Biggest 2026 Wins, Boldest 2027 Bets: Marketing Leaders Share Takes on AI, Events, Social and Growth

0:00Colin Kendall: Dasha, remember when McKeel from Optimizely won our Exit 5 live AI agent showcase? The 2000 custom landing pages? That was really impressive. So he's their director of AI innovation and he built them with Optimizely's agent platform, one for every account in an ABM campaign. He built them from signals like job postings, press releases, and leadership changes. That's like the holy grail of ABM. That's why today's sponsor, Optimizely, is where I'd point anyone who wants to know what AI agents can do for marketing. Their agent platform is built specifically for B2B marketers. Build your own agents or pull from a directory of 50 plus prebuilt ones.

0:35Colin Kendall: They also launch virtual teammates. These are digital team members that learn over time, can join meetings, complete tasks, support campaigns, and keep your website optimized. Why do I need to go to work? Let me get those. Okay, I need one of those. Same. Being asked to look into AI agents, which I know a lot of you listeners are right now, go check out Optimizely. Put them at the top of your list and you can go build cool stuff just like Mikheel did. Check them out at optimizely.com slash exit five. Hey, quick shout out to Webflow, who is also sponsoring today's episode. Their team actually ran one of the highest rated workshops at Drive this year, which is our big annual conference.

1:11People raved about that one. Guy, their chief evangelist, really knows AEO, and he shared a ton of advice on turning your website into an ongoing revenue driver.

1:19Colin Kendall: And that matters a lot right now, right? AI is cutting into organic traffic. I don't go to Google and search anymore. I'm talking to my AI agents all day long. So AI is cutting into organic traffic and buyers, just like you and me, are using AI to make purchase decisions about 95 % of the time. Webflow, they're a great team to follow on this. More than 300 ,000 brands, can you believe that, build on their platform. It helps you get discovered in AI search, build fully custom sites without a developer, govern your content, and see how agents read it all in one place. And they just launched Webflow campaigns.

1:50Agents help you write a campaign brief from your brand system, then generate on-brand landing pages and matching ads together.

1:57Colin Kendall: Check it out at webflow.com slash exit-5 and make your website your biggest growth engine in 2027. That's webflow.com slash exit-5. You're listening to the Exit 5 Podcast.

2:22What's up? It's Dasha. And the episode that you're about to hear is a special one. It was recorded live in Stowe, Vermont for Exit 5's Drive event. And it's kind of a mishmash of me talking to a bunch of marketers that I deeply, deeply respect. I got to sit down with them live and I got to ask them all the same question. I asked them, what is your big bet for 2027. As marketers, we always want to know what is the next big thing? What are people doubling down on? What are they betting on next? And so it was really interesting to hear everyone's response. Without further ado, here it is. Biggest win of 2026, one personal and one professional.

3:03Colin Kendall: All right. Because you're a human. Yeah, professional. I think we have the best version of the Exit 5 team that we've had. You're a manager, you're a manager of people. I think I said this last night at dinner, but like most of the problems with a business is mostly who, not how problems, you know, they say. I like that framing a lot. Yeah. Yeah. And so I think it's like, I think this is a simple business. And Dan used to get mad at me when I'd say that because he think, I think he felt like it was like diminishing what we do. Right. But my point is like, it's not the thing that we're building is not complicated.

3:38Colin Kendall: It's like, it's content it's a newsletter we take the feedback we do this thing it's not where you're not putting you know we're not saying rockets into space right um and we've had all these ideas but you can't execute them yourself you need the right people to do them and we went through some pain with you know hiring and firing and you know onboarding and that stuff sucks right people is really hard and i you know it's emotional it's hard uh bringing on someone new is hard because you don't always know instantly if someone's going to be awesome. Yeah. There's nine people on the team right now.

4:12Colin Kendall: And it's, it's, you know, as you'd hope every iteration should be better. The team is really, really, really good. Any personal wins? It's not one particular win, but I think like something that I'm proud of is I think if you look at me on LinkedIn, if you just look at that, you'd think like I wake up and I'm like B2B marketing, B2B marketing, I live and breathe that. I think if you found me offline, like I'm a very, I'm a very good dad and husband and I'm very proud of that. And I've had some bad role models in my past and I'm happy to be like, I think I'm as good as a, I'm as good of a parent and father and husband as I am at like this side of things.

4:51Colin Kendall: But there's no format to like flex about that or to be that. And I'm just, I'm proud of that. And what is your big bet for 2027? I think we live in a world of like more, more, more, more, more growth, growth, growth, double, triple, quadruple, da, da, da. I think we have a great business right now. I think we'd like to grow it a little bit next year and just continue to raise the bar on quality. And our number one goal is to be our goal is to be the number one resource for B2B marketers and to have Exit 5 continue to be like it used to be like Dave. Dave and Dave has exit five. I think it's to continue to surpass that.

5:29Colin Kendall: And I just happen to be the guy who like started the company. But people know Dan and they know Dasha and they know Anna and Allison and Maria and Marissa. Like that's that's the goal. I don't I don't really have a big goal. Honestly, it's like, let's just do let's just keep doing a little bit better. Double down. Yeah. Double down. Is that that's not a cool answer. I'm sorry. No, but I feel like it's the simple answer. You know, we have a good thing. I just want to keep, we're just going to like keep getting better at it and keep sharpening the sword, you know? What was your biggest win in 2026?

6:00Dasha: The biggest win that I had in 2026 would have probably been a lot of the partnerships. Like I've been partnering with a lot of brands to create content, helping them like with their actual stories through my team at Foundation. And Foundation has just grown and built an amazing team. So I would say the biggest win is actually building the team. The team that we have at Foundation and the work that they do to be able to go into some of these top brands in the world and influence their culture amid so much change would probably be my biggest win, even though I didn't actually do it. So my biggest win of 2026, let me put this on a bumper sticker, would be the ability to create a culture where my team can go into these organizations, do best in class work, and really move the needle for these clients on an innovative problem, which is AI visibility, and then translating that into pipeline.

6:56Dasha: It's been really cool to see. And the fact that they're doing it without me, and so many of them are better than me now at Reddit, at LinkedIn, and stuff like that is just like chef's kiss. That's what it's all about. That's beautiful. What is your biggest bet for 2027? My biggest bet for 2027 would be that there's going to be a massive surge in in real life events. I think people have loved the internet and AI and social and all of that. But I think there's a real desire amongst buyers to get together with real people, build those connections in person. I've always been a digital first person.

7:32Dasha: I love the internet. I built my career on the internet. But there's something special about going from pixels to flesh. And I think it will never be replaced. And amidst the rise of AI, I think it's becoming more and more of a necessity. Hence the reasons why some of the top AI firms in the world are starting to actually hire for these community and events roles.

7:49Colin Kendall: Quick break for Zoom webinars. This is the platform behind the world famous Exit 5 Live. Someone on LinkedIn just said, I compare all other webinars against Exit 5 Live now. How good is that? So good. I want to print that out, send it to my mom, put it on my fridge. In a world of AI slot, we just want to make something that's worth showing up for, even a webinar. Especially a webinar. But don't you dare call it a webinar, even though I'd break my own rule and do that all the time. It's a live session. Our team puts over seven hours a week into each one of these, choosing the topic, the prep calls, building to run a show and making it valuable and engaging.

8:25Zoom webinars is a big part of how we pull it off. We average 1500 plus registrants per session. Hundreds of people show up live and the chat goes off.

8:34Colin Kendall: Yeah. The last time we have a new high watermark. We had 527 people live for an hour with us. Zoom does registration, emails, polls, analytics, and it all lives in one place. So running a polished session every two weeks isn't a scramble. At Showtime, our team swears by Zoom's production studio. They preset every scene and push each one live on cue. Clean transition, zero chaos, at least that anyone can see. Just please do not look at our internal Slack. Okay, all the caps lock in there. Don't share that. That's our pro-level webinar production powered by Zoom. Check it out, zoom.com slash exit5.

9:08Colin Kendall: Learn more about Zoom and all the webinars and all their products there, and come see it live. We do these basically every week now. Go and check them out. It's called Exit 5 Live and learn more about Zoom at zoom.com slash exit5. All right, if you're at a B2B tech company spending over$50 ,000 a month on paid media, Compound Growth Marketing wants to give you two free sessions to build out your 2027 plan. Free? Okay, I'm listening. What do you get? I know free is usually too good to be true. But check this out. In the first session, they're going to learn your business. And in the second, they will deliver you a custom plan.

9:42So you'd know how to split demand capture and creation, which channels drive the best ROI and where you're reporting has gaps.

9:48Colin Kendall: And look, I trust them with it. I've hired CGM twice. They're one of the best agencies I've worked with back in my day as a head of marketing. Twice. Wow. I've hired plenty of agencies as a VP of marketing, and that is rare. I'm more than just a thought leader, Dashiell. You should know that. So CGM helps high growth cybersecurity and enterprise software companies show up earlier in the buying journey with full funnel, paid media, AEO, and a dedicated GTM engineering team. Ooh, and a former VP of marketing started it. So they actually get B2B. That's right. John was one of us back in the day. So check it out.

10:20Colin Kendall: You can go book your 2027 planning session right now at compoundgrowthmarketing.com slash exit five. That's compoundgrowthmarketing.com slash exit five. Link in the show notes. What is a win for you, your team in 2026? So I grew up in California. And for my whole life in California, there was this fear of the big one. And the big one, California, if you don't know, sits on the San Andreas Fault, which is a meeting of two tectonic plates. And the big one, quote unquote, is when these two tectonic plates are going to shift and create a very life changing or earth changing earthquake that would be very bad for many people.

10:58And that was something that was always on my mind. Oh, the fear of the big one that's going to really shift and change California forever. And so whenever a small earthquake happens in California, but does not affect lives, maybe affects property or buildings, but is small enough to not be, you know, life altering. Geologists are very happy about it because it is not the big one. It's releasing a little bit of tension from the two tectonic plates. Something that I'm really proud of with my team is that we've done those little dissolving and little earthquakes for ourselves to disrupt what we've been doing this whole year.

11:34Every week, like we're not waiting for the big one where someone comes and says, what are you doing with AI? Like every day my team has been disrupting how we do things or changing or building something new to make sure that that tension is released gradually rather than having a big, you know, shake up in a year that that really changes everything that we're doing. So I like I like to keep the disruption going because it actually helps keep consistency going so that we're there. We're never behind enough where a big one happens in a huge shift, you know, really changes everything that we're doing.

12:04So I'm very proud of that for my team. What is your big bet going into the next year? As a whole business, we are automating more of our workflows, but then also augmenting how we do ABM. So it's not going to be the same, same, but, you know, more. It's going to be different and better. But with all that automation, with all of that change to how we do, you know, day-to-day activities, I want to see what we can do different and better. So this year, we've experimented with things like account-based billboards. How do we put a billboard outside of an account in Tulsa, Oklahoma, where we're having a field marketing event that day and say, hey, we put that up for you?

12:41Like this was, you know, as if the billboard was right there. And it was like, we put this up to make sure that you saw us. And sometimes those activations are less expensive than most of our marketing campaigns. So what are we doing that's new? And then one-to-one and individualization. And we've also run and filmed and produced videos with our CMO talking to other CMOs that calls out the company name, calls out exactly their challenges and exactly our current place with that business. And we've had a lot of success with those businesses recognizing, oh, this is CMO to CMO. She knows who I am.

13:13I'm going to email her and we're going to set up a call with the rep that's responsible. So we're getting into new lines of business to make sure that. But we're getting into lines of business, but doing it in different ways than we ever have before. When you reflect back on on 2026, everything you've done and your team's done so far this year, what is what you say is the team's biggest win or biggest win?

13:33Dasha: Our growth as a team is a very easy one. And one that at an organization like Professional Services, a marketing team, it's tough. You can be seen as a cost center. You can be seen as overhead. But we've done a phenomenal job at building a team that really cares about marketing, really passionate, and spent so much time with customers, with clients, and with our subject matter experts getting in the minds of clients. And the biggest win for this year is translating that into revenue from events. We've really leaned in over the past few years, particularly since COVID. Once events started coming back, we've really been doubling down on that.

14:10Dasha: And it's been something that each year, we've been able to attribute a lot of revenue to those events. And it's an investment in time. It's an investment in resources. But what's been really effective for us is we've been able to go beyond just the sponsorship. How do you make sure that you get your people an opportunity to speak at these events. And a lot of our events, a lot of the ones that we attend are more of like the decision makers in finance technology. And they start to stack these events and they start to really, just like the way you guys do it. You start to have people that are speaking at multiple different events in front of similar crowds, different people, but you start to accumulate a lot of credibility and a lot of thought leadership.

14:50Dasha: And so what we've found is that has helped really create more of a magnet at the booth, more of a magnet in our events. And I think that we are very scrappy in how we approach that. And so where it used to be, you sponsor an event, you have an exhibit booth, people stop by, you just hope that the right person, you start to have speaking events, you start to have events with clients and prospects. And next thing you know, you have four to five touch points with folks that never knew you before that are now seeing you at an event in February, seeing you at an event in March. And what's been great is the team has done a really great job at being able to take that speaking event, that content we're creating for it, and then repurpose it and distribute it after the fact.

15:31Dasha: So it gives you a little bit more purpose, a little bit more meaning. And it's not just a one-off event. It can really start to layer on and create an experience where for a firm like SC &H, where we're not a household name, we really have to fight tooth and nail to establish a brand and to become memorable. And so when you start to see that really big companies are starting to include us in RFPs, they're starting to reach out to us directly, they're starting to connect with our thought leaders on LinkedIn, that's big for us. Whether we win that first opportunity or not, it's something where the SC &H brand continues to grow.

16:08Dasha: And for my team to be able to see the revenue dollars that come in because of that, it's huge for confidence. What are you betting on in 2027? Perfect transition. I am betting on employee advocacy and personal branding for our leaders. We absolutely took a step in the right direction. And by the way, this is not like I'm putting myself out there on some crazy bet. But in our world, it is still something that is a little bit less familiar and comfortable. Obviously, in the marketing world, I think we all understand and we all are comfortable putting ourselves out there. We're thinking like marketers.

16:45Dasha: but we are still seeing a lot of people embracing it, adopting it. And what we're going to do next year is make bigger bets, not just in the time that we're spending and the budget that we're spending, but how we're helping them put themselves out there. But one of the things that we really believe very strongly is that we need it to be theirs. How can we help you gain confidence, inspire you, come up with ideas, but you have to be the one that's crafting this. because when folks meet you in person, you want to make sure that the online persona matches the in real life persona. Totally. And figuring out how you make it easier for thought leaders that are strapped for time is something that is just not a perfect science.

17:26Dasha: But the more that we can invest in time, in training, and in dollars, that's a bet that we're going to make next year because that's going to lead to more speaking events. It's going to lead to more prospects and clients knowing who we are. And also, it's going to help with clients understanding and being proud of the people that they're working with and understanding their perspective and that it transcends just their engagement. And I think that that's something that we're going to double down on and triple down on next year. And I think we could take a lot of playbooks from the Exit 5 team too, right?

17:57Dasha: What you guys are doing right now, I know you're not on the Exit 5 team, but you are absolutely an extension in the face of that in some ways now. but the challenge that they're going through to really become more comfortable putting themselves out there and being the thought leaders they are, that's what I want to see SC &H do.

18:20Colin Kendall: Hey, real quick, before we wrap up, I just want to give a quick shout out to all the stuff that we're doing at exit5.com. You can get on our newsletter there. A couple times a week, we're going to send you some really useful stuff about B2B marketing. Our whole mission is to help you get smarter about B2B marketing and get better at your job. In a world where everyone is talking to AI and Claude about how to do marketing, our whole pitch with Exit5 is real insights from real people. We've built our whole business around it. You hear it here on the podcast. You'll see it in our newsletter. And check out all of our stuff.

18:51Colin Kendall: We are creating the number one resource for you, B2B marketers. So go and check it out, exit5.com. Get on our newsletter. You'll find all of our podcasts, links there, show notes, all of our webinars, articles, and a bunch of other stuff. Plus, you can also join our community over there. So check it out, exit5.com.

19:11Colin Kendall: The best marketing leaders have a strong agency or two backing them up. And Convertive is one I'd put on that list, especially if AEO is a priority for you right now. It definitely is. And a good one is a lifesaver. They bring fresh creative angles and go deep on specialties like AEO when your team's short on bandwidth. If you're shopping for a B2B agency, check out Convertive. They help enterprise marketing and ops leaders grow revenue across the business. Who do they work with? They work with legit companies like DocuSign, Databank, and Constructor, and they build on the search work that you're already doing, optimizing your site so more buyers find you and turn it into pipeline.

19:48And this month, Exit 5 listeners get a free AEO search snapshot. They'll run your buyers real questions through Google and AI tools, show how you stack up against competitors, and tell you what's worth fixing.

19:59Colin Kendall: So if you're building your AEO strategy for 2027, start here. Go and check out convertive.com slash exit five. That's convertive.com slash exit five. And you can see the link in the show notes.