How Darren McKee Sells: Stop Hanging Out With Fellow Salespeople and Start Texting Your Buyers

Sometimes in life, to accomplish your dreams, you need a little push.

For Darren McKee, that push came in the form of his wife’s belief.

In 2017, Darren was working in operations, a steady job with a steady paycheck. But, in his heart, he really wanted to go into sales.

The problem: transitioning from operations to sales would come with a $20,000 drop in pay.

His wife, undeterred, told him to do it. So, he switched from head of operations to an entry-level salesperson, took the pay cut, and began working his way up.

It worked. Today, Darren is VP of Sales and Strategic Partnerships at Skye, and runs his own sales and LinkedIn coaching business. He also posted on LinkedIn for 1,000 days straight, and now is one of the most popular sales voices on the platform with 113,000 followers.

“If I was still in operations, I probably would’ve added another $20,000 to my salary over these past five years,” he said. “I’ve been able to add that every year since being in sales. That’s pretty special.”

Pretty special indeed, for a guy who never went to college and grew up in a small town, where his only exposure to sales was guys selling cars for more than they were worth.

Although he made this point – yeah, it’s been a good journey, but it all starts with mastering the fundamentals. So, for our How I Sell interview, we focused on the fundamentals.

Like, how does Darren make his prospecting stand out? What’s his favorite discovery question? Does he have a favorite piece of sales advice?

Here’s what he said:

1. What drives you?

What drives me most is advocating for others that have the same non-traditional path that I did.

I always knew college wasn’t going to be for me. I knew I didn’t want to go that route, but I also knew it was going to be a hell of a lot harder without it.

And so how can I be someone that says to those individuals, “Hey, there is a path. You don’t need a 4.0 GPA and to graduate from a four-year college to be successful in business. Does it help? Sure – but there definitely are other ways.”

That’s one thing that drives me. Another is I want to set up my kids for a future where they can start off running really strong at the beginning, versus having to accumulate slowly over time.

So, what can I do financially now to get them to the point where they’re 22 and they can say, “I’m going to start this great business or pursue something great and not have to raise money.”

That’s what drives me.

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

1. Increase your luck proximity.
2. Stop hanging out with salespeople.
3. No simply means not right now.

Follow up: We need to know more about one and two.

On one: This means I need to be in my buyers’ email. I need to be in their DMs. I need to have them able to see my content, I need to be at their conferences. I need to have a referrer at those events when I’m not there.

In today’s market, you’ve got to be everywhere. Because your buyers are everywhere. That’ll increase your “luck.”

On two: Salespeople don’t teach me about my buyers.

I stopped going to sales conferences and I started going to Chief Learning Officer (CLO) and talent development conferences, because those are my people. I can read a book on sales; I don’t need to spend all my time understanding what BANT means.

I need to be understanding what happens when coaching gets in the hands of the right people and how they can transform a whole business. And hanging out with sales doesn’t teach me that.

The moment I stopped taking out salespeople and instead started hanging out with my prospects was the moment I went from 50% of quota to 250%.

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

I think it goes back to the “stop hanging out with salespeople” point.

Take my LinkedIn content for example. Yes, I’m going to give back to my sales community with sales tips, because sales has given so much to me.

But a lot of my content is focused on my ICP (ideal customer profile). It’s about helping them do their jobs better.

I’ll give you an example. I just got back from a talent development conference yesterday and connected with 35 talent developers on LinkedIn I met there. Today, I posted on LinkedIn about talent development, so that’s the one of the first things they are going to see in their feed. And that’s going to help me book two or three or four meetings.

So, you just have to be a little different. LinkedIn is the greatest tool on the planet and it’s changed my life. You just have to use every facet of the platform. Everybody thinks you can just create content and get leads, but if you’re not DM-ing, if you’re not connecting, if you’re not dropping comments, it’s not going to work for you.

Speaking of LinkedIn, I’ve seen a debate on it lately that outbound is dead. This is driving me nuts because, yes, crap outbound is dead. But good outbound has never been better.

And that means researching, relevancy, personalization, a strong call to action. Humanizing yourself. I send out five to 10 video DMs every day. Everybody else is sending text-based in a world of text.

You’ve got to stand out.

4. What's your favorite discovery question?

I just say, hey, why the heck are we here?

And I just sit there. I don’t say anything and they’ll often say, “Well, you know, we did some research. We might have a need.”

I’ll respond with “What’s the need?” and we just get right into it.

Because I’ll tell you the truth, I’m not a big fan of building relationships with my buyers. My buyers aren’t there to meet with me.

They care about the problem I can solve. And, if I do that well, we are going to build a relationship through the sales cycle. And they’re going to buy from me again later when they go into another role.

I’m not going to take you for a coffee just to pitch you in two weeks. We’re going to get into it, and I’m going to try and solve your problem.

5. What's the best piece of sales advice you ever received?

There’s a bunch of things that people told me that changed my life in sales, but the top is get to text as quick as possible.

I don’t think I’ve ever closed a deal over $200,000 without texting my buyer. Ever.

I think texting my buyer right after the first discovery call is critical. And I’ll add, get in person as quick as possible. Because if you have a proposal over six-figures, you better be presenting it in person.

Follow-up: Why is texting so important and how do you do it?

The reason it’s important is it’s hard to reject someone you know. Especially if your product is good.

As far as how, in the discovery call, I’ll just ask if it’s okay if I text their cell phone number. And they always say yes; nobody ever says no.

I’ll give you an example. I had a discovery call last Thursday and I switched up a number in my head. So I just texted the person after and got clarity, and got an answer in 2 seconds. That would’ve been a day at least if it’s an email.

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

I love them all. I’m a Sales Navigator fiend.

My favorite right now is the Lead Filter ‘posted content in the past 30 days.’ That way I know they’re active on the platform and I can get them when their bubble is green or half-green.

‘Recently promoted’ is probably my second-favorite because I sell to the C-Suite. And if somebody is promoted into that role, they’re probably not getting told “no” for budget. So, I go after those people really fast.

I also used to love TeamLink because I used to work for a larger organization, where lots of people could refer me. That isn’t as relevant now, as I work for a smaller org.

Those are probably my top three. Although there is a bunch of great features.

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

Well, I have a work habit outside of work hours and I have a hobby that helps me.

For the work habit, I send most of my outreach between 9 p.m. and midnight. I don’t send it during the day. I’m normally watching NBA and they’re probably watching NBA or Bravo. Whatever they are watching, it just hits them at the right time.

So, I’ve booked almost all of my meetings between 9 p.m. and midnight.

And then, non-work, I spend most of my time on the computer. And if I’m not on my computer, I’m on my phone.

So, I spend a lot of time hunting in nature where I don’t have access to either one of those things. And that’s what really gets my brain rewired to be able to come back and do my job tomorrow.

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

I don’t know if I would call it a failure because it ended up being something beautiful, but it did probably set me back a year.

I always knew that I wanted to sell to talent development leaders and Chief Learning Officers and I had done a really good job building an entire book of business in that space. But then I got a high offer to sell in another sector, health tech.

Health tech isn’t a passion for me like talent development is. I don’t have health tech buyers. And I don’t like selling through brokers.

But I took the job and the moment I stepped foot in there – and it was nothing about the company – I just knew it wasn’t a fit. Like, it was not fun. It wasn’t something I wanted to do. And I wound up eventually going back selling into my old space.

If anybody is reading this, make sure if you switch industries that it’s an industry you are really excited about.

Because that gave me a little imposter syndrome, a bit of anxiety, and a lot of stress because I was trying to learn something new that I wasn’t passionate about. It wasn’t a fun nine months.

The good news is I was able to switch back to selling to talent developers and I haven’t looked back.

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