Staying Human in the World of AI Marketing, with Jessica Gilmartin [Episode 1133]

In this episode, Howard and Alastair are joined by Jessica Gilmartin, CMO at Calendly, to explore the impact of generative AI on marketing strategies. They discuss how AI tools are revolutionizing content creation and leading to increased efficiency while emphasizing the importance of maintaining human creativity and emotional connection in marketing to ensure customer engagement and long-term success.

Podcast Transcript:

00:00:18:07 – 00:00:45:14
Speaker 1 (Alastair Woolcock)
Welcome back, everybody, to this week’s Sales Strategy Enablement podcast. I’m Alastair Woolcock. CSRO here at Revenue.io joined by my co-host, the famous revenue science expert Howard Brown, CEO and multi-founder. And we are super excited to have a special guest with us today, Jessica Gilmartin, CMO of Calendly, formerly head of revenue marketing at Asana, a graduate and pioneer from Wharton School of Marketing Strategy.

00:00:45:14 – 00:01:08:05
Speaker 1 (Alastair Woolcock)
And Jessica, we’re thrilled to have you with us. You’ve been through some successful rides, other rides, and lived through it all as it pertains to marketing and growing scaling companies. Welcome. Thank you. I appreciate you calling them other rides versus failures. So thanks very much for that. Well, when I was a gardener, I did a lot of work around your Wall stores and these growth companies.

00:01:08:05 – 00:01:30:08
Speaker 1 (Alastair Woolcock)
And look, I tend not to look at them as failures. They may not have driven the financial results, but they sure do drive the education and learning. And while we’re in it, at least we’re helping people, inspiring people, whatever that. Absolutely 100%, Howard. You know, as Jessica has been through, some of those rides I know is near and dear to you as well in terms of growing and scaling these companies.

00:01:31:09 – 00:02:06:02
Speaker 1 (Alastair Woolcock)
But we have had a busy week, as always in the news, a busy week in the world of generally by and as we have Jessica here, I think we really wanted to dive into today its impact on marketing, what it means to go to market. But I must start with this kind of news thing that CNBC just came out with a couple of days ago, and that was looking at the world of marketing, and they said, and I’m going to read a quote from the article in terms of how we market work now, the output, the quality, the value they were able to put out.

00:02:06:02 – 00:02:29:21
Speaker 1 (Alastair Woolcock)
Now you can get this personalized. The result of using generative AI is completely changing everything in marketing, and they go on to say that, you know, basically even just ad copy, basic stuff like that, what took 30 minutes before is down to 15 or 10 minutes when Jessica now out I think of that, and we’re seeing this, and that’s a very basic example, I think.

00:02:30:20 – 00:02:55:09
Speaker 1 (Alastair Woolcock)
But also, I don’t know that I have seen in the past two decades something that this quickly is reducing time to value by by 50%, 60%, 70%. What’s your thoughts when you hear that article from CNBC? It’s really interesting. And obviously, you know, we can’t get through 15 minutes without talking about it. So I get it. And it’s incredibly setting.

00:02:55:15 – 00:03:19:16
Speaker 2 (Jessica Gilmartin)
I’d also say we have to be really careful and really thoughtful because so much of marketing is still about the connection and the emotion that you create. And it’s about a deep understanding of your customers and your products and how your product can really provide value to your customers. And so AI is a great enabler and a great tool, but I still fundamentally believe it has to come down to the people and the creativity.

00:03:19:17 – 00:03:39:21
Speaker 2 (Jessica Gilmartin)
And I don’t think that changes. And so I worry a little bit that and from what I have seen talking to other marketers, that they want to skip past the creativity and the beauty and the magic and the art and go right towards the efficiency. And I don’t know that that in the long term is actually going to do any of us disservice.

00:03:40:08 – 00:04:09:19
Speaker 3 (Howard Brown)
Howard, what do you think when you hear that? And I want to cue in on something Jessica said there on the empathy side and the emotion side. Yeah. So as we’ve always talked about, I believe that AI is really a tool to help augment human intelligence, to augment human creativity, and how we use artificial intelligence to help us move from the mundane to the real human connection, helping us really connect with other people.

00:04:09:19 – 00:04:44:20
Speaker 3 (Howard Brown)
And certainly empathy is a big part of that. If you think of empathy as really understanding where someone’s coming from, their situation, the context around that, we can’t just ask machines to do that for us. We cannot ask machines today to simply replace the human connection. And I think great marketers and, Jessica, it sounds like you’re clearly one of them, obsess on what is important to the customer, where the customer’s needs meet and fit what we provide for them.

00:04:44:20 – 00:05:17:04
Speaker 3 (Howard Brown)
And so there’s that alignment of customer understanding and then the value we provide the customers. And if you are out there talking to your customers, if you’re not understanding your prospects, it makes it incredibly difficult to just ask AI to generate something for you because even the best AI requires you deliver both context. You know, when you’re prompt engineering, you can’t just say, Hey, right this piece of marketing, you have to come up with all of the parameters.

00:05:17:09 – 00:05:43:09
Speaker 3 (Howard Brown)
How you understand those parameters involves doing the research, spending time with customers, talking to your teams, and then providing that to the tool to then generate for you. Yeah, exactly. And it’s so interesting. I always think generative AI is a misnomer because it’s not actually generating anything new. It’s by definition repackaging what it has understood, what it is taking from other people’s work.

00:05:43:21 – 00:06:04:14
Speaker 2 (Jessica Gilmartin)
And so somebody still has to generate the ideas, They still have to generate the understanding of the customer and understanding of what is new and what is fresh and different. And I can be an enabler to help you to make sure that the tone is right and to give you a bunch of different options. But it is not generating anything new.

00:06:04:19 – 00:06:36:22
Speaker 2 (Jessica Gilmartin)
So what is your biggest concern in terms of when you hear something like the article or the piece that Alastair was talking about? How will that negatively impact expectations from the C-suite, from our customers, from our teams? What are you seeing as potential downside impact? Well, I see it’s so much like the growth of SEO, right? So about ten years ago was when everybody started 15 years ago is when everybody started to generate huge amounts of content so we could all rank for Google’s algorithm.

00:06:37:06 – 00:06:52:17
Speaker 2 (Jessica Gilmartin)
And so that became the thing that everybody had to do. And that became that thing that marketers were told to do, which is pump out enormous amounts of content. And so we did that, and they were really poor quality content. And there’s still lots of companies that do that and lots of companies that are told that we have to do that.

00:06:52:17 – 00:07:15:08
Speaker 2 (Jessica Gilmartin)
And so I worry a little bit about the same thing, which is the expectation is that we just put out a lot of very generic content because that’s considered successful, which is volume equals success. Whereas I, you know, I always want to focus on quality, and I also focus on business results. You know, my, my job is not to generate an enormous volume.

00:07:15:13 – 00:07:42:23
Speaker 2 (Jessica Gilmartin)
I mean, as efficiently as possible of content. My job is to help hit the company’s revenue numbers. And so I believe the way to do that is not just by putting out a bunch of generic contents, it’s by the brands that people love and that people believe in and are passionate about and putting out really high-quality work that creates a connection between my company and my customers.

00:07:42:23 – 00:08:04:19
Speaker 2 (Jessica Gilmartin)
Yeah, so it’s the quality versus quantity argument that I have, an efficiency argument that I’ve seen for many years. Yeah, and I think I would also just correlate it to the amount of outreach that people do via email has just become complete spam right? It’s useless. And even though they try and personalize it, personalization at scale typically hasn’t worked.

00:08:04:19 – 00:08:38:12
Speaker 2 (Jessica Gilmartin)
It’s just created a lot of noise. So the question becomes how do you actually use these tools for personalization, for context, for taking the creativity and making people not only more efficient but then more effective. And I want to press on that piece to you both. What is personalization? Because I see I think a lot of people and no offense to my the marketing marketers of the world, but a lot of times the personalization is will we look to the person’s name?

00:08:38:12 – 00:09:04:09
Speaker 2 (Jessica Gilmartin)
I found some fun fact about, you know, something that they like and oh, by the way, I slapped some industry stuff on there that they had. Yeah, right now it’s better than not doing anything, I suppose. But is that really the goal we’re going for in personalization? Yes. So I would say not. I mean, the number of emails that I get from salespeople that say, Hey, I saw that you worked at Google and went to Wharton, and I was like, No, I do know my resume.

00:09:04:09 – 00:09:25:02
Speaker 2 (Jessica Gilmartin)
Thank you for sharing that. And listen, I have deep empathy for salespeople as a tough, tough job. But I agree that’s not relevant. One of the things that I find most important about personalization perspective, which is why we lead very heavily to intent tools, is really about understanding what are the priorities of the company, what are the priorities of the people that to you.

00:09:25:10 – 00:09:46:18
Speaker 2 (Jessica Gilmartin)
So for me that that to me is personalization, which is what are the top priorities of the company that you’re trying to reach and what do they care about and who are the people that care about it? So, you know, I get so much outreach. And the reality is, is that I’m not the one that is responsible for demand generation.

00:09:46:18 – 00:10:10:11
Speaker 2 (Jessica Gilmartin)
I have somebody that is responsible for that. I’m not the one responsible for PR, I’m not the one responsible for marketing. And so doing your homework and figuring out the person that lives and dies and thinks about that 50 hours a week, that’s the person you have to reach. And then understanding what they care about and what are they searching and what are their teams searching that to me is the most effective way to market and sell to somebody.

00:10:10:15 – 00:10:31:11
Speaker 2 (Jessica Gilmartin)
I would agree, by the way, and I think back to the Garden of base, everyone would agree with that. Jessica, overall, I want to frame it this way, though, as I think about that, where I think the challenge is I happened to be in a meet up just Monday, just just a short time ago. And then there there was CDO and C, So from a big city, I won’t name which one.

00:10:31:19 – 00:10:51:17
Speaker 2 (Jessica Gilmartin)
It was also a couple of other people. That one was from a very big hospitality company and stuff like that. And they all want to talk about generative, they want to talk about what it was. And like I would say, I’m on the spectrum of I’m a big believer in AI adoption, where it’s going and provocateur and all of these things and think it’s going to really disrupt a lot of areas that people aren’t thinking about.

00:10:51:20 – 00:11:12:00
Speaker 2 (Jessica Gilmartin)
And I was struck because in that conversation they were the ones actually pushing me going, We think you’re wrong. We think this is actually total replacement displacement of some of the marketing functions, some of these sales functions. I said, Well, don’t talk to them. People still need I went down the personalization route, a modicum of personalization. They need some of that.

00:11:12:00 – 00:11:38:06
Speaker 2 (Jessica Gilmartin)
I said, maybe, but they said, but honestly, when we run the numbers between good enough and volume, good enough understanding of a certain situation, good enough in terms of getting within the ballpark of a price to drive and engagement, they go so far that yours are looking better than what the people can do. So so it’s an interesting thing where we go, all right, well, are we actually staring at a resurgence like we saw when SEO came along?

00:11:38:20 – 00:12:00:02
Speaker 2 (Jessica Gilmartin)
Are we actually about to see a massive uptick on volume because you can actually just be good enough to drive an incremental result rather than this kind of protecting. What we we know is right, we know it’s better to be more empathetic and look at customers and really understand that. But at the end of the day, I’m just trying to drive pipeline.

00:12:00:10 – 00:12:31:15
Speaker 1: Yeah, I totally understand that argument. And I would say that that is a pretty shortsighted argument because the companies that are successful in the long term and that drive long term brand value are ones that create really beautiful brands that speak to their customers, that understand their customers and provide value. And you saw that with Echo. I mean, there is just so much out there and for a short period of time, it works and then people stop visiting those sites.

00:12:31:15 – 00:12:53:21
Speaker 1: They stopped on Google, got smart about how it ranked content that was just not that high quality and not that relevant. And people have to spend a lot of time on it. Not only what are the keywords, but what are the calls to action and what is the path and what’s the journey and what happens when somebody hits a page? You know, what is the right path for them afterwards?

00:12:54:01 – 00:13:18:13
Speaker 1: That’s all human. I just don’t think that you can ask a computer to think about all of the different ways that human beings interact and engage with your content and ultimately end up engaging with your team. So I completely believe and 100% believe that I will take some jobs and it will take a lot of the mundane and automated tasks off of Aarti, which is fantastic.

00:13:18:21 – 00:13:39:10
Speaker 1: I don’t want a copywriter writing 150 versions of an ad. I think it’s fantastic that I can do it, but I absolutely want a copywriter who is working with my product marketer. I’m working with my brand team to come up with the first ten versions of it because I just believe over the long term that that’s the way that my company is going to be successful.

00:13:39:10 – 00:14:14:02
Speaker 1: And I’m happy to compete against companies that don’t believe that because I don’t think that they will be successful in the long term. I love the gauntlet competition set. We should get a bucket of companies and put them in it and see. But I would tend to agree with you, Jessica. And it’s a point we tried to make in the roundtable the other day that augmented AI, I think is the that that’s where you’re going to see the big game where I think anybody wants it is easy to jump to the news headline of displacement but augmenting is always a better way and I think that’s actually where the real results kick in.

00:14:14:02 – 00:14:46:05
Speaker 1: And Howard, you’ve spent a long time now, and not just in general, but years in the airspace. And I would say augmentation is exactly where you see this going. And it’s what’s worked in changing behavior, changing engagement to date. What do you think about that roundtable discussion? Well, I think the jury’s still out in many ways. I think we we’re learning on a daily basis where to apply this technology and where we can, you know, see benefits both in terms of efficiency and effectiveness.

00:14:46:11 – 00:15:10:22
Speaker 1: One thing for all of us to consider is the very definition of work. You know, how we think about what people are employees, what human beings are doing with their time, what should we actually automate, what should we get rid of? We talk about the word mundane or repetitive tasks like as human beings. Is that really what we want our people doing?

00:15:11:05 – 00:15:45:10
Speaker 1: Or do we want them connecting with other humans? Do we want them to use things that make us uniquely human? Our creativity, our passion, our empathy, those sort of things? So I think it’s an opportunity to look at our employees, look at our companies, look at our expectations for the people we have, and let’s start changing some of the requirements of their jobs, their descriptions, and figure out how we can rather than just get rid of people, start to train people on the skills that really matter for not just today, but for the future.

00:15:45:10 – 00:16:09:04
Speaker 1: If you just poo poo generative and you don’t understand how to empower your employees to use it every day, figuring out a way, give them 20 minutes, spend time on chats to think about ways that you could use this technology to improve your performance to make you better at work, you’re probably missing the mark. But we Jessica, you talk about 50 hours a week.

00:16:09:04 – 00:16:39:19
Speaker 1: Employees. Great. Giving them 5 hours. Give them 2 hours to use generative and come up with different ways that will help them be more created, more effective. And let’s see what comes out of it. And Jessica, as I think about this going forward as well, you know, I think a lot of the times one of the struggles we often have in enablement and sales and the coordination with marketing and in general where that fits in, you’re rolling out a new product, you got a bunch of new hires, you’re scaling the company.

00:16:39:19 – 00:16:58:07
Speaker 1: We’re doing a bunch of things. Well, I wish they were on Brand point Boy, I wish they would just ramp a little bit quicker on our story or, you know, you get in marketing and new new people that come in and well, I got an idea and grade. I like that you got an idea. But also we have a series of things we’re trying to just reinforce and get to marketing to scaled.

00:16:58:07 – 00:17:20:05
Speaker 1: And in some way, we’re talking about a lot of the risks of what it can do. But where does Generative fit in on what it can do for helping scale product launches, helping scale enablement, helping scale and drive consistency of brand message in every conversation? How are you thinking about that from excellently? How do you think about that Previously from other places?

00:17:20:20 – 00:17:40:21
Speaker 2 (Jessica Gilmartin): Yeah, I would say that is by far the number one way I’m excited about using is definitely that tone check. We, for sure, have that issue here and recorded at every company Upwork that when you have 40 writers among different team members underwriters one different team members, everybody is going to have a different way of working and really hitting.

00:17:40:21 – 00:18:09:09
Speaker 2 (Jessica Gilmartin): And no matter how many style guides you create and no matter how many proofing processes you have, you still have this issue where people don’t understand how to really fully express the tone and the voice and the brand. And it drives me, but it’s actually kind of things. I think I drive my team bananas because I am constantly and harping about it, and I have a very particular way that I want to have the brand expressed, and it’s something I learned at Google, and it’s something that we did Sana, which is very much about human speak.

00:18:09:17 – 00:18:29:03
Speaker 2 (Jessica Gilmartin): It’s very and it’s keeping a very positive, very constructive, very focus on customer use cases and inspiring. And we’re constantly veering off in other directions. And so I am very excited about AI as that final editor and the final check around the tone in the brands. So I could not agree more that that is how we use it.

00:18:29:03 – 00:18:48:16
Speaker 2 (Jessica Gilmartin): That’s how I always will want to use it. And I actually have a very funny story, if I can, Deborah, for a little bit. Yeah. So I have an amazing event coordinator and leader, and it was one of my first weeks here, and we were trying to figure out the backdrop for one of our conference boots and, you know, sort of a tagline.

00:18:49:00 – 00:19:06:06
Speaker 2 (Jessica Gilmartin): And given that this is my first, you know, the first time I was reviewing something, and she kept coming back to me over and over again with these very formal, stiff, very typical marketing speak. And I was like, No, that’s not right. No, that’s not right. It’s got to be humans barbecue. And it came back to me finally with the perfect human speak line, I was like, That’s it.

00:19:06:06 – 00:19:32:00
Speaker 2 (Jessica Gilmartin): And she’s like, Yeah, I threw it as attached to upset. What’s like, perfect! So we got our cue and three. Very cool. I think it’s amazing. Jessica, We, I could go on all day on this and the impact, and I think, you know, we’re just so the tip of the iceberg and we’re only just beginning to think about the possibilities of what can occur here and how that’s going to back marketing through enablement all the way through to, you know, the brand story to our customers.

00:19:32:05 – 00:19:55:00
Speaker 2 (Jessica Gilmartin): But we are out of time. So and I have to pause here. We always love to kind of wrap up each session with asking you to choose from three facts going to throw at you relative to today’s conversation and see if you can figure out which is the right one, the wrong ones, and go from there. So are you feeling ready and terrible at these?

00:19:55:00 – 00:20:28:04
Speaker 10: But sure, lots of cracker hair, Big, big pressure. Big pressure. Big pressure. Here we go. Alright. So recent articles suggested that brands are increasingly using generative AI tools to create digital ads, digital copy, digital content. True or false? More than half of the brands are now using generative AI tools across the Fortune 500 space. More than half of them are using generative AI tools to create digital content ads and engagement, making copywriters as endangered as pandas.

00:20:28:09 – 00:20:56:07
Speaker 10: Number two, Generative AI has been adopted by more than 90% of the Fortune 500 companies for their marketing strategies, making it the most popular employee next to the coffee machine. Number three, Generative AI can now accurately predict customer behavior up to three years, 36 months in advance, making it better than your local psychic.

00:20:56:18 – 00:21:20:19
Speaker 2 (Jessica Gilmartin): Oh, your a go a a is. Brands are increasingly using AI to create digital content copy that is more than half, more than 50% of the Fortune 500 now using generative AI to do so, and that is correct. Yes. Preparing very well. That’s the first time I’ve ever gotten one of these random things. Correct. So I feel pretty proud.

00:21:20:23 – 00:21:44:22
Speaker 2 (Jessica Gilmartin): I saw the idea that, listen, it is fantastic having you on here, Jessica, final question. We love to talk about moments. We talk, we’ve all had moments in history. We’ve had things we’d love to redo or we’d love to see happen in the future. When you think of a special moment that you would love to create, the final word is yours. What does that look like to you? What? What’s the moment you want to create going forwards in this world of generative AI?

00:21:45:03 – 00:22:05:18
Speaker 2 (Jessica Gilmartin): Well, before we started recording, we were talking about our kids and so of course it always has to come down to my kids. So can I say that I would say that the moment I want to create forever is the ability for me to continue to having his my kids forever. And they not be horrified that their mom is still without actions.

00:22:06:02 – 00:22:25:01
Speaker 10: I could not agree more. And we had the discussion and there’s nothing like when your child tells you that you need to lay off the affection, and so just take it all in, enjoy it. And yeah, I guess also remember that probably giving Mom and Dad a hug and kiss is probably pretty important for each of us as well.

00:22:25:05 – 00:22:42:08
Speaker 2 (Jessica Gilmartin): Absolutely. And in British for me, I’m going to take that advice, run it through chat, CBT, and just get some parting words of wisdom from it. On how to apply both of your emotional states to my own life. Good luck and see if I can improve my hug ability. Jessica, It’s been a pleasure having you. Thank you so much.

00:22:42:09 – 00:23:13:18
Speaker 2 (Jessica Gilmartin): Thank you so much. For those listening in, please are able to like and subscribe. Plus call in your questions hardly listen to those and attempt to address them on future episodes and have yourselves a wonderful after it.