Neil Patel

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Carolyn Childers’ startup venture, Chief, is on a mission to drive more women into positions of power and keep them there. She’s already found backing of over $140M to make that happen. 

On the Dealmakers Podcast, Childers shares how her career evolved from investment banking to corporate to startups. Plus, how she’s built a national network for senior executive women , and navigated through a Series B funding round.

Listen to the full podcast episode and review the transcript here.

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Building Entrepreneurial Skills Early

Carolyn Childers was born in upstate NY. She grew up in a tiny town, without any traffic lights. 

She still has fond memories of that environment. Growing up in a supportive community, where you could go hiking every day, and education was highly valued. 

Childers was also the youngest of three siblings. Together these experiences instilled some early lessons and skills that would prove useful in the startup world. 

She became very competitive in sports, which also taught her about team building and putting in the hard work. 

Basketball took her around the country to compete in the junior nationals, which opened her eyes to everything else that was out there. 

After studying finance in college, Carolyn found herself in investment banking. She saw this phase of her career as being a great way to learn from leaders and better understand how they think. 

Three years in, she made the switch to corporate. First working with Avon, and then Victoria’s Secret in business development and strategy. 

Still having that competitive nature, Carolyn says she was far more interested in pushing things forward and taking big swings, rather than being lost in fine tuning the details, which made corporate not such a great long term fit. 

It was then that she headed back to school, and attended HBS. Though her goal this time around wasn’t to necessarily learn the material but to build out her network. Having been more of an introvert up to this point, and being very focused on her work, she says she had never made going out and meeting people a priority. This environment proved to be the forcing function that changed that.

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Discovering Startups

The network that Childers built by going back to school ended up turning into a job opportunity. One she didn’t feel qualified for, but business still remains largely about who you know, and who knows you. 

The company wanted her to launch and run a new vertical, She helped grow it to a $100M business before it was acquired by Amazon.  

Carolyn says that she was inspired by this experience, and the ability to really focus and work on the things that made a difference. 

However, before jumping in to launch her own venture, she spent the next five years working inside other startups. This provided a much more well rounded perspective of what it really means to be a startup. Including all of the good, bad, and the ugly. 

Some of her biggest takeaways from this period were around building company culture, and giving team members the autonomy to do their best work, and unlocking their potential. 

She was able to witness this across a variety of industries and types of businesses. From ecommerce to marketplaces. 

The Reality Of Early Stage Startups

Even with all of that experience, Carolyn says that the early days of starting her own venture were some of the hardest and darkest of her entire career. 

Along with her cofounder Lindsay Kaplan, she set out to launch her first startup of her own. Immediately, she says that there is a lot of pressure and self-inflicted fear. Knowing that everything, good and bad, will be attributed to you.

It is an issue which can be compounded as you run into more challenges on the journey. That came early for this entrepreneurial duo. They couldn’t even find a lawyer to help them incorporate and represent them for  fundraising. 

Then, even after that, their network really didn’t show up for them when it came to trying to raise their Seed round. They knew people. They knew investors. Yet, they faced a lot of noes. 

Fortunately, Carolyn says that they were so busy with different meetings they didn’t have time to go back to the drawing board with all the feedback and change the basis of their business. 

Of course, by their Series A round, a lot of those initial investors who said no, now wanted to get in. 

Alphabet’s CapitalG led their $100M Series B round. 

Today, some of her top advice to others is to maintain some balance during those times. Rather than allowing your whole identity to be intertwined with your startup and every bump and challenge, she recommends maintaining connections outside of your work world. If you do that, she believes the journey will be happier, and you and your team will be healthier. 

Storytelling is everything which is something that Carolyn Childers was able to master. Being able to capture the essence of what you are doing in 15 to 20 slides is the key. For a winning deck, take a look at the pitch deck template created by Silicon Valley legend, Peter Thiel (see it here) where the most critical slides are highlighted.

Remember to unlock the pitch deck template that is being used by founders around the world to raise millions below.


Carolyn Childers’ startup Chief is the private network designed for the most powerful women executives to strengthen their leadership, magnify their influence, and pave the way to bring others with them.

Chief membership is designed for women in the C-Suite, senior executives, and accomplished VPs who are changing businesses and industries. Executives are evaluated for membership based on seniority, professional experience, background, and impact, as well as a demonstrated history of supporting others along the way.

The Chief network is designed specifically for women executives who believe that power grows when it’s shared. By bringing together the most accomplished business leaders across the country, Chief fosters meaningful connections and shares more of the knowledge that collectively grows women’s power. Chief members gain access to: a powerful network of peers, curated peer groups, workshops, legendary conversations with influential business leaders, and community groups.

Chief has been recognized as one of Fast Company’s Most Innovative Companies of 2021, and its diverse membership includes more than 15,000 of the most senior business leaders in the United States, with a wait list of 60,000 more.

With a goal of changing the face of leadership, Chief is building a network of executives spanning companies, industries, and backgrounds whose collective power drives change from the top down.

Listen in to the full podcast episode to find out more, including:

  • Chief’s vision for the future
  • How leadership and corporations are changing


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