Connecting the Dots

After dropping out of college to take care of his father, Winston Helena was introduced to tech recruiting. 11 years later, he has enjoyed a successful career. After this interview was conduced he took the next step and joined local startup, Treely, as a managing partner.


What was it like in high school for you? Did you know what you wanted to do?

No clue. I think later in life I realized that I naturally went towards networking. For me, relating to people was natural, it was easy. I could drop from one social circle into the next. I could easily mingle, and was easily accepted. It wasn’t something I gave thought to at the time.

Tell me about your college experience

I don’t remember how long it was for…few semesters maybe. My plan was to go and get the basics at community college, figure out what I wanted to do, and then transfer over to College of Charleston. My reason for dropping out was three-fold. My father was becoming ill, I didn’t know what I wanted to do when I grew up, and the financial burden that would come college was too much because my family wasn’t able to pay for college. I would have to take out substantial student loans when I didn’t know what I wanted to do. It was a combination of those 3 factors.

At what point did you realize that college wasn’t for you?

Probably at the point where my father got sick enough that I realized I had to make a decision. It was that, compounded by the fact that I didn’t know what I wanted to do anyway and I didn’t want to take on the burden of student loans when I don’t know what I’m doing.

What did you decide to do next?

I decided I needed to find a career path, not just a job. Once I made that decision, it was the “aha” moment. I could keep working a job 9–5 for a paycheck, go back to school to find a career path, or just find a career path and find something that I enjoyed doing where I could grow and develop as a professional.

Was that when you discovered recruiting?

It was. A good friend of mine’s father introduced me to it. At first all I knew was that he had his own business doing something with the computer world, worked for himself, took care of 8 kids, his wife stayed home. They had a nanny. I was like “man! I need to learn more about this.” I started trying to figure out what it was that he did. Eventually got to the point where I said “man, I think I can do that.” So I started asking him for a meeting. “Can I take you to lunch? I’d like to talk to you.” When he finally said yes I asked him for an opportunity to give me a chance and learn what he did. I felt like I could do it and I wanted a shot at it.

“…I asked him for an opportunity to give me a chance and learn what he did. I felt like I could do it and I wanted a shot at it.”

How long did it take for you to learn the basics and get your feet on the ground?

I don’t know if I could put a real time-frame to it. In recruiting if you take that same situation with someone brand new and green and put them in a large environment like Aerotek it’s a sink or swim thing. You know in a few months if you’re cut out for it or not. It’s just that apparent. You have a comfort level on the phone, you can connect dots for people and understand the needs of the organization, reading between the lines of a resume and not just looking at whats on the paper.

That brings us to the question, what does a recruiter do?

I think you could ask that question to 10 different recruiters and get 8 different answers. It depends on the environment, the company, so many factors. If you boil all of that down and don’t worry about a specific niche, it’s connecting dots. It’s understanding needs, understanding drivers, seeing between the lines and piecing those things together. What is motivating the person? What are their desires? What do they want? It’s also understanding the needs and the culture of the organization where you are. What the company needs out of a person might be totally different than what another company needs. It’s very much a relationship building and connecting the dots.

It’s understanding needs, understanding drivers, seeing between the lines and piecing those things together. What is motivating the person? What are their desires? What do they want? It’s also understanding the needs and the culture of the organization where you are.

What does your day-to-day look like? What tools do you use?

Phone and email are a big part of it. You can be a recruiter as long as you have email access and a phone. Day to day it’s a lot of conversation, lot of email. It’s getting to know people and track them down. You’re chasing hiring managers to find out what they want, chasing candidates, looking for feedback and piecing together all of these things. It can be very hectic, very chaotic.

Does being a recruiter take strong social skills?

It definitely helps. Is it necessary? No, because there are certain types of recruiting that are more scripted and robotic where there’s not necessary a personal side to it. There is a way you can do recruiting and be more of an introvert without having to be that social butterfly. The type of recruiting I do, especially in the technical world, you really need to have some kind of draw or natural passion for conversating with people, for making connections, for interacting and having a social and personal touch.

“You really need to have some kind of draw or natural passion for conversating with people, for making connections, for interacting and having a social and personal touch.”

How difficult is this field to get into with no experience and no college education?

If I had been more self aware in high school and known that I had a tendency to be very social, I would have spent less time building houses for an hourly job and more time trying to get into recruiting earlier. It’s definitely not a career path where you need a degree. Could it be helpful? Maybe…sure. Psychology degree, sure. It’s more about do you have a natural tendency for relationship, conversation, for putting things together? If I weren’t such a social person I likely would not have made it. You see this in the big companies all the time, people come in very green with no experience whatsoever and they flop out after a few months.

Do companies hire green employees?

A lot of the larger firms do. That’s a good way to figure out if you’ve got the chops to get into recruiting. Go to a large firm. Aerotek is one of the biggest, they’re one of the best as far teaching the basic and fundamentals of recruiting. It’s like bootcamp. You get in there and you sink or you swim.

My personal preference would be for somebody to start like I did at a smaller, more boutique type firm. Find somewhere where you can have a true mentor to teach you versus a body shop (like Aerotek).

What are some ways someone can learn more about recruiting?

Right now, Lou Adler is the number one. He is the recruiting guru and he’s got a company and a blog. He’s one of the best to follow as a jump-off point. They cover such a large spectrum.

There are also multiple recruiting groups on LinkedIn. Go into LinkedIn and identify groups specific to your geographic area.


About College Opt Out

The mission of College Opt Out is the tell the stories of men and women who have forged their own way and enjoyed successful careers without a college degree. We want to inspire high school and college students to consider the alternatives and realize that a college education isn’t their only choice to establish a fulfilling career.

If you have any questions about College Opt Out, or know someone we should interview, please email paul@collegeoptout.com