Business Page: 10 Years In, It's Smooth Sailing For Mainsail Events And Marketing

Jenn Allard knew it was time.

After more than a decade coordinating and managing events at Chatham Bars Inn, the Eastham native and longtime Orleans resident was ready to strike out on her own. But the move didn’t come without some sense of trepidation. 

“I didn’t really have a plan,” she said. “It was just time for me to move on. And some of my colleagues were really pushing me, like ‘What is it (that you’re going to do)?’ I had to figure it out.”

Leaving the security of an established business was a gamble, but fortunately she got the blessing she needed from her mentor, Paul Zuest, who had just ended his tenure as the inn’s general manager. She told him her plan, and his response was succinct.

“Perfect,” he said.

“Honestly I will never forget that day,” Allard said of the exchange. “It changed how I felt about it.”

Fast forward 10 years, and Allard is sitting in the offices of Mainsail Events and Marketing, the company she launched after leaving the inn. Tucked away just behind the North Chatham Post Office, Allard leads a small team and works with an extensive list of vendors and contractors to plan and host events for organizations both locally and nationally. 

Allard said she never had designs on a career in event planning while growing up, even though she was always the one amongst her friends to coordinate and make plans. Instead, she studied theater in college with hopes of making it on Broadway. 

In the early 2000s, she found herself managing a teen center when she decided she needed a change. She took a job in reservations at Chatham Bars Inn for what she thought would be the summer.

“And I just kept moving up from reservations,” she said. “I did marketing, I did events.”

Then Zuest approached her with a specific assignment. He wanted her to take the reins on an event being held by a local nonprofit.

“I don’t even remember who the nonprofit was, but he said ‘We always do their event, and we give them the space for free, but they don’t know what they’re doing. You tell them how they’re going to run their event.’ I was like ‘But it’s their event. Why would I be telling them what to do?’”

Little did she know at the time that the opportunity would help lay the groundwork for her next endeavor. Allard started Mainsail Events in April 2015, and while the company organizes events for clients of all kinds, it has garnered a particular reputation for its work with nonprofits.

“There are so many nonprofits on the Cape that have well-meaning, well-intended and passionate boards and committees, but they need help with organization,” she said.

Mainsail’s local clients include the Atlantic White Shark Conservancy, Housing Assistance Corporation, the Cape Cod Fisherman’s Alliance and AIDS Support Group of Cape Cod. The company organizes everything from galas, 5K runs and auctions to the occasional wedding and events of all sizes in between. In recent years, the company has also run events at the Rock and Roll Hall of Fame in Cleveland and others for a client in California.

But Mainsail’s strength lies mostly with its local connections, said Allard, who is a member of the Orleans, Chatham and Cape Cod Regional chambers of commerce. 

“Obviously that cultivates relationships, but in terms of vendors, we are a really small community,” she said. “I try to share the love with vendors because you don’t want to put all your eggs in one basket. There are some really great vendors to work with, and when they are supportive of you, you want to be supportive of them.”

Working alongside Allard is Jen Sprague, the company’s senior event planner. Sprague worked for years at Mainsail as a contractor before joining the company full time three years ago. The duo are joined by a part-time employee, Mackenzie Holmes.

“I’ve always been a community oriented person, so going and having the opportunity to be part of little niches throughout the Cape and help them grow, it’s great,” Sprague said.

As Mainsail rolls into its 11th year in business, the company is getting some well-earned recognition for its work. Cape and Plymouth Business Magazine included Mainsail on its list of local businesses to watch in 2025. But as she looks ahead, Allard said she’s mostly looking forward to continuing to support the local towns and businesses that have continually supported her over the years.

 “I’m so grateful,” she said. “I feel like so many people have been supportive of me, and that’s amazing. I’m happy and proud of the work that we’re doing.”