#266: How to Lead B2B Marketing for the First Time: Strategy, Budget, Team, and Content with Jess Cook

#266 Marketing Leadership | In this episode, Matt is joined by Jess Cook, Head of Marketing at Vector, a platform pioneering the contact-based marketing category. Jess has spent her career building standout content strategies at B2B brands like LASSO and Fastly, and she recently made the jump from Head of Content to first-time Head of Marketing.

Jess and Matt cover:

• How content marketers can transition into marketing leadership and what gaps to prepare for
• The strategy behind building a brand that stands out in B2B (and why Vector leans into being “a little unhinged”)
• How Jess built her first marketing budget from scratch and sold it in using storytelling, not spreadsheets

You’ll walk away with tactical insights on running a modern B2B marketing org, from content and brand to budgeting and team structure.

Timestamps

• (01:00) - – Jess’s B2C roots at McDonald’s and Kellogg
  
• (04:34) - – Jumping into B2B and growing through content
  
• (06:19) - – Why she moved from Head of Content to Head of Marketing
  
• (08:54) - – Hiring product marketing first (and why it matters)
  
• (13:04) - – How Vector built a bold B2B brand with personality
  
• (17:04) - – What Jess looked for in her first marketing hire
  
• (20:24) - – Building and pitching her first full marketing budget
  
• (25:49) - – Creating a 30/60/90 plan that actually drives buy-in
  
• (27:19) - – Category content, SEO, and early wins with AI
  
• (32:20) - – The podcast pivot: ditching “Funnel Cake” for something better
  
• (36:00) - – How she knew Vector was the right fit
  
• (39:40) - – Going all-in on YouTube and video-first strategy
  
• (43:50) - – Short-form content, brand building, and trust
  
• (46:20) - – Biggest lesson: balance long-term planning with quick wins
  
• (50:50) - – Leading with action and setting the tone as a new marketing leader
  
• (52:50) - – How Jess communicates vision and builds internal alignment
  
• (56:20) - – Wrap-up and final takeaways

Send guest pitches and ideas to hi@exitfive.com
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Dave Gerhardt [00:00:00]:
You're listening to B2B marketing with me, Dave Gerhardt.

Matt Carnevale [00:00:17]:
On this episode of the Exit Five podcast, I speak with Jess Cook. Jess Cook is the head of marketing at Vector. Previously she was the head of content at multiple brands like Lasso. I lend fastly. And in this episode we talk about her transition from being a content leader to a marketing leader. We talk about how she made her first hire ever and the things she looked for. We talk about what big bets she's making from a content perspective and specifically the bet she's making on YouTube. And then we also talked about how she made her first marketing budget and what that process was like.

Matt Carnevale [00:00:52]:
So if you're somebody who wants to learn more about content strategy, about running a marketing team, or especially as a first time head of marketer, this is a great episode for you. All right, I'm here with Jess Cook. Jess, how's it going?

Jess Cook [00:01:06]:
It's going great. How you doing, Matt?

Matt Carnevale [00:01:08]:
Doing good, Doing good. It's funny, I. I think we. When do we meet or when do we first start interacting? It's been a while. It's been a while. Maybe like a couple years.

Jess Cook [00:01:16]:
Maybe two, three.

Matt Carnevale [00:01:17]:
Two, three years. Yeah. And I remember something funny. I remember when you and I first started posting on LinkedIn. I think it was around the same time. And I remember I had liked, you know, I always been liking your stuff, you were liking mine. And then I kind of like fell off the face of the LinkedIn Earth for about three to six months. And then I came back and I saw you again and you had like 10,000 followers.

Matt Carnevale [00:01:38]:
And I was like, damn, I really should have stuck to it. Like it was like the same time we started. I just stopped. And then you kept going. And I saw your ascent and I was like, oh, I guess that's why you don't quit things early, right?

Jess Cook [00:01:49]:
So that compounding growth, man.

Matt Carnevale [00:01:51]:
Yeah, that's it. That was a good life lesson for me. Cool.

Jess Cook [00:01:55]:
That's awesome.

Matt Carnevale [00:01:55]:
Well, today I know recently you're known on LinkedIn for your content takes. You were a head of content for a big part of your career. Recently you transitioned to head a marketing role at Vector. So I want to talk about a bit about that transition. I want to talk about, you know, what you've learned along the way. But for those who don't know, Jess Cook, why don't you give us the brief background as to who you are in your journey?

Jess Cook [00:02:20]:
Yeah, well, I have a kind of a crazy path to where I got to today. I started out as a copywriter on B2C brands. So my first job out of college was on the McDonald's account as a junior copywriter. And I wrote jokes on happy mailboxes. I wrote headlines for McDonald's billboards. That was kind of where I cut my teeth in terms of like, copywriting and messaging and branding. And from there I spent 15 years as a copywriter and creative director on still on B2C brands. So I did a lot of Kellogg work, Rice Krispies and pop Tarts and Frosted Mini Wheats, all of those kind of fun, like the cereals that we all know and love from when we were kids and Kimberly Clark brands as well.

Jess Cook [00:03:06]:
So Cottonelle toilet paper. I did this whole crazy campaign that had millions and millions of views about like, do you roll over under. We called it the roll poll.

Matt Carnevale [00:03:17]:
That's a good debate.

Jess Cook [00:03:18]:
Yeah. Hey, people have very strong opinions about that. You would be shocked. So that was a really, really fun part of my career. I learned a ton just about, like, simplicity in writing and how. How to build emotion into things that don't always have emotion involved, like buying toilet paper.

Jess Cook [00:03:38]:
Right.

Jess Cook [00:03:39]:
Or a hamburger. And in 2019, I decided I wanted to take that skillset of storytelling, content creation and go in house and try something new. And so that was kind of when I made the move to the dark side of B2B. And I've been doing SaaS content marketing ever since. I did, just like you said, make the jump from head of content to head of marketing at a company called Vector. And we are a contact based marketing tool, which is kind of a new category that we're building, which is really exciting. Getting a level deeper than account based marketing. Actually seeing the person level, kind of intent and information so that you can target the right people who are actually using your product and making buying decisions and tailor the messaging to.

Jess Cook [00:04:28]:
To their specific needs and intent.

Matt Carnevale [00:04:30]:
Very cool, Very cool. Awesome, awesome, cool. I feel like whenever I thought of the good content marketers in the B2B circle, I always thought of your name, you know, always viewed you as a content person and obviously you still have that DNA at heart. But what made you want to now go in the head of marketing route?

Jess Cook [00:04:46]:
It's funny. If you would have asked me a year ago if I would have tried to land a role like this, I think I would have laughed. I thought I would want to be head of content forever and ever and then maybe kind of go off and do my own thing. But I think it was part. I was ready for kind of the next step. I was feeling kind of this new sense of confidence that I stood up content at multiple places. I feel pretty strongly that, like, I can handle content. You can give me kind of any product to an extent.

Jess Cook [00:05:21]:
Right.

Jess Cook [00:05:21]:
And I can build content around it. I've built that muscle. But I also had this sense of frustration that, like, that was as far as my purview could go, that when it came to larger strategy, marketing strategy in general, it was much harder for me to have a say.

Jess Cook [00:05:39]:
Right.

Jess Cook [00:05:40]:
There's always someone else that has an opinion or there's someone who's been there longer, or maybe there's a marketing leader who just prefers demand gen as an approach over kind of organic content. And so they kind of use usually side with that part of the marketing or Great. So there was definitely, like a sense of frustration of not only have I, like, earned the right to have an opinion around that, but I wasn't being heard and I wanted to be the one to call the shots. And it was actually, it's funny, like, my husband was actually the first one to be like, I think you should stop looking for head of content roles. I think you should just start looking for head of marketing roles. And we kind of came to that conclusion that, like, yeah, that is actually the better next step for me. Like, I want to that new challenge. And so it was actually right around that time where Josh, the CEO at Vector, reached out to me because of our mutual friend Dan Murphy from Exit Five.

Jess Cook [00:06:35]:
Shout out to Dan Murphy, who said my name in a room of opportunity and put me forward as a potential candidate for that role. So forever indebted to him because here I am.

Matt Carnevale [00:06:46]:
Amazing. I mean, I feel like in marketing now, especially B2B, like a good content strategy is just part of a good marketing strategy overall as. As long as the goals align with it. Rarely now is there a head of marketing who's not taking a swing at creating some kind of media engine or some elaborate content marketing strategy. So I guess two things. Do you feel like it's helped you a lot transition to this role? And then B, do you feel like it also biases you to want to focus more on content as opposed to, like, some of the other things that maybe you didn't have a hand in in the past?

Jess Cook [00:07:23]:
Ooh, that's a great point. Okay, to answer the first question, really, there is no marketing strategy without a content marketing strategy because you can't have a campaign that points to nothing. You have to have some sort of, like, fuel in the engine.

Jess Cook [00:07:39]:
Right.

Jess Cook [00:07:40]:
And so it felt like. And I'm seeing this more now where heads of content are becoming those marketing leaders because they have that skill, because they understand what makes not only a good piece of content, but like a good content strategy, a good narrative. What are the things we need to tell the market? What are the trends that are happening right now that we can capitalize on? Content marketers are usually the best at connecting those dots and in that regard make a really natural marketing leader for the team overall. To answer your second question, I do think, yeah, I probably over rotate on content a little bit simply because that's what I know how to do quickly and efficiently and well. But I also know where my weaknesses are. And so my first hire at Vector was to bring on a product marketer, Alex Verdon, who was the product marketer at Metadata back in the day a couple years ago and really just created an incredible program there around product LED content and playbooks and what can the product do to help solve the problem. So between her and I, we have a really nice kind of like coverage, 360 coverage of top of funnel thought leadership kind of trend stuff. And then she kind of, as we get somebody into our universe is showing them what the possibilities are with Vector.

Jess Cook [00:09:02]:
So yeah, I think it's important to kind of do what you know and what you're good at, what you were hired for, but also know where like you, your capabilities kind of end and where you'll need someone to fill in those gaps.

Matt Carnevale [00:09:14]:
Yeah, totally. Yeah. I've always felt like product marketing is just the foundation of not only marketing, but just to go to market in general and without, even if it's not a dedicated in house product marketer. It's like someone in the company, even if it's the founder needs to be doing the product marketing. Is that part of the reason why you said you, you felt like maybe it was one of your weaknesses or something you didn't have the bandwidth for. Why did you hire the product marketer? Was it for that reason? Was it also because you see it as kind of that foundation to content, to the marketing strategy as a whole?

Jess Cook [00:09:47]:
Yeah, it's so foundational and I think it's really difficult to fuel sales the right way with the right content without a product marketer. And so it was funny. I think even in my first couple of weeks here at Vector I brought this up. I can do what I can do forever and ever, but I'm definitely going to need someone with this other skill set. So we can really. There's going to be very little overlap in Our Venn diagram of like what we do, and that's by design. I think it was really important to bring Alex on for the simple fact that we're going to evolve a lot over the next year or so as well, which means our messaging will evolve. And product marketers, that's usually one of their superpowers, right.

Jess Cook [00:10:30]:
Is like they can really boil down messaging to the simplest common denominator that still feels relevant to your audience. And so I knew we were going to need somebody who had had experience in messaging and positioning and really just simplifying the story that I could partner with to get us to a point that felt still interesting because definitely want to talk about that with you too. Just like how the vector, the brand is coming to life and really maintain kind of that liveliness that we have, but do it in a way that really elevates the product and its features and the value it delivers.

Matt Carnevale [00:11:09]:
Yeah, I love that. Let's get into that since we're on the topic.

Jess Cook [00:11:12]:
Part of the reason that I came to Vectors, I mean, I went to the website the first time and if you go to Vector Co, you'll see them. There's these little ghosts all over the website. And they're shorthand for this idea that like your website visitors are ghosting you, you don't know who they are and they can get away really easily because of that.

Jess Cook [00:11:31]:
Right.

Jess Cook [00:11:31]:
And they could have really high intent. They could be so super interested in your product, but if all you have is account level information, you can't really get to that. And so kind of a really nice little visual metaphor for what the product does. It's bright colors, the language is super clear and effective, but really fun. There's a little like our little demo call out in the bottom right corner is like, do you want to book a demo? And it's like coming from the ghost, right. It's just these little kind of surprise and delight moments. And I was like, oh, these folks know what they're doing. Not only are they building a category, but they're going to do it in a way where they're the most memorable of the category.

Jess Cook [00:12:14]:
And that was super exciting. So for us, it's like we're going to go big and bold and we never want to play it safe. And I think that's evident in our content all the way from top of Funnel down to the product LED stuff. So a couple examples. We just launched a product, a new view within Vector called Funnel Vision. And it really allows you to have X ray vision into the Funnel.

Jess Cook [00:12:37]:
Right.

Jess Cook [00:12:37]:
Hence where the name comes from. The idea is that you can see not only who is on your site, who is showing intent, who is researching, you know, the problem you solve off your site. You can see exactly where they are in the funnel. We have this nice little grid and you can kind of tell where folks are at, right down to, like, the product LED stuff. So Alex just. Oh, actually, let me back up a second. The launch graphic for that I was really proud of. I made it in Canva myself because small team and scrappy budgets, but it was like introducing Funnel Vision and it had the like, UI graphic and everything, but in the corners were these two little floating ghosts with lasers shooting out of their eyes.

Jess Cook [00:13:13]:
Right.

Jess Cook [00:13:13]:
What is going on here? That is what I wanted people to think when they saw that. So we're a little weird, we're a little unhinged, but I think you kind of have to be this day and age to get anyone to pay attention to anything branded. And then, like, right down to like. Alex just started a weekly newsletter where we're talking about, like, all the things that we're pumping out of the product every week.

Jess Cook [00:13:32]:
Right.

Jess Cook [00:13:33]:
We have features just coming out the wazoo every week, which is really exciting and we're trying to show that momentum. And her newsletter was called Ghost to Market.

Jess Cook [00:13:42]:
Right.

Jess Cook [00:13:42]:
Like all the things that are coming to fruition. So we want that to play out in every facet of our communications. And yeah, I just think it's so important now. You cannot be boring. The worst thing we could do is boring. Blend in.

Matt Carnevale [00:13:58]:
Yeah, totally. I feel like when you first joined, not saying there were not strong product marketing fundamentals, I also. No. No insight into what Vector is doing in that sense. But it's cool how when you first spotted them, you like that it was a fun brand who seemed to be approaching it differently. And now bringing in Alex also helps you kind of ground that funness in some fundamentals.

Jess Cook [00:14:22]:
Totally.

Matt Carnevale [00:14:22]:
How did you make sure that that wasn't lost in the process? Like, how are you making sure Alex is still bringing that funness to market while talking about boring things? Or maybe not boring things to some people. Like the newest product feature in Vector.

Jess Cook [00:14:37]:
Yeah, so a couple things. I. I knew that she had done that at Metadata. Metadata had a really interesting brand as well. A little bit more kind of forward and direct. So I. I knew that she had dealt with that before, like actually bringing brand to life and product LED content. I knew she could do it.

Jess Cook [00:14:55]:
The kind of other half of that is just giving people the room to do that. So give them the guidelines, create that tone and style guide and like, hey, here's kind of what we are and here's what we're not. We're always going to be fun, but we're never going to make people feel like they're not doing something right. We're just providing them this kind of new technology to do something new and interesting and we're giving it to them in kind of a fun, silly, a little bit unhinged way.

Jess Cook [00:15:21]:
Right.

Jess Cook [00:15:22]:
And she just kind of took that and ran with it. I think my directive to her was like, if you think it's right, you can just do it. I wanted to hire someone that I, I knew I didn't have to handhold. She's like the epitome of that. She's incredible. And I knew that if I gave her little to no leash, she would just be able to execute and do it in a way that like she knew was right. And I didn't want her to have to ask permission to do do the things that she knows instinctually as a product marketer of her caliber is right. But a lot of that comes down to hiring, right? Like, you know, for our, as small as our team is, we interviewed a lot of folks for that role.

Jess Cook [00:16:02]:
I was very diligent about getting like feedback on each person from previous managers. You know, I was looking for top 1% marketers because I knew to bestow somebody that responsibility of not only like creating great product marketing, but doing it in a way that the brand could shine through is a tall order. But we've absolutely found that in her and spades.

Matt Carnevale [00:16:24]:
Very cool. Okay, awesome. All right, so as a first time head of marketing, we talked about hiring, which is as a head of content? I don't know, did you hire anyone as a head of content or were you always pretty much solo?

Jess Cook [00:16:38]:
I was always pretty much solo and I would bring on vendors or freelancers. But yeah, that was about it.

Matt Carnevale [00:16:43]:
Got it. Okay. So that's like the first thing as head of marketing. Now you're hiring and you seem to actually have a pretty good grip or handle on who you needed to hire and like going for the top 1% and actually landing a rock star. So that's a good, good one for one right there. But totally. What are some other things like outside of hiring that have been surprising as a first time head of marketing? Where do you see your own gaps or what are things you're realizing now that you didn't realize when you're on the content side?

Jess Cook [00:17:07]:
I Just presented my first full marketing budget and let me tell you what a roller coaster that was. It was a lot of fun. I learned so much. I've had content budgets in the past, pretty healthy ones as well. So I understand how to run a budget and how to document spend and make sure that projections and actuals and all of those things align. But when it came to, like, okay, for all of marketing, we need to know how much money you're going to spend on what and why. That was like, oh, where do I even start?

Jess Cook [00:17:41]:
Right?

Jess Cook [00:17:42]:
Where I started was probably not the right place, right? Which is just like, let's just put some numbers on a spreadsheet and see where I end up. But again, you have to start somewhere. Where I ultimately kind of went to was, okay, knowing what our goal is this year, how am I going to back into that number? And what does that kind of look like in terms of, okay, we're going to have to create some content, we're going to have to put some budget behind that for paid.

Jess Cook [00:18:10]:
Right.

Jess Cook [00:18:11]:
But really where all that started from was like, not only do we have a goal in terms of revenue, but we also have a goal for the brand. We want a certain number of people to recognize who we are. We want branded search to be at a certain point. We want free signups to be at a certain point. What was really difficult was because we're such a new company, we don't have historical data on that. We don't really know what that could look like with any amount of money put behind it in marketing. So these are all really, like, best guesses and kind of gut feelings. And just based on what I know I've had in the past to work with and what's probably not enough, what I think will be enough.

Jess Cook [00:18:55]:
Right.

Jess Cook [00:18:56]:
Once I got all of that down on paper, actually, again, I'm going to bring Dan Murphy back into this because he's my advisor at Vector. He's amazing, as I know you know. So I got this all down on paper and I put it in front of him and I was like, this is the first time I've ever done this. Like, I need any null feedback you have. And he was one, so supportive. But two, he was like, you need the story around this. Like, you need to tell them why you need this money. Like, don't just put a spreadsheet in front of them.

Jess Cook [00:19:21]:
Build the story. And after he said that, I was like, it's so obvious now. I would do that with anything else. I would pitch right if I had some Kind of crazy content idea. I would tell them, like, why this is important and why it needs to happen right now and why this idea. But for some reason when it came to the budget, it like didn't occur to me. And so what I did was I put a deck together that was like, here's the story of this budget. These are the big bets we're going to make.

Jess Cook [00:19:46]:
Here's why those, you know, it was like three big bets. Why these three big bets are really important, what we think will happen if we make these big bets, and why they need to happen this year, like in the next six months. And that was one really fun to put together, like as a content person, as a storyteller, like, that was way more fun than the actual budget. But what it did when I actually presented the budget to Nick and Josh Vectors co founders was it got them excited to like hand me money. And I think that was kind of the unintended consequence that I, I wasn't thinking of when Dan suggested this, which I'm so thankful he did because now. Hey, new skill unlocked. One, I know how to put a budget together. Two, I know how to like build a story to sell it in.

Jess Cook [00:20:35]:
So yeah, that was a big new, like, thing for me to try and, and overcome.

Matt Carnevale [00:20:40]:
Yeah, that's a big one. I remember in my last role, I didn't have any direct reports at the time, but I was the marketing manager for the North America section of our business. And I remember I needed to put a budget recommendation forward and I was just like, when you actually sit down and you have to do it, it's like, wait, like, where do I even remotely start? But I like how your process was like, okay, I'm just going to start somewhere. I'm going to put numbers on a piece of paper and I'm going to let the confusion of that guide me toward the next thing. Yes. And I think it's smart. How? I think that's like with anything, you just need to like get started even if the thing sucks and doesn't make any sense because then you're forced to correct it and do it better. I like how you went to somebody who has done it before, like you, you leaned on Dan.

Matt Carnevale [00:21:27]:
I think that's such an important thing for first time marketers. You always feel like you have to do it alone.

Jess Cook [00:21:32]:
Yeah.

Matt Carnevale [00:21:33]:
Because you have to be smart enough to know what to do. It's like, I'm in this role now and, and I'm a market head of marketing and I need to know how to put a budget together. But in reality, like even if you're a second, third time, it could still be really confusing because for every company and industry and business type, it's different. So I think it's smart that you went to somebody and then after that, the piece about making it into a deck and telling a story out of that is huge. The reality is nobody really knows how to put the budget together, what's going to come from it. Even if it was like the co founders themselves, maybe they would even have a totally different idea or conclusion as to what the budget could be. But if you could tell a good story as to what it is, it's almost like raising money for a startup. The story is really what gets the money in your pocket.

Matt Carnevale [00:22:12]:
It's not so much what the spreadsheet says or what the number is.

Jess Cook [00:22:16]:
Absolutely, yeah. And just like two little follow up points that I want to double click on is I brought that budget to one other person as well. We're going to put a decent amount of money in paid ads over the next half of the year. Like if we want to survive, not even survive, if we want to grow the way we want to grow, we have to put a decent amount of money into paid ads, awareness, conversion, all of those things. And so I went to my dear friend Susan Winograd, who she and I have done a podcast together. We used to work together. She was the other half of the marketing department with me at a company called Mar Pipe. And I knew she would be able to help me out with like, how do I weight paid media? How much should go toward awareness, how much should go toward conversion? Or like competitive displacement? How much should go toward content distribution? Like I know all those things are important, but 10% here, 20% there, 70% over here, like how?

Jess Cook [00:23:09]:
Right?

Jess Cook [00:23:10]:
And so she had some really great points pointers for me. So my advice there would be like, shop your budget around to people who have expertise in the individual areas that your budget encompasses. Because that was like mind blowing for me to hear one. Just the ease of which she spoke about like, oh yeah, just do this, this and this. This is why you want to do that. But just getting that second opinion will be super reassuring. And then I also wanted to just double click a little bit on like the story itself. Because you people could be like, well, what does that even mean? Like, give me an example, right? Because that could be pretty vague.

Jess Cook [00:23:42]:
So I opened with a gif of like Rocky the movie and he's in his training montage and I was like, we're Rocky in the training montage right now. We're fit, we're excited. Everyone's rooting for us, everyone's talking about us like, we have this momentum, and now in the next six months, we have to step in the ring. That got them really pumped up. Like, who doesn't get pumped up over Rocky? But that was really exciting. And then the second kind of slide was I went back to when I was trying to get this role. I put together a 30, 60, 90 plan for Josh and Nick. Wasn't something they asked for.

Jess Cook [00:24:16]:
I just wanted to show them how excited I was about this role, and I wanted them to see how I think. And so I put this plan together, and it was three phases, and the first one was Sponge, codename Sponge. I wanted to soak everything up and learn as much as I could. The second phase was codename Scaffolding. I wanted to build all of the things that needed to be built, systems, processes, documentation, so that we could, like, move from a really good foundation. And then the third phase was codename Ninja Kick. And that was like, we're going to roundhouse everyone in the face with, like, vector awesomeness, right? Like, we've soaked everything up, We've built the foundations, and now we're going to go take what's ours. And so I took a screenshot of that codename Ninja Kick, and I put it in the second slide, and I was like, this is where we are, right? We're Rocky in the montage, and we're moving into.

Jess Cook [00:25:06]:
And I know Rocky's not a ninja, so excuse me, excuse my, like, unparalleled metaphors here, but we're moving into Co Ninja Kick. And, like, get ready, because remember how excited you were when you saw this plan initially? We're here. And so that was enough to get them excited for, like, the next parts, right? Which are, okay, here's the money I need to do this, which can cause your founders and your leadership team a lot of, like, heartburn. But if you can get them excited about where you intend to take them, it can help a lot.

Matt Carnevale [00:25:32]:
Yeah, okay. Love it. Love it. That's a great point. So let's talk a bit about. I want to talk about your content strategy, specifically. Just because, you know, content's your jam, we're talking about where you're making big bets right now, what you need the money for. What's part of the content strategy today? Like, what are some of the areas that you're focused on?

Jess Cook [00:25:51]:
A few things. So first is we're building a category So I need really foundational content about what this category is and kind of all of the initial questions that come up that might pull somebody into the vector universe. So I've brought on an agency who I know and love, I've worked with in the past. Their name is Aircule and they're an organic content systems agency. And they're helping me build all of that content that's going to help people kind of learn about the problems that vector solves, not only through organic search, but also in generative AI, because that is the new thing we have to start thinking about now. Actually just did a post about this this morning about like, hey, when you were building a category, the easy part is to sell the product. The hard part is to actually sell this brand new concept, whatever it is your product does. And so brought them on to really help me build a library of content that does that.

Jess Cook [00:26:48]:
And we've seen some initial wins, which is really exciting. So for instance, we put out an article that is just called what is contact based Marketing? Because it was something we were seeing, not a ton of volume around yet, but, but enough to warrant a really nice article on it. And two weeks after we published was the top search result on Google. But it also powered Google's AI generated answer and Perplexity's answer on the same question. So that was kind of a nice early win to see, like, okay, this is working, right? To share with the team who again sometimes has heartburn about investing in an agency like that. And like, what is this even going to get us? That was a really nice early win. And then there's like the flip side of that where if that's kind of the foundational stuff to build a pool of awareness and bring people into our universe and our website, the other end of that is like, how do we get people to favor us? So not only are we educating, but we're exciting to them. We're the brand they want to choose when it's time for them to choose.

Jess Cook [00:27:52]:
So I also wanted to have a really strong video first content strategy as well. And so we started our own podcast, just launched last week actually.

Matt Carnevale [00:28:02]:
Congrats.

Jess Cook [00:28:02]:
Thank you. And it's called this Meeting could have been a Podcast. And the idea is that you're dropped right into my one on one with my CEO Josh and we're discussing all the things that we discuss and have to make decisions around on a day to day basis. And it has very little to do with our product. In fact, that was one of the guardrails when I was Building it was. I didn't want it. I didn't want to talk about our product very much, if at all. I just wanted to help marketers and marketing leads think through some of the decisions they have to make with their CEOs and their founders and be able to see how someone else is doing it.

Jess Cook [00:28:42]:
Right.

Jess Cook [00:28:42]:
The whole kind of building a public thing, we really took that to the extreme. So one episode out so far, but it's already powering a ton of content for us. A newsletter, social content on the website, talking points for opportunities like this, which is awesome. And we've already gotten just really good feedback on it that like, yeah, this is the kind of thing I want to hear about. Right. Like, it's fun to hear how other people think about the problems that we all have to try and solve in some way, shape or form.

Matt Carnevale [00:29:14]:
I love that I have a couple follow ups, but I, I really want to double down on that one. I feel like, and I've been guilty of this too in like all my previous roles, just starting to see the light of it. But I feel like whenever people think about their podcast or their content strategy, they think about it in the box of their company and say, okay, I, we sell this solution. So the podcast must relate to the problem that we are trying to solve in that space, which isn't necessarily a bad idea, but everyone's doing that and there's a lot of noise there. What if you just create some kind of media asset that is going to be interesting to the people that you want to speak to? So in your case it's heads of marketing or marketing leaders, I'm assuming. So maybe you just stand up a meme TikTok account, which talks about all the funny things about being a first time head of marketing. Right. Like that could be an example of something.

Matt Carnevale [00:30:04]:
Yeah, Matt, there you go.

Jess Cook [00:30:07]:
There's our jump to TikTok. I love it.

Matt Carnevale [00:30:08]:
There's that number two. Yeah, that's it. But you know, things like that, like you can really stand up anything that's entertaining enough or slightly entertaining and educational at the same time to your audience. It doesn't have to be so down the narrow path of like what your product does. So I think that's a really, really, really smart move because that's something that people might just want to listen to casually when they're really not in the mood to like get into the nitty gritty of something or get super technical. Difficult. Right?

Jess Cook [00:30:38]:
Totally. And it's funny you say that because the first iteration of this podcast was a completely different show. And it was. It was called Funnel Cake. And we were going to try and, like, talk about, you know, modern day marketing. What does that look like? How do you pull people down the funnel? And inevitably, every time we went to try and outline an episode or, like, talk about the show and, like, how it was going to come to life, we kept coming back to, like, talking about the product. And eight days before, Josh, my CEO and I flew to Florida to film this thing. I got on my one on one with him and I was like, I think we have to scrap this.

Jess Cook [00:31:15]:
I think you need to give me 24 hours and I'll come back to you with a better idea because it's too close to the product. It's not going to build trust. Everyone's going to feel sold to. And he was like, okay, I think you're right. Good luck. I had to kind of put my back against the wall a little bit to, like, force myself to come up with something better, something more valuable. And that was how this meeting could have been. A podcast was born.

Jess Cook [00:31:37]:
So sometimes you need to get the wrong thing down on paper, like you said, with the budget, right? Like, just get something down and you'll know if it's right or wrong. And don't be afraid to, like, kill it if it's wrong. No matter the deadline. There's this thing called the sunk cost fallacy where everyone thinks because you've spent so much time on the thing, you have to move forward with it, and it's just not true if it's not right. You have to have kind of that come to Jesus moment where you're like, all right, we're eight days from shooting this, or, you know, we're four days from launch, or we're 48 hours from the event. And it's like, is this the right thing? And you have to make that call. It's hard.

Matt Carnevale [00:32:16]:
Yeah, it is hard. And it's funny because you always feel it somewhere in your gut. Like, you always kind of know when it's like, I'm not so sure about this thing. But like you said, you're rolling with it because you already spent three. Three weeks planning. And launch day is in three days. And it's like, well, we're just rolling with it and we'll adjust on the fly. But sometimes you have to just be okay changing your mind and changing it again and changing it again.

Matt Carnevale [00:32:38]:
Obviously, at some point you got to land on something and try it.

Jess Cook [00:32:41]:
Exactly.

Matt Carnevale [00:32:41]:
There's a balance. But it's okay to Change your mind. There's nothing wrong with that. We do it at Exit Five. We will literally sit down on a Thursday and be like, this is a direction we're heading in. And come Monday, we've all had some time to rest and sleep and think about it. And we're like, actually not gonna take that direction. Like, we're doing something different now.

Matt Carnevale [00:32:56]:
So especially in smaller companies, right?

Jess Cook [00:32:59]:
Yeah, it happens. Totally. And it's okay. And even with jobs, people do that with jobs too, where it's like, well, I've been here for three years. It's kind of the safe bet I'll keep going here. You know, it would be a shame for me to leave all that hard work behind, but not if it's the wrong thing, there's a better fit or. That's how I feel about this role. I'm so happy to have found this role, this company, a CEO who I jive with and who we can have a really respectful back and forth and dialogue about things, whether we agree or disagree.

Jess Cook [00:33:34]:
And I've felt stuck like that before and really have pondered, should I leave? I've been here a while.

Jess Cook [00:33:39]:
Right.

Jess Cook [00:33:39]:
If you're not going to be able to feel fulfilled and you have the ability to go look elsewhere, go do it.

Matt Carnevale [00:33:46]:
Yeah, I agree. Even if you end up making the wrong decision, it's better to get to another no or to move forward. Even if it's in the wrong direction. Right. Because then you go back. But how did you get that? You said you and the co founder really jived from the jump. You had, I guess, good vibes going into it. How did you suss that out?

Jess Cook [00:34:04]:
One, I really trusted Dan's opinion, knowing that he was involved in the company. And that was a big. They got a lot of points for that. But when I actually met Josh and Nick, it was a few things. Our values were very aligned. They're both excellent Air Force. They're always going to do the right thing the right way. They came from Drift, which was exciting.

Jess Cook [00:34:27]:
They've done this before. This kind of like, build a marketing tool to a very successful point and exit. So I knew that they had done this before and been successful. That was another big point in their corner. And then, like, Josh and I, we are like spirit animals. Like, we just, we could talk in gifts and, like, he gets my jokes and I get his, and, like, we're both a little off kilter. And that was really exciting for me. And just a couple weeks after I.

Jess Cook [00:34:58]:
I started, I even told him, like, this is the first time in a long time. I feel the same at work as I do at home. I feel like myself. And that was a big, like I've made the right move here because there's a lot of times where you go to work and you. We always talk about bringing your whole self. You just don't feel like you can do that for whatever reason. This is the first time in a really long time I felt like I could. And it's exciting.

Jess Cook [00:35:20]:
You do your best work that way.

Matt Carnevale [00:35:22]:
Absolutely. Yeah, absolutely. I feel it now with Exit Five. Ever since I started. It just doesn't really feel like I'm getting up and going to work. It's just like, oh, like I just, I'm going to do some work today. That's just part of like what my day is. It's.

Matt Carnevale [00:35:35]:
Whereas in the past it's like every day when you're approaching, you know, when you're about to go into your computer, it's like you have to hit a hard speed bump first and it's like it feels uncomfortable. Whereas this feels like I'm slowly going around the side of the speed bump and excited for the rest of my journey.

Jess Cook [00:35:50]:
Totally love that.

Matt Carnevale [00:35:52]:
Cool. One thing I want to circle back to is you talked about one of the bets is a video first content strategy. So you're doing this podcast, this great idea you have for this podcast, but what are you doing with the video?

Jess Cook [00:36:08]:
Love it. We're going to be YouTube stars. That's my hope. So I don't have a ton of experience with YouTube. I'm excited for that platform just as a growth lever. I think there's a lot untapped there as I'm sure your team knows, in terms of like B2B marketing. So we're going to invest pretty heavily there. We are obviously taking clips, using them in social.

Jess Cook [00:36:35]:
We're using it to power some founder led content specifically for Josh and myself. Sorry, I'm obviously not a founder, but executive content.

Jess Cook [00:36:43]:
Right.

Jess Cook [00:36:44]:
So Josh and myself and we're using it also to just power written content. So we'll do a really nice summary of this last episode or this first episode. There were kind of two streams in there which was bringing on an agency and the other side of it was like SEO Geo and like how we're approaching that. And so we were able to get like two really great summaries out of that, like what are the top takeaways with clips inside. So nice, like multimodal experience. So it's powering a lot for us, which is really, really exciting. And fun. It makes the storytelling easier because I know now for the next 16 weeks what we're going to be talking about, right? We've got eight episodes total.

Jess Cook [00:37:27]:
It's going to be every other week. I kind of know the mechanisms we're going to use to push everything out, but at the same time I want to watch and see like, okay, Josh's social is really like the big driver of engagement with these clips. Or the newsletter is really a great source of people are opening and learning and they're replying. So I don't know yet. I'm not really sure, like, will we keep that same mix? But I'm excited, I'm excited to learn and I'm especially excited to learn more about YouTube, what works there, what doesn't, and become a YouTuber. It'll really impress my 12 year old.

Matt Carnevale [00:38:01]:
There you go. Yeah, that's every, every, everyone's dream now, right, is to be a YouTube influencer. So that's super smart YouTube. I've, we've talked about it internally a lot. We haven't put the resources behind it to like really go in, in it. But even with that being said, I remember when I first started at Exit five. Well, some background. I'm not a big social media person overall.

Matt Carnevale [00:38:23]:
Like obviously on LinkedIn, I, I write a lot and engage a lot. But outside of LinkedIn, I, I'm not a big social media person. Don't have Instagram, I don't have any of that stuff. But one thing that I always consumed a ton of was YouTube videos, whether you want to put that in the same category or not. But I always found YouTube was part of my mix. So I had a bias toward YouTube. I always thought, you know, more B2B company should be on YouTube because I think it's a place that you can get a lot of time of someone's attention. And the thing about YouTube is you can do like edutainment, like you can talk about things that are related to your company and industry without being like extremely boring and technical and in the weeds leads like we talked about earlier with the podcast, like, you can create really good media assets that get a lot of attention from the right people.

Matt Carnevale [00:39:06]:
So I'm really bullish on YouTube. And I remember when I first started Exit Five, I was like, we should just take our podcast clips and just start putting them on YouTube and in YouTube shorts and that's literally all we've done and we don't have like a crazy amount of followers. I think right now we have like maybe it's somewhere over a thousand subscribers, which is like, it's not that many obviously, but if you look at our views every month, like we're easily raking in like thousands of views every month, like just those extra eyeballs. So it shows you, like the YouTube algorithm is just so superior when it comes to clip sharing that it's like that alone, even though it's really basic over time, like, I mean like over a year or so can be really powerful. But imagine if like you have a strategy that is actually YouTube first. I think you can do a lot of damage. There's.

Jess Cook [00:39:55]:
Oh, totally agree. It's funny, like in the first 48 hours we had 1400 views on podcast content. That blows my mind. And the, the vast majority of that came from YouTube shorts and something. I was, I was actually just talking to Devin Reed and I don't think he'd mind me sharing this little tidbit, but I asked him what was surprising to him about YouTube because I'm trying to get better at it and like, I kind of, I'd love to know like any secrets you have. He said something that was really surprising to him was people would come up to him or like send him a message and say, hey, I love your show. Like love your show, I'm a huge fan. And he'd be like, oh, well, like what episode is your favorite? And they'd be like, well, I guess I've only seen the clips in their mind by seeing a couple of 60 second clips.

Jess Cook [00:40:40]:
They watch the show and I thought that was really telling. People can be a raving fan of yours by watching a 60 second clip and feel like they're vested in the content you're creating. So I think that's another reason to be like really bullish on YouTube is you can push those clips out so much faster and get so many more eyeballs on them and become one of those kind of pieces of content people are consuming and become a fan of whether they watch the whole thing or not.

Matt Carnevale [00:41:08]:
Yeah, exactly. You can pull a lot of influence in 30 to 60 seconds in those clips, which is crazy. I mean that's, I'm not going to say one of the first, like that social media has always been big on short form and the ability to influence in that short period of time. But it's pretty crazy that you can take this thing that you may put a lot of effort into recording, chop it up a bunch. And now in those little clips, like you, you get a lot of influence and a lot of distribution, like so much by just putting it somewhere. And another reason why I think YouTube should be a big bet for a lot of companies is there's, there's just a deficiency there of good B2B content. Right? Yeah, it's how LinkedIn used to be five years ago. It's the reason why someone like Dave has like 200,000 followers on LinkedIn, because at the time there just wasn't many people doing it.

Matt Carnevale [00:41:54]:
Everyone was on LinkedIn just searching for a job or like posting weird stuff about their company. Right. It's like you just raised our series A congrats. You know, things like that.

Jess Cook [00:42:03]:
Like it was really boring for six months.

Matt Carnevale [00:42:05]:
Yeah, exactly. Go away for six months. And it was almost just like your digital resume. You left it there, you had a LinkedIn profile. It's just, it's good for job searching, but no one is really like sharing thought leadership there. And then, you know, people like Dave came by and changed that and they were able to get attention and traction really quickly, which was game changing for them. And I see YouTube as the same way today. There's a lot of people who have already figured that out in a lot of other different categories, but just not many people in B2B because it's, it's harder to see the longer road of the payoff.

Matt Carnevale [00:42:36]:
But there's a deficiency there and I think it's, it's a good bet.

Jess Cook [00:42:39]:
Totally hard. Agree.

Matt Carnevale [00:42:41]:
Love it. Love it. Okay, cool. Well, we're, we're coming up in the last 10 minutes. I want to talk about maybe some mistakes. So you've been head of marketing now for how long has it been? Maybe four or five months?

Jess Cook [00:42:53]:
Just over three months.

Matt Carnevale [00:42:54]:
Just over three months. Okay, cool, cool. So in your first three months, what I want to highlight are what are mistakes that you've made that, you know, maybe looking back now, you would tell another first time marketing leader, you know, hey, in your first three months, these are some things I would not do or some things I would not prioritize.

Jess Cook [00:43:12]:
So I think something that feels right to prioritize but is really hard to walk this line is balancing like long term strategy and short term wins. So you can't go too hard at one and not at all at the other and vice versa. You have to be able to show that you're here for the long haul and you understand kind of the vision and where we need to go to get there. But also especially, and this is especially true of a small company, like, you also have to show you can produce.

Jess Cook [00:43:43]:
Right.

Jess Cook [00:43:43]:
Even as a head of marketing Like, I'm writing blog posts, I'm writing social content, I'm using AI to create founder led content with Josh and Nick and Toe. So you have to be able to kind of show the breadth on both sides that you're able to produce.

Jess Cook [00:43:58]:
Right.

Jess Cook [00:43:58]:
So like, here's the content strategy that we're gonna go after for the rest of this year. But also, hey, I created this really cool workflow that's gonna take like your tone and voice and your post structure and we're gonna have 30 minute conversations every week and I'm gonna take those transcripts and I'm gonna dump them in here and now, voila. We have all these posts for you every week.

Jess Cook [00:44:15]:
Right.

Jess Cook [00:44:16]:
So you have to be able to kind of understand like what's going to move the needle in six months and let's plan for that. But also like, how can I get my CEO, my founders really excited with something that's really actionable?

Matt Carnevale [00:44:30]:
Yep. Yeah, Yeah, I love that one. Yeah. I think there's something about as quickly as possible getting some kind of win on the board, which is the short term part. It's like in your first week you're a content person. It's like in your first week, can you go clean up a couple of blog posts, can you go write a couple social media posts? Can you do something like really small and scrappy to get that initial trust? And you even talked about working with that content agency to get that article out, which got rose the rankings quickly. And it got featured in Generative AI, which that's an example of like you took this bet on this agency and you're pumping money into that every month, but you were able to show something really quickly on which helps build trust in the long term. And then the long term is the reason why you're doing the short term thing too.

Matt Carnevale [00:45:14]:
Sometimes the short term stuff can be like random one offs. But it's like you're doing the things that are feeding into the long term strategy because at some point you get asked about it, it's like, oh, like what's our vision for this? And it's like.

Jess Cook [00:45:28]:
Exactly. That's a really good point. That you can't just do some short term execution just to prove you can do stuff right. Like it also has to feed back into this vision that you have for like where we need to go and where we need to be. I think the big thing I did in my first week was I put a button on the homepage. Like we had one in the nav that led people to our free trial, but we didn't have one in the hero section, and it felt like we really needed one. Like, why isn't it there? That was like my big, exciting short term thing I did in my first week was I added this button to the homepage that got people to sign up for free trials, which, by the way, quadrupled the free trial signups, which was, you know, kind of exciting.

Matt Carnevale [00:46:10]:
That's pretty nuts. That's actually pretty nuts.

Jess Cook [00:46:12]:
It is pretty crazy.

Matt Carnevale [00:46:13]:
Yeah.

Jess Cook [00:46:13]:
Just the place of a button, you know, sometimes. So. But I did that because I knew we really wanted to start pushing that freemium model, right? That like, we wanted just to get people into our universe to sign up for the product, to get addicted to, like that contact level data. And then there's going to be some trigger points inside the product that are going to get them to upgrade. But first we have to get them into the product and just trying it. So I already knew that was going to be part of, like, the marketing strategy anyhow. And so I was like, oh, short term win button on the homepage. Like, let's just get this process moving.

Matt Carnevale [00:46:47]:
Yeah, I love that. I remember before I started at Exit Five, this was. I maybe had like a week buffer before I started. If. If even it was only like half a week. I was starting really quickly because they. They asked me if I wanted to start Monday. And I was like, I'm ready.

Matt Carnevale [00:47:03]:
And I remember I had literally, I don't necessarily recommend everyone do this. I'm not saying that you have to do this, but the weekend before, sometimes I'll do some work on weekends. So the weekend before, I created something that I was going to ship, like in my first couple hours of working, something that I know they wanted from speaking to them in the interview process. So the first thing, we had our team meeting first thing in the morning. Hey, you know, this is Matt. Yada, yada, yada. And then after that, within 30 minutes, I already had like some work that I shipped and was getting feedback on. And like, that work was nothing.

Matt Carnevale [00:47:39]:
What Dave or Dan wanted, like the feedback was like, you actually have to just like totally change the way you did this. But just the initiative of like showing I am down to do the stuff right away, like, I can get wins on day one. I think it changed everything going forward after that. They saw my. My personality going after that.

Jess Cook [00:47:57]:
Yeah, that bias toward action is super important because I've definitely been stuck places where I don't have the permission to have that bias toward action. You have to Ask permission before anything can go live. And that's a frustrating place to be too. So I think that's such a green flag that you were able to put something together and share it and get feedback on it and make those updates and edits to it that like, put it in the right positioning or built it into the strategy the right way. But like just the fact that you're at a place that allows you to do that, that definitely look for that as a green flag when you're. You're looking at a company.

Matt Carnevale [00:48:32]:
Yeah, totally. All right, well, last question. This is, this is based on what you had just said about long term strategy and how you're building that, having that department vision and foresight, it's a skill and it's a difficult one because you're essentially not only convincing the founders, that's one thing, but you're convincing the rest of the company. Right? You are the guiding light for marketing and you're trying to show everyone that my head screwed on right. I know my stuff and I'm leading us in the right direction. So what's that been, like, how have you went about creating that vision for the department and also talking about it to people and getting them excited?

Jess Cook [00:49:09]:
We have some really nice, like, company rituals every week. So we have like an all hands meeting every Monday where we talk through what we're committed to this week. And then on Fridays we have something called Friday Flex where we talk about like what we accomplished, what we missed on and what lessons we learned. So those are kind of the moments where it's really exciting and important to be able to share like the strategy or hey. Where we have to make a shift because this isn't working. But I think the really important thing is like, we have the freedom to talk about when we're making mistakes. In fact, we're encouraged to not just talk about the good stuff, like, what did we miss on this week and why and how can we learn from it? Because, you know, you can get to a point in a company where everything's rah rah and exciting and there's some stuff hidden under the layers of that rah rah excitement that are really going to affect the business and they get brought up too late. And so it's really nice to be somewhere where you can like, hey, this is something we missed this week.

Jess Cook [00:50:11]:
I kind of overestimated, like, what I could do on this and I'm going to need some help. And that is like, great. No one is going to be afraid to jump in, but if you don't bring that up until three weeks down the road, there's going to be some trust lost. So I do really love being somewhere where, like, we're encouraged to bring up mistakes, we're encouraged to talk about things that aren't working because it does build that trust. And it. I think that comes from the top down where the leaders are also talking about their mistakes, which makes it a lot easier for their. Their direct reports to talk about their mistakes and our direct reports to talk about their mistakes. So, yeah, I think those are really important ways to kind of bring that vision to life.

Jess Cook [00:50:51]:
I think we're also, like, we're trying to assemble a team of people who are practitioners who have done this before. That's why we hired Alex, because she's done this before. She has a great reputation, an audience on LinkedIn, which is really exciting. We need our employees to be our evangelists.

Jess Cook [00:51:08]:
Right.

Jess Cook [00:51:09]:
And now that they need to sell Vector, but they need to talk about what they're doing here. Go out and talk about all of the engineering. Go out and talk about why you're building it the way you are.

Jess Cook [00:51:18]:
Right.

Jess Cook [00:51:19]:
And usually as the marketing team, because we're comfortable with that, we have to be the ones to, like, model that for them. What does a good LinkedIn post look like? And how can you kind of transform that to be about, like, your specific area of expertise, if you're an engineer or you're in customer success or whatever the case may be? So I think you just kind of have to, like, lead by example. And I'm just really lucky to be in a place where, like, the example is set by leadership. And it's a great example because I've definitely been places where it's not totally.

Matt Carnevale [00:51:51]:
Yeah, same here. Same here. All right, well, Jess, this has been a great episode. I appreciate you so much for all the insights you've imparted. I've been following you on LinkedIn for a while, so if anyone wants good tidbits of marketing knowledge, content knowledge, Jess is a great follow. Highly recommended. I'm not just saying that because you're here. I've always thought that.

Jess Cook [00:52:10]:
Thank you.

Matt Carnevale [00:52:10]:
You, of course, of course. So appreciate it and we'll see you around.

Jess Cook [00:52:14]:
Thanks for having me. Matt. This has been, like, a full circle moment for me. I've been listening to this podcast for years, and so very exciting to be a guest. Thank you.

Matt Carnevale [00:52:24]:
Yeah, yeah, I knew it was weird that I looked back and you hadn't been on an episode. I was like, all right, this. This just feels right. So I'm glad we did it.

Jess Cook [00:52:31]:
Thanks so much.

Dave Gerhardt [00:52:36]:
Hey, thanks for listening to this podcast. If you like this episode. You know what? I'm not even going to ask you to subscribe and leave a review because I don't really care about that. I have something better for you. So we've built the number one private community for B2B marketers at Exit Five. And you can go and check that out. Instead of leaving a rating or review, go check it out right now on our website, exitfive.com Our mission at Exit Five is to help you grow your career in B2B marketing, and there's no better place to do that than with us at Exit Five. There's nearly 5,000 members now in our community.

Dave Gerhardt [00:53:08]:
People are in there posting every day asking questions about things like marketing, planning ideas, inspiration, asking questions and getting feedback from your peers. Building your own network of marketers who are doing the same thing you are so you can have a peer group or maybe just venting about your boss when you need to get in there and get something off your chest. It's 100% free to join for seven days so you can go and check it out risk free and then there's a small annual fee to pay if you want to become a member for the year. Go check it out. Learn more exitfive.com and I will see you over there in the community.

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