Spotlight on Women Leaders: Kendall Cherry, the Founder and Chief Storyteller at The Candid Collective
Spotlight on Women Leaders Series
👉Celebrating women leaders across industries and advancing the conversation on leadership—reflecting CFW Careers’ expertise in retained executive search, global executive search, and professional coaching.
Welcome to our Spotlight on Women Leaders series, part of our Changing the Conversation initiative. This series reflects our founding commitment to advancing women in leadership by moving beyond identifying barriers to focusing on solutions, supporting women in their careers, while also influencing organizational practices and policymaking.
At CFW Careers, we combine the reach of global executive search with the insight of professional coaching, serving leaders and organizations. Since 1973, we’ve been committed to opening doors, creating opportunities, and helping anyone on the rise in their career not just succeed but thrive.
Kendall Cherry
Today we’re speaking with Kendall Cherry, the Founder and Chief Storyteller at The Candid Collective. Kendall, can you start by introducing yourself and describing your work at The Candid Collective?
I started my career as a copywriter and ghostwriter for 7-figure brands. I've written for content powerhouses like Codie Sanchez at Contrarian Thinking, Vanessa Dew who co-founded Health-Ade Kombucha, and AppSumo just to name a few. I've also developed an educational curriculum around storytelling and sales skills that serves both small business owners and copywriters who are ready to emerge into a premium market.
Storytelling is at the heart of sales and leadership. From your perspective as a professional ghostwriter, what makes a story compelling enough to capture attention and drive action?
I think the thing that most people forget about storytelling is that it's meant to be used as a tool to create a call to action. It's not just something that you say or share to get more likes, views, or engagement. It's all about connecting and then converting people into your way of thinking, paying you, or completing any other action you want them to take.
Many professionals, especially women, struggle with advocating for themselves, whether it’s negotiating pay, pitching their services, or sharing accomplishments. What strategies do you recommend for communicating your value with confidence?
I think a lot of people, women especially, feel really uncomfortable or like they're bragging if you share about your accomplishments or results. If you're someone who falls into this category, I find it's easier to tell the stories of your clients and customers (the people you serve), instead of focusing on your own story or personal philosophies.
Most customers want to see social proof of what it was like to work with you and how you created a specific transformation, and actually care less about your personal stories if they don't relate back to your business or how you serve your people.
You work behind the scenes helping leaders tell their stories. What have you learned about the link between authentic storytelling and building trust in business relationships?
I think there's been a lot of people who have used stories to falsify their narrative, bamboozle people into paying big money for lackluster offers, and everything in between. We're currently in a trust recession, and I find that authenticity is the thing that people can smell from a mile away.
The more honest and authentic you are in your content, even if it's hard or dissuades some people from wanting to work with you, you'll end up attracting more of the perfect-fit clients and customers that you are meant to be serving.
For people in sales or client-facing roles, what advice would you give on balancing persuasion with authenticity, especially in high-stakes conversations?
I think it's important to remember that the opportunities that are meant for you aren't going to go away. There's nothing you could possibly do to steer them away from you, even if it is a high-stakes situation.
In fact, I find that the more pressure you put onto conversations like these, the more likely you are to fumble the sales conversation or come on too strong and cause people to feel like you're too intense instead of easy to work with.
How can people connect with you and learn more about your work?
I'm very active on LinkedIn and love getting connection requests from people who encounter my work. I also write a weekly newsletter called Wallflower Fridays, which you can sign up for at wallflowerfridays.com.
And if you're a writer or small business owner who happens to write your own content, I have a podcast called The Writer’s Round that you can listen to wherever you get your podcasts.
Through our work in retained executive search and leadership development, at CFW Careers, we’ve seen the powerful impact of amplifying women’s voices in business. This series celebrates women leaders across industries, sharing their perspectives and paving the way for the next generation.