Episode 462: Why Caring Is the Future of Social Selling: A CRO’s Guide to Alignment, AI & Authenticity

Shawn Sandy 00:00
I believe you have to show that you care, and caring about someone means listening to them. It’s not talking at them; it’s listening to them and asking them questions.

Intro 00:10
Welcome to the Making Sales Social Podcast, featuring the top voices in sales, marketing, and business. Join Brynne Tillman and me, Bob Woods, as we bring you the best tips and strategies our guests are teaching their clients, so you can leverage them for your own virtual and social selling. Enjoy the show.

Brynne Tillman 00:35
Welcome back to Making Sales Social. I’m Brynne Tillman, and today I am thrilled to welcome Shawn Carroll Sandy—actually a real-life friend. Shawn is a nationally respected sales strategist, keynote speaker, and founder of The Selling Agency. With deep Memphis roots and a passion for helping teams grow, her quest to be challenged has led her to her latest role as the Chief Revenue Officer of ProTech Services Group, an innovative IT services and cybersecurity firm in Memphis.

Her role as CRO brings her to designing scalable, customer-centered revenue systems that support clients and the community at every stage of their journey. With experience in nearly every role across the business development ecosystem, she brings a unique perspective on building RevOps and the CRO role from the ground up. We’re going to dive into Shawn’s expertise today, hear her insights on aligning sales and marketing, what’s next for revenue generation, and even stories about how she landed her role today. My friend Shawn, welcome to the program.

Shawn Sandy 01:52
Hey, Brynne. It’s good to see you.

Brynne Tillman 01:54
It’s good to see you too. I was so excited to see you in this position, and when we decided we were interviewing CROs, I thought, “I’ve got to get you on the show.” So here you are.

Before we jump into your genius, we ask all of our guests the same first question: What does “making sales social” mean to you?

Shawn Sandy 02:21
It means you have to care—and that you do care. I was talking at a conference recently, and everyone wanted to know, “How do I get more engagement and likes?” They were all salespeople, and I thought, “To what end are you doing this? Vanity metrics?” Do you care about your audience?

I care about business leaders making sure they are protected, that they understand the risks of using AI, and how those risks can undermine their cybersecurity efforts. I care that when I’m reaching out to someone, I care. That, to me, is what social selling means.

For those of us who’ve been around the social selling block, it has meant a lot of things, and some people have taken it out of context and done crazy stuff. But at the heart of it, you have to show that you care—and caring means listening. It’s not talking at them; it’s listening, asking questions, supporting their initiatives. Everything you’d do if you cared about someone in real life, translated into connecting and providing value online.

Brynne Tillman 03:43
I love that. I always say there’s a human being on the other side of that message—not a lead. So I love that.

I’m really excited to jump into your CRO role and the alignment of sales and marketing, which fascinates me. I focus on that social selling, LinkedIn world for sales, so I’m always thinking: how are sales and revenue leaders bringing the two together?

Talk to me about your role at ProTech as their first CRO and how you’re approaching the challenge of bringing sales and marketing together.

Shawn Sandy 04:29
I wanted this. I tell myself that every day—I asked for this. I was looking for a big change. In my heart, I knew I needed a new challenge from consulting and agency life. I found a company whose culture I loved, and they had the right pieces to build RevOps, or what I call a business development ecosystem.

I found a way to talk to the CEO. We were talking about training, but I knew I was going to pitch RevOps. I said, “You have all the right pieces. Let me explain RevOps and what a Chief Revenue Officer can do.” I explained it and said, “By the way, I’m your girl.”

I think of marketing, sales, and service as this small ecosystem.

Brynne Tillman 05:26
For those listening, it’s like a tiny terrarium—your ecosystem.

Shawn Sandy 05:33
Exactly. It’s a closed environment. You have lead generation (marketing), revenue generation (sales), and retention/account growth (customer service). Traditionally, we’ve treated this like a linear flow—marketing sets strategy, sales sells, customer service delivers. But we haven’t treated it as an ecosystem.

What kind of soil do we have? What are we planting? Are we nurturing it? And at the end, RevOps takes the information we learn and puts it back into the ecosystem.

Brynne Tillman 06:22
A self-sustaining ecosystem. Yes.

Shawn Sandy 06:25
Exactly. Customer service data rarely gets back to marketing to inform strategy. Sales information often doesn’t get to customer service, much less make its way back to marketing. We need to break down silos so the environment feeds itself and everyone thrives.

It’s not about “the business thrives but who cares about the customer?” You want your customers to thrive too. That’s why I think of it as an ecosystem.

Brynne Tillman 07:30
I love that. So you came in as the first CRO. What were the challenges? Was it breaking down silos? Was it unifying around one goal?

Shawn Sandy 07:55
This company has been successful for 33 years, so they were doing something right. But like many long-standing companies, there were a lot of Mavericks, a lot of cowboys—disparate business units doing their own thing. So instead of one ecosystem, we had multiple little terrariums. And it wasn’t scalable.

The most important issue was scalability.

There also wasn’t cohesive, strategic, company-wide marketing. So we had to build a foundation for lead generation and marketing—not visibility, because people already know us, but trust, credibility, and leadership in the market.

At the same time, we had to understand who does what, how we’ve done it, and how to put systems around it to capture success. Systems and processes are huge.

Brynne Tillman 09:14
Huge. So when you walk into disparate systems—CRM, marketing, tools—do you just take a full inventory? What do we need? What don’t we need? What works?

It seems like such a big task.

Shawn Sandy 09:37
It is. Fortunately, we had a CRM, but it was messy. And when you don’t understand the end goal of connecting a CRM (used for a decade) with a marketing automation platform (barely used), you don’t build the CRM in a way that supports automation.

So we had to understand: Where is our information? What’s accurate? What needs cleanup? And how do we still sell and serve clients while cleaning the closets?

You know how you start cleaning a closet, and halfway through the whole room is a mess? That’s what this is like—except we still have to run the business.

We had to do a process inventory—not just tech stack, but why we used it, how we used it, what we put into it, and why we thought that was a good idea at the time.

When I trained sales teams, I realized training isn’t sticky without strategy. Most companies don’t have an actual sales or go-to-market strategy. Same here: without a strategy for lead generation and revenue generation, choosing tools gets messy. Then later, you need strategy and realize the tools or data aren’t right.

So there’s a lot of cleanup—but also a lot of progress.

Brynne Tillman 12:21
And like cleaning the closet, you dump everything out and start folding. Yes. The donate pile. I get it.

So let’s talk about automation and specifically AI—the elephant in every room. How are you approaching AI for the company, from both marketing and sales, for content, research, and data?

Shawn Sandy 13:02
It’s interesting. Being in an IT and cybersecurity company, AI is both awesome and scary. The risks and vulnerabilities AI creates are huge—it can help attackers get around cybersecurity measures. So we’re the ones informing clients about these threats.

We’re thinking through it internally too. We’re using AI to be better humans—more creative and more efficient. Automation will replace some jobs, but people who know how to use AI will be fine.

For marketing and lead gen, it’s fantastic for understanding customers: asking questions, finding patterns, extracting insights, mapping micro-industries, and identifying the buying committee personas. Then overlaying that with our own data to create account-based marketing for every prospect. Hyper ABM.

I think we’ll see tech stacks collapse and companies creating their own agentic AI systems—feeding the AI your data and letting it build playbooks, making sellers more connected and able to anticipate buyer needs.

Large enterprises will adopt this faster because they can invest in it—hire a chief AI officer, build teams. SMBs will be slower.

Brynne Tillman 16:59
Let me share something every team can do at a very reasonable price—something that has transformed how I look at data.

I use my AI assistant—Sybil.ai. Others use Fathom or Otter. Every sales call gets recorded and transcribed. Everything is available to me. I can ask: “What’s the number one objection we’re hearing across all sales calls?” and in 30 seconds, it cites conversations, how reps handled it, who handled it better, etc.

AI agents are becoming the best data source. You don’t even have to pull coaching calls manually anymore. It tells you which calls need coaching.

Speaker 2 18:23
I remember when we used to pull tapes for coaching calls.

Brynne Tillman 18:27
Now AI tells you which calls matter. It’s amazing.

Shawn Sandy 18:34
Yes. It’s similar to that company we all know—the one whose name sounds like what happens when you hit a drum and it goes boom.

Brynne Tillman 18:44
I actually love them.

Shawn Sandy 18:46
They’ve got wonderful features. But with tools like you’re using—or Microsoft Copilot—you can build a notebook, dump data into it, and then build onboarding, coaching, or marketing programs from it.

My marketing hire—she’s phenomenal—collects everything into a notebook: marketing materials, brand identity, collateral. Then AI creates what we need next based on that.

This is how small teams thrive—you master these tools for productivity.

Brynne Tillman 19:40
I love that. I know you’re a Microsoft partner. Since Teams and Copilot work together in many ways, how are you empowering your team to leverage AI on an individual basis? What does “sharp” look like?

Shawn Sandy 20:03
Yeah, well, in our organization, it started with the sales team. What we’ve done is build campaigns, blitzes, and different things, and wrap the lesson around: How did I build this using AI? Then we let them go and say, “Okay, use these things. Here’s how we did it so you can build your own and scale what we’re doing.” We’re helping them scale their own efforts.

So if this is a campaign on physical security, access point control—fun stuff, right?—we show: Here’s how I built it. Here’s how you can customize it for the manufacturing industry, so they’re able to run faster. It’s not necessarily doing more—well, they are doing more and running faster—but being more specific and more social. It shows they care because they understand more about the prospect. Like, someone with a bunch of cranes on their property needs cameras at every access point, etc. So they can show, “I care about understanding, and I care about what you care about.” That helps them go faster.

Our training guru is using AI to create new training and understand how to match personas and industries, customizing training simply by feeding it prompts. That’s another way to use it. And I can’t even tell you what our network engineers and our pre-sales engineers are doing because, honestly, I don’t understand it. It’s just—

Brynne Tillman 21:51
—magic.

Shawn Sandy 21:53
It’s magic. I tell everyone it’s easy to recognize who in your organization is an AI champion. It’s like CrossFit—you know who does CrossFit because everyone who does CrossFit tells you to do CrossFit. And everyone who uses AI is going to tell you all about AI, too.

Brynne Tillman 22:13
That’s right. We’re going to wear it on our shirts. I love it. Now, as we wrap up, I want to ask you about your social selling story through Monkey Sphere.

Shawn Sandy 22:26
Okay, so this was something my husband brought to my attention. I don’t know if you remember Cracked.com, but they had great content. I was looking for ways to explain social selling and help people stop blasting people with messages.

I found this article and shared it. Here’s the story: An anthropologist named Robin Dunbar did a study and came up with Dunbar’s Number. He studied monkeys and primates and realized that monkeys and humans can only hold a certain number of meaningful social relationships. For humans, it’s 150. Everyone outside of that doesn’t really register.

The example they gave was this: One day, a child asked his dad, “Why are you wrapping the glass in newspaper before putting it in the garbage? Why does it matter?” His dad said, “I don’t want Roy to cut his hands when he picks it up and puts it in the truck.” The kid says, “Who’s Roy?” The dad replies, “He’s the garbage man—we talk. I’ll bring him a bottle of water sometimes.”

Roy was in the dad’s Monkey Sphere, but not the son’s.

From a selling perspective, it’s interesting: We need to get people into our Monkey Sphere to show we care. But to do that, we have to knock someone out of their sphere, because they can only hold 150 relationships. So if someone already has an incumbent vendor, you have to displace a relationship by creating a new one and showing genuine care.

That is the power of thinking about social selling and relationship selling through the Monkey Sphere: We want people to care about us so we can enter their sphere.

Brynne Tillman 24:22
I love that. And if that son wants to get into the Monkey Sphere, going through his father is the best way in.

Shawn Sandy 24:29
Exactly. Someone already in their Monkey Sphere can transfer credibility and trust. An introduction creates that transference.

Brynne Tillman 24:44
We could have fun all day, but we do need to wrap this up. What’s one question I should have asked you that I didn’t?

Shawn Sandy 24:53
Ask me where my next adventure is.

Brynne Tillman 24:55
Where’s your next adventure, Shawn?

Shawn Sandy 25:00
Patagonia—Chile and Argentina—in January and February.

Brynne Tillman 25:05
Oh my gosh, enjoy! That’s amazing.

Shawn Sandy 25:09
I’m dreaming of it. I’m in Memphis, and you don’t understand—it’s still 95 degrees outside. I’m dreaming of glacier walks.

Brynne Tillman 25:16
How amazing! I’m so excited for you. Well, thank you so much. If people want to get a hold of you…

Shawn Sandy 25:24
Find me on LinkedIn—Shawn Carroll Sandy. Carroll with a K. I don’t know why they spelled it that way. Who knows? But you can find me.

Brynne Tillman 25:33
It’s awesome. Thank you, my friend. I appreciate it. And to all of our listeners, when you’re out and about, don’t forget to make your sales social.

Outro 25:43
Thanks for watching. Join us again for more special guest instructors bringing you marketing, sales training, and social selling strategies that will set you apart. Hit the subscribe button below to get the latest episodes from the Making Sales Social podcast. Give this video a thumbs up and comment below on what you want to hear next. You can also listen on  Apple Podcasts, Spotify, Youtube Music, and Amazon Music. Visit our website, socialsaleslink.com, for more information.