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Former Boot Barn CEO Jim Conroy: Striking Retail Gold in an Internet Age

When Jim Conroy was recruited to be chief executive at Boot Barn in late 2012, the retailer was only in eight Western states with 86 stores.

At the time, he described himself as the No. 2 guy at Claire’s Accessories in Chicago where he served as president and chief operating officer.

“I was recruited to become the No. 1 person at Boot Barn,” Conroy told the Business Journal.

“I took a chance on a much smaller company, but I wanted the opportunity to be the person in charge.”

In the past decade, Conroy and his team worked to make Irvine-based Boot Barn a national name.

“I had the sense that while cowboy boots and cowboy hats are considered ‘Western,’ that was more of a creative descriptor, not a geographic one,” he said.

“I thought there would be more opportunity to take a Western-leaning brand and make it more of an Americana-leaning one and therefore opened the aperture for the customers we could go after and the markets we could open in.”

In a decade where retail outlets have struggled to survive amidst competition from online sites, Conroy lassoed a winning strategy.

He transformed the regional retailer into a national lifestyle brand with annual sales rising five-fold to $1.7 billion. The company has since reached almost all 50 states with 425 stores.

“It was exhilarating,” Conroy said.

“I’ve always enjoyed the tangible nature of retail and how you’re interacting directly with the end consumer on something that’s either very personal or functional. It feels like you have a very direct relationship with the ultimate consumer of your brand or the product.”
The executive aimed to increase Boot Barn stores by 15% annually with the goal of reaching 900 retail locations.

But before he could meet that goal, Conroy got poached by Ross Stores Inc.

In November, he stepped down from Boot Barn to take on the CEO role at Ross Stores. Though he’s exited OC, the Business Journal believes his accomplishments over the past decade are so notable that we named him Businessperson of the Year in the retail sector.

Since Conroy took the company public at $16 a share in 2014, its stock soared more than 10-fold, reaching an all-time high of almost $170 in October. His work was so highly valued on Wall Street that during the trading session following his announcement, the shares fell 20% to $129.38. They have since recovered to $160.34 and a $4.9 billion market cap as of last week (NYSE: BOOT).

“When he assumed the CEO reins 12 years ago, Boot Barn was one of several regional retail chains specializing in western and work products,” Chairman Peter Starrett said in a statement. “His focused approach on the execution of our strategic initiatives has led to one of the most exceptional growth stories in the retail industry.”

Direct Retail Relationships

One of Conroy’s first jobs was vice president, strategic planning at Blockbuster from 1996 to 1998. Having 5,000 video rental stores across the world at one point, it was “an incredibly entrepreneurial company,” Conroy said. “Very aggressive, very fast-moving.”
Afterwards, Conroy led buying, marketing and supply chain functions at Gerald Stevens Flowers & Gifts, which counted 300 locations and multiple sales channels.

Conroy’s interest in the industry eventually blossomed with management consulting for various retail companies, which made him want to get more directly involved with the sector.

He later joined Claire’s in 2007 to better understand the global reach a retailer can achieve.
“What I learned there was the ability to bring small indulgences to a younger customer.

Things that were very affordable luxuries for them,” he said. “You could just see how something could transcend a whole bunch of different national boundaries.
“I think you pick up different pieces from each experience.”

Growth Trajectory

When it came to joining Ross, Conroy hadn’t been looking for a new opportunity.
“For 12 years, I had never spoken to another company,” he said.

He joined the discount retailer, valued at $51 billion, in December and officially takes over as CEO later in February (Nasdaq: ROST).

“At the end of the day, I view the CEO’s role as working through their team to achieve a common success,” Conroy said. “I’m just thrilled with how strong they are and how committed to the company they are.”

Conroy is graduating to an even larger network at Ross as he will oversee 1,836 locations in 43 states and another 356 dd’s Discounts stores in 22 states.

The retailer, based in Dublin, California, reported that revenue in fiscal 2023 climbed 9.1% to $20 billion.

Conroy aims to steer Ross toward even more growth. The potential he sees pertains to not only the main Ross store network but also its smaller brand, dd’s.

“Dd’s has only about 400 stores, but probably has some opportunity to continue to grow that pretty significantly as well,” he said. “I can see a lot of opportunity to grow that business simply by continuing to, if I can, maintain their growth trajectory that’s already in place.”

Best Wishes

“Leadership transcends industries, and I think the ability to assemble a talented team and work with them to achieve successes is the common thread across most successful companies, and I was very fortunate to have that at Boot Barn,” Conroy said. “And it’s early days at Ross but it seems that I will enjoy that same luxury there.”

“Jim is a proven retail executive with a demonstrated record of developing and leading successful retail management teams and creating tremendous value for shareholders,” Ross Executive Chairman Michael Balmuth said in a statement.

Going Back Home

His transition to Ross means a homecoming for Conroy, a graduate of Cornell University in Ithaca, New York.

“My roots are in New York, so it’s a little bittersweet, because I do love it here as well,” he said. Conroy will be based in Ross New York office.­

“I think Orange County specifically has a great blend of sort of successful businesses and entrepreneurs yet also blends in sort of a more casual lifestyle along with it, and I think that that’s been a great balance for me and my family as my kids have grown up.”

“I’m forever grateful for the reception I got into the Orange County business community 12 years ago,” Conroy added. “I was an outsider coming in, and I was welcomed with open arms, and now I’m departing and am getting a very warm send off. So, I couldn’t be more humbled by that.”

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Sonia Chung
Sonia Chung
Sonia Chung joined the Orange County Business Journal in 2021 as their Marketing Creative Director. In her role she creates all visual content as it relates to the marketing needs for the sales and events teams. Her responsibilities include the creation of marketing materials for six annual corporate events, weekly print advertisements, sales flyers in correspondence to the editorial calendar, social media graphics, PowerPoint presentation decks, e-blasts, and maintains the online presence for Orange County Business Journal’s corporate events.
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