Episode #9 - How Blake Overholt went from selling cigars in the Florida Keys to Silicon Valley recruiting


In this episode we chat with Blake Overholt. Blake grew up in Sacramento, California before heading off to UCSB and majoring in Global Studies. He is now an experienced tech recruiter working for the SF-based CRM software company Insightly.

Blake, as many people do, had a roundabout path to his current position-- his first job out of college was as a cigar salesman in the Florida Keys. Now as a recruiter, Blake was able to share some amazing insights about how to stand out in the application process.

Alma Mater: UCSB

Major: Global Studies


Interview Highlights

(edited and abridged)

How did you go from cigar sales to a recruiting?

While I loved working for a small business, I really yearned for professional development. So I went out to California with a goal to get into the tech industry. It was a huge jump. You have to be really ambitious in this world to make things happen.

I was looking for both sales and recruiting roles since I had done some recruiting for sports in college. I started interviewing at a few different places, and during the first interview I had for a sales role I just got a really bad vibe from the people who worked there so I didn’t take that role.

My next interview was with a boutique recruiting agency where I would get the opportunity to work alongside the CEO, who had been working in the Bay Area for over 25 years, so I took the job and never looked back.

I was able to sit with him and learn about the industry. I think it was the best move I could have made because it helped me understand the industry at a higher level and learn why certain people were hired and others not.

What’s the day to day like for a recruiter?

A good portion of my time is spent on LinkedIn, which is a very important thing for anyone that wants to get a job in the tech industry. I also do a lot of full desk recruiting, which means sourcing leads for candidates, messaging them, convincing them to hop on a call, executing those calls, and then deciding if they are up to par to move forward. I then set up a screen with one of our managers and take candidates through the on-site interview process after they pass that.

What do you look for in a quality candidate?

I try to identify a history of top performance, which includes volunteering and activities outside of school to show that they are extending themselves. In addition, showing that you have a four year degree, especially in a sales role, shows that you can commit yourself to something for four years and succeed.

Are there any misconceptions about what it takes to make it in sales?

There is a stigma that only athletes are hired for sales, but that is not true — especially nowadays. You don’t have to be pushy, extremely confident, or a slimy car salesperson because most interactions aren’t done face to face anymore.

Today there is more of a teaching mindset behind sales, which means that if you are empathetic and keep your company’s needs in line with that empathy, you will be really valued.

If you can help people see their business in a different light and see the future potential value of working together, it is a sign of a good salesperson.

What is Insightly?

We are a CRM company, which stands for Customer Relationship Management. Think of it as a database for companies to keep track of their clients. Our focus is helping them build lifelong customer relationships. A lot of companies fail to keep those relationships strong, so we are filling that gap. We focus on the small to medium business realm.