Behind the Betting Totes: Why Working at the Kentucky Derby is the Ultimate Sales Challenge

It’s the most nail-biting two minutes in May you’ll ever experience. There’s a lot of pressure to perform, and the tension and excitement are palpable. The Kentucky Derby? Nope--I’m talking about the two minutes prior to the actual race when betting tote operators like myself are completing trifectas, part-wheels, and win-place-show bets down to the wire for those Derby goers racing to get their final bets placed.  

If you frequent the Roses Lounge or Matt Winn Dining at Churchill Downs, you may have come to my window to place your bet. Every Derby week, I work as a mutuel teller at one of Churchill’s betting windows, and I’ve done so now for more than ten years.  

At first, I signed on for the job as a college kid who wanted to watch the Kentucky Derby live and needed some extra income for the summer. Little did I know that I was signing on for a temp job that would impact my future sales career down the line. 

So why is working a betting tote for one of the biggest events in America the ultimate sales challenge? Let’s break it down.  

You Get One First Impression

If I am known for one phrase in my professional career, it would have to be “You only get one first impression, so make it a good one.” Of course, part of your first impression is appearance (and all the mutuel tellers adhere to a dress code), but I quickly learned there is so much more than simply looking put together on the job.  

When someone comes to bet with you, it may be for just the one-off ticket, or they may be betting with you the whole day. Ideally, you’d like to have repeat betters. How do you do that? By making a good first impression. Smiling, exuding positivity, and making a person feel welcome are what customers notice more than anything else. The same thing goes when you’re looking to have repeat business with clients. Which leads me to my next point... 

Exceptional Service. Every Customer. Every Time.  

On the inside of each betting window at Churchill, for as long as I can remember, we have these little postcards that only employees can see. There’s this beautiful sunset over the downs, and then it has this motto across the sky that says “Exceptional Service. Every Customer. Every Time.”

Exhibiting good customer service is doable. Repeating good customer service for a long, intensive amount of time--sometimes under a lot of pressure--is a real challenge. 

Working in that kind of fast-paced, high-pressure environment at Derby has taught me how important customer service actually is when it comes to sales and recruiting. Never underestimate or devalue what a short interaction can do for a customer’s overall experience.  

Just a few minutes of good customer service can foster a relationship that lasts for years. Talk to some of my regular betters from St. Louis--I think this would have been our 8th year of “making money and memories” together, as they put it. You can then talk to some of the candidates I worked with for two years plus before finding them that best-fit opportunity (waving at one of Beam’s engineers, Josh Boorn, right now). 

There’s No “I” in “Team”

When you sign on to be a temp mutuel teller at Churchill, you get a thorough training in using the totes (fairly simple technology), a clearer understanding how betting works (enough to place your own bet), and the do’s and don'ts of assisting customers (Do help educate people how to place bets correctly. Don’t put out a tip jar).

But on the actual day, you’ll find yourself overwhelmed. You get a seasoned better who’s coming at you with an array of part-wheel bets, and for some reason a tote key is as jammed as your brain is when you’re trying to remember if you counted the right amount of change.

That’s when relying on your team counts. I don’t think people know how large a team it takes to put on the Derby. Churchill has more than 5,000 full-time employees. They then hire thousands more temporary workers to ensure the track can accommodate 150,000+ guests. 

My current employer, Beam Dental, recognizes the value of team in one of its core values, Team First. What this means is going beyond simply acting on your own interests but acting on behalf of the team’s. 

Every employee at Churchill understands what that Team First mentality is. From our tote repair persons being constantly on call to seasoned, union mutuel tellers helping those less-experienced on the line (Betty and Rob, you are the best for answering all my repeat questions) to the wait staff who grab the tellers much-needed water without being asked--everyone plays an important role not only helping customers but also helping each other. That’s what yields a successful result. 

Grace Under Fire

Inevitably, manure isn’t just down in the horse paddock. Sometimes you get a customer’s bets wrong or you’re not able to get all of a customer’s bets in before a race goes off. Maybe you miscount bills when paying out a bet or your tote breaks down. All of these scenarios are stressful for customers and employees alike.  

What I’ve learned working at the track year after year is that you truly should only care about what’s in your control. Which is a fair bit! But there will always be outside variables you have no influence over.  

So take some extra time to count out that change correctly. Don’t be afraid to have a customer repeat a bet even when time is of the essence. And know that sometimes you simply won’t be able to placate an irate customer.  

When you’re able to transfer that same mentality to sales, you make such better progress in racking up wins, learning from losses, and not not letting the small stuff get you down.

Always Be Closing

This motto is quintessential success in business, but what actually goes into closing? Everything I just described on this page. It starts with a great first interaction. It progresses with good teamwork, positivity, and customer service. It ends with a satisfied customer.  

There’s always more you can do to improve your closing skills. In my opinion, it pays (literally and figuratively) to know exactly what you’re selling and have enough empathy to put yourself in a customer’s shoes. 

It took me a while to really understand the nitty-gritty of exotic bets, reading programs, and following horses’ training progress. However by investing the time to learn the ins and outs of the track, I was able to serve my customers better and give them confidence in their purchases. Now, I can’t guarantee a winning bet every time. But I can guarantee an increase in a customer’s own conviction and confidence when wagering at the track.  

Good Odds

Working the Kentucky Derby was just supposed to be a college gig. Why do I keep going back, even when I have an incredible job serving one of the best tech startups in Ohio and the Midwest?

Returning each year to work a week at Churchill keeps my customer service skills primed. I am constantly growing new relationships with people while building new ones. And it is hard to replicate that electrifying feeling of watching one of the greatest races in the world. 

If I ever see that someone has listed experience working at the Derby on their resume, the odds are good they have what it takes to succeed in sales.

Note: Churchill Downs in no way contacted me or contracted me to write this article. The opinions expressed in this article are my own and do not necessarily reflect those of Churchill Downs.