#263: Inside Customer.io’s B2B Marketing Strategy: Org, GTM, and Growth Channels with Jason Lyman

#263 Marketing Strategy | Dave is joined by Jason Lyman, CMO at Customer.io, a customer engagement platform used by over 7,500 companies. Jason has led marketing at Dropbox, BetterCloud, and now heads a 30-person team driving growth across both PLG and sales-led motions.

Dave and Jason cover:

• How to structure a B2B marketing org for scale, alignment, and channel ownership
• Why events are their #1 channel and how creative formats drive real pipeline
• The KPI + OKR system they use to prioritize work and measure marketing’s impact

You’ll walk away with a clearer understanding of how to design your team, focus your strategy, and invest in channels that actually drive results.

Timestamps

• (00:00) - – Intro
  
• (02:34) - – What Customer.io does and who they serve
  
• (03:34) - – Growth story: from bootstrapped to private equity-backed
  
• (05:34) - – Team size and breakdown of the 30-person marketing org
  
• (07:34) - – Balancing PLG and sales-led within one team
  
• (09:34) - – How the org is structured: focus teams vs. centers of excellence
  
• (11:34) - – Aligning team goals to sales motions and funnel stages
  
• (13:34) - – How Customer.io prioritizes internal marketing requests
  
• (15:34) - – Avoiding the “who bangs the table loudest” trap
  
• (16:34) - – Cross-functional alignment with sales and product
  
• (18:34) - – KPI vs. OKR: how Customer.io uses both
  
• (22:50) - – Examples of key KPIs for the business
  
• (24:50) - – How OKRs cascade across the org
  
• (26:50) - – Why structured goal setting leads to better marketing impact
  
• (28:50) - – What channels are working: events are back
  
• (29:50) - – Examples of creative event formats that build community
  
• (31:50) - – Building pipeline without pitching at events
  
• (33:50) - – How Customer.io defines and tracks long-term influence
  
• (36:50) - – The decline of SEO and rise of AI-influenced buying
  
• (38:50) - – Why positioning is more important than ever
  
• (40:50) - – Product and marketing alignment in a modern org
  
• (42:50) - – Selling both the product and the roadmap
  
• (43:50) - – Jason’s one wish for marketers: better customer data
  
• (45:50) - – Personalization, adaptability, and breaking through the noise
  
• (46:50) - – Closing thoughts

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Dave Gerhardt [00:00:00]:
You're listening to B2B marketing with me, Dave Gerhardt. Hey. My guest on this episode is Jason Lyman. He's the CMO of Customer.io. I just wrapped up recording with him. I got a bunch of notes. We had an awesome conversation. They have a 200 plus person company at Customer.io.

Dave Gerhardt [00:00:30]:
About 25, 30 people on the marketing team. We talked about how they set goals, OKRs, KPIs, their marketing strategy, the team set up the structure, what's working in marketing right now and what he's invested in in the past. That's not working anymore. It might be SEO. It might have to do with AI. We talk about why meeting in person is so important, why events are back so hard right now in marketing. If you're a B2B marketing leader and just want to get inside of a high performing company with a top cmo, you're going to like this conversation. I got all these notes to prove it.

Dave Gerhardt [00:01:06]:
Here's my conversation with Jason Lyman. Hey everybody. Thank you for listening to this episode of the Exit Five CMO podcast. My name is Dave Gerhart. I'm the founder of Exit Five, host of this podcast. I used to be a marketer, Jason, in my past life. I'm just a thought leader now. I don't really do any marketing anymore, but I get to talk to the people who are.

Dave Gerhardt [00:01:28]:
I get to talk to people like you on this podcast. And I'm super excited to have you here today. This is my guest, Jason Lyman. He is the CMO of Customer.io. Jason, thanks for coming on the podcast.

Jason Lyman [00:01:39]:
Hey, thanks for having me. I'm super excited to chat more.

Dave Gerhardt [00:01:43]:
All right, so first of all, people who don't know Customer.io, give me the elevator pitch for who you all are and what you do.

Jason Lyman [00:01:51]:
Yeah. So Customer.io is a customer engagement platform that helps marketing teams build campaigns and journeys that engage and convert. We do that by helping you orchestrate all of your communications across email, push in, app, sms, pretty much whatever channel you want to use. I think we can help you deliver on that. You know, I think we're really unique in that we take a very data driven approach to kind of supporting those efforts. So we help you leverage your first party data to really drive campaigns that are contextual and adaptable based upon how customers are engaging with your brand. So we have well over 7,500 customers today. We support companies large and small, and we're here to help.

Dave Gerhardt [00:02:37]:
Awesome. Okay, and what's the overall like? As much as you're allowed to talk about publicly, obviously this is different as a private company, but just the roughly stage size of Customer.io. It's an interesting story in that like I remember using the product maybe over a decade ago and it's one of those SaaS companies that has been around for a while and just like kind of slowly kicking ass behind the scenes. At least, at least that's my perspective on it. So how do you talk about the stage of the company publicly?

Jason Lyman [00:03:05]:
Yeah, so we were bootstrapped for over 10 years. And so I think that's a lot of part of the reason why I've used the phrase that we're like the hidden secret inside of Martech, because people maybe not be aware of us as a brand and that's something that I'm actively trying to change. But we.

Dave Gerhardt [00:03:22]:
It's funny interviewing the cmo, you're like, yeah, yeah, it's so great, man, it's so great. Nobody's heard of us.

Jason Lyman [00:03:27]:
Yeah, it is. I think we've made some really, really good progress since I joined. But yeah, we took some investment from Spectrum Equity about two years ago which has really helped us kind of accelerate our growth and our ability to really invest in the platform and our marketing and really add sophistication to our broader go to market. And so while I can't get into the like nuts and bolts of revenue, I think we're, I don't know, to use kind of existing terminology, we're probably closer to like a series C or series D type of company as far as kind of scale and growth. And so hopefully that helps to kind of put it in perspective for folks. So we are very much not a, a startup. You know, we are a kind of mid stage maturing business that still has a ton of kind of upside and potential.

Dave Gerhardt [00:04:13]:
Yep. I guess I used to always ask like how many people are at the company and then now it's like these new startups are like we have six employees and we've done 7 billion in revenue. So yeah, but my sense is like, let me just guess, like let's say 200, 200 employees and 12 people on the marketing team.

Jason Lyman [00:04:36]:
So not too bad. So we're closer to 275 employees and on the marketing side we're almost 30. We're probably like 30. Wow. Okay, 27, 28. And again, I think part of that. Right. Stems from, you know, we support on the marketing side both a sales LED motion and a self serve motion.

Jason Lyman [00:04:57]:
And so given that we have this dual go to market approach, our marketing team is maybe a little bit bigger. Than you maybe had expected.

Dave Gerhardt [00:05:06]:
Yeah, I mean, what do I know? I don't know. Like I said, I'm a thought leader. I'm not in the funnel, I'm not at all the events, but 20, 27, 28 marketers on a company of 275 that is, I'm not a math guy. 10%. Absolutely not. Crazy. You've mentioned this a little bit, but actually maybe first let's start here. How do you define the ICP of Customer.io? Where I'm going with this is one of the challenges that I see from a lot of our members in the Exit Five community and just kind of around our content and just marketers in general over the years is like the challenge of selling to you got the low end and the high end and you got the enterprise and you got the self service.

Dave Gerhardt [00:05:44]:
How does that play into your marketing strategy as a company?

Jason Lyman [00:05:47]:
Yeah, I mean I think the easiest way to think about it is kind of how our business has evolved. So we started out as a very PLG focused company. Naturally we tended to support very small businesses to small businesses. And then what we found is, is as we continue to invest in supporting the kind of efforts of these marketing teams, we found that over time our product got more sophisticated and our customers were kind of pulling us up market with them. So we were kind of growing with them. So I kind of really define kind of our ICP today is any marketing team that wants to take a more data driven approach to how they market. You know, we could support companies of a couple thousand employees, but we also are approachable for those smaller even startups that are just kind of getting going. You know, our startup program today is super successful and we actually offer free access to our solution for as much as 12 months to help those kind of younger, more immature marketing teams kind of get up to speed and help them really drive product market fit in that really important stage where they're trying to figure out what is their product going to be and what is their ICP solution or ICP customer.

Dave Gerhardt [00:07:01]:
I guess if I could just like kind of crack through this layer a little bit and talk specifically to not even people who are interested in, not people who are going to use Customer.io's product one day. Think about the marketers listening to this show and they're like, I'm at my company and it's challenging because we have competing Personas or multiple segments. And so you've seen this at bigger scale at your last couple of companies. What I'm curious is like how does this play out into the marketing strategy. Like, are there different segments of the business that marketing has goals around? Revenue and pipeline around? Because I was at a company one time and we of the challenges was we traditionally kind of had a lot of inbound demand from smaller businesses and then the gravitational pull of the company was to go up market. And then so much of the marketing goals and the things we're doing in marketing actually were supporting the wrong audience. And it created a lot of tension and friction inside of the company. And so I'm always interested in hearing from marketing leaders as to like, how do you set up the org to be successful? Is it quite literally we have a goal for this channel and this segment and they're responsible for filling it.

Dave Gerhardt [00:08:07]:
Do you have shared resources? I'm just kind of curious, like on the marketing strategy side of things, how you would explain some of how the inner workings are there.

Jason Lyman [00:08:15]:
Sure. So at Customer.io, we've kind of tried to design our org to support both the kind of broad user journey that companies kind of go through as they engage with us, as well as the kind of scale that we have across these kind of dual go to market motions. And so the structure is really centered around three what I call targeted focus teams and then two centers of excellence. And so the targeted focus teams, they have this really kind of deep sophistication around certain aspects of our marketing strategy. And so at Customer.io we have a PMM team that's responsible for storytelling across the entire kind of customer journey. And then they work with our demand gen team and our marketing growth teams, the other two of targeted focus teams, to then figure out what is that specific narrative that we want to tell to really help them achieve their goals. And then within the demand gen team, we've actually become much more opinionated around the specific funnel that they're focused on. So within demand gen, you're either aligned to our sales led funnel or you're aligned to our self serve funnel.

Jason Lyman [00:09:25]:
So that way you don't have these competing interests where I have to figure out how do I balance these kind of broader needs where they know what their core metrics are and what they need to drive.

Dave Gerhardt [00:09:36]:
Yeah.

Jason Lyman [00:09:37]:
Even further, within self serve, we have someone who's over trials versus someone who's over our startup program.

Dave Gerhardt [00:09:43]:
Nice. Okay, that's exactly what I was trying to get at. Hell yeah. Thank you. And can you just break down the. You have three targeted focus teams and then two centers of excellence. And so which one of those is demand gen? And maybe if you could explain Those three and two.

Jason Lyman [00:09:56]:
Yeah. So the three targeted focus teams are demand gen marketing growth and product marketing. And then the two center of excellence teams is our brand studio team and our marketing ops team. And so because those teams have these very defined skill sets, they need to be able to flex those across the kind of broad ICP that we support. And in some ways too, like they're responsible for driving that kind of consistency across so that we don't over rotate towards supporting one aspect or the other. Because clearly when people make requests of those teams, like they want it to be optimized for their specific goals and metrics. And so they're kind of the countermeasure, if you will, to make sure that we don't lose sight of our brand guidelines or that we don't overinvest in a certain funnel at the expense of another one.

Dave Gerhardt [00:10:43]:
Nice. Okay, that's really useful. And I love the model of like even just the framing of them, like the centers of excellence, like we have creative and brand that sit across the whole thing and support each team. I just saw this question come up today, so I'm curious if you have an answer to it, but how does the creative and brand team in your org. He knows where I'm going with this. How do they manage the request? Because it's like it's always the most burning thing for that team. And I have yet to find a great system to do this other than what used to call it, don't get me in trouble for this. We used to call it drug deals.

Dave Gerhardt [00:11:20]:
And so whoever could be good at, better at the drug deal was like, you know, I'm super tight with the designer. So like, I'm going to get her and we're going to get this thing done behind the scenes.

Jason Lyman [00:11:29]:
Yeah. And so this problem is not unique. I think everybody has to kind of figure out the best way to solve that. I think the way that we try to do it@Customer.io is first and foremost we have good clarity around what are our North Star metrics and what are our kind of okrs for the quarter. And so we try to look at decision making through what do we need to prioritize to support our kind of commitments across those areas. So it tries to take the emotional side out of it versus we try to think holistically as a team of what's the most important to help us achieve those goals. And then honestly we have a weekly sync where the kind of leaders of those targeted focus groups are meeting with the brand studio team or the marketing ops team and they then debate what is the prioritization for the week, looking at it through that lens of what's needed to help us achieve our goals. And so that's where the kind of push and pull kind of comes and avoids, you know, use drug deals.

Jason Lyman [00:12:29]:
I use like who bangs table the loudest. Like that's typically like how I've described it is I don't want to get into a world where that becomes what drives our decision making. And so if we have this North Star that we're going towards, it takes the emotion out of it and, and then it allows us to make more data driven decisions or more kind of evidence based decisions versus emotional decisions. Which is why I feel like where you get yourself into trouble and then you find yourself kind of over rotating into over investment in areas of your marketing strategy that probably are not optimal.

Dave Gerhardt [00:13:01]:
Yeah, totally. That's super helpful. You mentioned whoever bangs the table the loudest. Something that I think about even with my own small and growing company now is, and I think something that I struggled with as a marketing leader is like each team has goals. And so you're demand gen person, you mentioned demand gen growth, product marketing, brand ops. Right. Each one of those teams has their own goals. But what makes a great team is like you have people kind of all rowing in the same direction.

Dave Gerhardt [00:13:28]:
And even though somebody might serve the small business side of the funnel versus enterprise, like I want people on the team that are really never going to say like oh that's not my job. And so I'm just going to let that thing, you know, I'm not going to help figure that out. Have you found a way to solve for that? Like a mentor of mine has said, like he didn't believe in, he used to be the CMO of HubSpot, was a great marketing leader there. He didn't believe in like individual bonuses, that the bonuses on performance should be based on the company goals. How do you incentivize the team in those scenarios to do what's right for the business so the business can win and say yeah, you know what, actually it's okay if we prioritize this other team's thing, it's going to make my week different. But I'm down to prioritize that.

Jason Lyman [00:14:09]:
I found that you know, aligning a measure of success around a handful of Northstar metrics is like a great way to accomplish that. And typically those North Star metrics are cross functional in nature so they don't have this incentive where it's one team that is only Thinking about that. And I think part of it too is like is everybody talking about those metrics in that same way? So I have a really great revenue partner. John's the CRO of Customer.io and he and I work really, really well together. And one way we try to foster that across our teams on the sales led side for instance, is we talk about pipeline broadly across the kind of go to market motion. So we never talk about well how much of that is marketing source versus how much of that is outbound versus how much of that is partner. Because that's where you get into these like confrontations where you're arguing about attribution, you're self interested and trying to kind of hit that overall target. And so it's not that we don't monitor those and we set goals for those, but in the end we gauge success on did we hit the overall pipeline number? That's the most important thing.

Jason Lyman [00:15:17]:
And then we use the underlying metrics to drive some of our decision making around changes that we need to make. But I think that that by anchoring everybody on that higher level North Star metric, it avoids some of that confrontation that might exist and drives the right incentives. And I think you can use that in a variety of different ways depending on how you work with your respective cross functional partners, or how you structure incentives, or how you structure kind of recognition and making sure that you're rewarding people that think about that holistic company first approach versus being so anchored in their personal goals and kind of aspirations or even their departmental kind of goals and aspirations.

Dave Gerhardt [00:15:57]:
You mentioned the OKRs. So I like to ask people what kind of goal setting methodology they believe in. For you all it's okrs.

Jason Lyman [00:16:05]:
Yeah. So we use two, we have KPIs and okrs. So KPIs are kind of those, let's call them can't miss metrics. Like these are the ones where if you don't get a hundred percent attainment, it's a fail.

Dave Gerhardt [00:16:17]:
And so give me some of those as you go through it. What are some examples of those?

Jason Lyman [00:16:21]:
Yeah, so an example on the KPI side is very much like your revenue target, like for the company. This is your churn rate, this is your logo retention rate. All things that are really designed to assess the kind of health of the business. There also tend to be metrics that are harder to move in the short term. So they tend to have a more kind of slower evolution and kind of a longer term focus.

Dave Gerhardt [00:16:46]:
And then what would be an example of that?

Jason Lyman [00:16:49]:
Well, I think that churn rate, I think is like one of those. Because the reason why people decide to churn it's not because of like a thing you did in that month related to the product, it's the experience that they had over the course of their subscription that caused them to feel as though they needed to make a switch. And so that's something that you can't really dramatically change within a week or a month or even a quarter. And so that's why it serves better as kind of a KPI. And it's also just a good indicator of a certain stage in that kind of customer journey. Because I think in the end the best KPIs are the ones that span all different stages of the funnel. So you're not thinking, you're not over rotating too much towards the upper funnel or the mid funnel. And so that I think is one way to capture that.

Jason Lyman [00:17:34]:
So like the KPI's that stand out to me would be like ARR net expansion, NPS logo retention rate, some type of like product health metrics. So like a Customer.io. One of our KPIs is the number of like active message sending accounts, because messaging is the core way that we deliver value. So it's like what percent of those accounts are sending on a weekly, monthly, quarterly type of basis. So those to me are like good examples of KPIs. They can fall in that bucket of 100% you don't want to miss. And then OKRs, OKRs are designed for you to stretch yourself and to push your team. So you want OKRs to be more aspirational.

Jason Lyman [00:18:15]:
And so I consider OKR to be green if it is 85 or 90% of the target because you set something that was really going to push you. And if you don't quite get there, but you make really, really good progress, to me that's still success. Because you want to create this incentive for your team to be aspirational in their efforts and really pushing the limits of what they believe they can do within the kind of timeframe. And so OKRs are a really great complement to that kind of KPI construct and ensures that the team is really operating at its kind of highest level of efficiency.

Dave Gerhardt [00:18:50]:
And do those OKRs, like you mentioned, you're the CMO, the Croatia, you two have a good relationship. Do those OKRs come from first, the management team, executive team is setting goals for this year, this quarter, and then you're going to kind of read them out to your team and then you're going to go set okrs based on those.

Jason Lyman [00:19:09]:
Yeah. So okrs work best when it's a cascade. So we have company level okrs that again, we believe if we execute on those will deliver against the KPIs. And then those company level OKRs are then effectively the kind of North Star that we use to build our quarterly marketing OKRs. And then each department looks at it in a similar way. And so all of this kind of ladders up into a quarterly plan that across different departments that we believe will get us 25% or more towards whatever we've committed at the company level okrs perspective. And so that drives that kind of alignment that needs to happen so that you don't build your okrs kind of myopically without thinking about what the other departments are doing.

Dave Gerhardt [00:19:58]:
Yeah. So the reason I love to ask all of this stuff in this podcast is because I want to ask you about marketing channels in a little bit, but at least everything I've seen in my career and then now validated by like all of the discussions we see in our community and just around our ecosystem. I'm curious to hear your opinion. You've worked at Dropbox, you've worked at Better Cloud. Like, you've seen really successful marketing orgs. So much of the success as a marketer is not did we have the most creative marketing campaign idea. It's like, how much do we have our shit together with, like, what purpose does marketing serve in our company? What are the goals? How do these things all fit together? It's very rarely the case that the marketing team is not busy enough. Usually it's like everyone is ridiculously busy.

Dave Gerhardt [00:20:41]:
The marketing team is slammed, but what we're doing is not impacting our overall goals because they're misaligned somehow in this kind of like, operating system.

Jason Lyman [00:20:49]:
Yeah, yeah, yeah. I think for me, it's just there's a few things that I like to control for. Like, one, I want marketing teams to be metrics driven, because otherwise you could fall in the trap where people start to gauge success around a binary did I do something or not? Where it's like, oh, I delivered this campaign or I launched this product, or I built this asset, this marketing asset. And so you want to kind of foster this mentality around desire to deliver kind of impact and it's more around the kind of end result. And then I think the other thing is, is that I want those big bang type of moments, but they only are successful or they only are valuable if they drive that kind of impact. You know, I think too many companies might think about I don't need more fireworks, I need more flywheels. Like, I need things that are like driving this kind of impact associated with that. And so if you find something that is more of a firework, that's great.

Jason Lyman [00:21:44]:
Maybe that's like a beachhead to then figure out how you then make that more consistent and more a part of your kind of ongoing overall marketing strategy. And so I think that you have to balance those needs, but I'd rather balance them in that data driven approach and then work back with things that might feel a little more out of the box versus starting with the kind of out of the box things and then throwing a bunch of stuff against the wall and then it not working. Like that's the quickest way to get fired. I think for me it's like, it's a much more thoughtful, it's a much more analytically driven approach, but it doesn't preclude you from like doing experimentation. It's just done within this like context of this is the metric that we're trying to drive. And so then this is the experiment or this is the big moment. That is a little bit questionable, but we're willing to do to try to see if it creates this above average impact for us.

Dave Gerhardt [00:22:36]:
That's really well said. That'll be useful to a lot of people. Let's talk about the marketing, specifically the channels. And I don't want you to tell me that you do a little bit of everything because I'm sure you do, you do events. We got website content, co marketing partners. Yeah, Q2, 2025. We're recording this. I want to know, like, what are the channels that are driving growth for you today that are exciting, that you're going to invest in? Maybe it's new stuff, maybe it's tried and true stuff.

Dave Gerhardt [00:23:07]:
And then maybe pair that with what's something that worked 10 years ago in one of your last jobs but is not working as well today.

Jason Lyman [00:23:15]:
So as far as like channels that I think are performing really well, that I'm super excited about, first and foremost is events. I think that events are helping us build like real relationships. I think it's something that honestly buyers are kind of craving. We're realizing that you need that trusted relationship before there's that desire and belief to want to engage with the vendor and learn more about them. And so when we see prospects that meet the team, when they hear from our customers and how they're using the product, it builds way more conviction. I found that like our customers are our best salespeople in a lot of cases because it's very authentic. Like they're talking about their own personal experience, their own pain points, how our solution is solving it for them. And that in turn has really just opened up a brand new kind of avenue and angle.

Jason Lyman [00:24:06]:
And it's not that events went away, but obviously with COVID it kind of got, I feel like, got forgotten a little bit. And now people are realizing this needs to be a core part of a marketing team strategy. And so we've seen a ton of success with that.

Dave Gerhardt [00:24:22]:
So first of all, like retweet. Retweet. Totally agree. The thing that I've been saying a lot lately is like, I think things are going in kind of two directions. There's like the AI side of the world and every, you know, I'm being dramatic, hyperbole. But like everything is going to be automated. You know, just ask Chat GPT for your answers. And then there's this other side which is like, I think we as humans, we want, we want to get out and we want to meet people.

Dave Gerhardt [00:24:44]:
Both of those things are coming true. We've seen it in our business. In my personal life, I want to hang out more in person than I did before. And so I think there's something there. Any insight for others on like, you know, I think if I'm listening to this, I'm like, that's cool, I believe you. Events work. But what has been working? Is there a specific type of event that's working for you? Because it's almost like how I feel about webinars. It's like, I don't think webinars are dead.

Dave Gerhardt [00:25:05]:
I think probably the content sucks and the offer sucks and that's not what's working. If you're just due to Customer.io roadshow and you're just going to talk about your product at all these different places, that might not be the way. Have you found a little bit of an event playbook that that's working or something you want to do more of?

Jason Lyman [00:25:20]:
I think we are trying to avoid just running what is traditionally been called an event. So we've experimented with, I would say just formats that are a little bit different and unique. So one thing we're doing in London at the end of the month, we call it, it's a listen more event. And what we're doing is we're going to have somebody come and actually just it's going to be a musician they're going to play and so it gives them kind of a reason to come. But it's not like there's a pitch. It's not like somebody's getting up there and pitching them about it. It's literally us gathering like minded people together to have casual conversations and then be entertained by a really great musician. And it's going to be a mix of our customers and prospects and people that honestly just don't know us but are interested in networking with other professionals.

Jason Lyman [00:26:08]:
And that's not something other brands are doing. And so we've pushed the envelope in like with virtual events. Like two weeks ago we ran a Bob Ross webinar where we had our three presenters paint while they were talking about deliverability, email deliverability. And it was just one of those things where it wasn't three heads on a webinar with slides that were talking about it. You were engaging with these people. It was very casual. It was very kind of open ended.

Dave Gerhardt [00:26:35]:
And so were these people painters or did you like send them all like a kit and you're like, Dave, you're going to be on our webinar and paint while you're doing this.

Jason Lyman [00:26:43]:
So the attendees were not painting, but the painters were not professionals, like they were novices and they were out there trying their best while they were talking about something they were passionate about, which was deliverability. I do think that, you know, if you're going to run the standard event playbook, it'll be fine. But like, I think where you're going to get the differentiation is people that are trying to create these unique and memorable moments or giving them just a reason to try. Because the thing is is that a lot of your ICP is probably being hit up to do these same things. And so how do you break through the noise? And I think that whether that's in the unique experience you offer, both in how the content is delivered or just the thoughtfulness that comes into the event with the swag or the gifts or the like momentos that are kind of shared there. It's like those are all reasons that bring goodwill back to your brand and then that's gonna drive influence. Maybe in the short term, but definitely over the medium or long term.

Dave Gerhardt [00:27:39]:
Yep, I like that. I also like just the principle of like understanding that everybody else is being bombarded with ideas and things too. And so it's like, what's the thing that would get you to actually take a night out and go to an event? And how can we make sure that this is worth somebody's night? Like when we do our events, I take it very seriously that, like, look, I know how I am I'm not going to go out to three events in one week. I'm going to do maybe one or two things a quarter and if you're going to get me away from my family, like the ROI on that night better be big. And so I love that Bob Ross webinars. They're going to explode after this, after this podcast. Okay, so events. I like that I see a lot of people doing I think it's about what you mentioned is getting like the like minded people together.

Dave Gerhardt [00:28:20]:
I think dinners have been really successful.

Jason Lyman [00:28:23]:
Yeah.

Dave Gerhardt [00:28:24]:
My question back for you though is I and this is the troll listening to this which is like if it's not a Customer.io pitch, how do you possibly generate pipeline from this event?

Jason Lyman [00:28:34]:
Jason I mean I think that this is maybe a little bit of where too the blocking and tackling happens. Right. Like an event without like strong follow up from the sales team is always going to be a failure. So I think part of this is one developing a good rhythm around how you're working with your SDR team to making sure that that follow up is kind of taking place post event and not letting any of those potential leads kind of slip through the cracks. I think the second thing is realizing that some of your marketing efforts are not going to deliver pipeline in the short term, but they will deliver pipeline over the medium and long term. And I think that it's easy when you especially if you lean very heavily on a digital marketing focus. Now you're used to that kind of dopamine hit of if I invest X amount in SEM, I'm going to get X amount of leads or pipeline back. Like that needs to be a part of your marketing strategy.

Jason Lyman [00:29:31]:
But as you get bigger and as your goals get bigger, you need to take a more of a portfolio approach and so realize that some of these things will have value but it will be over the longer term. So work with your cross functional partners, with your sales leaders, with your finance person, letting people know that your strategy is going to play out over 2, 3, 4 quarters and just make sure you have the right measurement in place so that you can then come back and book those wins when that pipeline does come in the future and it all accrues back into this kind of broader approach that you're taking.

Dave Gerhardt [00:30:05]:
All right, I like events. What's your read on what's happening with more of the digital marketing channels like particular owned content, SEO, organic social with the 2025 lens in mind? Seems like people are saying a lot's changing. SEO doesn't work anymore what's actually happening inside of your company.

Jason Lyman [00:30:25]:
Yeah, I will say that you asked me about a channel that used to work, that doesn't work. I do feel like SEO is very much the one that's kind of falling into that bucket. And so part of it is really just around how can we adapt to this new world where the influence of large language models on buyer behavior is increasing pretty rapidly and we just have to be cognizant that SEO will not play a big of a role in the future. And it's going to be more important that we are finding ways to influence the way that LLMs are positioning and communicating about our product, because it's going to be embedded in how decision makers do the exploration as they kind of dig into learning about a new product. And so, you know, for me, a lot of what I'm thinking about is how do I optimize our positioning and our content for AI consumption, not just human readers. And being really, really clear around that differentiation there, because again, I think that's where a lot of that positioning is going to be anchored on. And then I think you just need to rethink your demand gen strategy. And that might mean that you're going to have to change some of the mix that maybe you had had.

Jason Lyman [00:31:33]:
And what does that kind of mean for you know what? Maybe what's worked in the past might not work in the future.

Dave Gerhardt [00:31:38]:
You mentioned it quickly there. But I think that is the most important thing right now is positioning. Like, out of all of the pieces of marketing strategy, it's not like, should we be on YouTube, should we be on TikTok? Do we need to optimize our stuff for, you know, chatgpt? Like it's going to come back to company strategy, positioning, differentiation, your strong point of view on the world, like that stuff's going to be more important than ever. And that can't just be like you and the marketing team, you know, doing one of those like, post it brainstorm meetings. That's a company strategy level thing that you have to drive. Right.

Jason Lyman [00:32:10]:
For those that don't know, my background is through the PMM leg of the stool. So I was a PMM before I was a cmo. And so I have a lot of passion about the kind of messaging and positioning side of marketing. And I think from a differentiation standpoint, as a marketer, you have to do best with the hand that you're dealt in a lot of cases. Right. Because you don't control all aspects of that. You can flex and influence how you tell the story. But you got to work with the core component parts that you do have from your product investment and strategy over the kind of years that preceded you.

Jason Lyman [00:32:44]:
And as a marketer, I think it's really, really important to too, when you think about that differentiation, what is sustainable versus what is temporary. Because I do think that you need to be pushing, you know, as a marketing team on your product counterparts to really align around what aspect of our investments are going to fall in that sustainable bucket. And as a marketer, when you have clarity around something that feels sustainable, like, that's the point that you really have to like, just keep doubling down on. Because I do think that as markets evolve, as products evolved, and honestly, as like AI is this accelerant to kind of how we operate, it's going to become more important that you're very, very clear around what aspects of your broader platform are truly sustainable. And that's where you want to really double down on the kind of positioning and messaging that you put into the market.

Dave Gerhardt [00:33:36]:
Heck, yeah. You mentioned your relationship with the Croat. I think a very underrated. You know, if you go to LinkedIn, it's all about sales and marketing alignment. Sales and marketing alignment. Da, da, da. Marketing and product alignment is like the bigger thing to me. It's like, show me a relationship with the product leader who wants to like, oh, Jason, check this out.

Dave Gerhardt [00:33:54]:
Here's this new thing that we're going to ship, you know, that relate to this roadmap thing. Like, that's the sign of a healthy company. Like, I want to be excited by what the product team is doing. I want to work with a product leader who's excited to work with our marketing team. It's not just about sales, right?

Jason Lyman [00:34:08]:
Absolutely. I think about marketing as like this bridge that sits in between product and sales. And that being that bridge is super important because you need to be filtering the information both upstream and downstream to drive the impact and influence that you want. And so product teams are only successful if they have the kind of right pulse around where the market is, where the competitive landscape is, what customers are saying. And marketing can be a really great filter, to use terminology I used before. Sales reps like to come and bang the table to be the loudest person to say, I need this feature, I need this thing. But you as a marketer, you have to be the one that validates that for them because you need to understand what is the signal versus the noise that you're seeing and then vice versa. As product is, you've influenced and you've helped product really understand where the strategy is and where it's going, then you as a marketer need to enable your sales teams to tell this really impactful kind of vision of where the product is going.

Jason Lyman [00:35:10]:
Because for a lot of buyers, yes, they're buying what's on the truck, but they're also buying in your ability as a company to deliver on the evolution of the product that's necessary for them to continue to be successful. And in a world where AI is becoming so ingrained in how products are developed, I think that piece is even more important because you're almost to buying in your belief that that product team is going to deliver the AI use cases and tools that are necessary to really get the most out of this solution as a part of their technology stack.

Dave Gerhardt [00:35:45]:
All right, last question before I let you get out of here. Go back in your whole marketing career and today I'm going to give you one wish. I'm going to be your genie. Your little ball genie in a bottle. I'm going to give you one wish that you could solve any marketing challenge. What would it be? What's something that we just haven't figured out? Is it a lot of people say measurement? What would be your one wish for this genie?

Jason Lyman [00:36:07]:
I think I would have complete access to the data that like full. A full overview of my customer and the data, data that helps define who they are and what they value. Because my belief is, is that if I have that data that drives my understanding of my prospect or my customer, then I can make my marketing extremely personalized, which I believe is going to drive the right engagement and activation that they're looking for. I can make my marketing adaptable. So as customers preferences change or how they interact with my brand, that can then influence how I market to them in the future, which is going to make sure that my marketing is contextual to them. And then with that data, I can use all of the channels at my disposal to then meet them where they are. Because in the end, if I know where they like to engage or how they like to engage, I can then create this omnichannel type of effort so that all of my marketing feels kind of right place, right time with them, which I think is then going to drive the memorable kind of moments that they're looking for and fuel the kind of action or conversion that I want out of my broader campaign efforts.

Dave Gerhardt [00:37:22]:
That's the first time I've heard that one. I. I like that. Yeah. If I know everything about you, I can get ahead of you. I think the hard part is, like, so much of the game of marketing, though, is like, I like to think that there's this, like, perfect buyer's journey. And it's like, I'm going to do step one and step two and step three. It's hard to know what's going to influence me.

Dave Gerhardt [00:37:40]:
Like, I bump into CMO friend, and she's like, dude, you know what we're using right now? You gotta try this thing. And I'm like, like, how do you bottle that?

Jason Lyman [00:37:47]:
You know, I think the only piece that I. I would push on is, is that there's not gonna be one journey that's gonna be optimal for everybody. I think as a marketer, the more that we realize that we're not solving for the lowest common denominator when we're actually trying to solve for each individual's preferences, the more successful that we're gonna be. So. And that's where to again, give a plug to Customer.io. Like, that's what we help people do, right? Like, we realize that we want to create the most kind of personalized and unique experiences that we can offer across that user journey. And if we bring that mindset to our marketing, I think there's just a lot of untapped potential that exists there because that customization is, again, what breaks through the noise, what allows them to connect, what makes it memorable.

Dave Gerhardt [00:38:35]:
And.

Jason Lyman [00:38:35]:
And so I think that's maybe why I'm, like, so influenced around data being that thing I want to solve, because I think it then unlocks so much more that I can do as a marketing professional. And to me, it's only going to become more important as buyers become more discerning that, you know, AI plays such a bigger role in kind of their decision making. And so it's like, how do I combat that? Well, one way I can do that is by understanding my customer or my prospect better than anybody else.

Dave Gerhardt [00:39:06]:
All right, Jason Lyman, you rocked it. Virtual fist bump. I got a lot of good notes here. I got a lot of good things. Had a great conversation. He's Jason Lyman, CMO at Customer.io. Go and check them out if you like this episode. I don't want your subscriptions.

Dave Gerhardt [00:39:22]:
I don't want nothing. I just want you to go find Jason on LinkedIn, connect with him, send him a message, be like, man, I heard your interview on the X5 podcast, and I thought it was great. Jason, always good to chat with you. I'll keep an eye on what you all are doing, hopefully see at some more events in the future. And I'LL see you around.

Jason Lyman [00:39:37]:
Awesome. Thanks, Dave. Appreciate it. All right.

Dave Gerhardt [00:39:43]:
Hey, thanks for listening to this podcast. If you like this episode, you know what? I'm not even going to ask you to subscribe and leave a review because I don't really care about that. I have something better for you. So we've built the number one private community for B2B marketers at Exit Five. And you can go and check that out. Instead of leaving a rating or review, go check it out right now on our website, exitfive.com our mission at Exit Five is to help you grow your career in B2B marketing. And there's no better place to do that than with us at Exit Five. There's nearly 5,000 members now in our community.

Dave Gerhardt [00:40:14]:
People are in there posting every day asking questions about things like marketing, planning, ideas, inspiration, asking questions questions and getting feedback from your peers. Building your own network of marketers who are doing the same thing you are. So you can have a peer group or maybe just venting about your boss when you need to get in there and get something off your chest. It's 100% free to join for seven days, so you can go and check it out risk free. And then there's a small annual fee to pay if you want to become a member for the year. Go check it out. Learn more exitfive.com and I will see you over there in the community.

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