January 19, 2023
For this episode, John and I talk to our friend (and former teammate of JR’s) Brian Kolb. Brian works as a Senior Account Executive at Tidelift, a company focused on helping application development leaders take advantage of open source software so that it works better for everyone. We cover a lot in this podcast, and raises one key concept that is worth zeroing in on in more detail here.
As is always the case with a Merchants of Change podcast, our conversation with Brian covered a lot of ground, from our shared history at Holy Cross to how Brian broke into tech sales to what makes him successful today to his aspirations to take on more of a leadership role.
We’re at the end of a calendar year (though we still have a few more pod eps in S2 of Merchants of Change so stay tuned!) and there’s a natural tendency to look back on things, to reflect, and to use what we see to influence how we move forward. To adjust, to improve, to do more of, to do less of—it’s so much like sitting down and watching film. And something came up in this conversation again and again, something that we heard in some way or another in other episodes—though not to the extent that we heard it here. In this conversation, it was more of a theme, and I think it’s a really important thing to focus on. You can listen to the podcast to hear everything Brian has to say, but I’m going to keep the focus here ultra-sharp and dial in on the importance of authenticity.
In several episodes past (and this one was no exception) our guests have either alluded to or explicitly stated how important it is to find people who do the things you want to do and then to emulate them. This takes many forms. It may be that you see someone with a lifestyle you admire, and that’s what drew you into tech sales in the first place. It may be the traits and behaviors you see in people closing deals and achieving financial success. It may be more of a social thing, when you see people building and leveraging strong networks. Or it may be seeing styles and behaviors and characteristics and traits you want to avoid.
(Side note here if you’re looking/hoping for remote work: when you’re starting out in tech sales, being in an office surrounded by people focused on selling your company’s product(s) is an invaluable experience. You really will learn “by osmosis.” Listening and watching in 3D will teach you more than any Zoom or Teams meeting ever will. Being in person, being watched and seen, may help you learn to be more accountable, and it may help you avoid subconsciously and unknowingly developing bad habits. Find the right company for you, which may mean you have to be in person at first but that you’ll have the opportunity to “earn” flexibility. It’s worth considering. Don’t rule a job out solely on the grounds of whether it is in person, hybrid, or fully remote.)
While it is important to model yourself after the behaviors you admire, it’s critical that you find your own style and your own voice. Align yourself closely with your AEs. Work on communicating with them and building a partnership. Take deals as far as you can for them—pay attention to what works and what doesn’t work. Adjust and try again. This will help you uncover your best sales self.
Making your pitch in your “best sportscaster voice” won’t make you any more credible than someone who’s “on the level.” It’s far more important to show that you know your product, that you understand the customer’s needs, that you can demonstrate how your product will help them, and that they trust that you will act as a true partner. Sales is hard. If you’re spending precious time and energy on being something you’re not, you’re taking time away from the value-added activities that can have the most impact on single deals and on long-term relationships with customers. When you know your stuff, when you know who you are, and when you have a genuine interest in solving customers’ problems, doing the hard work you’re used to as a former athlete will feel more relaxed and more natural. Then, when the opportunities present themselves, you’ll be much better prepared to take advantage of them. Don’t waste time doing stuff that doesn’t add value—don’t waste time being an impostor.
As you develop and as your career progresses, you’ll be the one people are watching. You’ll be the one demonstrating those admirable behaviors and traits, and you’ll be the one acting in a way that engages and excites and motivates others. You’ll be the one defining the future for who knows how many athletes who are looking to succeed in tech sales. That would be pretty awesome, wouldn’t it be?
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