Why the Big South chose to bet on Sherika Montgomery in evolving college sports world

If it feels like Sherika Montgomery is at home — moving through the Big South Conference offices in Charlotte with an enviable ease — it’s because she is.

The modest desk in the lobby she worked at as an intern is still standing. So is the corner-adjacent office she occupied for years afterward.

She left to work in the NCAA briefly. She served as a top official at the Missouri Valley Conference for a few years after that. But as she walked through the blue-painted hallways last week, it’s clear her professional life started and has since flowed through this place — that something more brought her back here.

“I oftentimes say I stepped directly off a basketball court and into the conference office,” she joked on Monday morning. She added, “It feels like a homecoming.”

It’s a momentous one, too.

Montgomery, 36, was named commissioner of the Big South Conference in April, a few months after Kyle Kallander announced his plans to retire after 27 years in the role. She is now the fourth commissioner of the 40-year-old conference, the first woman and Black woman commissioner of the conference — and one of only two Black women commissioners in all Division I college athletics. (Sonja O. Stills is the commissioner of the Mid-Eastern Athletic Conference.)

“To be the first woman and first woman of color as fourth commissioner, it’s a tremendous honor, a tremendous blessing,” she said. “But I think it’s also a testament to the commitment of diversity, equity and inclusion — but also just the diversity of perspective — within our conference.”

Montgomery has been appointed as commissioner at an unprecedented time in college sports, no doubt. But in an era of membership realignment and transfer portal anxiety and NIL legislation and everything else, her goals are what they’ve always been: to “engage, educate and elevate” her membership, she said.

Kallander, her predecessor, has the utmost faith in her.

“The very first time I met her, I just knew there was something different about her,” Kallander said. “I just knew that she would progress in this business rapidly and really become a leader in the industry.”

Why, exactly?

“Because of her,” Kallander said. “Because of her way of working with people, her understanding of the business and what’s important, her commitment to the student-athlete, and the fact that she knows the Big South Conference — I think that’s really important.”

Montgomery’s move that ‘changed her life’

Montgomery’s ascension to the Big South commissioner’s seat made sense considering her story.

The 36-year-old commissioner grew up in the 1,000-person town of Plantersville, Mississippi, just down the road from Tupelo. She describes an idyllic childhood in many ways: blues and gospel music playing in the house, her and her brother clanking shots off a basketball hoop in her driveway, her father cleaning the family cars to make sure they were pristine every weekend. Her father worked in manufacturing, and her mother worked with the Tupelo Public School District.

Montgomery was always tall — she’s listed at 6-foot-2 in the last media guide she appears in — and basketball talent ran in her family. She was a star at Shannon High School before becoming a first-generation college student when she joined the Memphis women’s basketball team in 2005.

But it was after her freshman year there — when she requested the right to transfer (back before the transfer portal) and ultimately landed at Gardner-Webb — when her professional possibilities came into view.

“I say it often: Being a transfer student-athlete really changed my entire career, and probably my life,” Montgomery said. “It was when I transferred from the University of Memphis that really made me understand my student-athlete experience off the court, out of the classroom.

“What does this blue disc mean that says ‘NCAA’? What are the 8,500 bylaws that I’m governed by, that I’m not really familiar with?”

That freshman-to-sophomore summer, as she tells it, fueled her fascination in college athletics. It fueled it for the world of “compliance,” specifically.

After her final year playing at Gardner-Webb, she interned for a year at the Big South offices and then spent seven years as a member of the Big South staff, mostly as an assistant commissioner for compliance and senior woman administrator. She can still recall the days of “miscellaneous expenses” and “cost of attendance” — the buzz words of college sports administration in that 2013-14 time-frame — and she talks about them with a joy that’ll surprise you. (“That was a huge transformation in college athletics,” she said with a smile.)

She’d go on to work at a variety of places after her seven-year stint in the Big South. Among those roles include at Winthrop as assistant athletic director and in the NCAA’s enforcement department.

“She was destined to be a commissioner of a Division I conference,” said Tom Hosty, her direct supervisor for a few years when she worked at the NCAA. “I mean everybody saw it when she was working with us.”

John Duncan, another supervisor of hers at the NCAA, concurred. Her charisma extended beyond the corporate office, too, he said.

“Sherika was involved with some of the committees focused on women in athletics, and she was a supporter of the Woman of the Year award,” Duncan said. “I used to bring my daughter to the Woman of the Year award celebration, especially back when I was here in Indianapolis, so Sherika got to know my daughter through that. She was always very supportive her, which meant a lot to me and also my daughter.”

Becoming Big South’s commissioner

Her chance to become commissioner arrived in the winter of 2022, when her former boss and the conference’s most steady fixture (Kallander) announced his plans to retire.

His departure, it turned out, fell in the midst of a changing-of-the-guard in conference commissioners across the country: Think Jim Schaus of the Southern Conference, who retired in February. Or Doug Elgin of the Missouri Valley Conference, or Craig Thompson of the Mountain West and others.

It was clear, in other words, that the Big South’s new leader was coming at a critical juncture for the league and in college sports.

And Montgomery stood out above everyone else.

“She has a unique and well-rounded perspective, being that she’s worked in all three levels — institutionally, conference and the NCAA — and I think that’s going to bring a different expertise,” said Meredith Paige, a rising junior on the Radford volleyball team.

Paige was one of two students represented on the committee to find its next Big South commissioner, and she was struck with how in-tune Montgomery was with the college athlete experience.

“And I think that’s important because these past five years, and the five years to come, are going to be the most change that the NCAA and college sports have seen — ever,” Paige added. “With all the dramatic changes that are occurring, I feel really strongly that there’s no better person to step into the role.”

It’s no secret she’ll have to tackle issues her predecessors didn’t. It’s also no secret the Big South is a low- to mid-major conference that could, in theory, be particularly vulnerable to the changing winds of college sports.

That includes conference realignment. That includes sustaining football. That includes staying competitive in basketball — the conference’s sport of revenue and relevance — just as the transfer portal has made it more difficult than ever for mid-major teams to retain their top talent.

If you ask Montgomery about these issues, she’ll offer a by-the-book response. (“Essentially, in its purest form, it’s a positive,” she’ll say of the name/image/likeness mess, for example. “But what we’re grappling with now is, ‘How do we define market value?”)

In many ways, she’s ideal for the changing college sports world — a younger, former athlete with familiarity and loyalty to the conference she now runs.

“I’m confident,” Kallander said, referring to his successor, “that the Big South is in better hands now.”