Leading with Heart

In Focus
NAME:Sarah Eustis
COMPANY:Main Street Hospitality Group
POSITION:CEO
LOCATION:Stockbridge, US
The CEO and Founder of Main Street Hospitality Group, Sarah Eustis, took the company back to basics to refocus on the ‘why’.

Having built her early career in retail, Sarah Eustis took over the family business in 2012, and founded hotel management company Main Street Hospitality Group in 2014.

“We had three hotels in the family at the time. And while we didn’t have a centralized structure, we had a strong culture of brand recognition, social and relational capital and a robust guest base,” Eustis tells The CEO Magazine.

As owner and operator of some of the most distinctive hotels in the Berkshires (including the iconic Red Lion Inn at Stockbridge), the company delivers through its commitment to genuine hospitality, service and management, while keeping a connection to community.

“Ralph Lauren would show up to meetings. We didn’t have focus groups, we didn’t have brand books. But we knew what the identity of the company was through working directly with him.”

“When I came back to the business in 2012, I thought: ‘What could we do with this? Could we build something from what’s kind of our special sauce, that has been developed through our family at the Red Lion?’” she says.

Since then, the Massachusetts-based independent hospitality group has grown thoughtfully and has recently opened its eighth property – Canoe Place Inn in Hampton Bays, New York – with its portfolio located throughout the north-east. Three new projects are planned for 2023.

Shopping Her Leadership Style

Eustis draws on the many years she spent prior working in large retail environments – from GAP to Limited Brands to Ralph Lauren – and the insights and inspiration she took from her experience.

“I didn’t realize it at the time, that working in those companies formed me, in terms of how I think about running my own family business,” she says.

A standout time was watching how Ralph Lauren grew his business.


“Main Street Hospitality, as our hotel management partner, was invaluable during our planning and construction period, working seamlessly with our project management, engineering, design and contractors to create an incredible hotel that will leave an everlasting impression on Hammetts Wharf.” – Colin Kane, Principal, Peregrine Group

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“Ralph Lauren would show up to meetings. We didn’t have focus groups, we didn’t have brand books. But we knew what the identity of the company was through working directly with him,” Eustis says.

It’s this clear vision for the brand and company that is key to moving a business forward, and is something she has adopted in her own leadership style.

“I would probably use Ralph Lauren as a standard bearer of how to grow your company to be globally influential and huge, and still protect the brand very, very carefully. And that’s what I am trying to do,” she explains.

Perfect Partners

These early interactions with successful business leaders shaped her way of leading, and she’s also passionate that everyone in the company understands the ‘why’ behind the business.

“It was kind of a way of thinking about leadership, and about making sure that the why of what you’re doing is very much on the forefront for everybody all the time,” she says.

“There were days when I woke up, and I just wasn’t sure if we were going to stay in business. And that is terrifying, and then also extremely clarifying.”

Main Street will turn 10 in 2024, and Eustis enthusiastically describes the company as a “work in progress”, though it has grown enough to be selective around projects and who it partners with.

“We’re highly selective about the mission of the project, the quality of the partner, the solidity of the economic foundation of whatever the project is, and the potential for positive impact on the community. Which is now a non-negotiable for us,” Eustis explains.

Back to Basics

When the COVID-19 pandemic clipped everyone’s wings in 2020, hospitality took a hit, and the pandemic caused some permanent changes to the way Main Street operates.

“There were days when I woke up, and I just wasn’t sure if we were going to stay in business. And that is terrifying, and then also extremely clarifying,” she admits.

“This is going to sound so cliché, but it cut out all the noise, immediately. And it took us down to the studs.”

But the most important shift for the company was its people.

“It just honed my focus on who. People demonstrate who they really are when we’re in a crisis. And some of the folks really shone and dug in, and some didn’t,” she says.

“People demonstrate who they really are when we’re in a crisis.”

Surviving the pandemic allowed Main Street to restart afresh and change the way it operates.

“We realized who we really are as a company and what matters most to us. We shifted even more to an employees-first mindset,” she says.

Again, it all came back to the ‘why’ for Eustis, and ensuring her people were clear on this – something that was realized through communication and leadership.

“In order to attract and retain really good people, and build a culture, you have to talk about your culture. You have to give people the why. You have to make sure that they are heard, and that they have a feeling of value in your organization,” she explains.

Eustis admits that the pandemic was a big wake-up call, and it made the company revisit its value system.

“The pandemic kicked us in the pants a little bit to do things that we needed to do anyway,” she says.

Shared Values

The whole hiring process at Main Street has now changed, and it operates a 360-degree buy-in for all new hires.

“For example, whether we’re hiring a general manager or we’re hiring a desk agent, there is a group of very selectively chosen people, both who will work with this person, for this person, and who will supervise this person. And they’re all part of the interview process,” Eustis says.

It’s a process that builds accountability for the hire – and it’s working well.

“We don’t talk about feelings enough; we talk about performance.”

“People feel like, ‘Wait a minute, I’m accountable for their success as well, because I was part of the process, and I voted to hire them’,” she says.

The review process works in a similar way, with colleagues asked to talk about how they feel about working with each other, not just how someone does their job.

It’s a bold leadership move and something Eustis believes other industries could learn from the hospitality sector.

“We don’t talk about feelings enough; we talk about performance. Maybe this is coming from a third generation female CEO who’s been brought up in a family of female leaders,” she says. “But the notion of looking at emotions in how the business works, and how communication works, is something that we spend a fair amount of time on.”


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