Want a Thriving Sales Career? Focus on This
Resources to identify what's right for you in different stages of your career
I recently listened to an episode of Cloud Radio, hosted by Matt Harney. In the episode, he sits down with Ryan Walsh, CEO of RepVue. They discuss many topics, ranging from tough interview questions, due diligence, quota attainment, market conditions, and career advice. I’d recommend giving it a listen or checking out Matt’s substack: SaaSLetter.
One of the key takeaways from this episode, among many, was understanding where you are in your career and what’s going to be a fit. Before even looking for a company to work for you should have clear understanding of this.
Questions to Ask about Your Next Role
Sam Marelich, Founder of Next Venture, posed this question on twitter:
I don’t think that it’s a bad idea to strive for the ideal role with all the perks. However, like anything in life, there’s always a give and get. I particularly like this thought process because it helps you to critically think about where you want to go in your career versus passively chasing OTE.
What’s important for YOU?
Do I want to be making x amount of cold calls per year?
Do I need structure and heavy sales enablement support?
Do I want to sell a highly technical product?
These were questions that Ryan was asking during the podcast. They’re great baselines of how to formulate where you want to go. You can layer more of these questions into:
Do I want to sell for a startup or a bigger tech company?
Do I want a well known logo or that doesn’t matter?
Does the sales team have a playbook or do I have to build one and figure it out?
Digging further, what’s your personal situation and how does that play into the next role?
Financial stability?
Remote/Flexiblity?
Benefits?
Deal Size and ACV?
Is it feasible to jump form $15k ACV over to $100k ACV?
This isn’t an exhaustive list. The better you can answer these questions, the better you can leverage the following resources to really pinpoint what the next ideal role might look like.
Resources to Decide What’s Right for You
Outside of my Substack recommendations, here are some great resources that will either help guide where to go but also how to get there.
Trends in the Market
Sapphire Ventures Resources specifically 2023 Buyer Report
Resources on How to Get There & People to Follow
Matt Barron provides a course and other resources on getting into tech/ tech services. I’ve personally met him and he’s doing great work helping people trying to break into tech or level up. Give him a follow on Twitter.
BeautyofSaaS provides a course on how to break into tech sales and level up your sales acumen. I’ll preface that the course is not free however the content provided that IS free speaks for itself. You’ll get a ton of value by just following on Twitter or Substack.
Pedro Castenada Break into Tech Sales provides a free course and you can follow him on Twitter for extremely valuable content if you’re just starting out.
BowTiedCocoon also provides a paid course on how to break into tech. Not sure when the Substack is coming but his free content on Twitter is valuable nonetheless, also recommend giving a follow.
Then … GO TALK TO PEOPLE
When I started taking my career more seriously and trying to figure out what path I was going to pursue long term, I played the game of elimination. I looked at LinkedIn Job descriptions and ones that I was interested in, I placed into an excel sheet.
From there, I mapped out HS alumni, college alumni, and even cold messaged people in those respective categories. With all the info above, you can apply this to which sales role you’d want to take on and learn more about it.
When you have a long term view, you’re committing to a time horizon of one to three years. People more often than not are willing to help. You’d be amazed what you can learn in a twenty minute conversation. It could help you disqualify a role you thought you wanted. Alternatively, the conversation can be used as a jumping off point to learn what you need to get to an ideal role, or better yet, an introduction to a hiring manager.
Take the shortcut.
Fit is SO Important
This last point is extremely subjective, yet critical. I had caught up with some old colleagues and we started talking about successful NBA teams and rosters.
You hear stories about professional athletes who are extremely talented but don’t fit into a certain team’s system. They don’t prosper. Greg Poppovich, head coach of the San Antonio Spurs comes to mind because he does this extremely well. He not only vets out incredible talent but talent that will fit well into his system. Talent that he can mold.
Companies do the same things professional teams do with their athletes. They not only acquire top talent but top talent that fits into their system. I note that it’s subjective because it’s not something that you’ll find in a website, it’s a feeling and one you can only get through conversation.
If you have questions, feel free to reach out.
As always, thanks for reading and see you next week.
-Andrew Kobylarz