TL;DR
- Karsten Chearis leads one of Expel’s solutions architecture teams, after a career that started in IT and security operations on the customer side.
- A single question from a recruiter moved him into sales engineering, and he hasn’t looked back.
- He once sold T-shirts to Birdman, and he’s confident he could talk 47,300 pigeons into carrying him.
Karsten Chearis will tell you he lives in Memphis, but that it’s more accurate to say he’s from the 901.
The area code covers more than the city, and Memphis pulls in people from all the small towns around it. Karsten’s hometown is one of them: a spot out in the country with, by his count, “A tree, the church I grew up attending, my mom’s house, and a Sonic.”
From the customer side to the sales side
Karsten started his career on the customer side, doing IT operations, which turned into security operations, like break-fixes, spinning up servers, Active Directory, and “all that stuff.”
Part of the job was buying tools. One of his first big purchases was Microsoft Intune, because his team needed a way to secure their endpoints, including mobile devices. He talked to their partner rep, ran a proof of value, and worked through the purchase with his manager. To him, that was just part of making his job easier.
Then a recruiter reached out about a sales engineer opening at an email security company.
“I said, what’s a sales engineer?” Karsten says. The recruiter explained that they’re the ones who do the tech stuff when you buy things. Karsten pushed back. His only sales experience was retail at JCPenney, and his picture of sales was a sleazy car salesman who didn’t really care about the customer.
So the recruiter asked him one question: “Have you ever had a problem and you knew the exact solution, but you had to convince other people that that was the solution?”
Yes, Karsten said.
“Welcome to sales.”
That question changed his whole career trajectory. Every time he’d spotted manual work and pitched a way to automate or standardize it, he’d been selling. “It’s a humble position of hearing someone having an issue, having a problem, and you know how to help them,” he says. “You’re bridging a gap between their needs and what you know.”
He crushed the interview. (Editor’s note: Karsten has the charisma required to sell sand at the beach, so there is absolutely no way this is even a little bit exaggerated.) Since then, he’s been an individual contributor, a leader, and now, a leader of leaders.
Why solutions architecture
Karsten’s favorite part of the work is that solutions architects get to talk with customers and understand what they’re up against.
“A lot of us, we did the work,” he says. “We know what it’s like to have to fight these attacks and not have the best software and partners to do it.”
He came to Expel through Kim Mahoney, a former colleague. The two had worked together, gone separate ways, and kept looking for a chance to team up again. When an opening came up on the solutions architecture leadership team, she referred him.
Now he leads one of those teams. He calls them “a group of beasts.” They’re smart and funny, and they keep him on his toes. “The people here are my favorite part about being at Expel.”
A bunch of nerds at the same table
Ask Karsten what people might not know about Expel and he starts with the people. (Editor’s note: If you’ve read any of the Meet the Expletive blogs, you definitely already know this, but we’ll give him a pass.)
“We have some of the smartest bunch of nerds I have ever seen in my life,” he says. “And I mean that in a loving way. We’re not just smart, but we are nerds about this. Like, no, that’s not the way to do it. This is how you do it.”
He’s also struck by how little ego comes with it. “No one has this attitude of, don’t talk to me, I’m a founder. Don’t talk to me, I’m a senior director,” he says. “Our founders are approachable. Our founders will joke with you, and they can take a joke.”
His way of putting it: “Even though we have a hierarchy and we have levels, we sit at the same table, and no chair is bigger than the others.”
The troll chat
Expel’s Zoom chat during company calls is affectionately referred to as the troll chat, where trolling is invited and, according to host Ben Baker, encouraged. Karsten is one of its regulars.
His self-described superpower is making you cry laughing exactly when you’re supposed to be serious. “God forbid we ever know the same person and we’re at a funeral,” he says. “Do not sit by me.”
His secret is that he’s saying what everyone is already thinking. “No one just hasn’t had the courage to say it yet.” (For the record, he’d like everyone to know he’s not breaking any HR rules.)
There’s a philosophy under the jokes. “There are things in life where you have to pay the tax of tears. There is a time to mourn,” he says. “For those other times, why be sad? One minute of you being upset, you just robbed yourself of 60 seconds of happiness.”
If he can put a smile on someone’s face during a Zoom meeting, he counts that as a job well done.
Fun facts and very important questions
Karsten has seen his share of celebrities. Years ago, Mike Tyson had a fight in Memphis, and he was working at the mall when the city filled up. He saw Wesley Snipes, several Cash Money rappers, and cast members from Soul Food.
He also sold T-shirts to Birdman, back when big white tees were in. Birdman’s one request was, obviously, to make sure Karsten scanned his coupon. Karsten chuckled as he recalled thinking, “You have all this money and you’re talking about a coupon at JCPenney?”
People are often surprised to learn he’s an introvert. People tell him he’s easy to talk to, and he is. But being around people drains him, and after a while he needs time to recharge by himself.
Because of Karsten’s infectious energy and humor, we had to ask him not one, not two, but three very important questions.
His first question to answer was if all animals were the same size, which would win in a fight? Karsten checked that insects count, then picked ants. “Ants are one of those insects that people literally step over and step on. The only time you really pay attention to them is when it’s a bunch of them. That’s when you feel the sting.” Full-size ants, in his view, would finally get their revenge.
Next, we asked: You just joined the Spice Girls. What’s your Spice name? He considered Baldy Spice but ultimately went with Red Velvet Spice, after his favorite cake. “Even though it’s spicy, there’s some sweetness to the Spice Girls.” And he said Baldy Spice was too obvious.
We thought we stumped him with this final question, but he didn’t even pause when we asked him, on an average day, how many pigeons could you reasonably carry? This is where Karsten got a little sappy. Growing up, he stuttered. His mind moved faster than his mouth would let him talk, and he got picked on for it. So he read the dictionary every day to build his vocabulary. He had a goal: “To communicate in such a way where even if people don’t agree with me, they have no choice but to listen and respect my opinion.”
So then he naturally flipped the question and asked how many pigeons he could convince to carry him. Given enough prep time, he figures he could persuade them he’s worth it (and for the sake of his argument, the pigeons do understand English). His estimate is 47,300 pigeons. “I did some math in my head. Don’t worry about it.”
You can catch Karsten on our next democast—sign up here to get great laughs (and better security advice).
