haves being the people who retrain their brain to start using it in how they approach their work.

6. What's your favorite Sales Navigator feature? Why?

My favorite Sales Navigator feature is Lead Alerts, specifically Lead Shares.

For context, this feature alerts you every time one of your leads shares content on LinkedIn. Because what I found is that you’d be shocked at the amount of people who get no comments on their LinkedIn shares.

If you just comment on somebody’s LinkedIn posts twice, they will remember you. It’s just spending five minutes every morning and going through all of those lead shares and commenting to start building a little relationship capital.

What I love about it is it allows reps to interact authentically with people. And it provides real reasons for reps to reach out and for leads to want to meet with you.

My second favorite feature in Sales Navigator is the search filter “Changed Jobs in the Last 90 Days.” And that’s because no one has ever brought in a new executive and told them, “Change nothing. We just fired the last person, but we want you to come in and change nothing about the place.”

Almost always, new hires are looking for new solutions, new vendors, new processes. That’s another cheat code for salespeople and honestly a bit of a no-brainer.

7. Do you have a habit outside of work that helps you perform better?

I made a commitment last year that I was going to close my rings every day on my Apple Watch.

Now, I lost my watch for three days in Costa Rica in the water – probably shouldn’t have had it in the water to begin with, but so is life – and I missed those three days. Aside from that, I’ve been very consistent.

It’s really the first time in my life I’ve had a regular workout or movement routine. And I think if you’d ask my staff over the past year-and-a-half, they’d say I have more energy and have consistently shown up better. And I’ve slept better.

So, I think working out every day and having this accountability buddy called the Apple Watch has really helped me.

8. What was your biggest failure in sales, and how did that experience transform you?

This is the God’s honest truth, but I don’t see things as failures or successes. I see them all as data points.

If something worked out, I try to learn why it worked out. If something didn’t work out, I try to learn why it didn’t work out. It’s all a process that helps me improve over time.

Follow-up: What was your biggest data point?

Well, I have data points on both sides, but the biggest data point on the other end of the spectrum I’d say is patience.

In sales, you always feel like you’re under the gun. And I think early in my career I was too hard on people because I was feeling pressure and was putting it on them. As I grew, I realized I’m supposed to take that pressure – be a pressure sponge, of sorts – and keep it away from my people.

So it’s really just patience, particularly when it comes to leadership. Good things take time and sometimes you have to have patience and know that things are going to work out.

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