Be HER(d): Life and Career Advice from a Female Board Member and Former CFO

Be HER(d), hosted on LinkedIn Live by Vaco, Focus Search Partners’ parent company, is a discussion series highlighting inspirational women in leadership roles. A recent episode featured Cynthia Jamison, a current board member at Tractor Supply, Office Depot, Darden Restaurants, and BigLots, as well as a former CFO. Together with moderator Monica Foster, managing director at Focus Search Partners, Jamison offered vulnerable observations and candid experiences she’s had throughout her career, including workplace mentorship for women, failure within the C-suite, and leaning into your authentic self. 

When Monica Foster met Cindie Jamison over a decade ago, she didn’t realize at the time that Jamison would become a trusted mentor and friend. Foster recalls their first meeting fondly: She had just moved to Chicago and taken a position at a firm where Jamison held a senior leadership role. One night, at a social dinner for their company, Jamison was the keynote speaker—and Foster vividly remembers how she captivated every member of the audience that evening. Not all CFOs have that ability, but right then, Foster knew Jamison was special and should pay attention to her career.

Jamison’s ability to captivate and inform an audience didn’t happen by accident; she had thrived in the role of crisis CFO for numerous companies throughout her career: She led finance teams to success after the passage of Sarbanes-Oxley and again when the Great Recession brought a reckoning for companies across industries. Given her storytelling skills and ability to influence, Jamison made a significant impact as a leader during these challenging times in business.

After years serving as a chief financial officer—in both interim and long-term positions—Jamison transitioned from the C-suite to the boardroom; she now serves on the boards of four publicly traded companies. Despite her success, her career trajectory wasn’t straightforward or without setbacks; she entered the corporate world at a time when there were few examples of female leadership and virtually zero women mentors.

During the Be HER(d) broadcast, Foster and Jamison discussed the latter’s journey from CPA to CFO to formidable board member—and Jamison spoke candidly about her (sometimes rocky) journey to the C-suite and eventually board leadership.

The power of going with the flow

Early in her conversation with Foster, Jamison emphasized her unconventional path to the top of the corporate ranks. She had been raised in a family of physicians and medical professionals, and had very little exposure to the worlds of business and finance growing up. In college, she considered pursuing law at one point, but she decided to attend business school instead. She was far more interested in the finance side of things.

“So I started pivoting—to use today’s term—towards that [the financial side of business]. But it was definitely an evolution, and I absolutely never even thought about being a CFO,” Jamison said. “I’m not even sure I knew what a CFO was when I was younger.”

Even though she knew what she was interested in, Jamison never had a plan for the path her career would take. In fact, she says she’s never been fixated on planning her professional journey; doing so can quickly turn into what she calls “an exercise in futility.”

“Careers are 30, 40 years long,” she noted.

“And life will throw a lot at you. You never know when you’re starting where you’re going to end up. So I would say go along for the ride, and don’t feel too hemmed in by plans.”

Success and resilience go hand-in-hand

When asked about how she reached the C-suite without having a plan to get there, Jamison was candid.

“I think anyone who has reached a level that people view as successful would have to say there’s a level of luck involved, there’s a level of timing involved, there’s a lot of hard work, and there’s a lot of breaks, good and bad that you have to navigate,” Jamison said.

At the end of the day, she believes that resilience is really the key ingredient in her own recipe for success.

“I think resilience is probably the single most important skill set or muscle that you can develop as you’re coming up through the corporate ranks,” Jamison said. “Every single person will have times in their career where they’re going to have to dig deep…come up with a Plan B, think differently about something, extricate yourself from an environment, or deal with being extricated from an environment against your will.”

For her, Jamison said the key was combining resilience with openness, being willing to go with the flow but never losing herself along the way. It’s in going with the flow that young professionals can figure out who they are, what they’re good at, and what they’re not so great at.

Also important? Not hyperfocusing on turning weaknesses into strengths.

“I don’t think successful people [are successful] because they turn weaknesses into strengths. I think they learn to deal with their weaknesses, and they play to their strengths,” Jamison added.

The changing experiences of women in leadership

When the conversation turned to her earliest experiences as a woman in the corporate world and in leadership roles, Jamison was again frank about her perspective.

“I certainly know a lot of really supportive women now, and I really appreciate that. But when I was young, when I needed mentoring the most, I really didn’t have anyone. I had a lot of bosses who lived very different lives than me. They weren’t trying to balance kids. They typically had stay-at-home wives. They just didn’t have the kinds of day-to-day pressures that I had,” Jamison said.

“For that reason, I’m not sure [my early bosses] could have been much help to me, even the good ones, so I missed out on [mentoring] and I think I was worse for it,” she observed.

Those early career experiences have molded Jamison’s own perspective on the importance of mentors and inspired her to pursue mentorship and coaching of young professionals in her own orbit. Leadership skills, especially, can be elusive; employees often receive extensive technical coaching and training, but management skills—which are far more intuitive—are harder to cultivate and nearly impossible to quantify.

Simply having a space to be open and vulnerable, to ask honest questions, can be invaluable for young leaders. This is especially true for women leaders, who are often facing circumstances and challenges that are very different from their male peers.

The secret to an effective mentorship format

Speaking from her own experiences, Jamison feels that informal mentorship is more effective than a formal, structured program.

“I think mentoring is so much about chemistry. If the chemistry isn’t there, it’s not going to work. When a younger professional reaches out to say, ‘Could you spend some time with me?’, it’s wonderful…because then you know they’re interested in what you have to say. You aren’t shoving it down their throat,” Jamison said.

Towards the end of their conversation, Foster asked her mentor and former colleague for her top advice for young professionals.

Jamison was happy to divulge.

“The best piece of advice I ever got, which I’ve passed on many times, is this: you’re never as bad as you think you are, and you’re never as good as you think you are,” Jamison shared.

“[That perspective] helps you moderate the highs and the lows. So, when you’re feeling down, it’s helpful to just think, ’It’s not this bad. Other people have been through this.’ And when you’re feeling great, it’s somewhat humbling to think, ’Okay, you’re not that great. Bad things can still happen. Be careful.’”

Watch the full episode of Be HER(d) to get additional insights and career advice from Cynthia Jamison:

About our guest: Cynthia Jamison

Cynthia Jamison serves on the Board of Directors of Tractor Supply Company (NASDAQ:TSCO), a position she has held since 2002, where she is Chairman of the Board, after serving as lead director, and chair of the audit, compensation & corporate governance committees. She also serves on the Office Depot Board (NASDAQ: ODP), Darden Restaurants Board (NYSE: DRI), and BigLots, Inc (NYSE: BIG) Board. Her previous board roles include Horizon Organic Holdings, Cellu Tissue, Caribe Media and B&G Foods.

Prior to her full-time board service, Cynthia had an executive career as a CFO, COO, managing partner for such companies as Tatum, LLP; eMac, Inc, a joint venture between McDonald’s Corporation and KKR & Co. L.P; Cosi, Inc. (NASDAQ:COSI); SurePayroll, a payroll processing firm; and Illinois Superconductor, a radio frequency cellular technology company. Prior to her CFO roles, she held executive positions of increasing responsibility at Arthur Andersen, Kraft General Foods, Hewitt Associates, Allied Domecq (Dunkin’ Donuts/Baskin Robbins) and Chart House Enterprises.

She is a frequent keynote speaker on CFO and boardroom topics, and quoted as a financial/economic expert in Forbes, the Wall Street Journal, Newsweek, CFO Magazine, Agenda, Board Member and the Economist. She is also an NACD Board Leadership Fellow and was awarded the “Top 100 Director” honor in 2017.

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