With fall in full swing, we’re gearing up for our annual Pie in the Sky bake sale…and we’re looking for pie sellers! In its 29th year, we rely on an army of 500+ pie sellers to help raise critical funding that will allow us to feed thousands of critically and chronically ill individuals and their families across Massachusetts. With a variety of pies on the menu – apple, pumpkin, pecan, and more – each pie provides one week’s worth of meals for a Community Servings client.

A pie seller veteran, Matt Kurkowski has years of experience peddling pies virtually and in-person. We asked Matt several questions about how he got involved with Pie in the Sky, what makes a good pie seller, what he’s looking forward to this year, and his favorite pie flavor.

How did you get involved with Community Servings?

It was almost pure chance – I was working at Zipcar at the time and responsible for writing the member newsletter, which one week in 2008 included a call for volunteers to help deliver boxes for the Pie Box Party. Seeing the need was somewhat urgent, I thought—why not sign up myself? It took all of five minutes reading about CS on the website to convince me this was an organization with a big heart and even bigger mission.

What makes a good pie seller?

The good news is—anyone can be a great pie seller! I’ve found the key to success is experimenting and learning what works best for you personally. Some people like the traditional approach of selling in person to friends and family while others branch out and sell entirely to new people online.

The key is to just get started and not overthink it. I’ve been doing this for 10+ years, but every year, selling that first pie is the hardest. It’s like a warm-up, even with years of experience you need that first sale to get back your pie-selling muscle memory but once you do, every one after that gets easier and easier.

What’s your favorite part of the pie sale?

My favorite two days of the year are the days around Pie Central. I usually help out picking up pies from our partner restaurants the first day, then do the whole process in reverse the next day delivering quality-checked-and-packed pies out to the pick-up sites. I rent a van and at this point have a whole kit I’ve honed for the day—Sharpies to mark boxes, extra phone chargers and batteries (GPS is a drain!), a hand truck and a solid playlist top the list.

It’s my favorite part of the sale because it’s a chance to meet all the people in the community who help support Pie that you don’t see during the day-to-day: the bakers, the restaurant owners, the pick-up site captains and tons more along the way. Just like the CS staff and seller volunteers, their genuine, see-it-on-their-faces gratitude to be involved in such an undertaking makes me happy in ways few other things do.

Why should others become a pie seller?

I often look back on that day when I first decided to give it a shot and help out with delivering boxes—it felt like such a small, new thing to try at the time that I almost thought nothing of it, but I’m not exaggerating when I tell you it fundamentally changed my life for the better. (I well up now even writing this.) The sense of purpose and satisfaction in seeing the work you do help and benefit others has no substitute; it’s one of the greatest joys I’ve come to look forward to every year. When the sale is wrapped up, and the numbers are read out and you know you helped put food on the table for those who will need it all year, it’s hard not to feel proud and deeply satisfied knowing the work you did will have an incredible impact on someone else’s life for months to come.

And on top of that, I’ve made so many friends and connections along the way, people I likely would have never met if it weren’t for Pie. Volunteering is the great equalizer—I can remember being just a year or two into my professional career and sitting in committee meetings having my voice and thoughts heard alongside people who were at the peaks of their professions, out from the c-suite to sit side-by-side with other volunteers to bring this whole crazy idea to life. You’re all there for the common mission and it deepens your faith in the power of teamwork and the goodness of others in your community.

Do you have any tips or tricks for new pie sellers?

When it comes to getting started, I’ll borrow a few words from Nike: just do it. Don’t overthink it, don’t doubt yourself, don’t even consider the reasons why not. Just sign up for a volunteer shift; complete the form to be a seller; get your page set up and ask for your first sale—even if it doesn’t go perfectly, you’ll build just a bit of momentum that’ll build on itself. There’s a whole team of volunteers and the CS staff that have mastered the art of making sure you’ll be successful, so there’s no reason not to give it a go. If you avoid that moment of pause that lets doubt in by moving quickly and just following one step after another, you’ll suddenly look back in ten years and wonder how you ever spent the fall doing anything else.

What’s your favorite pie flavor?

Hands down: pecan. (If the filling is firm enough, skip the fork and plate all together—there’s benefits to a slice of pizza and a slice of pie looking so similar…)

Sign up to sell pies!

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