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TCSP #2: This Mistake Is Holding You Back

Welcome to the archive of the TCSP newsletter. This is episode #2.

The last time I emailed you, I shared my outlook on dealing with rejection which was pretty deep. This time I want to speak about something a bit more hopeful – figuring out what you *actually* want to do. After having hundreds of one on one sessions with people looking to make the switch to Customer Success, there’s a common mistake many people make that prolongs their move. They know they want to do Customer Success, but… That’s about it. The thing about Customer Success is that it’s incredibly vague. SaaS is vague. I quickly looked up “customer success manager” jobs on LinkedIn and got back 128k results! 128k RESULTS – that’s overwhelming AF. That’s like going to IKEA knowing you need to buy something for your home but just not sure what. So I’m here to help you fix this once and for all. Let’s get to some action items👇: #1 Take a good look at yourself Before you go searching for a job, you’ll want to take a moment to define what you’re looking for. And no, I’m not talking perks (tough love moment: you better not be saying that the reason you want a job is that you can work from home 👀 I’ll save this for a future email); I’m talking about what industry, company size/stage, type of CS work, etc. You can get to that answer by considering your experience and interests. For example, if you’re a teacher, you might be drawn to EdTech because you’ve already used many EdTech tools. Let’s say you don’t have such a clear path; maybe you’re a bartender (I was too before I transitioned to tech), if so, you’ll have to cast a wider net to increase your chances. I’ll tell you more about my story below. Your homework: Make a list of your experience, tools you’ve used, and things you like (being organized, planning projects, etc.). This will form your base of compatible companies, where you can find a CS job that fits YOU. #2 Do the research I ended up at a user experience and conversion rate optimization software company (no idea what that meant when I started) but doing my research led me to the right place. As a former paralegal/bartender, I had a knack for customer experience. So when I saw the job posting come up on, I found myself naturally drawing the dots. Before this job, I applied to other industries like finance (or fintech) and got nowhere. I didn’t know, like, or could draw dots to fintech, and I’m sure that came through during my interviews. Something else to keep in mind is if the industry you’re applying to is entirely new to you, there’s also that steep learning curve you’ll need to consider. For example, if you’re applying to a cybersecurity CS job and have no idea of what cybersecurity is, you’ll need to account for learning a bit about the industry before your interview. #3 You have a type, but you can make exceptions I had this ridiculous rule around dating: If they’re not taller than 6 feet, it’s a no for me. I dated a guy who was 5’9, he absolutely broke my heart, but the heartbreak had nothing to do with his height. He was just a shitty person. What did I learn? Height wasn’t as important as I made it out to be. The height – at the end of the day – was a preference. Not a dealbreaker. I want you to have a strategy: Be clear on the industries, company size, and all that jazz. But I also want you to be open to new opportunities that might arise. It’s okay to experiment because this is how you’ll know what you like and don’t like. — I hope that these three quick tips are helpful to you. And if you feel you have a strategy down but are still struggling, write back to me! I’d love to hear how things are going and see how I can help.

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