(21) How the CMO Role is Changing w/ ex-CMO of Calendly Jessica Gilmartin - YouTube https://www.youtube.com/watch?v=uKesC6rCu7k

Transcript: (00:00) How do you see the CMO role changing? And obviously here the level of company where you were operationally involved in Kalan Lee Assan are large B2B tech. >> I don't think anybody ever got into marketing so they could write a bunch of technical garbage that is just used for LLMs. (00:18) If you just are like a CRO that has a bunch of directors or senior directors of marketing reporting to you, honestly, I don't think it's it's going to work very well. You always make bad hires. The only mistake you can make is keeping the bad hires. having people that maybe were good at the time but are not where you need to be now. >> Where do you think we are on the path of overvaluing or undervaluing AI? Are people still underestimating what you can do or are we already looking for nails to just use it on? Where are we on that journey? All right, before we dive in, you're (00:52) listening to the Executive Brand Podcast with me, your host Falmayer. Each week I sit down with top B2B CEOs, executive and founders to break down their playbooks. If you've not yet, it would really help if you subscribe or follow the show because it helps us get on better guests and create better content for you guys. All right, let's dive in. (01:13) All right, I'm here with Jessica Gil Martin. Uh she is an adviser to CMOs and CEOs of large software companies on all things marketing and go to market. There she leverages her experience from previous roles which among others include CMO and CRO at Kalantley, head of revenue marketing at Asana and head of product marketing at Google. (01:33) She is also an LP at stage to capital, a board member at text expander. And the reason why I wanted to have you on Jessica is because I think through your work you have somewhat of a bird's eye view on kind of what's happening in go to market and marketing in 2025 and beyond. And so wanted to dive into those things. (01:53) So thank you for coming to the show. >> Yeah, thanks for having me. >> Anything to be amended or corrected there in the intro? >> Nope. >> No, sounds good. Cool. Now, first I wanted to ask you on the CRO CMO thing because obviously you have held both roles. Um there's an older debate around, you know, marketing and sales should sit underneath a CRO. (02:18) Some people say CRO is just a fancy new title for head of sales. I also saw Bane Capital recently put out a thing um about the CRO being rewritten. I'm just curious on your take how it worked at Calendarly um on those two kind of roles and how they should interact or not. >> Yeah, I would say that it's pretty difficult to do both and it's pretty difficult to be good at both. (02:43) And the only reason that I was able to do it is because I had a really good head of sales underneath me that understood the day-to-day and was in the day-to-day. Um, also I uh many years ago I had built sales from scratch at a previous startup. And so I deeply understood the sales function. (03:02) You know, I was actually the first salesperson. I hired salespeople. I figured out our outbound. And so I think if you don't have the experience of either being a marketer or being a salesperson, I think it's pretty hard to do both. And I work I actually advise a lot of marketing leaders um like kind of BP level that report directly to a CRO without a VP of marketing. (03:26) I would say that that's not super successful. Uh so I think you can make it successful as long as you have very senior leaders who deeply understand the function and can provide that level of support and leadership. If if you just are like a CRO that has a bunch of directors or senior directors of marketing reporting to you, honestly, I don't think it's it's going to work very well. (03:49) And kind of the flip side too, like if you're a marketing leader, trying to run sales without a strong sales leader, it's I I just don't think it's going to work very well. But even in this scenario where you have someone who deeply understands sales and deeply understands marketing, which obviously that is very rare, are you not just spread too thinly at that point trying to manage all of that? I mean, my philosophy has always been if you hire really strong senior leaders, then you really shouldn't be involved in the day-to-day. And so, that's actually (04:19) something that I coach all of my uh all of the people that I work with because what I have found with first-time CMOs and CRO, the thing that they tend to do is they tend to hire very junior people. I think a lot of the reason is that they they almost feel insecure. They don't feel like they have the right to hire somebody very senior. (04:40) And my philosophy has always been like a seale person should never be involved in the nitty-gritty. You know, I should not be uh doing pipeline review calls. I shouldn't be looking at every single deal. I should be extremely aware of what's happening. I should be grilling, you know, my VPs. But if I'm, you know, figuring out what our pipeline is on the marketing side, if I'm directly involved in all of the details, if I'm reviewing like email copy, then something has pretty massively failed because the the company needs me as a sea level person (05:14) to be doing much different types of things and I should be able to rely on very senior VP levels to do the day-to-day. Um, and my job is to create the circumstances in which they can all be very successful. Now if if Bane Capital wrote about how the CRO role is changing, how do you see the CMO role changing? And obviously here I'm talking about the the level of company where you were operationally involved in Kalan Lee Assan or large B2B tech. (05:45) >> I think it's changing everywhere. I think it's changing for very small companies. I think it's changing for very big companies. Um the thing that I have found most interesting over the past couple of years is um and I'm going to completely contradict myself from what I just said is a a couple of years ago when companies were looking for CMOs uh it doesn't matter how big or small the companies were they were looking for people that had $500 million a billion dollar plus experience like like literally companies that were $10 (06:16) million were thinking I've got to I've got to hire a CMO that can scale I' got hire a CRO that can scale. Um, and that was and that was what they focused on. And those CMOs and CRO did not have operational experience. They actually didn't know how to create a more innovative environment. They didn't understand the technology well enough. (06:37) They didn't understand the details well enough. And now I'm seeing a complete reversal of that which is even at really large companies like three you know relatively large 300 400 500 million those CEOs are looking for uh CMOs from smaller companies and cos from smaller companies because they're finding that they're the ones that are more innovative they of course it's all about AI so every single question is about what AI tools do you know do you personally know you know what AI tools would you put in what are some of the (07:08) new things that uh are happening in marketing, in sales that you personally understand and can make sure you're implementing because what everybody's seeing is that the the world is totally changing and it is and the people that are successful are the ones that are thinking about the new ways of doing things and if you are just like a CMO CRO with 20 years of experience at large companies, you're just like typically not bringing that level of innovation and that's what CEOs are seeing. (07:36) So they're willing to take a risk on some of these earlier stage sea level executives because they're they're thinking I want to replace somebody who knows how to scale teams with somebody that knows how to build high performing organizations with as few people as possible. >> And do you where do you think we are on the path of overvaluing or o undervaluing AI? Obviously all the talk is about AI. (08:05) everything everyone should be using AI everyone you know needs to use AI obviously AI is very very powerful and you can do a lot of things and we're very early on that journey but where we are right now are people still underestimating what you can do or are we already looking like AI is the hammer and we're looking for nails to just use it on where are we on that journey >> I can see where you think we are and I kind of agree with you which is I think we are overvaluing uh AI right now. (08:37) So I I personally believe that there's endless possibilities. So I I think that in 5 to 10 years we will have replaced most of our current day-to-day with AI. I'm super excited about it. Right now um I think that there's a huge amount of talk about AI and I spend so much time like a huge amount of my time speaking with everybody that I can all and I live in Silicon Valley. (09:03) I have access to lots of really innovative people across the board and I am seeing this massive difference in the hype and the expectations and the requirements versus the reality. And what I'm seeing and because I I sit on boards, I interact with a lot of boards is that you have a lot of board members that are telling their CEOs, telling the executive teams, you have to use AI more. (09:27) Like that is the mandate. You have to do it. And then if you ask the board members, they actually typically don't have any specific use cases. Like you know, you literally will say to them, and we've done it, can you connect me with other people in your portfolio that are doing something really innovative and interesting? And they typically don't have it, but they just it's just this hype has become so massive that everybody assumes that everybody else is doing something interesting. (09:53) And so your mandate is you've got to do something really interesting. Now, of course, if you look at, you know, the AI coding tools, I mean, there's really innovative things there. And of course, there are pockets where there's really interesting things that you can do with AI, but right now, I see it as an enabler. (10:09) I see it as a way to become to have your team be say 10 to 20% more efficient, particularly in the marketing and sales side. It is not a replacement for people at this point. It is not a game, it's not gamechanging for marketing sales at this point. uh but I have pretty strong confidence it will be. (10:28) And so I think that you know my job as a marketer and everybody's job as as a marketer as a salesperson is to be understanding what's happening now and to be looking out constantly for what's going to happen because I think this will not be a revolution. I think this will be an evolution over time where all of a sudden in 5 years you look around and if you haven't been following the path the whole way you're really going to be way behind everybody else. (10:54) >> What are the most impactful AI use cases you've seen that have been deployed at such some amount of scale? >> So for sure you know clay is something that people talk about all the time and I I have seen it really be successful. I would say some of the really interesting work that I've seen is around data enrichment. (11:16) You know, so right now one of the most challenging things that marketers and sales have is what leads do you work? You know, you have just endless amounts of u of opportunities. You have endless amounts of leads, uh customers, potential accounts. How do you figure out how to go after them? How do you figure out how to prioritize them? That's where I've seen AI be quite successful uh in just really helping understand if you who who in your existing customer base is most like the people that you're trying to go after um and really helping you come up with an (11:46) ideal customer profile that you should target. So I'd say that that's been a really strong use case. The second one that is if I've seen some of my clients do this very successfully. I'd say most people are not doing it. And this is where I think it can be really gamechanging is on the product marketing side. (12:04) And so that is really helping do deep research on competitors. Uh really understanding what's your ICP your versus um you know what your competitors have. How do you think about you really doing deep research? looking at the LLMs almost as a customer profile, like basically a customer panel, >> synthetic like user audience. Yeah. >> Yeah. (12:31) And so, you know, I I now go to to ChachiBT all the time when I'm thinking about um campaigns, when I'm thinking about product launches. Uh and it just helps you to literally take things that would have taken weeks and you can do them in the matter of a couple of hours. uh you also one thing that that I've done really successfully with my clients is you know throwing your website into an LLM and asking it to give a very fact-based uh assessment of your website and you know so oftentimes you have a lot of debates and discussions that are unproductive like I don't like the (13:06) website well why and there's not really a great reason but you can actually sort of have a framework to say does this website you know does it have social proof um does it align with the uh with the way that our customers think about you know and you could come up with a set of criteria that are very objective and so there's just so many different ways that you can use LLM for product marketing that really accelerate the process and and obviously everyone talks about content so I won't bother to do that but that's that's clearly a huge (13:35) use case as well >> and if that that you mentioned how the CMO role is changing which kind of I would summarize as companies have shifted from trying to get the the CMO from the bigger company um who has seen the big scale rather someone from the small scrappy startup who has their hands dirty inside of Chad GPD and Gemini and all those tools and claw uh and clay and can implement some of those workflows in their slightly bigger companies. (14:07) How's the orc chart changing? How are you seeing for the most forwardthinking companies, how is the marketing orc chart changing? So I I personally think that um every marketing sales organization is going to have and we've already seen it you know they're going to have much more technical skills you know so before it was and and I would say that I haven't seen it massively change in terms of you still need designers you still need content people you still need product marketers you know you still need campaigns growth marketing it's just the (14:43) everybody is expected to have a level of technical able knowledge. That used to not be the case. You know, you used to have a writer and a writer would just write. Now, a writer has to be able to use AI tools. They have to. That's just a given. Um, and I think the most important thing and the most and and I think actually the most valuable thing which didn't exist before is that the marketers have to engage with each other and communicate and talk to each other and plan with each other in a way that didn't exist before. Uh and so what used (15:13) to happen um in most organizations is you'd have content people that are just creating content and throwing it out there without a distribution plan. And you'd have the campaigns and the growth marketers who were creating, you know, uh paid strategies, organic strategies without thinking about our product launches, without thinking about the content strategy. (15:35) And now everybody has to work together because the reality is is budgets are smaller, headcount is smaller. So you have to make every single thing that you do work 10 times harder. So there's just so and I think the layer the underpinning of that is technology and operations. H because what you have every single person on the marketing team has to understand is who is your customer? Where are they? How are you finding them? Uh how are you enabling sales to do outbound? So what is the what's the way the mechanism by which you can support outbound through (16:10) marketing efforts? ABM is you know almost everybody is doing ABM regardless of the size of the company and that is absolutely critical uh to have good technology, good data, good operations and so I I would say everything to me is about how do you have really good intelligence? How do you have really good technology? How do you have the collaboration between marketing and between marketing and sales? >> Does that mean by consequence if there needs to be more collaboration that the idea of having functional heads of head (16:45) of paid and your head of content marketing and your head of brand and your head of product marketing? Do those still make sense or should there be a more cross disciplinary role that can work across those things? You know, it's a great question. I have never been able to figure out a structure that doesn't have that. Um, and I would love to. (17:10) I don't think it exists. And and I've experimented with moving people around and breaking down organizations and ultimately I always end up having a VP of brand and a VP of of demand genen. And what I have tried to do though is create um project man you know so I have always have project managers that sit across and basically enforce that I always have shared OKRs and shared goals that force teams to collaborate. (17:36) Uh and so I think you uh and then of course analytics. So you have you have the the people that are sitting there and making sure that the content team is aware of their impact or not. Right? you you're you're giving people the information so they can make better decisions and understand how they can influence the because ultimately this is all about revenue. (18:00) Uh and I think that that's a really critical part of it which is if you have a content team that sits divorced from the the understanding of their business results then they have no incentive to work with the demand genen team. But if you say, "Hey content team, your goal is to hit a certain amount of revenue. (18:18) Your goal is to drive a certain amount of of awareness." Um, and you give them the analytics and the information, then they have no choice but to be more collaborative with the rest of the organization. >> How that's how I've always kind of solved it. >> How do you do that? Because I think I've seen you also previously talk about attribution and that attribution is broken and flawed and imperfect and all those things. (18:40) >> Yeah. How how do you Yeah, >> you do your best. It's it is absolutely broken. It's incredibly difficult. This is another area that I'm really passionate about. I spend so much time trying to understand the latest tools, technologies, talking to people. Uh and the reality is is that you you're just you're you're getting to to 70 to I think you're best case getting to 70 to 80% accuracy. (19:04) And this is one of those kind of like 8020 rules, which is, you know, we know it's not going to be perfect, but let's at least have something and let's at least have directionally correct around where we believe there's we can make the most impact uh and then work from there. >> Now, on the kind of skill sets and and the team constellation, I've heard Tom Wentworth talk about that he believes there's essentially almost only two skill sets for a marketer. (19:34) there is AI nativeness like understanding how to it's almost like a technical engineering skill and then there's taste and I think he he defined marketing output as AI skill times taste squared so that taste has a much bigger impact >> um any thoughts on that do you agree disagree is taste more or less important now >> um I mean I think That's probably a little bit of an oversimplification of what a marketer needs. (20:07) Uh, but I I love I love the idea that there's still an arch to marketing because I believe that's really important. And one thing that I spend a lot of my time talking to my clients about and I think a lot about is, you know, and and AI slop is right the thing that people keep talking about is the the last thing that all of us as marketers want to put out in the world is just a bunch of garbage. (20:27) And I hear a lot about people saying, "I'm not writing anymore for humans. I'm writing for LLMs." And that's to me is a very sad world to live in where we're just writing for I mean then it literally just becomes this circular thing where where we're we're just basically putting out content that for the LLMs to then spit out that goes back into the algorithm and that's just not kind of a world that I want to live in. (20:47) That's not I don't think anybody ever got into marketing so they could write a bunch of technical garbage that is just used for LLMs. Uh and so I think there is still opportunities and needs for people to create interesting, innovative, creative um campaigns. But I think also the most important thing is is still deeply understanding your customer, deeply understanding who they are and creating something that is appealing to them and different. And that's still an art. (21:17) you you you can't just throw that into an LLM and you know have it come back with a tagline and have it come back with all of your campaigns. I think AI is an enabler and it's a supporter of creativity, but ultimately I think the best marketers are still people that start with the first principles of who are our customers um and what how are we different, how are we unique, and how do we make sure that comes across in interesting ways. (21:44) And everybody that I work with, you know, if you just ask an LLM to come up with your marketing plan, it's just literally by definition going to give you the same marketing plan as everybody else in your industry. And so there's still so much opportunity to think about how are we creating something that is unique and different when we show up at an event. (22:01) You know, what's the fun and unique way we're going to stand out? uh if we hold our own events, if we uh our emails, our website, uh you know, when we do reporting, and I think that there's still so much opportunity to educate, and that still requires human beings, and I think that I would hate for us to lose that. >> I mean, it's probably an overused example, but Ram's recent campaign where they had Kevin from the office, the actor of Kevin from the office in a glass box in the middle of Manhattan do expense reports for eight days. uh for (22:34) eight hours. I think you would have needed to prompt chat GPT for quite a while for it to spit out that idea. And then obviously the idea is not the bottleneck. It's actually a marketing team and a leader who has the courage and boldness to say yes, we're going to do that and actually exe execute it. Um >> yeah, and and I you know living in Silicon Valley I am could not be more bombarded with marketing messages, you know, and if any and if you live off 101, you see all the billboards. (23:01) Uh and we my husband and I were laughing. We were driving back from San Francisco and uh we were like how many billboards have AI in them and 100% of them did. Uh and so you know you and most of them didn't say anything and so having but every once in a while there's a really unique interesting billboard there's a really unique campaign and I always just really applaud someone who takes a different approach and and what I a lot of the companies that I work with are challenger brands and I always encourage them to be incredibly bold to you know (23:34) really push the needle on your messaging because if you have the same messaging as the company that's 10 times your size, you're you're never going to be successful. So, what's the thing that you can aggressively go after? What's the thing that you can hold your hat on and just be bold and be really brave? And people did that against us all the time at Calendarly. (23:55) I mean, literally, you know, because we were we were of course the market leader and there were tons of these small scheduling solutions and they would literally have like Countly sucks in their URL. I mean that would like literally be their URL and everything would be about against Calanly and we didn't like it. But if you're competing against the clear market leader, you can't just have a boring reiteration of the same features. (24:19) You've got to really be bold and brave. >> Yeah. I had Udilagore Aximo going on and he his thing is best practices are boring practices because by definition everyone >> does them. You said um earlier that everyone does ABM and it's kind of table stakes. You have to do it. I mean I see a debate of that on LinkedIn. (24:39) Is everyone doing ABM though? I think there's a lot of different definitions and some companies would like to think that they're doing ABM just because they have an account list. Uh but they're not actually prioritizing anyone. They're not narrowing in on anything. They're not really personalizing or customizing their campaigns. (24:58) What do you think is the right way to do ABM? um that actually works. >> Yeah. I mean, I I'm definitely not going to say what the right way to do it is because I agree with you. I think there's it it wildly depends on the type of company that you are. So, I talk to companies who they say we've got a hundred companies in the world that we sell to and like that's clearly going to be a very different type of ABM than, you know, we've got tens of thousands or hundreds of thousands of companies. (25:26) is our ACV is really small, but we know exactly who our ICP is and we have a very clear message. And so to me, the the spectrum could be among that. So, it could be you've got this incredibly targeted small list and you're aggressively going after them versus I think it's I think it's absolutely fair to say that if you've got an account list of hundreds of thousands, but you are, you know, really thoughtful about the way that I think about it is being really thoughtful about who you are selling and marketing to. (25:58) So for and I I think the to me the key is around the collaboration between marketing and sales because it's really hard to do outbound right now. It's really hard to prioritize inbound. Uh and so the way that I think about it and what we did at Cali which I thought was very successful was we would really understand hey who is the who are the groups of customers that we really want to go after? Um so a particular industry and we would kind of say hey this quarter we're going after this industry um this type of customer. Let's narrow (26:30) down and really have a good sense of whether it's um the size of the company, whether it's the types other types of tools that they use, whether it's competitors that they're using and let's have a really targeted outbound marketing and sales approach to them. And so we would do lots around uh display ads, other types of ads. (26:52) We would use intent signals to understand who's already in the market. We would feed that to sales so they could do outbound. Um so I think it's just being a lot smarter about who you're going after and making sure that uh both teams are working together. Um and just a example where that I think worked really really well was at a company called Honor and we had very small target. (27:15) So every quarter we would go after a group of about 75 to 100 companies and it would be geographically based. So, we would actually have salespeople fly in to the region, go doortodoor, dropping off postcards and flyers and introducing themselves, and then we would follow up with mark targeted marketing to them. (27:35) and we would invite them to a uh a lunch with a really interesting guest speaker and almost I mean I I would say that without fail we would get you know three to five million in revenue um just from that campaign every single quarter and so that's a I think that that's an extreme example but you can do it and I think it's that kind of relationship between sales and marketing that's so powerful >> I'm curious for at honor when you had that 75 to 100 target account list per quarter. How many how many existed that (28:10) you could theoretically sell to? Like tens of thousands, 500 in total? Like what slice of a pie was this 100 accounts? >> Uh so these were probably I mean it was probably um you know 5% of the market. Uh and so we would we we would do a huge amount of research on which were the right companies to go after and our sales people would do that research. (28:33) And so I think that that to me is a huge and now they did it manually and now this is where I think using AI tools, using some of these better intent tools, these better um uh technical tools can really help you. So I think that that to me is the key is really deeply understanding to start with who are the types of companies that you want to go after. (28:53) Uh, I everything starts with having a really good list and having really good buyin and agreement between sales and marketing that yes, you're both going after this and you're kind of doing everything that you can to try to get these in the door. Uh, where I've seen ABM fail is when marketing has a list, sales has a list, and you're actually not talking to each other. (29:13) And like, weirdly that happens all the time. Yeah, I know this is a very nittygritty question, but I'm curious if you have an opinion on like where that target account list should live because I agree with you that one key feature of it is that it should be a you know this is the one and not one team has this Excel spreadsheet and then someone else has this HubSpot list that they export and send to this but they already updated it last week. (29:39) There should be one source of truth. >> Yeah. >> Do you have an opinion on where that should live? Everything must live in in your CRM. >> Okay. So, Salesforce, HubSpot, whatever you're using. >> Yes, it has to it has to live in CRM. That what I have marketing is always willing to go into a CRM. Sales is never willing to go out of a CRM. >> So, >> that's funny. Yeah. (30:02) I think what you said like 5% of the accounts was the that quarter's target. I think that just requires courage that a lot of companies I just don't see. I mean, we work with smaller companies than what you're advising, I would say 3 to 20 million in revenue, and when I ask for a target account list, I would say 80% of the time the answer is we don't have one. (30:22) >> Y >> and so that is crazy to me. >> Um >> it's very I mean, nobody wants to nobody likes trade-offs. That's that's the number one thing that I've discovered in my life is everybody wants to do everything. And that's why PLG is so appealing because when you say who do you sell to, they say everybody and it sounds great. (30:43) Um, and then you don't have to have an account list and you don't have to um on your website you don't have to make hard decisions about your copy because you sell to everybody and it goes on and on and on about tradeoffs. But the reality is is as you get bigger and you could you could do that when you're very small. The reality is as you get bigger, you have to have trade-offs. You have to have an ICP. (31:01) You have to have you have to say very clearly I am selling to this person. I am not selling to this person. You have to have account list. You you just you cannot um be successful especially right now. You you cannot be successful unless you make hard trade-offs, unless you prioritize, unless you aggressively go after a certain group of people. (31:19) >> Yeah. Before I ask my next question, how would you describe who you currently advising mostly if you had to bucket it a little bit? >> It's it's all it's B2B. Uh it's all B2B tech and um I I it's everywhere from pre-revenue. So, I'm working with someone who is a founder that is figuring out his product and I'm kind of helping on the go to market side all the way up to um probably my biggest client right now is 100 million in revenue. (31:46) And typically who I work with are first-time CMOs, uh founders who just want somebody who has seen a lot of things, made a lot of mistakes, and what I try to do is just help them not make those same mistakes. What advice do you find yourself most often repeating to your clients? H >> so much. (32:09) I find myself repeating a lot of things. Um I think probably the the biggest thing is around uh people and the number one thing is is you know you always make bad hires and the the only mistake you can make is keeping the bad hires. um and or or not even making bad hires. It's having people that maybe were good at the time but are not uh are not where you need to be now. (32:34) And so having sort of the courage and the discipline to really take a hard look at your team and recognizing that maybe someone isn't the right fit and when you bring the right fit on board, your life gets 10 times a hundred times easier. So that's probably the number one thing that that I talk about is around headcount people uh leadership. (33:00) How do you lead people? Communication. Um that's something that I find shocking is how hard it is for people to proactively communicate. Uh and so I find that a lot of the issues between boards, CEOs, and CMOs, a lot of the issues stems from a lack of trust because of a lack of communication. And so a lot of what I do is really help them think about you know what almost like a therapist like what are the issues underlying issues why is that the case how can you communicate more effectively and then I actually spend a lot of time helping them think (33:34) through how do you articulate the tradeoffs so you know if if a CEO is asking a CMO to do XYZ uh maybe you know why can the CMO do X and Y but not Z and if you did XYZ what what are the trade-offs to to not being able to do other things? And that's it's just a huge perpetual issue that I see. >> Is there a correlation between that and companies being more remote and fewer water cooler conversations? >> I don't think so because I you're not really having like at the at the sea level, you're not having a lot of water (34:10) cooler conversations anyway. Um you know, you're just in meetings 10 hours a day. Uh, I I think what um I think it's just a perpetual and I've seen this for forever and I think it's just the CMOs um and I I've particularly seen this with CMOs is they tend to get very defensive and uh and I and I I it's a chicken and egg kind of thing which is there's a lot of really unreasonable CEOs and I have worked for many of them so I can say this that expect everything you know they want you to do everything. (34:46) They they give you less budget, they give you less headcount, and they expect you to do 10 times more or they don't understand the function, but they still demand all these things that you would never demand of a technical person because they understand the technical side. >> And so the CMOs get really disheartened and they get really discouraged and they get really frustrated and defensive and so they stop sharing as much. (35:07) And so it just becomes this really unhelpful cycle where the CEO and the CMO their relationship breaks down because the CEO has like doesn't understand the function well enough, makes a lot of demands, the CMO gets frustrated, stops sharing, they lose uh they lose that relationship and I I think this is one of the main reasons that CMOs last you know 18 months on average they just it's it's because of this breakdown in trust and communication. (35:34) What do you wish more CEOs knew or understood about how marketing works? >> I wish they understood that. And this is actually something that I share with every So I I do these conversations with CEOs probably once a week where I um help them understand how to hire a CMO. So I walk through the different paths to being a CMO and what you give up and what you and again it's all about trade-offs. (35:58) Everything in this world about trade-offs. >> Is that easy to expand on? like in a nutshell what are the different paths? >> Yes. Yeah. So, so there's three there tends to be three paths to to being a CMO. One is through brands. Um that is very rare to have a brand uh a brand CMO in a B2B. That typically is a TOC, but those are people that are the the Nikes, the you know of the world. (36:21) They're very creative. They are big visionary big picture thinkers. Um then you've got product marketing and you have demand genen. Those are the three different types. And I'd say from in B2B you typically have 50% product marketing, 50% coming from demand genen. It's pretty equally split. Um you're going to have very very different types of CMOs if you have a head of product marketing versus head of demand genen. (36:44) And this is the thing that I tell a CEO at least once a week, which is if you you are never going to find a unicorn that is great at both. And this is where CEOs get so frustrated. Um, and I and I I'm not a technical person, so I try to liken it to technical things, but if someone's on the on this call and is like, "That's totally wrong, Jessica. (37:03) I apologize." But to me, it's like asking an, you know, a back-end engineer why you can't code mobile apps, right? Or like asking a data scientist why you can't do why you you can't be a a UX designer. They and and nobody would expect that, but they expect a marketer to be all of these things. You you cannot be super technical and deeply understand demand genen and growth and be super strategic and understand deeply understand customers and messaging like you just maybe there's 10 people in the world like that but you CEO are probably (37:40) not going to find that person and so that's why they get frustrated because they want one thing but they don't understand it and they hire another. And so a lot of what I do is I spend time with CEOs to say what are your problems now like at this moment and for the next year what are your problems and some will say you know I don't have an issue with pipeline my biggest problem is I feel like our messaging is weak I feel like we have really interesting differentiation that we're not getting out in the market you're like okay hire (38:08) a product marketer um or someone else another CEO will say I feel really comfortable about a differentiation I'm like I love to get into the messaging I love the writing part of it. Um I just need to drive pipeline and so their frustration happens when they hire a product marketer and but they that person doesn't know demand genen and so understanding who you're getting uh and what you're hiring for is really important. (38:34) The other thing that I tell CEOs all the time and this is the other big mistake I see >> is they hire for they're they're 10 million in revenue and they're hiring for 100 million in revenue and they're like well we're we're definitely going to be there in two years. It's like, well, maybe you will, maybe you won't, but you're probably going to, based upon the market, you're probably going to hire another CMO in two years. (38:57) So, don't hire somebody, and that's okay. That's not a problem. It's not it's not an issue. Don't hire somebody for hundred million if you're 10 million. Hire a $10 million CMO that can get you to 30 or 40 million. So, hire someone you need right now that can build a team right now. Uh, and then worry about the scaling part in two years. (39:17) If there's three paths to CMO, brand, product marketing, and demand genen, and 50% is demand genen, and 50% is product marketing, and a large part of marketing is to be different and stand out. Does that mean that the brand native, the CMO who has a brand background is massively undervalued and appreciated in B2B? And it's one way how you could have an edge. (39:42) I have I have seen I have not seen brand CMOs be successful in B2B. So a lot of what I do is I I come in after CMOs have been fired and I kind of help out for a few months. So that's a lot of my practice and >> many of the people that have come in that have not been successful or brand because the reality is is that they don't they typically don't understand either the differentiation enough or the numbers enough and that typically is what is most important to a CEO. (40:18) So CEOs get very frustrated when they're asking these questions about the about the the plan, the customers, the product launches. Um, and a brand person just and brand people are brilliant. I mean there's I'm not saying anything about them. It's just that's not the path that they've come up >> like they're they typically are not sitting across uh the all of the different functions enough to understand them. (40:45) like they they don't have enough um connection and enough experience working with the other functions to be able to put that kind of plan together. And so I think what's really important with a CMO and the successful CMOs that I have seen are ones that deeply understand their strengths and weaknesses and they hire really good people to support them. (41:06) So like a VP of brand is really important and I've always had a VP of brand because it's critical to have somebody that can help to define your brands, can make sure that everything is at the high taste level, creates great content, creates great design, helps as you're thinking about your campaigns, helps you think about what are the creative ways you can get that across. So brand is critical. (41:28) It's just not necessarily at least in B2B, not necessarily the the the job that makes sense for that sort of top position. >> Interesting. Yeah, I might not know the definitions well enough, but I wonder if Udy Lagor and Dave Ghart both would fall more into the brand bucket, but it's a really interesting thing to think about. (41:49) Now with CMOS, is it safe to say that the high that the expectations on them and what they should be delivering is the highest it's ever been? >> Yes. >> With that, how do you manage the psychology of that? >> Yeah. I mean, I'll be really honest. I um I have never in my entire career seen so many CMOs opt out of full-time work. (42:16) I've just it's it's almost rare to find somebody that has decided to stay like if if basically if they've made their money and they've had a success. It's it's now uncommon for someone to be to continue the CMO role. Most of them are are leaving and being advisers and consultants and fractional CMOs uh because it it is brutally hard. (42:37) Uh, and I would say that the the ones that are successful are ones that just kind of continue to find ways to to be innovative and to and I think like Hub the HubSpot CMO is a great example where, you know, he's now got a podcast and he's talking about AI use cases and he's really kind of mandated through his organization to be much more AI forward. (42:58) Um, and I see a lot of people that I know that are successful are are the ones that are trying to reinvent themselves and reinvent their teams, uh, and are excited about change management, excited about helping their teams think about what are new ways of doing things. I think the ones that are successful are a little bit more technical because they're interested in the technology um, and interested in what's happening. (43:19) I think the ones that are struggling the most are ones that have not been interested in embracing technology and are kind of following the playbook and there really is no playbook anymore. >> Kalanley is obviously one of the most well-known brands in SAS. I would say I actually still I still use I'm noticing that I'm starting to do it less, but I'm still using it as a there's a term for it like I basically ask people for their Calendarly, not their booking link. (43:48) Yeah. >> Um um >> what are some of the biggest lessons that stand out from your time at Kalandley? So it it is um I would say that it is one of the greatest blessings in the world to have a brand that is so well known uh and you know and we always talked about it's basically the Kleenex of scheduling right like you do it's when people say what's your link they do say what's your calendarly and it's just assumed that your booking link is Calendarly uh I would say that that's one of the also one of the challenges (44:21) which is everybody knows countly as a link but we also have a huge amount of very sophisticated um you know uh complicated scheduling workflows that work for really large organizations. And so my challenge was how do you take a brand that everybody knows and how do you try to reposition it and how do you position it for a very specific group of people? And so the thing that I learned really quickly was and and this goes back to what we talked about before is I had I I could not do a repositioning for everybody in the world (44:55) because it didn't make sense. And so the thing that I spent a lot of time on was truly who are our most profitable customers and let's only go after those customers and everybody else like it didn't make sense to target anybody else. like our our cap was zero because mo the vast majority of our customers just came in through the verality of our product >> and so it didn't make sense to try to spend money to increase the verality to increase the casual users and so I pivoted my entire team and our budget to focus on how do we reposition ourselves (45:30) against a very small group of people where I felt like we could make the most inroads in educating them on the fact that we had these very sophisticated use cases that were specific specifically targeted to them. And so we went a very heavy ABM route. Uh and I think that that was very successful in terms of really helping the team focus. (45:49) And so I'd say that that's probably the number one thing is if you have a bigger team is focus. >> And most marketers don't like to focus. They like to do a bunch of everything. And where you can be most successful is making those big bets, making those trade-offs, being very explicit about what you're doing, what you're not doing, and then making sure that your team is absolutely following it. (46:13) Because marketers do not like to follow OKRs. They do not like to follow their plans. They love to go off and sprinkle their seeds everywhere and just do kind of the things that they want to do. And I call random mass of marketing. And so really making sure that nobody is doing the random acts of marketing that they're everybody is kind of putting all of the um firepower behind a couple of big bets. (46:40) I I I think that that worked really well for us >> and I assume that that pivot towards bigger customers meant focusing on enterprise fortune 1000 companies. Have you what have you found that works to close big enterprise accounts in 2025? >> I I don't think that that has changed very much. I think the the major thing that's changed is that the buying committee is very big. (47:07) So, you know, the the you really have to make sure that um you're arming you're you're understanding who that not only the buyer is like the person that you're talking to, but really understanding everybody that's part of that buying committee. And I think that that's what a good salesperson has to do. Um and I think that that's something that, you know, as a CRO that was on my mind, too, right? is making sure that you have the right uh sales training in place so that you are if you've got a six-figure deal, you're not just assuming that, you know, (47:37) Sally, who's a random director of purchasing can can buy it. That's probably not the case. You're going to have 10 to 15 people in a deal. And so understanding what are all the things that you need to have uh are there ROI calculators? Are there case studies? um you know who do you need to have on what information do you need to have on our side and what process you need to have on our side to make sure that the very extended buying committee uh and also security is really important data is really important. Um so making sure that (48:08) you have all of that buttoned up when all those people are going to ask for that massive amount of information come out of the woodwork already. They do. They really come out of the woodwork and all of a sudden the legal people and the purchasing people and the procurement and security and data and you're like, "Wait, I thought this deal was going to close tomorrow. (48:25) " And like, "Nope, just it's not." >> Do you think you'll ever take a full-time CMO role again? >> Uh, I get asked that all the time. Um, I love what I do and I would be surprised if in the near future I took another full-time job. Um, that I'm an entrepreneur. I I we we did mention one of my many jobs uh in in my in my past was I started a food business and I sold it. (48:53) Um, and I was the first hireer at, you know, multiple companies. And I love to build things. And when you're a CMO of a scaled company, you don't build any, you don't build a lot. You kind of manage a lot. And so what I love about what I do now is I get to work with tons of founders and CMOs and CEOs and I get the satisfaction of helping them build, but I don't have to deal with um you know budgets and headcount planning and uh you know performance reviews. (49:22) It's kind of nice. I think beyond the kind of we discussed the trend of a lot of marketers going fractional and and into consulting. I also do see a trend of CMOs or marketing leaders either going back into the IC role at a startup or going to a smaller startup where they can again get their hands dirty and actually >> be involved from ideiation to implementation rather than just do meetings and reports all day. (49:51) So I think there is that >> yearning to if you were to start join a startup today I don't know a rapidly scaling AI startup first marketing hire whatever CMO um you want to call that role what what would be some of the things at least you'd be considering evaluating um what are some of the tried and trueue things and what are some of the cool new shiny things that you'd be maybe considering or looking at it obviously depends But curious. (50:21) >> Yeah. Uh I mean I I would I am really excited about the idea of these go to market engineers. I mean I would definitely hire some super smart CS grad from Berkeley who can't get a coding job anymore and just have them have them go crazy. And I I I love the idea and I have encouraged everyone that I work with to really rethink their entire organization from scratch with the idea of how do you put in the technology first? How do you understand the all the AI agents that you can use, all of the um different data sets that you can use (50:55) to be able to enable your team? Um so that would be what would be exciting for me is to start with and uh I've always come into organizations with terrible data and so we hire these brilliant analysts and they're like Jessica, we can't get any reports because all of our data is terrible. And so I would be really excited to hire like really good data people to make sure that we have I was a former also a former investment banker so I love data. (51:24) Um and so like I would just love to have a really clean data set. I would love to be able to build reports right away so that we can deeply understand our customers from day one. And what I have found so often is that companies wait way too long to put in basic data, basic reporting, and they just don't understand the fundamentals of their business until it's too late. (51:46) So that's probably the number one thing I would do is just making sure that we all have a common set of uh understanding of our customers and our data so we can make really good database decisions right away. Um, and and then I would hire people. Everybody that I would hire would be people that are data oriented and that are focused on the collaborative aspects of marketing. (52:11) Like I would not hire a content person that's just happy to sit in a corner and write content. Like I want someone that is hungry to experiment and build content that drives revenue. And if if every CMO is focused on AI right now and how they can leverage AI and what new AI tool to implement and what AI workflow to build, what is being left on the wayside most in that pursuit right now that >> we're maybe forgetting a little too much. (52:42) >> Good good content for sure. >> Yeah. like there's just I think there used to be really interesting campaigns and really interesting content and now a lot of it is just quantity and I I I can't I just can't stand that. I can't stand the idea that you're just, you know, outsourcing all of your content, just pushing out enormous amounts of AIdriven content. (53:06) Uh and I still think that there's room for, you know, really interesting storytelling and I just I I don't see that as much. And I think one of the things that is saddest for me is because I think storytelling used to drive a lot of PR like people you always had to have interesting things to say to the press and so that drove a lot of this impetus for databased you know reporting right so like all these really interesting reports that you would look at and you would you know these proprietary data sets and surveys that you would do because you needed fodder (53:38) for PR there's no really no such thing as PR anymore it's it's it's gone by the wayside. side. And so I think a lot of that impetus to create really interesting database stories is gone. Uh and so I would love to bring that back and just but I and I think there's opportunities to still push that through your own channels. (53:55) It's just people don't do that as much because they're they're just in the race to create more and more and more and more and more. >> Very interesting. All right. People who want to learn more about you or connect with you, I'll link your LinkedIn in the show notes. Anything I didn't ask that I should have asked? anything you wish you had said that it didn't didn't say? >> I don't know. (54:17) I feel like we talked for a lot. We had we had a lot of good discussion. So, I appreciate it. It was very very interesting. Good questions. >> Cool. Yeah, I had a blast and I learned a ton. So, thank you so much for coming on. >> Thank you very much. >> All right. This podcast is brought to you by Project 33. Project 33 is the leading executive thought leadership agency for LinkedIn. (54:36) If you're looking to activate your founder, your CEO, your executives, or any of your internal subject matter experts and create thought leadership content for them to build trust and credibility for your brand, reach out at project33.io.