Episode 5: Strengths in Fundamentals | Rocky Paap

Tune in to this week’s episode of Merchants of Change to hear a seasoned sales executive’s take on what makes someone a true sales pro. Rocky’s measured and systematic approach can teach us all something. Read on to get JR’s takeaways on the convo. The podcast is #recommendedlistening. And the blog is #recommendedreading.

After we record a podcast, I come away so energized. There’s always a new great line, a new take, a new perspective.

In this case it was when I asked Rocky about his favorite sports memory and he reported that it was when his Colt baseball team was one out away from the league World Series and lost the game in classic “bottom of the 9th” breakdown fashion. He admits it’s not a “great” memory, but the lessons he took away from it are invaluable. It made me think about the word “favorite” differently. I can ask one person what their favorite sports memory is and maybe they’ll talk of a big comeback, a big play, a perfect season, or off-the-charts team chemistry. Rocky talking about a loss was not what I was expecting. A “favorite” sports memory doesn’t have to involve an amazing victory, a realization that highlights one of the great connections between sports and tech sales—sports teaches you to learn to lose, to be resilient. Tech sales is the same.

Rocky answered several questions differently than I was expecting which got me to thinking about how differences play out when someone is shifting to sales. Because everyone is different, the system that works for one person might be a total disaster for someone else.

I’m here to tell you that’s ok, and that Shift Group is here to help.

Despite these differences, there’s a similarity in approach that benefits everyone, and I think if you’re starting out in tech sales you need to do two things:

  1. Find someone you respect/admire/want to be like and emulate them
  2. Find your unique voice so you become an authentic partner to your colleagues and customers

#2 above is going to be really difficult if you don’t find a role that’s the right fit for you. In general, when you’re assessing a role, things we encourage you to consider are the technology you’ll be selling, the total market size, the company culture, your manager, and career progression, to name a few. When you have multiple opportunities in front of you, evaluating them can be tricky and it’s important to assess them relative to the parameters that are important to you.

In general, we—and our MoC guests—advise that no opportunity be summarily dismissed and that every opportunity be given due consideration. Other considerations when weighing offers beyond what I just mentioned are compensation and one that’s recently become part of the conversation—whether the role is remote, hybrid, or in-person. I know many of you think you want a remote role. But as someone who derived tons of value from working on a sales floor, I’m a big fan of in-person roles. I get that everyone’s different and times change, but I also think that being in an office in the same space as the rest of your team when you’re starting out provides three huge advantages:

  1. In-person training/engagement. When everyone’s together, it’s easy for everyone to collaborate. Discussions and problem solving tend to evolve more organically. Not to mention it’s easier for people to see you hustling.
  2. Learning by osmosis. When you are around people doing what you’re doing or doing what you want to be doing, the value you get from watching them in action is immeasurable and likely will accelerate you finding your voice.
  3. Easy access to resources. It’s so easy to ask questions when someone’s right in front of you. The more questions you can ask, the more you can learn, quicker. This also will help you accelerate finding your voice.

Everyone is different but I’m here encouraging you not to be short-sighted on this single parameter and to consider it in totality when you’ve got multiple offers. Do not rule an opportunity in or out simply because they let you work wherever you want to. In sales, you’ll typically earn this right over time. Starting in an office might help you get there faster. Maybe it won’t. I’m asking you to consider it. All factors should be considered because if you are working from home trying to sell a product you don’t fully understand to a really niche market and you have a bad manager and no team to collaborate with, how happy will you be?

Tune in to the podcast to get Rocky’s tips on starting and sustaining an impressive tech sales career. Reach out to me if you want to talk about my thoughts here or how Shift Group can help you.

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