The Whirlwind of the Past Five Years

This is my experience over the past 5 years…

For over a decade I worked in the retail field and didn’t have a desire to leave it.  It was comfortable and the money was decent enough to make a living.  It was always an assumption (of mine) that I would end up working in Real Estate or managing a big box store of some sort down the line.  Around 2 years before Future Shop closed its doors, most people could see the writing on the wall.  Instead of doing 70-80k per day on the weekend, it was dwindling down to 30-35k.  Staffing was non-existent in certain departments and sales-people were asked to be experts in all different areas of technology. I actually sold a fridge with a closing line of “that it could take a punch if you ran out of beer”. It was only a matter of time before our store in Cambridge was going to fold up and I would receive a buy-out.  At the time in my head, it did not make sense to look for a new career because of this.

Over those two years, I was determined to figure out what to do next – Real Estate, Insurance, and Managing in Retail were all possibilities… sales in tech was where I decided to go.  It wasn’t easy to get into, there were many companies that didn’t want to hire a mid-30’s retail sales dude as an Account Executive.  Most tech companies want b2b (business to business) sales experience which I did not have.  Business Development was generally a role for young adults straight out of school and had a salary that was going to be a pay cut compared to what my commissions were at FS.  Even after deciding that it was worthwhile taking the dip it was still extremely difficult to get hired into this role. Most companies figured that I would leave at the first chance I got.  That, or my expectation to move up within the company would be urgent – interviews were piling up in tech, but no bites.  There was a job at a Bell store that was sitting waiting for me, but the burnout from Retail was real for me.  I did work one day at Bell and dealt with a (Karen) customer issue of their kid streaming media while in the States and the bill was in the hundreds… that afternoon I decided to quit with no offer in hand.

Finally, I interviewed with a cybersecurity company called eSentire… I’d never heard of them and had no idea what they did.  I met with a VP at the company that was building out the Business Development program and ran the Inside Sales team as well.  This dude interviewed me in a style that I had never seen or been a part of before… no standard template of interview questions or typical fluffy banter.  It was a relaxed conversation asking me questions on how I (the style) sold computers at Future Shop and drilling into what his concerns were about hiring someone that had so much experience selling a certain way.  Instantly, my guard was down, and it felt like a real-life conversation you would have at a bar versus being judged and analyzed.  It was refreshing and I laid it all out and ended up getting the gig.

Since then it has been a crazy ride of moving into different roles and learning all sides of how tech sales works.  The easiest way to describe the fast-paced world of tech is, it is like a very addictive drug.  Every decision and direction that you take has a huge impact on the business – I have been lucky to be given a lot of free reign on the moves and vision that I have.  To make changes at most companies it has to run through multiple layers of the business before even the smallest thing can be changed.  This is not the case at most tech companies, changes are often made on the fly. This makes the job fun, and also extremely stressful.

In my case, I’m directly/have been responsible for the livelihoods of dozens of young professionals that for the most part is in the first “career” type job.  The hiring strategy that I take is that it is preferable for the candidate to have had a tough job (retail, serving, door to door, etc…) in the past. Cold calling potential prospects requires a thick skin and have already dealt with tough situations it is easier to get over that “fear” barrier. Generally, with the talented people that I have seen it takes 6 months of the job before I see the light bulb “turn on” above their head. At that point, you can generally see what skills they have to help them choose a career path to strive towards in the future. Anywhere from the 1 year to the 2-year mark they leave the nest so to speak. It’s extremely satisfying seeing people that I’ve managed to move into different areas of tech, and quickly have success… that’s my drug! If I didn’t get a chance to work with my original VP there’s no doubt in my mind that things would have ended a bit differently. He taught me that I could be myself while managing… (I’d like to think of myself as) honest, genuine, and empathetic when leading. I always had this idea in my head that you needed to “become corporate” when in charge – there is nothing further from the truth. The goal that was imprinted on my brain was that you allow people to show you their skillset, give them structure and confidence to excel in the role without hanging over them.

I’ve been lucky to have great leadership for nearly my entire time moving from eSentire to Axonify, and back to eSentire – you don’t know how important it is until it’s gone.  I have no idea where/what I will be or doing in 5 years… that used to stress me out.  Now, since living in slightly controlled chaos it does not give me the same anxiety – it’s a nice feeling.

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