Women at the Top: “The Rise and Reverence’ Virtual Panel Event

Headshots from women on top article

Three trailblazing women. Three distinct journeys to success. One hour of insights and wisdom.

Caprock recently welcomed a panel of remarkable female leaders to share their experiences and insights related to their leadership journeys. Errin Green of RER Solutions, Jessica Rolph of Lovevery, and Elizabeth Littlefield of West Africa Blue engaged in a refreshingly candid conversation about their approach, lessons learned, and their advice for maintaining motivation along your own path to success.

During this discussion, the panelists share how they:

  • Discovered the importance of authenticity
  • Developed communities that helped them evolve and stay innovative
  • Overcame self-doubt and began trusting their instincts
  • Learned to say “no” and prioritized what matters most to them
  • Built effective and efficient teams and partnerships

Insights From ‘Women at the Top: The Rise and Reverence’

The three leaders who joined Caprock’s recent virtual panel event rose to success in different industries, yet their career paths share many of the same hallmarks: Passion, perseverance, and dedication to fulfilling the promise of their missions.

As prominent female leaders, Errin Green, CEO of RER Solutions, Inc.; Jessica Rolph, CEO of Lovevery; and Elizabeth Littlefield, Senior Partner at West Africa Blue, have forged their own ways forward. During this dynamic conversation, they shared the lessons they gleaned and the challenges they overcame to build their successful organizations and hone their leadership abilities.

Stay True to Your Vision

All three leaders stressed the transformative power of aligning their actions with their visions. Rolph wanted to create a program around early learning and founded Lovevery to manufacture playthings and tools. From the start, her collaborative approach has led to further innovation.

“I love co-creating with our customers,” she said.

A customer approached Lovevery and said she didn’t see her child, who has a limb difference, represented in the company’s books for children. “She was like, ‘I’d love to do a book with you.’ And so we flew down to Arizona and we created this darling book, ‘Alora Makes a New Friend.’ ”

For Littlefield, staying true to her vision meant carving a new path in the financial industry. “My journey started when I left college and I was absolutely terrified of becoming a banker,” she said. “But that seemed like a good path for someone that didn’t know what to do at the time.”

Volunteering with Meals on Wheels in Harlem opened Littlefield’s eyes to the possibilities of helping the economically disadvantaged. She became a leader in microfinance and found ways to reconnect with the need behind her mission, including taking a two-year leave of absence from JP Morgan to build microfinance institutions in West Africa.

Green’s career path was formed by her early career years in Washington, D.C.

“I was really struck by how many successful female and minority entrepreneurs there seemed to be in the D.C. area versus where I previously lived in Boston,” she said. “I eventually came to realize that a lot of them were involved in the federal contracting space.”

She took a job at RER Solutions, the company she now runs, and stayed true to her belief that the federal contracting industry could unlock potential for people of all backgrounds.

“We’re federal contractors,” she said. “I don’t do any commercial work. I don’t do any state or local work. I continue to believe that contracting offers significant opportunities for women and minorities who have an interest in being a business owner.”

Build Networks For Each Stage Of Your Growth

Rolph has found support through community over the course of her career, from start-up entrepreneur to CEO of a multi-million-dollar company.

“There are people and communities and insight and inspiration that you can find throughout your evolution as a person,” she said.

As a Henry Crown Fellow at the Aspen Institute, a non-profit devoted to creating a “free, just, and equitable society,” Rolph found encouragement as she navigated the sale of her first company. Her current membership in the Young Presidents’ Organization has provided insights as she considers taking Lovevery public.

In addition, she relies on a number of informal communities. The common thread is her desire to be strategic and authentic in her networking. “How can I be really real about the insecurities, the personal impacts to marriage and to children and to family — to all the things — and still be a whole person in that community,” she said. “I think (networking) can really help you achieve your dreams and have a meaningful career in life.”

Challenge the Expectations of Others — And of Yourself

Littlefield began her career on the trading floor in an era when women were an anomaly in the financial markets.

“I would say during the early years there weren’t any role models, really,” she said. “I mean, the word ‘political correctness’ was not even a concept, much less of a term.”

At one time, she was the only female trader on a trading floor of 700 people. As Littlefield became more established in her career, she was surprised by colleagues’ reactions to her ability to be both warm, inclusive, and exacting.

“I feel like men get away with being warm and friendly, but then also tough,” she said.

Green, on the other hand, went on a journey of personal discovery to develop her authentic leadership style.

“I think that early on I lacked some of the confidence in my leadership abilities,” she said. “And I think the consequence of that was that rather than asserting myself, in instances where it probably would have been appropriate to do so because the direction I was attempting to lead the company was the right direction, I deferred some difficult decisions.”

After allowing others to influence her, she gradually began following her own lead. “As some of the decisions I made kind of proved out, I gained the confidence to step into my leadership style and be more assertive in those cases where I needed to be,” she said.

Be Wise With Your Time

Each of the leaders on Caprock’s panel stressed the importance of strategically using time. Green discussed how she has found purpose and meaning in community service activities, but the way she approaches those commitments has changed. In the past, she served on boards that required long tenures. Now, she finds other avenues to participation.

“Each year, I try to find a couple of organizations that offer some sort of meaningful mission, and provide either support through time or charitable contributions,” she said.

Littlefield shared her struggle to find balance between work and other commitments. Currently, she serves on seven boards. “One thing I wish I had done better recently is learn to say ‘no,’ and really have a clear litmus test about things that people ask you to do.”

Rolph prioritizes her roles as CEO, wife, and mother. “Even though I’m saying no to a lot of outside work, I’m still feeling very stretched and finding, you know, meaning and moments of purpose,” she said. “And all of that can be hard. Some days, I feel like I’m just on a race to just wake up, get the kids, try to be present with the kids, try and do everything I can to squeeze out the most meaning of my work day.”

Surround Yourself With a Diverse Group of Colleagues

Each leader on Caprock’s panel stressed the importance of collaborating with people who complement their strengths — or bring attributes they lack.

“It sounds obvious, but make sure that you’re recruiting people who don’t think like you,” Littlefield said. “That may make you a little bit uncomfortable. Because I do believe in having that yin and yang. And I know I’ve really, really benefitted from having somebody who’s quite different from me as a partner.”

Green acquired her business rather than building it from the ground up; her focus has been on recruiting colleagues who could help develop the business. “In this space, there are a lot of people who can promise to bring work, but most of them are not very effective at doing it,” she said. “So figuring out how to kind of weed through the promises to (get to) people who can actually be effective has been a challenge.”

Instead, she has focused on working with people who excel at managing contracts and evolving their roles into business development.

Listen To Your Instincts

Every leader on the panel expressed the importance of pausing and tuning into their own guidance. For Green, self-trust emerged gradually as she gained experience. Littlefield used the enforced pause of the pandemic to re-evaluate whether she really desired a CEO job — or whether she was allowing her ego to make an important decision for her. One of Rolph’s major turning points came when she ignored the advice of a more experienced colleague and stuck with her business plan.

Yet, Green said, even when following your instincts it’s important to develop a sense of resilience and perseverance. “One of the things that I’ve learned is: Being a leader is hard and when running a business you’ll experience a ton of failure,” she said. “I was not comfortable with failure early on. Learning to bounce back from that failure and continuing to move forward has been kind of critical for my learning and growing as a leader.”

Rolph agreed. “You can turn (your business) into something even more meaningful for yourself if you get rejected or if you don’t make it,” she said.

Caprock often hosts discussions and events with our own experts and notable business leaders. To learn about upcoming opportunities, sign up for our newsletter.


May 5, 2023


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