Navigating Career Transitions and the Future of Sales in the Age of AI

Join Molly Baker, and a seasoned sales leader turned independent consultant, as they explore the dynamic world of sales and AI. In this episode, they discuss the evolving role of AI in sales and marketing, the importance of nurturing authentic professional relationships, and how the freedom and challenges of growth have shaped her career. Whether you’re navigating a career transition or looking to optimize your sales strategies in the age of AI, this conversation offers valuable insights for anyone looking to thrive in today’s fast-paced business environment.

Molly: So without revealing yourself and who you are, what do you have going on professionally today? What are you thinking about? What are you up to? 

KL: Like many people, I'm spending a lot of time thinking about AI. Although, interestingly, I'm exploring AI from a security standpoint. I've been working with a company that's building an AI immune system, which is to think about how are we protecting our data and are we training our models on safe data. So we're thinking a lot about that and then on the flip side, I'm thinking a lot about human connection and what does that mean? I think that's gonna continue to be important regardless of how AI develops. And so how are we bringing smart, interesting people together in events to share ideas to challenge one another, and to learn new things, and to be better able to communicate with one another. 

Molly: So you have the AI world and then the complete opposite of that, which is relationship building and connectivity. You should work in complement to one another. I agree. 

KL: I don't think they're mutually exclusive. I agree. 

Molly: So what are you really good at? Brag about yourself.

KL: Well, I will say communication is one of those things that typically falls on the list. But something I'm really proud about being known for recently is sales. I'm really good at sales. And I know for a lot of people, the first thing that comes to mind when you say sales is a car dealer. 

There's a lot of negative association with that. But I find more so now than than ever, it's my mission to help people understand that you can have a service mindset when you're selling. And the way I like to operate with clients is to say, we're shoulder to shoulder and we're gonna go over here to like achieve that objective that you're seeking. And we're gonna educate one another and learn from one another and offer solutions. If it's a great partnership, fantastic,

if not, I'd rather move on to something different. I actually spend time training sales teams and working with different leaders on improving those skills and changing the mindset around sales being something that's not great versus a around sales being something that's not great versus a really lucrative career path.I kinda wish I had known about, corporate sales and B2B sales. You know, I've been a media seller for much of my career after being a marketer on the brand side, and I almost wish I knew about that earlier on.

Molly: So how did you get good at sales? 

KL:Practice. A lot of it comes back to practice, but I think it's more about, to your point, can you paint a vision of what the goal is and what you really wanna achieve and then inspire people to wanna come along and do that? And if you have the products and services that are able to help people solve their problems and to move on and achieve this amazing goal, that's really what sales is. I think sales is a lot of problem solving in education. 

Molly: I agree.I think used to be intimidated by it, to be honest, like, because because I think of the stereotypes that come along with it. It's like, I'm not a salesperson. I don't wanna identify as a salesperson. But then once I formed my own style of selling and definition of selling, honestly, then the game changed.

KL: I love that you talk about leadership style, whether it's your sales style, if you do things that are natural to you. I would lead teams and my approach to a given client would be very different than 3 different individuals who might work with me. But if you lean into your own strengths, that's what's gonna feel authentic. That's what's gonna earn the trust of the person that you're collaborating with of the business that you're partnering with. You move forward and, you know, I am on a mission, as I said, to change the perspective on the word sales. But when you think about it, I I know a lot of people that work in finance. Private equity, venture capital, etc. There's not a person that I know that doesn't go back to their investment committee and sell the idea of whatever company they wanna invest in. Right? Like there's a CEO of every major corporation has to be convincing shareholders of what they're doing and set that vision for the organization. So the more you can inspire people to do that, the more successful you'll be at sales. You realize that it manifests in so many ways. I mean, who was I just listening to the other day? Some YouTube video. But they were talking about how Steve Jobs was not an exceptional technologist. He was an exceptional marketer and salesperson. And without him, the adoption of all of this technology might be very different.

Molly: How do you help people define their leadership style today? In this fast paced, ever changing world, how do you work with people on that? 

KL: Well, I encourage people to keep learning. I don't think leadership is something that is one and done. I think the more you can keep learning and stay curious, I think that's the most important thing. Because the reality is, particularly now, it's impossible to stay on top of every single trend or every single thing that could work. Staying curious in that and then when it comes to people's individual styles, I would say part of that is about how do you communicate. Like, how do you communicate and connect with people and what's gonna feel authentic to you? I operate with with a model of radical candor. Where if you care personally, you have to be willing to challenge directly. I try to demonstrate ways that I care about people and seek their feedback, but also I'm willing to say the thing because we're in service of a bigger goal. For some other people, they tend to be a little bit more gentle in some ways. For some people, they tend to be a little bit more aggressive in other ways. But what I found is that people can wrap their head around whatever style really works if you demonstrate that you care for the people that you're working with and you're honest about your communication style for and not trying to be time management, are you not? Right.

Molly: Like You're not trying to be something you're not. Once you're pretending, it all falls apart.

KL: If you're figuring it out, you could say, listen, I'm a new leader, I'm figuring it out, but I've really liked how so and so does it, so I'm gonna try this and do that for a period of time. And does that work or not? Then get feedback. I mean, I think that is actually an underrated thing is that particularly when you're a leader, you have to find ways to creatively ask for feedback over and over again because the higher you go, the more likely it is that people are have some fear around telling truth to power. To really get the real feedback, you need some peers. I would often try to have at least 1 or 2 people on my team who I knew would like tell The real-real or maybe some cross functional team members who are not directly accountable to you. Unless you seek it, you won't actually get it. But if you say, listen, I'd really like to know what am and where what are my blind spots? Or I'm working on this. Where have you seen this go well or not? Or I would like to make sure I'm good at this, can you point out examples or pay attention for the next next month and tell me when you've seen me do this well or to really fall short on this? 

Molly: I love that. Do people give you that feedback when you ask?

KL:Yeah. But you as I found, the the the higher you get, you have to ask more and be more creative and find more people to do it. But, yes, I think that people if you really demonstrate that you're genuine about it and you really, put together an action plan and tell people what you're gonna do about it, if you just take it, what is their incentive to keep giving you feedback? But if you so one of the practices I would try to do was solicit it from my team, let people deliver it anonymously, and then meet 1 on 1 with anybody who is willing and sit and just listen for 15 minutes and take notes. Digest it all, and then the next week, put together a plan and send it out. Adjust it all, and then the next week, put together a plan and send it out and said, hey here's what I'm gonna be working on. And then let's check-in another couple months and let me know how it did on those things. 

Molly: Interesting. How do you balance asking for the right amount of feedback? 

KL: I think you make a lot of great points about people will unload if you give them the opportunity, and is that really appropriate? I think if you were to say, what are some things that you've noticed or maybe you've received some guidance from a performance review from a superior of yours? Maybe you've heard some things from your team members. What is something that you genuinely care about wanting to get better on or that you've heard, this could be a potential derailer. Like, this is actually causing some problems. In some way, shape, or form. I think if you give some context and structure to here's 1 or 2 things that I'm trying to work on, that'll help.

Molly: How do you show people on your team that you care about them?

KL: I think this comes down to being authentic. If you pretend or don't wanna give too many tips and tricks because I don't think it would feel right. You have to choose the thing. For example, some people say, oh, always say good morning and walk around the office and be super friendly. It's not that I don't love being friendly in an office, but I'm not a morning person. Most people who worked on my teams knew that I was gonna get there in just enough time to be prepared for where my first meeting was. Maybe I'd be able to utter a, hey, takes a little bit of time to to kick in, but that doesn't mean I didn't care about them. I would just be honest and say, hey, I'm not a morning person. Celebrating successes, I think taking the time to get to know people and frankly, going back to what I said at the outset about new managers, taking the time to understand the personal goals of the members of your team and the people that you work with. Then remembering that and taking action on that behalf. That's really what I think is is about how you demonstrate that you care about people. It's not the the little things aren’t great. You know? Bring the cupcakes to the office and sending sending thank you notes. I did make a practice of sending thank you notes. That's something that's organic to me. So I would do that. But I've found that more often than not, this is people's work lives and if you help them understand where they're gonna go forward on their path in their work life and that you acknowledge what's also going on in their personal life as much as they wanna share it. That's the key. If you're trying to fake it too much, people will see through that. 

Molly: What relationship has been most impactful on you in your career?

KL: I saw you had this question and honestly the first thing that came to mind is my best friend, which may be a little counterintuitive. My best friend actually passed away 10 years ago from ovarian cancer. But, you know, we were tremendously close and had met in school many years prior. But the reason I say it had the most impact on my work life is because there was a fundamental shift for me, first after she got diagnosed with cancer because I became somebody who showed up and was able to care for her in in a number of different ways. And through that process I started to think about this idea of I wanted nothing unsaid. Like, what are the things we could, would, like, say to one another? And even though the outlook was totally different than we had thought it would have been, she would still have a great life for for what she had. So just that changed my whole mindset and how I operate with my family and friends but really as a leader too. It really makes me wanna value time differently. I prioritize things differently because none of us are really guaranteed any time. We never know and so I try to be cognizant of that to say, is this report that we're delivering very important for this one time? Yes. But if somebody has something going on in their personal life in the grand scheme of things, where does this all fit? How do I communicate more thoughtfully with kindness and caring and do a better job showing up for people that may be going through different challenges in their life? And think about what my priorities really are as I'm moving up and through different organizations. I know it's made a difference for me in my career.

Molly: That's amazing. I mean, talk about perspective shift and going through something like that does make you realize, to your point, everyone has things going on in their personal lives. Whether they choose to share or not, everyone has challenges, and, also, time is not guaranteed, and how do we best make the most of it? Is this when you started to prioritize radical candor? 

KL: No. That had been going on forever. Get to get blunt all the time, and then Kim Scott came out with radical candor. I said, great, I'm gonna use this language because that's what I really intended. But no, it's this idea of nothing unsaid is important. I think, too, to make sure that we're recognizing and celebrating this. Like, do we say the positive things to the folks on our team. Like, when our other colleagues and cross functional team members. I think sometimes we think about, the people we work with as just our immediate colleagues at whatever organization we're currently with, but that all the folks that you work with as partners, if they are providing services to your company or if you're a salesperson and you're providing services to the others, sometimes you spend more time with those folks than you do with the people sitting in the office with you. 

Molly: So tell us who you are. What do you do? The great reveal. 

KL: I'm Kristen Leoni. I'm and sales leader and I'm really focused on helping companies unlock, revenue growth. So I work as an independent consultant these days after a long career at many big brands and Google for the last 6 years. It's been really exciting to get to partner with leadership teams to help them understand how to work with AI in this new ecosystem which has really shifted in the last 12 to 18 months. Then also, as I had mentioned before, with sellers and sales teams and sort of train them and to help improve their skills. 

Molly: How long have you been independent for? 

KL: I think 4 or 5 months now. It's been very fresh.

Molly: What helped you make that decision? Like how did you know it was the right time? 

KL: I think it was it's always a combination of things. I didn't see a path forward for me in the organization where I was at the time so I was feeling that I wasn't moving at a pace that was intriguing for me. I thought, wait I can do some of what I love inside of this company outside and on my own and be able to control the pace a little bit differently. Then I've always found that the idea of ownership is really critical. My dad has this saying where he says, you know, in your career you can get paid for what you do. You can get paid for what you know. You can get paid for what you own. And many careers start out with you get paid for what you do. You work an hourly job. Right? I worked at Blockbuster Videos, you know, dating myself in high school. You're just getting paid for for being there. You get paid for what you know. That's probably a lot of a lot of us do. A lot of my career has been the knowledge that you bring to the table and the different roles that you that you have. But if you get paid for what you own, whether it's the stock portfolio that you own, whether it's real estate that you own or another entity, you can basically do whatever you want if that money's making money. And so how do you get to that that point? 

Molly: So what does an average day look like right now? 

KL: As you might imagine it varies but a lot of times it's a lot of conversations with people. So as a salesperson you might imagine I am often reaching out to an extended network of people and I like that. I'm an extroverted person, I get energy from talking to other folks. So it's exploring opportunities and it's making sure that folks are aware of the services that I'm able to offer. Then it's a little bit of, development, whether it's curriculum development for some of my trainings, content development, or actually working on specific projects. Then I'm also trying to really be more disciplined about blocking time for upping my game with different AI skills, playing with different tools, and experimenting and things like that. 

Molly: What's been the most surprising thing or the biggest thing you've learned since leaving Google and going out on your own? 

KL: It's nice to have the freedom and the control.That maybe it's that you really have to find the right path for you. If you have the inkling that this could be something that you wanna do, go for it because there's often a way back. If you really were to play out the worst case scenario, could you get another job either at your prior company where you've demonstrated for a certain period of time that you've delivered value or at one of many others. With this new experience that you will have had being out on your own, will you better refine why do I like working entrepreneurially or why do I miss the structure and the frameworks of a bigger organization? I think that's because I have a lot of conversations with former colleagues and I'm like, oh, that's great. You're not stuck in this planning cycle or doing end of year budgets, this and that. But for them, some of what I do, they would hate to do, to reach out to people blind and say, hey do you need something? Maybe you don't. But here's how I think I might be able to help you solve a problem, whether or not it's now or down the line. 

Molly: I totally relate to that. When I left my corporate job and went out on my own, I freelanced for a year before I had started indie, but it was just me for over 14 months. You do tell yourself those things of, like, hey, I'm gonna go try this, and if it doesn't work out, I'll go get another job. Like, I know I'm hireable. I know I could go back to where I was or go find something different. I'd probably find something different, but there's only benefit there's only ways for me to benefit from this experience. I'll learn something about myself, and you absolutely do, and about what the market looks like and the space that you're in looks like because it's a totally different perspective than operating inside a large entity. But I agree too that, you know, people will say well, one, there's always this misnomer, I feel like, especially when you go out on your own and it's just you to start, you just didn't really wanna work anymore. And people are like, that's so nice, oh you probably you have such chill days. It's actually not that chill, at all, but I think there's that. And I think some people love the structure because when you go out on your own, there's no structure, and you have to make the structure. And there are systems that even to this day, now 6 years in to having Indie, I'm like, wow I didn't even know how much went into, you know, 401ks.And like the management of that and the administration behind that. No clue. There's a lot of systems that you take for granted when you're in a formal corporate structure. That if you don't get some energy out of building, then you shouldn't do it because it takes a lot of work.

KL: I love that you called out that misconception that you're just hanging out and that you're not figuring out how revenue is gonna come in the door, which is your income now, 100%. 

Molly: I mean, I saw someone at a wedding, someone I went to college without a wedding this summer, and she was like, hey congrats, It seems like Indie has turned into more than just a side hustle for you lately. And I'm like, it was never a side hustle. I've been doing this for 6 years. Like, what do you mean? It's it's no longer a side hustle. But I think it's just a totally, people don't know if they've never been through that experience. 

KL: It makes me think of a story that somebody who came to visit Google told one time they're a content creator on YouTube and they talked about this idea of cringe mountain. Shocked about the fact that had a great again, had a great job, was doing things really well, but had this concept and it was around personal finance and education around personal finance and decided to start a YouTube channel and all of like friends, family, kind of coworkers were a little cringey. During that time because you don't know what you're do you're learning. You'd have to set up a lot of systems. And they would all make some kind of comments. But at a certain point, you get to the top and then all of a sudden everybody's like, hey that looks great. What are you doing? Hey, I remember when we, you know, did x y z and can you help me with this? And so she said, you know, the thing to do is just remember, just keep stepping up Cringe Mount. Just keep taking those steps. Because at some point, you're gonna hit that inflection point and everybody else is gonna change their mind, and you've been on that journey.

Molly: Where do you find yourself drifting to now as you're building out your own practice?

KL: I would say that there's always been a digital and, like, technology through line to what I've done. Even in the days when I was brand manager on Nature Valley granola bars, we were building website, doing Digital marketing at that time and so I would say that that's a through line. And then for me, I think it's more about the function. The sales and marketing function and developing expertise in that area and knowing, how can I understand any given product and then be able to effectively communicate about that and sell that in to somebody? Because I will say, I mean, tech and media has been something that's been for the last certainly 15 years of my career really major and then once you've been in healthcare, if you have any kind of personal interest in it. I've worked at places like Pfizer and WebMD and even IBM had a big healthcare practice. Once you know the ins and outs of that, it's a small world In many ways of the the people in that industry that move around. I think that can be really helpful and I guess I'll I'll say that to reinforce a point in case it's helpful is that whether you're working on your own or you're working in a big company, it's really useful to make sure you're taking time to pick your head up and maintain a network. Well, it's the folks that you've worked with or people that you meet at events. And I think there's much like sales, there can be different conceptions about what networking means. What I found most useful is to say I'm curious about people. I'm interested in people and I wanna get to know and nurture relationships with those folks and that has made a massive difference in my career over the years, keeping in touch with folks that I've worked with, seeking folks out that I'm encountering at different events, and not doing it in a fake way. You you may go to something and not connect with anybody and that's okay. You don't have to force yourself to do that. But stay curious. If you're reading things, if you're engaging with content online, if something clicks with you, that's when you go down that path and maybe pursue a connection or a relationship there. And then don't forget about finding ways to nurture it again in a meaningful way. There's not a magic number of touch points. There's people that since I've left and started my own thing that I hadn't talked to in maybe 10 years. The pandemic contributed to some of that where we might have encountered one another. But I reached out, I had a thoughtful reason why reconnecting might be helpful for both of us, and they were incredibly generous with their time and then recommendations. So just because a connection may go dormant for a little while, if you, you know, have other, it's okay.

Molly: And I think most people, especially if you're looking to learn from them or pick their brain on something or even just see how they're doing, want to talk. People want to connect. I think the hurdle is most people just get nervous about reaching out. But I have found in most cases, people from all different points in my career, if I reach out, they're like, yeah, let's do a Google Meet, let's go grab coffee, let's have a drink. Rarely do people say no if we've known each other in a past life in some way, shape, or form. 

KL: How does it feel when you get to help somebody? A lot of people it feels good to help people. And so, you know, if you're on the other side, think about if you can be somewhat clear on how somebody might be able to be helpful or what you're, you know, doing or how you're gonna be engaging with their time, that's the way to do it. 

Molly: I agree. I mean, that has been one of my biggest learnings. Even though I didn't have a super long career before I started Indie, I didn't realize that I was, like, naturally networking a lot throughout my career because I just like it. I like having coffee with people. That's my, like, that's my modality. Let's grab a coffee. I just wanna catch up. I wanna hear about their job. And when I left my corporate job and started, I was shocked at the people that came out of the woodwork to offer support, offer referrals, and offer advice. It was amazing. And the nurturing, I think you just have to find, to your point, the way that feels best for you. I it can look so different, I think, for everyone. How do you feel like your time at Google prepared you for what you're doing now? 

KL: One of the great things at Google was getting to operate at scale. I mean, what is a scale that is that size? There are very few companies that operate at that scale. So it was an incredible learning experience and to really understand what that means. I think that that's prepared me and given me some flexibility in the types of other clients that I can work with because I understand what it means to operate at scale. The other things that were actually very helpful were the learning that I was able to accumulate at Google. Google would bring in so many speakers, have so many different programs, so many different, you know, ways to engage and connect on things, and some of that has been incredibly helpful, in how I'm moving forward. Molly: So if people are coming to you today and they wanna work with you, what what are they asking for? Are they asking for, like, AI integration into their business? Are they asking for strategy work? What are they typically asking for?

KL: So it's probably two or three things. The most straightforward thing is sometimes they're asking for sales trainings. They're saying, hey, we're getting our sales force together or, hey can you work with some of our senior sellers to level up? We're having more conversations with if they're media sellers, they're having conversations with a chief marketing officer or a CFO and there's some strategies to do that and sometimes even working with senior sellers, just having them practice or try new things, it's not that we're reinventing the wheel. It's just everybody gets better. And we're all so overwhelmed, I think, and time crunched now that taking a little bit of time out to refocus reminds even the most experienced sellers that, hey, this is fun. So one of that is that. The other thing would be around sales strategies. So working as like a fractional chief revenue officer and helping organizations understand how should we organize the team? Are we going to market in a better way here? How's the partnership with product marketing? And then the last would be where AI plays more of a role which is to say for any company that's at a transition point or that hasn't looked at their investments in the platforms, Meta, Google, Amazon, etc, all of the algorithms have shifted materially and the game has changed. There's a lot of companies that have built, their organizations on the back of search. Lead gen, whether you look at the back of search or the back of social, lead gen is a model that is changing now. The real estate is changing when you look at the results coming from gen AI models and the consumer behavior is starting to shift as well. So if you are doing the same thing that you were doing 12 to 18 months ago, you're not gonna be able to get the same results. The data that these systems need to intake is different as well. So sometimes it's it's consulting with folks to help them understand that and to help them think about what could be different.

Molly: And is that with their media teams internally or with their agency partners?

KL: A lot of times it'll be with internal teams, like with the chief marketing officer or going in through the, executive suite. But, I mean, I'm open to it. It sort of depends on the opportunity. Because sometimes it could be even a short term. Hey, let me help you map out some questions to ask with your agency or with your organization. 

Molly: What's one thing you wish you had known earlier in your career? 

KL: I think it's about sales. I think it's about the career of sales and the fact that it's lucrative. For anybody that is undaunted by the idea of engaging with people, I do think there's a little bit of a gene of you have to have that curiosity or that desire to be a little bit more extroverted and get the energy from problem solving with other folks. But if you have that, don't just think that sales might not be for you. Explore if there's an opportunity there.