On the Edge

Stephen Brown (00:01.39)
Welcome to On The Edge brought to you by Elite Sales Edge with your host, Stephen Brown. In the series, Getting to Know Your CXOs, we'll be diving deep into conversations with various C -level executives. We'll explore the formidable challenges they encounter, the critical decisions they make, and the lessons that have left a lasting impact on them. Sit back and prepare to gain some insightful knowledge from the leaders who shape the business world.

Stephen Brown (00:37.838)
Welcome to On the Edge. I'm your host, Stephen Brown, and this is another episode of Getting to Know Your CXOs. Today our guest is Wendy Kaceras. Wendy is a 30 -year marketing executive specializing in B2B enterprise software and cloud -native applications. She has held CMO jobs at leading IoT companies such as Echelon, Ilon Networks, K, and Insigo. She was also the former worldwide head of enterprise marketing at Amazon Web Services.

Wendy's experience spans both the public and privately held companies, managing teams across corporate marketing, product marketing, growth marketing, and channels. Wendy, we're so glad to have you this show. Welcome to On the Edge. Well, thank you so much, Stephen. I'm excited to be here and be able to join you this afternoon. Awesome. Wendy, why don't you tell the audience a little bit about yourself? I gave them the formals. Why don't you give them the informals?

Yeah, absolutely. So I appreciate being here really anxious for our discussion. Like you said, I've had a pretty tenured career in marketing over spans over 30 years. So I've been doing this for a very long time. And the majority of that has been out in Silicon Valley. So I'm out in the Bay Area, been here about 28 years.

And most of that time I've played CMO roles for as you mentioned high -tech companies, but about three years ago I actually left corporate America and I've been playing fractional CMO roles and I do this for PE backed firms that typically have Companies in their portfolio that are in two different stages So the first stage is a company that may be in a turnaround situation so they need somebody who is pretty experienced who can come in and

quickly assess the team, identify gaps, put in processes and procedures to help turn that around. And the second is, I would say, just the exact opposite. It's really, you know, a PE company has a high growth company in their portfolio and they need an experienced leader who can come in and really help them scale and capture that market opportunity. So that's when I come in and we very quickly...

Stephen Brown (02:50.222)
assess the team, we put in place new, new MarTech stacks, we hire, we build marketing strategies that are international that help them expand. And so that's what I've been doing for about the past three years. And it's really been, it's been an exciting time. Awesome. Well, let's get right into it. Let's talk about being a CMO. So if you were to give advice to an up and coming person that was

taking on their first role as a CMO, what would you advise that person to do in the first 30 to 60, 90 days to make sure they get off on the right foot? Yeah, good question. So I think the first thing I would say, Stephen, is I wouldn't necessarily do anything in the first 30 days. And by that, I mean make any major changes. I think the most important thing that an incoming C -level executive can do is to listen and to observe. And...

understand really what's taking place and why those things have been taking place in the way that they are. So I wouldn't recommend implementing any changes in the first 30 days, unless of course you're in a turnaround position where time is the essence. So what I typically do when I come on board is I assess the talent of the team. I believe very strongly that there are distinct disciplines within marketing. So...

Just like engineering where you have software engineers and hardware engineers, those skill sets don't necessarily translate. It's the same is true in the marketing world. So you may have somebody who specializes in growth marketing. That's not going to be your person who should be, you know, first and foremost running your PR strategy. So I'll take a look at what the team, what's in place, identify where there's strengths, maybe where there's overlaps or where there's gaps.

And then I would implement the right team structure so that everybody has a role to play. They can play their role and we can act as kind of one holistic team. The next thing that I would do is look at what the marketing strategies and plans that are in place. And I come from a very data centric world. I use data as much as I possibly can.

Stephen Brown (05:02.062)
So I took to look at what's the impact of those marketing strategies and plans? What's the ROI on those? Which ones are performing well? Which ones aren't? And then we begin to build around that. Awesome. Well, thank you for that. And one constant theme that has jumped out across all the senior executives that I've talked to, such as like yourself, is listening. And, you know, kind of coming in, you know, I'm the new sheriff in town kicking the doors in, you know, that's really,

that's really not a recipe for success. And to a person, they've been like, you know, you learn a lot in that first 30 days, particularly if you can get people to open up. If you're within the organization and you're promoted into the role, that has a different set of challenges that come with it, also some opportunities. And if you're brand new to the opportunity, it's a whole different dynamic. So...

I think your advice is wise, I mean, to listen, learn, and then implement. I think people in the company would respond a heck of a lot better than that, than they would if you just dictated the whole thing. Yeah, absolutely. I've never seen that first approach of the new sheriff and count ever working out well for anybody. Although, unfortunately, I have seen it happen in...

both large and smaller organizations. So it's not uncommon, but I've just never seen it turn out well. Yeah, me either. You know, so you mentioned to, you mentioned your people, different skill sets, you know, different people play different roles. They bring different things to the team. That leads me into the next question I have for you, which is the team, you know, tell me about your idea of what makes good leadership and what do you...

What do you, how do you go about building a team and assessing a team? So I think about, you know, the leaders that have inspired me and, you know, who I would want to go and work with time and time again. And I think there's, you know, I think the thing that pops out for me most is that those leaders lead by example. You know, I think about, you know, one of the CEOs I worked for that I just felt like I was continually learning.

Stephen Brown (07:23.79)
I'd come in and it would be an earnings call and there'd be something new that was going on or there'd be some international expansion or some &A. And they were always very active, an active part of those processes. So I think first and foremost, good leaders lead by example. And so when I build my teams, I try to make sure that I would never ask a member of my team to do something that I had A, never done before or B, was not willing to. And...

You know, I think what that begins to build is outside of respect, you know, for that is trust. And I think good leaders build trust amongst the teams and their colleagues. And part of that trust building is providing, you know, proving that you're capable of not just managing the group, but you're knowledgeable about the subject matter expertise and you can get there and demonstrate that you can pull your weight of the team as well.

And so, while you've got their backs, you're also a part of that team and an active member in participation of the group success.

Stephen Brown (08:31.47)
Yeah, that's, I mean, I agree with you. It's, it's, you know, it's funny. You don't necessarily see it happening when it's happening, but you know, when you're in a good team. Yeah. And all of a sudden it's just, it's great collaboration. It's great fun. Things are getting done. Yeah. And, yeah, those are, those are really great. And you also know very quickly.

But I think you just hit on something is that it's great fun. And it is, I think, really successful teams. They laugh a lot together. They have a good time together. There's a feeling of, we're in this. We're all rowing in the same direction in the boat. We're winning. We're making progress. We can see our results. And we're having a good time doing it together. And it's rare when you get to be a part of that. But once you do, I think it's very hard to go back.

I also look for is, you know, do these team members have good work balance? You know, are they, do they have lives outside of work? Because I think when you come to work and that's your only agenda, you begin to get a personal agenda. And so I oftentimes at teams also look, you know, what's going on outside of work? You know, it's...

People, I think some corporations love it when they've got employees willing to give 60, 70 hour work weeks. I don't. I don't think that that's healthy. I don't think that it's good for any team. Because I just, you know, I think that you need to have that balance in there. I agree with you. I also don't believe it's very productive. I think, you know, we're humans, we're social creatures, and it's, you know, the batteries need recharging. And if you're just going at it for...

60, 70 hours a week, week after week. Now every once in a while, yeah, sure. Pull up the bootstraps, dive in, you got to get something done. No problem. But if that stuff drags out for months on end, yeah, the human nature goes right out of that really quick. I think leaders today that have been in leadership roles for the past, say four to five years, they led through an unprecedented time. I mean, nobody had a playbook for, by the way, we're going to throw a global pandemic in the middle of what you're doing, by the way. So just throw that in there.

Stephen Brown (10:44.494)
But can you just give us some insight, Wendy, on the process that you use when you have to make tough decisions? Well, yeah, and I think there's a couple of them, Stephen. I think, you know, I used to work for Amazon, AWS, and I don't know how familiar you are with Amazon and their culture, but they live and die by their leadership principles. And there were 13 of them when I was there. And...

They have a couple of them that I've taken with me and I'm thinking I've implemented them. The first one is have backbone. And what that means is executive leaders or strong leaders have opinions and come to the table with that opinion. Now, what I would tell you is I would say come to the table with data.

especially in challenging times, you bring up the pandemic. I mean, it was a very emotional time. People had kids, they had dogs. It was, we were all, I mean, we were crazy. So to the extent that you can take the emotions out of a decision and come at it from a data -driven decision, I think is something that I have learned very early on and it's how I come to work. I come armed with it. So.

you know, have backboneing and come to that table with the opinion. But at the end of the day, you have to at some point disagree and commit. And it's really that second part of that, which is the commitment part that is important. And one of the other things that Amazon does around that is they take decision level, decision making, and they drive it down the organization. Because, you know, as you said, a lot of times these decisions are made at the executive level, but they don't need to be. They don't need to be. And...

If organizations can make decisions faster and get out of their way, and if they're not circling back on those decisions time and time again, the organization moves forward quicker. So it's, you know, have backbone, disagree and commit. But there's another concept that I like. It's around one -way and two -way doors. And this is all on the internet, I'm sure a few. I mean, I'm not, I'm, I, this is very Amazonian, but.

Stephen Brown (12:54.446)
It's the concept that if a decision is a two -way door, meaning I can easily walk in and I can easily walk out, you know, it's two ways, those decisions get pushed down in the organization. Anybody can make a two -way door decision. Let's make it, let's disagree, but then let's commit and let's move. If it's a decision that really is a one -way door, it's going to dramatically change the company, it's going to change the strategy, it's going to take years to unwind.

That's called a one -way door decision. And those are really the decisions that should go up to the executive level. But other people in the organization need to be empowered to make those decisions that are not going to really impact the organization in any critical way, that they can't quickly unwind and reverse. I love something that you said, and it's part of the DNA that I've inherited or learned over the years, but there's only a couple of ways.

You can make decisions and then go about them. One is you can agree and commit. You can disagree and commit, but you can't agree and not commit. Yeah. And you know, you want healthy debate, you know, you want ideas, you want like, what Steve, that's the dumbest thing I've ever heard of. Well, really, but what about, you know, you get through all that, but once you're done as a team and you go, okay, here's what we're going to do. Okay. Everybody gets on board and then you face the world and you go and you make it happen and you execute.

Yep. There's nothing worse than when you think you've got people on board and they've committed. And then you find out that there's these back office meetings and they're revisiting, you know, the same kind of, it's like, guys, we talked about this two weeks ago. We talked about it three weeks ago. We talked about it four weeks ago. And so I think that commit is, is really the key word there. Yeah. So one of the topics that I love.

to talk to you a little bit about, we could probably do an entire episode or maybe a whole week's worth of episodes on AI, but just can we touch on it just from your opinion on, you know, what do you think about it? And how should executives in roles like yours be thinking about AI? Yeah. It's such a hot topic today, and you're absolutely right. We could talk about it for days.

Stephen Brown (15:11.022)
And I'm a big believer in AI and the potential of AI. But I know that there are a lot of folks who aren't, who are kind of on the other side of almost paranoia that, okay, AI is gonna come in and take over our jobs. And especially in the marketing world. I think there's a lot of folks who believe, and I don't understand why they do, but that what marketing does can easily be handed over to AI. And I don't believe that. I think that...

you know, today, if you look at AI, it's very much in its early stage. And, you know, I think of it as almost the toddler stage, you know, it's, it's, it's, it's very, very young and very, you know, it's out of control, walking around on its own, throwing pantroms and that said, but I believe that AI can really help marketers become more efficient and more insightful and more customer focused.

which is ultimately going to drive better results and ROI for their initiatives. And so we've been in my practice, looking at AI, bringing AI into the organization in a couple of areas. So I think, you know, the first is data analysis and insights. So AI can handle so much more data quickly and accurately than we can do on our own. And, you know, typically in the past, I mean, this is years and years ago, but you had data analysts in your marketing group.

who looked at Google Analytics, and that was big, Google Analytics. But their job was to really get in and dig into the data to find what worked, what didn't work. And that could take a week. It could take days to weeks to months. Now you can have that done very quickly with the power of AI. And what that's doing is it's just freeing them up to do higher value work. So I think that's an area that we're going to see really explode in marketing. I think we've all been...

impacted by the AI personalization power. So now you've got algorithms that can create highly personalized experiences. And they do that by analyzing past interactions, preferences, their demographics. And so now you have this whole new experience when you come in, whether it be your website, whether it be your support sites, that it's like, okay, this company really knows me.

Stephen Brown (17:31.598)
They they and then I do it all the time I shop now the only place I shop is on Facebook or Instagram because I come on and they know exactly And and you know it works so That to me is just again helping us make better use of our marketing dollars I think there's the really repetitive tasks, you know likes email marketing

Social marketing that again, somebody's got to be there to make sure that those things happen. Well, now with AI, this frees up marketers time. They can now go focus on the strategic initiatives that fall after that email campaign. Look at more planning and look at more creative development. I agree with you. Yeah. And so I think there's a lot of opportunity for AI and that what we need to do is we need to be embracing it. And I think...

I think it's going to be one of those things that just becomes, you know, 10 years from now, we'll be like, my gosh, how did we ever do this without it? Well, embracing the technology, I think is key adoption. And if you don't, you're just literally going to get run over by a freight train because it's coming and it's coming fast. Yeah.

Is it going to change? Sure it is. Is it going to eliminate some potential? Of course it is, right? Most technology does some sort of optimization around it, but to your point, it elevates people to go and focus on the things that actually really matter because I won't write content now without running it through AI. I won't, I just won't, you know, and if I'm sending important emails, I run it through a chat DBT. It's like, Hey, why wouldn't you? Why wouldn't you? It's almost like having a little buddy there.

Well, it really is. And you know, I know a ton of writers, like I myself do a ton of content. And sometimes you just need something to start with. I mean, like I said, it's a toddler at this stage. So you'd never go go say, hey, create me this blog, and then just put it out without having that human interaction in between it. But it does give somebody a starting point. And again, it's all about that productivity.

Stephen Brown (19:40.078)
Now, instead of maybe doing one blog a week, you've got somebody who can do two or three. And that's a really super relevant. Yeah, exactly. And look at your organic SEO results. And yes, that's a win -win for everybody. Very cool. So let me switch gears on you a little bit. So you've worked at public companies, you worked at private companies, you've kind of done some stuff on your own. You've done quite a bit.

over the last 30 years. So can you pick out for the listeners just a couple of nuggets of your career that really like, man, I had fun doing that. Man, I learned life lesson here. Just something that you'd like to share with the audience about Windy. Yeah, thank you, Steven. So you're right. I've been at very large organizations and I've been at startups. I think some of the more memorable and fun ones for me were those.

very early companies that were Series A companies. So, you know, I joined a number of those when I was like number 20, you know, employee count. And you're the only person there. And you're thinking, what am I going to do? I'm a person of one. But you then get to be a part of that growth. And, you know, you take I've taken companies from Series A through Series C, Series D, you know, been the only marketer then, you know, had teams of up to 60 people, you know, at this one startup organization.

And I think what that really taught me was the ability to be very hands -on. And what I know about myself is I'm a very hands -on marketer. So I don't like the peer management roles. I know that I've had CMO roles in very large organizations where your job literally is you go to meetings and it's peer management. You're not doing any of that hands -on work. So I have learned that at least I know.

what makes me happy and what makes me tick. And that's really, you know, getting my hands on the keyboard per se. But as far as like the most memorable experience, I think about this was a bigger CMO, bigger organization. And I learned how to play boardroom bingo from the CEO and the CFO. Have you ever heard of boardroom bingo? I have not, actually. that was so funny. So this was, I think it was before an earnings call.

Stephen Brown (22:04.494)
and the CFO went and wrote on the whiteboard, Jagger. And the CEO starts laughing. He's like, all right, that's our word for the day. I'm like, hey guys, what are we doing? And they had to explain boardroom bingo to me. So somebody picks a word and then somewhere in that meeting, so whether it's a board meeting or maybe it's the live Q &A session of the earnings call, you have to work that word into your response. So in this case,

It was an earnings call and I think one of the analysts has asked how we were going to respond to one of the latest competitors offerings. And he said, hey, you know, just like Jager, no, our company has moves just like Jager and we're well positioned, you know, to capitalize here. And I think I actually at that point spit out my water. So that's something that I've now brought to other companies and, you know, taught other people in my position there in the...

mostly sweet, you know, bordering room bingo and kind of as you say, it doesn't nobody said it can't be fun. So, you know what, though, there's there's some science behind that, because if you're thinking about that word and thinking about having to work it in somewhere and you were going to be hyper attentive to what's going on in those conversations, that's probably true. That's pretty cool. See? Yeah.

That's worth a half an hour right there if people listen to this. Well, there you go. And I can't remember what the prize was. We probably had to buy him a beer or something afterwards, but it is a funny thing to do. And again, it's about building the team. We were a CEO, a CFO, and a CMO sitting in a huge conference room, virtual earnings calls, and having a lot of fun with it. So that was kind of memorable for me. That is really cool.

So wrapping up here, I have one final question for you. And so I consult with people and help them with go -to -market. I help them with sales, talent assessment, just because I love it. I love working with people. I love working with sales organizations. And over the years,

Stephen Brown (24:18.19)
You know, marketing and sales are very connected, you know, and, and years ago, it was pretty linear. If somebody wanted information, they'd go to the sales person to get it. And then it was one of these, well, now it has almost flipped around marketing plays such a heavy role in informing customers and informing peers. And, you know, so my question in a long drawn out way is for modern salespeople today, what advice would you have for them?

when they meet with a C -level person. Yeah. Yeah. Well, I have always believed that everyone in a company works for sales. And I very strongly believe that. And I know that you may have people in marketing go, horror.

But at the end of the day, it's our job to help those people who carry a bag reach their revenue target and therefore help the company grow the business and meet the company's revenue targets. So for that reason alone, I think marketing sales need to be in lockstep. I think historically, you saw a lot of contention at times between these two groups. Whereas today,

they need to be working hand in hand. So marketing needs to know from sales, you know, what's going on in the field? What are you hearing? What are the questions, you know, that prospects customers are giving you? Marketing needs to know, know what's going on from a competitive landscape and be able to say, okay, hey, this, this company has now launched this. And, you know, those things need to come together so that marketing can, at the end of the day, provide enablement materials that allow those teams to be effective.

So I don't know that it's what advice I'd give to engage with a C -level person. I would say you need to not just engage, but build that relationship. There needs to be bi -weekly meetings where you sit down and you're discussing exactly what I've said, what's going on, what are you hearing, what's working, what messages are resonating, what's not resonating.

Stephen Brown (26:28.238)
And it really needs to become a team, a team approach. And I've seen that work exceptionally well. So my advice would be, go set up that meeting. If you don't want to do a formal one, go to lunch, go to happy hour. You'll really get to know each other so that this becomes a very frequent channel, I guess I would say, of communication that's open. And I think with that, both teams are going to get the best work that they can.

from each other. Yeah, I agree. And so I'd be interested in what you think about this, because I've been advising a lot of folks. Because when you come in in a brand new engagement, you're trying to solve one of a couple problems, either A, they're not getting in front of enough clients, they're not closing enough deals, whatever it is. And then you'll hear the obligatory, and I've heard this so many times, it just makes me laugh. It's like, well, can't we just give marketing to give us the three silver bullets? I'm like,

Yeah, hang on. Let me just hit that easy button there. That will just do that. You know, if it was that easy, it's like, come on. And then, you know, the other one for for for sales guys is, you know, they're like, I just got to get to the CEO. It's like, well, do you like maybe, you know, but so my advice has been to these folks that, yeah, you're going to meet with the CEO or the CMO or some at some point, but they've put a lot of people in place. They built teams, they've set missions, directions. They've got a lot going on and there's.

I don't know that they're making those types of decisions. In other words, when you get to the point where you need to meet with that CEO to make a decision on capital, what are you trying to do? I took your question wrong, Stephen. I'm sorry. I thought you meant internal salespeople to salespeople. You're talking about somebody that's selling that needs to engage with the C -level person. Is that what you meant? Yeah, yeah, exactly. I was talking about internal teams.

So that's interesting. I think that you have to think about what does a CMO care about? If I'm going to be sold something, it's typically a tool. When I think about what it is that I need, it's typically a tool. And so that's going to be, how does that help my team be more efficient, be more effective, be able to quantify, and be able to innovate faster?

Stephen Brown (28:51.054)
I think that that's what every CMO wants is the ability to develop high impact marketing programs, but be able to prove that. Because I think so often it's like, what's marketing done for me lately? They need that tangible ability to showcase work and showcase their results. So I think any salesperson going to a CMO needs to just put themselves in their shoes and go, okay, what is it that...

this CMO cares about. And that is, it's all about helping their internal sales teams become more effective. Yeah. Yeah. And that's exactly what I've been trying to help people get to. I mean, I think fundamentally, people want it, well, I want to get the meeting, I want to do this. It's like, well, but before you get there, let's assume all your dreams come true and you get that meeting that you want.

You know, have you done enough homework? Have you met with enough people? Do you understand their problem well enough to go in and say, hey, look, I've met with your teams. Here's what I'm recommending. Here's the tool and here's what it's going to do for you. Exactly. And you know, it's not always going to be the CMO's decision. So as I mentioned, there's distinct disciplines, right, within marketing. So are you, do you need to talk to the growth marketing team? Do you need to talk to the product marketing team?

Do you need to talk to the channel team? And so I think what happens if you just go directly to the CMO without really vetting that to the people who are gonna be hands -on interacting with that, if we're using the analogy of a tool, you're missing the boat. Because what the CMO is gonna say is have you talked to the team? Have they tested it? Do they know that this works? What's it replacing? So I would make sure that...

You've got that buy -in and you've got the support from the folks who are actually, you know putting fingers on that That tool on a daily basis That's great. That's great. Awesome Wendy. This has been fantastic This was so fun. So thank you for inviting me. I appreciate the opportunity to come and dialogue with you You're very welcome. So Wendy Casares ladies and gentlemen, thank you again This has been another episode of getting to know your CXOs. We'll see you next week

Stephen Brown (31:10.254)
Thanks, Stephen. Bye. Cheers.