The B2B CMO Podcast with Jon Miller and Sydney Sloan

Lena Waters is a marketing executive and advisor who specializes in the inflection point where product-led growth meets enterprise scale. She has built and led global marketing teams across growth, demand, and brand at companies including Grammarly, DocuSign, Responses, and Lookout, and most recently served as CMO at Notion. Across those roles, she's operated both enterprise and product-led growth motions and developed a point of view on how the two can reinforce each other rather than compete.

Lena joins Jon Miller and Sydney Sloan to share her controversial take: stop trying to persuade your buyers and start giving them proof instead. In this episode, she breaks down why she'd rather put a marketing dollar into product experience than a brand campaign, and how that thinking took her from DocuSign to Grammarly to running go-to-market at Notion.

Lena walks through how she merged product-led growth with enterprise sales without treating them as competing motions, why she thinks MQLs are measuring the wrong thing, and the three blunt questions every CMO should ask their CEO before taking the job. We also get into why she thinks the AI-native marketing team problem isn't a talent problem at all.

Jump Into the Conversation:
(00:00) Where PLG meets enterprise scale
(01:40) The CMO who resisted becoming a CMO
(03:51) Selling the pony: An origin story in positioning
(07:54) What "strategic" actually means in the AI era
(10:06) Repositioning Notion from note-taking to context platform
(12:44) MQL vs. MQA and letting the data kill the old metric
(15:00) When brand spend is just rented attention
(20:47) Community compounds, awareness evaporates
(23:14) How Notion measured a narrative change
(25:51) Three questions every CMO should ask their CEO
(33:13) The AI-native team is a permissions problem, not a talent problem
(36:24)Why speed beats consensus

Key Takeaways
  • Replace persuasion with proof.  Lena argues that much of traditional B2B marketing has been designed to persuade prospects before they have meaningful experience with the product. MQLs often measure whether someone consumed a whitepaper, webinar, guide, or event and then translate that behavior into assumed buying intent. Product experience provides a different signal: someone has used the product, experienced its impact, and potentially built a dependency on it. The strategic question becomes how much value you can let customers experience before asking them to buy.
  • PLG and enterprise don't have to be competing motions. Lena's experience owning both enterprise and product-led targets changed how she thought about growth. Individual product users can build durable brand affinity, while small teams and developers can become a front door to the enterprise pipeline. She doesn't argue that every company needs a traditional PLG model. Instead, she asks how wide a company can open its front door—through a free experience, API access, a usage-based tier, hands-on proof of concept, or another way for customers to experience value before the contract. 
  • Build brand assets that compound. Lena distinguishes between attention that disappears when spending stops and evidence that keeps working for the company. Community, original research, customer advocacy, and the stories customers tell about a product can create value long after the initial investment. Rather than asking a CFO to simply “fund brand,” her approach is to show how those assets keep returning value and use a combination of quantitative and anecdotal evidence to demonstrate whether the company's narrative is actually changing.
  • AI-native marketing starts with permission, not the org chart. Lena pushes back on the idea that AI transformation is primarily a talent problem. Before debating new roles or hiring more generalists, she asks whether marketers actually have access to the CRM and product data they need to execute. She also argues for moving away from teams organized around individual channels and toward one shared department outcome. AI can dramatically increase production, but that advantage disappears if the company keeps the same slow approval structures around the work.

Standout Quote
  • “If you can help somebody experience the product before they buy and they already know what you are before they arrive, then the funnel stops doing the persuading that we've been trying to do all this time. And the product and your company reputation do it first.” — Lena Waters

Guest Links

Mentioned in this Episode

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What is The B2B CMO Podcast with Jon Miller and Sydney Sloan?

Welcome to The B2B CMO Podcast, a show for marketing executives who are redefining what it means to be a strategic leader. Join Jon Miller and Sydney Sloan every week as they talk with the very best Chief Marketing Officers who are navigating the modern marketing playbook and positioning themselves as strategic leaders.

Each episode, we unpack what it really takes to lead through complexity, earn trust at the strategy table, and shape the future of growth.

We’re building the community, research, and frameworks CMOs need to reclaim their strategic role and drive sustainable growth.

For more marketing leadership resources, visit [b2bcmoproject.com](http://b2bcmoproject.com/).

Jon Miller (00:00):
Welcome to the B2B CMO Podcast, a show for marketing executives who are redefining what it means to be a strategic leader. I'm Jon Miller.

Sydney Sloan (00:08):
And I'm Sydney Sloan. Between us, we've led marketing orgs at companies like Marketo, which Jon founded, Demandbase, G2, and Salesloft. For more marketing leadership resources, you can visit b2bcmoproject.com. And now let's get into the show. Hello and welcome to the B2B CMO Podcast. I'm Sydney Sloan here with my co-host, Jon Miller. And today's guest is a marketing executive and advisor who specializes in the inflection point where product-led growth meets enterprise scale. Truly, you will see. She's built and led global marketing teams across growth, demand, and brand at companies like Grammarly, DocuSign, Responsys, and Lookout, and most recently as the CMO at Notion. She led the global go-to-market strategy as the platform evolved from a beloved productivity tool that we all use to the leading AI connected workspace. She is one of the few marketing leaders who's done true double duty, carrying a hard enterprise number inside companies with strong PLG motions and big targets on both.

(01:15):
She's learned a lot about how each model can reinforce the other. So truly PLG to enterprise. Today, my friend, welcome, welcome Lena Waters to our show.

Lena Waters (01:26):
Thanks so much, Sydney. Hi, Jon. It's great to be here.

Jon Miller (01:29):
Oh, so excited to have you on here. I mean, we've known each other for, gosh, I don't know how many years, but I don't know if we've ever had a chance to dive in and talk like this, so I'm looking forward to it.

Lena Waters (01:38):
Good, good. Me too.

Jon Miller (01:40):
People get into marketing and become their CMO role through so many different routes. So can you tell us your CMO origin story? How did you get into this from wherever you started?

Lena Waters (01:53):
Yeah, that's a great question. I'm a CMO who actually resisted being a CMO and turned down a lot of those roles because I really liked being a strong operational number two to a CMO. And I did that for almost a couple decades. When I was at DocuSign in particular, the last couple years there, I was responsible for the product-led target in addition to running global demand and all the enterprise machine that I had been running up until then. And that kind of really lit a fire under me in terms of owning an enterprise number, a PLG number, rebuilding two separate teams around this sort of single revenue target. And that's where something really clicked in terms of how I think about marketing leadership. I think that individual people using the product built our brand more durably than anything that we were doing on the enterprise side.

(02:43):
And somebody actually using DocuSign and understanding what sticks is better than any kind of ad impression ever will do. The other thing is that small teams and developers that had API access were actually a front door to building an enterprise pipeline. And so this sort of realization that you can merge a couple different routes to market and that you really needed an executive seat to make that happen made me, one, really intentional about choosing my next two companies at Grammarly and Notion and really getting closer to the product team and the PLG motion. And two, really changed my mind about taking on a larger go-to-market role in terms of being able to run both models at once. That real product led motion, the number inside the same company is one mandate. And I think that combination is less common than either one alone. And once I learned that those aren't really competing motions, I wanted a bigger seat to be able to do that and that's what led me to here.

Jon Miller (03:37):
What about just getting into marketing in general? You studied marketing in college even, so it seems like maybe you knew about this since early on.

Lena Waters (03:44):
Do you actually have a marketing

Sydney Sloan (03:47):
Degree? Most of the people we talked to are like, "I had no intention of being in marketing."

Lena Waters (03:51):
Yeah. Oh God. Okay. Well, how far back do we want to go? I have a couple really origin stories. When I was 11, I outgrew my first pony and had to buy a bigger horse. And I'm really dating myself. You had to go into town to the newspaper and fill it a form to put an ad in the classifieds. So for folks that don't remember, there used to be these things called newspapers that were hard printed and they had these classified ads in them and they charge by the word. So I was trying to write this really short ad to sell this pony and I'm standing at the desk with my pencil and I said to my mom, "I don't know if I should sell this horse Ms a rodeo gymkhana eventing pony or if I should sell it as a show pony because I was doing all of it." And she kind of looked at me and she goes, "What do you mean you don't sell her as something?

(04:30):
You just sell the horse." And something just kind of happened in me where I went, "Well, there's two kinds of people in the world, people who understand that you have to position this as something and people who just sell a horse." And it took me a while to figure that out. But to my college major, when I was figuring it out and I was talking to my mom, she brought that story up to me and she goes, "You've been a marketer I think since you were 11 years old, so maybe you should go get a degree in it since it seems to come natural."

Sydney Sloan (04:54):
That is a good origin story. And then we also knew that you were a show person.

Lena Waters (05:00):
Yeah.

Sydney Sloan (05:01):
4-H? 4-H. Did

Lena Waters (05:03):
You do 4-H? Okay. 4-H up in. Yep.

Sydney Sloan (05:06):
Go ahead. Up in Canada.

Lena Waters (05:08):
Yeah. Yeah, 4-H up in Northern Canada in British Columbia. So yeah, it teaches you all sorts of things about how to be useful and capable in the real world.

Sydney Sloan (05:16):
All my friends showed horses and got to wear the great outfit. I also was in 4-H, but I showed cows and got drugged around the ring by big cows. So we do have

Lena Waters (05:30):
Another

Sydney Sloan (05:30):
Yet thing in common.

Lena Waters (05:31):
See, something in common. And the thing to remember about 4-H, and I highly advise it to those of you who are raising kids, the 4-H motto is learn to do by doing. So I think that translates well to lots of different disciplines.

Jon Miller (05:43):
Is there a marketing lesson there for you?

Lena Waters (05:47):
Marketing lesson. Well, to Sydney's point, if you went to the fall fair at the end of the year and you showed your horse, you got to keep your horse. If you went there and showed your cow, your cow ended up getting bought by a supermarket, which had a sadder outcome. So think about what kind of outcome we're trying to achieve.

Sydney Sloan (06:03):
It was $2,000 though. My brother, I showed heifers, so they didn't do that, but for the steers they did, and that's how my brother made a lot of money.

Lena Waters (06:11):
Yeah, you can. Hardware pays off. I

Sydney Sloan (06:14):
Mean, if you're on a farm, you accept that that's what

Lena Waters (06:19):
The outcome is. Practicality.

Jon Miller (06:20):
Did anything bring you towards B2B? Because obviously PLG, I understand the path into PLG, but growing up thinking about horses, what brought you into demand gen and B2B?

Lena Waters (06:32):
In demand gen. When I was in university in Canada, I took this course called services marketing, and it was all about the idea that when you think about services, it's different in product, which I sort of equated in consumer at the time as in services marketing, the service is created at the same moment that it's consumed. And I ended up writing a whole paper on it. But the idea that ended up translating into B2B is, one, SaaS is sort of the obvious parallel to that. And I think two, there's this idea that persuading people in groups is harder and more interesting than persuading basically the same single person ICP over and over again. And to me, the dynamics of a buying team and the fact that there's so many gotchas here, the biggest mistake you make in B2B marketing is underestimating the number of people who have influence on a deal.

(07:24):
And that concept of persuading groups of people and working with the dynamics of humans within companies just seemed like there was just a lot more legs to it. Consumer brands are interesting and valuable, but you're sort of doing the same thing over and over. When you get into B2B in an enterprise sale, you're creating value within companies. I think that's a more complex motion to run and was more interesting and it was just something I was drawn to immediately.

Jon Miller (07:49):
Super cool. And a great segue into talking about strategy. So Sydney.

Sydney Sloan (07:54):
So one of the things that the reasons that we formed the B2B CMO project was we wanted to really understand how can CMOs keep their seat at the table and what does being strategic actually mean? How do you show up as a strategic CMO, not just the person that's running the big conference or the trade show? And so in your opinion, in your experience, what are some of the things that you would highlight that makes the role strategic? I

Lena Waters (08:23):
Think it's a really great question to ask, particularly right now as we're in the midst of all of this transformation that AI is driving and it's a more fundamental thing. We went through things like cloud or mobile and those were interesting, but it's not overstating it to say that this is a generational change. Because of the impacts that that's having, I think now strategic means that you have to ask this hard question of, is the machine that we're using still the right shape for how people buy now? I think tactically we used to think, how do you get more out of the machine that you have? How do you get better leads, more conversion, a tighter funnel? I mean, that's all real work and I'm not against the funnel. I've built lots of them. But the strategic thing you can do now is step back and say, are you spending to push people through a motion that doesn't match how they want to come in?

(09:12):
This is a little bit of a callback to my experience about merging PLG with enterprise. If you can help somebody experience the product before they buy and they already know what you are before they arrive, then the funnel stops doing the persuading that we've been trying to do all this time and the product and your company reputation do it first. And that's a fundamentally cheaper, faster, I would say better motion and it's more available to more companies who think that they qualify for it. So I think to sum that up, I think the short answer is yeah, you have to re-look at the machine that you're building, but I think some of these boundaries that we've had before between are you product first or sales first? Are you PLG or enterprise? Are you building leads in the funnel? Are you trying to drive trials? I think those are derivative questions that aren't really getting to the heart of the matter of can you provide proof to your customer as opposed to providing persuasion?

Jon Miller (10:06):
Can you tell us how that played out at Notion? When you were trying to establish yourself as, "Hey, I am not just arts and crafts, but I'm a strategic part of the team at Notion," what did you do? How did you really earn that role?

Lena Waters (10:27):
I think at Notion, what they were looking for and how I got recruited over there was, as most folks know, they have this long background of bottoms up individual people first. And I think what they wanted to do was change. AI was changing them into Notion is a place where people do work into a platform that works for them. And so it was this destination. It was this place where people write things down and it became a platform or the goal was make it into a platform where the company puts all of its context so that agents can use that context to do better work faster as opposed to people writing things down, circulating around, having meetings, sharing context. It needed to be more than a wiki and they were looking for a genuine repositioning. And typically what I do is, as Sydney said earlier, come in when companies are at some kind of inflection point.

(11:20):
So I think there were two big things. One, the narrative had to change to support what they wanted to do. You're not selling a better place to take your notes. You're selling a layer that makes the company's own knowledge usable by AI, different story, different value. Are you wasting different buyer? So the second part of that is a note-taking tool is an individual sale. One person adopts it, does their own work in it. There's a lot of Notion fans that they love Notion, they run their life on it. But a context platform for a business is only valuable if the whole team's knowledge is in it. The motion has to shift from selling to a person to selling to a team because the product only works at the teams in it. So the thing that I just said earlier about delivering that proof, if a whole team is using it and creating value before they ever talk to sales, you're not starting from scratch because that value is proven.

(12:13):
You're not persuading them through marketing artifacts that this thing is real. The repositioning and the go-to-market change are the same move. And so that was really the mandate that I was brought in to solve.

Jon Miller (12:25):
So you kind of got brought in under a strategic umbrella in some ways.

Lena Waters (12:31):
Exactly.You

Jon Miller (12:32):
Didn't have to earn it. Were you free there? You didn't have to report on MQLs or do anything to justify your budget because of that, or did you still have to do some of the basics?

Lena Waters (12:44):
Yeah, I mean, let's talk about MQLs for a second. I think everybody fights the same battle at both places, right? This sort of gets to comparative too from the research that you guys have done, this idea that MQLs are about individual people, right? It's a marketing qualified lead. When you switch over to, let's say an MQA, which arguably is better, a marketing qualified account, you need everybody there, which ties together this whole idea of why B2B is important. You don't kill the old metric, first of all. I think there's this idea of you can sell a theoretical idea to your C-suite. You can go to them, you can explain how marketing works, you can get really academic about the theory of it, and then you can get permission. Some folks do that, they're successful at that. I'm never a big proponent of that. I think you just do it without asking for permission and you show them proof.

(13:32):
So you run the new model, the MQA model alongside it for a couple quarters, and you let the data from the MQA kill the old MQL. If you go to sales and take that sort of shared MQL metric away before you've replaced it and that trust that that shared metric carried, I think you're going to lose credibility faster than having some bad MQLs. I think it's still a better metric, but I mean, I think you also have to ask, I mean it's a little theoretical here for a second, but what was the MQL actually measuring? I think it was really measuring content consumption. It was measuring did people read the white paper, sit through the webinar, download the guide, come to the booth? And we scored these MQLs based on how much they did it or how recently they did it or what the seniority is of the people who are doing it.

(14:16):
But it was really content absorption and then we called it intent to buy. But I would argue that that content all along was just persuasion and it wasn't really proof that something's happening and that there's a ceiling on that. And so what I was trying to do at Notion and at Grammarly for that matter is get people to touch the product as much as possible because it's the opposite of persuasion. It's proof. Somebody's using it, feels the impact. PLG companies naturally do that to individuals. If you can convince that PLG native company to really make that leap and to start evolving the product so that it is impactful for teams, you're buffing up your enterprise pipeline building motion right from the very beginning. And I'd argue that if I had a dollar, I'd give it to product and see if I could get a more team-like motion that is more load bearing than I would argue for a dollar put into say brand advertising.

(15:14):
When people say brand, a lot of times what they mean is that's sort of a code word for I'm going to rent someone's attention for a while while I'm spending money. And I think that that has shelf life on it and it goes away after a certain amount of time. You look at the competing billboards in San Francisco and argue is a slightly better message actually going to make a better impression? Does that survive after the billboard's gone versus a group of people within a company using a product to make an impact on their business and is it load bearing and what breaks when you take that away? I think it's much more useful. And so I think the surface of the argument has always been, is MQL dead? Is MQA better? Sure. But if you really unpack what you're trying to do, it's how do you get tangible proof within a group of people that your product is meaningful and load bearing to their company as opposed to persuading them that the idea is good and then them not having any practical experience with your product until they sign a contract.

Jon Miller (16:11):
Do you think that can apply to every company? Can every B2B company out there do a PLG motion or is it just for some?

Lena Waters (16:20):
I'd say it's not everyone should do PLG. I think what we need to do is stop thinking of PLG as a different revenue source or a different spot in the funnel or something that's only for one audience and start thinking about it as how wide can you open the front door to one buyer journey? So every little bit of the product that someone can adopt before they buy is a dependency that you don't have to manufacture later with a funnel. So there's a whole range of how wide you can open it. It doesn't have to be free product or nothing. I think one way is can you provide an open API key? Can you provide a usage-based tier? Can you do something where someone can start building the minute that they have an idea? And even if you have a heavy complex product, a narrower version of that, even if you can't open up your front door and somebody can't just come in right off the website, financial services, security, something like that, instead of running a sales demo with an SC where you're putting on this big demonstration about how this would work and trying to persuade them, do something to give them proof.

(17:18):
Could you do a hands-on proof of concept that the customer runs themselves? Go in with a squad of free professional services to help them get going. Notion did a really great job of doing these sort of integration days on site physically with a customer where they'd set up as much as they could and connect as much data as they could. You don't want these people watching, you want them building. And if there's some sort of hard limit to your product in particular about why a company can't do that, I think find a creative way. I think it's always going to be better than just the show and tell that we've been used to.

Sydney Sloan (17:50):
Which is really marketing to the user who sometimes is the buyer and sometimes isn't the buyer. And so you still have to run both motions in that model ultimately when it comes down to who's making that decision. So I think that's really interesting. And that's one of the things when I'm doing advisory work, I'm like, who are we building this campaign for? Who do you want to know your brand more than in anyone else? Do you want it to be the user or do you want it to be the buyer? And I'm curious if going back to the brand question for a minute, because that's a pretty controversial thing that you said, that you would rather take a dollar brand and put it into product experience instead of brand, yet you've worked at some of the most notable brands in B2B, DocuSign, Grammarly, Notion, all very well established, fantastic brands.

(18:42):
And one of the things that happens is marketers struggle to make the case in financial terms of investing in brand. So if you're going to give that dollar to product, how do you still think then or what is the way that you prove that a brand investment is still necessary?

Lena Waters (19:04):
Sure, sure. Yeah. And I think to my point of handing off the next dollar is sort of a forced choice. I mean, you're making decisions on two levels. There's the company hat of should the next dollar go to marketing program budget or should it go to hire 10 more salespeople? Should it go to improving the product experience so that more of the customers that I'm eventually going to have to create a funnel out of anyways have hands-on experience and belief and dependency on the product before they get to me? And is my funnel going to be more efficient? So I said that as if it's a forced choice. You're always doing these things though with your other C-suite arm in arm and going, imagine a world where a customer comes in and instead of us having to convince them of X, they already believe it because we've created this experience.

(19:51):
And in order for that to happen, what if when they came to the website, instead of sending them to a lead gen form or hoping that they go to a free trial and trying to optimize for a number of free trials, which is yet just another vanity metric the same way that white paper downloads are, what if we actually had some real hard dependency where we're making an impact in their company before they have to give us a dollar? And you form these things with these hypothetical choices that both of you getting together are allowed to do. You could work with your CRO and envision a world where product demos are done differently because you both want a different outcome. You could work with a product team and talk about a different in-product experience for them and it doesn't just have to be about who gets the dollar.

(20:29):
So I'm not saying as an executive be naive about it and just hand all your budget away. That's one thing. To your question about how do you think about brand spend versus a different kind? And my point that it's not that I prefer some kind of spend over others, that sometimes brand spend is kind of rented attention. So if I'm really trying to make a financial case during annual planning or during a real conversation with the CFO or maybe with the board, the other kind of brand that you spend on is some sort of compounding evidence. You take a big consumer brand like a Coca-Cola or a Ford Motor company, they have a line item in their balance sheet where they put a numerical value on the value of the brand. And I think we take it for granted that consumer companies do this, but we also take it for granted that B2B companies don't.

(21:15):
I would push on that with a CFO and go, look, we all look at big brands like a Salesforce and we know that their brand is worth something, but then we think that for us it doesn't matter. And I don't think that's fair to sort of have that both ways and that's a conversation that deserves to be had. So if you think about proprietary data, original research, what kinds of stories do you want customers saying to other people about what your brand and company and products has impact on them, a community that talks about you in public, you have to have these compounding evidences that keep working after you stop feeding them, unlike a brand campaign that sort of begins and ends. With the CFO in particular, I think that's the whole argument. Community compounds and awareness evaporates. So you don't ever ask them to fund brand.

(22:02):
You show them that, look, we've got this asset on the books that keeps returning after you stop paying attention to it. And maybe you're top and to the right in Forrester or Gartner, or maybe your community is million strong and you have serious investment into it, or maybe you have customer advocates that will hop on stage at a moment's notice and just sing your praises. Sydney, I mean, you said this in the B2B CMO report, right? You never ask your CMO for brand budget. First of all, you have to do your own work, right? You find that 20% of the demand spend that nobody's going to care if it went missing or is underspent anyways and you redirect it. It's a little bit like the MQL/MQA. You don't ask anyone's permission to run MQA, you just start doing it and then you bring evidence that it's working.

(22:40):
These are complex answers because you're constantly managing your mandate and your remit and your budget like it's a portfolio and you have to rebalance it like you would your own personal financial portfolio. Some days some things work and some things don't, and you have to make sacrifices for them. But I think that what underlies all of this is these are difficult conversations and I think you need to bring them to the C-suite and have them and have solutions, but be open to them and show them the red, not always show them the green. And I think if you can have those frank conversations, then you know you've got a great leadership team and if you can't have those conversations, I mean maybe that's a different story.

Jon Miller (23:14):
Bringing the problems is definitely one of the lessons that came up in our research. A little earlier you said that brand is also kind of how people talk about you and you led inflections on that. At Grammarly, you sort of had to move from being this little widget that checks your grammar to being a content tool. Notion, you already talked about moving from note taking to being context. And I'm going to be telling the story, how did you measure and show to the C-suite that you were succeeding in changing how people talked about you?

Lena Waters (23:48):
At Notion in particular, we use Qualtrics, which I'm sure the audience is familiar with, and we got really specific. After I got there, we learned that we had committed to doing a big brand spend right when I got there. And I think in the first six weeks we drastically changed the messaging very publicly and got it out as soon as possible. And that was something that I had discussed on the way in, so we were able to do it really fast. And we got some great data out of Qualtrics in the trailing quarter that led us to say, hold on a second, we need to be spending a lot more money with Qualtrics. And that actually became part of the investment. So we took program spend from one place and actually put it into measurement, which was a pretty serious move. But we made it global and we extended the kinds and amounts of questions that we were asking to get a better picture.

(24:34):
And then really roughly just kind of mapped out the year and said, okay, if we do the big user conference in San Francisco, if we take it global, if we expand the number of events, if we drastically change the narrative and do a major billboard campaign and do a lot of out of home digital and billboards in a lot of different places for these reasons with these segments in these places, what do we think will happen? And then we tried to show it in the data and some quarters it worked and some quarters it didn't. And that was one of the things that we used. The anecdotal data though that you get back from sales about what the conversation's like in the room and do people believe things before they get there, you can't underestimate that kind of thing. So I would say just take a very practical view of the top three to five things that people in the company really care about.

(25:19):
And some of those things should be data that marketing owns and some of those things need to be anecdotal things you go get from other people. What are people saying about us? What are other founders saying? What are customers saying? Is sales having a more difficult or an easier time? And use those things together. And then you just admit that it's not going to be a perfect science, but you have a portfolio of proof points that you can use. And most C-suites are pretty practical about taking a group of imperfect and perfect data together and helping understand the story as long as you're the one to shepherd it along.

Sydney Sloan (25:51):
This also then leads into another one of the imperatives that's important. And you talked about getting the trust of the C-suite and being transparent and showing the red. And so when it comes, and you've said this before, that CMOs have to understand the CEO's view on marketing, even if it differs from the CMO's job. So as you go in or as a CMO goes in, what questions would you recommend they ask early to figure out what the CEO's real expectations of marketing are? Maybe give us an example from coming into Notion to help you not just be the execution function.

Lena Waters (26:36):
Yeah. I'm advising right now, so maybe there's a couple things that I can share that I've learned from both advising and as the CMO, but that's a lot of what I'm actually doing right now with CEOsday-to-day. It's help them get honest about what they're really asking marketing to do. A lot of CEOs haven't really articulated it to themselves yet. And so there's three questions that I try and surface really quickly. I will ask the CEO to rank unprompted, does building the demand engine or does building the category narrative matter more to you this year? Now, it's an artificial force choice, but that one ranking will tell you what the job actually is or what they think it is regardless of what they've written down in the job description or what they told the recruiter when they're looking for a CMO. And half the time the CEO will learn something about their own priorities.

(27:20):
They'll either reject the forced choice or they'll pick one and they'll give you a reason, but it starts that conversation that makes them think about what do they believe if they were forced. And it's a theoretical exercise, but it's really illuminating. The second thing is, I tell every CMO to ask this and I ask this, ask the question, how involved does the CEO want to be involved in marketing day to day? And then just stop talking and see what they say. And it's kind of amazing where everybody wants to know this and nobody feels like they can ask the question, you just have to say it. Asking it plainly is the most confident thing that you can do in that room. And the answer determines whether or not the CMO is being set up to lead or being given permission to execute. And the third thing is I test where the CEO's marketing conviction comes from.

(28:03):
Is it theirs or is it borrowed? Have they been in companies where they have seen great go-to-market work? Have they been in companies where they've seen it fail because both are important? Or is this something that somebody else told them where they're in their founder network and this is what everybody's saying that they're doing? People say a lot of things on X these days or they heard it from a podcast or their board thinks that they should do it. But I'm asking them what have they personally seen that succeeded and why do they think that it succeeded? And if that's a difficult conversation, then you kind of have to go back to question number one, which is how are you ranking your priorities here? And I think if you cycle through these questions enough times, you start to understand what the CEO's point of view is.

(28:43):
And you're not looking for a gotcha, you're looking for understanding on both sides so that you have a similar frame of reference that you can move forward from. If someone else wrote the positioning before the CMO arrives, now this is for earlier companies maybe, then maybe that CMO wasn't hired to lead marketing, they were hired to run it. Founders or CEOs or some sort of team, there's always a narrative. There's a story. There's a why do we deserve to exist as a company? What product value do we have? But there's a narrative around a category, messaging, a story that hangs together that they're expecting the CMO to carry. And if it's already built and it's untouchable and you can't really have a conversation about it, then that's a tell that the company thinks that marketing's an execution function and just hasn't been staffed yet. If you want a real marketing leader, you don't really hand them a finished narrative and then say you're empowered.

(29:38):
So for CMOs, I would say notice who wrote the story before you got there and is it a collaborative effort to continue to make it better? Because it's not going to survive beyond a year or two, it's going to have to grow. And who's going to do that? Is it you? Is it somebody else? And marketing's a participation sport in a lot of cases. Everybody has an opinion about what it is and what it should do, and you should welcome all input, but that is a little bit of a litmus test. To be able to tell what kind of position you're being hired for.

Sydney Sloan (30:04):
I think that's interesting. And I still believe that the CEO needs to write the vision or the founder, the five-year vision, but how that translates into current positioning, what you want to be known for, how you talk about it, who is part of the amplification process. It's a lot easier to execute if you're participant in the conversation versus the executor of somebody else's strategic plan. Not interesting to me personally. Yeah, exactly. No, no. Jon's had to wear both those hats too.

Lena Waters (30:39):
And depending on what your personality is and the role and the company and what year it is and how you like to work, I mean, those things all matter. I'm never precious about I have to be the one and I have the only good idea. I mean, a good idea should win on its own merits. So I mean, taking that as read, this does go back though to the second question, which is how involved does the CEO want to be involved in marketing day-to-day? Because if it's not enough, then it's something that somebody else has to go and do. And like you said, they need to own the vision. I mean, your best salesperson in the company is the CEO. They're the person with the narrative that they're putting out on social media. They're the people getting on stage. They're talking to the board, maybe they're going out for funding.

(31:16):
They need to bleed that story. That's really important. You want them involved, but if they're going to come in and copy edit the homepage of the website every week with you hand in hand, that might get a little trickier. And there's no bad job to accept. There's no wrong team to work with. It's a team effort and you have to mesh, but you do need to know before you get in there what it's going to be because then you know what kind of value that you're prepared to add.

Jon Miller (31:41):
Well, maybe there's no true wrong job, but there's certainly wrong jobs for certain CMOs. And I have talked to CMOs who are in the wrong one, at least for them. And as much as I'd love the advice to be, okay, just follow the five principles from our research and it's going to work out. Sometimes the answer is this isn't the wrong team for you, I think.

Lena Waters (32:03):
Yeah, it just depends. And the thing is too, is that nobody wakes up in the morning and says, "I'm just going to drive this company to the ground today. It was through bad decision making." Everyone's got good intent when they show up in these things, but teams either mesh or they don't. And I think this is where you have the power to ask the hardest questions before you ever join. And ideally, you retain that courage when you're still in the seat. Your job is to ask the hard question, that's why you have a C in front of your title. That is the job. Yes, it's difficult, but you don't have to win every fight. And there may be things that you can kick down the road and go, "I'm going to set up a conversation where I can tackle this next quarter." Not everything has to be a do or die kind of moment, but I do find that this conversation that we're having, sometimes CMOs will have this conversation with each other and then you ask them point blank, are you having this conversation internally?

(32:52):
And they don't or they can't or they won't. Working at a company is a participation sport. You got to get all the kids in the pool and you have to say the hard thing. I think it's better to say the hard thing and have it not work out than to just sit on it and to always think maybe I left something on the table and I could have done more there, but I never asked the hard question. Life is short. Say it.

Jon Miller (33:11):
I think that's good advice.

Sydney Sloan (33:13):
So we've talked a lot about how you've come in to change the narrative, how to think about the brand investment versus the product experience. One of the other biggest things that's impacting us as leaders today is how we're redesigning our teams in this new AI oriented world and how do we continue to hit today's targets while also re-architecting for the future? So if we were to put this in a stop, start, continue or some kind of redesign, what would you recommend or what are you recommending to CMOs right now to stop doing or to redesign or to automate when thinking about building the AI native team of the future?

Lena Waters (33:58):
I love this question. There's a lot of narrative out there right now about it being a talent problem. The thing I keep getting asked is how do I build the team?What's the perfect org chart? I don't think it's a talent problem. I think it's a permissions problem. I don't think it's the org chart that's the issue. I think it's data access, which sounds really boring, but I think it's true. We're asking marketing people to rebuild everything from the ground up, AI native, go back to first principles, but we're not really giving them permission to touch the data. So I think things are being framed as hire orchestrators and be generalists and upskill the team. And that's real, but that's downstream from that. So I'd say if your marketers can't get to the data, and I'm talking like, do they have read, write permission to the CRM?

(34:40):
How many days does it take and how many departments do they have to go through to get permission for product usage data or something that they have to go through the DS team for? I mean, that's great to have partners and assets, but a lot of this just turns out to be blockage. You should be able to have an idea and execute it in the same day. And if you can't, I'd say you have a permissions problem regardless of what your team looks like. No amount of AI literacy is going to matter if you don't have data permission. So that's the start. I think the stop is I would stop organizing teams by channel. And I know we've said generalists are important, but I have a more specific reason about this. And it is a natural way in the past to build email, social events, web and have an owner.

(35:17):
But I think what you're quietly teaching your team to do is to optimize their own channel and to defend it and then to debate their impact with the owner of the next channel further down the customer journey. And the way I like to help the team evolve out of that is to make every team metric ladder up to one shared department metric so that everyone's rowing towards the same sort of outcome instead of just protecting their lane. And if somebody says something like, "Well, my work doesn't really move that number," I would take that as a coaching moment, not as a fight because usually it does help. It's just hard to make that connection and helping them see that the line from their work to the thing that really matters is the job. A marketing team has to be one team driving the business. They can't be a collection of excellent channels.

(36:02):
The thing that I would maybe automate under continue, I would say is that's where the repetitive production work happens. So if the time between idea and impact is this drawn out process, and I don't really care if humans are doing it or if the AI is doing it, but if it's like the brief, the variance, the first drafts, the reporting, I think one thing that companies are really big on now that is refreshing to see is I'd rather see something live out in the market and us getting data on whether or not it's working or not than seeing 14 different versions of drafts where we come to this long, painful road to consensus as opposed to doing something edgy and putting it out there. The thing is you're going to do marketing and some of your customers are going to hate it and they're going to say bad things about you on social media.

(36:47):
That's going to happen no matter what you do and how many briefs you've been through. So you might as well cut down the time that it takes to do it and put out 14 variations and see which one works than to keep them all on the cutting room floor. And I know that that's something that everybody goes, "Yeah, that's really true. It's remarkable how few teams actually do that." So I would say push it out. Don't really ask for it. Just get it out there and then see what works and that's going to answer your question better than any measurement would.

Sydney Sloan (37:12):
As you get to at scale, I remember my days at Adobe used to complain that 80% of our time was internal meetings and planning and we only executed 20% of the time. And what would it actually mean to reverse those two things? And I think that today that is an opportunity for companies to really reshape that, give empowerment, permission, set up the metrics, the measurements in order to be able to make those decisions quickly. So you still have to have that infrastructure in place, but we just have to transform faster. There's no waiting.

Lena Waters (37:49):
If one of the real tangible benefits today of AI is that you can produce 20 things in the amount of time that it took you to produce one, well then what are we really saying? Now I have 20 options and I have to have 10 times as many meetings to figure out which one we're going to do so that everybody's happy with it. That's ridiculous. That's the old structure. So if that's true, then get them out there and let the audience decide because you're never going to know. The only thing you're arguing, if you're still arguing about political capital within a company, then you haven't really changed anything. Now you just have more to choose from. So I think it behooves you to ask, have we actually made a fundamental change and does it scare me 10%? And if it's not, probably not doing the right thing.

Jon Miller (38:28):
First of all, I love the little 10% piece you threw in the end there. That's something I use with my team a lot. I heard a theme through everything you sort of talked to here a little bit, which is kind of a lack of waiting for permission. You've often said just like, just go do it. Just go start and prove that it works and all that kind of thing. It feels like that's definitely a theme in how you're applying to your marketing and I'm just wondering if that also applies to your life.

Lena Waters (38:51):
Yeah. I mean, one time the CEO took me to his office and said, "I need you to move to this island in the Caribbean and run this offshore part of our business." And I didn't know where the island was and had never been there and said, "Sure." And gave up my Canadian residency for a couple years and went down there and did it. I just think that, I don't know, would you rather go to a new restaurant that you've never been to before and have an exciting experience and not really enjoy it? Or would you rather go to your favorite restaurant you've been to a thousand times and know that you're going to love it? And I think that's just a personal choice for everybody. But someone's buying our time and our attention away from our families and loved ones to go and do a job.

(39:30):
And I don't want to get home at the end of the day and go, I kind of mediocred that one. So I just think leave it on the field because you're going to regret more not doing it than you're going to regret, oh, I really said something stupid. I mean, people don't really stick their neck out that much. Even something that's 10% risky, it's really not that bad. Your sense of survival is going to protect you. I think the best position that you can be in is to be in a spot where you feel like you can take risks. And if you ask an executive, that's what they want. Everybody wants to fail fast and push hard and grow faster. And so take them at their word. And you know what? Sometimes it works out and sometimes it doesn't, but I don't think you're going to regret it.

Jon Miller (40:08):
Well, that is awesome advice to end on. Thank you. Thank you so much. Is there anybody you want to give a shout out to, anybody who helped you get to where you are in your career today that is worth a mention?

Lena Waters (40:23):
Okay. Well, maybe keeping on this theme, Joanne, of no fear and what that means. I think one, I have to give a shout out to my friend Scott Olrich. He brought me to both Responsys and to DocuSign. He's the reason I made the jump from running a function to leading as an executive. I think his gift was space. I'd bring him a hard problem and he'd hand it back to me with enough trust that I had to grow into figuring out how to solve it. And he also modeled the thing that it takes a while to internalize as a leader, which is you don't have to be the person who knows and solves everything. Your job is to find minds that are stronger than yours and to build a team around them. And then I think maybe my second thank you isn't to a person, but it's probably to every person who's been on my marketing teams over the last 20 years.

(41:06):
Go to market has never stopped changing and anyone who's worked with me knows that I do take risks and I will say maybe the hard thing, ideally to get us to a better understanding, not to just be the one who said it or to start a fight, but they came with me anyways and I think that's the part that I'm really grateful to them for.

Sydney Sloan (41:23):
Oh, this has been such a great, great session. I knew it would be because you're always on point, not afraid to answer the question in the way that you truly believe and are always learning. And I think Jon already kind of picked up on those themes. It's leading with confidence, taking risks, and really understanding the relationship between the user and how to invest in user experience and translating that also to revenue and the impact that it can make and connecting those dots. That's what I think listeners would've learned from this session. If you are listening still and have written a page full of notes like I have and want more content like this, you can go over to the B2Bcmoproject.com where we have all our podcasts, original research, best practice documents. If you're an enterprise CMO, join our community and have opportunities to meet with other smart CMOs like Lena.

(42:24):
I want to thank you. I want to congratulate you for being on the top 100. I want to thank you for being one of our founding members, Lena. The other part of this is we learn and grow together as a group, and so we're so grateful to have such incredible CMOs contributing their time and effort. Thanks everybody for listening and we'll see you on the next one. Have a good day.

Jon Miller (42:43):
Thanks for listening to the B2B CMO Podcast. Head on over to B2Bcmoproject.com for more episodes, plus the latest research and framework CMOs need, not just to survive, but actually thrive as AI and the new playbook reshape how we go to market. And if this episode sparks something for you, please follow the show, leave a rating and share it with a marketing leader who could use a little inspiration. Special thanks to our wonderful partners, OneMind, 2X, Cheq, Demandbase, G2, Goldcast, LinkedIn, Phave, Sendoso, and Webflow for making this podcast possible. Until next time, be safe out there.