7 Biggest CMO Mistakes with CMOs Databricks, Zoom and Okta

It's.

Please welcome to the stage rick schultz, cmo at databricks. Janine pelosi, former cmo at zoom. Ryan carlson, former cmo at okta, and carrie lou dietrich, advisor at hypergrowth b2b startups.

All right.

Hello.

I'm so excited to be here today with these luminary CMOs. My name is Carrie Lou Dietrich. I'm a former CMO, most notably the head of marketing that took Atlassian Public. These days I advise hyper growth startups including Bill.com, sprout Social, formerly Miro Segment and many others. Today I'm here with Rick Schultz, a former colleague of mine at Oracle and the current CMO of Databricks.

Thanks for having me.

Thank you. And Janine Pelosi, the former CMO of Zoom for more than 10 years, from early stage startup to multi billion dollar company. And Ryan Carlson, the former CMO of Okta, again having started at a tiny, tiny company and ridden almost a decade to a massive company. Today we're going to cover seven big mistakes that CMOs make. So the first one we're going to hit on is strategy. So Jeanine and I talked a lot about this one because many CMOs come up from a functional expertise. They learn how to do their job, but they might not be involved in the strategic discussions happening in the C suite. Jeanine, this was a mistake you saw others make, but really leaned into yourself. Tell us a little bit more about that.

Yeah, I mean, one, thank you for having me. This is fun. Brings back some nostalgia. I was just saying this is where the first Zoomtopia took place many, many years ago. So it's good to kind of go back to those roots when you're talking about this subject. But you know, I think maybe from coming in early on, I came in to start the marketing function there. It was really about just driving revenue and surviving. I think, you know, you go through different stages and you need different things out of, out of your leaders survival mode. Was that in the beginning? So it was always thinking about the company first and what had to happen and then thinking about what hat you had to put on. And typically that was the marketing hat in my case. But sometimes it was the sales or thinking about finance or other areas of the business and context to what you need to deliver in your function to be successful. And without that context, you lose out.

On that and you got pretty deep. You were one of four executives that were really active in the ipo. You were thinking about net new products, you were doing sales, territory planning, you were not just in your lane of marketing MQLs. What led you to have that kind of hunger and tenacity?

Yeah, it was context. And I believe, I mean, Eric is a phenomenal founder CEO. It was about the best ideas and it was a culture of, I would say, really a level playing field. It was best ideas won and it didn't matter. So when we thought about driving, you know, quarter over quarter, what was required, we put more pressure on ourselves than anybody ever could have. It was profitable or bust before anybody was talking about that triple digit, same thing. Right. Growth mattered and it was all of us getting into a room coming up with that plan. And I think that creates ownership over those plans. Right. If you're given an objective that you don't have the context for, you're unlikely to meet or succeed. Right. So you'll hear me talk about context, but I believe the why in that context is really critical for the whole company to be marching in one direction.

And like I mentioned, these days I'm advising CEOs and CMOs and I advise the CEOs because it turned out when I just advised CMOs, I couldn't actually make them successful in their job because if the CEO has opinion, they're not sharing. If the CMO is not involved in the right conversations, they can't really do their job effectively. And another thing that comes up a lot when CMOs are potentially looking, going to be replaced by their CEO, like aren't working out like 6 years, 10 years and 8 years up here is that they haven't built the right leadership team. So when we were talking about what are some of the biggest mistakes we've made in our careers, Rick, you really brought up building the executive team around you was one of the biggest mistakes you'd seen and things you'd leaned into.

Yeah, well, thanks for having me. Also super excited to be here. And I would say almost nothing you'll do will be more important than, than building the right team. And so we put a lot of thought into the team we built and we had some, we've had been fortunate to have some pretty hyper growth years where, you know, give you a sense, we've hired 175 marketers on from almost a very tiny team in the last six years. And there were some years where we had to hire like 40 to 50 people on a base of like 20 or 25. And when you're hiring those kind of numbers, but you also have a really high bar. We have a very thorough process. You know, keep the bar high is like one of our company cultural principles. And you know, we have certain standards and I'd say the two mistakes you can easily fall into. And we definitely made our share of mistakes. I think we've built a phenomenal team, but we've also made mistakes along the way. And probably the two biggest mistakes are, number one is not investing enough time. And I always talk to my leaders about this because when you're trying to hire like the best of the best, like really high bar, but you also need to do it really fast. You know, those two things kind of tug at opposite ends of the spectrum. And so the only way you can do it is just invest in ordinary amount of time. So I always say like, hey, think about how many hours this search is going to take by the time you research, talk to candidates, do your outreach, talk to some deep candidates, many times, do your back channel reference checks, all of that added up. Maybe it's going to be like a 200 hour search. You're just deciding how many weeks you spread it over based on how many hours you spend every week on hiring. So when you're in a hypergrowth phase, and I realize not, maybe not everyone is at this moment in time, but it'll come and go. And when you're in that phase of like you got to hire, but you really want to keep the bar high, nothing replaces how much time you're going to invest. Like in other words, if it's going to take 200 hours and you spend it, you need to spend 20 hours a week to get it done. That quarter, if you spend 10 hours a week, it's going to take you two quarters and a quarter is an eternity, right in a startup. So that's one thing. The second mistake, which I've fallen into myself sometimes is you start to get in that conversation where you compromise the principle you have. In our case, that principle is we look for long term company builders. We look for other people who've been 5, 6, 7, 8 years and been promoted and built other companies and longevity matters a lot. And then every now and then I'll have a leader and we get involved in this discussion, we convince each other that it's okay to actually hire someone who's moved around a lot more. Which again, that might be fine for some, but for us that was not part of our hiring principles. And so we bend the principle. And this is kind of true in other things too. Like you bend a messaging principle you have or what have you, and 99% of the time you regret it, you should have just stuck to your original principles.

Yeah. Hiring is hard, and firing boldly to get the right team in place is probably the hardest thing leaders have to do. The third biggest mistake that we talked about was setting the right metrics. So you've got the strategy, you got the team in place. What are the right goals and metrics? And Ryan, you really had some opinions here where you made a wrong choice on a short term metric and led the team kind of in the wrong direction, but then recovered it. So tell us more about that.

Yeah, well, thanks for having me being on a panel talking about all the mistakes we made. This could be a really long panel if you let me get started first. I can't help but comment on what Rick and Jeanine both talked about because I think they're connected. A lot of people here, I'm sure, are founders. They're thinking about how do I think about marketing, who do I hire for it? And I think Janine's point is worth repeating that marketing shouldn't be something you do at the end. You know, everybody thinks about marketing as I'm launching this product or I'm launching this company. I'm trying to get buzz, I'm trying to get recognition, I'm trying to get awareness, I'm trying to generate pipeline. Yes, marketing has to do those things. But I think if marketing is going to do its job well, it has to be involved in the company creation. The story for why does this company exist? What do we value? You know, Rick, you were talking about your values. That's as much marketing as anything else. And so I see a lot of founders who look to hire somebody to come in and be bolted on. But if you're looking at building a team, don't overlook, you know, to Rick's topic, don't overlook people who are inside your company who have been there from the very beginning. One thing that we all have in common is we were very early at these companies. And so when we told the company's story and connected it back to the values and why does this company matter? We did so with credibility because we were there from the beginning and that was as much our story as anybody else's. So I think those two things are related. I know a lot of founders are thinking about hiring marketers and if you do interview them, ask them about metrics, because the mistake that I made, I thought I was being a really great leader. I thought I was being so smart, so strategic, I was going to tell everybody that pipeline mattered and I was going to do that in A couple of ways. Every meeting we had, whether it was my staff meeting or extended leadership meeting or the marketing all hands, it started with the same agenda. Item number one, how are we doing with pipeline generation in the quarter? I wanted people to know that it was important, so we put it first. But I also wanted the marketing team. You know, at one point marketing wasn't just demand gen or brand or PR. It was also product marketing and SDRs and marketing operations and sales enablement and developer evangelism. A pretty broad group focusing on that number. I wanted everybody to know that pipeline was their responsibility. Not just the demand gen teams. But what I didn't realize what I was doing when I put that number so big in light and made it so important, was that people would focus on that to the expense of all other things. And we were organizing a dinner between our CEO and CEOs of Fortune 500 companies. That's a high stress activity to get a dinner like that set up. And the person who was organizing it, she said, ryan, I don't think we should do this dinner. I said, why? She's like, I'm not going to Show Any Stage 2 pipeline created from this activity. And that's when I, you know, I wasn't happy with that conversation, but I was more unhappy with myself because I put us in that situation. So then we came up with a balanced scorecard which looked at, yes, the number one thing is pipeline generation, but there are many other things around that we should also measure.

And I think we're going to come back to this because one of the things I think I've named it number six, but I should have named it number four now that we've had the conversation this way. But one of the things I see earlier stage startups is that the marketers don't put in place their attribution tracking and they really don't have the tech stack and they can't see into the right data. So they not only don't have a balanced scorecard with the right awareness, lead pipeline, cost per opportunity, metrics that are so important to track, they can't track them and see through to them. So I think bringing number six forward, both having the right goals and then the right text is and marketing operations team is really, really critical. So moving along, back on track to the numbers, the next one is, can you go back one slide please to number four, not investing early enough in brand. And so Rick, you've said less so now at databricks, but at Alteryx before you were really focused on Demand gen and hadn't invested as much early in brand. And that turned out to be something you really changed when you came to databricks.

Yeah, I think it's a little similar to what Ryan's point about, particularly in the early days, you can easily become so pipeline focused because it's like air, you need the pipeline, of course, and it's like everything, it's like air, water, shelter, everything is pipeline, pipeline, pipeline. But I do think kind of looking back, it was a mistake in my prior company not to be more intentional and thoughtful about the brand earlier on in the life cycle of the growth of the company. And by the way, brand awareness doesn't mean you need to right away go spend a lot of money on a bunch of billboards or anything like that. It's a natural evolution. But it means even from an early on standpoint you should think your brand is really your reputation. So it's like you should be thoughtful and intentional about what does your brand mean, what does it stand for? And then as you keep growing, really codifying that, making sure your visual identity, the language you use, the way you show up at events, all of that stuff like reflects the brand and creates a reputation. That's the reputation you want in the market. And yeah, I think we invested earlier at databricks in doing those kinds of things actually. In fact, we have some of the same people who worked with Ryan at Okta because I always thought they did a great job at Okta with that and did a great job building their brand. And then once you have it codified, even when you have customers telling the story for you and stuff, you can kind of have them tell the story the way you want them to tell. Like if you're trying to emphasize innovation, they can talk about what they're doing that's super innovative or whatever the thing is. But you got to do that early.

And that leads right into the next mistake that we were talking about, which was having a strong, consistent messaging. And again, I said before Rick and I met, when we were at Oracle, I was running awareness advertising. I wrote ads for the front page of the Wall Street Journal. Larry Ellison had to approve every ad. And sometimes we would complain that it was so boring because A, it was the same ad format with that red bar and two, we would keep the same message for what I thought was an inordinate amount of time. But it turned out that in all the research we had the best awareness and association of the brand to other things. And not flip flopping really made a huge difference And Ryan, you had talked about that. I think that just this consistent messaging is a problem. You've seen so many CMOs fall into or inconsistent messaging and one that you had focused on.

Yeah, I think, you know, it's understandable. There's a lot of pressure on marketing to come up with ideas. It's, it's one of the, it's the creative field. What's this new idea? And if you're consistent with your messaging, it doesn't look new, but it is important for your messaging. If it's what I said up front connected back to why the company matters and what you stand for and what is your purpose. That consistent messaging can be really impactful long term and you have to resist the temptation to change just for change's sake. And while we're on this topic, I can't help but give Janine some praise because she came in early to one of my marketing all hands and did a guest talk at Okta. And we brought her in in part because we thought everybody's familiar with Zoom's out of home advertising strategy in the early days and we didn't know how you could do that because investing in brand is hard because what's the phrase? I know half of my advertising dollars work. I just don't know which half. It's hard as a new CMO or a growth focused company to justify spending money in that way. And you all did such a great job because you were clever in how you did your out of home advertising. You didn't use a big branding firm and agency. You came up with a lot of those taglines that you'd see on the billboard yourselves, isn't that right?

Yeah, we did it all in house. And that's where it doesn't have to be super sexy, but it also doesn't have to be incredibly boring. And I think it goes back to the metrics. We couldn't find any metrics, any vendor, anything traditionally out there for the type of advertising that we were doing. I mean, we were, you know, the cold emails that would come to us at the time for the sides of buses in San Francisco and the rest of it, like nobody was using those. And so we created our own basically proprietary way of measuring this. And it wasn't rocket science, right? It was, you know, where are the visits coming from, what's happening, you know, in these different territories and regions? And, you know, like that was our own way of measuring. And so we could, we could see and we knew which, which half, but we said the same thing, right all over the place. And it worked.

It sticks.

Yeah.

By the way, can I just. Can I just riff on the thing Ryan said? Sorry, I just want to, like, the messaging thing. I think it's so important to have the consistency through all the channels at the same time. But also, you're talking about. Consistency is more like what I call stamina, which is like, stick with it. Because I think it's easy to underestimate how long it takes to hammer a message into the market. It takes many quarters, sometimes years. And so you do really have to resist that temptation, I find, to, like, guess what you called whiplash. To change it too frequently. And we all fall into that trap sometimes. So for me, it's a little bit like the hiring thing, where you might have the right principle, but then every now and then you compromise it and then you just regret it. So I think for me, the common thread there is like, stick to your principles. Like, don't compromise them.

I've heard that just as you're starting to get bored, your customers are just starting to hear your message. So we live inside the echo chamber, but our customers do not live in that echo chamber with us. We're going to keep moving along, which hurts me because I want to just get deeper and deeper with these fascinating folks. But we wanted to leave time for you guys for the questions at the end. So I think the seventh mistake that we had highlighted, which I think is ever more present now, is not being your best self in tough times. And so when I look back on the things that I'm proud of and the mistakes that I've made, some of the mistakes were at Atlassian. The founders were in Australia. I was on the road to Australia, to Europe. I was tired. There was tension in my marriage. My children were young. I would get sick. You know, I hired someone that was the wrong fit. You have these times that are tough. And, you know, we know we were just talking ahead of this about the hard thing, about hard things. I don't know if you guys have read that book about founder tough times and how the tougher the times are, the more it takes from you as a leader to be your best self and not be impatient and rude and irritable and stay level minded. And, Janine, you just had such a lovely quote about how you guys thought about leadership in tough times.

Yeah, I mean, I think it goes back to, obviously, as many of you know, I mean, Zoom had a pretty historic ride through IPO and contributed a lot to society over the past few years. And with that Came a lot of challenges, a lot of growth. We went from, I think it was right around 2,400 employees to over 8,000 and about 18. I mean, there was some unprecedented scale and growth that we went through, good and bad and all the trying things that you mentioned. But what it came down to, and I was given this advice, is the advice was in the context of a lot of people getting it wrong, growth hides problems flat out. The time to be tough on your team is when you are doing well. The time to be empathetic is, is when the company is having a really tough time. And so often that is flip flopped. And so the only way to get around that is think about what could growth be hiding. And that gives you air cover. Right. And if you're private, all the better. Right. It gets a lot harder doing that in the public markets. Right. So finding that balance is pretty critical.

Yeah. It's tough times for all of us in different markets in different ways. I think one of the things that's been interesting for me interviewing these folks for this is just how it's not all easy and soaring. Right. There's a lot of tough times and hard mistakes learned. So we're going to take some questions from the audience. I think there's two microphones here at the front. And if you'd like to ask a question, you can come up to a microphone. Otherwise, I will keep asking them questions. Okay, I will keep asking them questions then while you decide if you'd like to ask more. So one of the things that founders want to know is how do they find the next you? Right. The average tenure of a CMO is a couple years. People change messaging because they change CMOs like spring outfits. So tell us a little bit about how you ended up at your company. Because, Ryan, you joined when it was 10 million in revenue.

No.

So actually, funny story. I met Okta when there were nine people and I had spent my entire career before that in product, product management, product marketing. And I tried to get them to hire me to be their first head of product. And I went through four or five rounds of interviews and didn't get the job. But I became convinced that what Todd and Freddie were building was going to be not just a successful company, but one you'd be proud to be part of. So I stayed on them for nine months. And then when they eventually wanted to build out product marketing, they gave me a shot at that. And I still almost didn't get hired. But I convinced them to take a shot on me. And I build out product marketing for the first couple of years and we, you know, in the early days we didn't find the right cmo. And a lot of, for a lot of the reasons I was talking about. And so my big piece of advice when I talk to a lot of founders is you certainly want to look for the person who's been there and done it and managed a team that you're aspiring to be like and you're going to grow into. But don't overlook the person that's there that has drive, ambition, has a chip on their shoulder. You know, one of the challenges with, with getting somebody who's been there and done it is do they have that drive to do it again? And for me, I lived and breathed okta. I told that story better than anybody and it was still not easy for me to get the CMO job, but I'm lucky they took a chance on me. So yeah, don't overlook somebody who lives and breathes your company because that's super important.

Okay. Hunger and knowledge. And Jeanine, I was stalking you before I got to meet you and I listened to all bunch of your podcasts and one of the things I had learned about you was that you worked with the CEO before and you worked in the same kind of category before. So you came in so primed to really help him flourish. Tell a little bit about that story.

I'd say kind of. And the reason being is because part of why Eric ran the company the way that he has is because of his prior experience where there was not a line or there was a brick wall almost between go to market and what was happening on the engineering and product side. And it was not something he wanted to replicate. And so while we had some shared experiences, we hadn't worked super close together, but we definitely, I think, had that drive, that kind of builder mentality. We operate with this immense sense of urgency, which is fun. But you know, the advice I give when asked this question is find a company that you admire and then hire the person one level below, you know, somebody who has something to prove, who is probably doing a ton of the work and think about where you are as a company. You don't need to go and, you know, be very careful about when and who you hire and the skill set that you need at that time versus thinking about what it is that you need this person to grow into. You know, if you find someone who's self motivated, you know, continues to develop themselves and is open to that, then they can grow with the company and if not Then maybe it's time to part ways and find someone else. But don't overlook what you need in the, in the short term, because as many of you know, if you can't get past that short term, there is, there is no long term.

Yeah, I'm going to go to the questions because I see you guys lined up. How about we start with one from over here?

Hi.

Yeah.

You've talked about the relationship between brand and demand. What's your take on the role of culture as it relates to brand and demand and the role that marketing should play in defining or developing or accentuating that culture?

I can, I have a strong opinion on this one. Culture is your internal facing brand. You have no company, you have no future. If you don't have a culture, if you don't have people that give a shit. I don't know if I could say that here, but like, you don't have anything, right. You have to start with your people, make sure it's a place that they want to be a part of. Especially, you know, I can't believe we've actually been on a panel for 20 minutes and haven't talked about remote work. But like, it is so much harder today than it, than it ever was. When we start with Zoom, we were in the office five days a week before the pandemic. Right. And so it is harder. You have to be more intentional. Right. A lot of the communications that folks have today are task based. Right. You take a meeting, schedule a meeting because you have to get to something, doesn't leave a lot of room for the other things. And I don't think it's been figured out quite yet. But you know, it is critical.

And we had a quick conversation, Rick, where we were contrasting, I think Okta CEO and Databricks CEO, how so many cultures are built around some of the early stages styles of the CEOs. And that was very true for Atlassian as well. And in fact, we almost like countermerged our brand principles and our culture principles. They were very intermingled. Do you want to talk a little bit about that?

Yeah. I think the CEO is always going to have a strong say in like building the culture and defining the cultural principles. But I think to your point, your points both of you made earlier about like, marketing has to be a big voice in that and part of setting the strategy. The same is true for the cultural principles. And while I don't think they need to be the same as your brand attributes. Exactly. They need to be consistent. They need to be like, you Know like for example, you know, we think about when we defined our brand, we intensely like blurred the lines between how we think about ourselves and how we think about our customers. That was something I admired. That tableau I thought had done very well. So we tried to like emulate a little bit of that. So when we talk about when we don't use these words externally but like when we think about, hey, our brand needs to come across as innovative, it's not just because like we've invented open source stuff. It's because our customers are doing like amazing things with our product. And also some of those things they need to filter through the company. But you can also have additional company principles, I think, like put the company first or be truth seeking or like the culture can be. There can be some things that are just true to the internal team.

Just one quick comment on culture. For years, every Monday when new hires came into Okta, they go through orientation, they get their laptop, they get everything set up and then the first presentation they would get was from me. I'd give them the company pitch and then a pitch about our values and I talk about how these two things are related. And at one point, you know, we're hiring so many people. The people OPS team and the HR team said Ryan, you don't have to come do this presentation every Monday. And I said, no, I want to unless I'm traveling. I'm doing that because whether you're in finance, whether you're in, you know, you're not customer facing, you're going to interact with somebody outside of your company and how they, you know, how you do so informs how the world thinks about your company. The brand. It takes years to build up a brand that has the characteristics that company like Octa did trust but it can be lost very quickly. So you have to invest it in a bunch of different ways. And like I said, I think, you know, culture is to get it right, it's sustaining. You'll have people who are at their companies for years and years and years because why would they want to go anyplace else? They believe they're not mercenaries, they're missionaries. And that comes from culture as well.

Which is so important in the hiring and firing. I feel like the culture piece is really hard to put your finger on, especially with implicit biases and everything. But you know, when you've got hired someone who doesn't really have the drive or the work ethic or they're very like self aggrandizing in a culture of collaboration. So that's A tricky one. Okay, next question.

This might be a little, not on this top, around this topic. This might be a more tactical question, but it's ready to see such amazing panel of people from marketing and marketing leaders. So as a, as a CMOS and somebody who's handling such larger budgets for your marketing spends, from your lead generation standpoint, you manage like a budget for your events and webinars, field marketing, those sort of deal those sort of things from your experiences, what is that ratio that you see? Like let's say, I mean of course there are multiple variables involved, but if you would see that if a company is spending 70% of that budget on let's say events and webinars, would that be an eye rolling moment? What would be that number where you would say okay, this is pretty average in enterprise space.

Well, I can go first if you want. I think the first thing you got to think about is the total marketing budget. What percent goes toward people and what percent goes toward programs. I don't know that there's any one right answer because it might vary by segment or the type of marketing you're doing. It certainly varies by stage of company too. Like I think when you start early on you probably run into like a little over 50% of your budget goes to people to like. I mean FTE, I'm just talking FTEs, not even contractors like, but then as you get bigger you want to kind of probably move a little bit more to programs. Like for example, we're like more like 60, 40 programs within programs. I don't know that there's one right answer. I think it just depends what works for you. It depends how much you need to create an always on flow of leads versus point in time events. And you need to look at the balance of that. And also can you manage to hit your pipeline targets with less than your overall budget such that you can start to siphon off some money to invest in brand awareness. Stuff that won't be as measurable or that won't have attribution around it. That's kind of just how I think about it.

I think it's also tough if it's product led growth or enterprise sales. Those are very different motions. When we were talking about the brand question, Jeanine, you guys invested really early in analyst relations, which most startups wouldn't do, and customer stories and that type of thing, right? Isn't that where you made oversized investments?

Yeah, definitely. I mean I thought about two principles the day I started and we did not have a formal marketing function at all and no budget. Two where we ended up recently, very different but the same principle still applied. One was building a preference for the brand. Keyword is preference. And the second was validation. And that validation, you needed it from your customers and you needed it from the analyst community. For us and in our space was key. And a lot of people don't think about that until later. But the reality is those relationships, whether it be the customer or the analyst, take a lot of time to foster. And so starting that as soon as you can. And then to go back to your question, I would just say the international piece and or the different routes to market. Whether you're thinking about an E commerce channel, direct, it's going to be very different and be open to it being different. Right. Like if you have one set of ratios globally, you're probably not thinking about it in a way that is deep enough. Right. Because some markets are going to need more brands. Right. If nobody's knocking on the door then you need to invest in that. People think about what's just happening through more of the later stage attribution channels. But people don't wake up in the morning thinking about your brand. So it could be very different in the US than it is in Colombia.

Let's take the next question over here.

Hi, I'm Ashley, the founder and CEO of Living Security. We're Austin based cybersecurity startup. We sell via enterprise. So marketing for us has been like a two headed beast and I feel like the brand demand has been like a theme in the conversation. At one point we had two VPs of marketing, somebody who did like brand and category and somebody who did demand gen. We're a startup so we can't really have two heads of marketing. Have you guys found a way to optimize for that? Is one sort of sort of lean better as a leader and then they need to hire below them like or can that vary company to company? Just how do we think about prioritizing brand or demand?

I, I didn't use the term demand. I actually ripped it out of everything. I didn't think about demand generation. It was demand creation and demand capture and everything felt that's why we existed. And so we didn't, we didn't kind of over rotate on one or the other. We knew we had to drive revenue and you know the, the tactics that you took at the time, whether it was a bus shelter or doing a customer advisory panel or ongoing demos and webinars. Right. They all kind of had to work together in concert. And so that to us was really key to blend them in the early days.

I'm sorry, I didn't mean to interrupt you. I'd say for early stage companies, CEOs flip flop. They come out first hard on demand and then they realize that their demand gen head doesn't know enough about the product and the customers in the category so they over they fire that one. They bring in the brand person and then they say oh, they're too high level, I need someone more technical. They don't understand the metrics, they're not really getting demand and so then they over rotate. I mean I think that's basically what happens. Yeah, right. That's why I'm in business. I advise companies who are flip flopping and I pair with the person who doesn't have the other side. I mean what you're seeing. I have an obsession with CMOs who have been in a job for more than five years. All these people qualify. I have a list on my whiteboard of who they are and what company they've worked for and why. I admire them. And all of them are generally multi time cmos. This is not their first rodeo. They've done both the jobs. Like what happens at startups is we're hiring step up candidates who you know, Jeanine's advice is great. Right. A number two at a great company in product marketing is going to be learning to make. So you either need to let them hire someone exceptional, put someone around them or give them the time and the space to work that out. But I think there's no either or. It's demand creation and demand capture and both have to happen.

Yeah, I don't think there's any one profile that can be the head of marketing necessarily as long as they surround themselves with people who complement their skills. Although what's interesting, I've sort of two comments. One is one thing that's interesting is you didn't actually mention product marketing anywhere in there.

That's in our product organization.

Oh, I see. To me everything in marketing is better if you have really good product marketing because your analyst relation, your pr, your field events, your conference, name it, your digital ads, whatever you name, it's all going to be more effective if you have people who really understand the audience. The value proposition have defined these crisp messages that you're going to stick with for a long period of time and all that stuff. So to me that's got to be somewhere in the core. It doesn't necessarily have to be that the leader came from that background, but that's One thing, second thing is in a resource constrained world when you're early on and you don't have a brand that a lot of people know. One little trick that I found is you can do demands in that's still building pipe while you're raising your profile. And one trick for that is to associate yourself with a bigger brand than your company. And that there's lots of ways you can do that. You can do a competitive attack campaign which I think you guys did early on with Microsoft. You can do partner with someone much bigger who's incented to partner with you because you have something more innovative but their brand is bigger and they get you to the right audience. We did that at my last company with Tableau for example. That's why people do Gartner early on is because that's a big brand. Try to figure out if there's ways you can attach yourself to a bigger brand that reaches the audience you care about.

We did that.

Yep, we did.

Yeah.

What my quick take on this, this topic of, you know, demand gen versus brand. There's a famous enterprise software CEO who said any enterprise software CMO worth her salt has to have the company's pipeline target tattooed on her forehead. And his point is that pipeline matters. And we talked about that a lot. And the issue is that if you don't take care of pipeline, you're not around long enough to put build a brand because it takes a long time. But at the same time if you only focus on pipeline, you're not world class. You have to be, you have to find CMOs who can do both. Which I think is why it's hard. You either, you know, you're finding a demand gen centric person who maybe doesn't, you know, those, those, those professionals don't typically go deep on product. They don't have a product marketing background. A great storytelling CMO maybe isn't fluent in data and statistics and can get into those, but unfortunately that's the job. And so you know, I think Ben Horowitz famously says when you're hiring executives hire for strength, not for lack of weakness. Be aware of their weaknesses, but hire for the strength you need. And in your case it might just be pipeline is the number one thing. It might not be that way for two years from now and then put other people around that leader who can accommodate you know what they're, they're, they're not that great at. I was very lucky we had a demand gen leader who was my right hand person for many years because I didn't come from that world. And he did an awesome job and I pushed him. I didn't, I didn't just let him do whatever he needed to. He can attest to how hard we pushed. But I wouldn't have been able to do that job as long as I did if I didn't have somebody like that taking care of the demand gen side. And I totally agree with Rick's point. And none of it works if you don't have great product marketing. It doesn't have to be in the marketing organization, but product marketing is the glue that binds us all together. I think.

But ultimately a unified marketing org. I think all of our unified marketing orgs were product marketing, brand marketing, demand gen, and then BDRs are in or out. Right. But those are the three stools and expertise. Next question.

Hi, thank you guys so much for this panel.

My name is Sydney Craighart and I help brands increase their market share with diverse audiences. So I wanted to hear about what has been your approach to inclusive marketing so that you can engage diverse audiences appropriately and authentically. And, and what are you doing to help your teams to develop those skills?

I'll start. You know, I've talked multiple times about how a company's values are part of marketing and your culture is important in that regard. I talk about that a lot because I believe it. But I also, I think this is where inclusivity starts with your company's values and it's making sure you're getting, you know, you're getting access to the most diverse talent because if you're a hyper growth company, the name of the game is getting as many people to join your company as possible. And you can't do that if you have systematic biases in how you're, you're recruiting people and screening people and hiring people. But just as important is making sure that those people feel like they can bring their authentic selves into work. And I think if you do that and if you live that, then you're also going to be sensitive to your customers. You're going to, the messaging that you have is going to take that same form. So I think it's, at least in my experience, it starts with the values and the culture that you're building. And then if you hire the right people, they'll do the right thing.

I had the privilege of leading our philanthropy as part of our organization and key to that was education. Kind of no big surprise there. So for us, I felt like it always really started with our communities. All the things, of course, that he Just said around hiring practices and having a diverse workforce and such. But I always felt like getting into those communities and starting there for us, it inspired us in a different way when we talk to our customers, when we think about the marketing, getting into those different communities was key to that. And then it became more natural and it didn't feel like something. The thing that I can't stand when it comes to this topic is the programs. These are these bolt on programs that these companies run or these initiatives that it's like, how do you take it out of that and put it into just the everyday workflow of the organization? And that allowed us to do that.

Thank you.

Yeah, I mean, we. Thanks for the question, Sydney. We, I think, could still do better externally, to be honest. Like, we've done some things with like organizations like Girls who Code and Women in Big Data and things like that. But I think actually first you gotta get it right internally. And we've been kind of working on that in terms of doing a lot of training around unconscious bias and even adopting tools that help with that. For example, I didn't even realize until I used this tool called Data People that when I write a job description, it's not always by definition the most inclusive job description. So this tool actually scores it and tells me like, oh, you have way too many requirements or you don't need these extra four words or whatever. And it's scored and you have to have a minimum like 85 score. You can't post your position. And it's actually very helpful for me because I'm like, oh, I didn't even realize. Yeah, I guess I don't need the word aggressive next to targets. Like, if that's like maybe alienates people, then I just delete it. It doesn't really add any value. And so, you know, just in terms of like hiring. And we got to a point a few years back where I looked at my team and I was like, hey, we're 50% female in marketing, but our leadership was only 25% female at the time. And so then we adopted some of these. We trained people on unconscious bias, including myself. We adopted these tools like data people and stuff. And then we got to a point where we were like 50, a little over 50% female leaders a couple years later. So I think starting internally kind of for me is the most important and then it kind of works its way outward.

I think we have time for these last two questions. Thank you for the question.

Sorry, I'm short. Hi, my name is Bri. I am an ops team of one at a bootstrap startup. And given that you are all very experienced, I would love to get your take for someone junior as myself and I work exclusively with our executive team. You know, how. What would you advise, like, someone in my position, say, or approach the issue of, like, when I'm recognizing that people technically above me are not their best selves, and you can see that it's impacting the organization as a whole. So essentially, what's something you wish someone had told you when you were not your best self and it was affecting the track of the organization? That was a lot. But thanks.

I mean, I have a. I have a story. It's actually somebody who's on Rick's team now. She's awesome. And I made it. I tried to make it a habit of taking. Trying to understand everybody on the team, what their career aspirations were, you know, so I knew that so I could, you know, help them in their career, but also place them in positions and projects and things like that that would get the best from them. But I took this woman out to lunch one time, and as part of these. Part of these discussions, I was giving her feedback and stuff. And her name is Lindsey. And I said, lindsay, do you have any feedback for me? She's like, are you sure? I was like, yes, please. I would love. I would love feedback. And she said, well, a lot of people right now are afraid to make mistakes. They're feeling that the bar for quality is very high and they're afraid. And it was like a punch in the stomach. We had just come off of our version of this event. Our customer conference was called Octane. And the pressure for an event like that, we did want it to be perfect, but I accidentally let everybody think that everything had to be perfect. And of course, the enemy of innovation and new ideas is people feeling afraid to take risks. And so I guess what I would say is, you know, have leaders who encourage that feedback, create a culture of feedback. There's a lot of studies around the ratio of positive to negative feedback. You need to build up trust so that when you. With positive feedback, so that when you give the negative feedback, it's more well received. But you could, you know, if somebody's not acting their best selves, give them the feedback. You know, if they. If they're not comfortable hearing it, maybe that's a sign of something too.

By the way, I don't know if I have a good anecdote like that one specifically, but there's a good book called Radical Candor, which You know, if you haven't read it, I recommend, I think when used appropriately, radical candor can work regardless of reporting structure or function, whether you're peers or you're talking to someone above you or below you or whatever. Doesn't really matter if it's used appropriately. Radical candor can also be used in a negative way where people use it as a calling card to like, hey, I'm about to unload some radical candor on you. And it's like, you know, they're using it as like an excuse to kind of be a jerk or whatever. But like. But if you actually read the book and you look at like, it's really the combination of showing that you care and that you have the best intentions and that you wouldn't bring this up if you didn't care, but then you just provide some honesty in a candid take. It's easily appreciated, I find.

Yeah, we only have another minute, so I'm so sorry we missed your question, but hopefully we can meet you after, I think, where I'd like to end this, because this is kind of a good question. Good point. You know, we work in difficult times. Sometimes we work for difficult bosses. But one thing that creates an enduring career is navigating that together with your executives. And do any of you guys have anything left to say about just kind of your persistence? Because I think, Sorry, I'll make my statement, then ask my question, which is what I've seen in these CMOs who have gone the long haul from the tiny company to the massive company is staying endurance. Like, times are tough and you're there, times are good. Or you're there and times are, you're still there. Right? You didn't take another job, you didn't walk away. Like, what. What was it in you that like, gave you the endurance to go the long haul in these jobs?

My take on that, you know, Ben Horowitz famously says, you know, you want to build a great place to work. And so for me, I felt like I was part of a great place to work. Okta was a great company, but I also felt I had a hand in building that too. So if you feel like you're at a, you know, pressure is a privilege. Colin Jones, a great CRO, says that all the time, pressure is a privilege. I think it's a Billie Jean King quote. And just recognizing that building a great place to work at a hyper growth company is never going to be easy. It's not supposed to be easy. Anything that's worth doing that is important is not going to be easy. But pressure is a privilege, and that, you know, at least help me sustain that and also build a team. Team where everybody that was there believed and they wanted to be there, because why would they work anyplace else?

I think that the why context that we brought up before, like, definitely having that sense of purpose, whether it's for yourself or your team, if you're not motivated, your team's going to feel that they're not going to be motivated. And so understanding and making incredibly clear, no matter the size of the company. It's much easier to do when you're small, but it's possible when you're larger. And going back to the messaging piece around simplicity, that is. That is key, like making sure that, you know, people understand why you're in business, what they're a part of. Right. I never felt like I was at work. I felt like I was a part of something and. And I know many of my peers felt the. The same way.

Yeah, I just echo. I mean, I think commitment to the cause and just the love of the build is critical. You gotta hire for that. You gotta build a team where you feel that everyone feels they're in it together, they're building something special together. And like Ryan said, it's not always gonna be easy to build. Like, they're gonna have bumps in the road and stuff, but if you have that just love of the build and commitment to the cause, you'll fight through the tough parts.

Well, I'd just like to thank these fantastic CMOs for joining us today.

Thank you.

And thank you to Jason and Caitlin and all the Saster folks for making this all possible. So thanks and have a great conference.

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