← The Digital Executive
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- [00:00]
A
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- [00:56]
B
Foreign. Welcome to Coruscant Technologies, home of the Digital Executive Podcast. Do you work in emerging tech? Working on something innovative? Maybe an entrepreneur? Apply to be a guest at www.corazon.com brand welcome to the Digital Executive. Today's guest is Colin Coggins. Colin Coggins is a Wall Street Journal bestselling author and the General Manager at Chegg Skills. He is also an adjunct professor at the University of Southern California where he has taught Sales Mindset for Entrepreneurs for the last 18 semesters. A course focused on the durable human skills that matter most in the age of AI. Colin has a deep experience as a technology executive, recognized for his unique and proven approach to operationalizing growth by cultivating both durable and technical skills across entire organizations and embedding a commercial mindset cross functionally. He has held senior leadership roles at several high growth technology companies including Bitium Mobile Roadie and more recently as Chief Commercial Officer at Fabric and Senior Vice President GM at Chegg. Well, good afternoon Colin. Welcome to the show.
- [02:14]
A
Thank you. I'm glad to be here. Thanks for having me.
- [02:16]
B
Absolutely my friend. I appreciate it, really do because I know jumping through different calendars and folks in between two time zones LA to Kansas City. I appreciate you brother. So let's jump in. Colin, you've built a career as a commercial leader, author and speaker. What roles at companies like Bitium and now Chegg Skills. What experience has shaped your journey and philosophy around sales and leadership?
- [02:42]
A
Yeah, it's a great question. I think probably one of the biggest things that have shaped me is I never viewed selling as persuasion. This idea of who salespeople are manipulative, smarmy, yucky, Pushy is true no matter who you ask. That is what people think of when they hear the word salesperson. But then if you ask someone who's the greatest salesperson, they know the top two answers are Dr. Martin Luther King Jr. And Steve Jobs. And then it's people's parents or people's children or people's partners. So there's always been this massive incongruence for me between who people think great sellers are and who the greatest sellers on the planet are. And a lot of them don't even have sales in their title. Most of them are entrepreneurs, leaders in their own right, engineers. So I just, I think early on in my career I realized that the greatest sellers on the planet typically don't always have sales in their title and they're the antithesis of who people think they are. And so in my early days in tech startups, I just realized that they're the best leaders. They were not the slickest people in the room, and they were the most self aware people in the room. So when you think about my career as a chief Commercial officer or Chief Revenue officer, I've had the opportunity to really work in these high growth environments where you can't change your world, your company's world, the world in general, if you don't know how to move people. And so when you're scaling companies, especially now at Chegg Skills, during moments of true transformation, you learn very quickly that leadership is less about having all the answers and more about really just helping people how to navigate change. You know, when I was writing that book, I think that was a, that was a philosophy that just held true. It was a realization that the greatest salespeople and the greatest leaders are the same people. And they don't technically sell, except there's a lot of agency around them. Like people are buying in. Like my class that I teach at usc, a third of that class shows up every single week because they want to learn how to sell themselves. Like they want people to want to work for them, not have to work for them. And a third of the class shows up every week because they want to learn how to sell ideas, right? They want to be able to garner investment. They want people to be excited about the projects that they're pushing through. And then obviously there's people that want to just sell traditional products and services. But I think I've made a career out of understanding that a commercial environment is an extension of every department. And if people understand that that is not a yucky word and that anything important in life Is worth fighting for, worth moving people for. You just gotta find out what you have Vader for. I think for me one thing that the book really taught me during the writing process was if you can find the right team composition where people get to wake up every morning and do what they love doing versus what they have to do. Ray Lewis, the old football players have this great quote. He said they pay me for what I do Monday to Saturday, but Sundays are free, Sundays are my pleasure. It's like okay, well there you go, right? Like find out what people's Sunday moments are like what do they love so much that they'd be solving that problem or solving that problem on Sunday morning. And that was. That is a privilege position that I am in right now. In check skills. Like I have got so many amazing people that wake up every day and get to create access for learners that historically were forgotten about, underrepresented and, and did not have access. And so being able to be able to work in that environment, especially coming through the ranks the way that I did, I'm really proud of how me and this entire organization define sales.
- [06:26]
B
Thank you. I appreciate that. I really do love the backstory. And you talked about you never really viewed selling as a persuasion but and you mentioned you highlight, I should say you highlighted a couple of the. You think the greatest salespeople ever and they didn't have sales in their title is Martin Luther King Jr. And Steve Jobs. I thought that was interesting. And great leaders, great salespeople are most self aware and they're most self aware in that. The room that of the people that they are interacting with. I thought that was interesting. But the analogy with the football, especially professional athletes that get paid for that, you're absolutely right. Something that they totally love and enjoy, they could do it for free. And that really that Sunday football game. So I appreciate that. At the end of the day the message is understand people and how to navigate change. And that's what great leaders do. So thank you for sharing. And Colin, you're known for an unconventional approach to sales that blurs the line between sales and life. What does that mean and how did you develop that perspective?
- [07:28]
A
Yeah, and you got the heavy questions. I like it. It's like my. A person would read the unsold mindset or go into a class or you know, work at a company that I'm leading. And I think that like you start to see like relatively quickly that authenticity is really important in getting stuff done, like real work, like to be able to, you know, most, most early Career professionals think that their job is to be perfect, to, to know all the answers. And you get later on in your career, you realize that like, nobody wants to be stuck in a room with a know it all. And the reason why deals get turned down all the time in PE rooms or in VC rooms is because it seems too good to be true. People like buying from people like themselves. And a lot of us are not selling ideas ourselves or someone else's ideas to people that look like us. Believe in what we believe in, talk like we talk. So, like, what's the common denominator? It's imperfection. Right? That's what it is. Like, we're both imperfect. And when someone realizes that the, the goal is not to be perfect. Like, the goal is for someone to have the ability to see themselves in you. And the only way you can do that is to get to the common denominator which, you know, you both have in common, which is imperfection. Like, it sounds weird, but the, the greatest leaders, entrepreneurs, sellers, individual contributors that I've ever met in my entire career, like, they are the ones that are f in you at showing you that they are imperfect. And so if you, if you think about it from that lens.
- [09:01]
B
Yeah.
- [09:02]
A
I, you, some, you. Are we talking about selling authentically or are we talking about living authentically? Like, if, if we are, if we're all always selling ourselves, selling our ideas or selling other people's ideas. Is this a conversation about selling authentically or living authentically? My CEO, he's got this great line that I have stolen and repurposed and most people love it, except for my wife, which is, and he doesn't believe in work, life, balance. It's just called life. And I love that because I think it really resonates with the answer to my long winded answer to your question. I think the other thing, when you think about the idea of authenticity and when you blur sales in life and what does that mean? You have to think about curiosity. Yeah, I think that in life you give yourself permission to ask questions that you actually want to know the answers to. And those are unique to your perspective and where you sit in the world. But for some reason in business, people don't. People ask leading questions. People ask questions to make themselves look smart. People ask questions that they already know the answers to. And you're stripping away the agency from the people that you're asking those questions. You're, you're stripping away the gifts that you know what it looks like to ask somebody a question that they've never heard before. And in real time, watch them ideate for the first time on an answer to a question they never heard before. Like that is a gift. If you never see them again, that is their, like that is their answer. You didn't sell them on anything. Like they bought it. And you look at any given organization, most of us, you know, when we get into work mode, we are extracting value by asking questions. Tell me, give me, show me where, when, how, how much. But there is a rare breed of people in the enterprise, in, at the university level, just in life, that have figured out a way to add value by asking questions. But that's only because they are asking questions that most people never cared to know the answers to. But because you do, because of your authentic, unique position on this planet, you want to know the answers to something that most people don't. And this is where it gets really interesting in the age of AI because everyone touts this, you know, to sound bite that curiosity is the most important skill in the age of AI. It's not that it's not true, it's just always been the most important skill. Go all the way back to like, I mean, way beyond our generation or our parents generation. The most successful people have always been the people that wanted to know answers to questions that most people weren't ask ask it. So we have this ability now with AI to leverage a piece of technology to ask it questions that you really want to know the answers to from your unique perspective. And that can change, that can change your career trajectory in a heartbeat, but only if, only if that line is blurred and you are in the workforce as your true self and not pretending to be the person that you think your colleagues or your partners or your clients or your boss or your direct reports want you to be. That's a long winded way of saying being a human is really important in an enterprise and it's really important in learning. And is that life? Is that sales? Is that business? I think the answer is yes in general. And maybe the fact that the line is blurred, that is the point. I don't even know if having an answer to this is the right thing to do. Like maybe, maybe the point is to be in the best part of the movie, right? To chase this, this line and toe it between life and in traditional business and, and frame it in a word. I mean I have seen so many people get credit for being resourceful as opposed to get credit for having answers. And so anyways, great question. I don't know if I have the Right answer. But I certainly have a perspective.
- [13:06]
B
Absolutely. And you have your answer. And you talked about that authenticity, your uniqueness. So I liked when you said, when a person realized they are not perfect, with all these imperfections, there's no selling. That kind of goes by the wayside. And I liked how you explained how you can blur that line between sales and life. Again, authenticity is key to sales and building trust with those you are engaging with. And you certainly add value by asking questions. So thank you for sharing. And Colin, at cheggskills, you're focused on education and workforce readiness. How does your approach to sales and communication translate into helping individuals build better careers?
- [13:44]
A
Yeah, well, being the GM of chegg skills as a, call it sales professor or subject matter expert in sales, really gave me the ability to run the business the way that I thought would be successful, which was that sales wasn't a yucky word and everyone felt like they were an extension of this commercial mindset and that it wasn't, you know, a yucky word. I think one of the biggest problems in education and workforce development is that I think we often focus way too much on information and not on transformation. And that's what matters. Like, knowledge alone isn't changing somebody's life, like the application of knowledge does, right? It's not the piece of paper that gets you the job, it's the proof of skill acquisition that gets you the job. Or at least in 2026 that's the case. So knowledge alone just isn't changing, isn't changing the game. So at checking skill, like, a lot of our focus is on helping people really bridge the gap between learning something and actually using it in the real world. And I think that's where communication becomes incredibly important. Whether you're interviewing for a job, pitching an idea, leading a team, navigating AI in a workplace, like, there's ultimately a question, right, that you're trying to answer. It's just like, how do I create value for other people? That's sales. Like, not in the stereotypical sense, but I think we've already understood, like, what my definition is compared to that in the human sense, that's sales. Like, people who thrive in their careers are usually the people who can clearly communicate their value. Like the ones that can adapt quickly, build relationships that continue to learn. Like, who's whose job? Whose job is it to own skilling and learning? Like, is it a continuous learning? Like, is it the. Is it the ins. The higher ed institution? Is it the workplace where you work? Is it. Is it you? So when you when you start to think about like answering those questions. I think a huge part of workforce readiness today is helping people understand that they're capable of reinvention, especially how quickly technology changes. We're talking about in a generation of AI, we are talking about a piece of technology that at least for the first time since I've been alive, a piece of technology that benefits lesser skilled people, like just as much if not maybe more than advanced skilled people. That's incredible. Like technology has created a massive digital divide which we all know about and we know who falls into that gap. And we have this choice that we get to make now with AI, which is like it could be the first time where it bridges the gap. And so that's really important for us to create access for people. Like remove role biases on who gets to have access to equitable stilling. Everyone. If everyone was learning it, then it wouldn't be. I was talking to a VC a couple days ago and he was like, look, it's either going to be exactly what you think, Colin, or the top 1% is going to be 100% richer and there's going to be a wider gap. And in order to prevent the latter, we have to remove the biases on who gets to leverage AI and who doesn't. And when you think about, we talked about curiosity being so important. Like this is why I'm so passionate about skills based education. Like the world is changing too quickly for static career identities. People have to have the ability to continuously evolve. These are not technical prowess conversations. My team has heard me say this story before, but it's one of my favorite ones. I have a 6 year old and I have a 10 year old and I've been living in the middle of AI for quite a while now. It might my 10 year old, at the time he was 8. I'm coming home every night and talking about AI and blah, blah, blah. And my, and he goes, daddy, I want to be good at AI when I grow up. Like, tell me how to be good at AI. And it's like the sweetest question to ask. And my response was, let's ask AI baby. So we open up the laptop clear as day, it's like, hey, what skills are necessary to thrive in the age of AI? And my kid's not a stem kid. Like he's just like his daddy. Like he is much more of a liberal arts Persona, for lack of a better word. And you, you look at the answer that AI gave you on what skills are most important to thrive in this generation of AI and 8 out of 10 of those skills were not technical skills. They were durable skills. They were curiosity, metacognition, communication, durability. The, the idea to be able to, to, to, to be resilient. The. These are things that are like, so, like self awareness. These are things that are so hard to teach someone. But yet if, if, if a lot of the hard skills, if a lot of the technical skills are being automated, like are these even soft skills anymore? Do soft skills even exist anymore? So let's check skills. Like, we are very intentional. Like there is not a program that you are going to take where there is not an intentional convergence of durable skills and technical skills. Because those durable skills, the shelf life of those durable skills are a lot longer than the technical skills. And it's one thing to be able to keep up with the pace of technology. Like it's a whole nother thing to be able to leverage it. So I just, I think that a huge part of the workforce readiness today is just making sure that people understand like what it really means to evolve and stay ahead or at least keep up with the pace of innovation. This is not just a technical conversation anymore and that should be really exciting for people.
- [19:30]
B
Thank you. Really appreciate that. Just there's a lot there you unpack but kind of highlight some things I thought was important. Love that your role, the champion, the subject matter expert of sales at Chegg Skills you talked about society nowadays is more focused on education than transformation and the importance of leveraging the education, not just focusing on that knowledge. And then again, how well can you explain that value that you can create for people? That's at the end of the day, that's how you're going to resonate with somebody. And then you did dive into this thing called AI we talk about all the time on the podcast, should be a tool for everybody, equitably lowering the entry barrier for everyone. And that resonated. So thank you. And Colin, last question of the day. As we look ahead to the future, how do you see the role of sales evolving in an AI driven world? And what skills will be essential for professionals to succeed in the future?
- [20:24]
A
Yeah, I think we kind of touched that on the last one. It's. I think AI is going to dramatically change how work gets done, but it's also going to increase the value of human skills. You know, we were just talking about these deep human skills. Like a lot of the transactional work is going to be automated. Information itself is becoming commoditized if it's not already so you having all the answers isn't special anymore because everyone has all the answers. But human judgment, trust, creativity, eq, the ability to tell stories, to adapt, like all of a sudden, like these skills are super valuable. And if you think about some of the college students that I get to teach that are having such a hard time, you know, getting jobs when they graduate, you know, they're all saying the same thing. It's because there's a three year experience requirements and they were just in college for four years, so how would they have three year experience for an entry level job? By definition, right? You should be able to get it right out of the gate. And it's because these skills are so tough to teach that the enterprise is saying, well, you're not learning it in college. And I don't have the time to teach you this because I need you to have these human skills. I can teach you the ones and zeros, the X's and O's, but I, I don't have the time to teach you how to be self aware or competitive, right? Or, or have a high eq. And so like I don't, I don't think sales disappears. I think bad sellers disappear, regardless of how you define sales. But, but I mean AI is pretty cool because it gives everybody the ability to be a creator, right? Like you're going to see so many entrepreneurs and I love that. But that also means you're going to see a lack of differentiation in the market. You're, you're not, you're going to see a lack of moats if, if everything is so democratized. So how are you going to differentiate your, your product from the next one? When everyone can create the product in a really short period of time, it's going to be selling. But like if you look at the table of contents of my book, the table of contents of my book as it relates to selling looks a lot more like the table of contents for an emotional intelligence book. Like, I had a great, great conversation with Microsoft about my book and it was because they wanted their engineers to read it. And I thought that was so funny because why would engineers read a sales mindset book? And it wasn't until like the, one of the leads in the engineering corps said, look at your table of contents. These are the skills that are most necessary to thrive in the age of AI. Like, engineers are looking a lot more like product managers. What do you think a product manager looks a lot more like? Like the best salesperson in the room. So the future belongs to people who can really combine technical fluency with human connection. The professionals who are succeeding, they're going to understand AI. They're going to understand how to use it and know how to work alongside it and how much value they add to AI. But they're also going to know how to think critically, communicate clearly, ask better questions, like build trust. It's. I talk a lot about vigor. It's like one of my favorite words. It's the idea that the willingness to engage uncertainty with a certain amount of energy, even before you feel really ready, that becomes so important when defining the skills of the future. So I think AI is really just accelerating change so quickly that no one's going to be able to feel like they're fully prepared for it. But when you think about the shelf life of the most important skills that matter in the age of AI, there's a lot of value that humans get to add in this generation of AI. And the people who win won't necessarily be the people that know the most. Like they're going to be the people that are willing to adapt the quickest, that are more curious than others, that keep moving. And honestly, I think that's a really hopeful future. You know, like the fact that fundamental human qualities are going to be some of the most important skills in this age of artificial intelligence. That gives me hope, not fear.
- [24:35]
B
Thank you. Really appreciate your insights here. Obviously, as you mentioned, AI not only will change that productivity landscape, but you believe will improve those deep human skills such as EQ communication, storytelling, et cetera. Sales will, will still be here and you're in your again, your prediction, bad sellers may disappear, but sales will still be here in this AI future. I liked your story about you talking with Microsoft in your book and they wanted them to their engineers to read your sales book because out of that they can actually learn human connection, better communication and building trust. And I thought that was insightful, so I appreciate that. And Colin, it was such a pleasure having you on today and I look forward to speaking with you real soon.
- [25:16]
A
Likewise. Brian, this was awesome. Appreciate you having me.
- [25:19]
B
Bye for now.