A Salesman’s Adventure – A Walk Through the New York Job Market


The real life story of a salesman’s search for a sales job in New York.

As I headed down the subway steps I asked the sales manager, who was tasked with evaluating me for the day, ‘Where are we going?’ He replied simply, ‘Glendale’. I had never heard of the place. I thought about walking away right there. I had been told to expect a full day trial, unpaid, held at what I believed would be their offices near Times Square. The thought of spending the day in unfamiliar territory made me uncomfortable. However, I decided to ignore those negative instincts and take the steps down to the subway. I had nothing to lose. Worst case, I could write about it.

After a forty minute train ride we arrived at our destination. The sales manager unpacked his case to reveal a foldable table. He set up the table under the tracks of the subway, placed a white cloth on the table and two cell phone boxes. He then started shouting, ‘Free cell phones!’ ‘Free service for cell phones!’ After 10 minutes of training I was expected to repeat the same lines and attract people to sign up for a cell phone at a giveaway price of $99 which would come with free calls and data for life. A great deal if you qualify. There was no basic salary. That wasn’t something that was made clear in the ad. After 15 minutes I took a bathroom break and ordered an Uber.

Welcome to sales jobs in New York.

This article follows the journey of a salesman around the New York job market.

The starting point for sales jobs in New York is always the same, Craig’s List. A quick plug here. Sell Me This Pen Careers is aiming to be New York’s #1 Sales Job Platform. You can check out the latest remote and non-remote jobs here. It’s my company which I set up realizing that there should be a one stop shop for sales jobs.

I have tried most sales jobs out both located in New York and remote. Mostly as an education for my new sales focused recruitment firm Sell Me This Pen Careers and partly to earn cash to launch my new business and pay a few bills along the way.

That first experience was enough to stop my search in its tracks. For who wants to be standing on the street screaming out, ‘Free cell phones!’ when it is cold and wet. Despite my lack of interest in closing sales on the street I would still rate myself as hungry with a fire in my belly unmatched by the majority of people. But the job just wasn’t for me. Next…

Next up was a remote position with a Boston based event staffing company. My job was to call up people who had inquired as to the cost and availability of staff for their upcoming wedding, birthday or cocktail party and attempt to persuade them to use our bar staff and waitstaff. I had to work 20 hours a week at $20 an hour plus 2.5% on the sales I made. It was a pleasant, relatively challenging and rewarding job. I spoke to a large number of receptive clients who trusted me with their wedding arrangements. I was quickly promoted to sales manager until the owner was booted off the gig platform that was the source of much of his business. I was fired shortly after. Next.

Next up was an interview at a Wall Street based Merchant Cash Advance firm. If you study Craig’s List as often as I do you will no doubt come across something called MCA or Merchant Cash Advance. In a nutshell it is a way of funding small businesses which are short of money. The MCA provider advances money to businesses backed by the business’ credit card sales. Salespeople usually cold call mom and pop businesses asking if they have a requirement for cash. MCA sales jobs are generally commission only roles based from an office. There are usually 3 or 4 MCA businesses advertising for sales brokers on any given day.

I attended an interview and was asked to pitch the owners product with no knowledge of MCA at the time. It was a great pitch, if I do say so myself, which Mr. Belfort would have been proud of, but I wasn’t offered the job. I attended another interview for an MCA firm based in Midtown Manhattan where they paid a basic of $17 per hour and provided lunch. I was offered this job but decided to stick with the event management gig. I preferred remote work.

A role I would have liked to have landed was a Solar Power gig based in Brooklyn. They were looking to hire staff to switch consumers from their existing energy supplier to solar. It was paying an attractive base of up to $25 per hour plus commissions. Solar seems like a good market to get involved in, I reasoned. But they were looking for someone different than me and I was on to the next interview.

Enter Legal software. It was an appealing advert. $55,000 base plus commission. That base was sure to motivate me and of course pay my bills with some money left over for my sales recruitment venture. I was called into an interview on Jamaica Avenue, Queens. The juicy base wasn’t without a catch. I had to call on 20 law firms each day. That required a car, which I did not possess. It was also December. Going door to door in the sub zero temperatures wasn’t my idea of fun, good basic or no basic. Undeterred I very reluctantly volunteered for the challenge. And, as envisaged, making 20 calls a day was no push over. But it was achievable. After I had made my 20 calls I had the day to myself. All I needed was a very warm coat. And of course I got to know the streets of New York like the back of my hand.

Sell Me This Pen CAREERS – New York’s #1 Sales Job Board

Find your next sales job here

Banner Image: Sales meeting. Image Credit – Austin Distel


Harry Maximillian

Harry is an author, coach, entrepreneur, comedian and a convicted felon. Harry was sent to prison for a financial crime where he spent five long years. Prison allowed Harry to realize the error of his ways. He decided to use his time productively and mobilize his extraordinary determination, dedication, drive, motivation and desire to focus on writing and the art of self-improvement. Before Harry’s enforced vacation he was one of the most prolific deal makers in the City of London.

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