5 years

Posted by kdow on Oct 3, 2017 8:39:55 AM

Photo by Shubhankar Sharma on  Unsplash

On October 1st 2012 I embarked on a journey that I honestly didn’t expect to last 5 years. That journey was one where I took a role at a relatively young, funded startup called HubSpot. They were opening a new EMEA HQ here in Dublin, and as it turned out I was the first person to sign on the dotted line & get whisked away to Boston for new hire training.

I was hired as a “Sales Engineer,” something I knew absolutely nothing about. I came from a technical manager & programmer background. This is why the agency decided to reach out to me. But I was skeptical of my fit in a “Sales Engineering” role, or my role within a cool company. A few years later, in early 2016, I shifted my career to be a leader within the Sales Engineering org, since growing the team by a few hundred percent and taking the reigns across five offices. Defining the role and expanding that definition out to other people has been a huge challenge. A hugely rewarding one! Heck, last year I even documented my fourth year in-role, with an eye to the next four.

Today I’m facing new career challenges as we go into 2018 as our business evolves from startup to scaleup. Somehow, I’m even helping to mentor startups in Dublin & Singapore (reach out if you’d like some sales, marketing & SaaS advice from a techie).

And in 2018, I also get a huge opportunity to take a month off on sabbatical. Paid. HubSpot even generously give money to help make the sabbatical even more tempting, special & momentous.

And as I spend some time reflecting on the past 5 years, my main thought is how did this happen? I often look inwards, being fairly introverted (I hide it well), and find myself in a sea of worry, shame and guilt. The imposter syndrome is strong with this one. But that seems to add fuel to a pretty raging fire that’s spurred my career forwards at an accelerated pace. Hobnobbing with C-level execs, public speaking in front of 500+ folks and advising entrepreneurs were not in my future 5 years ago. God knows what’s in store in 5 more.

What’s really eye-opening is how much more comfortable I am in my own skin. This year I embarked on a “fititron 5000” program to get in shape so that I don’t die at 35. That’s worked out really well so far, and I wish I did it earlier. My wife & I are settled into our lives as a married couple, with our 5 month old labradoodle, Marla (named after the girl in Fight Club). And now, being nearly two years into a leadership role, I think I’ve finally figured that bit out too. And while traveling is a lot of fun and probably the best mini-MBA I’ve ever received, it’s now tiring enough to want to pass some of it onto others.

I recall being in a new hire training class when someone mentioned the perk of being given a paid sabbatical after 5 years in the company. At the time, no one had taken one because the company was too young. Now, I’m at that point where I’m one of the flying spaghetti monster creatures who gets to take one in the next year. Who knew this would happen?!

So, for anyone wondering if their careers will be successful or not. Anyone doubting themselves. Keep pushing. You’ll surprise yourself. And in a few short years, you’ll look back on the journey and wonder how that happened.