The man… the meme… the legend…
Yes, we’re talking about Caspian Lewke!
We welcomed him this week to the #salestage to share how humor plays into his outreach strategy and his personal sources of career inspiration.
💜 BIGGEST CAREER IMPACT
My family. Both of my parents were lawyers and then pivoted, which inspired me to explore different fields. My oldest brother works in finance, which is where I began my career, and my other siblings have worked in tech sales which motivated me to try it! They’re my biggest inspirations as well as my biggest cheerleaders!
🤡 IMPORTANCE OF HUMOR IN SALES
It’s a way for you to show some of your personality and that you’re human, just like the people you’re reaching out to. A lot of times, it’s easy to think of ourselves as salespeople and the people we’re reaching out to as prospects, but we’re all so much more than that. We all have unique interests and I strive to tailor my outreach to my prospects’ interests and add humor and personality!
🔧 SURPRISING SALES SKILL
Not taking things personally. I have been guilty of people-pleasing. In sales, you learn pretty early on that not everyone is going to be pleased with your outreach. Learning that was so important and honestly, a relief. Regardless of where I work or what I’m selling, it’s not going to be the right fit for every prospect, and that’s OK!
💵 FIRST THING YOU EVER SOLD
Tickets to my high school’s Winter Ball dance! Not many people were excited about it initially, but I tried to build some hype around it and sold 40 tickets to a pool of ~100 students.
🏆 WHAT EVERY SDR NEEDS TO SUCCEED
Persistence. You may be told no by 99 people, but that 100th person might be the person to tell you yes.
Creativity is key as so many things which compete for our attention nowadays. You’ve got to find a way to break through the noise and reach your prospects.
Lastly, ability to laugh at yourself. Funny stuff happens daily to SDRs. A prospect tells you off, your emails bounce, you book a meeting because someone is in a good mood. If you can laugh at things that happen, you’re going to have a better time.
🎵 SONG THAT GETS YOU HYPED TO SELL
It’s more of an interlude than a song, but I love to listen to “Better Luck Next Time” by Midwxst. He talks about how life is “too short to dwell on the past” and how “you’ve gotta keep pushing forward and forward” which always makes me think about how, as an SDR, you’ve got to keep your head up and looking forward to the next call, next email, and next sequence.