Comfort: Before I Joined What Tax Form

7 June 2016
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I have admired the business landscape for much of my life, well arguably since my first “real” summer job in high school where I worked for an office organizing and filing documents. I learned that I would much rather use my brain power sitting in an air conditioned office working “professionally” than wrangling shopping carts or working in a fast food restaurant, etc. I also realized that the people that worked in these “professional” offices seemed to be doing pretty well for themselves. The likes of lawyers, accountants, doctors, real estate agents, insurance agents, etc. attracted me because they seemed to work for themselves and have freedom with their time. It is no surprise that after a short stint in commercial real-estate that I found my way into a small technology company as a salesperson. When I interviewed for this company I had no prior experience in the industry, and I remember clearly that the two founders were willing to take a shot in the dark when they hired me. I struggled immensely in my first few years partially due to the major economic meltdown of 2008 that impacted sales everywhere, but in large part because my company was small. There was no structure and, thus, few resources that would normally be provided to a recent college graduate. No corporate training program, no human resources guidelines, no sales manager, no marketing department and definitely no onboarding process. I was provided a company laptop, a desk phone and the credentials to our prospecting database.

Eight years has passed since I was hired at that small technology consulting firm and I can’t believe the experiences it had provided me. In the early years there were days when I drafted resignation letters because the path set before me seemed impossible with what felt like little to no progress day-in and day-out. Hindsight is 20-20 because I could not see that perceived failure leads to growth in one way or another. What seemed like challenge after challenge was actually experience in the making. I was engaging on a daily basis with any number of world class organizations across various industry segments. My goal was to understand as much as I could about how their technology operations ran, and compete for the opportunity to bring creative value to their priority projects. I learned how technology was leveraged in movie studios, international architecture firms, hospitals, law firms, publicly traded enterprises, manufacturers, cement distributors, stone importers, banks, service providers, credit unions, public school districts, cities, counties, private universities…and the list goes on. Every now and then one of these entities would place their trust and investment in a solution strategy I created with our team of engineers, and I would earn a venerable new client.

The capability to digest an organization’s business model, identify areas of untapped value, engage decision makers of varying personality types and nurture business relationships ongoing is an incredible experience to undertake. The fear of the unknown every time I sat down with a new prospect transformed into a confident charge into a new puzzle waiting to be solved. That feeling of comfort was earned over years of failure and unwavering persistence to move forward, whether an inch or a mile at a time. There is a lot to be said for someone who has a career that has reached a stage of earned comfort. It is the product of sacrifice, discipline and hard work while mentally conquering fears of a constant unknown. Enter the opportunity to join a startup company and leave comfort behind, What Tax Form.

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Written By: Emily Rotolo Founder & CEO

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