This is part of our series on the inaugural inductees of the Maestro Group Hall of Fame. These twelve individuals embody the principles of true sales professionals. We recognize them for their grit, their commitment to learning, and their dedication to elevating the sales profession.
September 11, 2024
When we asked Kristina Herbst what her hardest sales experience to date was, she said, “Oh, this is so easy!” That wasn’t quite what we expected; she’s a senior sales leader at a well-respected software company with a resume some might consider intimidating. It’s also jam-packed with management experience. But Kristina’s hardest experience was her first management position. She had followed her boss and several other upper-level employees from one company to another, where she became a sales manager. “So I went on board, thinking, ‘Oh, okay, this will be pretty simple. I know the people. I’ve seen them manage. I totally know how to be a manager.’” About a month later, the board restructured, and several of the positions above her vacated. “I was told I had to run the sales team with no management experience whatsoever.”
Kristina refers to this time in her career as a “sink-or-swim type of situation.” She swam. She credits the CEO of the company, who provided her with their confidence, as well as some valuable resources on the consulting side, “but I will say there were so many times where I failed and fell so flat on my face.” She says she didn’t fully recognize what a company needed by way of quotas and KPIs in order to scale. She studied up quick. “I think it was really where I learned how to see farther in the future to be like, ‘Okay, I need to start setting up these areas to where we can grow and scale properly.’”
The sales profession had been surprising Kristina from the moment she entered it, starting with the very fact of her being a part of it. She never thought she’d be a salesperson. In college, she’d played soccer. “I put my heart and soul into it, not really thinking what I wanted to do after school. All of a sudden, graduation was coming up, and I did not go on any interviews. I didn’t really explore career options. A few of my teammates worked at this staffing firm based in Raleigh, and they said, ‘We have openings. You should apply.’” She did, and she was hired. It was through this agency that she connected with her first job in sales. “I immediately fell in love with it… It was like a game to me, and it was really exciting.”
Not only had Kristina not planned on becoming a salesperson, but she also held a number of negative ideas about the industry. “I was like, ‘I don’t want to go into sales. It’s manipulative, conniving, this and that. And then, once I actually got into it, I realized we are providing a lot of value to customers. And we’re having really interesting conversations.” She wasn’t the only one in her family who had preconceived notions about sales. Her parents imagined Kristina making cold calls at 10pm, bothering people in their homes at night. But Kristina wasn’t doing that, and they began to understand more about—and become very supportive of—her new career in B2B sales. There are, however, plenty of other people who maintain a static image in their minds of a salesperson. “The biggest misconception is, everyone thinks sales it’s like Wolf of Wall Street, and that’s not it at all.”
Although Kristina’s move from sports to sales wasn’t how she had pictured her life, she does see a lot of foundational similarities. (She’s also not the only Maestro Hall of Famer who has a sports background and connects the two fields—check out some of our other HoF blogs.) Kristina’s take on the most vital parallel? “You have to do things when you don’t want to do them. If you don’t, you’re just not going to succeed…” That and tenacity. “I think it’s because when you can stick through the bad times, and you can learn from it and get better and just persevere through it, then that’s when you see success. And that’s when you get the hunger for sales.”
She compared pitching to footwork in soccer. “You are so bad for so long. But you have to keep practicing, keep practicing, and then finally it clicks, and you get it. And you’re like, ‘Yes!’ and then, all of a sudden, you’re an elevated player.” Cold calling is no different. “You get the no, you get the no, you get the no, but because you’ve had to do this in sports, you know that you will get better, and you will get that yes, which kind of keeps driving you toward that next call, [whereas] I think people who don’t experience that, they’re like, ‘Well, this sucks. I’m out.’”
As in sports, Kristina developed her sales skillset. “I would say my start at Rybbon [which now exists as part of a digital rewards management platform called BHN Rewards] was one of the highlights where I felt like I put together a really great scalable sales model and built it out properly to the point where we could successfully exit and get acquired by another company. And I got a lot of positive feedback on how I ran the sales team, so I’d say that almost made me feel like, ‘Yes, I can do this. I may have failed in the past, but it all led to this ability of being able to do it properly.’”
Rybbon was also where Kristina met Will Fuentes and became versed in the sales techniques Maestro teaches. The categories of skills she most frequently uses and recommends are crafting—and maintaining—solid processes, running suitable discoveries and follow-ups, and asking the right questions. “Our CEO was a former CMO, so we had great marketing, and a lot of that brought inbound. But we didn’t really have an outbound sales playbook.” This was where Maestro stepped in to “help us craft the right type of messaging, making sure we’re going after the right personas and things like that.”
Kristina instantly took to Will’s methodology, as well as his personality. “He will be so candid with you.” But also motivating. “What I like about him is, if you give yourself a goal, whether you want to push toward your goal or not doesn’t matter. He will push you toward your goal until you tell him, ‘I no longer want this,’ so I think that has been really great, and I think he’s kind of done that with the rest of Maestro.”
Kristina practices what she preaches. She also preaches what she practices. In her estimation, some of the most important habits for a salesperson do not require a great deal of innate skill. For example, “having amazing process and amazing preparation takes you ninety percent of the way there. And I think so many people will sometimes miss that, but if you know how to prepare for something, if you have a process for something, and you can follow it to a T, ten percent of it is skill. Like, that’s it. The process and preparation is something I learned from Maestro, where it doesn’t matter what the situation is. Stick to your process. Have a Plan B in case you need to adapt, which is fine, but you should be doing certain things every single call.”
Her other biggest takeaway was about hard questions. “Something that really stuck out to me is, a lot of times sales reps would be like, ‘Well, I asked them if they had money or if they had budget.’ And it’s like, the way you’re asking the question will give you a canned response from your customer. Ask it in a different way to force a real response…it forces you to not have the happy ears, you can forecast more accurately. You can just get the real information from your opportunities.”
Kristina Herbst is a well of hard-won wisdom, and she’s particularly good at communicating it to those who might be newer in the field (or just want to hone their practices). Here are some highlights we wanted to share with you:
The intangibles
Be coachable; have grit; maintain a solid work ethic.
Be willing to fail
Kristina interviews well. Her first sales job she thought, “I did so great at tricking them to hire me. I don’t want to mess up. I don’t want them to regret it, so I was afraid to fail. And then, all of a sudden, all of my other colleagues who were failing…two months later, they were so much better than I was, so ever since then I was like, ‘I have got to just lay it all on the field. I can’t be afraid to mess up, because it’s the only way I’m gonna learn.’ So when I’m hiring someone I’m like, ‘You cannot be afraid to fail. Go in head first, fall on your face, that is totally fine. Now, if you do it twenty times on the same thing, that’s a problem. But learn from it, get better, and I’m not expecting you to be perfect out of the gate. I interview you so I know what I need to work with you on, and I know what you’re really good at. So go into it knowing you have things to work on.”
Have a process, and trust the process
Before she established a concrete process, Kristina would meander during sales calls, “I would go here, and then I would go here, and then I would go here. But now I have the structure, and I can double down on areas that I need to double down on.”
Take people up on their offers!
“Networking is so important,” says Kristina, but she’s noticed that oftentimes people fail to accept genuine offers for help or guidance. “At least what I’ve seen is people just don’t take other people up on it. I don’t see a lack of people willing to be a mentor or willing to be part of someone’s network. What I do see a lack of is someone continuing to follow up with someone on that. I can’t tell you how many times I offer someone, ‘Hey, put time on my calendar anytime you want. I’m willing to talk to you. We can talk through something,’ all the time. Will does the same thing with people that he works with.”
Kristina emphasizes that you don’t need to have an agenda in order to chat. “Just start a conversation and continue following up. And if you don’t know what to talk about, that’s totally fine, just talk about random things, and then eventually, you’ll start finding things in common, things to talk about, like strategizing. But I think people just don’t do it.”
Why? Kristina blames the networking hype. “I think people have just built it up to be something so formal, but it’s not. It’s like you’re meeting friends, but you just have the benefit of providing value to each other based on your work.” She does acknowledge that Zoom makes things feel more official, “so that part may be a little tricky, but even if you just talk about an icebreaker or something for the first five, ten minutes, or get on a texting basis, so it’s less formal—there are ways that you can make it feel less [formal.]”
Kristina continues seeking input from others and encourages her network to do the same. If you need to talk something out, put time on her calendar. She means it!
Kristina is currently an Area Sales Director at Okta, the leading independent identity partner for businesses worldwide. You can learn more about Kristina here. Be sure to congratulate her while you’re there!
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