Acclaimed B2B marketing exec, Kasey Byrne, on avoiding marketing traps

Powered by RedCircle

In this episode, Elias Rubel is joined by Kasey Byrne of Rasa. A company building the standard infrastructure for conversational AI. With over half a million downloads since launch, our open-source tools are loved by developers worldwide, and Rasa runs in production everywhere from startups to Fortune 500s. Their friendly community is growing fast, with developers from all over the world learning from each other and working together to make text- and voice-based AI assistants better.

Episode Outline

[04:39] How Kasey apply big picture thinking into her career

[07:16] The trap most marketers fall into

[10:13] How to judge whether it is math question vs communications question

[12:04] Steps in developing team spirit and energy

[16:34] The process of seizing fabulous opportunity right now

[16:35] Lessons from running large marketing campaigns and listening to contextual cues

[19:22] The importance of running a good referral marketing strategy

[27:04] How Al is like chiropractic for the marketing plan

Kasey’s Inspirations:

Jonathan Cowperthwaite

Contact Kasey



Elias Rubel (00:02):

Hey there, all you cool cats and kittens and welcome back to another episode of best in SAS where each week we take you behind the scenes for conversations with some of Silicon Valley's best and brightest operators and investors. Crack a beer, get comfortable and join us on our quest to find the patterns and playbooks that accelerate the sprint to 10 million of that good stuff, that repeatable stuff, that stuff we call a R. R. So today I'd like to welcome a good friend, Casey Bern. Wait, actually pause. Sorry. Casey, is that how I say your last name? I've never sent it out last name out loud. Okay. I was like, I don't think I've ever said that out loud as I was reading it.

Kasey Byrne (00:46):

No, no, that's okay. It's I was ha, I was smiling because you didn't say burns, which is what most people do. So yay. I got it right.

Elias Rubel (00:52):

Score. All right. Not a Simpson's character. All right, restart. So today I'd like to welcome a good friend from the industry. Casey Bern. Casey is a software engineer, turned marketer with a passion for new technologies. Developer tools and fact based decision making, which will become very apparent throughout the rest of this interview. I'm sure. She currently leads the marketing at rasa. And with some really impressive Ivy league credentials. She credits raising four children to the skills that she needs to get the leadership job done. Casey leverages her experience as a parent, which I'm sure we'll hear a lot more about to lead her team successfully with mutual respect, enthusiasm, and a little bit of humor. Casey, welcome to the show.

Kasey Byrne (01:36):

Thanks Eli. This is great to be here.

Elias Rubel (01:39):

So I would love to start at the beginning because I as for all the times that you and I have sat down over coffee and talked to marketing, I don't think we've ever talked about your background in management and consulting. So I'm curious how that all came to be and then how you transitioned and, and maybe how that impacts the way that you make decisions today as a marketing leader.

Kasey Byrne (02:01):

Yeah. Right. So, you know, I think I, I, so I I studied engineering in school and, and was an engineer at digital equipment corporation back in the day for a number of years. And then I went to business school because what I found when I was an engineer is that the technical challenges were interesting, but it was the communications challenges and the business decisions that seemed completely intractable to me. Like, you know, I could write, I was writing behavioral models for modeling CPU design and that, that was great. It was fun, but it was like the fact that we had the 10 teams that were all supposed to be doing things the same at the same time that we had all these interactions that we were building for a market that at the time was probably 18 months out and nobody really knew how that was going to develop.

Kasey Byrne (02:46):

All those issues seem more interesting to me, which is why I went to business school. And then why I ended up at McKinsey, because it's, we Fundly used to stay at McKinsey. It's sort of finishing school for MBAs. It was, it's really an extension of the education. And I feel like, you know, learn a lot at McKinsey, but one of them is to step back and say, how does this fit? And constantly question whether the direction you're going in is the right direction it like, and did what piece of information that you just got did that, does that change where you're going? Which is something that's very important in startups and very important technology because things change very quickly, much more quickly than you can ever complete a task. So yeah. Mckinsey, I've been, I'm sorry. So ms, since McKinsey, I've done a bunch of things and one of the reasons I, one of the things I like very much about where I work now is it's very concrete and very getting things done. And there's a lot of focus on like measurable results, which is, which is a lot more fun than being on the other side of the table, just giving advice.

Elias Rubel (03:46):

So I'm really curious. Typically marketers fall into this trap or they can fall into this trap of, you know, there's so much marketing that can be seen as soft. And of course there's a quantifiable side. And knowing your personality and how kind of matter of fact and prove it you are, how do you, how do you approach marketing such that you don't fall into the trap of the things that are hard to measure or, you know, how do you begin to quantify those things?

Kasey Byrne (04:15):

I, I, this is a, this is a question of practicality rather than math. I, I mean, I, I, it kills me to say that it's pretty hard to measure anything at the level of granularity in marketing that I would, that I would like, like I would really like to know specifically how that blog post drove something along, you know, a good deal farther along and, but the attribution just isn't there. So what I tend to do is on a top level, say, all right, if, let's be very concrete about what our goals are and whether they are measurable or not. You know, for example, one of the goals I have for this quarter or working at rasa is to really map the education journey to a, an expert Russ, a developer and outline where the missing pieces are. That's you know, and that, so if we agree that that's the goal because we believe that we'll build our, that goes straight against a company goal that we have to build our community.

Kasey Byrne (05:17):

If we believe that our top level goals will reach what we want to have happen and we re we agree that the set of activities if executed properly should reach that goal, then that gives you the freedom to measure. Each of those individual activities is granularly as you'd like. Like how many pieces of content did you create? How much interaction did you get, how many more people came to your website? So what you like, but the, the connection from the I increased, I don't know number of people who came to the website by 10% this quarter. How did that drive sales? That's just too far of a loop. So I feel like the, the solution is to get the, an executive team like in really tight agreement that the set of activities that we're doing tie to will, if done properly, should reach our goal. And then you give them the freedom, dementia measure aggressively each of those individual pieces. Again though, that's a, that's not a, it's not a math question. It's a communications question.

Elias Rubel (06:14):

Sure. So, I mean, you, you've been VP of marketing or COO at at least five companies, probably more than that. Cardlytics, NPM, postmen, now rasa just to name a few. So I mean your, your ability at this point to pattern match and to have a certain kind of personal or fundamental marketing truth that you can come back to and lean on when you spin up at say, rasa, for example, as their new VP of marketing. I'd love to dig into some of those stories. Going back as you know, as far or as recently as you'd like to and talk about some of the big bets that you've made in the past and how those now shape your future as you begin to roll out programs at rasa.

Kasey Byrne (07:02):

Yeah. So there are always a couple things that feel like bugaboos and w one thing that I've been talking a lot about recently given the pandemic is tech events. Right? and I think I have, I, if I were to tell stories, probably the biggest success and biggest failures are around events, right? They're just, they're, they're enormously expensive in terms of money as well as team energy and you just, it's very hard to tell how they're going to turn out until you do an event. And sometimes events even change from year to year. So, you know, I, when I joined, I should, I should laugh. Like I joined I joined each of those companies I just described. And I used to, I joke that I answered the phone marketing department for, you know, at least the first couple of months. That's kind of a norm, a normal thing for me.

Kasey Byrne (07:51):

And I don't mind that. Like there's some, there's something joyous in like, you know, I do it or it doesn't happen. That really forces you to be very focused. It forces you to be very very product focused, right? You can't think too much. When I joined rasa it was about a month before, and I didn't realize this when I took the job, but there was, we had scheduled our very first Russ, a developer summit and the goal was 250 folks at a a lovely venue at Fort Mason in San Francisco. That would be the various first time we're going to do a big conference. And I said, cool, that's in a month. It must be all buttoned up. And Tim said, well about that. So I don't know. Like I'd never, I mean it was a month out, right?

Kasey Byrne (08:37):

We didn't, and we had nothing done, right? We, we, we had we had a venue and we had a speaker list, which is great. We didn't have any, we didn't have very little else, which is totally fine. It was, we totally pulled it together. And I think the my big aha on that is that like one of the absolute pattern matches is you have to have like toolkit of stuff you can just do. And it is absolutely true that a well-run self hosted event almost always makes the company, the company happy. It is, it is the, in my mind it's kind of the best kind of tech event because people don't come unless they're really interested in your company. There's no, there are, there is, there is not a distraction of too many sponsors in the sponsor hall, which you feel like you have to go to.

Kasey Byrne (09:22):

There's no, you know, in our case that we're an open source company. So we, we, you know, there was an obvious commercial aspect to this in the sense that we have a sales team and we want to sell enterprise, but you were more than welcome to come and just talk about open source and everybody there wanted to talk to you about open source. The employees of the company love to go to these things because it, you know, like it's an entire room full of customers. Like the product people are over the moon, right. Cause they're running around and, and if you can run those well those, and by well-meaning, you know, it, it more or less goes off without a hitch. You know, there, there is enough food. The party is fun. It's, it's like, it has the feeling of something that you really correctly spent your time attending.

Kasey Byrne (10:08):

Then you have just a great event. And we, we did spend, I spent really that entire month just working on that and it was worth it. It was like we had a great dinner the night before with some folks who are, who are from customer companies. We can trace a number of deals to, to that event. Like it was, you know, it was a lot of fun. It, we were, you know, the party was fun and, but I think that there's like that's money and time well spent and it's money and time that's spending at a, I don't know if sponsoring a third party event has never felt as it never has that same consistency. So I always tell people, if you think you can fill a room in your own event, it is almost always worth your time. And if you can spend a little money, a little more money on catering, a little bit more money on better AVS so you have assets after the fact you know, a little bit more money on a better looking shirt. I mean they seem like really small things and they really actually are, it doesn't take a lot of effort, but adding those all up like the sum turns out to be a little bigger than the sum of the parts, the total since we, so that's, I always go with that. 

Elias Rubel (11:13):

So I'm going to jump in because before we started recording, we were talking about events in the Valley and the kind of like one-upsmanship of everyone having to show up to the same event industry events and it's kind of like in a way a race to the bottom right. If it's not, if it's not your event, right? So how do you balance this kind of appreciation for the value of events and then at the same time like let's go there. I think that would be interesting.

Kasey Byrne (11:43):

I think that's, I, that's about where I was going to go. I was going to say, you know, to completely contrast or contradict myself might be thera I, if I never have to go sponsor another third party event, that will be happy. And, and what's interesting right now, our current environment, right? I can't go sponsor you know, the chatbot summit or the AI conversational AI conference. I can't go do that because they're not, they're not really happening and they are all moving to online. But it's not really clear how that's going to develop. And I think we have this fabulous opportunity right now to figure out what, what venues are, what, what types of events really need to be in person or really are valuable in person. Because six months ago I, I couldn't afford to not to not sponsor an event where it would make sense for us to be, I couldn't afford to just decide not to participate in what is a very expensive and very time consuming and often unpredictable results conference because we just don't know what's going to happen.

Kasey Byrne (12:42):

Whereas now we have this time where since everything's online, we have a lot, a little bit of time to experiment in a safer space. I would really do hope that that will sort it out and that I suspect that I will still be saying a year from now your own hosted small event is always worth the time and energy and then maybe there'll be a completely different set of messages about bigger ones. You know, like if I'm thinking about, you know, things that work and don't work. When I was a postman, we there are a lot of API conferences and we sponsored most of them, small or large. We had great success with I'm going to blank on the name. One of them was a modest, you know, relatively modest sponsorship. We, we always, our booth was always mobbed and because that we were because of that, we usually got a couple of speaking slots that felt like a good thing and they were, they were close and it was worth, it was kind of worth the money and effort, you know.

Kasey Byrne (13:37):

And then, you know, honestly, we did it. We experimented one year when I was a postman. I won't tell you which one, but with a very expensive, very big, very popular SAS conference and, you know, we just got crickets and it's just like, it's just too lumpy. You can't, it's not like a nice digital marketing campaign where you can spend a hundred dollars a day for a week and figure out where your keywords are. Right. It's just a very, very much, much, much, much larger piece. And so I do wonder about that third party event situation, whether that's gonna survive and you know or, or materially changed. And I do think it will. What, what would you like to see it replaced with? Do you have any sense? Well, I don't know. Like I do hope that is that we would find a way to make an online alternative WARF more functional.

Kasey Byrne (14:30):

Like I, we, we're, we are experimenting with our, we're experimenting with that ourselves right now at rasa with an industry in industry type event. We at rasa, we spend a lot of time talking about level three conversational AI, which is you know, takes real contextual cues and is more than just a single turn conversation. So we're doing a conference that's specifically about how do you reach level three and beyond? What is it, what is it that's required to make a truly contextual assistant. And we're experimenting with being online, you know, and I, you know, I don't know if it will work. I don't know if people will come. But if we start to do those now and they do start, if we start to get used to it the same way we got used to going to the conferences in person, I would hope we would have a very different mix and that the in-person conferences would be you know, only the ones that are super, super targeted and high value and are complimentary to the in person ones. I mean, to the online ones for sure.

Elias Rubel (15:37):

That'll be interesting to see how it all plans that pans out. So I'm curious, kind of going back to your playbook with the focus of the show, you know, post product market fit, you get your right around your first million in ARR and trying to sprint to that kind of elusive first big milestone, 10 million in ARR. What, so we've talked about events what other things do you personally come back to over and over again that have been successful? And if, if you could unpack a couple of stories?

Kasey Byrne (16:10):

Yeah. Well, you know, I think so I think it depends quite a bit on your go to market. Motion, right? So at rasa, you know, going at our, our paid product is a pretty large enterprise product. And so the things you would do to try to get to 10 million there are materially different than say a postman or an MPM where the average deal size was, you know, kind of smaller and a smaller team, you know, postman is about last time I checked is about $10 a person a month for the pro product and teams were in a much closer to the 10% size. So it's a very, it's a self serve model rather than an enterprise sales model. I think in the self-serve model the when I, when I sometimes call is no dumb marketing, right? Just there, there is a consistency and value about reaching those folks with messages that are related to what they're doing.

Kasey Byrne (17:15):

And a lot of companies are able to provide. If you're at a company and you have any information about the product itself and product usage itself I've seen lots of campaigns where you like, you can send something that is just fertile ground, right. One of the things we did at postman that was like in terms of open rates was shockingly successful, is when somebody signed up for a team. We sent them a series of really nice three very nice emails that just was, here's this document on how to set up your team. Here's a document on things. I w I think it was like things I wished I'd known, right? And then the key, this, this is the key, and you'll laugh at this. We sent everybody a coupon for five tee shirts for the team. And those three emails were opened very, very consistently.

Kasey Byrne (18:07):

You have a really captive audience and we didn't send it just to the person who signed up. We sent it to everybody who is associated with the team. And we we customized it slightly based on what we knew of those email addresses, what they had done in the product to date. So we didn't send them a setup if they already had it set up, we sent them a, have you tried these two features? So a little bit of progressive work there. But a welcome to a new customer, like with a T shirt, obviously surprisingly useful. On the other hand, something that worked not at all, well once is we offered, I guess I think this was also a postman. We offered a discount to existing customers if they were to refer, refer a month, get a month, refer a month, which you see in a lot of places.

Kasey Byrne (18:57):

You know, sort of kind of a personal affiliate model. Right? And, and we thought this would be really valuable partially because customers love to complain about cost, right? It's just the product's too expensive, you know, they're paying $6 and they want to pay five or whatever it was. Right? So we thought, well, if we give, we, we offer a free month to everybody that's, you know, that's not bad and sort of an 8% discount on something that's not very big and being with and they'll be able to share it with somebody. Right. So we offered this. If you, you know, if you share it, you know, if you, if somebody else signs up, you'll get a month off of your current yearly contract and we'll refund it right away. Nobody took us up on the offer, not a single person. I think literally nobody opened it.

Kasey Byrne (19:41):

And our takeaway from that was actually that is just outside your workflow. Cause the, the successful thing that I just described to you, those emails arrived right in the middle of you trying to do something that this should have helped your workflow. You just signed up for a team. I mean other than the t-shirt, which maybe it did, but, but we were providing something that should, should actually affect your, your, your thinking today. Whereas the other one no matter how good an offer it was, it kinda came out of nowhere. Right. if I were to do it again, I might offer it to folks just as they were about to renew and maybe that would've gotten more attention. But it was, it was a much more generous offer, right. In terms of dollars and everything else. Much more generous offer. Never didn't, no one ever signed up for it. It was really interesting.

Speaker 3 (20:30):

It almost ties back to the a level three, like the contextual awareness.

Kasey Byrne (20:37):

Nothing makes sense. That's the takeaway. That's right. Yeah.

Speaker 3 (20:42):

Very cool. Well, I love to ask this question as we wrap up, which is you know, we all have people in our lives professionally who either our peers that we, you know, really, really respected the work that they're doing or have done or mentors folks who have helped us along the way or, or that we just continue to look up to. I'm curious who a couple of those people are for you.

Kasey Byrne (21:04):

Is this like somebody, somebody you might know or are we thinking about somebody more senior or does it, there's this more directional I like, I'm not sure, like do it name yet.

Speaker 3 (21:15):

Yeah. Names. It doesn't really matter. Just, just folks in industry who either inspire you or you've worked with and you think they're just, it's like a shout out basically people who are doing really great work.

Kasey Byrne (21:27):

So I'm someone I worked with on and off a number of times that I think you might know is Jonathan Cowperthwaite. I worked with him at NPM. Yeah. I don't, I lost the thread of where he is these days. Always, you know, like actually always the person I text when somebody does something crazy and marketing and I need it. I need someone to snicker it over, over it with me. Right. you know, I at one point actually looked into with him, I looked into no dumb is an agency cause I'm like, wait, we could just go around and not just do, like, not do the dumb stuff like that. That would be our value proposition is we don't do the dumb stuff. We only do, we only do the smart stuff. Like, and I laugh about this all the time because I feel like I do actually have a super power and I did get this from someone I worked with in an industry you wouldn't know cause he's actually long since retired.

Kasey Byrne (22:24):

But when somebody worked for a number of years ago when I was in financial services taught me that and this because this was his super power and he passed it onto me. My superpower is in marketing is that I am constantly saying, who are we trying to reach? What are we trying to say and how can we get to them? And hand to God. You just asked that whenever you get a marketing plan that makes no sense or a sales proposal that like confuses you or somebody comes to you with a very naughty problem about how we should do personas. If you just ask those questions, who are you trying to reach? What do we want to say to them and where can we reach them? It, it's like chiropracty for the marketing plan. It fixes everything. Joe tumbler is actually the name of the person I'm thinking of.

Kasey Byrne (23:13):

It used to be the vice chairman at sun America and he just was, he was absolutely dead on all the time. He did not mess around. He was always crystal clear. And if you couldn't answer those three questions about any proposal, you were in deep trouble in his office. I mean, he was an incredibly gracious man. He was never, but like when he was starting to ask the questions, if you weren't prepared, you felt like that kid in elementary school, like I didn't do the reading, I didn't do the reading. Right. and yeah, so it's a, it's a thing, you know, so I, so I, I, I try to channel Joe whenever I'm feeling like I don't understand what's going on. He was excellently good at that. So yeah, enacting, focusing back to like just an absolutely just he would get this little look in his face and he would ask a few questions and 30 seconds later the complete fallacy of whatever I was trying to propose to him would be completely clear.

Kasey Byrne (24:06):

And as I say, you know, as you said when it might your intro, I, I do feel like, like learning how to ask questions that gets get for me anyway, I learned a lot from Joe, but learning how to ask questions so that the individual you're asking them of solves the problem themselves is something I have only learned really being a mother. Yeah. Cause it turns out I can't do everything for the kids. And so I, you know, I have to ask these questions and so, you know, what are you trying to do? What does it do? What format does it have to be in, how far have you gotten? And the kid goes, okay, you're right. And then they leave. I'm like success. So this is particularly cogent right now because all four of my children who are in high school through college aged are trying to trying to do work. They're trying to do school in the house right now. So and spending a lot of time full house. Yeah. That's great. It's all good.

Elias Rubel (25:05):

Well Casey, thank you so much for taking the time. I think there are tons of great nuggets in here for everyone listening and if anyone ever wants to see examples of just good marketing and no bad marketing marketing, marketing, there is no dumb marketing. Casey is the one to watch. I love that.