The PivotDesk Blog

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From Suits to Jeans: My Path to a Startup Career

Today, we’ll hear from PivotDesk’s NYC Account Executive, Adam Greenfeld, about the journey that led him to leave corporate America for a startup career, and the lessons he learned on life, sales and picking the right job along the way. Have you had a similar experience? If so, tell us about it in the comment section and we’ll weigh in with our thoughts. 

Every morning, as I open my closet, I am reminded of how I spent my 20’s. Neatly organized on a rack, 4 feet wide, hang dry cleaned suites, starched white button down shirts and a vast assortment of neckties.

You guessed it, before jumping head-first into the startup world, I worked in corporate America.

Fair warning, this is not going to be a corporate suit bashing piece.

In fact, I loved my job, the work we did and the people I worked with were nothing short of awesome. The problem that I ran into was that eventually, the fire I had right out of college to wake up every day and try to take over the world had diminished. Like countless others striving to climb the corporate ladder, I found myself questioning my motivation to work hard.

So, as I approached 30, I realized that at no fault of my employer, the corporate lifestyle, for me, had run its course.

After accepting this, and seeking guidance from an amazing mentor, I decided to do something to get myself un-stuck. In November of 2014, I resigned for the only adult job I’d ever had. Next, I locked all of my custom suits away, grabbed a backpack and bought a one-way ticket to Southeast Asia.

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Adam in India

Scared as hell and quite inexperienced as an outdoorsman, I resolved to adhere to one common theme throughout the journey, “Everywhere I go, I will find a way to give back to the community that is nurturing me.”

[bctt tweet=”Everywhere I go, I will give back to the community that is nurturing me. – Adam Greenfeld” username=”pivotdesk”]

This credo manifested itself in a series of volunteer jobs at orphanages, ashrams, farms and even a Crossfit gym in Sri Lanka.

I could write forever about my trip, but this is about the 2 lessons I realized when I got back:

1. Life is much shorter than I had fully realized — I can’t waste time living a life that’s not exciting.

2. Unless I feel like I’m truly helping people, I won’t feel fulfilled or motivated.

In solidifying these realizations, I had also laid out the prerequisites for my next career. So, I set out on a wide search that resulted in dozens of meeting and weeks of research.

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Singburi, Thailand

It wasn’t until I started sitting down with the PivotDesk team that I saw what a significant issue they were working to solve… the epidemic of irresponsible real estate spending that had struck the global business community. I understood quickly that what PivotDesk was doing could help countless businesses and entrepreneurs, and with my background in corporate sales, there was value I could add. So the idea and the vision were there — excitement box checked.

Next was the deeper question: did PivotDesk tout a culture that allowed its employees to create and perform to their maximum potential? I decided to truly dig deep and lift up the hood to learn what makes the people at PivotDesk tick. Because I believe culture needs to come from the top, I started with the PivotDesk Executive team. What I found was a group of leaders who blew me away with their honesty and transparency. After meeting the rest of the team, I was sold. And lucky for me, they were in need of someone to go out and spread their message.

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Adam exploring Hampi, India

It took me about 7 years and several thousand miles worth of travel to learn this, but it has become crystal clear that the first real sale any good salesperson needs to make, is selling him or herself on the fact that the product they represent really helps people.

If we can get to a point where every time we leave a meeting, end a phone call or send an email, the person on the other end is better for having spent time with us, we are setting ourselves up for amazing success — the kind of success that keeps our metaphorical fires lit, day after day.

Nearly 10 months into my time with PivotDesk, I consider myself one of the lucky few who has found just that.

If you’d like to contact Adam, you can reach him at

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