Ep. 111 – Building AI Fluency, Trust, and Modern Sales Leadership with Cherilynn Castleman - Part 2
Ep. 111 – Building AI Fluency, Trust, and Modern Sales Leadership with Cherilynn Castleman - Part 2  
Podcast: Selling the Cloud
Published On: Tue Jan 27 2026
Description: In Part 2 of this Selling the Cloud conversation, Cherilynn Castleman joins Mark and KK Anderson to unpack what strong CRO leadership looks like in a time of rapid AI adoption and constant go-to-market change. As every team claims to be AI-first and tech stacks continue to converge, Cherilynn explains what truly differentiates leaders who drive real results.This episode dives into how curiosity with AI, disciplined daily usage, and protecting selling time translate into cleaner pipelines, shorter sales cycles, and fewer end-of-quarter surprises. Cherilynn also shares practical guidance on modern operating rhythms, how to run meetings that actually matter, and which metrics prove that change is working now, not quarters from now.What You’ll Learn:Building AI Fluency as a Leader: Why modeling curiosity, transparency, and experimentation matters more than mastering toolsAI as a Daily Discipline: How consistent usage creates confidence, clarity, and better decision-makingProtecting Selling Time: How CROs can reduce meetings and increase seller productivity from 10 hours to 15 to 20 hours per weekHumanized Outbound at Scale: Using AI for micro-segmentation while keeping messaging personal and relevantRunning Meetings That Matter: How 30-minute meetings, no slides, and clear ownership tighten pipeline executionProving Change with Metrics: The three numbers boards and CFOs care about to fund and support transformationKey Topics:CRO leadership in an AI-saturated GTM landscapeModeling AI curiosity and transparency across revenue teamsStop chasing tools and start building the right mindsetExact meetings, executive engagement, and decision-maker accessMicro-segmentation by persona, industry, region, and generationModern revenue operating rhythms and pipeline hygieneMeasuring cycle time, executive involvement, and multi-threaded win ratesGuest Spotlight: Cherilynn CastlemanCherilynn Castleman is a sales and leadership advisor who helps revenue teams adapt to modern buying behavior and post-pandemic selling realities. She is the author of Post-Pandemic Selling, a top Amazon bestseller that has been recognized by Salesforce as one of the top sales books for modern leaders. Cherilynn is also an active LinkedIn voice, hosting frequent LinkedIn Lives where she shares practical insights on sales leadership, AI fluency, and authentic connection.Resources & Mentions:Book: Post-Pandemic Selling by Cherilynn CastlemanWebsite: postpandemicselling.comRecommended Book: The Untethered Soul by Michael A. SingerLeadership Voice to Follow: Bill Green, former CEO of Accenture🎧 Listen now and follow Selling the Cloud for more insights on AI-driven leadership, modern sales execution, and building trust across today’s go-to-market teams.Mark (00:30)All right. Let's move to topic three. Leading as a CRO in a time of intensechange. So every team nowadays says they are AI enabled, they're AI first, and everyone's sales and marketing stack just looks very similar. So from the seat of the CRO, what actually differentiates leadership right now in your opinion? Could you give us two or three weekly behaviors you expect to seein the numbers of a CRO that is leading well.Cherilynn Castleman (01:04)Yeah, so a couple things. I think that if a CRO is demonstrating curiosity with AI, they are using AI, they are sharing with their team, this is what I did. I was working with the CFO for a huge company recently and they do a pricing exercise. And they normally would sit down for a couple weeks and work on this pricing exercise. And I challenged them to open AI and pull their data into their proprietary system.And in 30 minutes, they had done the entire exercise. And so it was like, wow, everybody's going to be impressed. I said, no, it's transparency. Tell them you used AI to do it. Demonstrate, model that you're curious. If you fail, talk about that. So number one, they're modeling curiosity. Two, it's a discipline. They're using it on a daily basis. They're talking about it on a daily basis.There are somewhere between 50 and 200 new AI tools every day. There are, when you look at go-to-market tools, there are somewhere between seven and 10 new tools every day. There's no way you can master the tools. Stop chasing the tools. It's a mindset. It's about confidence and clarity. The next thing that I would say is that ⁓ protect the selling time.Look at your meetings and make them very efficient. Get them down to 30 minutes. The goals is most sellers sell about 10 hours a week. You want to get your sellers to 15 to 20 hours a week. And so where you're going to see this, are you going to see a cleaner pipeline, you're going to see higher exact meetings. And so those are things you want to measure is not just meetings, but exact meetings, decision-maker meters. It will shorten the sales cycles and you'll have fewer surprises at the end of the quarter.KK Anderson (02:43)So good. was just on a coaching call just before this podcast episode actually, and was coaching a new seller that was joining the team and was asking about the hustle and the grind and around hunting. And so we popped open Chachi BT and we put in the overall team's average deal size, average win rates, know, sales cycles. And he...figured out that he needs to make 6,700 calls in the first six months to be able to get the number of opportunities in his pipeline to be successful. And he was like, what? 6,700 calls. But you break it down into a daily rhythm. And you break it down into who you're targeting. And you can use AI for those things to get smarter and hone in on offers based on personas and POVs. It's interesting.Cherilynn Castleman (03:24)Absolutely.It is. And the other thing is thatthe goal, and so I think Mark mentioned this, we're opening emails and we're like, yep, AI wrote that, yep, AI made it. And so what I challenge people to do is, yes, you have to do your volume, but what if you spent 15 to 30 minutes every day sending a couple better emails? Where you actually, you know, and so, then, yes, if you sent a humanized email, I love it when every once in a while I get an email and I'm like, yes.KK Anderson (03:50)humanCherilynn Castleman (03:56)this lands. We all know what those feel like. We'll learn to send those kind of emails. And if you're not sure, I tell people, email them to yourself and then open it on your phone. If you won't open it on your phone with the subject line and the first sentence, why would anybody else? So send it to yourself, look at it, and yes, get your numbers in, but spend time figuring out how to craft.better emails and micro segment because once you've done your micro segmenting, you can do emails to Gen Z, Gen Y, Gen Alpha. You can do it by title, can do it by industry, West Coast, East Coast. AI will do all that. Do all your micro segmenting and then you're now doing a more humanized outbound and I promise you, you'll hit your numbers and make fewer and send less noise.KK Anderson (04:43)meaningful, more meaningfuloutreach, yeah. Okay, so you said something a second ago. You said when Mark was asking about the CRO and leading well, you said less meetings and the meetings that are, having the meetings that are meaningful. And nobody likes a meeting, everybody hates a pipeline call, we know that, right? So like what in today's day and age, like what is like,Cherilynn Castleman (04:46)Yeah.KK Anderson (05:05)What are the non-negotiables, but what gets cut and what changes and what, talk to me about that operating rhythm, is it changing?Cherilynn Castleman (05:11)So I think it is. I think that, so what I encourage people to do is do 30 minute meetings because of AI and technology and Facebook and Instagram and everything. The 10-minute spans are very short. So do a rapid 30 minute meeting. Revenue review, focus on what are blockers, what is getting in the way. Focus on owners, deadlines, next steps. No slides, no noise, no operational.I used to call them my quick stand up. I taught my team the rule of three. They had to come in and in one minute or less give me three things about this deal that I needed to know and then end with, so it's a bottom line up front. Bluff is a military phrase, bottom line up front. Three things, one, two, three, and then conclude with here's what I know, here's what the so what is, or here's a call to action. People come in without slides.and give you those updates, you're gonna see your pipeline tighten up. And you're not gonna have surprises, you're gonna have that transparency. And then every meeting must either build a skill or make a decision. How many times you sit in meetings and it's just updates and it's updates and there's nothing. Either we're going in to make a decision or we're gonna build a skill. And like I said, I would do a 30 minute meeting, that, teach me something in five minutes at the end.KK Anderson (06:18)Excuse. Excuse. Excuse. Yeah.Cherilynn Castleman (06:27)So everybody is learning something every week and I have teach me something AI. And again, if it rotates, know, KK is going to teach us her best AI tip this week. Mark's going to teach us next week and next week I'm going to teach them. Everybody's best practices and people are going to learn things so they can teach them.Mark (06:39)andKK Anderson (06:42)it.Mark (06:43)Great. So we all know boards and CFOs fund what they can measure. funding is a big part of ensuring that you really are able to build the type of capabilities you're looking for and keep those skill sets building. So what three numbers belong on a page one to prove that change is working? And what targets would you maketo ensure that you can be confident that the program, the leadership you're bringing to the table is gonna create the lift now, this quarter, not quarters from now.Cherilynn Castleman (07:20)So the three numbers that I would look at, one is cycle time with a warm sponsor versus one without. So if you're doing this right and you're leveraging AI, it's very simple. You just want to say, here's what our cycle time is with a warm sponsor. We're seeing a lift in this. Number two, executive meetings by stage. So when do the executives join and what stage are you at? And being able to track that.and the win rate on multi-threaded deals. those are the three things. And what I think you're looking for is somewhere between a 10 and 20 percent quarter over quarter. That is proof that you are driving change.KK Anderson (07:56)Amen. That is proof. Okay, Sherlyn, we are gonna go to our favorite section of the podcast. We call it rapid fire. And Mark, I want you to kick us off so that we land on my favorite question on me. You go first.Cherilynn Castleman (07:58)atMark (08:07)You gotit. I'll start the first one. What is the first product or service you have ever sold?Cherilynn Castleman (08:15)Mark, I've been in sales since before Girl Scout Cookies were 50 cents a box.Mark (08:18)my goodness. Excellent.KK Anderson (08:19)did you do, Roscoecookies?Cherilynn Castleman (08:20)Every girl's got cookies. And I mean, I was probably in the first grade. Okay? And yeah, I was in the first grade and my brother would pull the wagon and then there were no order forms. They just gave you cookies and you went and sold them. And I would stand there and I just would say, you know, they freeze well. What's your favorite ones? And oh, and if you tried this, this is, know, and I'm telling you, you put them away, you freeze them, you'll have them at Christmas. And I just up-sold and I was...I a top salesperson and I just loved it. I was probably six years old.KK Anderson (08:51)That's amazing. Okay, who is one of your favorite sales or leadership voices that you like to follow?Cherilynn Castleman (08:56)So I have always followed who he was known as the client success guy and that was Bill Green, the former CEO of Accenture. He's just made such a change in the way I sold and Bill always said two things that stuck with me. One, if you criticize people, you raise their defensiveness. If you challenge people, you raise their game. And so that's why I coach and I challenge people.And the other thing he said, Sherrilyn, three C's. Competence, be damn good at your job. Be great at what you do. Confidence, just have confidence, have courage. And the last one, which I repeated here, is give a damn. Care about your clients, care about your industry, care about your product. He said the three C's, well, that is what makes you a great leader. And so I've read and listened to everything that Bill has done.Mark (09:48)right on. So one practice you believe every sales manager should adopt this quarter or maybe even this week.Cherilynn Castleman (09:56)I say curiosity. AI lets you be curious. ⁓ I was read in a couple of places that they say curiosity is the KPI for 2026 for sales leaders. So I think if you're going to leverage AI and build your AI fluency, curiosity, curiosity, just keep asking questions. What can I do better? And also one of my favorite prompts is what did I miss? What could I have done better?So even though you've done the prompt, you've done the analysis, stop and say, okay, what did I miss? What am I not thinking about? How can I do this better? So curiosity.Mark (10:28)So this may be one way that humanity is evolving a little bit, because they used to say curiosity killed the cat. And now it's not going that way anymore. And think about it, with AI, there's so much power in curiosity. So I really love that one. Thank you.Cherilynn Castleman (10:39)You knowYes.KK Anderson (10:46)So good, okay, and my favorite question. Okay, Sherrilyn, what advice would you give to your 21-year-old self?Cherilynn Castleman (10:52)So I would tell myself to trust my voice, trust myself earlier. I would tell myself, if given a choice, Sherrilyn, always choose kindness over being right. And the final one is always, always have the courage, regardless of what anybody else says, just have the courage, have the kindness, and trust yourself.Mark (11:13)All right, well, I'm gonna close this up with, and I'm really interested in this one with all the great stuff we learned about you during this call, Sheryl Lynn. What is your favorite non-business book?Cherilynn Castleman (11:24)The Untethered Soul. I read it every year. It makes me pause. It makes me spend a little more time on my rug. It is about self-reflection and choosing love over fear. And I've been reading it every year. I don't know, probably since it came out. I'm a voracious reader, but that is one book that I read every year. I love The Untethered Soul.Mark (11:28)Wow.And I love that idea of like reading something every year. I've never really, it's not like I haven't read books again, but the idea of having something that's so impactful and rereading it every year is really cool. Well, so.KK Anderson (12:02)Wait, when areyou going to release your book, Sherrilyn? Surely there's one coming.Cherilynn Castleman (12:05)Well, so I have a book. It was actually top of Amazon's best sellers for women. It's been recognized by Salesforce, actually one of the top 10 best sales books and link. You can go to post pandemic selling.com.And that's, you'll find out it's also on Amazon. It talks about a lot of things we've talked about coming out of the pandemic, why we had to connect with people, why people need us to be authentic and us to be curious and how to connect with people. It's called Post-Pandemic. It's what's in the cards. Post-Pandemic Selling is the name of it. Again, you can get it at postpandemicselling.com. You can also find it on my LinkedIn page orSherrilynCalfsman.com or just connect with me on LinkedIn.KK Anderson (12:48)You're right.Mark (12:48)Very cool.Cherilynn Castleman (12:49)Thank you.Mark (12:49)Well, Cherylin, thank you so much for taking the time with us. This was really a pleasure. And thank you to our amazing audience. I hope I remember that every single time. I don't know if I do, but we want to thank them as well, especially as we're moving in and through the holiday season. So again, Cherylin, thank you. KK, thanks to you as well.Cherilynn Castleman (13:12)Thank you, KK. Thank you, Mark. And thank you to your listeners and your audience.KK Anderson (13:15)Make sure to check the show notes and to catch Sherilyn's LinkedIn Lives. They're awesome. Almost every week. Okay. Thanks everybody.Cherilynn Castleman (13:20)Thank you, Kate.See Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info.