Leadership Reimagined with Robin

From spaces to banking to even eyewear, offline businesses are rapidly being reinvented. As an investor, I’m curious about how people are changing the industries they work in. Reimagined with Robin is a show where I conduct live 15-minute interviews with founders and change-drivers who are reimagining all aspects of life.

Throughout the whole of Women’s History Month, I’ve been thinking about Chief and how they have been reimagining leadership, especially for women. Chief is a private membership network focused on connecting and supporting women executive leaders. I’ve had the privilege of serving as a founding member and investor of Chief, and I’ve always been inspired by the way Chief has built a support system for women in leadership positions. This is especially prevalent through my core group, which is a community of peers that Chief has curated with me, facilitated by an executive coach. In order to truly understand the value that Chief brings, I broke this series up into three parts by founder, coach, and member: first, I interviewed Carolyn Childers , the co-founder and CEO of Chief; second, I spoke with Lisa Rubin , who is the core guide for my core group; finally, I chatted with Megan Cunningham , a fellow founding member, to find out how she benefits from organizations like Chief.?

?Click here to watch Carolyn, here for Lisa, and here for Megan. Here’s a recap:

PART 1: CAROLYN CHILDERS, CEO OF CHIEF

What are you reimagining?

• At the senior executive level, you are often expected to have all the answers. In reality, you don’t always have all of those answers, and even if you do, you need a support system around you to help you to push forward, make the right decisions, or talk about things that are affecting you at the workplace or at home. Chief is creating a membership for women that goes beyond professional networking by building a deeper community where true support can come through.

Why is this happening now?

• A lot has happened over the past few years that have brought on struggles and hard times, but on the flip side, leaders and companies are truly starting to understand how important representation is, as well as investing in their people. Companies are having to throw out their playbooks and reimagine what investment in their teams looks like.

How will our world be changed by Chief in the next 5-10 years?

• Today, Chief has about 10,000 members across the US. “I am so inspired about the idea of what this community can do together, and the change that it can drive more broadly when Chief is across every city in the nation… I think that there is truly that ripple effect that we have been wanting to create from day one,” says Carolyn. Chief continues to invest in their members’ individual experiences.

How are you reimagining yourself as a leader this year? What made you want to jump to the CEO role?

• Carolyn has been a senior executive at many startups, as well as part of many growth journeys at various companies, but before Chief, she had never been in the seat of the entrepreneur. At the end of the day, Carolyn has found in Chief an idea that she was ready to live and breathe day in and day out, and she is excited to continue to work on the Chief mission.

PART 2: LISA RUBIN, CORE GUIDE AT CHIEF

What attracted you to Chief?

• What drove Lisa to Chief was the mission to drive more women to positions of power and to help them stay there. Lisa spent a lot of time in the corporate world being the only woman in the room, and she did not always have a peer network or mentors. Chief is truly a place where women can exchange different viewpoints and bolster each other.

?You help facilitate a core group at Chief. Can you explain them more in depth? How are these peer groups vital to Chief?

• Core groups at Chief are formed to accelerate individual and group growth. When someone becomes a member of Chief, they are curated into a group of around 8-12 women that are in similar life stages and have similar scopes of responsibility, but are otherwise very diverse – they can be from different industries or different functions within industries. Each core group also has a guide, which is what Lisa does. Each group is unique, but ultimately the group does not exist to teach or coach; rather, each member comes together to guide each other through their leadership journeys. Members can talk to each other about professional and personal goals, but it’s up to the guide to establish a safe space and listen for universal themes. Core group is like a “peer advisory brain trust” that helps to add to members’ thinking and perspectives.

How are you reimagining the way you coach with Chief?

• In Lisa’s work as a private executive coach, she approaches every engagement with a specific goal in mind and thinks through methods for measuring success. With Chief, Lisa instead takes a more holistic view, recognizing that authenticity is vital to leadership. Lisa encourages her core group members to bring their whole selves to the group, to cross the realm between the professional and personal. Chief also provides guides with exceptional training in the diversity, equity and inclusion (DEI) space, which Lisa believes has helped her become a better coach.

?How are you reimagining yourself as a leader this year?

• With geopolitical climate and the loss from Covid, it can sometimes be difficult to stay positive. Lisa has made it a goal for herself to reconnect with her natural optimism. She believes that leaders have to be able to see the challenges in front of them realistically, but also knows that being able to see possibilities is what drives change. What will the future look like when there are more women in power and more women in leadership?

PART 3: MEGAN CUNNINGHAM, FOUNDING MEMBER AT CHIEF

What does it mean for you personally to be one of the founding members of Chief?

• New York was the first city that Chief launched in, and Megan was one of the first members of Chief in New York, meaning she was one of the first founding members of the organization at large. In the beginning, Megan was pensive about joining Chief as early as she did, because she already had a strong support system from her family and her mentors, many of whom were women. However, there was not a lot of opportunity to connect with these women beyond private conversations. But when Megan, who works in the film and media industry, joined Chief, she was able to connect with executive women within her own industry as well as other industries. The opportunity to have conversations with a large community of women who held diverse roles across functional leadership positions was a huge benefit.

How is Chief different from other networks and memberships?

• It comes down to three things: one, Chief is a truly inclusive and diverse organization that has prioritized embracing women from all walks of life. Second, Chief’s programming is second to none, providing their members with opportunities to connect intimately to incredible leaders like Michelle Obama, Gloria Steinem and Amal Clooney. The third is core group, which provides the support and strength for its members to tackle anything.

?What do you hope women will take away from Chief?

• Especially for women who have accomplished a lot and have achieved a lot in their careers, Chief gives its members an inspiring, playful quilt of different experiences and objectives, goals, and ways of making one’s life even richer.

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