Start-ups Keep You on Your Toes

Kayleigh OKeefeDaily Stoic New Year, New You Leave a Comment

Day 7: Pretend You Have To Get a New Job—Today

Just a few months ago, I did have to look for a new job!

I had spent the better part of three years working at Snapdocs, a technology start-up in the mortgage industry. I loved working with my colleagues to help build a strong company, but ultimately tired of working day-in and day-out in the mortgage industry. In September, when I left to consider my next steps, anything seemed possible – let’s move to Florida! Maybe this is my opportunity to be a teacher? Time to start my own business!

This was my chance to make another leap! Yet, I found that the opportunities that were coming my way were all based on my network and my experience, which meant that I was receiving offers to interview for roles where I felt like I had “been there, done that.” Customer Success and Enterprise Sales roles were aplenty. I felt disheartened that the things I’m best at – working with customers, launching new products, partnering with other functions, leading teams, and achieving whatever we set out to – weren’t so obvious to the outside world. I also didn’t do a great job at getting clear at what I wanted next in my career and then communicating this out to the world through interviews.

Ultimately, I decided to take an opportunity at a great company whose sales leader I had met the year before and I admired and where I saw the potential to learn the ropes, fill a role, and then sense where I could help grow the company in the future.

The jury is out – did I take too safe of a route by moving into a similar role at a similar-stage company? Did I make the best call by surrounding myself with successful colleagues at a profitable start-up? Did I prioritize the things that matter most to me – walking commute, good environment, potential for growth? Did I chose the opportunity that came the easiest through my network?

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