175. How CS Leaders Can Build Relationships Between Meetings to Drive Retention & Expansion ft. Darren McKee (531)

Like, that means—

Josh Schachter [Host]:
but I want to stop you on that because it makes sense. Like, should people be incentivized financially for posting their company? So, so actually, let me, let me, let me sit back one second.

Darren McKee:
Opening a can of worms.

Josh Schachter [Host]:
Opening a can— before I open the can, I already opened it and you can’t put it back in. But like, you need folks to take time to do this, right? And I think you’re a believer in blocking out your calendar, like having that dedicated half hour or whatever it is. So explain a little bit about that. And then if we are going to have sellers and other people that are taking a concerted effort, amount of their time, then like, yeah, should they be compensated for that?

Darren McKee:
Yeah.

Josh Schachter [Host]:
Hey everybody, and welcome to this episode of Unchurned. I’m your host, Josh Schachter, Senior Vice President of Strategy and Market Development at Gainsight. And I am here today with Darren McKee. Who is Darren McKee? He is somebody that you either really know or really don’t know. But either way, I’m really excited to have him on the show. So, Darren, thank you so much for being here.

Darren McKee:
Yeah, man, I’m excited to be here. I love being known. I love being not known. That means there’s an opportunity for me to continue to hop on these things and get those people to know me. So, yeah, I’m excited to be here and looking forward to diving in.

Josh Schachter [Host]:
Life is all about dichotomy. Okay, what do you do?

Darren McKee:
Yeah, it’s a great question. I help people uncover relationships and revenue that they never knew existed. And I do that by helping people create content on LinkedIn, engage on LinkedIn, and then book meetings on LinkedIn, and then generate revenue to grow their businesses. It’s exactly what I do all day, every day.

Josh Schachter [Host]:
That’s amazing.

Darren McKee:
Yeah.

Josh Schachter [Host]:
Do you enjoy it?

Darren McKee:
I love it. I had somebody ask me two nights ago, I was in Raleigh at an event, and they said, do you love what you do? And I was like, man, I actually love waking up and doing this every single day. Because for the longest time, I had so many people tell me that like this wasn’t a viable business. And now I’m here doing really fun things all around the world.

Josh Schachter [Host]:
You’re thriving. I joke that you’re the number 2 best social seller in the world. But you know, in my heart, you know that you’re number 1.

Darren McKee:
Yeah, there’s always room now to get to number 1.

Josh Schachter [Host]:
No, but people do know you, right? So you’ve got 146,000 followers.

Darren McKee:
Yeah.

Josh Schachter [Host]:
You have been posting for over 3,000 days in a row.

Darren McKee:
Something like that. March 3rd, 2020 was the first day. So do the math. I don’t know what it is now. Something like that.

Josh Schachter [Host]:
Wait, March 3rd, 2020? That sounds kind of like a COVID thing.

Darren McKee:
It was during COVID That’s like the beginning of like lockdown content. Yeah, that’s how all this started.

Josh Schachter [Host]:
Yeah, true, actually.

Darren McKee:
Do you want me to tell that story?

Josh Schachter [Host]:
Yeah, let’s, yeah, tell that story.

Darren McKee:
Yeah, so I mean, I was selling payroll and benefits and it used to be like handshakes and knocking on doors and going to networking events and all of a sudden like my boss was like, you can’t do any of that stuff anymore. And I was like, well, I’ve got a family and a kid to feed and LinkedIn seemed like the only viable option to start creating content, but I hadn’t really done anything. I’d like just like shared job postings and stuff about the company and then all of a sudden And I was like, “All right, cool, I’ll start.” And then 2 people liked my content and then 4 and then 5 and then 50 and then 90 million. And then I was like, “Wow, this is actually a really viable thing.” And so that’s kind of how it all started and still doing it today.

Josh Schachter [Host]:
So you didn’t get into it with this aspiration of being able to go into your own consulting and coaching and now you’re starting a platform as well.

Darren McKee:
Yeah.

Josh Schachter [Host]:
Like this, it was just you, this is, was it survival mode? Was it like—

Darren McKee:
Oh yeah, 100% survival. Yeah. I mean, it was just, it was to make money, right? Like it was to get first meetings, it was to close deals and it was to hit my quota. That was the reason. I also love writing, so it was a little bit of a creative outlet too. But, you know, instead of in my little binders now, I just put it online for the world to see.

Josh Schachter [Host]:
How much do you actually have to love writing to be like a LinkedIn influencer these days? I wonder sometimes, like people’s authenticity.

Darren McKee:
Yeah. And I think about the influencer word a lot, right? Like, and it’s because it’s just thrown around so much. I think more often the way that I would look at myself as somebody that just got really good at a craft and shared a lot about that craft, then was able to have a little bit of influence in that world. I mean, it does take time. It takes effort. It takes study. It takes you being willing to fail a lot, right? I think we’re in this timeframe where like, if you don’t go viral, if you don’t do amazing stuff, every time you press the post button, you get defeated. And that’s just not reality.

Darren McKee:
I mean, it took me probably 15 months of posting content every single day to get to the point where I was like, okay, I I think I figured this out a little bit. But the majority of people quit at like day 9.

Josh Schachter [Host]:
I mean, listen, it helps that your uncle is the head of algorithms at LinkedIn.

Darren McKee:
Yeah, if that were only true, that’d be amazing.

Josh Schachter [Host]:
I’m convinced. But how do you, so like what is your secret sauce there? Like how did you go from 0 to 146K followership? I know it’s, by the way, I know it’s not about followership. That’s bullshit, right? That’s a vanity metric. I’m still trying to divorce myself from it. But it’s about like the outcomes of that followership, right? But like anyways, we’ll get a bit more into that later. How did you go about mastering it?

Darren McKee:
Yeah, I mean, I just like, I’ve always been the person that loves to tell stories. I’ve loved to be the person that loves to teach people how to actually do things. I’ve loved being the person that doesn’t gate everything to make people like do extra effort to figure out how to do these things. And so for me, I was like, you know what, I’m just going to put myself in uncomfortable situations, you know, over and over and over again. And it just started to—

Josh Schachter [Host]:
Like being on this podcast.

Darren McKee:
Yeah, like being on this podcast. Oh, this is fun. I love doing this stuff. But yeah, I mean, it was just doing it over and over again. And I, you know, I talk about David Goggins a lot because I’m not, I’m not a huge fan, but like just continuing to go, right? More of a Cal Ripken type situation where it’s like, if I just, if I commit and do this thing all day, every day, then eventually like I’m going to get good at it, right? If only that would happen with golf, we would be in a good position.

Josh Schachter [Host]:
But do you, do you study your, your feedback loop there?

Darren McKee:
Yeah. Yeah. Study a lot, right? So I look at, other creators that are ahead of me, right? I look at other creators that are slightly behind me. I look at my content on months that like didn’t perform well and I’m like, okay, well, was I on platform less? Was I engaging less? Was my content not as helpful? Did I share more pictures? Did I share more videos? Was I sharing more long form? And the one thing that I’ve realized over the years is that like you can’t just create one type of content. So I learned this from a 5th grade social studies teacher in Raleigh-Durham. She was like, you have to you have to create content for everyone or you’re only going to get that one type of human that loves video.

Josh Schachter [Host]:
Yeah.

Darren McKee:
So I really have to try to pivot. And that takes time, that takes study, that takes coaching. And yeah, I mean, every single day I’m, I’m diving in. So the 10,000-hour rule is like, it’s truly real.

Josh Schachter [Host]:
Wow. You’ve been learning about LinkedIn posting since the fifth grade. That’s impressive, Darren. That’s—

Darren McKee:
I was on a panel with a fifth-grade social studies teacher.

Josh Schachter [Host]:
I know, I know, I know. Okay, so I’ve buried it a little bit here in the intro. But our audience, our listeners in go-to-market, you know, primary ICP for us, let’s say, is post-sales, customer success, but also sales leaders and other practitioners in go-to-market and SaaS and other worlds. Yeah. For the sellers, maybe it’s more obvious.

Darren McKee:
Yeah.

Josh Schachter [Host]:
For the CSMs and post-sales world.

Darren McKee:
Yeah.

Josh Schachter [Host]:
Why are you on this show? Why do you matter?

Darren McKee:
Yeah, it’s as a— it’s never been an easier time to vanish overnight. As a seller, as somebody that’s an account manager, as somebody that’s customer success. And so you have to be on the forefront of your prospects’ and customers’ mind all day, every day. So like, yes, you’re going to be doing the emails and the nurtures and yes, you’re going to be inviting them to dinners and yes, you’re going to be doing the QBRs. But like, you need to show up in their feed on a daily basis. You need to show up in their content, right? It’s just, it’s, it’s huge for churn. It’s huge for expansion. It’s huge for new logos.

Darren McKee:
And You know, I typically sell into CROs, CMOs, but a lot of CS leaders are starting to adapt this and say, why can’t we, why can’t we lead this? Why can’t we be at the forefront of organic social content and LinkedIn? So yeah, it’s fun. It’s, it’s, it’s critical.

Josh Schachter [Host]:
So but just to reiterate what they’re seeing, what they’re coming to you and what you’re also saying is it’s important for them to be out there building relationships to drive their commercial goals, even if those goals are GRR and retention. Yeah, not necessarily as much of like chasing the sale as a seller might be. You still think that this stuff really matters?

Darren McKee:
100%. I mean, I think about CS a lot, right? Like the goal— I’ve never been a CS leader, so it’s hard for me to say this on this podcast, but like I would assume that that goal is to make sure that my buyers come to me and my customers come to me to learn something, right? Like I want to be the person that my contact calls and says, hey, what’s happening in the space? And like, can I share about that stuff, right? That’s important.

Josh Schachter [Host]:
Actually, you know what? It’s funny because we were just in a call yesterday, our team, leadership and we were talking about, I mean, it’s a time of reinvention right now for customer success in so many ways.

Darren McKee:
Yeah.

Josh Schachter [Host]:
You know, with, with Agentic and just with CS in general and for Gainsight too, there’s lots of change going on and we’re like, you know, we need our team, our CSMs, our professional services, our go-to-market team to be thought of as, we already are thought of as this, but to continue being thought of as leaders and guides for people that are trying to figure out like what this next wave of CS really means.

Darren McKee:
Yeah.

Josh Schachter [Host]:
So that’s what you’re saying.

Darren McKee:
Yeah, they’ve gotta be the teachers.

Josh Schachter [Host]:
They’ve gotta be the teachers.

Darren McKee:
Like they’ve gotta be the people that people are coming to to learn from, not just be told that there’s a new feature that’s launching that’s gonna help their business. That’s not helpful.

Josh Schachter [Host]:
But then why am I posting photos of Jackson, my dog, in Central Park during snow day?

Darren McKee:
Yeah, ’cause if you wanna go back like years where we used to say people do business with people they know, like, and trust, digitally that’s really hard now. And so the only way to know, like, and trust someone digitally is to actually know the whole person of that human being, you know, their hero story, their journey story, what they do for work, what they do outside of work, who they hang out with. And once you know all of that stuff, it’s really hard to not do business with that person, right? So the dog picture is like, oh wow, I have a dog, you have a dog, I lead CS, you work at Gainsight, like, I guess we can talk, right? But if I see only just stuff about like all the features that you all are dropping, like, Cool, you’re just another employee.

Josh Schachter [Host]:
Yeah, you’re looking for commonality.

Darren McKee:
Commonality, right? It’s just human behavior. And I think it’s never been a more important time to focus on that.

Josh Schachter [Host]:
Yeah. Online.

Darren McKee:
Online. Yeah.

Josh Schachter [Host]:
IRL, but IRL, right?

Darren McKee:
Like, it’s like, you know, yeah, for sure. You’ve got to be a human online now because it’s hard to tell, quite frankly, what’s AI and what’s not. And yeah, if you can, if you can be seen as a human, you’re going to thrive.

Josh Schachter [Host]:
So I’m online a lot. I’m all over LinkedIn. I’ll be honest with you, I don’t really enjoy it. I’m pretty open about that. I think I’m not supposed to break the third wall or whatever they say it is. I’m not supposed to admit that, but I don’t. I really don’t. I really don’t.

Josh Schachter [Host]:
I’m doing it for, I’ll be totally honest, I do it for transactional purposes, for the growth of myself and gain sight professionally. I don’t have any other social— So you like it sometimes? There’s a small little nugget inside me that likes it or likes to needle with people. I don’t have Instagram or TikTok or anything else. But, but as I’m doing it and I am doing it with intent.

Darren McKee:
Yeah.

Josh Schachter [Host]:
Most of the time I’m also a little bit incredulous that it will move the needle in terms of building pipeline and, and converting to sales and, you know, or expansion or whatever. How do you know that it does?

Darren McKee:
Yeah, I mean, my business started because I saw success for myself doing this. So going back from being an SDR to a SMB to a mid-market to an enterprise, a VP of sales to selling that company. And we, when I look back at like every single deal that I’ve closed, ’cause I had to report this to the board when we sold the last company, 81% of our deals were from LinkedIn and social selling. And so what does that mean though for you listening? Like that means somebody came inbound via a piece of content. That means somebody responded to my amazing comment on their post about their business. And then we got into the DMs and started having a conversation. That means that I emailed somebody 27 times over the course of 16 months and then they saw a personal post about me being from Victoria, Texas, and then them saying, oh my gosh, and then looking and seeing all of those messages, right? Like, it’s just, it, again, I’m going to say it over again, it’s just increasing luck proximity. You can’t just do what we used to do and expect that it’s going to work now.

Darren McKee:
And yeah, I mean, it’s changed my entire life. Large, large enterprise logos, you know, last company we were like $2 million in ARR, taking business from $300 million ARR businesses from just being active and social.

Josh Schachter [Host]:
But I want to stop you on that because it makes sense. I come from the startup world, right? I had Updated AI and I was doing a lot of this LinkedIn stuff and it really helped propel me in many ways. But you talk about the $2 million ARR company. So totally get it if you’re the minnow in there that’s growing your brand. And we all know the startup founders that are doing that well and they’re kind of annoying, but in a jealousy way. But I digress. But if you are Gainsight, you’re well over $100 million ARR. We just were in this room a second ago talking to to Cassie Vaughn, a leader at monday.com, and then she came out and talked to you and she’s like, oh, I’m really interested in social selling and LinkedIn for monday.com.

Josh Schachter [Host]:
And they’re like a billion-dollar company. Does it still really matter? Because it feels like—

Darren McKee:
Yeah, yeah, it still deeply matters because like you all are still trying to grow. And as you think that you’re big and you think you’re the industry leader, while you are, there’s still so much opportunity out there of people that don’t understand, right? And so when you get out there and you’re creating that content, you get to that tipping point. I talk to this a lot with all of my clients, which is 20% of your staff creating content. Listen, this is not just CS, this is not just sales, this is product, this is eng, this is finance, this is people ops. Like once we start like getting that rolling, everything starts to change. And this is a marketing engine first, revenue engine second. And so instead of spending a couple million bucks to get 90 million impressions on content, your people are just sharing organically, right? And it just starts to trickle. And the way that LinkedIn works, which a lot of you might not know this and some of you might, is that when I’m engaging with my, my customers or my prospects on a daily basis and then I’m creating that really good content, it’s going to marry the two in the feed, right? And so when there’s a bunch of Gainsight employees inside of the LinkedIn feed of all of their prospects, it’s really hard to them to think about any other competitor in the market.

Darren McKee:
And so it just creates a swell.

Josh Schachter [Host]:
I’ve noticed you keep a lot of your— well, when we first started texting or chatting, right? Texting, chatting. No, we actually weren’t texting. We were—

Darren McKee:
Writing notes.

Josh Schachter [Host]:
Writing notes, passing notes. We were on LinkedIn. You used a lot of LinkedIn messaging.

Darren McKee:
For sure.

Josh Schachter [Host]:
And I think that’s strategic for you.

Darren McKee:
Yeah.

Josh Schachter [Host]:
Yeah.

Darren McKee:
I mean, I sent a lot.

Josh Schachter [Host]:
It’s like your outbound.

Darren McKee:
For anybody that’s been through coaching with me, I’ve sent 50 DMs for the last like 3 and a half years every single day.

Josh Schachter [Host]:
But it’s because you know that LinkedIn is watching, big brother.

Darren McKee:
No, no, that’s not, I mean—

Josh Schachter [Host]:
They want you active on the platform.

Darren McKee:
Oh, everybody else sends emails.

Josh Schachter [Host]:
Oh, that’s why.

Darren McKee:
Yeah, I mean, and so for me to send a video DM to the, you know, CS leader of, you know, ABC company, like they’re not gonna get another deep detailed video DM from anybody else today, but they’re gonna get anywhere between 60 to 140 emails a day from sellers in our market. So I’m just trying to do something that’s a little bit different, right? And so I’ve sent thousands of video DMs over the years to, V and C-suite leaders.

Josh Schachter [Host]:
So you’re doing it for purple cow effect. You’re not doing it because, because LinkedIn is seeing your metrics that you’re engaging with that person behind the scenes and then therefore they’re going to put your stuff in their newsfeed.

Darren McKee:
Well, that’s just what happens. But no, I’m doing it to, to get them to respond to me. Right. It’s not just like a checkbox thing. Right. And so that’s why, that’s why I focus a lot when I do my trainings is like, hey, I don’t want you to send some templated message out to all of your prospects about something that’s happening. Like, no, go study the darn company, like understand what they do, how they make money, what their revenue is, and send a good pitch, right, to that person.

Josh Schachter [Host]:
And then put it into a, uh, a Agentic LinkedIn automation tool and then press go.

Darren McKee:
Yeah, minus all of the last sentence.

Josh Schachter [Host]:
Let’s talk about that.

Darren McKee:
Yeah, um, I think we’re in a time, uh, of everything is automation, everything is Agentic, everything is quick, everything is short, everything is like make this happen now. Um, and the problem with that is we’ve outsourced a lot of the actual effort that we do to build relationships. And so LinkedIn’s one of the cool platforms that doesn’t, quite frankly, allow a lot of that stuff legally. And so if you can be a human, you can write human content, you can write human comments, you can write human DMs, you’re going to stand out wildly in the feed. And so that’s what I coach all of our teams on. It’s interesting because I go into these companies that are like very agentic forward and AI forward. And then within like 45 minutes, we’re talking about like how to teach people how to storytell again.

Josh Schachter [Host]:
You know, you told me a few times that like storytelling, that as a role is now like a growing—

Darren McKee:
Yeah, I mean, you can go on LinkedIn, look at jobs right now, head of content, head of storytelling. It’s all the rave right now because we’ve lost the ability to tell a story to our prospects.

Josh Schachter [Host]:
How do you tell the story on LinkedIn? What are your pillars?

Darren McKee:
Yeah, so I walk through 4 pillars and the first one is that hero journey story of like where you came from. Everybody loves to know where you came from. They love to know how you got into the role that you’re in today. So walk through that journey wins and losses. Everybody wants to talk about their wins. Talk about failures, right? That’s what people would like really deeply identify with. Flashback photos, you on your come up, right? Those are extremely important. And then pillar 2 is company content.

Darren McKee:
It’s self-promotion content. It’s not being afraid to tell a story to a VP of CS of Monday about, you know, a tool and how we can help fix a problem that they might have, right? But it can’t just be like, Hey, we’re so excited to announce this new thing. And then everybody in the company reshares that exact same post for marketing. Like, that’s like—

Josh Schachter [Host]:
Oh, like what I had LinkedIn do? What I had Gainsight do 2 weeks ago?

Darren McKee:
That’s like an absolute— like, we just, we, we, it just, you know, we used to say the word like burns your TAM. That’s exactly what it’s doing on LinkedIn, right? So it’s like, well, you’re not unique anymore. You don’t like— you’re not sharing things that can actually help me. So really tell a story about like how you can change the life of your prospect. The easiest way to do that is like if there’s a Slack channel or a Teams channel with win stories, like analyze those things, help the team tell a story on that. Number 3 is like nothing to do with work. Like we’re humans first and we’re workers second. Yeah.

Darren McKee:
So you really need to make sure that people understand like who you are as a human being. Yeah. I mean, I learned a lot about that when I was at BetterUp, just like understanding that people do care about What you do outside of work. And then the third one is just like pictures of you with other humans. I call this the collaboration pillar. So it’s like you at a dinner, you with partners, you walking down the street, you going to get lunch with a colleague, us filming this podcast together. Like people don’t want you to be the psycho founder or employee that’s sitting in their office working 16 hours.

Josh Schachter [Host]:
It feels so narcissistic. I do it because it, like, again, transactional. It just feels so narcissistic putting those photos of like myself, like pretending to be at the computer because I’m typing, I’m frustrated on some problem or blah, blah, blah. I don’t know. I vent. You don’t have to respond to that.

Darren McKee:
Yeah. People love faces.

Josh Schachter [Host]:
You’re right. People love faces.

Darren McKee:
Yeah. And look at your face.

Josh Schachter [Host]:
Yeah. Well, I mean, voice for a podcast or face for a podcast. Write your post, write your first pillar for us right now about your hero journey, your founder story. You probably already have written it years ago or you probably recycle it every 6 months, right? But like—

Darren McKee:
I do. I recycle it a lot.

Josh Schachter [Host]:
Which you should, right?

Darren McKee:
Yeah. Yeah. I mean, listen, Gary Vaynerchuk, Alex O’Hanian.

Josh Schachter [Host]:
You know what’s funny? As you talk about this, Gary Vaynerchuk, right? I actually shook his hand once. I was listening to some, it’s something he was at 6 or 7 years ago, right? And you know what’s so funny? All that I remember of Gary Vaynerchuk is he had some startup that I invested in that lost all my money from that investment. But the only thing I remember from Gary V, I don’t really follow him, right? But I was like this one little fireside chat session, actually in this building at Hudson Yards in New York. And he was talking about his story of collecting and selling baseball cards growing up in New Jersey. And that was his start into entrepreneurship. And that’s the only thing— It’s so funny you mentioned that.

Darren McKee:
Well, he also tells it over and over again and the wine story, right? And so it’s like, but that’s the reason you remember it is because he, even as somebody that we all know, is still sharing his journey over and over again. Alex Ohanian talks about like Sarah Blakely talks, Jesse Itzler talks about it over and over and over again. And so for us to not think that we should be sharing that is like doing a disservice to ourselves and our community.

Josh Schachter [Host]:
But again, going back to like the, the, the, the megalomaniacal, like narcissistic, ego-driven, like, isn’t it like really I’m going to tell my story to everybody like every 6 months?

Darren McKee:
Yeah.

Josh Schachter [Host]:
Do you—

Darren McKee:
so here’s the question that I ask every single founder or leader that has that question to me, like, Do you truthfully think that what you’re talking about can change the life of the employee or the client that you’re supporting?

Josh Schachter [Host]:
I think what you’re trying to get at is that to do it right, it needs to come from that place.

Darren McKee:
Yeah. Well, and if you, if you don’t share that thing, that might be like, you know, all about you or the business and your customer can’t find that out. They can’t go then change their company’s lives, right? Like, that’s just the part that I think about a lot. If I don’t talk about LinkedIn and social selling, Well, that founder that didn’t know about me can’t now come to me and then book a ton of meetings and change his business and raise around and have a wonderful life for his family and all of his employees. Right. So like, I have to share that stuff. It’s doing a disservice to my entire community if I don’t do that.

Josh Schachter [Host]:
But Adam Grant talks about that a lot. That’s you. I love Adam Grant. That’s you as a solopreneur, right? Yeah.

Darren McKee:
Like even more so as a leader.

Josh Schachter [Host]:
So me talking about my— well, let’s go talk about your— yeah, let’s go write your post.

Darren McKee:
Yeah. So if I’m going back, like hero journey, like I’m in this awesome building right now in Hudson Yards and what, I was 12 and a half years ago delivering mail up and down the streets of Manhattan, making $12 an hour and looking up at these buildings and wondering what the heck are all these people doing in there. And so now fast forward, you know, 12, 13 years later, I’m sitting in here in this insane space filming this podcast with a, you know, $100 million plus ARR business talking about like me delivering mail in Manhattan, right? So that would be my post, right? And a picture of me back then and a picture of me today. Hell, I might just make that post in a little bit, right? Um, but that’s the, that’s what people want to understand when I’m in the room.

Josh Schachter [Host]:
That did not help me at all.

Darren McKee:
Yeah. You gotta know your story.

Josh Schachter [Host]:
That didn’t help me personally hearing your story. Oh, it’s a nice story. Like I like you as a person, you know that. So like it’s cool and it’s interesting, I guess, but it didn’t actually help me.

Darren McKee:
Yeah. So the interesting thing about that is, um, As I get into final stages of large enterprise deals, what typically comes up is, hey, I remember that mailroom post. That’s what brought me to the second pillar post where you were talking about the business.

Josh Schachter [Host]:
That’s interesting.

Darren McKee:
That’s what made me actually like you.

Josh Schachter [Host]:
And I started paying attention.

Darren McKee:
And that’s what made me realize you had grit. And that’s what made me realize you didn’t go to college. And that’s what made me realize that you grew up in an oilfield town. And that’s like, that’s what people deeply resonate with. Yeah. Whenever you start to share your origin story over and over and over again.

Josh Schachter [Host]:
Interesting.

Darren McKee:
But you have to do it a lot because nobody’s going to remember the first one.

Josh Schachter [Host]:
Pillar 2. Let’s write pillar— let’s, let’s write the post. Yeah. So you just met with Cassie Vaughn.

Darren McKee:
Yeah.

Josh Schachter [Host]:
Regional Vice President of Monday. None of this has been rehearsed, folks. Yeah. Regional Vice President of Monday.com. She’s got a team of 100 CSMs.

Darren McKee:
Yeah.

Josh Schachter [Host]:
You tickled her curiosity with, with social selling and she wants to talk later, right?

Darren McKee:
Yeah.

Josh Schachter [Host]:
Like she knows the value in social selling. Write a post for Cassie and for others like her.

Darren McKee:
Yeah, the post would be simple in that scenario. So it’d say, picture this, you’re an RVP leading a team at monday.com and you’ve got a team of 150+ leaders. And out of those leaders, only 3 people have shared content in the last 30 days. And out of those 3 people, only 1 of them actually wrote the post themselves. And so there’s a huge bar for them to do remarkable things. And so also, if I go down a little bit further, mapping it to some competition, across the hall that’s doing it a lot better.

Josh Schachter [Host]:
There’s some FUD, there’s some fear, uncertainty, and doubt.

Darren McKee:
Yeah, and by the way, I’m just making all this stuff up about this conversation now, ’cause I haven’t wrote that post yet. But that’s how that would be. I need to make sure that I’m addressing, or I’m identifying her pain, I’m addressing her pain, and then making it feel like, oh my gosh, if I don’t do this, something’s gonna happen, right? Or it’s just talking about a new product and really diving deep in like what actually that’s gonna change in the business.

Josh Schachter [Host]:
And to be clear, like you’re not actually suggesting that people go and write a post about their version of Cassie Vaughn, right? Like you’re not like calling this person out like on LinkedIn, right? But— No. But—

Darren McKee:
This could be any company.

Josh Schachter [Host]:
It could be any, no, not her, but I’m saying like you’re not suggesting like to write about a company and call them out specifically.

Darren McKee:
No, no, no. Yeah, yeah. I wouldn’t even say the company name in that. Picture this, you’re an RVP of this at this. Right, right, right. And then, I mean, I think the other part is like, you have to be okay talking about yourself sometimes too. So I was in a room full of 140 enterprise AEs yesterday in Raleigh, and one of the people were like, well, I don’t want to talk about my accomplishments. I don’t want to talk about being that I was the number one quota attainer this month.

Darren McKee:
I don’t want to talk about like that my net revenue retention was the highest and out of all the CSMs last month. And I was like, why? And they were like, well, it feels self-serving. And I was like, well, don’t you think that VPs of product and data who these people sell to want to work with the best person. You should be talking about that. I don’t want to work with the mediocre rep. I want to work with the one that I know that’s been killing it. Yeah, right. Because I know that they’re going to take care of me.

Josh Schachter [Host]:
No, I know. But you know what? Like, it is something like there is honor in humility for sure. And it does feel like it grates against that, even though I agree with what you’re saying.

Darren McKee:
Yeah. We got to be okay telling ourselves that we’re great.

Josh Schachter [Host]:
You’re right. You’re right. It’s the whole stand in the mirror every morning and tell yourself.

Darren McKee:
But it took me a lot of coaching and to work with a lot of coaches to get to where I could actually do that freely.

Josh Schachter [Host]:
Coaches or therapists?

Darren McKee:
Coaches, therapists, pastors, everything you can think of.

Josh Schachter [Host]:
At the end of the day, they’re all kind of different labels, same thing.

Darren McKee:
Yeah. Oh, I’d get in trouble if I answer that question. But yeah, all wildly different, but a lot on the same purpose.

Josh Schachter [Host]:
Agreed. Amen to that. Yeah. Third post, personal.

Darren McKee:
Third post is personal. It’s probably where I’ve booked the most revenue. What is it? Which has nothing to do with work.

Josh Schachter [Host]:
Tell me.

Darren McKee:
So this is me talking about fishing. It’s me talking about hunting. It’s me talking about my love for old Toyota Land Cruisers. This is me talking about, you know, being with my family, traveling, whatever that may be. Not saying, you know, this is what fishing or so-and-so taught me about. LinkedIn is social selling. It’s just me being a human.

Josh Schachter [Host]:
So my post that I sent you, my draft last night that I sent you to take a look at.

Darren McKee:
Yeah, about the oranges.

Josh Schachter [Host]:
About the oranges. I was in Whole Foods and I love sumo oranges and I’m like, here’s what sumo oranges have to do with the willingness to pay. And you’re like, eh, don’t mix the two.

Darren McKee:
No, you don’t have to mix the two. You can just talk about like, wow, this is wild that this orange is priced this much. Stop.

Josh Schachter [Host]:
Done?

Darren McKee:
Done. Just people are like, whoa, this is interesting because people are so bored right now on LinkedIn. If you can make them smile, you can make them laugh, you can make them respond to something that they don’t feel like they’re actually working. Yeah, that’s, that’s, that’s huge. That’s like a big, big, big moment. And so, you know, I think that you’ve got to do that.

Josh Schachter [Host]:
Write that post. Write that post for me right now. If it doesn’t get more than 5,000 views, then I want my money back.

Darren McKee:
I will bet my life that we get 5,000.

Josh Schachter [Host]:
What’s the exact post?

Darren McKee:
Oh, the orange?

Josh Schachter [Host]:
Yeah. It’s got a decent photo too, right?

Darren McKee:
So it should be a picture of the orange with the price tag. And it’s going to be one line and said, Would you pay $3.50 for this orange? That’s it. Question mark.

Josh Schachter [Host]:
5,000 posts.

Darren McKee:
Yeah, 5,000.

Josh Schachter [Host]:
We’re shaking hands on that right now.

Darren McKee:
Yeah, it’ll go great.

Josh Schachter [Host]:
I love it.

Darren McKee:
Yeah. And it’s just going to make your prospect laugh a little bit, right?

Josh Schachter [Host]:
Like, and the listeners. I want everybody listening to go to my LinkedIn.

Darren McKee:
Yeah.

Josh Schachter [Host]:
Yeah. Dwell on that post and all the dwell time on that post.

Darren McKee:
It’s going to be fun.

Josh Schachter [Host]:
Talk about dwell time for a second.

Darren McKee:
Yeah. Dwell time. Dwell time is important. It’s something I didn’t really understand until like like, you know, probably a couple years ago. If somebody’s looking at your content—

Josh Schachter [Host]:
Oh, that’s when you like dwell on the post.

Darren McKee:
Yeah.

Josh Schachter [Host]:
Like when you’re writing it, you’re just like, oh my God, I hate writing this post. And you’re just dwelling, right?

Darren McKee:
No.

Josh Schachter [Host]:
No.

Darren McKee:
No, that’s a different dwell. But we all do that. I was telling you I was doing that this morning about my own content.

Josh Schachter [Host]:
Yeah.

Darren McKee:
Um, but dwell time is like, you know, think of a long teaching, long form content where you’re teaching somebody something and they’re looking at it and they’re analyzing it and they’re going and trying something and they’re coming back to step 2 or step 3. Then they’re looking at the photo and they’re trying to analyze like what’s happening with this photo. Maybe it’s a text message or a testimonial or a screenshot of something, people are staying on that post for a long time, which tells LinkedIn that it’s a real good post because people are learning from it, right? That’s why if you look at the analytics of each LinkedIn post now, you’ll see sends and saves there. People, LinkedIn is measuring deeply how much your content is being sent and saved because they want to make sure that you’re teaching people things. So they’re really leaning into that and it’s important. You can’t do it on every post because you just, you’ll get burned out.

Josh Schachter [Host]:
But there have been 3 posts that I’ve written in the past 3 months that have stood out from all of their posts ever. Yeah. Including like the post of like, hey, I got married or hey, update, got acquired. Like those did well, right? Like as they, I think LinkedIn probably knows their celebratory posts, whatever. But like there’s 3 posts that have like just gone way above and beyond even those. And those—

Darren McKee:
50,000.

Josh Schachter [Host]:
50,000, 40,000, and like 30,000 views. And we know that that’s vanity metrics, but it still makes me feel good.

Darren McKee:
Yeah. So important.

Josh Schachter [Host]:
Well, so each of those posts had a photo. Yeah. Had a photo that was not AI generated. Yeah. Because LinkedIn is noticing that, as do humans, right?

Darren McKee:
Yeah.

Josh Schachter [Host]:
And so you told me, we were kind of talking before the show and you’re like, the photo is helpful because it proves that It’s like the ransom photo. It proves that you actually did this. Yeah. You didn’t fake it. And those photos, I realized they all had text. Now the first one, because I was wondering for a long time why the first one did so well. It was on New Year’s Day. There was a guy who had parked his car.

Josh Schachter [Host]:
This is in The New Yorker and me coming out. I think The New Yorker always comes out, but especially now.

Darren McKee:
It’s a great city.

Josh Schachter [Host]:
It’s got its ups and downs. There was a guy who had parked his car on New Year’s Eve, and all New Year’s Eve, I didn’t go out and party. I was in bed by 10:30. And the horn was honking the entire night for like 3 hours. And it snowed that night. And I took my finger, and in the snow, I wrote on his windshield, “Your horn honked all night long.” All night long. And it just exploded. And I think I realize now it’s because people actually have to take the 2 seconds to read, zoom in, to zoom in, to pinch and read.

Darren McKee:
Yeah.

Josh Schachter [Host]:
And then the other posts that did really well that I wrote and— but you looked over them, you know, with me before we published them because you are coaching me and we are building this social selling motion at Gainsight, which I’m incredibly thrilled to be doing with you. One was a text message from a CS leader where it was just like behind the scenes of my inviting him to a CS dinner coming up. But it was like real talk.

Darren McKee:
Which is like how all of us want to be talked to, to be honest with you.

Josh Schachter [Host]:
Yeah.

Darren McKee:
Like we don’t want to be invited to something via this long chunky email.

Josh Schachter [Host]:
No, it was like, hey dude, can you make it? And he’s like, no. I was like, oh, like, are you working? I’m not going to say who it is, but I’m like, are you working? It seems like you’re working like a dog right now. And he like responded like, “Woof, woof.” That’s the relationship you want to build with your ICP.

Darren McKee:
That’s the way it should be.

Josh Schachter [Host]:
And then the other post was Chuck Ganapathy, our CEO, and he had sent me a Slack message saying like, “Hey, could this thing be vibe-coded?” And so those are three things that were very authentic. I could have doctored them, but I didn’t. And I think people know that that’s too much work for me. And This is not real. And it took reading time as well. And you were suggesting, I didn’t realize this, you suggested that they started with the photo, then they went on.

Darren McKee:
Probably went and read it after that.

Josh Schachter [Host]:
And to read it. I had never thought about that.

Darren McKee:
Yeah. Yeah. I mean, I think that’s like, it’s just interesting, right? So first it makes people read. Second, it tells people that there’s trust there and they’re like, okay. And then they’re going to come back to the next post because they like that one, right?

Josh Schachter [Host]:
Yeah.

Darren McKee:
And so it’s just like you’re building that trust engine and I think we’ve just like lost a lot of that.

Josh Schachter [Host]:
And again, this matters professionally for go-to-market teams, both 100% sales and post-sales.

Darren McKee:
Yeah, I was just talking in the room beside of this where— and I won’t say the, the CMO of a very large company that was mentioning this to me, but the conversation over the last 6 months for their AEs and CS interviews was like, hey, how, how agentic are you? Like, What— tell me some AI things that you do day in and day out to make sure that, like, you’re a fit here.

Josh Schachter [Host]:
Yeah.

Darren McKee:
And while that’s important, it has pivoted now to can you host 12 dinners with 12 people in 12 cities in the next 12 months? And if you can’t do that, we don’t want you. I love that because it’s important to like, yes, we need to be AI forward. Like, we all get it. But like, can you actually host a dinner? Or not.

Josh Schachter [Host]:
Can you build a fucking relationship?

Darren McKee:
100%. Otherwise, just don’t. Why bother? Yeah.

Josh Schachter [Host]:
Yeah.

Darren McKee:
I’ll get some pushback on that one.

Josh Schachter [Host]:
Should people be incentivized financially for posting their company? So actually, let me sit back one second.

Darren McKee:
Opening a can of worms?

Josh Schachter [Host]:
Opening a can. Before I open the can, I already opened it and you can’t put it back in. But you need folks to take time to do this, right? And I think you’re a believer in blocking out your calendar, having that dedicated half hour or whatever it is. So explain a little bit about that. And then if we are going to have sellers and other people that are taking a concerted effort amount of their time, then like, yeah, should they be compensated for that?

Darren McKee:
Yeah. Um, I’ll answer the first one, first question first. Um, yes, I’m an avid fan of time blocking. Um, but I think this is a leader’s responsibility to make sure that this is happening, um, inside of the space. Um, you’re, if you’re in a C-suite role, like you need to be at the forefront of this content and social selling motion. Um, uh, and once you start to do that, there will be a lot more psychological safety in the team to be able to be like, oh, I can freely do this.

Josh Schachter [Host]:
Um, so, so CEO probably does somebody, somebody in my position, but like, that’s what’s going to get you like CFO.

Darren McKee:
100%. Yeah. 100%. They’re the ones that are actually seeing the business. Chief product officer, head of engineering. Um, those are people that are deeply like, quite frankly, our buyers really want to read their stuff more than they want to read our stuff.

Josh Schachter [Host]:
We have a new CFO. He just joined, Paul Shepherd. Seems like a great guy. I haven’t met him in person. Just joined, right? He comes from a banking background. He’s British, very kind gentleman. I’m going to assume maybe a little bit British reserved. I’ve never been on his LinkedIn.

Josh Schachter [Host]:
I’m going to imagine that he has not posted. Maybe he posts once a year, but you’re saying that the CFO, Paul, if you’re listening, of Gainsight should be posting on LinkedIn.

Darren McKee:
100%. 100%. And whoever’s building the products and whoever’s building the HR engine, right? They should all be active.

Josh Schachter [Host]:
Interesting.

Darren McKee:
Yeah.

Josh Schachter [Host]:
Okay. And then how should they be compensated?

Darren McKee:
Compensation’s interesting. You obviously have C-suite VP levels that, that’s probably just should be part of their role, to be quite frank, sharing content about, about the business, about what they’re doing. But you’ve got other people that you might have, you know, associate in finance, you might have, you know, somebody that’s in ops or, a software engineer that’s sharing a piece of content about what they’re building at Gainsight, and all of a sudden they look up and 25,000 impressions on their post, 240 likes and 92 comments, and 14 of those people are prospects, and the SDR goes and looks at that and books 4 meetings, and then the AE closes 2 of those calls, and then that AE makes $75,000.

Josh Schachter [Host]:
Yeah.

Darren McKee:
Well, that’s not fair.

Josh Schachter [Host]:
Right.

Darren McKee:
Right? We need to split some of that percentage upon the original person. That’s why lead source and tracking is so important around this.

Josh Schachter [Host]:
Around this.

Darren McKee:
Like, where did that lead come from? Did it come from the software engineer’s LinkedIn post? Well, we should probably compensate that person because they’re doing something outside of their job. Now it’s up to every company to figure out like what that percentage looks like, but like something is better than nothing. I don’t even care if it’s a spiff, something, right? Or recognition, right? And then what happens? And that software engineer makes $7,500. And then they go post again and then they get 4 more leads. It just starts to snowball and starts to trickle.

Josh Schachter [Host]:
What kind of systems do you need to have set up for this to work? What kind of like plumbing do you need with Salesforce and being able to track it versus just like, okay, everybody go post and go comment?

Darren McKee:
Yeah, I mean, there’s a bunch of things that’s, that’s a problem if you want me to be quite frank, which is why I built 531 Social, which is, which is my tool. But I mean, at the end of the day, you need lead source data in Salesforce. You need to make sure that like the team is empowered to understand like how to actually like input some of these things, they need to understand like what those next step actions are within social selling and the sequences that happen with all of this stuff. And so, yeah, there’s not, there’s not a really good system yet. We’re trying to build it. But other than that, like we just got to get going. And at the, at the end of every 2 months, look back, pull a report and you’ll see a bunch of deals coming through from, from social.

Josh Schachter [Host]:
Well, I wasn’t trying to lead you into 5-3-1 because you didn’t pay enough for the appearance. But let’s talk about 5-3-1. What is 5-3-1?

Darren McKee:
Yeah. So I took everything I’ve ever spoke, talked, typed, I’ve recorded in my life and built it into a model. So you’ve got Darren McKee in your pocket, which is terrifying, but insanely awesome. So you can ask any question about LinkedIn, social selling, sales, or anything that I’ve ever typed. We don’t pull from any external sources in that. So it’s just my words that are in there, which is beautiful. And then on the other side of the platform, we talk about account-based enrichment and its sequences for social selling. So all of your accounts can be tagged and built in there and enriched.

Darren McKee:
And you have next steps for everything you need to do from a social selling perspective in LinkedIn. And so just makes the job really easy for a seller to know like, oh crap, I didn’t do this thing, you know, yesterday. I need to make sure I—

Josh Schachter [Host]:
Like, what are the types of things that it helps to organize?

Darren McKee:
Yeah, did you respond to all your comments yesterday on your LinkedIn post? Did you reach out and send a video message to the, you know, CS leader at so-and-so company? Did you share a moments that matter post, right? Did you share an ICP-focused post? There’s just all of these things that quite frankly changed my life Now you have access to know if you run this playbook, you’ll be wildly successful.

Josh Schachter [Host]:
Lastly, talk about LinkedIn Sales Navigator, how you have to use that effectively.

Darren McKee:
Oh man, it’s the greatest tool on the planet. The filters there are beautiful. Able to see of my prospects who’s posted content, who’s new in role, who used to work at my past companies. I mean, it’s just a vast amount of information.

Josh Schachter [Host]:
But what you do is you basically have a list of folks that are your, that’s your ABM model. This is your prospects or the folks that you want to keep keep close with.

Darren McKee:
Yeah.

Josh Schachter [Host]:
You, you filter or you import that.

Darren McKee:
Yep.

Josh Schachter [Host]:
And then you use it kind of as your LinkedIn feed to see who—

Darren McKee:
In SalesNav.

Josh Schachter [Host]:
In SalesNav.

Darren McKee:
So I focus on a methodology called 5-3-1. I’m not talking about the company anymore, but 5-3-1 is 5 companies every single day, 3 people inside of said company, and then 1 LinkedIn action to those 3 people inside of those 5 companies. So find my buyers, look at their content, engage with their content, send them a connection request, send them a video DM, build relationship, close deals. 15 engagements every single day. Like, if you can’t do that, you shouldn’t be selling or in a CS seat.

Josh Schachter [Host]:
Yeah. I mean, those are big words. Yeah, but it’s worked out for you.

Darren McKee:
Yeah, it’s worked out for me.

Josh Schachter [Host]:
Working out for me. We’re doing well.

Darren McKee:
It’s been fun.

Josh Schachter [Host]:
Yeah. Cool. Well, listen, I can’t wait for more of this motion being brought to Gainsight. So far, so good. And it’s been a pleasure working with you.

Darren McKee:
Yeah. Thanks for having me.

Josh Schachter [Host]:
Yeah. Thanks for being on the show.

Darren McKee:
Cheers!