2.7: How Paid Ads Help You Start the Right Conversation with Your Buyers (Caitlin Seele)

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This is a podcast episode titled, 2.7: How Paid Ads Help You Start the Right Conversation with Your Buyers (Caitlin Seele). The summary for this episode is: <p>When Kris Borja talked about auditing playbooks on the podcast last week, he emphasized the importance of contextualizing a playbook to the journey a site visitor is on. To get that context, understanding where that site visitor came from can be very helpful. That's where paid ads come in.</p><p><br></p><p>Caitlin Seele is the Head of Digital Marketing at Drift. In this episode, Caitlin joins Sammi to talk about how Drift thinks about its paid ad strategy. She shares examples of the thousands of tests we run weekly, how her team works with the sales team to characterize site visitors who came from a paid ad, and how Drift eats its own dog food in the world of digital.</p><p><br></p><p>Like this episode? We'd love it if you could leave us a ⭐️⭐️⭐️⭐️⭐️⭐️ review! And make sure to subscribe, so you never miss an opportunity to learn more about starting conversations in the Revenue Era.</p><p><br></p><p>You can connect with Sammi on Twitter @sammireinstein and @DriftPodcasts and Caitlin on LinkedIn.</p>

Sammi Reinstein: Hey, this is Sammi Reinstein, and you're listening to, Conversation Starters. On this show, we talk all about bringing conversations back to B2B marketing and selling. Because if there's one thing we know about doing business in the revenue era, it's that the best customer experience wins. Through the power of our own conversations with drifters, customers, and special guests, we'll learn how to deliver a sales and marketing experience that puts the buyer first. Let's get into it. Hey, Elizabeth.

Elizabeth: Good morning, Sammi.

Sammi Reinstein: Good morning. Happy National Donut Day. Free Donut Day? National Donut Day.

Elizabeth: National Donut Day, but you can get free donuts on National Donut Day, if you know where to look.

Sammi Reinstein: Yeah, that's true. Did you get a free donut?

Elizabeth: I, of course, did. Dunkin Donuts. Or Dunkin', excuse me.

Sammi Reinstein: I saw an ad for that, for free donuts.

Elizabeth: Well- targeted advertising, perhaps?

Sammi Reinstein: No, I actually really did, and I probably wouldn't normally get a donut, but how can you not? It's a free donut.

Elizabeth: Well, I mean, with purchase.

Sammi Reinstein: With purchase.

Elizabeth: But you were going to drink coffee anyways, so you might to get the coffee from Dunkin', and then get the free donut. They know their audience.

Sammi Reinstein: I am a Dunkin' iced coffee girl, so I'd get an iced coffee and a donut. But I would say that was a timely, relevant ad for me.

Elizabeth: I would say so, too. Perhaps you're alluding to something, such as paid advertising?

Sammi Reinstein: Yeah, yeah, yeah. Not to be-

Elizabeth: Not to be coy or anything.

Sammi Reinstein: So on the nose, but today I am really excited to talk to Caitlin Seele, who runs our digital team at Drift. And she had some really great insights into paid advertising and not just the ad itself and getting people to click, but behavior on how to continue a conversation with retargeting.

Elizabeth: I think one of my favorite things about having Caitlin on this show specifically is that she's been in a variety of different roles of marketing at Drift. She's seen a lot of the different channels and how they work together. Now seeing her work in paid ads, it's really cool to me to see how she continues to build those customer journeys and start conversations through advertising, which is definitely not the easiest thing to do.

Sammi Reinstein: And I do think that paid advertising sometimes can get a bad rep, and Caitlin really helps clear up some of those misconceptions, myths in how to do paid advertising really well. So, enjoy. Caitlin. Thank you so much for coming on Conversation Starters.

Caitlin Seele: Yeah, totally. Happy to be here.

Sammi Reinstein: Can you just tell our audience really quickly a little bit about your background and what brought you to Drift?

Caitlin Seele: Sure, yeah. So I'm Caitlin Seele. I'm the Head of Digital Marketing here at Drift. What I'm most passionate about is building truly integrated digital experiences with the brand, and really thinking about how we can always push ourselves as marketers to get more personalized and just have more relevant contextual, in the moment conversations with folks, throughout their engagement with any brand really out there under the sun. I started off in smaller tech and startups, helping to start companies and run smaller marketing teams. Now I'm over here at Drift, really leading that whole interconnected digital experience engine, everything from our website, our own use of Drift here at Drift, here at Meta. Also, what I'm excited to talk about today, which is the deeper work we do in paid advertising.

Sammi Reinstein: Specifically on that, with paid advertising, what is the general strategy? How do we think about paid ads at drift? I mean, it's a loaded question, but how do we use paid ads? How do we think about that?

Caitlin Seele: I think paid ads gets a lot of conversation and attention from marketers for a good reason. It's a place where most marketing teams spend a significant portion of their budget. It's ads and advertisement. So they want to get the most ROI from that investment. But I think what we skip over because of that hyper focus on generalizing ROI and optimizing ads is not just, are we sending an ad out there into the world that's going to get a lot of clicks, but is it going to be the most relevant, impactful message for your audience. So when we think about it here at Drift, it's all about starting with the who and the audience first. That's something we all learn like Marketing 101 at some point in our careers, but it's so easy to like get away from that and be so focused on the metrics and the results that you forget, all right, wait, at the end of the day, I'm talking to this person who has these problems and these pain points. What's going to be the right way to like reach out to them or engage them with anything? Whether it's an ad, an email, a conversation on your site. So that's such a core pillar, I guess, for how we do our marketing strategy here.

Sammi Reinstein: And it's interesting what you said too. People love paid ads. They're a great way to start conversations. We can get somewhat caught up in vanity metrics, like what is getting the clicks. That's so exciting to see, that something you're putting out there is getting clicks. But then you have to follow through and it's, what's starting the most meaningful conversations here, not just what's getting the most clicks.

Caitlin Seele: Exactly. There's a big difference when you move from what's going to generate the most conversions on this book or webinar, whatever the offer is, to what's really going to help someone solve their problems and move them through our buying process. The answers are sometimes the same, but oftentimes they're really different. Knowing what works for which audience at what time is a really key part of developing a super effective ad strategy.

Sammi Reinstein: What else do you see in terms of myths around paid ads? What can you help us debunk around paid advertising?

Caitlin Seele: That's a great question though, Sammi. I think the second myth for sure that's at least we're thinking about right now is that the experience or engagement with your ads stops as soon as they hit your landing page. It doesn't. Retargeting is such an important thing in advertising specifically, and really connecting through like, all right, we know that you saw and engaged with our ad, whether that's on LinkedIn, Facebook, Instagram, a display programmatic platform, whatever the case may be. How can we use that engagement to further learn what you're interested in and apply that learning to hyper personalize your next experience with our brand? Again, whether that's email or retargeting ad on display, a specific offer we're going to promote even more to you now that we know that this is the kind of content you're interested in, really thinking about how you're going to leverage that data to make it actually useful and impactful in your business, and not just stop there with the reporting.

Sammi Reinstein: That's so interesting. So it's not just thinking about we have this new book or we have this new offer, so we need a paid ad for it. It's we have this new book, it's about this persona. How can we start a conversation with this persona and then how can we continue the conversation and retargeting?

Caitlin Seele: Totally. You think about it, if you were two people in person at a conference or some sort of event, it's like," Oh, how are you liking this event?" And someone tells you what they think, and then you just forget and come back and ask them the same exact question three days later. Right? It's really frustrating and annoying. It's like," I told you this once. I demonstrated interest. Show me more of this. Recommend what I should check out about this event or a next event that could be good for me. That's what I'm really interested in learning about. I don't want the same question twice. I want to feel heard and like you're listening to me." So many B2C brands do that exceptionally well. It can be done. It just takes a little bit of thought and effort.

Sammi Reinstein: One part of paid advertising is that it does have the word paid in front of it. So, there's some money going towards this and it is an investment. What would you say to companies who are trying to ramp up that strategy, that they really think through before they put that investment in?

Caitlin Seele: It can be very easy to launch ads quickly, which can make it a really good place to get started in terms of if you want to AB test, like what kind of message is going to resonate with a certain audience. You can really quickly spin up a couple ad variations right, and get some real time in the moment data. So I encourage folks to just rip the band- aid and start. Definitely, at first, think through again, who that audience is, what they're going to be interested in, and what you have in terms of your marketing arsenal that might be most interesting to them at that point. But then once you've got that basic pillar, just go. It's really easy with advertising to stop, start, continue in terms of pausing variations, keeping variations on, tweaking the copy or the creative that you're using. Testing is your best friend when it comes to the advertising world. It's really easy to monitor that spend for your different tests and course correct if you need to make a change.

Sammi Reinstein: Tell me a little bit more about testing and variations. How do you go about deciding like," We want to test this or we want to start a test with this." What is that strategy as it comes to variations?

Caitlin Seele: Totally. We're probably writing even just for some context maybe more than a hundred tests at any given time in our advertising platforms. Across whether it's like an audience test, a copy test, a creative test, whatever the case may be, so you certainly want to like create a single source of truth, like documentation, and set some broad goals. Maybe you're trying to figure out what message is going to resonate with someone at a certain stage in the buyer's journey. What's going to get them to connect with sales and book that meeting. Write out your hypotheses. Picture it like it's your middle school science class in terms of like, is it the actual offer? It can be sometimes as simple as the color choice and making sure the color scheme of your ads is going to contrast against the blue backgrounds of most social media platforms. But really documenting your task, letting it run, and then making sure you go back and also document the results so you can learn from that over time just helps you keep track of all the experiments you have going on, and also ensure you're covering your bases, so to speak, in terms of the different kinds of tests and different kinds of answers that could be out there.

Sammi Reinstein: That's awesome. What sort of tools are you using for ads generally in testing?

Caitlin Seele: That's a great question. We use so many different tools for this. Again, it really depends on the channel and the right tool could be so different for every business. But I always recommend folks, get started with advertising, get some data, like I said. From there, you're going to determine pretty quickly which channels are giving you the most ROI and enabling you to reach the most people in your target audience. There's different answers in terms of the testing tools that could be good for paid social advertising on LinkedIn and Facebook versus display advertising. Really, anything that's going to enable you to target your ads and test based off of previous engagement or intent. There's so many different tools that can do that. You know, I know 6sense, Metadata, there's so many different tools that can do that, but they all have different answers in terms of the types of advertising they're best for. But they do have a commonality in terms of enabling you to learn from past tests, apply those learnings and increasingly optimize an algorithm.

Sammi Reinstein: I love that advice though of just starting and starting to see what channels your audience engages with the most, and then determining the tools that may be most appropriate. I think that the more you can have data back to recommendations for the business, the better.

Caitlin Seele: And advertising's one of the few marketing channels where you really do get that firm real time data. So use that to your advantage in terms of informing your testing, where you're going to place the budgets. Don't just let stuff run for a quarter and do a retro in terms of what worked or what didn't. Because you can check real time progress and insights and adjust as you go. It's really flexible and very low- risk, I think, from that perspective if you are paying attention to the data and the metrics. It's really easy to identify what's working and what's not and learn from that pretty much week to week or even day to day.

Sammi Reinstein: You mentioned intent a little bit earlier. How do you characterize someone who has clicked on a paid ad?

Caitlin Seele: That's a really good question. I think it's important to talk about the different kinds of intent. So, one might demonstrate, right? If you're a company and again using ads for your business, you probably have some sort of measure of like a lead score, a lead quality score internally that you can use to almost quantify the value of activity, I guess, people are taking on your website. Are they just browsing more top of funnel resources or are they really checking out your pricing page, requesting a meeting, that sort of stuff? But I think it's really important to layer on action- based intent as well in terms of like, maybe somebody hasn't actually got onto your website and requested to see your product or talk with a salesperson, but maybe they've spent two hours with your pricing page open on a certain tab on their browser. There's a ton you can do and glean in the advertising world that makes it really flexible to say like, create a remarketing audience if you visited this set of pages like your pricing page, your case studies. They're really looking to hear what your customers are saying and how people are using your product. You can create a whole advertising audience just through that alone so that you can again get more personalized in terms of," Hey, I saw you were exploring this topic. Would you be interested in this?" Makes it feel like much more of a Netflix- like recommended for you experience versus like," Hey, here's our newest book. You should read this." Sometimes that's the right answer. Sometimes it's not.

Sammi Reinstein: It's behavior, not just clicks.

Caitlin Seele: Exactly.

Sammi Reinstein: That sort of... like that Netflix example. Netflix is looking at, sure, what you're watching, but how long did you watch it? Then from there, are you watching things that are similar. Then it gets more and more sophisticated from there the more you watch.

Caitlin Seele: Totally. And if people are letting you know about their interest and engagements, that's also such a huge trend right now in terms of when we think about cookies and their place in our marketing tech stack over time. Advertising today relies a ton on cookies. But if you're able to get that first party data in terms of what people are doing on your own website or the things they're telling you, whether that's in chat, on the phone, with someone from your company, regardless, if you can develop a really good motion for recycling those first party behavior- based insights, that's a real game changer in terms of how personalized you can be.

Sammi Reinstein: With that behavior and the insights that you glean, how are you working with the sales team? What does that alignment look like from your team and the sales team?

Caitlin Seele: It's so, so important. When I was talking a little bit about the importance of retargeting, this is also where the importance of communicating the sales comes into play too. It's everything that happens post- click. You, can't just optimize your ad and then let it stop there and say," Oh, they'll hit our website and whatever happens will happen." It's really important to develop a regular cadence of sharing the campaigns you're working on with sales and also enabling them to just give them context in terms of," Hey, if you're seeing someone click through on this ad, here's what that means," in terms of like, here's the audience they're a part of. We know they're in this group of intent bucket, they visited 20 pages on our website about the same topic, they must be really interested in this. Also, not assuming they're familiar with every single offer you have like we marketers are, and taking a beat to explain. Then they downloaded X or signed up for Y. Like, here's what that means. Here's the content that's going to be covered. Really, anything you can do to just pass along that information, and use the knowledge that we have on the marketing side to really contextualize the why that matters and what it could mean in terms of how it connects to how you can help.

Sammi Reinstein: At Drift, we do get to drink our own champagne, eat our own dog food, whatever you want to call it. And we know that chat is a really important part of our paid ad strategy. Like you said, the conversation doesn't stop once they reach the landing page. That's really sort of where it begins. So can you talk to how we use Drift for paid ads, and maybe some best practices that you might have?

Caitlin Seele: Totally. So if you're just getting started in terms of really personalizing that first click experience for somebody, your experience in chat can really be a quick win because you don't have to customize like a full landing page. You know what I mean? You can really just be more personalized and engaging in the moment of intent when they want to talk to you. So, that makes it super easy. We do have a paid ad converter playbook that we use here at Drift. Even in our own marketing too, so we definitely benefit from that, which does do some kind of basic personalization in terms of," Hey, saw you're coming over from LinkedIn, Facebook, Instagram," whatever the channel is. That can add an immediate personalized touchpoint that just gives someone's attention in terms of like," Oh, hey, they're acknowledging me and where I came from and what my interests might be." But you really don't want to stop there. Because if you think about it, every brand, every email is going to do some sort of Hi insert token here. Whether it's Hi insert your first name, insert your company name, insert where you came from, it's definitely important and the expectation for marketing today. But what's more important is what happens after that initial greeting in terms of make it really easy for them to get whatever you're promoting and advertising, whether it's an event a book, what name you. But then suggest that personalized contextualized next step in terms of like," Thanks for downloading. Here's your copy. I'm going to send it to you in an email." All the basics we might do. But then if you're interested in learning more about this topic or if you're experiencing this common challenge, here's what I'd recommend for you next, and being very intentional and thoughtful in terms of what that next step is. That can be great for marketers in terms of even like exposing other kinds of content that maybe you don't get as much organic traffic as your website. Maybe it is a YouTube video, a podcast episode, a related webinar you're doing on the same topic. That's a great time to continue the conversation and really be engaging someone while they're in that moment of highest intent.

Sammi Reinstein: Retargeting and being thoughtful in that next step is all about continuing the conversation. And that is so important, and it makes me feel good if you know my needs and thoughts, and it's not just some generic," Here's this next thing you could do," or" Here's a demo." It's really taking into consideration where I am in the buyer's journey, and I'm more likely to click into that if it's relevant to me.

Caitlin Seele: Totally. Again, it draws that connection between here's how you talk to a buyer online, to here's how you'd engage with them if you were in person. Having a real conversation. You'd recommend that right next step or how you can be even more helpful while you're talking to them. In that conversation moment, you wouldn't say," All right, bye. Nice talking to you," and then run up to them in the hallway three days later with," Oh, here's another book you might like." That's going to be like," Whoa, what are you talking about? I've already moved past this." You want to be as helpful as you can be in the moment, and that also just feels most natural for the buyer as well.

Sammi Reinstein: What would you say to people who in different businesses or people who aren't as comfortable with the hyper personalized targeting? What would you say to someone that says," That's a little creepy," if you say like," Thanks for coming from LinkedIn," or something around the retargeting journey.

Caitlin Seele: It can be creepy. Totally. One of the other aspects of advertising is yes, you get a ton of data, but also you have a ton of targeting options in that channel, just in terms of... especially if you're working with LinkedIn, Facebook, any of the social media platforms, you can really hyper target, not only to certain locations and geographies but even very specific interests someone's demonstrated. And yeah, that feels creepy. We've probably all gotten that ad of something you just bought. Or we're talking about it and you see an ad for it two days later, and you're like," That was a little too odd." So what I tell people is to go back to the testing conversation we had earlier here and just test and see what works for you. Every audience is different, and you'll figure out where that" break even" point is in terms of personalization that's going to make an impact, in terms of making it more engaging, and stuff that people are bouncing out of, closing out of, or where the metrics just level off. A great example I like to tell people is, if you're doing, say, a super highly personalized campaign, maybe even ABM, sometimes the company name, in personalizing things for a specific company name, really doesn't make that much more of an impact as personalizing for a role or a job title or a core interest set could be. It's a lot of added work to personalize at that very one- to- one level, but sometimes, depending on the campaign, depending on the audience, you might find that it's also not worth it from a marketing perspective and that could be where you pull back.

Sammi Reinstein: Caitlin, thank you so much for coming on the podcast. I have learned a lot. I think you gave some great advice as it comes to paid advertising. When it comes down to it, it's a lot about being intentional, being thoughtful, and making sure you're finding ways to continue the conversation past just that click.

Caitlin Seele: A thousand percent

Sammi Reinstein: Elizabeth, you could say that Caitlin is one smart cookie. Get it? Cookies? crosstalk

Elizabeth: Yeah, so moving on. That was a good one, Sammi. Yes, Caitlin is definitely one smart cookie. I love hearing new use cases for Drift from Drifters. Because obviously it's no secret we both work at this company, but I don't always know how everyone's using the product and she had some great examples, I think.

Sammi Reinstein: Caitlin's such an expert in her craft and it's nice to talk to someone who's so passionate and also really customer- centric and buyer- centric when thinking about paid ad strategy, which is definitely a pro for anyone that's thinking about investing in their own paid ad strategy.

Elizabeth: And I think, like we said at the beginning of this episode, paid ads, we all get them all the time. It's something that we can all really just think about our own experiences, what works, what doesn't, and how to avoid being that annoying paid ad, and making sure that when you click, you're going to the place that you're looking for, that you want the best content from, and from there, starting a conversation.

Sammi Reinstein: It's all about continuing the conversation. And speaking of continuing the conversation, we're really excited for our next episode, which is the last of the season, so rounding out the season with a very special guest, Amy Jo Martin, who will talk about continuing this conversation in social media. Amy Jo Martin has worked with lots of top brands including the NBA. So, it's a very, very fun conversation and we can't wait to see you there. Thanks so much for listening to Conversation Starters. If you like this episode, please leave us a six- star review by clicking the link in the show notes, and hit Subscribe so you never miss another one. You can connect with me on Twitter at Sammi Reinstein, and follow all of our shows at Drift podcast.


When Kris Borja talked about auditing playbooks on the podcast last week, he emphasized the importance of contextualizing a playbook to the journey a site visitor is on. To get that context, understanding where that site visitor came from can be very helpful. That's where paid ads come in.

Caitlin Seele is the Head of Digital Marketing at Drift. In this episode, Caitlin joins Sammi to talk about how Drift thinks about its paid ad strategy. She shares examples of the thousands of tests we run weekly, how her team works with the sales team to characterize site visitors who came from a paid ad, and how Drift eats its own dog food in the world of digital.

The Highlights:

  • (2:46) How Caitlin came to Drift
  • (3:44) How Drift thinks about its paid ad strategy
  • (5:46) Caitlin debunks myths about paid ads
  • (7:58) What companies should be thinking about before they invest in paid advertising
  • (9:11) Drift’s paid ad testing strategy
  • (12:29) How to characterize someone who has clicked on a paid ad
  • (15:03) What alignment between Drift’s sales team and digital team looks like
  • (16:47) How Drift uses Drift for paid ads
  • (20:17) The line between creepy and personalized retargeting

Like this episode? Let us know by leaving a review!