Simplify Fundraising with Custom Team & Corporate Apparel Stores

May 15, 2026

Share this article

Group of people in teal shirts walking arm-in-arm through a grassy field at sunset

Anyone who has ever organized shirts for a school team, fundraiser, booster club, or company event knows how quickly it can become overwhelming.


Collecting sizes. Chasing down payments. Sorting through boxes. Managing spreadsheets. Handing out orders.


It’s a lot.


Trailhead’s custom online apparel stores are designed to make the process easier for the people organizing it.


As Matthew Nardozza explains:

“We’re taking away all the extra work for them.”



— Matthew Nardozza, Founder

Instead of collecting paper forms and cash, organizations get a simple online store link or QR code that people can use to place their own orders directly.


That means less stress for coaches, PTO volunteers, HR teams, and event organizers.

No More Collecting Orders Manually

Traditional apparel orders usually require one person to coordinate everything:


  • collecting payments


  • organizing sizes


  • building spreadsheets


  • placing bulk orders



  • distributing items afterward


Trailhead simplifies the process by handling the ordering system for you.


Customers place their own orders online, choose their own sizes, and pay directly through the store. Once the sale closes, Trailhead handles production and organization behind the scenes.


For fundraising stores, we also track total sales and coordinate profit-sharing payouts directly with the organization.

Orders Organized and Ready to Hand Out

One of the biggest headaches with traditional group orders is distribution. Usually, someone ends up digging through a giant box of mixed apparel trying to match orders to names.


Trailhead does things differently.


Each order is individually packed, labeled with the customer’s name, and organized in a way that makes pickup and distribution much easier.



As Nardozza explains:

“We individually wrap every order with that person’s name on it and organize everything so it’s easy to hand out.”


— Matthew Nardozza, Founder

That extra organization saves customers a huge amount of time.

Bear holding a phone and papers between a cluttered office and a tech-filled digital side, with boxes and files

Make Group Orders Easier on Everyone

Bulk apparel orders often involve guessing how many sizes to buy upfront, which can leave organizations stuck with leftover inventory they don’t need.


With custom online stores, products are ordered individually, so organizations only purchase what customers actually want.


That means no extra boxes sitting in storage after the fundraiser ends.

Make Group Orders Easier on Everyone

Fundraisers, team stores, and company apparel orders don’t have to turn into a second full-time job.


Trailhead helps schools, teams, nonprofits, and businesses simplify the entire process — from online ordering to packaging and distribution — so organizers can spend less time managing spreadsheets and more time focusing on the people they’re supporting.


Whether you’re running a school fundraiser, organizing employee apparel, or setting up gear for a local team, we’re happy to help build a process that works for your group.


If you’re planning an upcoming apparel order or fundraiser, reach out and we’ll walk you through the options.

Frequently Asked questions

  • How do custom apparel stores help with fundraising?

    Customers order directly through the online store, and Trailhead handles the ordering process, production, and organization. After the store closes, fundraising payouts are coordinated with the organization.

  • Do we have to sort all the orders ourselves?

    No. Every order is individually packaged and labeled to make distribution simple and organized.

  • Do we need to buy inventory upfront?

    No. Orders are placed individually through the online store, so there’s no need to guess quantities or store leftover apparel afterward.

Recent Posts

Two tiny storefronts on a blue seesaw, one red-and-white, one blue-and-white, against a light background
May 8, 2026
Stop paying hidden fees for poor service. Learn why partnering with a local print shop like Trail Head offers better value and expert advice.
Exterior of Trailhead Printing storefront in Simsbury, Connecticut, featuring signage
May 5, 2026
Is Trailhead Printing the best local print shop in Connecticut? Learn how this Simsbury-based shop built a reputation for reliable service, affordable pricing, and consistent 5-star reviews.
Fun fact card with a bear DJ and a note about the @ symbol, on a dark green background.
April 30, 2026
DJ Sims shares a fun fact about the first website from 1991, which is still online today and started it all.
DJ Sims the bear dressed as an accountant, wearing a suit and visor, holding a calculator and ledger
April 9, 2026
DJ Sims from Trailhead Printing shares a fun fact about how the @ symbol became popular through email.
high visibility apparel for work
By Matthew Nardozza April 3, 2026
Stay Seen, Stay Safe: The Ultimate Guide to High-Visibility
Small Business storefront in Connecticut
March 16, 2026
Affordable marketing ideas for Connecticut small businesses. Learn five simple ways to promote your business using community events, partnerships, and print.
Fun Fact #1 of Fun Fact with DJ Sims of Trailhead Printing.
March 10, 2026
DJ Sims shares a fun printing fact: early printed books didn’t include page numbers, so readers had to write them in by hand. Learn a quick piece of print history.
Screenshot of Trailhead Printing’s online apparel ordering portal where users can upload artwork, ch
February 13, 2026
Trailhead Printing now offers a fully custom online apparel ordering portal. Upload designs, get instant quotes, and order locally in Simsbury, CT.
Custom business cards at Trailhead Printing in
February 3, 2026
Trailhead Printing in Simsburt offers high-quality, affordable custom business cards with fast turnaround. Design your cards and print with a trusted CT print shop.
Side-by-side price comparison showing the cost of printing 175 full-color 24x36 blueprints: $997.50
January 20, 2026
Save hundreds on blueprint printing with Trailhead Printing in Simsbury, CT. Same high-quality plans as big box stores—at a better price. Get an instant quote today.
Show More