Tech CEOs Summer Jobs & Lessons Learned

Job: Fourth grade golf caddy (who was the same height as the bags I carried)

Lessons Learned:  I learned about sportsmanship, client service, competing with integrity, and overall hustle from this first summer job. I also gained an early appreciation for employer perks by scoring a hot dog or Snickers now and then. Finally, this role enabled me to expand my vocabulary thanks to many overheard expletives.

Job:  Concession stand at a summer carnival

Lessons Learned:  I tried to treat every customer like a friend - greeting them with a smile really goes a long way. I also got some tough-love sales experience because if I made the wrong change at the end of the day, it came out of my paycheck. When you end up bringing in less than $2/hr for a full day's work, you get better at math pretty quickly!

Job: Selling Newspapers

Lessons Learned:  I started my career in sales long before I was old enough to drive, and long before I knew it would set me on the path for the rest of my life. My first “real” job was selling vinyl windows and house painting services door-to-door - the original cold calling - when I was 15. But it was my previous job that really jump started my career.

I started selling newspapers door-to-door at 12 years old after I bumped into a guy handing out flyers that said I could make $10 / hour, which was a lot of money for a preteen. I signed on, and received a crash-course packet outlining every possible way a customer could say “no” and exactly how I should respond to flip that “no” into a “yes.” I memorized every page of that packet, and with that knowledge, I outperformed everybody else on my first day.

I spent about three years at that job, soaking up every piece of experience I could. I was getting some of the best sales training of my life at just 12 and 13, and it would carry true through my late 20s when I’d share that same knowledge with the ZoomInfo sales team. At that age, I wasn’t planning on going into sales as a career, but in hindsight, I see how influential a middle-school job was on the rest of my life.

Jobs: Retail & Lifeguard

Lessons Learned:  My first job was working in retail (at a soccer shop)…oddly that was inside a Ski Store in Massachusetts so foot traffic was not very high! I think I spent my entire paycheck in the store as it was one of the few places you could buy cool gear without doing mail order catalog at the time (yes that makes me feel old). I learned a ton as the operations were quite small so inventory management, sales, customer service were all responsibilities on a given shift. It also taught me that working on something you are passionate about makes work “easy." It never felt like a job.

My other summer job was as a lifeguard at a local pool / golf club. It gave me perspective on caring and being responsible for people, especially kids that were the most at risk. I also got my first opportunity to be a people manager as a lifeguard, learning scheduling, compensation matters, performance, and conflict resolution. Funny enough, I also became the manager of my future wife…probably the last time I was truly the “boss” in our relationship!”

Job:  Herman’s World of Sporting Goods at the Walt Whitman Mall in Huntington Long Island NY. I worked in the shoe department where the popular brands at the time were Nike Air Jordan’s and Hush Puppy Golf shoes. I appreciated my employee discount which enabled me to own Champion sweatshirts in every color which were all the rage in the eighties.

Lessons Learned:  The job was fast paced with constant foot traffic so I really had to hustle to keep up and provide good service. We had quotas to hit and I enjoyed the team aspect of working together to exceed them. This is where I first learned that company success requires each member to do their part and that great companies can only exist if you have great people.

Jobs:  Camp counselor in Bourne (Sagamore Beach) and worked in the kitchen of a local diner called Blueberry Muffin

Lessons Learned:  Both were fun, but working in a restaurant definitely taught me work ethic.

Job:  Helped the Boston Public Market build their website when they were still on the bridge between downtown and Seaport.

Lessons Learned:  That got me into building for the web.

Job:  Worked at a telescope in Westford (MIT Haystack Observatory) for the summer.

Lesssons Learned: This was where I first learned to code so I was able to analyze data.

Job:  I spent my summers in Maine throughout my childhood, and when I was 12, I started bailing boats at the local campground/marina. For the next 8 summers, I picked up the trash, hauled the sewage to the dump, and worked into boat rentals, sales, repairs, fuel dock management, and client-facing roles. I got the opportunity to deliver mail by boat and take tourists on rides around the lake as passengers. After my senior year of high school, I began running the marina with my brother and continued to do so throughout my time at the University of Maine.

Lessons Learned:  My experience at the marina was eye-opening. Not many people have the opportunity to witness a business’s inner-workings so closely at such a young age, but, at age 18, I saw that running a business is challenging yet doable if you work hard and use common sense. And while I quickly found out where every rock was hidden on Great Pond and became acquainted with the intricacies of working 7am – 6pm with my younger brother, I also learned the importance of connecting with people, whether they be customers or teammates. The campground/marina was my first experience dealing directly with customers, which was the first step in informing me how to sell—a skill I’ve used in every position since.

Job:  Working at the Sofitel Hotel in Toledo, Ohio.

Lessons Learned:  While there, I did just about everything – bellhop, concierge, front desk, event planning, hotel maintenance… you name it. It was an amazing experience, and I learned that I love working with people. I learned that I love a job with variety and a lot of change. And above all else, I learned to show up every day ready to tackle each opportunity in front of me, because when you do that consistently, good things unfold for you.

Job:  My first summer job, at 15, was to wire my entire high school with Ethernet. Back then, and I am definitely aging myself here, the only internet access we had was in the computer labs.

Lessons Learned:  I can still clearly remember boxes upon boxes of cable, cutting them and testing every... single... piece. I learned pretty quickly that cable quality and attention to detail were extremely important. If I used a faulty cable, I’d have to start all over again, which, as an impatient teen, wasn't exactly the most exciting task to undertake repeatedly.

Nevertheless, I persisted and by the end of the summer not only was the school fully wired, but I received my first real paycheck. I saved enough money for my first ‘big boy’ purchase - new skis! Fun fact, I still have them in my garage!

Job: Bartender

Lessons Learned:  I worked as a bartender at a local pub. Now, being a bartender in general is an often-difficult job, but in Ireland, it’s an especially demanding role. It was a minimum-wage job that shaped how I work and interact with people from all walks of life in an extremely high-pressure environment. Working at this fast-paced job also forced me to sharpen ‘think on my feet’ skills, but most importantly, it provided a very valuable and solid foundation of customer service on which I used throughout my career and still heavily rely today.

Job: My first summer job was caddying at a local golf course. I was 11.

Lessons Learned:  One thing I learned is that it's important to understand whether you're paid for time or outcomes - and act accordingly. I would get to the course around 5:30am, because I knew two things:

1. The people playing at the start of the day would play a round in about 90 minutes less than those later on
2. We were paid by round, not by the hour

Of course, golf is a tough game. So I also learned more ways to curse than I can even recall today. But that has been less useful in business.

Job: Sailing Instructor - For several summers I worked as a sailing instructor for 8-12 year olds on the Jersey shore. Probably the most personally rewarding job I’ve ever had.

Lessons Learned:  Literally 100’s of lessons learned…

Imagine an 8 year old sitting at the tiller (steering stick) of a small sailboat. The boat is stuck (or going backwards), rocking unsteadily in the chop, the sail is flapping noisily overhead, the boom (the long pole at the bottom of the sail) is swinging back and forth threatening to hit you in the head, lines are rattling against the side of the mast. Other young voices are offering misguided advice – “push it, pull that”. Overwhelmed, everything is scary, nothing makes sense, and tears start to flow.

The miracle of small people is how resilient they are. Pull up alongside, be calm, reassuring, slowly help them orient, unpack what they already know and apply it. And then suddenly it’s a sunny day again, its almost fun, they are doing it.

If you aren’t afraid of the worst case, then none of it is worth getting upset about, which is why we did capsizing drills. (which were feared and then loved).

Taking care of a boat, even a small one, is work, which is why keeping it fun, light-hearted and competitive were crucial.

There is possibly nothing more hilarious to an 8 year old and their pals than publicly insulting your underwear brand choice (thanks to a waistband that temporarily exposed itself). There is also nothing more fun than an all out water war, where kids are equipped with small sailboats, buckets and hand pumps in sail boats and sailing instructors have the “club tub” (a power boat) and an electric bilge pump.

Jobs: I had two  summer jobs (I was 15, about to turn 16) - one half of the summer was spent caddying at a local country club in Geneva, Switzerland; the other half was spent working in the back-office of a trading desk at a bank.

Lessons Learned:  Caddying taught me the importance of customer service and the very direct correlation between good, attentive service and the size of the tips I received. I also learned first-hand the importance of tailoring communication and management to each person. We had a wonderful “manager” with 40 years of experience who treated each of us caddies with empathy and individualized attention … so many of the caddies came back every summer, made more money and provided ever better service as a result.

At the bank, my desk was behind a woman who had been at the bank for many years. Her job consisted of double-checking amounts from two giant piles of computer print-outs for all the trades, manually, with a box of pencils. She looked at the clock more than anyone else in the office and vocally hated every minute of her job. She made sure to tell all the interns and younger people to study hard and work hard early so we would not end up like her. Ticking amounts from these two piles was her entire job, all day every day, and served as a huge kick in the butt to do very, very well in school. I owe her a lot for sharing her wisdom at a time I needed it.

Job:  I grew up in a very small town south of Albany, NY, which at the time, was only about 1,000 people. One of my first summer jobs was mowing lawns.

Lessons Learned:  I responded to an ad I saw in the local paper and quickly got about 5 customers for the first summer. These weren't huge lawns so I was behind a push mower the whole time, but it taught me about putting in the work to make money and it also made me realize how important reference customers were. If I do a good job, they'll help me make more money by referring me to others.

Throughout high school, I leveraged these happy customers as referrals to help build my college fund, gradually building to bigger and bigger lawns enabling me to make more money.

One funny moment is  when one of my customers had a riding mower and they were willing to let me borrow it to cut other lawns, which is exactly what I did for a few months, driving the riding mower 2mph on public streets from house to house. Little did I realize until I took a step back that going as slow as a turtle on public streets from house to house was way less efficient than it would've taken me to just drive to the next house and use a push mower so eventually I went back to the push mower routine. Those were some good lessons learned during high school.

Job:  One of my earliest jobs was being a waiter. First at a truckstop diner attached to a gas station in South Dakota and later at a nice Italian restaurant. 

Lessons Learned:  This taught me a number of lessons, the biggest one was that I was getting paid directly from each customer based on how well they thought I performed my role (my base salary was $2.13/hr, so all the income was tips).

Prior to this, hourly work flipping burgers was drudgery, but after a couple of weeks waiting tables, I realized I could make way more money in less time by being excellent at my job. Knowing the specials and wine list well, having thoughtful menu suggestions, always being happy and helpful, and anticipating customer needs earned me good tips and hooked me on getting paid for performance instead of time served. That experience stuck with me to this day - to always focus on outcomes over effort (especially customer outcomes). It's no surprise that one of our core values at Perch is "Obsess over the customer!" Other learning: only eat at a restaurant attached to a gas station as an absolute last resort. ;)

Job:  Data Entry

Lessons Learned:  A neighbor of mine sold consulting services to the government, and she'd develop her sales pipeline by sending direct mail flyers out to state officials across the country.

At the time (summer of 1999) none of these records were digitized; my job was to transcribe records from a big book she had into a database on her computer.

I got paid by the record so I ended up making good money. I spent most of my time on the job thinking about how I could build an Optical Character Recognition (OCR) scanning system that could automate the job.

I never got there but did develop mild carpal tunnel syndrome.

Jobs:  My first summer job was playing guitar for a Jewish Home for the Elderly. I would go to each floor and do a 45 minute guitar/singing session of old classics - 5 floors total.

I would also sub in for "exercise" class and lead that too for them when someone was out. I did that for 2 summers in a row - Freshman and Sophomore years.

Lessons Learned:  I learned a lot about patience and also the power of personal connection (which is a huge part of why Alyce came to be).

Job:  I spent my summers (and weekends in spring/fall) refereeing soccer games, eventually going so far as refereeing D1 college games and the youth national championships.

Lessons Learned:  It certainly was good training for fast-paced decision-making amid competing (and sometimes very vocal) interests!

Job:  Mowing Lawns

Lessons Learned:  Other than “never let someone on your crew put poison ivy in your work boots... I received countless life lessons during those two summers:

Be on time. You’re meeting the crew at a designated spot. As everyone has a specific role on every job, if anyone is late, the crew can’t leave. Everyone has to wait until the full team is there.

Push through the hard times. July and August is a tough time to cut lawns and do yardwork. There were 10 day stretches both years where temps exceeded 100 degrees. Suck it up. Do your job.

The importance of planning: You need to plan and be organized. Did you bring multiple water bottles? Ice? Lunch? Back up pair of socks for those really hot days? If you forget any of the items you need to get through the day, you just made your day much harder and more unpleasant. Worse yet, if you need to stop at a convenience store to buy what you should have brought, you’re slowing the crew down.

Selfcare: If you don’t take care of your body, stay hydrated, take breaks when needed, stay out of the sun when possible, you cannot do your job to the best of your ability. It also helps if the night before you don’t go big on a night out with your buddies and have to battle through a long, hot workday nursing a hangover. I made that mistake way too many times.

Attention to Detail: Do your job to the best of your ability: Cutting. Weeding. Planting. Edging beds. Do the right thing the right way. Take pride in your work. The details matter.
Stuff happens. Deal with it: If it rains a couple days in a week. Guess what? You’re working longer days to catch up, and Saturday, to get your scheduled jobs done. Suck it up, buttercup. No need whining and complaining about it. No one cares.

How you treat people matters: Fellow crew members. Customers. Everyone. Do what you say you’re going to do. Help others whenever possible. Be accountable when you make a mistake. You earn or lose trust with what you do, and how you treat people every day.

And again, don’t take off your work boots during a lunch break on a really hot day, and walk back to the truck for 5 minutes. You never know what will be crammed into the toe of your boots.

Job: Flipping hamburgers at McDonald's

Lessons Learned:  I worked at McDonald's in Yonkers New York during the time they were building out drive-throughs. I certainly got teased a lot throughout my time working at McDonald's and made a lofty $2.30 an hour. But I did really enjoy cooking the hamburgers and found myself getting competitive in terms of the speed at which I could cook burgers. The skillset involved flipping a spatula over one way to flip a burger, then keeping the spatula upside down and flipping it right side up to flip the next burger. That way you would not waste any time flipping the spatula back to its original position. During this time I always dreamed of attending McDonald's hamburger university in Chicago.

Some key takeaways were learning about making commitments. Part of working is being reliable and showing up on time and working the hours you are supposed to work. Also, practice makes perfect. You get better at something as you continuously do it. The flipping hamburgers for example started off slow, then you find a means to speed it up. You could start to calculate how long it took you to make a number of burgers, then measure productivity and growth based on how long it took you the next week. Measuring productivity really gives you the means to improve upon it. Carry all experiences forward in a positive way. Don’t look back on how terrible flipping burgers was but rather all the core skills it taught you to get you to where you are today

Fast forward to being a partner at Ernst and Young where McDonald's was a customer of ours and I had the opportunity to go to Hamburger University to speak with them finally.