Sell to Win

What was the first sale you ever made? 11 successful salespeople discuss their first big wins

Cody Slingerland
Senior Contributor, Sell to Win
Cody Slingerland
Senior Contributor, Sell to Win

There’s something about the memory of your first real sale that elicits pride, confidence, and love for the profession. 

No matter how young or inexperienced you are when it happens, that first sale leaves an impression that stays with you for the rest of your career.

We asked 11 sales professionals to take a trip down memory lane and share the stories behind the first sales they ever closed. Remember your own first sale? Tell us about it on Twitter or in our Sell to Win Facebook community!

Previously: What’s the craziest thing you’ve ever done to make a sale?

Charles Sprinkle, Senior Sales Strategist at Stackfolio

My first sale closed in 1987, roughly 60 days after I was hired by Merrill Lynch PF&S. The class of new brokers and I had just completed three weeks of sales training in Princeton, N.J. I don't remember the exact name, but I know I sold $10,000 of a closed-end bond fund. 

I remember being very relieved and excited at the same time. I had done nothing up until that point but hit the phone every day, looking for prospects willing to invest today or within a very short time. It was a process that required quick wit and thick skin (as they always say). I recall how easily I became robotic; my script just rolled off my tongue without a hitch. 

We were taught to listen for “buy” signals, which turned out to be way more involved than what was taught in our sales training. At the time we joked we were Robo-brokers, but the knowledge I gained has been immeasurable. 

I'm sure there are technical names for the various sales tactics we used at Merrill Lynch, but the process felt far simpler than that. We were in an environment where "here is your desk, there is your phone, pick it up, smile, dial, and introduce yourself" was the majority of making a sale. After that, ask open-ended questions, listen, and based on what you heard, either:

  • Work the angle to make a sale
  • Qualify them enough to call back
  • Hang up and start on the next call

Through it all, the biggest asset I had was perseverance, which is the reason why I'm still in sales 30+ years later.

Lauren Grech, CEO and Co-Founder of LLG Events

Six months into marriage, my husband and I had to sell our apartment, our cars, and move in with my in-laws (not something I recommend to any newlyweds), all because I had resigned from my job as a research and development scientist and failed at my first attempt at starting a luxury wedding and event planning business. 

For months, I had worked for free in all facets of the industry: watching the chef prepare food, working as a bar back, on my knees fixing a dress as a bridal attendant, scrubbing toilets as a bathroom attendant. I spoke with everyone and made every single person feel important because I knew I wanted to start my own business, and you can’t lead if you don't understand and respect the roles of others.

I spent all of our savings on a showcase in which we didn't book one client. Soon after, I was walking down the street and saw a Colombian model whom I had spoken to while volunteering my time to learn about the industry. When we first met, everyone had ignored her off the set because she couldn't speak any English. Coming from a Spanish background, I took the time to learn about her life, and she ultimately became the start of my success. When she stopped me on the street months later, she told me that she had just gotten engaged and I should be her wedding planner.

She became my first full-service client, which also happened to take my business international, as she planned to get married in France. Fast forward to now, I've grown my self-funded international wedding and event planning and design firm with massive success in just three years. 

I became a 2018 Forbes 30 Under 30 nominee in the social entrepreneurship category for taking a $300 billion event industry and creating philanthropic revenue. I also founded the youngest company ever invited to the Destination Wedding Planners Congress, where 70+ countries are represented in the largest B2B platform for luxury vendors that caters to celebrities and royalty.


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Toby Miller, Entrepreneur

I grew up a third-generation entrepreneur and was introduced to sales at an early age. My father always had me in the retail store with him if I wasn’t at school or basketball practice. 

One Saturday in October I learned a lesson that still sticks with me every time I’m making a sale. My father was busy with a customer and a gentleman was looking at a pair of boots. 

I walked over and asked him where he was from. He told me with a smile, and then I asked him what size he was. He told me and I grabbed his size in the boot he was looking at. 

After trying them on, he said, “I’ll take them.” I then proceeded to tell him we had leather cleaner and conditioner for his boots. He took a bottle of that, too. Finally, I asked him if he needed any boot socks. He bought a pack of those as well. 

I was beaming with pride at the big sale I just made. When the customer left I thought I was going to get a high five or a “good job son.” My father asked me what I sold and I told him all about my big sale. He then explained how I did well making the sale, but wanted to know what I thought I did wrong. 

I was perplexed and told him I sold him three things. He asked me what the customer said “no” to. 

I said, “Nothing. I sold him everything I showed him.” 

The lesson I learned that day was that I didn’t keep asking until I got a no.

Joseph Cirillo, Digital Life Insurance Agent and Co-Founder of Good Life Protection

I made my first sale when I was 14 years old. I sold advertising for my Catholic High School's spring musical fundraiser. People could buy a playbill advertisement in our spring musical to support the school. 

I targeted businesses and alumni in the community as a way of giving back and was a natural salesman. I ended up being a top fundraiser every year and received incentives like a free trip to Six Flags Great Adventure, a dinner and a Broadway show, as well as a cash prize.

Every year, I would rush after school on day one of the fundraiser to all the businesses that advertised in previous years, which taught me the first one in the door has an advantage.

Some businesses wouldn't buy on the first visit, so I had to return a few times to get the sale. This lesson taught me that the fortune is in the follow-up. 

Finally, I hand-delivered the playbill with their advertisement to them with a handwritten “thank you” note, which taught me gratitude and customer service.

The next year when I returned, you better believe they remembered me. 

Kevin Dorsey, VP of Inside Sales at PatientPop

I remember my first "big" sale, and looking back it's pure comedy.

At the personal training studio I was working at, I finally got the thumbs up to sell the training packages. 

Debbie was my first real sale. I asked the right questions. I dug in on the why. I went through the pitch. I was nervous as hell. 

When it came time to close, I presented the lowest cost option of $500 per month, which to me was A TON OF MONEY!

She looked at it and said, "Is that the one that is going to get me to my goals the fastest?"

I said, "Well no, if you really want to get there fast, you'd want to do the 1x1 package which is really expensive, it's $1,500/month."

She said, "Perfect, I'll take that one."

I almost fainted. 

She gave me her card, I swiped, and it wouldn’t go through! I was panicking. I called my boss nervously, like, “Um hey, the card won't swipe. What do I do?!”

He calmly let me know we didn't take Amex, and just to ask her to use another card. Which I did, and she didn't even flinch.

$18,000. Deal. Closed. 

The moral here is if someone wants it, they'll help you close the deal. But it's also on you as the salesperson to actually sell them what will get them to their goal, even if it's more expensive.

Steli Efti, CEO of Close and host of The Startup Chat

I'm not proud of my first sale, but I value the lesson it taught me to this very day.

I was a teenager back in Germany and had responded to an ad in the newspaper for a part-time sales job. They gave us a script and ran us through a quick training program and had us hitting the phones. We'd "survey" people about their tax situation, but after doing this for a while it started to dawn on me that this was a shady operation. When the "survey" indicated that these people had money, another sales team would call them again to schedule an appointment with them. The ultimate goal was to sell shitty real estate at inflated prices.

There was this old couple who showed up for an appointment one day. Normal working class people, just like my own family. They signed a deal. I got a $500 bonus—but I felt terrible. I didn’t want to sell people things they shouldn’t buy. I didn’t want to take advantage of people’s weaknesses through my strengths.

It's one of the fundamental principles of our own internal sales culture at Close now: Never close a deal just because you can. Only close it when you should.

Bradd Levitan, CEO of Wolf Spirit Distillery

In 1994, I was in my first year in the industry and working for Jim Beam Brands. I was a merchandiser rep, so my day-to-day routine was building displays, putting up point-of-sale materials, and trying to get shelf resets

That year when the company introduced Knob Creek Bourbon, my boss tasked me to go out and sell 20 cases. I had a counterpart in my job and I wanted to make sure I sold more than he did, faster than he did.

The next morning I went to Kappy’s liquors. At the time, I was calling on that account weekly and had a good relationship with the manager. I showed him Knob Creek, which was the first small-batch, ultra-premium priced bourbon. 

He said it was too expensive and wouldn’t sell. I asked him to give it a shot for me and offered to come in and hand-sell it to his customers by educating them on small-batch bourbon.  

When he heard that, he agreed. I continued the same pitch and ended up selling 45 cases on that very first day. My counterpart wasn’t able to sell ten cases over a month.  

The lesson I learned—and use to this day—is that it is all about relationships, customer trust, and sales follow-up to help your retailer.

Michael O’Brien, CEO and Founder of Peloton Coaching and Consulting

I remember my first professional sale like it was yesterday. 

I was twenty-one and a new copier sales representative in Washington, D.C. It was my first month, and during the first three weeks of a hot and humid July, I sold nothing. 

Then I changed my technique and started focusing on my customers’ paint points instead of making the sales process all about me. Not only did my first customer buy one copier, but they also ended up buying a second one on the last day of the month. 

Feeling excited was an understatement when I learned I was July’s salesperson of the month.  

I was nervous about starting my professional career, and my father thought it wasn’t the smartest job to take. When I made that sale, it gave me confidence that I could be successful, and it taught me the most valuable sales lesson: Never make it about yourself. 

Sales professionals are problem solvers, and you can’t solve someone’s problem when your primary focus is on you. It’s a lesson that helped me move up to the executive suite and start my own business.

Josh Jenkins, Director of Business Development at Shapiro Negotiations Institute

My first sale came as a junior golfer cleaning clubs on the 18th hole at the local public golf course. I was only 12 and wanted to buy a new putter but I couldn’t afford one just on my allowance at the time. 

I left that first day with about $10 after asking each person if they wanted me to clean their clubs. In a few short weeks, I was cleaning clubs without asking and waiting around for them to tip me. In modern selling techniques, this would be a combination of the puppy dog close and the assumptive close.

I initially felt insecure about it but it didn’t take long before I was talking with the players while cleaning their clubs. It became an added perk of the course as opposed to a kid being a nuisance at the end of the round. I learned to be confident and to connect with people. While having that conversation didn’t always result in a larger tip, each time I saw them again the rest of that summer we had something to talk about and the tips started pouring in.

Professionally, my first sale at Shapiro Negotiations was with Novamex, the company behind Jarritos Mexican Sodas. I remember mostly discussing how our managing partner was from South America and it always becomes a pet project of the whole office when we support Spanish speaking or bi-lingual clients. 

Again, it was about connecting with the client first, then letting them know of our expertise in their specific field and the benefits their team would see from working with us. Similar to the summer job cleaning clubs, we have gone on to work with Novamex on three separate occasions and are planning additional programs with them!

Charlene “Ignites” DeCesare, Founder of Firewalk Sales

Technically, I’ve been in sales since the age of 16 when I got my first retail job. The first high-stakes sale was when I worked for Gartner Events nearly 20 years ago. My prospect was an executive at a very large technology company. As I entered his office, he motioned me to his desk and said, “Let me show you why this meeting is going to go very badly for you.”

On his monitor was an image of a negative vendor rating that the research arm of my company had given to his company. Luckily, I was able to turn the situation around and close the deal. Ultimately, it came down to my ability to separate research from events while also convincing them that they wanted to proactively take control of public perception via event participation.

I have another story where my boss, listening to my sales presentation, wrote “TOO JOLLY. BE MORE SERIOUS!!” on a notepad in front of me. As someone who practices relationship-based sales, I ignored that advice and closed the deal.

Ben Sardella, Co-Founder and CRO at OutboundWorks

My foster dad used to make the best chocolate chip cookies. Every time my friends would come over they'd ask if we had any.

One day in the second grade, I decided to take a few extra cookies and bring them to school. I handed a few out to my friends and eventually random kids would ask me if I had brought cookies that day.

The next time he made a batch, I brought the whole batch to school and sold them for $1 per cookie. That night my dad came home from work and was so confused, he couldn't believe I had eaten that many cookies in one day.

I learned to build up a little brand, create some demand through a freemium approach, and then when it came time to charge, charge a premium that matches the value/demand. I've been selling ever since.


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