Jess gets promoted to VP
S3 #6

Jess gets promoted to VP

Jess: Hey, Josh

Josh: Hey, Jess. I've got some really exciting news for you. We'd like to promote you from our head of marketing to Vector's vice president of marketing.

Jess: Thank you, Josh. Thank you. I'd like to thank my mom and dad, my husband, Brandon, for liking every single one of my LinkedIn posts, our daughters for being the reason I do everything, my college marketing professor, Dr.

Jess: Atkin, for seeing the potential in me early on, my team, who couldn't be here today because they're doing all of the work.

Josh: Hey, Jess. Remember that time that you got promoted to our VP of marketing?

Jess: I will literally never forget that day. It was very exciting.

Josh: What day was it? Where were we? What was I wearing?

Jess: It was, like, December something. You know what's really funny is it was, like, early December, and you had told me, like, "Come January 1st, this is official."

Josh: Yeah.

Jess: And then it was, like, holiday season.

Josh: Yeah.

Jess: And, you know, spent time with the family and Christmas, and then we came back and you actually announced it- Yeah ... at our all hands meeting. And I was like, "Oh, yeah."

Josh: You had forgotten.

Jess: Forgotten one of the biggest thing that's ever happened to me in my career-

Josh: Yeah

Jess: over the holidays.

Josh: That was, uh, you had a particularly magical promotion because you, to your point, when we came back from the holidays it was our company kickoff.

Jess: Yes.

Josh: So I think you were, like, at the beginning of the company kickoff, like, deck for-

Jess: I was ...

Josh: for that day, which was-

Jess: And do you remember what you did?

Josh: We- I do. Do you wanna, do you wanna tell the story?

Jess: Sure. Yeah. Yeah. You took my ghosty, which is, um, modeled after Taylor Alison Swift.

Josh: Your close friend.

Jess: My close confidant and friend. My lifeti- lifelong collaborator.

Josh: And specifically it's a, it's a ghost wearing the heart glasses.

Jess: And a little flower crown from the, um, Anti-Hero video.

Jess: Yes. And you made it evolve like a Pokemon. Into this, like, insane, like, fairy-esque version.

Josh: We showed, like, the Pokemon animation, uh, animation- Yes. ... of, like, a Pokemon evolving, and then it was, like, Jess' previous ghost and then, like, the, the, the big beast one. The

Jess: suped-up ghost.

Josh: Pimp My Ride ghost.

Jess: That's so good.

Jess: Yeah.

Josh: Yeah, it was awesome. I think it would be really helpful to spend this episode talking about sort of, like, why I made that decision, and specifically kind of, like, what I saw from you and, like, what you had done over the, the year prior that made that such a, a no-brainer decision for me so that other marketers can kind of, like, learn from that experience and maybe exemplify some of the things that, that you crushed over the last year.

Jess: Go on.

Josh: Keep,

Jess: keep- Continue ...

Josh: talking. Yes. Okay. I have a list of things that were really impactful for me. Um, let's start with trust. So there's a question that gets asked to most leaders that is a really kind question, but the question is actually, um, a secret warning that the person asking the question is not ready to be a leader.

Josh: And it typically goes like this. It's in a one-on-one, and someone asks their boss, "What can I help you with?"

Jess: Mm. "

Josh: What can I be working on?" Like, "What can I take off your plate?" And it is such, like, a good-hearted question. Like, you, you know that that person doesn't have any mal-intent. But what you're actually asking me in that moment is, like, "Can you figure out what to assign me?"

Jess: Mm.

Josh: And you never did that. You came to me in our one-on-ones and you said, like, "This is what I'm working on."

Jess: Yep.

Josh: And I essentially, like- Almost got to go prioritize other departments and focus on other things. Can you, can you walk us through, like, sort of like how were you comfortable sort of like going and finding problems to solve versus asking for me to assign them to you?

Jess: Yeah. I think one of the most important jobs of a marketing leader is to make the CEO's job easier, and part of that is finding out what are the things that is going to make that CEO's job easier? What are the things they worry about, that they stay up at night, that they wish they could do in, with regard to marketing that they don't have bandwidth or experience or time with, but they know it would be really important?

Josh: Yeah, and I, I, 100%, you made my life easier, and I think one of the things that you were able to do that any aspiring marketing leader should pick up on is you almost made it your job to know my job, right? So, like, instead of being, like, a marketing leader, right, i- in order to know what to take off of my plate, you almost had to be a CEO, right?

Josh: You had to understand sort of like this is the problems the business is facing. This is where we are with product. This is where Josh's energy's being focused. Wh- when you were in our leadership meetings or all-hands meetings, were you listening for things differently than you were in, like, past marketing jobs, where you're only sort of, like, focused in on content or whatever it might have been?

Jess: Yeah, absolutely. That's a great poi- and it's funny 'cause I don't know if I realized that until you literally just said that. But yeah, I think when you're leading content, and that's kind of your microcosm, you're thinking, "What are the angles? What are the stories I can pick up? What are some of the insights that I can use here and maybe connect some dots?"

Jess: Yeah. And now it's more like, "Okay, he, he's clearly, uh, concerned about this," or, "This is something he feels like we're not conveying to the market well enough." Like, these are the things that we need to in some way, shape, or form, whether it's content or it's some sort of demand gen program or- Something that has to do with, like, product-led marketing- Yeah

Jess: um, we need to address. Yeah. And so yeah, I think you're seeing, like, just another altitude of what that means for the broader business.

Josh: Yeah. Yeah. I appreciate that. And I know at the end of the episode we'll probably talk about, like, your trepidations and the things that were hard. Oh, yeah. But I'm just gonna, I'm gonna keep you on the pedestal here- Okay

Josh: for a little bit. Uh- I'm

Jess: not gonna stop you.

Josh: To round out sort of this first thing, which is trust, I think one of the things that I was noticing in our one-on-ones that just, like, again, right, like, as, as a, as a CEO, I'm not constantly walking around being like, "Who's getting promoted," right? I'm, I'm operating the business.

Josh: Yeah. But then there's these, these things that you notice where you're like, "Oh, man," like, "This person deserves to be elevated." And the, the one that I kept feeling is our one-on-ones felt really different. And, and just for everyone that's out there's edification, like, a CEO, like, their job is to s- sort of, like, fly this 40,000-foot view over lots of departments, right?

Josh: So I go between you in marketing to, uh, to, to Nick as our COO, and he, as our sales leader now we have Heather Bell, uh, to Ali in solutions, Andrew in, in engineering and product, right? So I'm, I'm sort of touching all these different departments, and at any given time, like, there's only a handful of, like, problems I can focus on.

Josh: Yeah. Um, and for us as an early stage company, a lot of our problems are products and direction and all of that. And so the thing that built a lot of trust for me is our one-on-ones, um, they felt different, right? And, and it almost felt as if I was showing up... And, and sometimes I felt like I was ignoring you, right?

Josh: It was just sort of like, "Hey, I haven't seen you in a week. Like, we have 30 minutes. What's going on? What do you need my approval on?"

Jess: Yeah.

Josh: And we, like, our one-on-ones were like that for, like, months and months and quarters and quarters, and it started to dawn on me, like, "Oh, I'm not ignoring you. I just trust you so much-" Yeah

Josh: "that, like, this part of the business is operating by itself." Um, can you speak about how that felt? 'Cause I think some people would interpret, "Oh, I'm trusted and I'm an important part of the organization if I'm at the center of everything, and, like, I'm being spoken to all the time. Like, I kinda just, like, let you do your thing."

Josh: What did that feel like?

Jess: Yeah. Um, it, it's funny, because I think even just a couple of years ago I was very much a permission asker.

Josh: Yeah.

Jess: Like, I would go to my manager or, you know, whoever I needed to to, like, get the permission to do the thing that I knew was right. And I think very early on you had told me, like, "I just need someone to come in here, and if you know it's right, I just want you to do it."

Josh: Yes.

Jess: Um, and that, I really appreciated that, because I don't know that I, that level of autonomy has never explicitly been given to me in that way. Yeah. Um, there's always kind of this, um- I don't know, a little bit of a, "Yeah, I trust you, but, like, run everything past me."

Josh: Yeah.

Jess: Um, and I didn't feel that from the beginning, and I think it was partially like a, "Hey, I'm gonna give this to you.

Jess: I'm gonna give you this trust kind of unearned because I need to- Yeah ... for, like, probably your own sanity." Yeah. Um, and but at the same time, like, it's kind of a test. Like, I wanna make sure that, like, you continue to retain that trust with all of the decisions you're making. Yeah. And so I think I took it as just a, a, yeah, like a huge, um Like, vote of confidence that y- you felt like I was handling my, my shit-

Josh: Yeah

Jess: in the way that I needed- Yeah ... to handle it. But I also knew that, like, if I wasn't or you didn't agree with something, you would also come to me, 'cause we're, we're also very honest with each other. Yeah. I think that's a, a huge thing I appreciate as well. Yeah.

Josh: So you bring me to my second point, which is w- uh, of all the things that I saw, the second thing that made it a no-brainer to bring you into this role was track record.

Jess: Ooh.

Josh: Because I actually disagree with what you just said. I, I don't think that I am so unique of a CEO where I'm just like, "Oh, I, uh, I give so much autonomy, and Josh is just such a cool CEO." I think I'm a lot like the people that are listening right now that are, have asshole CEOs that, like, don't trust people.

Josh: Yeah. Like, you've seen me in other departments where, like, I don't have trust or I don't think, like, the ball's getting moved. Sure. Like, I'm a dick. So it brings me to- I'm gonna

Jess: withhold my statement there.

Josh: There's, your colleagues right now on your leadership team are, like, like, violently shaking their head up and down.

Josh: Yes, that is true. Um, but so, like, I want people t- listening to, to not think, like, "Oh, Josh just has, like, a cool CEO that gets marketing." Yeah, very true. Right? Like, the, the second thing that I wanna bring up is track record, right? Like, you, when you first got in the seat, like, I was watching, right? And there was this sort of like, a- as all first impressions are, there's this moment where you get the opportunity to, like, prove, is, like, this track

Josh: Am I gonna have a track record that, like, gives me trust?

Jess: Yeah.

Josh: And do you remember what you created as part of your interview process?

Jess: I do. It was a 30, 60, 90, uh, kind of, like, plan.

Josh: Yep.

Jess: Yep. Yep. And I gave it some fun code names.

Josh: Yep.

Jess: Yeah.

Josh: You, what was it, like, r- roundhouse kick, or-

Jess: Yeah ... what were they? So the first one was, uh, sponge.

Jess: Mm. Is where I was gonna soak everything up.

Josh: Yep.

Jess: The second 30 days was scaffolding. We were gonna build kind of the support things that we needed to move in marketing.

Josh: Yep.

Jess: And then the third was ninja kick. Ninja kick. We were gonna roundhouse everyone in the face with our awesomeness.

Josh: So you made this, like, 30, 60, 90 in your interview process.

Josh: Which, like, for, for most people, like, we've all had to do this- Yeah ... in roles. And the thing that was different about you is, like, you took not only that interview process so seriously, but you legitimately, like, brought it in to your day-to-day operating, which I don't think most people do, right? It's like they kinda separate.

Josh: Yeah. Like, "Yeah, here's my 30, 60, 90." Then we'll actually get in the company, you'll give me a bunch of directive, and I'll, like, throw it out the window. Yeah. Right? Um, you kept to your 30, 60, 90 day to a T. Like, those code names we were using- Yeah ... like, the next year.

Jess: Yeah.

Josh: Right?

Jess: Yeah.

Josh: Um. W- w- why? Like, w- like, why and how were you able to, to build this thing that you actually then went and executed on?

Jess: I built that 30 60 90 based on all of the things I always wished I could have done-

Josh: Yeah ...

Jess: as a content and brand leader in the past that I was not able to do. Like, for whatever reason, right? Like, I, I couldn't get leadership buy-in because they just didn't believe in content. I couldn't get a founder to, to start posting on LinkedIn because they, it felt cringe to them.

Jess: Yeah. And I was like, "This is my shot." Like, if I'm going to do this at this company, that I get the feeling is really gonna give me the ability and the autonomy and the trust to do these things, like, I'm gonna do it. These are the things that, like, I know if we do them, we will win. And it was just a matter of, like, I think this is the company where I finally am gonna, like, break through that, like, ceiling or whatever- Yeah

Jess: and like, get it to happen. Like, I could tell you and Nick were, like, up for anything.

Josh: Yeah.

Jess: And that was really exciting. And so it was just kind of like, one- once you and Nick saw that and you were like, "Yeah, this is amazing," and I was like, "Oh, my gosh." "I might actually make this happen," right? And then it was like, well, now, now I'm gonna do it.

Jess: Like, it- Yeah ... it was, I, I just wanted to. Like, I knew it was right. You know, and I think a lot of the things that were in there were, like, you and Nick posting consistently on LinkedIn. Yeah. Um, really understanding, like, taking the brand to kind of the forefront and making sure that we were, like, a brand first company.

Jess: Yeah. Um, that we weren't just kind of, you know, resting on, you know, like, product-led stuff or demand gen- Yeah ... only. Because when you, when you take all of that stuff away, like, all you're left with is brand- Yeah ... and affinity. Yeah. And if you haven't built that, like, you've got nothing.

Josh: Yeah.

Jess: When budgets get cut and you can't spend on those programs that typically, like, generate pipeline-

Josh: Yeah

Jess: all you have last, left is that brand. Yeah. And so that felt really important to me. And so it was very, like, highfalutin,

Josh: Yeah ...

Jess: high-level stuff. And when you all said like, "Yes, let's go," then I was like, "Okay, I'm r- I really have to make this happen now." Yeah. Because I believe in it so wholeheartedly.

Josh: The next thing I'm about to say is definitely gonna get clipped and put on LinkedIn Lunatics.

Josh: Yes. Call it. Uh, one, one of the things that I saw in you, oh, this is so toxic, but, like, it mattered a lot to me, is, like, you were stressed.

Jess: Oh, yeah ...

Josh: like, you, like, and I don't mean that in, like, the toxic- Yeah ... like, I want all my employees to work super hard. By the way, like, there are marketers out there that have leaders that suck- Yeah ... that are not giving the autonomy. Don't stress over your job. Yeah. Get your paycheck, girl. Yeah. Right? Like, you know what I mean?

Josh: Yeah. Like, you shouldn't stress for every job. But what y- I think, and you tell me, what I think you saw was like, "Oh, shit, I have leaders that are like m- might actually give me autonomy here. I can't fuck this up." Yep. And I saw your stress. I saw your anxiety. I, again, not to be toxic, like, I saw the hours that you worked, and I was like, "She's taking this real serious."

Josh: Yeah. Like, she doesn't wanna blow this.

Jess: No. I cared a lot, and I could see that this was my shot, right? Eminem. You only get one shot. Mom's spaghetti.

Josh: Mom's spaghetti. Can you tell Jess is from Detroit? Michigan. How far are you from Detroit? I

Jess: have an hour.

Josh: Yeah.

Jess: I have an hour from Detroit. I say Detroit 'cause it's like-

Jess: no one else knows Clarkston, Michigan.

Josh: You live in, like, a nice middle, upper class neighborhood.

Jess: I definitely in the suburb.

Josh: You don't know shit about Eminem,

Jess: Jess. So far away. Hey, I do love Eminem. Uh, we all do in Michigan. But anyway, um, I digress. So, like, yeah, this was my shot. And I was like, "Okay, I'm really gonna do this," and I, I just, I cared so much.

Jess: Yeah. And I could tell that this was, like, I was not gonna get this opportunity elsewhere. Yeah. And so, yeah, I was. Like, it was very much self-imposed stress. It was not anything that was put upon me. You sure? I just... No, it really wa- Like, I felt the pressure to, like, deliver for, like, everyone in the company, and the future of the company, and I was like, "This, this is the thing.

Jess: This is, like, this is what I could potentially be known for someday." Yeah. Right?

Josh: Um, bonus clip. Uh, we, uh, Jess and I, when we record this, we're, we're in Orlando. Yep. Uh, we will typically try to go to, like, Disneyland or something after. Or Disney World. It's Disney World. Disney World, sorry. Grew up in Southern California.

Josh: Um, but in between the days that we do recording, uh, we have a tradition where we bring our partners with us- Yep ... on this trip, and we go get dinner. Yep. Uh, last night, we got dinner, and my wife and I were, were walking away, uh, from Disney Springs. And, and sh- we were talking, and she's like, she's like, "I really like them," referencing, like, you and, and your husband, Brandon.

Josh: And I was like, I was like, "Me too. Say, say more, though. Like, what do you, what do you see?" And, and she said, like- Jess just has this, like, she brings, like, a light into the room, and she just brings this, like, positivity. And, and I couldn't agree more, but it's worth calling out because, like, the Jess Cook that you see on LinkedIn is, like, the Jess Cook that is, like, within the company, which is, like, you had a, a world of problems that you had to solve, right?

Josh: Like, I think it's very easy to, like, look at from the outside in of, like, "Jess just gets marketing," and, like, "Jess, you know, had this brand handed to her." That's not the case. Like, you had a lot of hard stuff handed to you. Sure. And I think a huge part of, like, bringing you further into the, your leadership journey was, like, seeing the poise and the positivity in which you attacked those things.

Josh: Thank you. So start crying on demand.

Josh: Okay, so getting back to it, one more thing before we get off of sort of track record. You made bets in the very early days of this company that, like, I would not have bets on. And they ended up being right. So talk me through, like, coming in t- as a, as a new marketing leader, owning a function, which you hadn't done in its entirety before.

Josh: Like, I think a lot of people would try to, like, make safe bets, like do some checklist marketing. You didn't do that.

Jess: No.

Josh: Walk me through that.

Jess: Again, I wasn't gonna squander this opportunity. Like, I think the very first thing I pitched to you was like, "We need to be doing a podcast."

Josh: Yeah. "

Jess: And it should not talk about the product at all."

Josh: You're like, "If I'm going down, I'm going down in flames, baby." I'm

Jess: like, yeah.

Josh: I'm gonna spend some budget as I do it. Oh my

Jess: gosh. Kamikaze. It was, like, the most, like, flamboyant- Shoo ... yeah, insanity. Um, yeah, and I think it was like, I, I knew it would work. I knew if we found the right concept, I knew that if we...

Jess: I could tell you and I already had great, like, chemistry- Yeah ... and working relationship very early on, and I was like, "If it's gonna work anywhere, it's gonna work here." Yeah. "And so we might as well, like, take that leap and just try it." Um, and I also kind of could tell that, like, you valued those big bets.

Jess: Mm-hmm. And that even if it didn't work out, like, we would all learn something from it- Yes ... and then try to find the next right thing. Yeah. Um, I never got the sense that, like, "Well, if this doesn't work out, that was it, and it was a fun ride." Yeah, yeah. Like, that was never the case. Um, but I think you just always, a- and still, like, still even with the entire company, it's like make big bets.

Jess: Yeah. Like, d- we don't do anything boring. We don't do anything safe.

Josh: Yep.

Jess: Like, again, my, my hypothesis is the most expensive problem right now in B2B is being forgotten. Like, I don't e- I want, I always want to be at the top of every marketer's list of, like, brands that are doing it right. Yeah,

Josh: yeah. I think, um, what you brought, I think the summary of, like, point number one and point number two, so track records and trust, was you brought a really strong opinion- Mm-hmm

Josh: of, like, what you thought was the right, right stuff. And even if there are marketers out there that are not working in companies that have neon signs- Yeah ... and Pac-Man, uh, in the middle of their podcast, um- Having strong opinions- Yeah ... if you have a leader that is like, we should differentiate the word leader and manager, right?

Josh: Yeah. There's a lot of people that are managers, not leaders. Yes, that don't

Jess: lead.

Josh: If you have a real leader, they will value a strong opinion.

Jess: Yes.

Josh: Because, like, they didn't hire you to, like, do their bidding. They hired you because of your brain- Yes ... and your opinions, and you brought a lot of strong opinions.

Jess: I have a lot of thoughts, you guys. I'm not quiet about them.

Josh: You, you are not, which brings me into my third point-

Jess: Yes ...

Josh: which is you have strong opinions, and you did something which I think is really difficult, is you came in as a leader, and you sort of, like, relegated yourself as a leader. Meaning you, you, you, you got your hands dirty, right?

Josh: Yeah. Like, you still, like, build ads and write- Yep ... content and stuff for us. But, like, you made it very clear, like, "Josh, if you want me to be the leader, I need these resources, this budget." And I think you avoided a really sticky trap, which is leaders that are under-resourced often end up becoming individual contributors without knowing it.

Josh: Yeah.

Jess: Yes.

Josh: How did you, like, navigate that really scary world of being like, "Bitch, give me money"?

Jess: Well, I mean, that's my favorite phrase. So that was easy. Money, please. Um, I knew that... I, I think one of my greatest strengths is that I know my weaknesses.

Josh: I don't have any.

Jess: No, I have plenty. Um, and I know where, like, my skill set ends and where I would need someone else's skill set- Yeah

Jess: to begin. Mm-hmm. And I knew that if we were going to Do all of the things, all of the big bets, and then continue to capitalize on them and grow in a way that I saw that happening. Like, we were gonna need some people. We were gonna need some resources. Um, we had to really invest. Like, if we really believed in an idea and we wanted to try it, we had to invest in it.

Jess: Yep. Um, and it could be a test. Like, I think that's something I bring to the table is, like, it doesn't have to be... Like, the first version of this can be small- Yeah ... and simpler than- Mm-hmm ... the actual, like, end state of it. Yeah, yeah. Um, and so I think it was a lot of just like, "Let's try this. Let's test it.

Jess: Here's what that test would look like." Yeah. Um, and so I think that makes it a lot easier to swallow- Mm-hmm ... when it's not like, "We're gonna do a 5,000-person event this year." Right. Even though I know you'd have been like- We should do that ... "Yeah, do it."

Josh: We should do that, 100%. Yeah, let's do

Jess: that. Then I'd be

Josh: like, "Damn it."

Josh: Why stop at 5? Make it 10K. Yeah, right. Yeah. Yeah, what's five

Jess: more? What's five more?

Josh: Who

Jess: cares?

Josh: Come on.

Jess: But yeah, it was like, "Let's try sponsoring a dinner- Yeah ... and just see how it goes." Yeah. And, like, what does a Vector dinner look like, right? Yeah. I think that's part of it is, like, what is your... What is, insert your brand name here, insert marketing program here.

Jess: Like, what does- Yeah ... your version of that look like? Yeah. Is maybe a first step for every marketing leader to start to build the trust and- It's- ... and get buy-in on bold, kind of eventual- Yeah ... states of a program.

Josh: It's a great point, right? It's like, it's so easy to reflect back on the last, like, year, year and a half and be like, "Oh," like, "you've built this big thing."

Josh: But the reality is it was, like, one puzzle piece at a time. Yeah. And I don't think, you tell me if I'm wrong, I, I don't think when you got here on day one, you're like, "I'm gonna end the year with a five-person marketing team- No. ... at a Series A company." You know what I mean? Like, I think you just, day by day, you woke up and said, like, "What's the next bet that we need to make?"

Jess: What's the next bet? What's the next problem we need to solve? What's the next gap we have?

Josh: Yeah.

Jess: Um, I think part of having such a good relationship with you is, like, you help me see around the corners.

Josh: Yeah.

Jess: I think we see around corners for each other.

Josh: Yep.

Jess: And I think that helps us understand, like, what do we need next in the business?

Josh: Yeah,

Jess: yeah. Oh my God, Josh. Yas. It's time.

Josh: It's time.

Jess: To do the thing.

Josh: Uh-huh.

Jess: That people either love or hate. There's no in between.

Josh: Yeah, there's some hate for it.

Jess: There's definitely some hate for it. But we gotta love. We're gonna keep doing it.

Josh: Yeah.

Jess: I don't care.

Josh: We're gonna stare into their eyes and- ... say nice things.

Jess: Yes.

Josh: Positive affirmations.

Jess: Until they believe them.

Josh: Until they b- About themselves ... believe them. Believe in yourself.

Jess: Yes. Let's do it. You're great. Let's do it.

Josh: Dear marketer, your buyer journey has rest stops and scenic overlooks.

Jess: Dear marketer, your competitor could never.

Josh: Okay, so we touched on, like, there's a difference between managers and leaders.

Josh: Mm-hmm. You are a leader, which, which means a part of what we have to, like, pause and give praise to is the team- Oh ... that built who you are. Yeah. Walk me through how, like, hiring the right people, like, elevated you to get where you needed to be.

Jess: Yeah. Um, I think part of building the team that we've built, um, which let me actually walk through who that is really quickly.

Jess: Yeah. So we have, uh ... First hire was Alex Virden, who's our senior product marketing manager. Yeah. I needed somebody who would be able to kind of transform our messaging and our positioning as we continued to evolve as a company.

Josh: Mm-hmm.

Jess: Uh, she also happens to be, like, an incredible content writer.

Josh: She's insane.

Jess: Uh, just unbelievable, like, storyteller, um, best product marketer I've ever worked with in my career.

Josh: Yep.

Jess: Uh, and so we needed somebody who could do that, first and foremost. Mm-hmm. Um, again, that's a weakness of mine, and I knew that, and I needed somebody who wouldn't just come in and, like, end things at the messaging dock, but would, like, own that function.

Jess: Yeah. And I saw her as like, okay, someday when we have a product marketing team, like, she will be the one leading it. 100%. And she will do it so well. Yeah. And so she kinda shaped my thinking around, like, well, that's how I want every hire to be- Mm-hmm ...

Josh: at this stage. Yeah. She set the bar real high.

Jess: Really high.

Jess: Mm-hmm. And I'm so thankful for that because, um, I think we could have just hired doers- Mm-hmm ... who just come in and, like, do the thing and, and clock out. Yeah. And we would've gotten the same, like, deliverables- Yeah ... maybe. Yeah. But we wouldn't have gotten the same, like, outcomes- Yeah ... from them. Yep. And the same, like, care and ownership over them.

Jess: Mm-hmm. And so when we brought in, uh, Kelly Arndt, who runs- Mm ... demand gen, and then Annalisa Rodriguez, who runs content-

Josh: Yep ...

Jess: and now Abby Beckwith, who- Mm ... runs ABM programs- Mm ... for us on the outbound side under marketing. Like, each of those people I see as growing into their leadership role within that particular- Yeah

Jess: function, and that was a lens I used in hiring. Mm-hmm. Part of my growth is, like, I need to remove myself as, like, the content lead and the, you know, person kind of in the weeds doing the stuff to be more of the overseeing strategy and making, making sure everyone's kind of working together, rowing the boat in the same direction.

Jess: Yep. Uh, working from the same narrative, has all the resources they need, right? Like, I need to help them orchestrate and let them go do.

Josh: Yeah.

Jess: Um, and so yeah, that was a big part of, I think, my growth in the past year and feeling confident that, like, yeah, I, I, I can do this marketing leadership thing. Yeah.

Jess: Is like, I can see leadership potential in people who are also just great individual contributors. Yeah. And I think that's so important on our team.

Josh: And I think you were intentional about, like, being patient, finding those people. Yeah. In a previous episode, we talked about it took six months to find Kelly.

Jess: Yeah.

Josh: And, and what that means is, like, there's two ways you can interpret that. Oh, Jess took a... Uh, it took a while to find the person, but it also meant that you were doing that job while waiting for that person. Right? Like, it... Like, you took sacrifice. He's

Jess: doing that job real

Josh: loosely. Doing. There were some questionable deliverables.

Josh: Yeah. Um, but no, like, for the six months you didn't have Kelly. For the year and a half you didn't have Abby, right? Yeah. So on and so forth. You had to kind of hold the pieces in some shape or form- Yes ... what, what was missing from those people. And so, like, that is, like, a very selfless decision to basically say, "I'm going to take my time and be patient, and, like, leave this role unfilled because we need to find the person that is eventually not only so good at the job, but going to, like, lead the function."

Josh: 100%. It was an intentional and hard decision to make.

Jess: Yeah. For sure.

Josh: Okay, I have a question for you.

Jess: Okay.

Josh: W- what do you think about your background made you sort of uniquely positioned for, like, the journey that you've now been on?

Jess: When you first reached out to me... Yeah By the way, listeners.

Josh: Yeah.

Jess: Josh and I did not know each other before this.

Josh: No.

Jess: Nope. Uh, you reached out to me, like, cold DM. Yeah.

Josh: I was not one of your 40,000 followers.

Jess: You were not at the time. And, um, had this really great message about, like, "I'm looking for a marketing leader. I really think I need it to be someone with a content background."

Josh: Yeah.

Jess: And that alone was like, "Oh, my goodness."

Jess: I'm like clutching my pearls. Um, because that is really rare. Most people want someone who's product mar- marketing background or- demand gen background. And I think you understood kind of where marketing was going- Mm-hmm ... and that, like, brand, the importance of brand and how that is going to differentiate pretty much everything- Yeah

Jess: moving forward. Um, and that you needed somebody who could think in that way. Yeah. And so that for me was like, "Oh, my gosh, this is, this is amazing." And then I went to the website, and, uh, the ghosts were there. And I was like- "A mascot?"

Josh: A mascot? Where art thou? Well, Albie. Albie.

Jess: Right? And I thought back to, like, my yeah, whoo.

Jess: Thought back to my, uh, like B2C days. Yeah. And I was like, "Well, this brand has, like, serious, like, B2C thinking"- Yeah ... built into it." Yeah. Like, this feels almost like m- this role feels made for me.

Josh: Yeah.

Jess: And again, like, I could see the opportunity, and, like, this could be really, really big. Just for the way my brain thinks and for the way that I think about marketing- Yeah

Jess: that, like, there was a real diamond in the rough here that, like, with a little bit of love could- Yeah ... really come to life. And seeing all of that made me be like, "Actually, this is, like, a perfect role for someone with a content background, and I really want it to be me."

Josh: And it was. It was. Yeah. I think, um, like, the takeaway for, for folks listening is, is, you know, not everyone has a content background.

Josh: That's fine. That's not what we're saying. Yep. We're not saying, like, you have to have a content background to be a, a, a, the next generation of marketing leaders. But I think what we're saying is to be a marketing leader, you have to be able to understand, like, where the world of marketing is going- Yep

Josh: across a lot of different functions and, and sort of start working on the skills that fill the gap on, like, where your thesis is. For, for me, like, a- and again, every CEO's gonna have a different thesis. Like, you, you might find a, a CEO that says, like, "The world is moving towards, like, AI and automation," and, like, you might have skillsets that are better fit for that CEO's thesis.

Josh: Like, mine was, like, I think the world is going to ironically move to science over art, which is why I wanted art- Yes ... to be, like, the differentiator. Oh, God. Like, I wanted to hire artists over scientists.

Jess: I love

Josh: that. 'Cause I felt like everyone was gonna be scientists. And so, like, that was our thesis, and it just so happened you had spent your entire career, like, being an artist, essentially.

Jess: Yeah. I've, and I, and I felt like my values aligned with those, right? Yeah. I think part of finding the marketing leadership role that just, like, puts you in your zone of genius is like- Yeah ... do I believe the same things this founder believes? Do I have the same kind of hypothesis of where the world is going as the, kind of the company and the founder?

Jess: And do I think my s- do I think that my skillset- Yeah ... could really- Elevate all of that thinking- Yeah ... in this, in this company. And I, like, I checked all three of those boxes here.

Josh: Yeah. I, and I think of, like, different... I, I like to think a lot about, like, it's, there's not right or wrong. It's either, like, right or wrong for me, or right or wrong- Yeah

Josh: now or later, right? And I think of, like, the, all the different, uh, archetypes that marketing leaders come in, and I think of, um, what's her name at Navattic? Natalie?

Jess: Natalie Martulio.

Josh: Natalie. And she's, like, a very different archetype of a marketing- Totally, yeah ... leader than you are, right? And so i- this is not one of those, like, "Oh, I'm not like Jess Cook" kind of, uh, uh, shows.

Josh: It's just, it's one of those, like, find, find your people. Yeah. Right? Like, find what you're uniquely good at. You have something.

Jess: Yeah.

Josh: Right? And, like, find the company that, like, deeply values that version- Yeah ... of you. And if you're not in it, psst, get out. Yeah.

Jess: You wanna something kind of funny?

Josh: Yeah.

Jess: If you would've asked me two years ago if I saw myself as, like, leading a marketing team, I would've been like, "No, never."

Jess: Really? Yeah.

Josh: Wow.

Jess: I thought I was gonna be a content lead for the rest of my career.

Josh: Wow.

Jess: And I was very okay with that. Like, I, that excited me. Um, and I think part of that feeling came from, you know, being in places where, like, content- wasn't as valued as it is here. Mm. Or it was kind of, um, it's such a long tail thing.

Jess: It's like it doesn't really get us pipeline right away, but we kinda have to have it, right? Right. It was just like a, it was m- more of a nice to have and kind of like a, a greens fees, like table stakes type deal.

Josh: Yeah.

Jess: And so I was like, "You know what? I think that's okay." Like, I am, I am good at this, and if this was the position I held in like cool, fun, interesting companies for the rest of my career, I'd be very happy with that.

Josh: Wow. You had like accepted- Yeah ... that like the thing that you enjoyed doing was sort of perceived as a meh. Yeah. And because of that, like you, you, you could, uh, was it, was it almost like a, like a passion thing? Like I could never imagine myself being like passionate about i- this like other side of marketing that doesn't appreciate this art.

Jess: Yes. I think it was like I don't know that I'll really ever find a company. Like, just based on like my, the, the history of like my roles- Yeah ... I didn't know if I'd ever find a company that really felt like a content marketer should be their marketing lead. Yeah. And I was like, "That's just kinda the way of the world.

Jess: I don't know." Like- Wow ... it, and that's okay. Like that, that's just kinda how it is, but I'm good at this, and I'm gonna, I'll just keep doing this. Um, I don't think I realized like it k- it depends on the company, depends on the founder, depends on like-

Josh: Yeah ...

Jess: the brand and the brand potential. And so yeah, I think that was part of something that sparked in me when I saw-

Josh: Wow

Jess: Vector and met you, and I was like, "Oh, no. This is the kind of place I could absolutely be a leader because they value the same things I value." Yeah. They understand brand. They care about content.

Josh: But I have to imagine that means that you didn't spend a majority of your career preparing yourself- Nope

Josh: right, for the day that that would happen, right? So y- you had to have tons of trepidations- Totally ... when it, you know- Oh, yeah ... when you stepped into it.

Jess: For the first 15 years of my career, I thought I would be a, like a creative director somewhere- Wow ... at some agency, right? And so, you know, it wasn't all that long ago that I made the switch, and then I was like, "Okay, I'm gonna do this content thing now forever- Yeah

Jess: and ever." Um, so yeah, I didn't, I, I have very weak muscles in the like demand gen space. Um, I have, again, weak muc- muscles in product marketing. Um, I've never run an ABM program before. Mm. There's a lot of things I haven't done. Mm-hmm. Um, I think there's like a stat out there that's like, I, I believe it's something as high as like 70 or 80% of women do not apply for a job-

Josh: Yep

Jess: if they don't have all of the, the skills and capabilities and qualifications listed in the job description.

Josh: Yep.

Jess: It's a huge number.

Josh: Yeah, and it's sad.

Jess: And men are like 30.

Josh: Yeah, we're like- Like

Jess: 30%.

Josh: We're like, "The pilot's dead. I'll land the airplane."

Jess: That's, that's also a true stat- Yeah ... if you've ever read that, where it's

Josh: like- '

Jess: Cause it,

Josh: like the diving crew goes, right

Josh: it's like 85%

Jess: of men- Yeah, yeah ... think that they could land a plane if the pilot- Yeah ... was incapacitated. Yeah. I told you everything

Josh: you need to know. Meanwhile, like a woman's like pushed out a baby, and they're like, "I don't know if I can hit-" Yeah. "... go live on the marketing campaign." Right. Like, yes you can, girl.

Jess: Yeah.

Josh: Yes you can. Who

Jess: run the world?

Josh: Who?

Jess: Girl. That was the correct answer. That was the correct answer. Um, and so it was a lot of that. It was like, "Well, I don't have demand gen experience," which is very important in a marketing leader. I don't have kind of the product marketing chops. Yeah. I've never run an ABM program.

Jess: Like, I haven't done a lot of the things that, like, most CEOs would want in a, in a marketing leader. Most

Josh: CEOs haven't done their job either. I wasn't a founder before this. Josh fired. Josh fired. We all suck. But it's true. Like, I feel like, to your point, like, women generally- Yeah ... will underestimate their ability to fill a role.

Jess: 100%.

Josh: When the reality is, again, generally, there's, like, loud, obnoxious men that are just like, "I'll be loud- Yeah ... and say I can do it." Like, I'm a first-time founder. Yeah. Right? Like, everything I've done here is new. Like, I haven't led a marketing, and a product, and a support, and a success org, right?

Jess: Yep.

Josh: And, and again, it's, I think it's, like, finding the right place.

Josh: Like, if you can find an environment where, like, people are open to admitting that, like, that's where you'll thrive. Yes. Yeah. Because, like, I knew that you didn't know what the hell pipeline was.

Jess: Hey, I knew pipeline.

Josh: Okay, okay, okay. Not how to measure it.

Jess: Okay, fair.

Josh: No, but like, we just, we kind of, we went on that journey together, and I think one of the conversations we had was just sort of like you came to me and you said, like, "Here's all the things I don't know."

Josh: Yeah. And my response to you was like, "I know."

Jess: Yeah.

Josh: Like, "It's fine."

Jess: We'll get there.

Josh: We'll figure it out.

Jess: Yeah.

Josh: Yeah.

Jess: And I think as we've hired on the team, and I've seen, like, what really good demand gen looks like, and what really good reporting on that looks like, and what really good outbound looks like, what really good product marketing- Mm-hmm

Jess: and positioning, and messaging, and all of that looks like, I'm learning and growing with the team as much as they're learning and growing with me, as much as you're learning and growing as a founder. Like- Yeah ... we're all in this together. W-

Josh: our company is basically High School Musical.

Jess: Yes, it is. Who's Zac Efron?

Josh: Who's Zac Efron?

Jess: Yeah.

Josh: Like, in the show?

Jess: No, like, who in the company is the Zac Efron- Oh, who's Zac Efron? ... of

Josh: our

Jess: company?

Josh: I don't know. Who has, like, a new chin

Jess: implants? Nick has good hair.

Josh: Yeah, Nick has, like, a strong chin.

Jess: He does. Nick, congrats. Yeah. You're Zac Efron. Yeah. Who's Zac

Josh: Efron? Yeah.

Jess: Josh, what- Are you looking for from me next?

Jess: Like, what makes someone good like CMO material?

Josh: Oh, there she goes. There it is. There's the real question within the question. Uh, so that's obviously the next step, right? There's, there's nothing above you except for the, the C-suite title, which, like, we don't have any others at Vector beyond the founder. So it's a, it's a coveted title that we've been, like, very thoughtful because we know how important it is.

Josh: That's what's next for you. Um, so there's a couple things I think of. I'll, I'll, I'll go back to where we started, which is, like, CMOs are essentially mini CEOs. Mm. Right? Like, they, they, they operate marketing, but they operate marketing through the lens of knowing what the company is, needs. Yeah. And that is, like, well beyond the marketing department.

Josh: Um, so I think that will be big. Um, for us in particular, like, we market to marketers. And so, so I have this, like, special thing that I'm looking for for you, which is, like, we need to, like, start to elevate you and I to the CMO persona, right? Yeah. We need to speak to them, and our executive presence need to be there.

Josh: We need to be in the same rooms as them. Yeah. And so-

Jess: We gotta stop doing goofy shit like this.

Josh: Gotta stop doing goofy shit. No, we'll never fucking stop doing goofy shit. Um, no, I think, like, by the way, as like a serious note, like, I think we'll never stop doing goofy shit because, like, I do think CMOs, like, they understand, like, whether or not they're allowed to do goofy shit.

Josh: They, they do-

Jess: Correct ...

Josh: game respect game.

Jess: Yeah.

Josh: They understand what you're doing.

Jess: Absolutely.

Josh: Um, but I do think that there's, like, rooms that, like, neither one of us are ready to be in yet, right? Definitely. If we were to go talk to the CMO of a, you know, a Fortune 500 company, right? There's probably things in, uh, you know, their marketing department, like- Yeah

Josh: we don't know how to talk to them about yet. That's

Jess: final boss level, and I'm not trained-

Josh: Yeah, I know ... up enough. We need to, like- Yeah ... we need to change, like, the little Pac-Man machine to- Yeah ... uh, Mortal Kombat, and we need to start training. Yeah, like, things like that, right? Yeah. Like, and that's something I need to work on, too, is like, neither one of us are ready to go bring Vector to, you know, the top 100 enterprise companies.

Josh: And we need to be able to go toe-to-toe with those folks. Totally. So I think that that's sort of what we'll look at. And then, you know, kind of moving from tactics to strategy and being able to almost backfill yourself. Yeah. Right? Like, continue to build a really great team. Like, it's true what they say, right?

Josh: Like, leaders are the teams that they, they, they build. I know there's a lot of, like, shit on LinkedIn of, like, "I work super hard, and my leader takes credit for it." And it's like, that's kind of their job. That's your job. Right? Yeah. The job of a leader is to hire incredible people that do incredible things.

Josh: Yeah. And so I think continuing to do that and, like, hit your pipeline goals. Yep. Keep, uh, fucking stop spending so much money.

Jess: That's hard. That's hard.

Josh: No, no. Those sorts of things. They, like, all the stuff you're on the path for, right? Yeah. They're super obvious, obvious things. And, um, and obviously, like, I need to grow as a CEO as well to even know, like, how to have a CMO.

Josh: Yeah. You know, how do I work with a CMO? Yeah. But keep them on you.

Jess: It's not easy being green.

Josh: We should, we should end every episode with just, like, I don't know, just random characters. Our worst

Jess: attempts-

Josh: Yeah ... at, like, voices. Yeah.

Jess: You're doing great, Jess. Oh my God.

Josh: Oh my God. Yeah.

Jess: Oh, yeah.

Josh: Do

Jess: that. CMO, CEO material

Josh: right here.

Josh: Yeah, real executive presence we have here.

Jess: Yes. Oh my gosh. So Josh, I'm thinking, like, season four, one of the episodes could be, like, you know- ... Jess gets promoted to CMO. How do you feel about that? Just putting that out there. You are

Josh: just-

Jess: Manifesting ... it just

Josh: went straight to your head. I knew we were gonna have-

Josh: an episode all about all the great things I saw in you, and now you're just a brat. Anyways, this was a great meeting. It was. This meeting-

Jess: It was the best meeting.

Josh: And it could... This meeting could've been a podcast.

Jess: It could have.

Josh: And it was.

Jess: It was. This Meeting Could Have Been a Podcast is a Vector production.

Jess: Vector lets you build ad audiences from real people that visit your site, click your ads, and research your competitors. Imagine seeing exactly who will see your ads by name before you spend a dime. It's a great time to be alive, marketers. Go give it a whirl at vector.co. See you next time.