The One About How Jimmy Became a Marketer

How does someone who has never held a marketing position (or any marketing degrees, certifications, etc.) find themselves in charge of all marketing for a successful, well-funded startup achieving rapid growth in a matter of months?

By accident and necessity of course!

Story Time

Going into 2018 I was working for a company that had its problems. I was a minority partner in a portion of the business and oversaw IT. Although my titles over the years at that company were “Director of Technology” and “Chief Technology Officer,” my job description was all over the place. I did a bunch of compliance work and a lot of digital marketing. I also did a ton of community work and learned a lot about building a brand. It was my first job out of college and was a true rollercoaster in every sense.

At first, the job was going amazing and I had a ton of early success at a young age, but eventually, the company completely fell apart. A private equity group bought the business and combined it with some others. I was let go from the company without warning in a weird flex of power (like found out after asking why my paycheck didn’t come without warning) and then promptly offered a job again with a big raise, back pay, and a new title a week later if I agreed top come back.

At the time, I was newly engaged and 25 years old. My then fiancé had just moved to New York City to start a master’s program. I was living in South Jersey (90 minutes from her with no traffic) and barely had any money. I was interviewing at job after job in NYC and all my opportunities seemed to fall apart.

I had to decide if I was going to take the raise and go back to my former employer or look for something else full-time. ?I knew I wanted to be living and working in New York City with a job in cybersecurity and called some friends for advice.

Most of the advice I got was to take the job and take my time looking for something new. It was the safer option and a sure bet. But when I talked to people who were actually living in NYC the advice was different. I will always remember a conversation I had that went something like this: “If you want to find a job in New York City you should probably move to New York City and look for a job.”

That made sense to me.

In still not sure if it was flawless logic or total selective hearing and confirmation bias, but I don't think it matters, and was exactly what I did. I moved myself to NYC with no money and asked literally everyone I knew if they had any connections with someone who worked in cybersecurity. Eventually, I found a friend of a friend of a friend who made it their mission to help me get hired at the company they worked at.

Getting a Job at SKOUT

I am so grateful for that person. They would not stop until I was working at SKOUT (then called SkOUT Secure Intelligence.) I literally got turned down by three hiring managers before they hired me. I would go and interview and I would think it went well and then I would get turned down for the job. The guy helping me would call afterward and be like, "don’t worry we can try this other person."

Eventually, I found myself in a room with the CEO, Aidan Kehoe. That interview was insane. He didn’t care about my resume or what I knew. He assumed other people already checked that. He wanted to know why I was in the room sitting across from him and how I ended up there.

I remember giving answers to his questions like “well I am passionate about cybersecurity” and “I can make an impact mitigating risk.” He would ask again and again…

“Okay… but really why are you here?”

Eventually, the raw and honest truth came out. I explained that I had no options and no backup plans. I was desperate for a job, and I would work my ass off doing whatever he wanted to do. We were basically yelling back and forth, and he explained to me that the person who got me in the room had never made an ask like this before and that I better not let him down. He then told me, I would meet some people who would probably offer me a job next and walked out of the room.

The next day I ended up on the sales team. Yes sales, not marketing like how we know the story ends, or a technical role like I originally intended. There is a whole other story about what exactly happened in the time between meeting with Aidan and getting hired but I will save that for another day. I had some hilarious interviews with the team we still laugh about today.

Becoming a Director of Marketing

So now I’m in sales for the first time selling managed security services. After a few weeks in the role, Aidan saw something I posted on LinkedIn while he was out. He called the office and had someone bring me into the room. He said “Jimmy I didn’t know you could write. I saw what you posted on LinkedIn. It was great. You are in charge of our LinkedIn now. I want you to get us to 1,000 followers by the end of the year.”

I still follow the advice he gave me back then. I would be scared to post something, and he would say “Why? No one looks at it now anyway so there is no risk. What is the worst thing that could happen, someone sees it?”

I also learned the value of being able to write early on. This is a key thing and a big part of why I put out this newsletter. I want to always continue to get better at writing.

Little did I know from that day forward I would become a de-facto marketing leader for SKOUT. A couple of months went by, and it became official. It all started with that LinkedIn follower goal (which I did achieve) and the asks got progressively bigger.

“Can you make datasheets for all of our products?”

“Can you make a partner portal by Monday?”

“Can you make sure we win the Moonshot Challenge?”

“Can you get all the reps a bunch of leads?”

These were real asks that I did end up figuring out and achieving. I literally just solved problems for people by googling and trusting my gut until people stopped asking me to do things and started asking me what I thought we should do. I figured out how to become a Director of Marketing and hired a team. I still don’t really believe how it all happened. I always saw stuff in the movies about people coming to NYC for opportunity and either making it or breaking it and moving back. That was literally my experience.

Never Underestimate Someone Who Can’t Afford to Lose

For me, the key point to this story is never to underestimate someone. There are a million reasons why I shouldn’t have moved to NYC without a job. There are a million more why SKOUT shouldn’t have put me in charge of marketing, but you can only win big by betting big. Aidan still jokes about how no one wanted to hire me except for him.

I really believe I came out successful because I didn’t have the option to fail. My fiancé (eventually wife) was in New York. New York is expensive. I needed a job in New York. This was my only option, and I could not mess it up. Where I lacked confidence, I had necessity to counteract it.

That may be an oversimplification and I don't want to discount the many people who helped me along the way. Sure I googled tons of stuff, but I did have real mentors and leaders on my team who taught me how to manage people and think strategically.

Also, this is definitely not some endorsement for everyone to go quit their jobs and move to New York. What will most likely happen to everyone at some point though, is you will be standing at a crossroad. One way will involve way more risk and way more reward, and it’s okay to take that path. Not everyone has the luxury of being 25 at the time, and although I could not afford to lose, having to leave NYC isn't really that big of a consequence when you compare it to other responsibilities people have. These things should also be taken into consideration if you are thinking about taking a big risk.

I had to figure out how to become a marketer as I went. I didn’t really have people to teach me core marketing skills, which probably was for the best because I improvised and mimicked the best people I saw online. I learned a ton and still look around sometimes and think “how the hell did I get here?”

And I really think I got here because I never gave myself the option not to.