Our Favorite CMO Insights of 2025 | Krystina Rubino

Hi, and welcome to Growth Talks, where we dive deep into the world of growth and marketing with industry leaders. I'm Christina Rubino, the General Manager of Offline at Right Side Up, and your host. Today, we've put together a special highlight reel of CMO insights from conversations we've had over the past year with marketing leaders who are rethinking what it takes to build brands that people trust and love. You'll hear how they approach their craft, blending brand and performance, building momentum inside their teams, going truly AI native, leading with empathy, and forging deeper, more authentic customer relationships.

So whether you're a founder, CMO, or marketer looking for new strategies, this episode has something for you. Up first, Tamara Mendelsohn, former CMO of Eventbrite, breaks down the false divide between brand and performance and reminds marketers that growth accelerates when both teams move together. What are some early measurement mistakes you see or have seen made early on that could limit growth later. Yeah, I think it's focusing too much on the lagging indicators, which are your bottom of funnel metrics.

I think they're the metrics that CFOs are often the most comfortable with. They're the easiest to explain. And so they become kind of a crutch, but they are absolutely lagging indicators. So people obsess too much over what your CAC numbers are and lowering that.

I think LTV is another one that you probably don't want to overly focus on too early. There are these mid-funnel metrics that are important to look at, which is branded click-through rates. That tells you, are you reaching the right audience? Is the content resonating?

Landing page conversion rates, direct traffic, growth, first-party content engagement. So engagement with your social, engagement with email signups, return visits, that content, other content consumption, depending on your business. And I think it's like you actually need all three of those buckets to understand the health of your growth, your growth engine. I'm not just going to say your brand because your brand is growth.

But to understand the health of your growth engine, you need to triangulate those leading indicators that we talked about at the beginning, the brand health. You need to pair that with these sort of mid funnel metrics. And then also those lagging indicators, they're not like we shouldn't be allergic to them either. But I think the mistake is looking just at that group of metrics can really obfuscate bigger problems that are coming down the pipe, right?

If you are not filling the top of your funnel with new consumers that are becoming aware of your product, with new consumers that are now starting to consider it and are building some intent towards it, then at the bottom of the funnel, you're going to scoop up all the direct response traffic, all the people that have immediate intent. and then there's going to be no one left, right? At Eventbrite, we always used to say that, you know, the lowest cost acquisition channel is customers who we've already engaged with.

How do we re-engage them? How do we get them to come back? What is holding them back from coming back? And do we deeply understand that in a way, systematically eliminating those barriers and those friction points, right?

And so thinking holistically about your audience, where they are, how to reach them, how to engage them is really the goal of marketing. And I think that I'd much rather have that conversation in a marketing strategy discussion than should we do brand or should we do performance? Should we do awareness or should we do direct response, lower funnel marketing? It's not a dichotomy.

It's not an either or. These things work together. Next we hear from Jaleh Bisharat fractional CMO for Skillshare on balancing the day demands of marketing with the bigger mandate to drive momentum and set the company up for long success I think about the differences between sort of VPs and CMOs. I think about that ability to zoom out, look strategically at the business, and identify those one or very few levers that can change the enterprise value.

Very few people can do that, and directors don't typically do that, VPs sometimes, But the CMO role, I think, is kind of uniquely positioned to do that, a good CMO. You know, that's a really interesting observation. I hadn't quite thought of it that way, but I think you're right. Also, a lesson I learned over the, honestly, quite recently is I used to think of CMO as chief marketing officer.

Like, my job is marketing. That open table example notwithstanding. And I've come to realize that actually the best thing you can do is make sure that your marketing house is in order, but help the rest of the business. Think like the CEO as much as you can and as appropriate, because now here's a Skillshare example.

Step into Skillshare. Skillshare is heavily weighted towards marketing, customer acquisition and so on. Actually realized we might be too weighted towards marketing. It's an odd thing to say, but we actually reallocated some dollars from marketing to product based on the observation and having spoken to customers and the realization that without some product and product design refresh, marketing was not spending money as wisely as we would be if we had, you know, investing in product and product design.

Now, Caitlin Watson, the CMO at Talkspace, invites us to move past AI as a feature and step into an AI native mindset, one that reimagines how we create, connect, and scale brands. I would love to talk about AI for a moment. I'm sure we'll come back to it at a few points in this conversation. Just to tee up your thoughts provocatively, can't AI do this?

Can't AI, you know, rebrand and play that role? Maybe more practically and realistically, like, what is your view on AI more generally and in application to this particular area? How would you advise companies to use it or not use it? Yeah, it's a good question.

I mean, this was even the Talkspace rebrand at this point was really before people were thinking about AI in the way that we do now. And I've been kind of inundated, I have to say, with AI dinners, AI roundtables, you know, AI talks. I could probably go to something almost every day of the week and get together with a group of CMOs who are talking about all things AI. And I've been going to some of them and I would say the conversations have been evolving.

And I've generally seen the sentiment around creative being, there aren't a lot of creative tools yet that are completely set it and forget it. Will they get there? Probably. It also depends on the type of creative.

If it's, you just need to create a postcard for something really quickly and get it out of the door. Maybe. you know, a lot of the success around user generated content and influencer marketing, which I know we'll probably talk about as well. I think AI is really good for maybe like mashups and creating different iterations, but not necessarily out of the box.

So from a, from like a rebrand perspective, prompts developed to give, you know, put ideas out there. And I think this is where agencies probably are starting to see much better margins maybe than they used to, used to It just the ability to you know put all the prompts out there and let everything kind of be creative but you still need to have that And we say the same thing by the way with AI therapy because AI therapy is a huge topic right now at Talkspace That human emotion EQ sentiment is still a big part of refining a lot of the output from AI, especially if it's an asset that you're creating that's like there for the long haul, because it has to be evaluated against so many custom variables and how you might use it.

But I think it's a great jumping off point. Absolutely. Up next, Aaron Magnus, the CMO at Full Glass Wine Company, explains why modern marketing leadership means knowing the business better than anyone, setting clear expectations, and giving your team room to grow. In terms of leadership, you led marketing teams across different industries and also different company stages.

And as your careers evolved, how have you found that you've adapted your leadership style and what core principles have remained the foundation of your approach? Yeah, I think, you know, as a leader, you definitely have to flex different muscles than what you're normally used to when you're an individual contributor and coming up and you're trying to be an expert in every little thing. I think, you know, the main thing when you're in a leadership role is one, attract amazing talent.

So what's the way you can do that? But then two, once you have amazing talent, how can you be really clear on what the expectations are? How can you be very transparent around, you know, what you're really looking for and why and why it's important and why it's important right now? You know, what does success look like and what are the goals that you're expecting?

And then outside of that, like, how do you get out of the way? You know, I think so when you talk about how have you, you know, sort of shifted over the years, I mean, I've been doing this a long time. So I think when you're starting out and really just trying to dig in on every little aspect and then as you continue on, you realize the importance of understanding the story and the narrative and really adjusting that as opposed to this point for that versus that point. But at the same time, you probably really got to know the business better than anyone else through the entire organization.

So what's the pulse of the business, the data, all this stuff that really matters to run it? How do you spend more time focusing on that as opposed to, should I be flipping this lever a little bit 10 degrees higher or down? So if that helps, that's sort of how I think about things. More great advice from Kate Lockhead, CMO, who shares how leading with empathy will create more authentic campaigns that will help deepen your connection with customers.

Are there any examples that you can think of like specific campaigns or strategies that ultimately like either unexpectedly outperformed or maybe ones that you were like, these are gonna crush and then they fell apart? Yes and yes. Let's see. Outperformance, I think, was a campaign that just reinforced my belief that, again, everyone is human and you have to have empathy.

And that was a mental health campaign that we did at Junk Cloud. So IT professionals like finance, I mean, like everybody, right? Like they just receive a ton of shit all day long, right? Like people complaining, I can't get in.

I can't da-da-da-da-da. When I was at JumpCloud, it was during COVID. And, you know, there was this massive nightmare for IT where everybody's like, okay, everybody go work from home. And like all of a sudden you have, you know, your normal problems times every single person's home configuration, right?

And people are calling them about like their routers and blah, blah, blah. you know, like everybody's complaining as though it's IT's problem. And so listening to, we had gong, which was amazing, right? Like the more and more you listen to calls and you hear these guys just struggling.

And I happened to be a strong believer in meditation and a meditator. And at that time I was probably four or five years into my journey And so maybe at like the peak of my best practice you know I thinking like this is what IT guys need But they really do like they a lot of IT teams are ex So they have PTSD is rampant in the community. And so anyway, we ran this whole campaign around the importance of mental health. And it, you know, the broader topic really was around how to manage work and set boundaries.

And at the same time, like, how do you become more efficient in your job? you know what I mean? So there was a tie-in to the product further down, but it was, I mean, for years after we would get people in who were like the first time I ever, you know, encountered you guys was through that ebook or through that webinar, you know, I replayed it with the meditation the guy did on the thing. So that was probably the most outperforming.

Like I really, we really had built that as a brand campaign exclusively. Right. So back to, you know, how did you allocate your budget? I was like, this is brand awareness.

this isn't going to generate a lot of pipeline. But in the end, it really did. It influenced a ton of pipeline because it built brand trust and that's, you know, trumps everything. So that was probably my biggest success.

And last but not least, Matt Goering, fractional CMO, shares how clear data definitions and knowing LTR versus LTV help teams stay aligned, catch real issues, and focus on the metrics that matter. I would love to go on a little bit of a side tangent and just drill in on what you just said they thought that they were measuring ltv but they're actually managing it to ltr uh would you expand on that for the audience because i think this is a great and major point that a lot of a lot of marketers miss so yeah okay so i'll go to two things first thing for me is like one of the things i do going in when i do that kind of metrics review and everything is just data definitions of like what does a new customer mean what does a repeat like all of these things what happens if somebody buys twice in the same month where does it get like I like to have that because it helps when we're explaining things or we're going like, hey, we know to go solve this issue.

It also helps you dig into the actual problem when it happens. So the LTV, LTR thing, lifetime revenue versus lifetime value. Lifetime value is your gross margin. You know, it's OK.

And so there's a number of factors that go into it. I typically use a three year horizon. So you take how much revenue you're going to generate over those three years. But it's not that's LTR.

then you need to take in like your gross margin. So what are the actual costs? So if you're at a 50% margin business and your customer's generating $2,000 in those three years, your LTV is a thousand, you know, it's not 2000. So a lot of times brands will get into problems where they think when you get into that, like LTV to CAC targets of, you know, typically like a series B, series A, series B, you're trying to get to three in the consumer space.

You know, if you're measuring revenue, now you're actually at one and a half. So it's, it's one of those things that I feel I've heard less errors in it more recently. Like in the last few years, I feel like enough people have like, I don't know, Googled it or now chats telling them, you know, this is for Gemini, you know, this is what it means. But thankfully when I looked at any AI stuff, they haven't given the wrong definition.

Thanks for joining us on this episode of Growth Talks. We hope you found our discussion insightful and fun. Don't forget to like, comment, and subscribe to our channel for more valuable content. And if you're excited and ready to start up leveling your growth strategies and execution, Right Side Up has you covered.

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