306 - Selling Into the C Suite with Cherilynn Castleman

Cherilynn Castleman has over 30 years experience as a Fortune 500 Global Sales Executive, and her mission is to see a million women of color sit at the table of their dreams by 2030. That table means the C Suite, Sales Leadership, the Sales Leader-board or the Entrepreneurs’ table. She’s helping to overcome the problems these women often face of access and financial fluency to get there. Today we’re going to dive into her mission and how you can help support her, as well as just one of the many areas of her subject matter expertise, which is how to have the confidence to sell into the C Suite and how to carry those conversations powerfully and with authority. Show Notes: [2:29] - Cherilynn has been in sales since before Girl Scout cookies were 50 cents a box. She shares her backstory and her love for talking to people. [3:51] - Out of 1800 CEOs of Fortune 500 companies, there was only one woman of color in the role. [6:18] - What is it like to be the only one in the room that is like you? Cherilynn shares some of her experiences on her journey. [8:16] - Be an upstander, not a bystander. [9:34] - You have to connect with your clients by immersing yourself in their world. [11:02] - Learn how to read annual reports. [11:53] - Ask the four F’s: first, finest, failure, future. These are the questions you can ask in a valuable client call. [14:36] - It’s amazing what results you can create when you ask these questions. [16:27] - Post things from your point of view. Pick topics that you post on regularly so you are seen as an expert. [18:43] - Cherilynn explains an activity called The Hundred List. [20:24] - If we believe the negative thoughts we have about ourselves and progress, they start to run the show. [22:07] - It’s important to share about your superpowers. But how can you do that without it sounding like you’re bragging? [24:49] - Write to your audience and to make it even better, think of a specific person or type of person and write it almost directly to them. [26:00] - Shout out to other people and let them know you see them. [27:40] - With a mission and a vision as large as Cherilynn, how does she overcome imposter syndrome and the overwhelming self doubt? [29:59] - Give your limiting belief a name. Check in on them. [32:05] - Think about your limiting belief and inner voice as a friend. [33:21] - To create a new habit, anchor it to an old one. Connect with Cherilynn: Cherilynn Castleman Home Page Twitter | LinkedIn Links and Resources: Instagram | LinkedIn | YouTube She Sells with Elyse Archer Home Page Abundance Mini Course Join the $10K Club Apply for the $50K Club Mastermind