#267: How Product Marketing Is Evolving in 2025: Lessons on AI and Leadership with Jennifer Cannizzaro

#267 Product Marketing | Matt is joined by , VP of Product Marketing at Responsive and former marketing leader at Whoop and DocuSign. Jennifer brings deep experience in building strategic, insight-driven marketing teams at high-growth B2B companies and she’s at the forefront of using AI to scale smarter, not just faster.

Matt and Jennifer cover:

• How product marketing can become a company-wide growth lever through tighter GTM alignment, strategic planning, and better customer intel
• Practical ways her team is using AI to reduce content workload, cut freelancer spend, and increase speed-to-market
• How to coach marketers to use AI responsibly, and why curiosity and judgment matter more than ever

It’s a tactical, behind-the-scenes look at what high-impact product marketing really looks like in 2025, including strategy, systems, and AI.

Timestamps

• (00:00) - – Intro
  
• (02:37) - – What product marketing owns today
  
• (06:24) - – Launch and learn vs launch and leave
  
• (07:34) - – How PMM drives company strategy
  
• (10:59) - – Aligning teams around growth levers
  
• (14:34) - – Gathering customer and market intel
  
• (18:39) - – Quick, AI-powered research tactics
  
• (20:19) - – Sharing insights across the org
  
• (25:00) - – Real examples of AI in use
  
• (28:20) - – Eliminating freelancer spend with AI
  
• (30:00) - – What to feed AI to get results
  
• (32:50) - – Coaching teams to use AI well
  
• (36:20) - – Weekly AI spotlights and team habits
  
• (38:35) - – Building a team-wide AI culture
  
• (42:05) - – Setting realistic AI expectations
  
• (45:50) - – Example prompts and experiments
  
• (48:07) - – The role of community and mentorship
  
• (54:20) - – Final thoughts and wrap-up

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Dave Gerhardt [00:00:00]:
You're listening to B2B marketing with me, Dave Gerhardt.

Matt Carnevale [00:00:17]:
In this episode of the Exit Five podcast, I sat down with Jennifer Cannizzaro. Jennifer is the VP of Product Marketing at Responsive. She's led marketing at companies like Whoop and Docusign and brings a ton of experience from high growth startup and scale up companies. We got into what it really looks like to lead a marketing team today, especially around product marketing leadership and the role AI is playing with her and her team. You'll hear about how she's thinking about the evolving role of product marketing and why it should be the main strategy driver, how her team is using AI in their day to day work, and overall how she's helping evangelize AI across the organization. All right, I'm here with Jennifer Cannizzaro. Jennifer, how's it going?

Jennifer Cannizzaro [00:01:03]:
Great, how are you?

Matt Carnevale [00:01:05]:
Yeah, good, good. Doing great, doing great. It's great to have you on the show. We recently met through Exit Five CMO club and I thought you had a really interesting background and career. You're currently the VP of Product Marketing at Responsive. So yeah, I'm excited to just get into, you know, a bunch of different angles on product marketing, marketing leadership and how your team is using AI today. But yeah, we'd love for you to just start by telling us you know, what you're working on today and then even give us a bit of your background as well. Sure.

Jennifer Cannizzaro [00:01:36]:
So as you mentioned, I lead product marketing at Responsive. My team is actually comprised of a few different parts. So I've got core product marketing that's working in close partnership with product management to really bring new innovation to market, driving the go to market strategy, the messaging, positioning, enablement, so on and so forth. One of the things that's really exciting for where we are as a company is that we went from really being more of a point solution to truly being a platform that is getting utilized by more teams across an organization with a larger product portfolio. So that's very exciting position for us to be in and truly kind of creating a category around that. So that's one of the things that we're working on. I also have the integrated marketing and content team, so we're producing everything from thought leadership pieces to blogs. We've recently really gotten gone in and kind of revived our video program.

Jennifer Cannizzaro [00:02:45]:
That's kind of a work in progress. And then I also have advocacy and reference. So simply put, I've articulated my charter for the team as delivering value that customers pay for and stay for because we're driving that overall go to market strategy, monetization, messaging, positioning, enablement, all of those things. But it's really cascading throughout the customer journey and bringing that voice of customer into everything we're doing and really ensuring that the things that we're launching are driving value for our customers. And that's something where, you know, it is constantly a work in progress. I also take the mindset of launch and learn instead of launch and leave. So, you know, we've released a lot of new products and innovation even in just the past year and a half that I've been at the company. But there's always more work to do even after a major release.

Matt Carnevale [00:03:46]:
Yeah, I feel the same even, even at Exit Five, which we're obviously like a much smaller company and we don't have. I don't even know if we have teams. We're just, we both, we all kind of do a lot of different things. And from my perspective, you know, I do a lot of stuff inside the community, obviously, and we treat the community as a product with a bunch of different features. And just a couple weeks ago I was going bonkers and I was launching a bunch of new stuff into the community. And then now I'm in a position where I'm like, okay, well, I just launched like five or 10 things in two weeks, which was kind of crazy. And now I got to do, I'm learning and I got to do all the making that stuff actually work and getting adoption for all those features. So I definitely feel you on the launch and learn.

Matt Carnevale [00:04:30]:
And I've been in companies where the product team launches something and then it's like two weeks later. It's, it's almost as if like it's an on nobody's radar just has totally fell off the map. So.

Jennifer Cannizzaro [00:04:40]:
So yeah, you never catch everything. And I think that's part of it. So, you know, I'm also a big believer in progress over perfection. And so it's like you have to answer the right questions and make sure you're socializing and working with the right stakeholders as a part of the process. But feedback is a gift. You know, people are engaged and they're going to tell you what's not working and what's missing. You tend to get more of that than like the pats on the back. But that's, that's just fine.

Jennifer Cannizzaro [00:05:09]:
That's leadership too. But I think it's great because we're able to then build and iterate and not just say, oh, it's out the door. That's the Worst place to be is to just go and abandon something when really all the learning comes after.

Matt Carnevale [00:05:26]:
Yeah, totally, totally. It's much easier to launch something. It's much harder to actually take all the feedback after and continue to iterate and make it work over time. So you've been in product marketing for the last, I want to say, decade or so. It seems like maybe you've gone in and out of it, but that's where you are today. It's where you've been in the past. Even at DocuSign, how have you seen it change in the last five or 10 years?

Jennifer Cannizzaro [00:05:50]:
Yeah, so I'm sort of an accidental marketer. Actually. My foray into product marketing was following strategy consulting and then business school, where I decided I going to move to San Francisco and get into tech. And so I've been there ever since. A couple things I. I would say with respect to, you know, product marketing and its evolution, I've always found that product marketing needs to ultimately reflect and drive the strategy of the company. I think that's actually something that's remained true over the years, but depending on the type of organization you're in, you might have to do a lot of work to get people to realize that. So I know you asked me about what's differed.

Jennifer Cannizzaro [00:06:34]:
I think that is something that's actually remained the same. And I found it in most organizations that I've joined. I think DocuSign was the exception where that value was more broadly understood than some of the other places I came in kind of earlier. And you actually have to be ready to answer the question when somebody inevitably asks you, like, what does product marketing do? And so I think, you know, over the years, and especially look, if you look at the past, even couple of years with AI, like that's disrupting every function and in a positive way, I think including product marketing, it's really allowing product marketers to focus on the stuff that they're really great at, which is strategy and building relationships and driving forward the things that truly create differentiation and, you know, kind of airtight positioning for the company, because that's not something like AI can help you. But like AI is not writing your company strategy or your, your positioning. It can be a brainstorming partner. But you know, what I find oftentimes is we're like the engine behind AI in some places, like our own platform actually pulls together a lot of, you know, organizational knowledge that you can use, whether it's in RFPs or in more of like a conversational interface. A salesperson has a question, they can get an answer.

Jennifer Cannizzaro [00:08:14]:
And my team is constantly feeding that engine and it's super powerful. So I think now with the advent of a lot of changes in the broader technology landscape, it truly is making work better and more focused. So that knowledge that positioning can have more power and consistency across the business, more people can tap into it. And you know, in addition, you've got technologies in, you know, like the compete or win loss space that make it much easier to actually keep a pulse on what's happening in the market and pull together quick summaries or have a starting point or even have an automated way of routing win loss interviews. So I think it's really just unlocking more of the potential and there's sort of like less drudgery involved if we're really harnessing AI and a lot of, you know, technology in the right way.

Matt Carnevale [00:09:16]:
Lots to unpack. There are a lot of great points you made. I want to unpack the first one. You said product marketing needs to drive the strategy of the company. How, where do they start?

Jennifer Cannizzaro [00:09:26]:
Well, you know, it really begins and ends with what I mentioned earlier, which is value. We should be creating value for customers. And I think part of the reason that I fell into product marketing was because of my background in consulting where, you know, I describe myself as a blank sheet of paper person. Like I would get put on these engagements with like VPC level and I was like 22 years old and it was like, figure out a three to five year strategy. And you just really had to figure it out. And that required relationships and data and input from other places. And so product marketing to me is in like the best position to really have a handle on what's happening across the company because you're working with product and what they're bringing to market. You're also looking at like, what are the growth levers that are going to take us from point A to point B to reach our targets this year.

Jennifer Cannizzaro [00:10:24]:
Like, I played a significant role in our annual planning process not just for go to market, but for the whole company. And the types of conversations I was having were around, hey, we're saying we're going to attach a number to this thing, but product's not building it. So how do we actually bring everyone into alignment? So when you ask how, it's really like it's taking a holistic look at answering the question, like where does the growth come from? And that can have a lot of different answers that product marketing is typically partnering and driving. It can come from a partner channel and partner marketing falls under my remit as well. It can come from new products, it can come from opening new markets, whether that's expanding into different industries, geographies, et cetera. And so it really is through a deep understanding of, you know, what are we doing to achieve our targets and then what does that mean for the products we need to build and how, how are we really like harmonizing that across the company such that we are truly driving towards the same thing cross functionally. And that's really the seat at the table that you have. But like you have to take that view to ask the questions and build the relationships to get there.

Jennifer Cannizzaro [00:11:57]:
And to be the one to speak up and say this feels miscalibrated or you know, I'm seeing this here, this here, or even like that's a tactic, not a strategy. I've been the person to say that before too. So I, I mean it's maybe a high level answer, but to me it really is. Like I said to someone the other day, it's like you hold up a mirror to company strategy and that is really how the team is resourced across those different growth levers, from different markets, industries, partners, to the products themselves.

Matt Carnevale [00:12:32]:
Okay, cool. So in all that, a big thing that stuck out to me is information. And you need to be good at, at getting information from different stakeholders in the company and the market to help understand, okay, this is the strategy that, that we're A should follow or B are not following and should be. So how do you go about getting that information? What are things that you need to do inside the company or even with customers that help you get there?

Jennifer Cannizzaro [00:13:02]:
There are kind of different levels of intelligence and knowledge. Like the field is a huge source of intelligence. And when I say field, I do not just mean sales, I also mean customer success because it really is looking at that entire life cycle and they'll. This has been an unpopular view with some, but I've always said that you have two customers, you have your paying customers and you have your internal customers because they need to understand and be partnered with you on, you know, messaging and go to market such that they can actually have the right conversations with customers. So the intelligence that you get, understanding where are we winning, where are we losing, what's going on with retention, churn, upsell, like all of it. It starts with the front lines and having those relationships and being a part of the forums where we're really digging into that information is so critical. And it's also like if you're not included, get yourself invited is what I would say to, to people, especially earlier in your career, because those conversations are happening and they're really critical so that you really can have a pulse on the full spectrum of things. There's also just broader market intelligence.

Jennifer Cannizzaro [00:14:22]:
Now to me, like win loss is super powerful. And I have found, I like to say I'm maybe a secret keeper is the wrong way to frame it. But like, people will tell me. People, customers and prospects will tell me things they will never tell our salespeople. And it's because I'm not actually a salesperson. And to me, the best. It's not even necessarily product marketers, professionals, let's just say the best professionals are deeply curious. And when you bring that to a conversation, you're ultimately oriented towards learning.

Jennifer Cannizzaro [00:15:01]:
Then you can have a really positive interaction. And so actually having the operating rhythms in place to understand both why are we winning and let's do more of that and where are we falling short and what should we do differently is really powerful for me to build into that overall market intelligence. And also I've always liked to have like a handful of customers kind of in my back pocket who I could call and get quick, quick feedback on because they, they're sort of friendlies and we've built a relationship through events or roundtables or whatever. And that's something that you don't have to be a VP to do. Like anyone should do that. I did that even when I was a product marketing manager. So that to me is sort of like what I mentioned for both internal, external sources. That's like always on intelligence.

Jennifer Cannizzaro [00:15:55]:
But there are also times where you actually need to go deeper on something. And that's where more focused market research might be required. Now, before I would dive in and spend a bunch of resources, time, money on something, I do want to validate that. We've got the data that points to, hey, we really need to figure this out in a way we haven't either had the capacity to do before or that we're not getting from these other sources. So that could be something that's informing changes to your pricing model is a popular area where I've typically done deeper dive research, but it also doesn't always have to be paid. Like you can do a lot of things and I think AI is actually making this even more powerful today. That's kind of quick and dirty. Where in the past you may have had to hire an agency to do Persona research and then it took them time to ramp and you had to write a guide and all of this stuff and now you can actually like, one, probably get a good head start just mining what's out there about your target customer or icp.

Jennifer Cannizzaro [00:17:05]:
And two, like, you could develop an interview guide and get going the next day if you really wanted to. And so that kind of goes to your other topic too, of like, how is product marketing changed? Like, I find a lot of value when the team themselves can have some of these direct conversations. And it's becoming easier and easier with the tools and technologies that we have at our disposal. But those are just kind of a few different ways that I kind of look at the broader landscape of how you get that data and information intelligence.

Matt Carnevale [00:17:37]:
Yeah, no, that's a great answer. And I want to transition to. So you touched on AI. Obviously we're going to talk about AI. We have to. It's 2025, it's relevant in every episode. But before I do that, one thing super quick. What's the best way to surface this information? I've always found that you can go talk to customers, you can be that voice internally getting all the right information.

Matt Carnevale [00:18:00]:
But the toughest part is like, how do you bring this information to light and how do you make it so that it's like people look at you as the person who is the holder of market information.

Jennifer Cannizzaro [00:18:10]:
I think that there, there's not just one way to be honest with you. Some of it it comes down to like doing your work in public, such that when you have had an executive roundtable or if you've gone deep on research, like you are actively socializing that in the right forums. And so, you know, look, it could be something as simple as we were at an event last week and I had a friendly, I knew do some secret shopping. And we're posting, I'm posting that in my weekly update to the, the leadership team. And that is a quick like less than a week turnaround. That's valuable information and that gives someone something they can do differently the next week. For other types of intelligence or projects, some of it might just be baked into like your go to market strategy or the way you're bringing something to market. So it could be part of the new product introduction process.

Jennifer Cannizzaro [00:19:08]:
And you've gone out and done these interviews and this research and so you're kind of wrapping it into the way you're launching and evolving that strategy. It could be like, hey, we just did this pricing or Persona research and here's the readout and I'm hosting something or joining up in a customer success meeting or senior leadership meeting. And so it's I think a big part of this is like attaching to the forums that exist when the topics are relevant, but then also having your own plans and being able to iterate those as you go, whether that's a new, A new product introduction or actually just like the strategy for winning in a particular segment or whatever that might be. So it really to me is a. Like, when you're getting this, it should be going somewhere or why else are you doing it?

Matt Carnevale [00:20:00]:
Yeah, love that. Yeah, I like that point about just sharing something as it happens. Like at previous companies, I tried to create process around this. It was like, okay, I'm going to, with this intelligence and research, I'm going to put it all in the doc and then once a week I'm going to write this nice message, which is like this weekly intelligence message. And it's going to get everyone excited because it's all this good information once a week that I'm sharing. But that's just really hard to keep up with. And so many things come up during the week. But what I found now is what you said.

Matt Carnevale [00:20:29]:
It's like if I see something in the market or talk to somebody, I'm just going to go share that thing right away. It doesn't have to be perfect. Even if it's quick and dirty, it's better than nothing. And then the other piece of it is like, again, along the theme of like attaching to the forums, like in a team meeting when we're trying to discuss whatever it is, some kind of strategy I can validate or invalidate, maybe that's not the right word, but validate or invalidate certain ideas through what I know about the customer. If I'm out there talking to customers, I can say, oh yeah, I spoke to Jennifer, you know, she said she was super interested in this. As a marketing leader, I think this is a great feature for us to go and build. So I like the idea of attaching to existing forums.

Jennifer Cannizzaro [00:21:08]:
Yeah, for sure.

Matt Carnevale [00:21:10]:
Cool. So you touched briefly on AI and the intersection with product marketing just really broadly. And I think we can go deeper off this question, but what are some ways that you and your team are using AI right now today?

Jennifer Cannizzaro [00:21:24]:
Yeah, so this is probably like Captain Obvious, but we're using it significantly for content to the tune of generating the first draft refinements, you know, kind of tailoring for different types of mediums and audiences and pulling through the consistency of tone of voice, audience, et cetera. And I know I mentioned this in the forum just last week that we had around AI, but I was talking to our lead this morning, in fact, and we are truly doing more with less in this area. I know that sounds trite, but we're totally seeing the benefits pay out to, to the point where the team is actually smaller than it was last year. We had a freelance budget and we've said we actually don't need it. In fact, we can pull some of that into standing up more like pillar content. And we've taken on, you know, a lot of work extensively across thought leadership, the website, et cetera. And it's significantly cut time without compromising quality. I think one of the best signals where AI is working is you can't tell AI was behind it.

Jennifer Cannizzaro [00:22:45]:
So even when I looked at our thought leadership piece this year versus last year, I said to my team, I said, I can't even tell that you used AI. And they wrote the first draft in like 75% time saving, you know, a fraction of the time. Like it. It took a fraction of the time to even generate the first draft and I couldn't tell. So that's a big one I right now. And I'm also using, whether it's like a press release or brainstorming product names or just like as a brainstorming partner, there are a ton of uses where we like, we're bringing AI to brainstorming sessions, are able to kind of frame up and make decisions a lot quicker with it. And I think kind of the next frontier for us is really more of the custom GPT type of stuff, you know, putting agents on the org chart, which is something I'm kind of working to do where I we're starting to do more with like AI and compete automating workflows, summaries, you know, that sort of thing. So it really is kind of cutting across the team.

Jennifer Cannizzaro [00:23:58]:
Even in one of the tools we're using for reference and advocacy, they're starting to build agents into that platform. So, you know, the way I look at AI broadly, there's like AI within the workflow and within platforms that you're using already, which is a great place to start. In fact, like that's what we're doing with our own product. So it's like, how can we get more out of the tools that we're using that are kind of, you know, bespoke to a particular area? And then what can we also be doing more as individuals who are looking for better ideation, better brainstorming, that sort of thing. And so I think there's sort of a mix between broader B2B tools and platforms and what the power that something like ChatGPT or Claude or something like that. ChatGPT is the one we have approved what that can really wield for even individuals on your team and what they're able to bring to the table.

Matt Carnevale [00:24:58]:
Okay, very cool, Very cool. So, okay, a lot, a lot of interesting points in there. The part about the freelance budget. So was that originally carved out to just help with some like, you know, zero to one type writing or. Pretty much, yeah.

Jennifer Cannizzaro [00:25:14]:
Well, we originally. So we're continuing to grow the business and really look at some of these additional growth areas like we talked about earlier with markets or industries that are a particular focus. And so we were looking at it as, hey, we're going to need some additional kind of specialized content in these areas. And we'd made the decision to convert a role into freelance such that we could get kind of more like specialization across different mediums and subject areas, I guess, if you will, tied with those growth areas and frankly just didn't recognize how powerful AI was going to be to get us where we needed to go, even with those additional focused areas and the customization that we'd need. So, so that was essentially what happened. And I literally had this conversation two or three times where I was like, okay, I'm going to take this money, I will use it somewhere else. Are you sure? It's like, yes, I'm sure. So we have seen tremendous benefits.

Matt Carnevale [00:26:20]:
Okay, cool, cool. I know you had mentioned this earlier in the episode. What are you doing to prep the AI? Like what, what are you feeding into it? What's your team grabbing? Is there a central source where they're taking stuff from and putting it into there?

Jennifer Cannizzaro [00:26:36]:
Yeah, you know, I think, look, I'm not at the like all the layers of detail on this. I think it's generally like our core messaging, examples of things we've written in the past. That would be like, for instance, the thought leadership report last year gives context around the style and the tone and you know, the appropriate, what's like, appropriate for a thought leadership piece. So like it is, it is both the overall messaging, target audience, positioning, tone, all of those things that should have consistency but also like, hey, if you're writing a thought leadership paper, like here's an example of one that's quite good that you should lean on and that would be different whether it's like a longer form state of whatever report versus a blog post or something like that. So that is also where, you know, it's great to have both content and the core Product marketing team working together because as we're really driving towards major announcements or updates on the website, it really is that partnership of what is the core messaging and positioning an audience and then how is that going to manifest into what it is that we're writing? And so even as much as we have that for the company overall, anytime we're innovating or iterating, we do have to update that and kind of feed it back in and, you know, it's continuing to learn and evolve with us.

Matt Carnevale [00:28:10]:
Cool. I want to talk about AI and specifically product marketing in general. We're at this point where we have a seasoned product marketer like yourself who is probably used to being more strategic at this point in your career, but somebody who is maybe a couple years into their career was there to do a bit of that grunt work. And now a lot of the stuff that they would have done is AI can do it for them. So how do you see the role of product marketing, maybe for a junior product marketer, less experience changing now do they have to get more strategic? Like what skills do they have to be smarter about earlier on?

Jennifer Cannizzaro [00:28:50]:
Yeah, I love this question. I ask our customers the same thing about like how our roles evolving, how is hiring evolving? And let me first state the one that that is somewhat obvious is like anyone that's coming in as a first job needs to understand how AI fits into their essentially their operating system from day one. So it is very different, I think, in a good way. Actually. I've read a lot of articles about, oh, are junior roles going to go away? No, we just have to think about them differently. So where I'm starting to see more success and this is within my own team, but more broadly is it's just getting people into the mindset of like an AI first mindset. So in the past, and look, I think back almost 20 years when I was in consulting and you had to go research something because you got on a new project and you're trying to understand, oh, okay. This is the first time I've worked in consumer packaged goods.

Jennifer Cannizzaro [00:29:58]:
What is CPG stand for and what is this company's 10k? And I would literally like read 10ks and scour the website and do all of these things. And I don't know that like the hunt and peck, that was my least favorite thing to do, but I did it because that's what how it worked at the time. And now you're able to actually just ask the right questions and pull in all this research to get you started. I think the Dynamic, though, is one where you still, this is what I've recognized personally about AI and I think this applies to people earlier in their career, any stage of their career. You actually have to be like more curious and more strategic and smarter than AI in some ways to get the most out of it. So because I have read a lot of books and I listen to podcasts and whatever, I have a better reference point to say, take this view or reference this book or reference this methodology to get a better output. And so I think that it's going to put more pressure. Maybe that's the wrong word, but it puts important emphasis on actually like being curious, moving from the role of I'm finding things to I'm like discerning.

Jennifer Cannizzaro [00:31:25]:
And I'm questioning, you know, because you really can't take this stuff at face value still. And I don't know that we ever. It'll get better, but like, you always have to bring that curiosity and discernment into the picture. So to me it's like be a connected, well informed human being such that you can be more curious and be versatile enough with the AI stack or set of tools, you know, your operating system, such that you even know what to use for which thing. What's going to be a better fit for me doing something on my own versus you know, a workflow or something standard that I need across the business where everyone really should be drawing from the same tool, et cetera. So I think those are the types of skill sets we're going to continue to need to nurture both the fluency in, like, where do I go for what? Because it really is not one size fits all with AI, but also like, let's not lose that spirit. In fact, it becomes even more important to be curious. And still, just because AI summarizes things for you, you still need to read them.

Jennifer Cannizzaro [00:32:41]:
And actually the more well read, well connected you are, the better you're going to get good output and leverage from AI. And I think that will then allow people to actually start their career in roles that are more meaningful and more strategic than what it looked like when I was like a junior analyst at a consulting firm.

Matt Carnevale [00:33:04]:
Right. In your team, how are you coaching or talking to them about this topic? Like when to use AI versus not. Are you catching instances where you think somebody relied too heavily on AI and you kind of have to coach them back from it?

Jennifer Cannizzaro [00:33:22]:
I have seen that. In fact, when I've. I've caught it a couple of times. One, I do give the feedback back to the person like, hey, it was obvious that you used AI here, let's work on this. And I have, I've double checked myself by like putting it back into AI and saying like, does this look like something you would have produced? And it's like, yes. So I, I have seen that in terms of coaching, like, you know, I talk about mindset and it's, it's mindset and it's culture. So as a company, we have a priority around AI leadership and that is not only for our own product and platform, that's also how we're really infusing it into the DNA of our business. When my team set their annual goals, if they didn't have one related to AI, I sent it back and I said, what are you doing? And so it is at that level of it is a company priority.

Jennifer Cannizzaro [00:34:21]:
Individuals have goals related to what they're doing around it, with the functions that they're leading. It's also something that for my team, when we meet as a team, I set the expectation this year we're going to do an AI spotlight in every meeting so someone's going to share what they're doing. And it started as a little more ad hoc, but now what I'm doing this summer is actually challenging the team, both at an individual level, but then also we're kind of brainstorming around what are things that we're interested in or problems where we think AI could solve or play a role and really mobilizing around that as a team. A few heads are better than one to say, okay, go, this is a problem, come back with a recommendation. So it's got to be really at every level. And that's how I'm really doing. It is individually, what are you doing? What do you spotlight? How are we coming together in small groups to solve problems, to advance what we're doing, doing. And I also am like trying to be a little provocative with it.

Jennifer Cannizzaro [00:35:30]:
So like I mentioned the agents on the org chart, like something I'm doing right now to provoke a conversation and it's not one particularly because AI is so important to our business. Like that's not a scary conversation for me to have because there is an expectation like this is what we're doing. I'm infusing it into interview processes, right? So it's really just part of the DNA. And as I like as we were talking earlier about, you know, where, when you have knowledge, where are you putting it? It's like, well, it's not like one place. Similarly with AI, it's like it's built into the culture of the team in team meetings and goals and one on ones, you know, we're talking about it, we're showing our work, we're working together. And even across the marketing organization, we are really looking at how do we optimize our use of AI across the customer journey and that gets at standardizing on platforms and tools for the organization and really just bringing more visibility into what it is that we're using such that we can inspire more use cases and learning across the whole of the team.

Matt Carnevale [00:36:39]:
Okay, got it. Yeah. So it almost seems like, would you say that you or your team have been like the evangelists of AI in the company?

Jennifer Cannizzaro [00:36:50]:
You know, we're trying to be, I think truly every part of the organization is doing something. We see an opportunity to really bring the company together around how, again, like how we're using it across the customer journey and how we can infuse it more into the culture of what we're doing day to day. So like, we're happy to be the ones who can lead that or model that. And it's a huge opportunity. I mean, the conversations I have with customers all the time, it's really like a year ago people would come to us and say, like, oh, I have this AI mandate from leadership and they're really grumpy about it. It's like, okay, how about think about it as an opportunity? It's an opportunity to accelerate your growth and operational effectiveness as a company. And it's an opportunity for you to advance your career and lead because everyone's paying attention to this. And don't wait for somebody to ask you, what are you doing with AI? You go to them.

Jennifer Cannizzaro [00:37:59]:
That is really what I think is before us and how we should really all be operating. It's exciting. Choose to see it as an opportunity. And that does come back to mindset. Mindset. Wow, there we go. Mindset. Like how are you really thinking about it? It's an opportunity and it's yours to go get it.

Matt Carnevale [00:38:20]:
Yeah. At the company level, like, you know, let's say marketing, I, I think marketing tends to be on the forefront of AI more within a company just because the use case for us was so relevant from day one. Have you found at all in your experience, like you've needed to ground some other team members across the company in like realism of what, what's possible with AI? Like I find people will throw across a lot of buzzwords and imaginary scenarios. How are you, if at all like grounding that within the company and educating people on what's Actually possible.

Jennifer Cannizzaro [00:38:54]:
Yeah. You know, I think that comes. It comes down to a bit of the, like, doing your work in public and socializing. Because certainly there can be some very lofty expectations around, like, oh, AI is here. Like, everything just became easier. You can do 10 times the amount of work, and we're not giving you any more budget or people, et cetera. And so those tensions can always exist. But if you're really building the business case and sharing it along the way, which is really what we're.

Jennifer Cannizzaro [00:39:25]:
And it's constant work in progress for us where, like everything I mentioned around content, like, we are actually documenting. What have we tried, what are we doing? Like, what have we tried? What are we doing? What are the benefits and. And value that we're. We're seeing? And, and then like really socializing that that's. It's kind of how we're approaching it. And if, again, it's like, if you're kind of like waiting for somebody to ask you, it might be too late. So I can't say that that's, you know, everything I'm mentioning means you're never going to have to answer a question again, like, that's simply not true. But I do think so much of this is really around grounding in expectations and making the case and showing what it is that you're doing, but also as a part of that, like, where is it working and where is it adding value? And maybe what are some of the things you tried that aren't working or how our roles evolving, where this is where AI is great, this is where our team is really focused and that sort of thing.

Jennifer Cannizzaro [00:40:32]:
So I do think so much of this is about education because we are all learning this together. And the thing that I see as really promising as more teams and companies continue to do this is really being able to pull it together at the company level, which we are starting to do as well, where I could tell you some of the tools that HR has invested or CS and similarly for go to market, because we are pulling together and saying, here's how we're kind of standardizing on it across the company. So I do think just the socialization education around it and being very honest about it is really important.

Matt Carnevale [00:41:15]:
Cool. All right, One more question on AI before we switch off. You talked about two things, having members state annual goals related to AI. So I'd love an example or two of that. And then also you talked about doing AI Spotlights in every meeting, so I would love an example of that also. Sure.

Jennifer Cannizzaro [00:41:34]:
Okay. Goals. So it's really it's particular to, you know, a function someone is leading. But it's, it may be around capacity or use case or simply like exploring and adopting something in a platform. So that's kind of like the broad level around it. Also some people have written goals around just learning that they're going to do for the year. And that's fine and good by me because this is not just about like, hey, my goal is to apply this to these different areas or to get this thing done faster. It's also for me to like build something new or take a course or whatever.

Jennifer Cannizzaro [00:42:17]:
So I do like to see a mix of kind of both and like output. But also, you know, how are you investing in yourself? And you know, depending on the level, people may articulate those a little bit differently. So that's kind of broadly. I mean, the other thing is in the context of our go to market, it shows up as well and what we're doing for AI, but in terms of like how are you adopting the tools? That's kind of how we've done it in the context of goal setting. And the other one you asked about was. Oh, the spotlights.

Matt Carnevale [00:42:48]:
Yeah.

Jennifer Cannizzaro [00:42:49]:
So I mean these have ranged. I had somebody showcase how they built an agent to really better understand a particular Persona. I've had people highlight how they are using different LLMs to kind of like compare across the board. We even did a session as a team where we reverse engineered what do we think our customers are asking in these different LLMs to try to get a better sense of, you know, oh, what content are they drawing from and how does performance work vary if you're, you know, in perplexity or Claude or Chat GPT. So it's quite far ranging in terms of what we can actually spotlight. And so sometimes it might be like a particular prompt that's been really valuable. Sometimes it's comparing output across, you know, a set of LLMs or building an agent or something like that. So it's really meant to inspire and help people learn.

Jennifer Cannizzaro [00:44:00]:
And frankly I learn a lot from these because the way that I'm using it, it's going to be different than the way that you're using it. And our advocacy and reference lead is using it for something entirely different than a product marketer. But they might be able to build off of one another.

Matt Carnevale [00:44:17]:
Cool. All right, so we're almost up on time. I have one more question for you. You've had a good run at, you know, multiple legitimate companies. I know you've been a part of Chief and I know you're part of Exit Five CMO club. What role has mentorship and community played in your career growth, if at all?

Jennifer Cannizzaro [00:44:41]:
Yeah, community is super powerful and I think the role that it's played for me is really in giving me confidence and connection. And so, you know, on that front it can be very easy to, when you're a high achiever, to go into a particular area and as exciting as it is to dive in or to take on a new role, it could be scary at times. And so to know that there are other people who've been in your shoes and that like, hey, actually you're really smart and you're doing a great job or even to just frankly get outside the walls of your, you know, your day to day to understand that other people have similar problems, people are, you know, addressing them in different ways is really helpful. I, I, what I've learned over the course of my career is actually the more that I can invest in time outside of, you know, the boundaries of my organization, the better I am at my job. And so that's really where I've put more focus over the years. I think when I was younger, I didn't recognize it as much. I was like working these 12 hour, it was literally in the office like nine to nine, ordering dinner at my consulting firm and I would go to bed, wake up and run and like do the whole thing again. And it was so narrow minded.

Jennifer Cannizzaro [00:46:12]:
And compare that to current day where I actively find and make the time to invest in round tables and one off coffees and you know, mentoring, advising, starting to dabble in investing, that sort of thing because I want the broader perspective. It brings more meaning to everything and it just sparks so many different ideas to be able to, you know, go outside my comfort zone and connect with other people who are maybe solving the same problems, may maybe dealing with some different things. And it also allows me to give back because I've gotten so much from others in my career that knowing that I'm a part of something bigger and that maybe I can, maybe I have some wisdom to impart to someone is actually really gratifying.

Matt Carnevale [00:47:07]:
Cool. All right, well, Jennifer, this has been so incredible. You gave us so much good knowledge. I have so many more questions, but unfortunately I can't ask them all because we only have so much time. But yeah, I appreciate you coming on. I appreciate all the great advice and I'll see you around.

Jennifer Cannizzaro [00:47:21]:
All right, thank you.

Dave Gerhardt [00:47:26]:
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