Put Your Ego Away: Kevin’s Journey from Rejection to Hired


Attitude is everything. 2023 Aspireship Grad, Kevin Anderson, started and ran three different businesses and worked as a freelancer in two different verticals, and now he is a BDR with Prompt Therapy Solutions Inc. Today we’re excited to share his story with you! 

Prior to the Aspireship course, what was your background in sales, if any?

Prior to Aspireship I had started a couple of small local businesses. So I had sales experience, but no SaaS experience.

What excited you about sales?

I wanted to get into tech. I tried to get into coding and quickly realized it just wasn’t for me. So, I searched forums and saw there were a lot of software engineers complaining that the sales reps where making more than them. That’s when my ears perked up.

Did you have any challenges or hurdles when making your decision to interview for sales jobs? How did you overcome them?

The biggest challenge I had was going from business owner to working in someone else’s business. I believe a big part in overcoming that challenge is realizing we all need help. You can’t do it alone forever and grow.

What was the process like switching into your new position?

A lot of rejection. Haha. A lot of the challenge in switching was getting past the HR software that weeds out your application. It means if the keywords the company chose for the position are not in your resume, you never get the chance to show what you can do. That’s where Aspireship really shines.

What is your motivation for this career change?

The biggest motivators are growth and flexibility. I really wanted to learn more about the tech industry and how tech companies are run. On top of that the tech industry has always been known to be progressive. After the pandemic it became more so. Unlimited PTO and freedom to work from home are common place.

In recommending Sales as a new career path for others, what do you feel are the most important skills to develop in the first few months in this field?

Number one is to get rid of what some call “commission breath”. Have you ever walked into a store and the sales person sounded to
desperate for the sale, with that high pitched almost to happy tone of voice, and it completely turned you off? That’s commission breath. When you sound like that people automatically think this person isn’t really here to help they just want to sell me something. Stay calm with a relaxed tone, like you’re talking to a co-worker. After that, the most important skill is active listening. Don’t just wait to talk. Actually listen, then ask some calibrated questions to get your counterpart to go deeper. Skip Miller says the secret to this skill to be genuinely curious.

How were you spending your time prior to finding the course?

I was spinning my wheels applying to everything that had SaaS or tech in the title, just to get my foot in the door. I never got an

How did you come across Aspireship?

After sending hundreds of applications on LinkedIn, Indeed, and a few other sites I admitted to myself I needed a partner in this journey.

I was searching for SaaS sales programs and I narrowed it down to 3. Aspireship was the clear choice. The other 2 promised the same deliverables, but one program wanted $8000, and the other wanted 20% of my pay after hire for a year. Aspireship was reasonably priced, offered exactly what I wanted, and had teachers that are actually out there in the real world still doing this stuff for a living.

Was there anything about Aspireship that helped prepare you for this new role?

Absolutely! I though I knew sales.

But, I knew short cycle sales. Skip Miller talking about above the line buyers and below the line buyers was incredibly valuable. Then the entire team was always ready to help with interview prep. Ana literally scheduled a call the day before my interview to give me insights to what kind of questions the company founder was going to ask me. One question she recommended I ask them was a huge turning point in the interview and I got the job!

Is there anything else you’d like to share with us?

Put your ego away. A lot of us going to Aspireship have tried many things that haven’t worked. We also are coming with our own work
experiences and philosophies. While going through the program, temporarily put those away and soak up everything with new eyes.

Do you have any hobbies or activities you like to do in your spare time?

I’m an avid reader, and love playing “Monster” on the playground with my kids.

Start your journey today. Sign up and get access to RevOps, SaaS Sales and CS Foundations Section 1 for free! 

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