Payability CMO Deidre Hudson on thinking like an operator, why demand gen is not a silver bullet, setting goals, building B2B communities, and getting inside your customer's heads

This episode is brought to you by Zttle. We're halfway through 2025 and one thing's clear. We've been feeling this firsthand for sure. Events continue to be one of the highest performing marketing channels. Niche meetups, conferences, curated dinners, networking, breakfasts. Everyone's all in. Everyone's leaning into in person. Events have become a core part of our playbook here at Exit 5. So far we've hosted two virtual sessions. We do them twice a month. We do one large virtual event, sometimes two a year. One in person meetup. And we're deep in the trenches right now planning drive our annual conference coming back to Vermont in September. We use Zuttle to help us run a smarter event strategy. They help us with driving registrations, managing invites, automating, communications, reminders, analytics, tracking. They do it all. They have a salesforce integration that also makes it easy and simple to report on pipeline and revenue from events without having to pull an op so you'd know exactly how your events performed. On top of that, the differentiator with ZTTL is how their team is insanely good at supporting us. They always go above and beyond for us and that's how we've been able to keep the momentum going with 12 events this year already and just a small little team here at exit 5. So if events are a part of your marketing strategy like they are ours, you should check out Zuttle to see how Companies like Zillow, CrowdStrike and Iterable are using the top event platform for business events in 2025. Head over to zuttle.com exit5 that's z-u- dash dash-l.com exit5 to learn more.

This episode of the Exit 5 podcast is brought to you by my friends at Metadata. Yes, they're my friends. I'm working with them right now. Hey Metadata, what's up? Metadata helps demand gen marketers automate paid campaigns and drive more revenue. If you work in demand gen, you know how running paid campaigns can create so many technical, mundane and repetitive tasks? You got 17 tabs open in your browser? More like 170. You're jumping from LinkedIn to Google to Facebook. Plus there's all the audience creation, creative and testing variations. It can be an entire job just to keep track of this stuff and make sure it all is running properly. And with humans doing it, there's bound to be a lot of wasted time and potential for mistakes and missed opportunities through AI and automation. Metadata frees you from having to manually do these tasks so you can spend your time on the work that matters most, strategy, creativity and the experimentation. Demand gen teams use Metadata to execute hundreds of campaigns without ever logging into. Ad managers, automatically monitoring their campaigns and optimizing for pipeline and revenue and drastically scaling their performance before needing to hire more people or hire an agency. In the last two years, metadata has automated 92,000 campaigns and influenced over 2 billion in pipeline for customers like Zoom, Ramp, Pendo and ThoughtSpot. ThoughtSpot generated 5 million in pipeline in their first few months at a 1 to 6 spend to pipeline ratio. There's a stat right there. Write that one down. That's a stat that will get you promoted. If you're a demand gen marketer and you're running paid campaigns today, you really should consider using metadata. You can learn more about how the metadata team can help you do humanly impossible marketing. Marketingtadata IO that's metadata IO and make sure you tell them that you heard about them. Right here on the Exit 5 podcast.

Exit.

My guest on this episode is Deidre Hudson. She's CMO of Payability. Deidre, thank you for coming on. For people that might not know you or your background or payability, can you just give us a quick overview of what's the brief rundown of your career, How'd you get to this point and what does payability do?

Awesome. Thanks Dave. I just want to say I'm so glad to be here talking with you. I'm a huge fan. I've been following you since the Drift days. So I'm in the company of a celebrity right now.

I always risk my face is not on camera. It's so embarrassing. I appreciate that it makes me embarrassed. But it is one cool example of like why I care about the brand and marketing stuff is because like I've seen how like in the early days of Drift that connection created this connection. You know, here we are like years later. It is one of the cool things. Okay, cool. I'm going to shut up now.

Absolutely. No, but it's marketers talking about marketing. I could talk about marketing all day. So always glad to have a fellow person that's in that same trenches.

Okay, so take me to first, like what does your company do? And then your role and kind of how you got to that point briefly.

Right. So my company is Payability and we basically we offer funding for e commerce sellers. So you're selling on Amazon, you're selling on Shopify, you're selling on Walmart. You need additional money to pay for your inventory, to pay for marketing. With Amazon, there's about a two Week. Wait. That you have to, you know, wait until you get your payouts based on your sales. So we provide that funding to you so that you, you can get access to your funds into your working capital faster.

And you're the CMO there?

Yes.

What does that mean in the payability context? What's the CMO do?

I'm defining it day by day. We're figuring it out as we go along.

In true startup fashion. Yes.

Right, right. But I mean, I was folding T shirts yesterday and today talking to Dave about payability. So. But basically what the role is and what I love about the role, and that's part of what I love about the role, is that it does change and it's not just a static, everyday thing. But basically what we are in charge of is we're in charge of, you know, top of funnel lead acquisition, drawing qualified leads into the funnel to turn over to our sales team for conversion. And the brand. And the brand is something that, you know, I'm really excited about that we're going to be putting a bit more focus on this year. So, you know, just looking at that in totality, it's presenting the face of payability to the market. What does that initial encounter look like? What does that initial exposure and engagement look like?

What's like the go to market model? Like, how do people find your product and sign up for it and buy it?

We look at kind of a paid and an organic. Right. So we have our paid go to market model where we are using channels like paid media, we're using direct mail, doing events, and then we also have our organic channel where we have a robust newsletter audience and we generate leads from. From there. We generate leads from customer referrals. And then we also have a partnership channel that we're building out, which is, I guess you could think of it as kind of like a hybrid. Right. Because there is some payment involved, but there's also some, you know, word of mouth and referrals involved in that as well. So that's our top of funnel go to market strategy. Marketing's function again is to bring those qualified leads in the door for our sales team to then convert.

So people that listen to this podcast, they just love to nerd out on how other companies are thinking about and doing marketing. So I love getting this perspective. And then you have all those different channels, what are they all driving towards? Is it get a demo? Is it talk to sales? What's the call to action that everybody's being driven toward before the handoff to sales?

The ultimate call to action is for a customer to connect their store to us through an API connection. And we kind of step into that, right? So we step into that through the creation of an account and then hopefully that next step is that, you know, they provided information about their store and they connect their API.

Is it like in the Shopify App Store? Is like, like an app in, like the App Store, somebody goes for free and they download it and connect it to their store?

Well, mainly it's through Amazon. So they can connect their store through an API connection through Amazon and then we can, you know, we, we can basically look at their sales history and look at their sales and that's because we don't do credit checks. We really look at the health of their e commerce business in order to determine, you know, how we can help them from a funding perspective.

Got it. Okay. So people come in and they connect their account and then that's the point that someone is going to reach out from the sales team.

Right? Someone will reach out. So if someone has started an account but hasn't connected their API, they'll get a reach out from our BDR team. Once that API is connected, then we turn them over to our sales team and then they complete the sales process. We have about three different products that we offer, three different funding options. And what our sales team is here to do really is to help guide people towards the right funding option for them.

How do you think that approach changes how you do marketing and help feed the sales team?

That's a great question. I think that changes because it's not a one step conversion. You do need to go through a couple different steps in order to become a customer. When we are looking at our marketing activities and we're looking at diagnosing the funnel and looking at optimizing that customer journey, we're doing it with an eye to how do we optimize each step to get the person to the next step and what do they need to get to that next step? So that really affects our approach because we're not thinking about, okay, once they sign complete an app, that's it, we need them to do a few more steps.

No, it's interesting to hear you say that because one company that I'm working with, I feel like sometimes the marketing and I've done this myself, like I've been in this, I've, I've messed this up. But I feel like sometimes you just kind of like it's easy just to like do marketing and you're just like, we're Doing all these things, but, like, you have to actually map out, like, because there's an infinite amount of possibilities. Someone could go from not knowing you to talking to your sales team. But I feel like you have to have what you have mapped out. It's like, hold on first, what is the customer journey? What are the steps we want them to take? And then what are, what actions are we going to do? Like, I don't think you can, like, make marketing a checklist and a perfect formula, but I feel like, like you have to build a marketing strategy around some, like, hypothesis of, like, this is the funnel that we're trying to drive. Then you can go decide what channels to put on top of that.

I love so much that you said that, because checkbox marketing is something that I have a visceral reaction against, and I'm really about the holistic planning of it. Right. So we're not just sending an email because we want to send an email. What part does that email play in the entire strategy? What do we want people to do? And how are we recognizing the difference in how an email is perceived as a different tool than, say, a paid media ad? You know, an email is very transactional. Someone expects to get something right away. For those three to five seconds, they interact with your email versus on social media. They want you to teach them something. They want to come away having learned something new. So understanding those channels, understanding how those, how customers are perceiving those channels and how they all fit into your holistic strategy, I think is super important.

I'm the person who made this stuff happen, but now I have a little bit of years and so I can see what the mistakes that I made. But the amount of times it's so easy for the marketing team to just get in this rhythm of just like, we're just doing stuff. Like we send out an email every Tuesday and Thursday because we just kind of always send out an email Tuesday and Thursday. And then one thing that I see at a bunch of different companies is like, it's not that nobody's ever busy. The marketing team is always busy. But the problem is sometimes everyone's really busy and you're not making progress towards your goals. And that's the most dangerous combination because you're just kind of doing stuff like, I don't know, we always write blog articles. So that we wrote five articles this week. Well, but for what? Why? Right.

Exactly. Thank you. At my previous role, my mantra became, what's the goal? Right. I would always ask, what's the goal? Why are we doing this? What's the goal? What's the. The goal? What's the goal? And I started to love. And I heard people repeat that back to me and they'd ask me, what's the goal? And I'm like, yes, it worked.

Can I tell you a quick story about that, by the way? Like, that's, that's one of those things that, like, as non marketing leader Dave hated when my boss asked me that, what's the goal? I don't know. You tell like, I know what the goal is. Don't you worry. But it's like now that as a marketing leader, like, that's like, it becomes the only thing you're going to ask, what's the goal? What's the goal? What's the goal? But you understand why. Because if you don't have that thing, everything is off.

Exactly. And we're going to take it even one step further because now we're going to ask, why does the customer care? Right? And we're going to go through those seven, nine whys. Why do they care? Well, because they want this. Why do they want this? Well, because they want that. Why do they want that? So it really is about just distilling things down to the essence of what are we trying to achieve and is this the right tactic? Is this the right strategy? And you're going to have to answer those questions. You have to answer them before you start your marketing campaign or after you finish it and you don't get the results you want. So you're going to have to answer those questions. It's better to answer them on the front end than the back end. Right. Measure twice and cut once.

This is great. I already. I'm going to clip out all this. But you mentioned something that seems so obvious. But I don't think we ask it enough with every channel, with everything, which is you said, why? Why does the customer care? And so it's this simple discipline of like reinforcing, like, what's the goal of this? And oftentimes, even when you ask, what's the goal? That just leads you to your next, like, oh, wow, we don't have a goal. So maybe we need to pause before we go do this and have a discussion about this. But you mentioned why does the customer care? And I think that's the one that, like, in both levels, the macro. What are we doing this quarter? And why? Why is somebody going to care about that? I just think we. It's easy to get in that, like, just set it and forget it. Mode you mentioned a BDR team. Does BDR team report to you or is there a salesperson? That BDR report team, how does it work within your company?

Our BDRs have been shuffled around like orphans. I'm sad to admit, but they are now currently. They're currently in their needed and respected home with sales.

Was that not always the case? Is it better, better now? Did you make the change for a reason?

First arrived at payability? Well, before I arrived, the BDRs were reporting. I believe they were reporting into our head of partnerships who reported to our then cmo. And then when our CMO left and we kind of split it and the partnership started reporting into the CEO with the BDRs reporting to the partnerships. But then the partnerships left and I inherited the BDRs. And you know, it's great. And I look at it this way, right? You can look at BDRs as either the last mile of marketing or the first mile of sales, right? So in that case, we chose to look at it as the last mile of marketing. But I do believe that BDRs, they thrive better being managed in a sales type environment. They're going to be much more driven by goals and motivations that align more with the sales methodology than with the marketing methodology.

Love that line. The last mile in marketing or the first mile in sales. I love that because it's like maybe it could be managed by different teams which you zoom out and you don't take the team. You just think of like what's the business function? Well, it's either the last mile of marketing or it's the first marketing of sales who should or the first mile of sales who should own that. And by the way, your answer there, I wanted to pause on that for a second because obviously we put a lot of things out in the world on LinkedIn and talk about marketing and give marketing advice. But your example is so real of what life is actually like as a marketing leader on LinkedIn. It's like BDR, should they report to this and then what actually happens is other CMO is there. You come in new cmo, they report to this team. It's not really perfect. They go to this team. It's never this perfect thing. So all business advice should be taken with a grain of salt because the reality is you often come in with so much debt that you're just kind of stuck with exactly what metrics do you report on what's on your scorecard?

That's interesting because we do typical marketing related metrics. That's around Costs. So it's cost per CPAs for our sales qualified leads. It's CPAs for one deals. It's CPAs for different milestones within that journey. But what I'm really trying to shift us towards this year is focusing more on revenue. Right now we are a marketing driven organization in terms of where our leads are coming from. So we do need to be very paid, very close attention to costs. But we also need to understand what is the revenue component behind that. Right. So I can pay $3,000 to acquire a lead, but if that lead is only worth, you know, $2,000 and was it worth it? Right. If we don't have that revenue component in our metrics, then it's hard to make those kinds of decisions. So we're trying to get our data to the point where we can incorporate the cost side of our marketing activities with the revenue generating side. So that's what I'm really hoping to focus us on in the coming year.

How do you go and tackle that? Is it like a data thing that you're trying to uncover behind the scenes?

I think for us it is a data thing behind the scenes and it's kind of an integration thing because we can, we can go to finance and compile the reports and go to underwriting and compile reports and then put it together. But that data becomes obsolete almost as soon as you're done compiling it. For us, it's trying to get all that data into one place that we can really do meaningful self serve data and analytics that incorporates not just cost but revenue.

Where this focus on revenue come from your end?

I'm going to plug something else here. I read this awesome book called the Next cmo.

It's a great book, right?

Oh yeah, I'm sure it's in your library. I remember reading it like I don't know, a year or two ago and I was just blown away because you know how there's, there's things in your head that you think, okay, something's not right with this or I think I should be doing this differently, but I'm not quite sure how. And that book just kind of put it all together for me and I had this copy of it. It's like it's dog eared and it's got colored tabs on it. And after I was promoted to CMO, I posted a picture of the book on LinkedIn and they said, I guess it worked.

That's amazing. That is an amazing book. And I love that book because of why you mentioned it. It's like, no fluff in that book. It's literally like playbooks. Like, hey, you want, here's how to run campaigns, here's how to measure this thing. So you literally took this book and just said, I'm going to apply these things to what we're doing in marketing.

I did. I took that book and I used it in a couple of ways. Number one, I agree with you in the title and the subtitle of An Operational Operational Excellency. Something about that. But it wasn't about the next CMO because you able to build a great brand or the next CMO because you are a great demand gen person. It was like the next CMO has operational chops. So I really liked it for that reason. So yeah, and I took it in a couple of ways. I literally inhaled it, if you can imagine that. It's like I just wanted to sniff all the things and just absorb it into my brain so it would just become like this other layer inside my head. So I literally sniffed it and inhaled it. So that's one way I used it.

Amazing.

The other way I used it was as a playbook and you know, especially in my previous film as we were making some changes, and I literally use it as a playbook and say, this is how we need to approach this from this particular standpoint.

And by the way, how about like the meta of this, what Deidre's talking about is a, is a marketing asset created by Plana. Like this is marketing done right. Like, how do you create raving fans about your stuff? It's like, well, Peter and the team they created, they didn't just make an ebook or a PDF. They wrote an unbelievable 150 page like marketing playbook and give that out out to potential customers. And now to have somebody like yourself, a CMO on this podcast raving about the book, that's like the ultimate meta lesson. So shout out to Peter.

Yeah, great.

How do you articulate the shift from like, you're not just a marketer, you're an operator who's running marketing. Like, what's changed in your thinking?

Well, for one thing, it kind of solidified some things that I had thought because previously I had focused on, I was in the demand gen world and I had formulated this methodology as I went throughout different roles. That demand gen was not a silver bullet, but it was actually a structure that you built and it's a foundation that you build. And I envision those, that foundation being based on four pillars and those pillars were people, performance, process and programs. So I'd Always kind of refer to process as the unsung hero of good demand gen. And because I saw it time and time again where you could be in a company, for example, I give this example of a company that's like very mature in programs, but very immature in process.

And an example Today's episode is brought to you by ahrefs. You probably know Ahrefs as an SEO tool, right? I've been using Ahrefs personally for over a decade to see how we rank and see what's driving traffic to our site. Content marketing has always been a big part of the playbook. I use their product at Drift at Privy and now we're using it at exit 5. But over that time, Ahrefs has evolved.

A lot and they're not actually just.

An SEO tool anymore. They're a full on marketing platform built for marketers like you and me who want to grow traffic, understand our audiences and make smarter business decisions in the AI search world. Their marketing intelligence lets you see what's driving traffic to your site, to your competitors, understand top performing content, paid keywords, backlinks, and you can even understand how much or your organic traffic would be worth. Put a actual dollar amount to all that organic traffic that you're driving. They've also got tools for AI powered content and keyword research. 24. 7 Site monitoring, real time analytics, backlink tracking, brand mentions, you name it, you can do it all in one place. With Ahrefs. It's really a marketer's dream. If you're a marketing nerd like myself, one of the coolest features in my opinion is their new brand radar tool which allows you to explore what people and AI says about your brand, topic or niche. You can do this to do amazing research to help understand what's actually happening in AI search today and just what the conversations are online about your brand. Plus you can try their free analytics tool to show you how many visitors you're getting from AI search like ChatGPT or Perplexity. And look, as a firsthand user of this, so much easier to use than.

Something like Google Analytics.

I love it. We use it on our site. I've used it for exit 5 and we just found out that over the past 30 days we've got 105 visitors to exit 5 from AI search, 95% of that was from ChatGPT, 5% of that was from Perplexity. But it's really cool to understand and this is the way that search is, is going and shifting. So ahrefs not just an SEO tool anymore. It's a legit marketing platform for anyone serious about growth in today's AI driven search world. If you do any type of content marketing at all, you gotta go check them out. Go visit ahrefs.com that's a h r e f s.com today. Go check them out.

All of that is a use case is that you're cranking out a lot of stuff. You got a lot of stuff going on, but you go to the event and you come back and the leads sit in salesforce for two weeks. But you don't have a process of getting them from point A to point B. So I became very enamored with, you know, this idea of process. And plus I just love the underdog anyway, so that's just my, my pet thing.

Also for people listening, like to hear you say like as, not even as the cmo, as the demand gen leader, you were thinking about your function with those 4P things, right? And it's like that's how you start to think like an executive. You're not just like Demand gen equals AdWords channel. It's like, well no CEO, there's four layers of demand gen. There's. What did you say? People, process, programs and performance. So you're not just trying to have a discussion about the conversion rate of your ads. You're like, well, the reason that we're not hitting these goals, revenue goals, is because we don't have the right people or we don't have the right process. So it makes no sense that you're eventually going to become CMO from that. I also think like to be a great CMO today or even a good CMO today, you have to be the person that you're, you're talking about. This is why I am not a CMO for the record, because I'm really good at like the creative stuff though. Come up with marketing ideas stuff. But like to be a professional CMO like Deidre is like, you have to think about marketing with those four layers. It's not just the creative, it is the people, it is the process, it is the goal setting, it is the planning. Like that's what the role of CMO is. And so like it's not the, like you just come up with the craziest. You know, your job is not. You walk into work, come up with a fire marketing idea and your day is over and you go home. It's like, no, it's people, it's process, it's budgets, it's managing up. It's much More of this operator job, right?

Absolutely. It's definitely all those things. And don't get me wrong, I definitely get turned on by the, you know, the crazy sexy idea, but I get more turned on by the idea of how do we look at this holistically? Like, okay, this is, is the great creative idea, but what was the data that brought us to the fact that we needed that idea and how are we going to make this, you know, what's the process we're going to use to implement this idea and how are we going to measure the performance of this idea? So that totality and holistic part turns me on even more.

I don't know about not myself, but, you know, to each their own. We're all different in this world. I have a feeling that you might have a kind of methodical approach to planning and like, running campaigns just based on what I know about you. Can you give me your framework for like, how do you, how do you do marketing planning? What's kind of like the cadence for, for you, for your, you and your team running marketing month to month, quarter to quarter?

Yeah, ideally it is, we start with, you know, what is it that we're trying to achieve this year? And here we're not there yet. We need to bring on more people, we need to bring on more ways of measuring performance. So we're not there yet. But ideally we're starting from the goal, like, what are we trying to achieve and why are we trying to achieve that? And then we're looking at data. Okay, what does the data show us already? And then I just, I just get ideas from data and I try to encourage people to use data as a stepping stone for a launching pad for ideas also. And then that leads into, you know, we do, we have our weekly marketing meetings and we're talking about operational things from like a project perspective. And then we start spitballing and brainstorming and then, you know, we kind of bring it all back to, you know, concrete next step. And then, you know, part of that also is that we're talking about, okay, how are we going to measure this and what do we need from our, you know, our data in order to be able to do this? So ideally, that is the framework. Like I said, we're not quite there yet. We're working towards that.

But I, are you running like, you know, each month we're doing some launch. Like, you know, right now you're in the middle of X time frame. Like, how do you figure out what's going on when.

Well, we have Some, just some long standing things that we're running. So we know that we're running paid media, right? So that's kind of one of our staples. We know that we're running, running direct mail. That's one of our staples. We look into those staples for how can we make them better, how can we optimize them, how can we make them perform even better? And then we look for what other things can we add on. But it's not just to add on other things just for the sake of adding on new outlets. It's how else can we get there? So basically what we're trying to do this year, what my mantra, one of my mantras for this year is I want to be everywhere our sellers are. So we're looking at things called micro ecosystems. And these micro ecosystems are basically, you know, what does our seller's journey look like? And what are these different ecosystems that they're going to encounter along their journey? And we need to be in every one of those ecosystems. We may have a different place and a different presence, but we need to be in every one of those ecosystems. So taking a step back and looking at it from that perspective, it's like, okay, then how do we get into those ecosystems? What do we need to do to get there? What kind of presence should we have?

What do you mean by ecosystems? Like communities, podcasts, it's all that.

So if you think about someone that is selling on Amazon and just think about that journey, right? So one day one person decided, I'm think I'm going to sell on Amazon. Okay, what do I do to do that? There's research, there's, you know, gathering information. That's an ecosystem, right? And then it's like, yeah, and then.

You make, I've seen someone like, there's just someone on Instagram who has like, like a hundred thousand followers talking about how to become an Amazon seller or something that would be an influencer that you might try to do content with or something in your space, right?

And depending upon what they're talking about, they're part of one of those ecosystems.

Yeah, no, ecosystems is a cool way to think about it. You mentioned direct mail. I haven't been in the direct mail game. I've been out of the direct mail game for a while now. What is going on in direct mail in 2022? How does it work? And, and how do you reach people? Like, how do you get someone's house if everybody's working from home? How do you actually reach them?

First of all, direct mail as A channel. I think that everything is cyclical, right? So we were so digital, digital, digital, and everyone predicted the death of direct mail. But for every trend, there is a counter trend. And for every 10,000 people that want digital, there's going to be 100 people that want something that they can feel and touch. And those numbers start to change and that's how trends develop. So direct mail.

You're so right. You're so right, by the way. Like, yeah, events, event like events this year and next year are going to be on fire. You're so right. The cyclical nature. Most people try to say direct mail never died, but I think with the way you laid it out is so true. It's very cyclical because we over rotate on one channel, that channel gets super noisy and then we go do something else.

Right, exactly. So as a channel, those are my thoughts on direct mail. And how do we reach people? We're getting their address. The challenging part for us is identifying sellers. So once we identify sellers, we can get addresses, but it's identifying who's selling on Amazon, who's selling on, because there's.

No just list of people somewhere. It could be me deciding to wake up and sell on Amazon one day.

Right. And the difference between you selling on Amazon and you selling on Shopify is at Shopify, you'd have your own, your store URL. And I could find that and I could find information about you with that. But Amazon sellers don't have that. So Amazon sellers are a little bit more trickier to find.

Right. What are you using for direct mail, if you can? If you don't mind telling people we're.

Doing it in house. Our director of marketing, she's been with the company since its inception. She was the first hire from our CEO. And I mean, she's. I can't sing her praises enough. She's just a whiz with things and she handles our direct material.

I want to talk about team and hiring stuff. You mentioned that you're growing the team hiring.

Yes, knock wood. That is the plan.

What's the state of the team or size of the team today? And like what do you. What are you trying to hire for?

So currently we have kind of a mixture of different roles and types. So we have basically addition to myself, we have four FTEs and we have two people who are working with us on kind of a contractor basis. But they're kind of like employees because they're just in the midst and in the fold of everything. And then we work with two external agencies for pr. And we have an agency we just brought on that's doing our SEO and HubSpot work. Now, the way we're currently organized is, first of all, we're a small company, so everyone wears more than one hat. Right. So we're organized pretty functionally with a little crossover. So we have a senior graphic designer, and he does all of our visual language work. And my director of marketer, the director of marketing that I mentioned, she does our direct mail and our data and analytics, and she has a direct report who is our kind of marketing analyst. And then we have a head of partnership. So we're looking to bring on, over the next year, five additional headcounts, and that's going to be someone that we can work with for events. We need to bring on a product marketing person. I want to bring on another director level of kind of inbound marketing, and then bring on an SEO person and potentially a content person. So I want to get us a little bit more organized around functions so that there's a person that's looking at. At, okay, what inbound channels should we be doing? How can we optimize? How can we, you know, experiment there? And someone that's looking at data, and it's just. They're all about the data. So I want to organize a bit more functionally.

And you're also at this, like, challenging stage, which is like, with four people, you can't just do fourth. Like, everybody's job is kind of like a job and a half, you know, like, you kind of have the product marketing person who's also doing partner marketing, or the content person who also own social and community and whatever. For now, you kind of have to lump those things together, right?

Absolutely. We all wear more than one hat.

Okay, well, hopefully you're hiring and maybe you'll find a dream marketer out there from a place like DGMG Jobs or something like that. I don't know.

Yeah, DM me.

Yeah. Come on, please. There's lots of good marketers that listen to this podcast. So if you want to work with Deidre, and what better, like, way to start to hear what your future is. Your boss must be like, did I listen to your podcast before your interview? You got a team of four people. You got agencies. What does a manager, Deidre look like? Like, what time do you spend or how do you do one on ones with the team? And whatever kind of team rhythms do you have?

It's. I think it's pretty consistent. And then, you know, we're still kind of working out some things. So we have a weekly meeting with the entire team, and that meeting is to accomplish a few different things. We look at, at our okrs, we look at our budget and where we're pacing. We look at the status of existing projects, we look at new projects, and then we end up doing brainstorming. So that's kind of an hour, an hour and a half every week. I also have one on ones with my direct reports. So I have a weekly one on one with my director of marketing, with my partnerships manager, my senior graphic designer, and I'm starting to have one on ones with our copywriter as well. And then we have more like project meetings. Depending upon who's involved in the projects, there'll be project meetings. I'm really trying to, you know, from a productivity standpoint, I'm trying to eliminate Friday meetings because, you know, to your point earlier of where you get into the habit of you just kind of doing, doing, doing stuff and you feel like you're not making progress. You know, I realized that as a leader, I need time to think. And I owe that. It's not just for myself because, because I'm a nerd, I'm an introvert. Put me in front of a book or just tell me to go research something, and I'm like a pig in heaven just researching and reading all day. So it's not just for that part because I enjoy it. It's because I owe my team to have a vision and to have a strategy and to be able to communicate that vision and strategy. And I can't do that if I'm just kind of running around from project to project all day. So. So that's how I'm trying to structure it. Again, not there yet, but I cut off two meetings from my calendar this Friday, so I'm making progress.

Yeah, that's so important. If you don't put that time on your calendar, then you're just like constantly reacting.

Right.

You need time to be like, okay, I do need to be there for the team and I do need to be involved in things. But the team is not thinking about what you're going to be doing in July, but you need to be thinking about that. And so, like, when are you going to make time to do that?

Exactly, exactly.

Yeah. I think that's just a great, great philosophy to like, it can be easy to just be in the weeds and just think like, the doing, the doing, the doing. But like, ultimately you, you have to remember you own. You own the marketing. You own the, like, the marketing Your own is a marketing strategy. And so you need to be able to articulate the whole approach. Like, what are we doing and why? This goes back to like, you mentioning, like, being the operator cmo.

Right, right. Exactly. Exactly.

What would marketing manager demand? Gen manager, Deidre. How is she different from cmo Deidre? And like, what would you. What kind of career changes have you made to move from marketing manager to cmo? And how do you articulate the difference?

Good question. I think that it's exactly what you said. You know, as a, as a marketing manager, I can be. I can be focused on a channel and I can be focused on, you know, like say, paid media, but I'm not necessarily focused on why are we doing paid media, how does paid media fit within the other things we're doing? And also, I'm not really focused as a marketing manager on any kind of budget allocation decisions that I need to make. Right. But as a cmo, I need to figure out the money that we're spending in paid media. For instance, is that the best use of those funds? Can I put those funds someplace else? Do I need to put more funds there? So it's really having that 10,000 foot.

Holistic view, or should I take those funds and use them for the other team? Maybe the other part of. Maybe this other team in marketing needs that. Not. Not this team. Right. You see it at that level.

Exactly.

You have a pen? Anything on your list, on your note list that you want to talk about before I keep us going? Coin, Anything you want to go back to?

I do want to talk about building a community at some point though.

Let's talk about it. Go ahead. This is a good place to do it.

I think this is an important step for B2B marketers in general. Right. We have gotten so far past the, you know, we're not doing 30 page white papers anymore and, you know, Drift did those amazing colorful books. I actually used one as inspiration for some content at my previous role. So we know we've moved away from that, but we also need to move away from this idea of asking someone to tell me about your job is a good B2B lead acquisition method. I can't tell you how when I get an email, a cold email from someone and it says, oh, I'd love to put 30 minutes on the calendar to learn about your job or to, to learn about your pain points. And I'm like, what? Wtf, right?

Like, yeah, come on.

Oh, good. Thank you. I've been dying to curse.

Please. Oh, let it fly now. We have 20 minutes. You better let it fly.

Actual, like, thank you. So you want me to take 30 minutes out of my day to basically do your job for you?

Yeah. Hell, it's crazy. Or my favorite is like, hey, Dave, when do you have 30 minutes to tell me about your priorities?

Thank you. I don't.

How about never? I don't.

Thank you. The fourth of never is when I have time for that conversation.

But, like, this is what the templated email is at many companies, right? And so, like, if you don't try to make that better, then, like, this is where also, like, having an understanding of, like, what does the outreach look like, right?

And that's where I comes in. It's like, you've got to build a community.

Okay, so what does that mean? Like, we know that that type of shit doesn't work. You can't just, you know, spray and pray terrible emails. But there is a lot of buzz about community. What does that mean? How do you define it?

Yes. And before that becomes the next buzzword, I think it is important to define it. Right? So the way that I'm looking at it, and we're starting to map this out, the way that I'm looking at it is that. And this is just. This is marketing 101, right? Because by the time someone has come to you, you know, now you're going to be negotiating about price, right? Whereas if you are able to establish that relationship with them before they even think about needing you, when they do need you, you're going to be the first company that they think of because you built that trust, you've established that connection, you've created that relationship. So now how do you do that in this digital world in a way that is authentic and that makes sense. So I think that's probably the challenge, right? Because everyone's creating content. You got AI tools out there now that's creating content. So it's not just about that. It's how do you form that connection. And I think that's what's really important. And that's really about knowing your audience and knowing what they want without asking them to spend 30 minutes telling you about their pain points.

Yeah, well, like, I mean, you. The way you articulated is so spot on because I think the myth that a lot of people think is like, oh, we'll have a. We'll have a Slack group. And because it's hosted by the company, it's a community. And then what that Slack group just deteriorates to is once a week, the community manager at the Company posts, hey, we have this event, it just becomes another channel. Just post company crap content. It's the same stuff that would post on LinkedIn. What really works with Community is if you pretend that you don't even work for this company. Deirdre and I, we're all working on our own business. And our business, we want to make a community for B2B marketing people. If we just built that and we were not affiliated with a software company, it'd be way more successful than if we were. Because internally, the tug of how we going to measure that? How are we going to turn it into sales? But if we did it completely separately and didn't make it about a single product or company, that's the only way that this is actually going to work.

Exactly. But you know what? That can be a tough sell internally to your CEO, to your cfo. That can be a tough sell because, you know, the first question is usually, okay, well, what's the ROI on that?

Right. And how are we going to mention Drift? Right, you mentioned the Drift stuff. One of the reasons we were able to do that, because it was the CEO was doing it, you know, like, he wanted to do that and was like, great. There. There's no justification for it. We did. Seeking wisdom. We did. You know, we had these different ideas. Like, it has to come from that. Yeah, you're not. When you're not fighting that battle, it's like, okay, we're going to get a hundred signups to our community. And then like the vps sales is like, well, when can my team call those leads? Like, whoa, whoa, whoa. Like, that's how it can't.

Right? That's not what this is for.

Do you believe in this? Are you. Are you building a community? Is that a part of your strategy?

I want to. Yeah, we just started mapping it out. So, yeah, I want to. You know, we have. Listen, we've got a lot of goals, a lot of things that I want to accomplish this year. We definitely have to kind of prioritize. But overall, you know, like I said, my goal is to be everywhere our sellers are and to just build those connections and relationships with our target audience.

I think, like, even beyond community, I think what you talked about is, like, in how people buy. To me, the goal is you can call community whatever. The goal is to become known for that thing that's meaningful. So, like, you know, if. If, like at Drift, we were trying to do conversational marketing, our whole marketing was about teaching you about this new way of doing marketing. So I think the More companies have like a unique point of view or their way of doing things as it relates to something broader like sales, marketing, finance, entrepreneurship, whatever. That's your best chance to like actually build, build something off that. The more you make it like just about your product and making an extension of that, it doesn't. It doesn't work.

Exactly. It doesn't work. And I, you know, that was one of the things that I really kind of became attracted to at Drift is I was at a conference in Boston one year and I guess this was you actually, because you had your marketing people out there and they were like staging a demonstration with picket signs and it said, treat people like people, not leads. And I was like, oh my God, you are fucking absolutely right. Do you remember that?

Oh my God, this is amazing. I was just talking about this with somebody the other day because, yes, I. We know. I know exactly what event this was. I know exactly what hotel it was at. And the event person that went down there, she, I think she had called us and she was like, I just, I just got arrested. Or like it became, we became some joke. Yeah, yeah, that's. That's so amazing. Yeah, something, something like that. Treat people like people now leads. But I think we gave something for people to rally around. HubSpot and what they did with inbound marketing, I think is like the, you know, the all time example of this, which is like their whole stuff was all about like, I'm going to teach Dave how to be a better marketer. By the way, we happen to make software that you can use to do all these things. But like, I'm going to be smarter because of your stuff. And I think that to me is the approach. And then you nailed it earlier. Like, then our first conversation is not about price. It's like, I'm coming to you. Look, I'm still shopping, I'm still looking at two or three other vendors. However, I'm coming to you first because I feel like I know your business or I've been on your email list, I love your podcast, or I've been on your newsletter or I went to your event or whatever. I'm going to let you throw your hat in the ring as to be part of that conversation.

Exactly, exactly.

Are you seeing anything interesting with people? Like to hear about tools and tech and don't feel pressured to answer this. You don't have to. It could be nothing. But if there's any kind of tool or tech that you're really interested in.

We actually are getting up and running with HubSpot so I'm excited to get that tool in place because we just really need one place to be able to see, have more visibility into the full customer journey. We've got bits and pieces of it in different places. So I would say HubSpot is the one thing I'm excited about right now.

Whether it was HubSpot or not. But what's the blank, snap your fingers problem that you want solved with switching this out? Is it attribution stuff?

Yeah, it's customer journey and attribution.

Yeah, absolutely. Usually always the case is like there's something that's not lining up correctly. Let's put it all in one platform and make this easy.

Right. Because you know, we get to another hour about attribution.

No, not you and me, we can't. Yeah, right. No, you said, you said you still like the creative ideas. We'll do an hour on those. I'd have to trade you an hour of that for an hour of the. Whatever that was we have to talk about. Yeah, well, actually, no, we'd have to do two hours of creative talk. Okay. If you, if you had one wish and could solve any one marketing problem, what would it be? For example, like, I wish I could get emails for every podcast subscriber. I wish we could get attribution on everything, blah, blah, blah. What would it be for you?

I wish I could get first party data on every Amazon and Shopify seller in the United States.

Nice. That's a good one. That would surely make your life. But I love asking people that question for that reason. That's a perfect example of it's not necessarily the most creative marketing strategy that's going to win. You need data, you need something to operate on.

Absolutely.

How do you tell your family what you do, what your job is?

It's funny because when I first started, I was working in the membership department of a human rights organization. We were doing lots of direct mail. So I told my family, oh, we're doing direct mail. So my smart ass little sister says, oh, so you work in the mail room?

Yes.

I was like, no, smart ass, I'm not telling you anything else.

No, I send mail.

But it's funny because my, you know, in this day and age, I mean, my kids, actually my kids understand what I do. My younger son, as a matter of fact, I have two sons. One is 17 and my youngest is 11. About two years ago, my 11 year old and he was, you know, nine, he decides that he wants to do a YouTube channel and he says, hey mom, you're Marketing. Right? I was like, yeah. He said, can you help me get more subscribers?

Smash that, like, button. That's amazing. Hey, mom, can you help me grow my YouTube channel? That's actually kind of cool. Hey, mom, can you help me read this white paper? That's awesome. My kids are five and three, and so they. I say I got to go to work, and then I just sit in front of a computer and look, and they think. They're like, what does he mean? What does he mean, going to work? You just. You're just looking at the computer, dad. Well, I don't understand that. Okay, that's great. But you didn't tell me. What do you tell people that you do and you run into a friend, somebody you haven't seen in a while? How do you tell them that you are. You're a B2B SaaS marketing CMO and regular people work.

I don't. I just say I lead a marketing team.

I love that. Me too. I. I don't. I hate having that conversation.

Yeah. Yeah.

I work in marketing. Great.

Yeah.

Okay, last question before we go. Now that you've been on this podcast, other than I want to keep talking to you for longer, tell me one other CMO or marketing leader that I should have on.

Drew Nesser. I think I mispronounced his last name. Renegade Marketing Marketing.

Oh, yeah, I know him.

Yes. Yeah, I'm in his CMO Huddles group, and I love it. So awesome.

What is CMO huddles?

I call it a CMO support group.

Therapy.

Right. Therapy for CMOs. But, I mean, it's a great group. I mean, it's sharing information. I think his motto is sharing, caring and daring. So really is, like, sharing information. He's got these Huddles, you know, take place weekly, and you just go on and you get kind of a deep dive into different topics. And he has a Slack channel.

Nice. Yeah, but that's. I mean, that. That type of stuff is so valuable, though, as a. To just get benchmarks and, like, hey. Oh, yeah. These companies are also having trouble. Hiring is an issue at this other company.

Yeah. Yeah. That's why I call it a support group, because you. You feel like you're not alone.

This has been awesome. Awesome. Thank you for coming on the podcast. Before we wrap, where can people find you if they want to just send you a message and be like, I loved you on Dave's podcast.

Awesome. I am on LinkedIn. It's just Deidre Hudson. It's D E I D R E Hudson. Like, the river in New York. That's the best place to find me.

We'll link to you and everything so people can also connect and say hello. Thanks for joining me. This was a lot of fun and hopefully I'll see you around soon.

Thank you. Bye.

Hey, thanks for listening to this episode of the Exit 5 podcast. If you're in B2B marketing and you want to grow your career, you should also go and check out everything that we have over@exit5.com we've got articles, we've got videos, we've got templates. Plus we have a community. A community of over 4000 B2B marketing pros. Whether you're deep in your career and want to connect with your peers or just starting up and you, you want a place to go where you can see what people are talking about. Get smarter about B2B marketing in your own time to grow your career and help grow your company. Go and check it out. It's exit5.com you can get on the email list there you can join the community. There's 4,000 marketers in the community. We have a job board. We're always adding new stuff. It's really becoming the number one place you can go if you want to grow your career and learn more about B2B marketing outside of what you're doing inside of your company. Company every day. So check it out. Exit5.com and I also want to make sure I give a shout out to my friends at Hatch. That's Hatch fm. They produce this podcast. It sounds amazing because of the work that they do and they work with B2B companies just like yours. They offer unlimited podcast editing and strategy for businesses. You can get unlimited podcast setting and on demand strategy for a low monthly cost. All you got to do is just upload your episode and they take care of the the rest. Go and check them out. It's Hatch fm.

Today's episode is also brought to you by Paramark. It's July 2nd half of the year is here and hey, before you know it, 2026 planning and everything's going to be here. But let's be real, most teams are still guessing when it comes to what's actually working in marketing today, which channels to double down on, which campaigns are worth running again or not. What's just noise, what's actually contributing to Pipeline and what's not. It's Messy. This is B2B marketing and that's exactly where Paramark comes in. Paramark is a marketing attribution platform that shows you what's working and what's not so you know exactly where to invest your next dollar. They use marketing mix modeling and incrementality testing to give you a full picture of performance across every channel, tactic and region. And it's built by a marketer made for marketers and right now they're hosting a special office hours on helping you with your second half of the year, planning forec and putting your best foot forward for the rest of this year and into 2026. It's not a sales pitch from them, but this is your chance to get real help from their experts that are at the intersection of marketing and planning. Bring your data, bring your questions, your roadmap and the Paramark team is going to help you figure out what's driving results, where to cut and where to invest moving forward. So stop guessing and you can plan smarter right now with the team at Paramark. But you got to grab an office hour spot. I highly recommend doing this. Pranav is awesome. The rest of their team is great. They total get this space. You should go check them out. Go to paramark.com office hours that's paramark.com office hours.