A Marketing Leaders Guide to Approaching the Future of Ai
Marketing leaders can prepare for AI by making learning collective, documenting experiments, hiring for curiosity and judgment, and creating a safe path through real uncertainty.
Get the next practical AI marketing episode wherever you listen.
Make AI Learning a Team Practice
Marketing leaders do not need to know every new AI tool before their team does. They do need to create an environment where learning is visible, useful, and connected to the work the team is already trying to improve.
The risk is treating AI as the private hobby of one enthusiastic person. That person may discover valuable uses, but the rest of the team does not build shared confidence or learn how to apply the ideas. A stronger approach is to ask: where are we now, what are we testing, what did we learn, and how does this help customers or the organization?
Begin With Small, Documented Experiments
Smaller teams can often test quickly because fewer approvals are required. That is useful, but speed without memory creates duplicate work. Document each experiment: the problem, the tool or workflow tested, the input, the result, and what to try next.
This lets a team revisit an earlier test as the technology improves without relying on someone’s memory. It also makes experimentation safer. A one-month trial of a video or research tool feels less threatening than an open-ended mandate to change everyone’s work at once.
The goal is not to chase every release. It is to build an evidence base for the work that matters to your team.
Hire for Curiosity and Practical Skill
AI may change how specialized some roles need to be, but it does not remove the need for strong marketing judgment. A designer who understands brand and emotional connection still brings something a fast image generator cannot decide. A strategist still needs to know whether a message fits the audience.
What changes is the profile of a strong teammate. Look for people who can explain how they use AI, who are curious about new workflows, and who can show their thinking. Contractors can be a useful way to test both a person’s skills and a developing type of work before committing to a permanent role.
Do not hire someone merely because they mention AI. Ask how they used it to improve a real outcome and how they checked the result.
Lower Fear Without Pretending Nothing Will Change
People have good reasons to feel uncertain about AI. Leaders should not dismiss that fear or promise that every role will remain exactly the same. Instead, make the opportunity concrete: learning these tools can increase the scope of work a person can handle, help them contribute to future decisions, and open new paths in their career.
Frame early work as a chance to be a beginner. Celebrate thoughtful experiments, including the ones that do not work. Encourage people to ask questions and share what they learn. A growth mindset becomes especially important when the team cannot see the entire map ahead.
Use AI as a Thought Partner Too
AI can support leaders beyond execution. It can help stress-test a proposal, identify gaps in a plan, or offer another angle on a strategy. That does not replace an honest human conversation, but it gives a leader a low-friction place to explore an unfinished idea.
Over the next stage, teams can improve their execution work while watching for the next opportunity: AI that helps information and intelligence move across functions. The leaders who prepare now will have a team ready to evaluate that change together.
In this episode of the AI-Driven Marketer, Dan Sanchez talks to Courtney Baker, CMO at Knownwell, in a dynamic discussion about leading marketing teams in the age of AI. They delve into how AI is reshaping marketing roles, strategies, and team dynamics. From experimenting with AI in small teams to preparing larger teams for AI integration, they cover the multifaceted impact of AI on marketing leadership. Listen as they explore practical ways AI can enhance marketing strategies and team productivity, reflecting on the evolving landscape of AI in marketing.
Links Mentioned:
- Knownwell's website (https://knownwell.com)
- Knownwell's AI Know How podcast (https://knownwell.com/podcast/)
- Courtney Baker's LinkedIn profile (https://www.linkedin.com/in/courtney-baker-0b569b33/)
- Knownwell's beta waitlist. For those interested in their intelligent enterprise operating system (https://knownwell.com/join-the-knownwell-cq-waitlist/)
- Knownwell's free assessment tool (https://knownwell.com/assessment)
Episode Timestamps:
00:42 - Courtney's perspective on AI's influence in her marketing role.
02:45 - Training and leveling up marketing teams in AI.
04:01 - The agility of small teams in adopting AI technologies.
05:58 - The concept of turning a small team into a powerhouse with AI.
07:11 - Recruiting talent in the age of AI.
09:15 - Fostering a learning mindset and embracing AI in marketing.
13:03 - Utilizing AI as a strategic tool in marketing operations.
19:22 - Encouraging a growth mindset in teams facing AI integration.
22:33 - The future of AI in operational and strategic roles in marketing.
27:12 - AI as a co-thinking partner in strategy formulation.
30:18 - Focusing areas for marketing leaders in the next six months.
33:27 - Courtney Baker's insights on Knownwell and AI in client retention.
welcome back to the AI microskills podcast where we're trying to educate marketers on how to leverage AI to do more and do better because the future is AI and I'm excited to down to talk to Courtney Baker who is the CMO at known well about how to lead teams in this coming age of AI because as things change a lot of it's changing for our workers a lot of it's changing for all the different tactical silos of marketing from email and social and writing and soon video I was just playing with the video tool so as AI is changing all these things so how we lead our teams will be changing and Courtney I'm excited to talk to you thank you so much for coming on the show yeah thanks for having me I'm excited to be here
start a kick it off I have to ask like is AI becomes a bigger part of marketing how do you think it's redefining like your role as a marketing leader like we've had I feel like digital marketing is kind of been tried and true over the last 10 12 years and there's been a certain Rhythm for how to get leads in the digital realm with social and all that kind of stuff but how do you see that kind of Shifting now for your role as like a CMO in a market leader yeah that's a great question I would say for me you know it's an interesting place to be in because I've come out of an established business and an executive role and into a startup role and in some ways that gives me an advantage because I'm so much closer to the weeds
and I'm able to see okay how is AI actually affecting the day-to-day work the ins and outs of what's happening and I think especially if I put myself back in my previous role I think there has to be a real emphasis of training there's so many pockets of AI education within organizations even at the highest level you'll have you know a small group of people that are really excited about that I think that is the same in marketing teams now I think for me as I am leading a team I'm really examining where are we right now
where is our expertise what is our deployment of AI look like across the team and then I'm really thinking through how do we collectively level up our expertise as a marketing team you know what experiments can we do collectively that drives value for our customers and drives value for the organization and really engaging in that collectively versus what I think probably happens a lot of times you get that person that's excited about Ai and you just like send them after it and versus okay how do we do this together and learn about this so that we all level up and then I think it's a different mindset as a leader of asking
especially as you're getting the end result you know in a very curious way like hey how did AI play into this outcome you know how are we able to leverage it in you know whatever the thing is that we're creating as a marketing team and I think if nothing else that provides I I am excited about this technology and really want to know as the leader how you're utilizing it I am you know how do I just keep that conversation going and Forefront of our team because I do think it's I think as we move into 2024 the excitement of 2023 starts to fade and it's easy to just get back into this is how I used to get work done versus continually to like
what's the edge on you know how do I continue to examine my my productivity what I produce and how AI can inform that so we're kind of an interesting season where these everybody's talking about it but it's the people that I find actually taking action on are like these smaller teams solo preneurs and startups right because yeah well there's less less pain if something goes wrong right so it's interesting now you you left to a larger team an hour on a startup team do you feel like more freedom to go and try some AI things and experiment knowing that there's just less pressure to get it right
absolutely I love experimentation and probably would say that's probably something that's natural to me regardless but it does all the bureaucracy or just having to check that you know we've got the right regulation and I think those things are incredibly important I just don't have to do that right now because of the stage that were in and so we can move at lightning speed on testing a new thing and and I think one important thing for me as I have been testing at lightning speed is actually pause and make sure that we're tracking those tests so that as the technology evolves all so at lightning speed
that I'm not having to do the brain work of remembering that experiment I've already done you know it's just I've got it documented it's easy to run it again and see hey does is the technology at a place where it actually solves you know this thing that I was trying to solve already and and not having to redo that mental work but I totally agree I think you know these smaller teams are especially in the marketing realm able to deploy it a lot you know a lot faster rate and I think it's exciting to see the things that are that are coming out of those teams as it's kind of always been true with small teams being able to make make things but I'm like hey guys the thing like right now it's the opportunity for small teams to get ahead of big teams and
play eyes even better because it's I mean this is a phrase that I've seen for marketing my other Market tech companies have been saying this of like you know turn your team at 3 into a team of 30 and I'm like it's kind of true it is yeah and I would say go ahead I will say it's it's also if you're on a small team or in a startup right now you also don't have the burden of how is this going to restructure my team how is this going to affect the people on my team and I think certainly as a leader that weighs on you when you have a larger team that you know do your point if I can have a team of three people in it actually equals 30 if you have a team of 30
and you really need three you know that that's a big burden as a marketing leader to way through and figure out how to do that well which also can slow you down you know as you need to do the due diligence to walk that well how are you finding your approaching a team you are to start up your building things you have kind of like a team of contractors but as you guys grow you're going to have to start recruiting people onto your team so does that does this new AI thing kind of change how you look for talent now is that change how you looking at like building a team before you're like okay like you're probably like well I need my demand Jen person or my address and I need my just a graphic designer eventually and you my copywriter it was kind of like there was kind of known
what is the thing that we are you know creating that brings value to our hopefully our customer and thinking through is there a way I could already be doing this for us versus looking for a person to fill that role and so it may be just a slower onboarding but if I can't if I'm like hey I can't help us with that it's not there and if I need to hire right now I'm more likely to hire a contractors because again the technology is
so quickly and I'm more likely to hire contractors that can showcase how they're leveraging Ai and what they're doing so I'm curious about those things of hey how is it how are you using AI is it something that you're interested in because I also know if you know I love to hire people that have already been a contractor for us full-time that's my it's been my hiring cheat sheet for a mini a Year's and so I think it's important out of the gate to especially in this moment that learning mindset you know are they curious about what's happening in the marketing Railway you and I you know this is our first conversation we you know we
get giddy about talking about the things and that's what I'm looking for and people that are coming on the team is their excitement and we say all the time on my podcast and I know how podcast that we've got a lot of Executives with you know proverbial AI hammers just looking for something to hit and that's certainly not what we want to do but I do think there is that that energy and excitement that Curiosity mindset that I'm looking at is I'm you know considering bringing somebody on board smart hiring or having contractors to hiring because yes is there anything like test like a test run in a contract or a freelance thing something going on right that's like the ultimate test and then it works out or it doesn't then it's no hard feelings right exactly
smart and it's interesting essentially you're looking for probably the same rules but with an AI event towards AI because AI hasn't really started replacing anybody yet but it probably will we don't know when but like there's obviously mid Journeys come a long way but it's not replacing graph designers are illustrators yet but we're seeing the possibility work could I don't know it's like we're early on but how do you think it like might I don't know but I think you're it's interesting that you're finding people with the AI bet because it's probably they're probably going to lean towards be more futuristic and being maybe more productive like a person you're using AI well you're probably maybe now doing the work of what used to take
specialization you know like we're able to do a larger breath you know so rolls aren't quite as special as they are today or if it's just what you said where it's I can just do what two people could do previously I think it'll be interesting to see how that plays out yeah cuz I imagine even when I was a graphic designer like you can only design so many projects that one so then if you only have one designer in the company was getting bigger while that one designer would be maybe bottle neck right because you can only designed so many projects but with AI I mean I've it's
how long time since I've been a full-time designer but even with photoshop's AI tools that are currently available now being able to do autofill or being able to come up with the stock photo that was going to take you 3 hours to find on istock photos with a few different then maybe it's not perfect but in Photoshop you just circled apart you didn't want you say make it disappear and it's gone and it looks good for something that was just the background image you can now what I'm just looking at the work that I used to do it as a designer yeah and now what you used to take three hours because it just took a long time to find the perfect stock photo is now done and rights you know I will say that certainly been true in the startup phase some of it is things I wouldn't have even you know because at this stage
you are so capital-efficient I mean you are just watching every dollar at this stage and so they're certainly things that like I will do in canva and we've got a team account you like we can whip up things in Canada I don't know that it's like hurting anyone else it's because if I had to go to a designer I probably would just say we're not going to do that you know and so I'm utilizing AI to just you know produce those things or when I use clap dot app to create your Google shorts It's again not taking away from a video person I wouldn't have gone and gotten a video person to do that and so it's again your metaphor of three people becoming 30 and it's like
small pieces it's not like a full-time job it's just getting more from maybe things you wouldn't have been able to leverage previously is is probably a more accurate at this stage I would say where we are it's just I think are just our outputs going to get better and therefore the quality of everything we're doing is just going to get better and more right the graphic designs an easy one for me because there's a clear output of design pieces versus marketing a little bit more ambiguous but even then like your canva pieces are better but eventually when you have money to invest you will still hire a designer because they will be able to do more better write that if you doing canva now they're doing custom designs because they have ai tools and like illustrator
which they may have only been able to budget 2000 will make it will look like something that took 5 hours to make exactly because they spent the same 20 minutes on it but now the AI made it like bam it look good in 20 minutes yeah and so everybody's qualities just going to go up but we're probably still going to be hiring the same people for I totally agree and I certainly it's just where like you know I've ever had a designer that we're working with on our website and our ux and our branding things that I don't think you know AI can't tell you if this
and brand you know if it has the emotional connection that you want with your audience that's something AI in my opinion will never be able to do will never be able to tell you like is this a creative is this creative it doesn't understand that in the same way that we would and so I certainly think there's going to be a huge opportunity and need for designers I just don't think it's going to be in here's an example Dan I sent out an email today to our whole team which is now global by the way and I was giving them an update on the brand kind of changed that I had decided on and I was telling them hey sometimes it's hard to remember these
I'm a big believer in internal language becomes external language and I was telling them about a brain scientist it's kind of all of my PS I was just trying to make it fun and I was like I'm going to send them this hideous graphic that's like throwing away the old you know terms because we're more likely to remember it you know if it's something you know shocking and I was like me putting a shocking hideous graphic I you know I might have gone to a designer in my old days where I had you know a team reporting to me of designers and ask for that it would have been kind of a waste of their time but now I can do that and literally three seconds on my own with these tools and so I included it in the
immediately got you know this is hilarious thank you love this email and again it's just it makes even like our communication better by using these tools and you know some designer doesn't have to roll their eyes that they have to create some graphic for an executive turn around yeah yeah yeah designers are funny if you were back at a larger team knowing what you know about AI today because obviously you've joined are I start up you've been reading and watching a lot of things you have your own AI podcast for your talking to people about AI you've learned a lot over the last
if you could go back or maybe if you were back in your same role at the at a previous company how would you be preparing your team now based on what you know about Ai and where it's going yeah that's a great question I think one thing that I have always been a big believer in is mindset and how you approach change your ability for your brain to be flexible and understand your perceptions of things you know what things are basically all the files that we hold and so when we come to moments of change how we approach them and some of what
I can tell a lot about you and how you've approached Ai and your ability to have a mindset of learning and I think I probably would have double clicked even more into that specially now knowing how much fear would come from this that's not my natural disposition you know I'm much more like let's get in there let's get our hands let's figure out what this can do for us a much more likely to be like think of all the health benefits of what this might bring for Humanity and versus the fear side of it but a lot of times you're not I'm not leading people that are in that
you know built that same way and so that ability to really get a mindset ready for this type of transformation and I think keeping it in perspective that this is a huge transformation helps in leadership again cuz I think a lot of times you get to this this stage of leadership and you like the change you're excited about those types of things but that is in general not who you lead and so I would be preparing them for that I would also be preparing just maybe even a more robust ability to experiment what is that look like what does that ongoing Cadence how are we talking about that in our team meetings how do we just go ahead and install that into the very nature of our
it's funny when I first started leading people I'm probably a little weird in that I just love learning I hated school but I love learning and I always do I still am read a lot and this whole podcast is because I want to learn more about Ai and talk to people who are like pushing it and figuring things out and leading and exploring things but I noticed a lot of people aren't that way some people they kind of like what they know and they kind of like doing the not repetitive work but like they kind of like staying in their groove and doing the same thing yeah would you be encouraging those those people because this is a good amount of them and I love them because I'm like somebody just needs to show up and do excellent work and just do it right
that starts to become dangerous not just for the company but for that person's career in some places in the marketing team how would you be encouraging them I think that's a good what you just said is a little insight into it but I think framing this up one as an experiment and I think anytime you have somebody that's like hesitant to change if you can frame it in something that is short-term like Hey we're we're testing out this new video tool for the next month you know that kind of pulls down the barrier but I think anytime you can frame things in light of what it
is for them what it means for them and I think it does become harder in this situation where you've got a lot of people just afraid for their job and so I think some of it is how do we handle that fear and sometimes that fear is accurate and we don't actually know you know what marketing team make out we've already talked about you know we actually don't know we'll roll be as specialized will they take all that we don't know and so some of that is just like how do we take the fear level down a few notches and then how do we really reframe this for what's in it for them because they're actually is a lot of opportunity for anybody that's willing to say
yeah I am I am really interested in this I want to learn more about it and I mean I just said earlier on this podcast I'm looking for people who are interested about AI that's the type of people I want to be bringing on to my team and so we can reframe this is actually a really great opportunity for your role and and I would say that is probably true for just about any employee that AI is a great opportunity for them and so if they're willing to step into it if you can frame it up like that I think you're much more likely to keep moving them towards it and leaning in a little more I guess constant encouragement hanging a carrot making it safely right it's like all these different things
I try to make it a core value of the department like you're going to fail and I had this big Grumpy Cat poster of like you're going to you're going to fail good you know Grumpy Cat I even had this award we called the Mulligan with like this golfer little Trophy and I would celebrate it if they screwed up like I love it yes ended up being a little bit too much because they'd be like not wanting to advertise that they had screwed up even though I was trying to make it like yeah we screwed up you tried something I didn't work great you're in the mall again award it's on your desk now yeah but it is it is a hard thing I think even with all that I did it's still the people who
had a growth mindset embraced failure and the people with a fixed mindset still kind of really has a dent to try to get out there and try stuff back and seen some of the careers of those people progress the ones with the growth mindset obviously flourished more and the ones that fixed mindsets less so but it is an interesting thing that mindset is a big thing it is a huge thing and and really I think really comes to the foreground and these moments of you know oh gosh if I would have been working on that where can I be today you know if we if we go back to the early days of social or the web you know if if you had the mindset to think oh my gosh what could this be like what what could I start learning at picking up here and there and I think
your trajectory just looks different today depending on how you engaged in those Transformations and again I think those Transformations were small compared to this one and I know you've probably heard that I really do believe that so I think it's worth continuing to encourage continue to talk about it in a in a spirit of positivity we're all in this together I think that's another thing that I would lean into is even if you do have pockets of people that know more really they're still beginners we are all still beginners and so setting that leveling that filled it's okay to be a beginner and I actually like to talk about being a beginner
failing at things to my children because they're beginners all the time and so that even with our teams like how do we reset that that bar and just be in it together I love that embracing student mindset I think that's a big thing I've actually just changed my LinkedIn profile whatever that mean bio header line is right under your name to just a marketer trying to master AI in 2024 with everybody else we're all together can you write me a better one actually nevermind I'll ask him to yeah I was just going to say I'm like just asking GPD
have you seen AI impacting your strategy process are you leaning into AI more is your crafting your go to market oh totally yeah it is it is okay so I now work 100% remote yet I'm in external processor I don't know that method only thing beside me wants to really Converse I mean it's just there is that part of me still wants to like bounce ideas I want to talk about things and so I really use it as kind of a thought partner so I'll throw ideas in I will ask what do you what would you do to improve this you know and really it's it's almost feeling that
of needing to externally process things with someone again it's not as fun as a person but it does fulfill that need for me and so I constantly run things through it and even if I think I've gotten a great idea I will just go plug it in and see what what would you do with this what is there something better than I could do with this and sometimes it's not sometimes my idea is better sometimes there's like a tiny little nugget or afraid or something that I think clarifies the idea better that I pull out of it and again it it's going back to it's just making my strategy
just that much better and certainly making it better in me having someone to dialogue with and and bounce ideas off of so that's really how I've been using it I love it I was had a conversation with my car yet yay about using AI as a co-pilot and that's kind of where I see you using it right here is essentially using it to help you go think about things yeah it is really helpful there's multiple times even for my own business I've been like hey here's a proposal I'm sending to a client what what's missing and it'll go through and be like hey based on what you read it's really good that you have a b c love X Y and Z here's some things you should consider I'm like exactly know but that
dang that's a good consideration to me is I think it does a fantastic job in its current state at that and it's going to keep getting better yeah yeah I can't wait I tried to make a custom GPT that was like a life coach and I said it all the information about myself strength finders profile life goals core values all the stuff and I like ask me questions be my life coach and it failed absolutely trying to put together and it was like the worst possible thing you could have ever asked to try to be as a life coach I will say there isn't coming out about and therapist that people are more willing
to tell you know like an AI driven in therapist about what's going on in their lives then a person and even if you go back to my strategy you know there and as much as like I'm think I'm a pretty collaborative person and love to talk things out with people they're certainly times where I may hold back on not knowing something or being unsure about something that I will who cares you know I can just put it in and say like we'll just you know like give me some other ideas do you even ask like what's the viability of this you know to get some input that I have no concern on the emotional side of
if it thinks my idea is good or bad or any kind of it's not providing any kind of judgment on the thing where with people you know you always have that and so it's just it's an interesting interesting Dynamic but a very powerful tool so many different questions I could follow up with that but it gets so it gets so sci-fi real quick that I'm like no and you can get as much as I'm like really deep this isn't that shows get back to the practicals yeah it kind of a final question for you what are you kind of where do you see where do marketing leaders need to be focusing over the next six months cuz it's hard to predict past
even before we even started recording I was showing you this new tool that I thought was really cool about video and I'm like wow I didn't think I'd be using any video AI tools for another 6 months to a year but here it is it's actually something that could be useful that I'm evaluating it's moving so fast what do you think you need to be focused on next 6 months yeah I think if you're not already working on leveling up your team and their knowledge base like now is the time I think right in the next 6 months I think you'll see a lot more AI tools that are ready off the shelf and that's going to be a great opportunity and things that are not on the what we would call the execution level of work you know if you think about it as
the manual labor being the bottom level of work that's being done when it comes to AI we've been doing that for decades that's robotics right now we're at that execution level and that's you know the personal it's me talking to Chad gbt it's me getting you know how can I get this graphic done fast you know it's all about just me executing my job faster I think the next level up from that is like the operations of the business and how do we cross functionally work how does information and intelligence across the organization and how does AI start to work in those Realms and I think I'm really excited about that that's where our known well our platform lives in
I think as you get in the next 6 months you're going to have more opportunity in that realm and that's something a lot of marketers aren't maybe not aware of yet that we are that we are here in the execution level and that there's a whole nother Horizon of work in an organization that AI is going to start to and be part of and change the way that that works so again I would say right now leveling up your team working on the execution level but having the visibility that we're going to go to a whole nother level of work in the organization that AI is going to start to impact so getting your team ready for that fantastic corny where can people go to learn more from you like
your best channels in order for people to reach out with questions and dive more into what you're doing now with no one will yeah well if you're interested in we are building an intelligent Enterprise operating system and the first product on the platform is known well client intelligence so all about retaining your clients pulling in all the different structured data as well as natural like routine Communication in your organization to Signal you when clients are in trouble so if you're interested in finding out more about that you can go to know when calm and join our beta waitlist and you can also find our podcast at AI know how wherever you listen to your podcast and then you can find
play on LinkedIn why can't I can't even think of my own handle this is how bad I am at promoting myself Lincoln the show notes yes please thank you I think that's everything I'm hoping to do a deep dive with your head of Technology soon and we're going to be going the whole known well thing how it works getting into some of the Nitty Gritty I'm really looking forward to that episode that's why I held back on your platform usually I like to dive into tool actually I'm so excited about that I will say if you are a marketing leader and wanting to just look at your Readiness we do have a free assessment known well calm slash assessment and you can go through a whole our whole proprietary
Venus assessment kind of figure out where you are right now where you need to go just know ahead of time you're probably not going to be great that's okay it's going to show you where the areas that you need to be improving on more specifically fantastic thanks for joining me today yeah thank you
