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“Ali Jawin: One way that can really help is that when people come with an idea, even if it's sometimes a good idea, or we just don't know, we can point to our dashboard and be like, 'Listen, that's a great idea. However, it will cost X. It'll take this long. To make this work, we probably need to stop one of these things. Which one would you like us to stop in order to do this?' That ends a lot of conversations right there.”

[0:00:32] Sunny Manivannan: Welcome to The Peerbound Podcast. I'm your host, Sunny Manivannan. I'm so excited to have our guest on today, Ali Jawin, who's the CMO at Pontera. Most recently, Ali was the Senior Vice President of Global Marketing at Outreach, and she has had an incredible career journey that began actually, with a PhD in ancient Greek philosophy, which, Ali, makes you the first guest of The Peerbound Podcast to have that particular background. Then you've evolved beyond that into an incredible career in software marketing, having held really key marketing positions and leadership roles at companies like Yesware, RepTrak, and obviously, Outreach most recently. It's such an honor to have you on The Peerbound Podcast, Ali. Welcome.

[0:01:15] Ali Jawin: Thank you. It is so great to be here, but just this slight disclaimer that while I have a master's in ancient Greek philosophy, I didn't finish my PhD. I guess, I'm still technically a Ph.D. candidate, but I'm going to be in that stage forever. I cannot imagine at this point what would possibly make me go back. There's also the problem that I forgot pretty much every word in ancient Greek, so I would need to go back to that, and I've got zero plans.

[0:01:43] Sunny Manivannan: Let me ask you about the beginning of your career. You began your career neck-deep in ancient Greek philosophy and then made a big pivot into SaaS marketing. Tell us about both parts of that journey. What did you learn about yourself from it?

[0:01:57] Ali Jawin: It wasn't as if I had grown up thinking, I want to be a philosophy professor. I actually have met literally one person, who, apparently, wanted to do that, who's surprisingly incredibly socially normal, as you might not expect. But it was more of that in college, I thought everything was interesting and saw that philosophy had the fewest requirements, so I could actually study more and more different things. But really loved it. Loved the ancients. Found that a lot of how they approached life and living felt really authentic into having a flourishing human life and society. Having graduated during the Great Recession, I didn't really know what I wanted to do, and it didn't matter all that much, because there weren't that many jobs out there.

Then when I got funding to do my masters in St. Andrews in Scotland, it was a no-brainer. I'm going to get paid to live in Scotland and study something I find fascinating. I should definitely do this. Came back to the US for my PhD. But pretty soon saw that there wasn't a real career path there, that especially after the austerity budget cuts that humanities were being gutted, and that as I was getting older, things like health insurance, and paying my bills were actually a lot more exciting than they were when I was in college on the meal plan or whatnot. Wanted to see if anyone would pretty much pay me to do anything.

At the time, I was not sure about that. I ended up pretty much applying to every job on LinkedIn and was really surprised to get a lot of SDR roles at tech companies. Really at this point, I was like, I will try anything. The more I learned about these roles, the more I thought it probably wasn't for me in that the notion of cold calling did and to this day makes me want to throw up. That was going to be a problem. The irony of it was that also at the time, I thought having a quota was going to cause me a lot of stress. Whereas now, I live for a quota, but something I've learned about myself along the way. As I got to learn more about sales, you just naturally end up learning about marketing.

I found sales fascinating and thought that as a marketer, I could probably learn a lot of that. If you learn anything in a humanities PhD or grad school, it's how to get out copy relatively quickly. It might not be Shakespeare, but it's not going to be bad. Especially before ChatGPT, content creation was something you really needed people to crank out. I just ended up at a networking meeting at Yesware. I was talking to someone who I knew. He said, “I remember, it's too bad. You're great, but we don't have any marketing roles here.” I was like, “It's so funny you mentioned that because actually, this morning you posted one. If I learned anything, that is always do your research. You never know what you're going to find.” He's like, “Great. Let me go get the VP.”

The VP was like, “I'm not going to meet this random person who walked off the street.” Sends a manager to vet if I was normal or not. Thankfully, she said yes and met the VP. I remember him saying like, “Listen, I don't know what I need. I'm new in this role. But if you're doing a PhD in ancient Greek philosophy, you can't be dumb. Come onboard and we'll figure it all out.” Just in that one story, there were so many things I took away that really stayed with me in my career. One was just the value of preparation. You never know what is going to happen. Sometimes preparing won't pay off in the ways you expect.

When it comes to board meetings, I always find I can memorize absolutely everything. There's always a curveball out of nowhere, you'll not be prepared for. A good example was my very first board meeting at Outreach. I had everything memorized, every stat, where it was generated, how it was generated. We had our big conference coming up in three weeks. A board member said, “So, yes, the person, keynote is great, but if you could get any keynote, who would it be?” I remember my brain, I'm like, “It doesn't matter. We have this person.” Thankfully, the CEO jumped in with like, “Does anyone know Taylor Swift?” Again, you prepare for the things you can, so that when you inevitably get the curveball, you have the brain power to think about it.

The other was that you also just don't know who you're going to meet in your career, because that woman who the VP sent in to vet me not only ended up becoming a really good friend and colleague, but I actually hired her as my VP of Growth at Outreach. It just showed the people you meet along your career, you never know when you're going to work with them again. You never know. You might hire them. They might hire you. It's a really small world and those relationships, you might not know how or where they're going to go, but that is just always, always worth investing time in smart people.

[0:07:03] Sunny Manivannan: I love these first job stories because, and frankly, I think we could probably spend an entire episode just talking about the story because there are so many lessons learned from this. You have such a vivid memory of this. As do funny enough, most people who talk about their first jobs, they remember the smallest details about the search and what it took to get that job. You had to display the Great Recession, and there's so many folks looking for a job at the same time and not that many opportunities open, and go be able to do this is truly an incredible way to start your career.

[0:07:38] Ali Jawin: It's one of those things where I feel like, I'd say, across my entire career, I'm not going to say it was just luck, because that's not going to give credit to the hard work I've done. However, I do think that it is a combination of luck and preparation because I did get some really great opportunities. I was in the right place at the right time. Or the environment was such that they happened to me. Because of the preparation I had done, I was then ready to take that opportunity. Yeah, you never know. Timing's absolutely a factor. There are always going to be factors outside of your control. What you can control is being as prepared as you can, so that when these opportunities do strike, you can take them and you're ready for them.

[0:08:25] Sunny Manivannan: 100%. Let me ask you a little bit about, now you are a CMO, you're a senior marketing leader at some of the best companies in the industry. There's a long journey from that first meeting at Yesware to where you are now. I'm sure you've received some career advice along the way. What's one piece of career advice that has really stuck with you and would love to hear the story behind it.

[0:08:50] Ali Jawin: There are some really good ones. Probably, just this is more of a saying and it's from the CRO of 6Sense, Latané Conant. It is something that I always have to remind myself and I tell other people, which is that every company is on a sliding scale from hot mess to dumpster fire. You are never going to find a company that is better than a hot mess. If you're unhappy, or looking to leave, because it's a hot mess, don't. You're just going to end up in another hot mess. It might be and it probably will be a hot mess in a different way. This idea that there is some company out there where all the systems are perfect and there are no inefficiencies. Submitting your expenses is a delight and the IT systems are – It just doesn't exist.

Now, if you're in a dumpster fire, which I personally define as either toxic, or it's interfering with your family or your health, then you need to get out. Hot mess, this is life. I think one of the reasons why I find that, especially as I get more into my career is that, well one, it stood the test of time. There's no such thing as a perfect company. I think, especially as we have, we have Gen Z, we have Millennials, we have Gen X, we have all these different generations at this period of time in the office together. People have been raised in different ways, different expectations or whatnot, that just always keep in mind that there's no perfect place, that there are always going to be frustrations. You're never going to love every part of your job.

Again, if it's unhealthy, if it's toxic, you need to get out. Just to realize, perfection doesn't exist. For companies that look like they're perfect, thank their marketing team and their PR team and their brand team. But as someone who works there, it's going to be different.

[0:10:58] Sunny Manivannan: I love that the bar starts at hot mess. It doesn't get better than that. It's just that's the best it can be as a hot mess. Then it goes all the way, time, to dumpster fire.

[0:11:06] Ali Jawin: Yeah. It's not. If you don't think it is, when you're in your honeymoon phase, fantastic, or it's not affecting you, great. Never leave. However, have yet to find one, have yet to meet someone. There's just, because again, we're humans, we're imperfect. We're irrational. I guess, another one would be, I had a direct report a couple of years ago asking, it feels like we're in high school. When will we not be in high school anymore? It was because of things that marketing often owns, which I'm like, please don't make me own this, is swag. People get the weirdest feelings and opinions about swag. Every time HR owns it, I'm so happy. I'm like, “Please. I don't give an F about the socks,” or like, “Please, take this off my plate.”

I remember her asking everyone, and it was actually about socks this time, she was like, “This is socks. When are we going to be leaving high school?” I'm like, “Never. We're all humans. We do our best to put on our grown-up pants every day. At the end, we're irrational, and sometimes we get fixated on weird things. I don't know what to tell you.” Do you think it happens a little bit more in marketing than in other departments? Actually, when I was interviewing at Pontera, I remember one of the management teams saying “How do you handle when marketing gets bad ideas?” Because I do know that marketing, everyone thinks they're a marketer. Everyone has suggestions.

I remember looking at the CFO, I'm like, “That's entirely true because I don't think anyone's going to the CFO saying that I think you should do this accounting strategy.” It was almost like, people think that there are accounting strategies. I'm so thrilled. Everyone comes to marketing with their ideas. Just to realize that it is, what does this say? It's always coming from a good place. It might not always be coming from a good place, but just sort of, you know what? We're humans and we just – it's just easier to roll with it.

[0:13:12] Sunny Manivannan: I love the idea. I mean, first of all, I'll just say one thing, which is that in every podcast episode, we try to get a couple of clips that are short clips that we can post on social media and so on just to bring people into the full episode. We were 13 minutes into the recording and there's already a half a dozen clips that I so desperately want to post on social media. Thank you for just being a fountain of wisdom and really memorable wisdom at that, which is not easy to do. Thank you for that.

[0:13:38] Ali Jawin: The problem with me is that because also my husband is in sales, we're a constant sales and marketing. I don't say like a quote. It's actually a lot better. It was really bad when he was selling to marketers, because be at 6 am. He's like, “So, tell me about funnel conversions.” Now, he sells to engineers and it's a lot better.

[0:13:56] Sunny Manivannan: You're dealing with sales your entire life and he's dealing with marketing his entire life.

[0:14:00] Ali Jawin: Yeah. Actually, he was an outreach customer as well. I think one of the low points in our marriage is when we were sending out MPS emails. Even this subject line said something like, “Ali Jawin asked me to do MPS.” He didn't even open the email. Didn't even open it.

[0:14:19] Sunny Manivannan: That's incredible.

[0:14:20] Ali Jawin: Yeah. I actually hear him laughing in the background.

[0:14:23] Sunny Manivannan: That's incredible. You obviously know the data, because if you're sending it and you say, “Yeah, we know who opened this or not.”

[0:14:30] Ali Jawin: He showed it to me on his phone even first. Then took a screenshot and sent it to my customer marketer to be like, “Just so you know, the response rate wasn't like what you were hoping it was. At least I have one data point of why and I'm sorry.”

[0:14:43] Sunny Manivannan: That's amazing. Okay. I want to talk to you about these bad ideas. What do you do with these bad ideas? Because clearly, every CMO has to have a coping mechanism for these bad ideas. How do you deal with this?

[0:14:57] Ali Jawin: There are a few ways. One is that my motto is data, not drama. I always have a reporting system in place. It's the first thing I do when I come into a new role is seeing what analytics or dashboards are like. Because, first of all, my philosophy is data, not drama, you need to have data. One, I find that if you don't know what's working, if you don't know what's moving the needle or not, then you don't know how to spend your time. I think that's the hardest thing with marketing. You can do any. There's so many things to do. But if you don't know it's actually contributing to revenue, or building your brand, or whatever metric it is that you're pursuing, it's really easy to waste your time in random acts of marketing. You get really talented people doing things that just don't really add up to much.

One is I like to put in a reporting system so that you can be like, okay, this is working. This is not. That way, everything that everyone is doing is actually contributing, is actually moving the needle. One way that can really help is that when people come up with an idea, even if it's sometimes a good idea, or we just don't know, we point to our dashboard and be like, “Listen, that's a great idea. However, it will cost X. It'll take this long. To make this work, we probably need to stop one of these things. Which one would you like us to stop in order to do this?” That ends a lot of conversations right there. Because especially, and this definitely requires marketing to communicate what they're doing and what's working.

Marketing should always be presenting at town halls and presenting at least monthly, here the campaigns we’re running, here's what they're doing. For example, one company I was at, LinkedIn ads was just a gold mine for us. Yes, it was expensive. We just knew if we put this much in, we would get this much out. When we would get ideas for other things, it's like, okay, we could do that. We have to take out the LinkedIn ad budget or take part of it out and we’d be like, “No. Please, don't touch that. I need that. That's where my demo request comes in.” That does a lot of it.

I would also say that there are sometimes ideas that I don't always personally think are a great idea. But if I trust the people, I will say, go ahead and let's see. Sometimes I'm right. Sometimes I'm wrong. One time I was wrong, I remember it was at the RepTrak company. My content and SEO team was like, “We should make ultimate guides.” They showed me the SEO rationale behind it. I was like, "I mean, sure, you can try. I was like, the ultimate guide to reputation, that sounds really boring." It was a hit. I mean, yes, I also did a fantastic job with it. It was based on the Joan Jett song, 'I don't give a damn about my bad reputation.' It was all very punk rock. They did it really well. It was one of those times where it was really good for me to actually be like, you know what? I don't know, but let's try and let's test.

I was like, so, yeah. One thing is if you don't know, go small, because that way, if it doesn't pan out, it's not huge. There are also times where it's just like, you know what? That's really great. Let me come back and think about it. A bunch of those have been every time and this happens at every company, let's go buy a list. I'm like, yeah, I'm going to go look into pricing. I'm not going to look into pricing. I'm not going to do that. Also, I'd say a lot, there's so many ideas that are just brain farts that get sent to marketing, that people forget about.

I learned this earlier in my career that sometimes the best thing you can do is ignore an idea and just wait to see if it comes back. Does the CEO – does someone really care about this? Or is this literally a brain fart, where they sent it off and they never think about it again? There was this one time in my career where a general manager wanted us to create this game. I'm not a game expert. He's not a game expert. We spent two months. It didn't make any sense. None of our customers could figure it out. If I had just left it, it would have been fine. I maybe didn't want to say it. I saw them call the dumb ideas folder, where if they're ideas where I'm just like, this is a terrible idea and I also don't think it's ever going to come up again, I just think someone's like, "Let me set –", and I just put it into the folder.

Because if they care enough about it, they will follow up again and they will ask. Then I have it. It's like, “Oh, I'm so sorry. Got lost in the inbox,” and you can deal with it then. More often than not, never hear about it again. I'd say, much more frequently than the bad ideas are, again, it’s just they're good ideas. We just don't have the budget. We don't have the time. I think that's one of the things that's hardest about marketing is that the amount of work that goes into the end product is not visible. People are like, just throw together a webinar. Just the landing page alone takes a lot of time. You have to do all the campaigns. You have to create the content. You have the rehearsals. You have the emails. There's so much more work than goes into it than people realize.

I think the hardest thing is just being like, listen, it's not a bad idea, but which of these things that we're already doing, do you want us to stop? Again, that's why I think you need to have those attribution platforms so that you can prove what you're doing is working, or not working, and then you switch. If you don't have a source of truth, then you're really vulnerable to those ideas.

[0:20:34] Sunny Manivannan: I love the idea of a dumb ideas folder. Dumb doesn't necessarily just mean bad, right? It just hasn't been thought through at a level that would warrant the weight of an entire team.

[0:20:45] Ali Jawin: Yeah. I mean, with billboards. Here's the thing. Not saying that they're not effective. They absolutely can be. Everyone thinks, like I don't know why people don't realize how expensive they are. They're super expensive. It's always like, sure, you're going to, if you give me another $300,000, absolutely. No more budget. Okay, then no billboard. Let's move on.

[0:21:06] Sunny Manivannan: Totally. Love that. Yeah, I mean, I'm not a game developer either, but that doesn't seem like a weekend project in marketing.

[0:21:14] Ali Jawin: Oh, yeah. You want to spend all this money and not really be able to track it? Great. As long as you're okay with us never being able to fully understand the ROI, we can go for that. There have been companies where that has been the case. I think there are some boards and some CEOs that are a little bit more willing to – it's like PR. It's really hard to evaluate the ROI of PR. Thankfully, most of the companies I've worked out have just understood that metrics are going to be a little bit fluffier, but have understood that it's important.

Whereas, other companies have just been like, “You know what? If we can't track it, we don't want to do it.” As long as everyone's clear, then it's fine. But it's like, well, why don't we have any PR? Well, we don't spend anything on it. That's where those conversations come into play.

[0:22:01] Sunny Manivannan: You mentioned a couple of times a few mentors in your career that have given you great advice, or have supported you during not the easiest times. Tell me a little bit about what role mentors have played in your career. How did you build these relationships? Because I often get questions from people asking about, “Oh, can I introduce them to somebody that may want to be a mentor? Do I want to do that myself?” How do you do it? How should people do it these days?

[0:22:26] Ali Jawin: My personal life, professional life has been shaped by mentors. I've been really lucky and fortunate. But I'd say, and this is going to sound a little stranger than it is, but it's also true. Generally, I make them my friends, which is good, because otherwise, I become a stalker and that's a problem. I think I look at the first CRO at Yesware, and it was my first day in a professional job, and aside from the PhD, and I remember meeting her and being like, I just want to be her. I mean, she's in sales, I'm in marketing, and I don't know how to do that, except maybe by osmosis. When they were looking for someone to work really closely with the sales team, I raised my hand, because I figured, if I was just next to her enough, her influence would rub off on me. Took every opportunity I could to work with her.

Then when she left the company, and I was based in Boston, and she was in San Francisco, or in the Bay Area, every time I was out there, I would reach out to her. I would take the train an hour and a half to where she lived. I think that way with a lot of the mentors that I formed. I just, I put in the work. I will schlep to where they are. I will go to their events. I think it's a lot of putting in the time and effort and showing that you're invested in them.

Also, it's very much, I think paying it forward. Helping them with things. If they need advice, if they need quotes. I think it's something that develops. When people have asked me, it's an organic relationship, I would say. People asked, it just feels so awkward like, “Will you mentor me?” I'm sure there can be situations where it's appropriate, but I think for especially a lot of the people who are getting asked those questions, they probably have a lot of other people asking those questions, as opposed to someone being like, “Hey, I'm in your area. Can I take you out for lunch?” Or showing up to their events.

So many of my mentors have really just been people who I just – I was there where they were. I schlep to the conferences, I schlep to the networking meetings, and just, there's nothing to replace that FaceTime. I think if there's someone with that relationship, it's introducing yourself, putting in that effort, being where they are. Again, you don't want to be a stalker. That gets creepy. But if you put in that time and effort, almost generally, a real relationship forms.

[0:24:57] Sunny Manivannan: There's a big space between stalker and just, "Hey, I'm interested in you. Let's see if there's a connection here. You can certainly help me, and if that's something you're interested in, then let's actually build this relationship."

[0:25:09] Ali Jawin: Sometimes it takes years. One of my, I'd say, more recent mentors, I don't think she knew I existed for years, and we had spoken. I think it was a four-year, until we actually became real friends, and she's incredibly important to me, and I really value our friendship and relationship. Yeah, it was a solid three to four years before she had any idea I existed. It's the long game, I would say, with these relationships. I don't think you can expect to go to an exec and just be like, “Tell me everything I need to know right now.” I think you have to put in that effort first.

[0:25:46] Sunny Manivannan: Love that. Let's go back to marketing for a second. There's so much that's been said about marketing, and clearly, people who have ideas, the minute they think of them, they still send it to the marketers. Everybody's thinking about marketing in one-way shape or form. You are a rare expert in marketing, just given everything you've done and the circumstances in which you've had to do them, not always the easiest. What do you think is the most underrated skill in marketing?

[0:26:12] Ali Jawin:  Mostly, phrasing this as either a lack of fear or a willingness to keep on experimenting and pushing. Because marketing is changing so quickly. I can't remember who said this and it's unfortunate because it's a really great quote, so I don't want to take it for my own. But this was back, I want to say, 2016. Someone really smart said that there are going to be two kinds of marketing jobs in the future. Ones where the machines are telling you what to do, and ones where you're telling the machines what to do. One where they're telling you what to do and one where you're telling them what to do. Guess which one is going to pay better?

That was before AI. But even then, when attribution platforms were coming, marketing has just become so technologically focused. It's become so much about automation, operations, and reporting. I mean, listen to brand and creative and storytelling. Your business isn't going to be successful without those. Marketing is so much more than that now. If you want to do the creative, the brand, the storytelling, if you don't have those business metrics, you're not going to get to do that other critical thing.

I think the ability to realize that what you did last year might not cut it this year. That you have to keep, being willing to reinvent yourself and reinvent the way that you do things. I almost feel like, I've seen a few iterations in my career already. I think when I started there wasn't that – it's not that there wasn't great reporting, but it was really hard to show marketing's influence on revenue. It's not perfect yet, but it has come so far. I know attribution can be a dirty word in marketing circles, and there are companies looking at it differently. But if you don't have some form of it, you're blind and you're not being able to show you're effective.

Then I felt like, the ABM platforms came along, 6Sense demand-based, what engage you. That was a real difference. Now, suddenly, marketers had to think about ABM and more orchestration, and personalization at scale, which became a lot more technical. Now we're at the AI moment, and I don't think we're at the point quite yet, but I do think there's going to be a moment in the not-too-distant future, probably a couple of years where we might see the first of the marketing team reductions because AI can take it over.

Now, people who are embracing AI, they're going to be more in demand than ever. Just because you have AI, it doesn't mean you don't need content people. You absolutely still need content people. You absolutely still need creatives. But creatives can be so much more effective with AI. I think the big thing is you just need to be able to keep on willing that, I don't know if there's any profession where you shouldn't keep on learning. I think, even in accounting, there are probably new strategies and new software. Sales, while it's different, there's new technology, I think it'll always be very human relationships, negotiation. Those skills might not change fundamentally. I think to be successful in marketing, just where we are today and where we're going, you need to constantly be willing to reevaluate how you do things and to learn new skills, because I don't think it's going to be slowing down anytime soon.

Who knows what we'll be talking about in 10 years? But I think gen AI is going to really just transform things and that will have implications we don't even know. Marketers really just need to be ready to be a few steps ahead of that, or just to embrace it as it comes. Change is uncomfortable, change is scary, but thankfully, most of these things were made for marketers. They know we're not engineers.

[0:30:03] Sunny Manivannan: Totally. It's incredible. Yeah, there's so much that's changing right in front of our eyes.

[0:30:08] Ali Jawin: I mean, I'm not a designer. I have no design skills. However, I can go into ChatGPT and even just before we started talking, I'm making an intro deck about me. It was like, make Ali-isms and make it fun and creative. I was like, oh, wait, that was way too fun and creative. Make it more clean and sophisticated. I can barely draw a stick figure. Yet, because of this, I now have these beautiful slides.

[0:30:37] Sunny Manivannan: What's really interesting about, even the example that you just mentioned is that you're actually using your imagination even more and you have the time and space to do that because the output and the feedback is right in front of you very quickly.

[0:30:48] Ali Jawin: Yeah. Also, I was just throwing it in, not that anyone asked what my favorite AI use case is the one that's probably saved me the most – it's not, I would say, the most advanced. It’s definitely not the most advanced. This has now been true at three companies, so it's not. But you know, sometimes when you get emails that just really erk you, they're not even that important, but just like, ugh. Before ChatGPT, crafting a response that responded but wasn't too passive-aggressive, that indicated you weren't – Just not only the effort of writing it, but just the emotional, being so annoyed, now it's going to ChatGPT and I'm like, “Say no politely.” Not only have I saved time, but just the anxiety, or the annoyance I like to do in the first place having that removed, and this works in your personal life as well. Yeah, probably the most profound thing I've shared on this entire conversation.

[0:31:49] Sunny Manivannan: It is certainly profound. Very, very interesting. Well, it's really interesting, I mean, because you brought up something that I think so many people just accept as a fact of life, which is all of the time that we spend dealing with certain unpleasant things and the emotions that arise from that, now you can just delegate the response and the action to something that is completely dispassionate.

[0:32:18] Ali Jawin: Yeah. Another great use case was actually, this was when I was negotiating my outreach contract. I can advocate for my team, but it turns out I'm really bad at advocating for myself, but ChatGPT wasn't. I put in the points that I wanted to negotiate and ChatGPT said such like, and I got all of those points across. But there are just times where it can be really hard for us for our own hang-ups, for what's ever in our head. They're going to always be careful with ChatGPT, can hallucinate. You never want to put in proprietary, or personal information, like all the appropriate disclaimers. But if you want to counter an offer and give an example why, it can do all these things without your hang-ups.

[0:33:03] Sunny Manivannan: Totally. Very interesting that we're – I think still at the very beginning of this revolution in how just people work, what do you think is going to change in marketing? Do certain things become more important in the world of AI?

[0:33:17] Ali Jawin: Yeah. I mean, I actually think if anything, it's going to show how important good content is. Because even before Gen AI came along, I guess, one of my big gripes is B2B content is that I find a lot of it isn't very good. It's either very fluffy, telling me things I already know, or just so obviously selling your solution. And/or, because sometimes it can be both incredibly boring and dull. If I want to be bored, I'll go do my taxes. Or, there are a lot of hard things I can, and I can try and learn about health insurance. There are plenty of hard things I can do in my day to day that I don't really feel doing it. Reading B2B content from a vendor, definitely not what I'm going to do.

Whereas, I think where the content teams that I've led, especially in the past couple of years, the reasons why they've been successful is that we've come up with what we call the "strawberry smoothie strategy." I did not coin this. It's by a woman named Lex Juan, so can't take full credit. Her thought was that content, you wanted to have that medium. You don't want it to be like, imagine you've just gone to the gym and you've worked out. You don't want to get an ice cream sundae necessarily, because you were just healthy. You don't want to throw that all down the drain. But no one likes green juice. Nobody likes celery juice. Instead, what you want is that strawberry smoothie. It's delicious. It's sweet. You've got your calcium. You've got your fruit. You've got your protein powder. It's also good for you, but it's enjoyable. That's what I think really great B2B content does. It both teaches you something new, but it excites the brain. It's the ultimate coffee. You enjoy reading it. That is hard for humans to do. I have yet to see ChatGPT do that.

I think we are going to be inundated with even more mediocre, like flat content. I think this is where we're going to see real content shine. I think if anything, human content writers, the ideas behind it are going to be more valuable than ever, and that you're really going to see it. It's not that I don't think AI is important in content creation. What I absolutely love AI for when it comes to content is creating derivative content. Take this first few pages of this eBook and create a blog post out of it. I think the derivative content it can create is really very good, and so that's where people can be more predictive.

I also think it's going to be very interesting, and this is what I don't know, to see how agents or AI agents factor in. First of all, just by even talking about AI agents, I may have made this episode dated within three months because just because everyone's talking about agents now, no one was talking about agents last year. This could be one of those real fads. I don't know. It'll be interesting. I think that the role of RevOps, marketing ops, as we add more and more of this technology, it's certainly going to become even more strategic. For the past couple of roles, my RevOps person has been my right hand, because they know how everything fits together.

Yeah, I'm certainly not ready to – marketing has used automation for a decade now. That's not new. I'll be very curious to see how that evolves because I'm not exactly sure of the use case. We're seeing a lot of AI BDRs, and automating early parts of the sales cycle. I can see that. I think that makes a lot of sense. It'll be very curious to see how much of marketing automation we're really willing to entrust with AI. If we are willing to entrust a lot, what are the skill sets to oversee that? Yes, RevOps and marketing ops are in some ways well poised, but could also be very different. I think it'll be interesting to see. That's where I don't know. Yeah. Someone would be like, "Oh, put an AI agent in charge of this marketing thing." I'm not ready for that quite yet.

[0:37:22] Sunny Manivannan: It's very interesting, because everything you said about agents, you’re right, it could be dated in three to six months, because nobody was talking about the stuff. I think what people might be excited about, and certainly, I'm excited about this, is the idea that you can now do things that there's no way you would have hired a headcount for it before, hired an agency for it before, because it would have been too prohibitively expensive. I think those use cases are going to come out more and more. Naturally, we're all thinking about the current things that we are doing and can AI replace this, but I think the much bigger opportunity is, okay, what does the marketing team of the future look like? What is the scope of your impact on the company, on your sales team, on the market at large, and what can you do with a team of four, and that you couldn't do with a team of 40?

[0:38:11] Ali Jawin: I think that's where it's really going to change. I think both, perhaps more applicable to sales, but also impact marketing, is that's the way I've been describing is like, let's say you're looking for, you want to celebrate a big milestone, and you want to find a really exclusive, hidden away, tropical island to visit. You're probably not going to want an AI agent for that. You're going to want to talk to someone you trust or do a lot of research, or whatnot. Once you found the place, you're going to want the AI agent to book it. You don't want to call someone for that transactional aspect of the transactional stuff. You just want to do quickly.

For the things that are still qualitative, that there's no discernment, judgment, taste. I think that's where the human elements are really going to still be important. But I think the marketing teams of the future are going to look very different to the ones of the past. I think the sooner people stop fearing that AI is going to take their jobs and instead, start seeing AI as – by using AI and becoming adept with it, you're protecting your job. If for no other reason, then one of my creatives has said is, at least when every holiday party, when Granny and Uncle Richard are asking, “Well, I have a job in the future.” No, I have an answer for them this time.

I was actually at one of my creative’s birthday parties a few years ago, and her dad pulled my husband over to be like, “Is she going to have a job? Is AI going to take her job?” It was like, "No. It's absolutely not. It's going to make her more – " but that's the level at where we are. That was a few years ago.

[0:39:47] Sunny Manivannan: Totally. It's funny, I'll share a rare story from my side because this is so relevant to my world as the founder of Peerbound, we have sold AI customer content software, and we're saying, “Hey, you can do things now that you can never do before.” There have now been multiple sales calls where somebody upfront will just say, “Sunny, can't wait to have you tell me how this is going to take my job.” They're joking, but they're not joking, and they're asking for a real response from me, which I usually give, and I say, “Well, the typewriter didn't take your job, and the personal computer didn't take your job, and the Internet didn't take your job. Look at the things that you're able to produce now, and imagine where you would be without those technologies. None of us would be employable.”

If we came in and we said, okay, here's my quill and ink, and I'm going to show up to this company that's using all this technology, and I'm going to try to be productive, there's just no way. Then I walked through, okay, here's all the things that you can do now with AI. One of the use cases that I love is, hey, you can actually go send really relevant content to every member of your sales team for every opportunity. There's no way you would hire a headcount for that, but it's extremely valuable.

[0:40:56] Ali Jawin: Yeah. I think one of the things I've learned as I guided teams more into AI is that we need, and to be fair, I did not appreciate this at first, so I was really glad that my team was comfortable enough to share this, is that doing something new takes more time, and you're going to make mistakes. If you're expecting your team, or even if it's just for yourself, to implement this, you need to, well, one, if you're a leader, you need to give your people the time to do it, and the grace to know, because when I was asking my – I think it was – I can't remember if it’s creative or content. I guess, it doesn't matter. But I'll say, creatives. Like, hey, I got you this AI training. Why aren't you using it? We had this big deadline. I know it would be faster eventually, but I still have to learn it and get familiar, and it's going to take longer, and I need to get this done by this point. I was just so glad that he had brought this up.

Because when he did, I was like, okay, well, that is a physical event, so we can't push that deadline, so we're going to get through this. But then after this, I'm – let's plan an additional sprint for it to give them that time. Because if we don't do it, they're never going to adopt, because it's hard to learn something new. First of all, emotionally, you have to be in a good place for it. It's an uncomfortable feeling. I think, as leaders, one, we don't recognize that that's hard, that it's a little bit scary to do some of the pan-holding. It's okay to make mistakes. That this is how we're going to learn. But also, it's just going to take time. People will speed up.

You have to slow down to speed up to learn the new skill, and that if we're not giving that to people, and again, for individual contributors out there, or people who are being pressured to AI and feeling this, bring this up to your leaders as well, that you want to do this, but that you just need a little bit more time. It's a new skill that always takes more time. You will be faster, but you just need some time to get up to speed.

[0:42:52] Sunny Manivannan: I think 2024 was certainly the year where I think all the executives got excited about AI, and every CEO basically planned for a future where AI is already extremely productive, and it's coexisting with all the people that are already working on these teams, and there's just no way that was going to happen in the space of less than a year. 2024 was the year of that clash between the executives, and then the people actually doing the work who are looking at all these AI solutions saying, “Well, this can get me there, but it doesn't get me the whole way there.” But they expect something to get the whole way there, and I need to go manage that, and we need to come to some agreement, and I feel like 2025, you're going to start to see some real progress.

[0:43:31] Ali Jawin: It's going to be published sometime in January, but it was quoted in an article about some of my predictions for 2025, and one of them was around AI, and it was both some marketing. I'm like, this is the year that marketers will actually embrace AI. That last year was exactly as you said, executives getting really, really excited. But especially in the earlier part of the year, a lot of the platforms just weren't there yet. Or they were still hard to use, or security teams were like, absolutely not, or IT. Whereas, one, I think the platforms themselves have gotten a lot better. There's definitely this consolidation in the market.

I feel like this year it goes from being the buzzword to actually something that people are really going to start using, or that now it's not – again, agents, this is a fad or not. At this point, AI, not a fad. I think this time, this is going to be the year. Again, I think it won't be Jan 1 hits, and suddenly, everyone's diving in. But I think it's definitely, I think this year will be the turning point where it really is incorporated into the day-to-day lives.

[0:44:36] Sunny Manivannan: That's right. Yeah, from our very, very small perch in this world, we're certainly seeing that be the case where people are not budgeting for this in 2025. They saw our demo in 2024. They're like, “This is cool. We think this will work for us. But we don't have the budget for this right now. We're going to budget for this in 2025.” It is part of the AI budget, it's part of the marketing budget. There's not so many pools of money that you can pull from. I'm not saying the budget started loose by any means in software marketing. We haven't gone back to the 2020 era just yet, but I think there's definitely a lot of appetite for "let's use technology to be more effective, certainly more efficient, but also much more effective than we were before."

[0:45:15] Ali Jawin: Yeah. I don't know if we’re at a point. I know people say this. I don't know, and this is my hot take. People will say, we're just going to spend on AI. At least to me, that's still a mistake. I think you should always spend on the technology that's going to solve your problem the most, that – I don't believe in AI for the sake of AI, and that is a hill I'm willing to die on. But it does seem that a lot of the things that are actually going to be – a lot of problems that can be solved can be solved by AI. But I don't love, and this is again, a personal gripe, I don't love AI washing. If you have a great product and it solves a key problem and it doesn't use AI, I feel marketers are still being pressured to say it involves AI. I don't know. Maybe that's just me, but I'm still just a big believer like that, listen, if you solve my problem with AI, that's amazing, but at the end of the day, I need my problem solved, and it could be – the Keebler elves doing it for all I care. However, it gets done cost-effectively, quickly, if it's a Keebler versus AI, if the Keebler elves do it better and it's cheaper, I'm going to go with that.

[0:46:26] Sunny Manivannan: It's very interesting that you said that, because we've always on our side had a tough time, and we still have a tough time figuring out how much should we talk about AI, because our product only exists because of AI, and what's possible with AI. Every vendor in our space and frankly, every space has AI washed, they put the code of AI paint on what used to be a fairly old car that was showing signs of rust, and they're like, “Well, this is now AI-powered, blah, blah, blah, blah, blah.” Then now, buyers all of a sudden just got exhausted by hearing this.

We basically spend more time educating and it's not as exciting as AI is going to do this for you, but we say, well, here's how we use AI, and here's why that you can't do this without using AI this way, and why the work is not trivial. It's not just a ChatGPT API call, which is what everybody was expecting last year. Those demos were cool, but very quickly, you're like, okay, there's just not that much business value to that, and there's some more work that I have to do. It's a very interesting time as a marketer, think about how do you even talk about AI.

[0:47:28] Ali Jawin: My two ways, again, it's a very, I like to be quantitative and sometimes as qualitative, but the two things I like to do is look at – do keyword research and intent data. Because what people type into Google and what they're searching, especially when it's anonymous, that's where they don't lie. It's been interesting. There are certain times where AI search words are everywhere. But more often than not, they’re not. People aren't searching AI solution. They're still searching for the solution for their problem. Same for intent data. That tends to be where all look, because if there is a lot of AI in that data, okay, then it might make sense to talk about it a lot. But if you're a product that wasn't “born in AI,” and people aren't searching for you for AI, it's not that you shouldn't talk about it, but yeah. I know, it can be controversial, but yeah, at the end of the day, I still think people care.

Again, if you are, if you can't exist without AI, then you need to talk about that. I think it's very interesting how people who are actually buying the technology, versus maybe how a CEO, they're going to talk and think about AI very differently. At the end of the day, you need to market to the person whose problem you're solving.

[0:48:46] Sunny Manivannan: Yes, love that. I want to talk to you a little bit about, given that this is The Peerbound Podcast we believe heavily in peer influences. I want to ask you about some of your peer influences, and I also want to ask you about some things that are in your life that you really love, and perhaps, you can recommend other folks. I'll start by asking you about who are your favorite SaaS marketers, marketing leaders, who are your peer influences?

[0:49:11] Ali Jawin: For me, Latané Conant, the CRO at 6Sense. I think I mentioned her earlier. I like to say that she's the patron saint of marketing, and we just worship at her altar. I absolutely love her book, No Forms. No Spam. No Cold Calls. Yeah, she's at 6Sense, and it talks about 6Sense, but I think aside from the technology, which I'm a big fan of, it talks about a way of marketing that is how to personalization at scale before Gen AI was even there, and she's just so smart about how she thinks about it.

I'm always pushing the envelope of their conversational email product is generating 25% of their pipeline already. Yeah, just always a big fan there. I love Carilu Dietrich. She was the CMO that took Atlassian public. She has a newsletter called Hyper Growth. I save all of them. Once a month, I also do a Deepak dive, super smart. Then when it comes to AI, I follow Nicole Leffler and Liza Adams. Again, super smart, and they break it down for marketing use cases. I'd say, those are probably my biggest marketing influences. I'm also a big reader of, I mean, I'll read a business book here and there, but I actually just like to read fiction and nonfiction.

It's very easy, I think, in marketing, especially B2B marketing, just go down a rabbit hole and just get sucked into the LinkedIn universe. Not that you shouldn't be there. You're going to learn a lot. One book I just finished, I think it was The Wide Wide Ocean or, it was The New York Times at Top 10 Books. It was about Captain Cook and his final disastrous trip around the world. Of course, it had nothing to do with B2B marketing, which was the point. What I loved about it was just learning about history and leadership and clashes of different cultures. I just think the more influences we surround ourselves with, the more creativity we come to lead.

Now, you think for all of the 80% of time that you put into your career, always have that 20% for reading, for art, for theater, different ways just to open up a different part, get your brain working in a different way.

[0:51:29] Sunny Manivannan: Love that. I mean, there's so many good influences and books and I love the idea, or your thought about don't just read what you see on LinkedIn. Because I think we all think we learn more from these bite-sized things than we actually do because it's hard to put this stuff into practice. And you feel smarter because they're also going to copywriting now and so on. They're going to make you feel like, they’re out of value, but you're not really improving. Then really expanding your mind and going to read something from history or fiction, great, great recommendations. Wonderful.

Well, listen, Ali, I can't thank you enough for joining me on The Peerbound Podcast. You are such a superstar, and so insightful on so many topics, and so memorable with your insights. Really a privilege to have you on. Thank you so much.

[0:52:18] Ali Jawin: This was great. Thank you as well.