Messaging in the Early Stages: Lessons From and For Startups

#messaging  #startups  #founders  #b2bmarketing  #entrepreneurship   #b2bstrategy 

Messaging at the Early Stages: Lessons From and For B2B Startups

In this episode of Troupe’s podcast show SAID DIFFERENTLY, the focus is on messaging challenges and opportunities at the early stages for a B2B company. With guest Deirdre Mahon, who is VP of Marketing at startup venture studio super{set}, she and host Jennifer Sikora (advisor to Troupe) discuss their experiences and lesson learned working at and advising pre-seed companies.

The conversation is filled with their real-world examples of how to evolve the founder’s way of telling the story to the market; finding the market feedback signals that help you adjust your message; the risks in thinking about creating a new solution category too soon; and more.

Key timestamps in the episode:

02:30 = Differences in thinking about messaging at early stage vs. more established companies
05:22 = Evolving the founder’s way of telling the story
06:24 = Daily GTM feedback standups
08:10 = Preventing knee-jerk, premature messaging changes; What is the insertion point to lead to conversion; finding patterns
13:36 = The allure and distraction of wanting to do category creation, lessons learned
19:50 = Examining if it’s time to adjust messaging, looking for the outside-in signals
23:21 = Messaging strategies around “building in public” – how to stay authentic and effective

Read more from Troupe's blog about how to make new messaging succeed: https://www.troupe.ai/stories/why-new-messaging-fails-and-how-to-make-it-succeed

Credits:
Troupe.ai for sponsorship: https://www.troupe.ai
Graphic and production support: 24 and Up
Music: https://pixabay.com/users/backgroundmusicforvideos-46459014/

Said Differently is sponsored by Troupe, the AI hub for messaging success. You can watch the video versions of these podcasts on our YouTube playlist.

Transcript

SPEAKER_01 0:14

Hi everybody, welcome to this episode of Said Differently, your show where we discuss all things B2B, go-to-market storytelling, messaging, strategy, and tactics. Sponsored by Troop, I'm your host, Jennifer Sakura. We have with us a guest today who I've known for longer than I care to admit, Deirdre Mahone. She is with Super Set, which is another startup studio. So Troop also came out of a startup studio. So Deirdre and I have a lot in common. We used to work together way back in the day at Golden Gate, which got acquired by Oracle, but we've all been, we've both been at startup companies, mid-sized companies, bigger companies, but we're both in early stage world right now. And that's the focus of today's show, which is early stage messaging. So Deirdre, can you tell a little bit more about your role at Superset?

SPEAKER_00 1:05

Yeah. Thank you for having me, Jennifer, as your guest. I'm excited to get uh stuck into some interesting conversation. Hopefully, we can do it differently. So uh SuperSet, uh, we're based in downtown San Francisco, uh, classically called a venture studio. We like to say we're company builders, we form new companies from scratch. Often we're we're looking to attract future founders, and they could be uh product engineering people or they could be just business entrepreneurs. Um as long as you have a great idea, some domain expertise, the passion and grit to actually start a company, then we're we're all ears. Um inside the company, we have 12 in our portfolio at varying stages, and then my role is when they're early stage, I usually get stuck in there with all things go to market, which vesting is a part of. Um, and then I do a variety of other things, not only for the superset brand, but um I run like monthly learnings for the whole portfolio. So everybody on the go to market team, including founders, by the way, great, can join those learnings. So there's lots of fun things, and it's always changing, never boring. And yeah.

SPEAKER_01 2:23

It sounds so much fun, Deirdre. And you're such a great fit for them, and they're lucky to have you. Um, you know, one of the you and I had a prep call for this, and you know, we were chatting it, chatting up what it's like to, you know, really think through messaging at the earliest stages of a company's life. And every company from day one, they're they have a story that they're telling to the market, right? Like they you don't wait, like that's happening out of the gate. And you know, so but there were some differences and some similarities to messaging at established companies and early. There's some, you know, principles and fundamentals that are true regardless of what stage of your life cycle you're at. Like, so for example, some of the fundamentals are the same. You should be thinking about buyer-focused messaging and um, you know, thinking about you know the way you structure your story, talking about problems you solve. But that doesn't always happen, right? And it at earlier stage companies, it's harder for them to measure the effectiveness of their messaging. They don't have as many at bats, they haven't been around long enough, right? So their their sample size is smaller. What difference do you see between early and later stage in terms of what's top of mind for messaging?

SPEAKER_00 3:41

Yeah, you're you're completely right. You do have to think about the the building blocks and the sort of fundamentals of how to reach your audience. So knowing exactly who you're going after and why. So often when you're young, or I'm talking about pre-seed, right? You're really just sort of in launch process. Um, so you want to have like a very strong opinion and a point of view of what you're doing. So hopefully you're starting with some vision of the future. Um, I was actually chatting with some um creative team members that I worked with, they're based in New York, and um they said create a one of the things that really struck me, and it was interesting, like create a world, a new world, and then go live in it and invite others in. And I just thought it was a beautiful way of sort of saying, instead of like pushing your vision on everybody else and getting frustrated because they're not paying attention to you. So you want to create a world that's relevant to the target audience. Make sure that you're speaking in the language that is familiar and that will they will understand. Um, I think one of the challenges for early founders out the gate is that you know, they they're pushing their product too soon, they're speaking in jargony terms, or trying to come up with like what's the market, new market segment. Like all of that is doesn't matter.

SPEAKER_01 5:15

Yeah, definitely. We're gonna talk about the new market segment piece next. But yeah, you're you're absolutely right. Like founders out of the gate, and you and I have worked with a lot of different ones. They're not all created equal, right? They're not all the same, they don't operate with the same styles. There are some that are more marketing oriented and those who are not. And but the founders generally really are very wedded to the story that they think they should be telling. And they're obviously very wedded and and in love with the product that they built, right? That's that's the baby. You don't want anyone to think their baby's ugly. So, how do you shift a founder who is really married to this way they have been telling the story? And that maybe that's very technology focused and feature function focused. What do you do with these founders, Deirdre? It's super set. How do you approach coaching them and what advice do you give them?

SPEAKER_00 6:13

Yeah, great question. So it'd probably be easier if I explain it in the context of one of the young companies that I do love real examples.

SPEAKER_01 6:22

Yeah.

SPEAKER_00 6:23

So, I mean, obviously, you're a small team, so you have usually on the team, there's you know, the founder or co-founder, somebody's responsible for a product, the other person's more business. Then you might have some BD sales people on the on the team and myself. And we literally have daily stand-ups, it's half an hour. Um, you're you've already got a minimal viable product. You start, you've built a website, you've got some basic messaging. What you're now doing is validating. So every conversation with a future customer is a validation point, and the learnings happen because you're on this daily stand-up together. So you got the marketing lens, the BD lens, the founder lens, all together, all learning all at the same time. I really love that cadence. Yeah. So it's like, you know, engineers do daily stand-ups, it's just normal practice usually for engineering teams. I'm not sure in the AI world if they do that, but yeah, um, at least they used to. But I love that the the founders right there learning alongside you and asking the other people in the room and openly sharing what they heard on calls. Yeah. And I've seen in a matter of a few, like literally two weeks, um, with say 40 calls under their belt, I've seen that they've adjusted their messaging. They not only narrowed the focus of what they're saying, yeah, and but they adjusted according to the type of people they're speaking to, their pain points, and speaking less and listening more. Like we all talk about this, it's best practice, but when you actually put it into practice, you you learn so much because you're getting the buyer to open up.

SPEAKER_01 8:09

What you described, and I'm gonna actually switch the sequence of the conversation that we had planned, because what you described works really well with something that we had on the list to discuss. Um, having that we or daily cadence, I think helps prevent what I have experienced to be very mercurial or knee-jerk decision making around what I call either the last, the most recent great sales disc conversation or the most recent bad sales conversation. Because what can happen, I think, in my experience is that you will that will be very strongly felt. And maybe you have somebody having a very big reaction to that, positive or negative, and that can suddenly convince oh, we need a change. But that's one data point, right? So you're looking for patterns. So if you're having that sort of daily cadence, and and now you're looking for, well, was that a one-off? Was there something unique or different about that? That maybe we need to adjust messaging for that type of ICP or that type of persona, but we don't need to like redo the whole thing.

SPEAKER_00 9:20

Yeah. Yeah, the the learnings that we're taking away from this is so everybody gets to see and hear the calls if you want to take that time, or you know, AI will summarize it for you. Right. But the learnings is like the the segment that that customer is in, the their pain point, their um their persona, their degree of decision making. So it's not just oh what worked, what didn't, but really putting it into the context of did this land? And in this particular company's case, they're fairly early, like it's really innovative.

SPEAKER_01 9:59

Sure.

SPEAKER_00 9:59

Everything we do here is AI native, it's quite innovative. So we're we're definitely looking for is the market too early, right? Is this the thing about early stage, right? Yeah, so it doesn't mean that the the vision is landing. We're getting lots of head nods on vision. The next step now is conversion. So are they ready yet? Right. So these are not wasted calls because you're educating people, right? But um, but it's all about like really trying to listen and find out what is that insertion point and that sweet spot or catalyst that they're doing at their organization where now the timing is perfect. So you're constantly looking for that. Oh, I'm now seeing a pattern, let's try and go find that pattern again. Yeah. So in their example, it's like, I'll just give you an example, which is if a if a company is rolling out new pricing, ah, interesting, they need some help, right? Or if they're rolling out a brand new product or capability feature set, insertion point. So this is way more nuanced than like firmographic, demographic persona, you know, type. This is much more what's going on in their world that would trigger us to be perfect fit at that time.

SPEAKER_01 11:16

Yeah, yeah, great. I that's so that's so great. You know, and obviously a troop we're trying to tackle a big chunk of that problem at well. But for companies that are a little bit further along and have a much larger reach and data set, but it's good to really start thinking about that in the earliest stages, which is, you know, are we being consistent with our message? Are we applying it in the way that we we all agree we should be applying it? And if all of those things are true, then what's happening? What are the characteristics of the person we're talking to and the way we're saying it that is either advancing it or stalling it or, you know?

SPEAKER_00 11:53

Yep. Yeah. And what's beautiful about doing this on a stand-up basis is we we literally go around the room and we say, What do you think? What are you hearing? Because different people hear different things. So it's not a case of the CEO founder saying, Hang on, based on that last conversation, as you said, I'm gonna change everything. So you you you have this window of time, you go at it, you take the learnings back, you discuss it and adjust course. Yeah. Um, so yeah, that's that's that's great.

SPEAKER_01 12:23

I also advise early stage founders to just take a take a beat, right? Don't if you're gonna go through uh, you know, a big rewrite of your messaging approach, you know, s sleep on it overnight, you know, like don't totally totally.

SPEAKER_00 12:40

The one thing I will say is um, yeah, it's it's like the the quick takeaway is stand in your customer's pain. This is a this is a um I'm quoting one of our general partners, and he talks about it like literally get into the DNA of your customer. It's it's like what keeps them awake at night, where do they hang out? What what kind of places do they find their information and content from? Like the you really want to understand it. And I was actually remembering one of our customers when we worked together years ago. I found out that he liked Guinness, and uh I literally shipped him um a little Guinness labeled fridge to sit under his desk, right? So, like that's the kind of stuff that you really want to pick up on when you're trying to get super toes to the customer. It's true. That's kind of a cute little example, but yeah, that's the kind of learnings that you're taking as opposed to constantly talking at people.

SPEAKER_01 13:34

Right. Let's come back to something you mentioned, um, kind of kind of at the top of our conversation, which kind of relates to category creation, right? Not everybody has to create a brand new segment and give it a label. Um, there is an allure to that, and but there's also a harsh reality to it. And I'd love, I know you have a lot of things to say about that, as do I, on the topic of category creation. I've certainly met my share of founders um or early stage executive teams who are like, let's create, I think this is a new category, or we're we're defining a new category. Um that's a tricky bit, right? And it's not always necessary. Um, I'll share a quick example from my background in advising a startup company without naming names. They um fought like crazy against an existing established category that they did not want to be put into that category. Almost every sales conversation, the prospect was saying, Oh, so you're kind of like this, and they contextualize it to a category that they were familiar with. Oh, no, no, we're not like that. We're this. This went on for quite a while, and it was a big friction point. And I think it took them a bit too long to recognize that actually what should have happened in that case was okay, you are familiar with this. Let us tell you how we're similar, but also how we're different. Um, and and what we bring to that that you don't currently have. Whereas in that case, you're actually aligning with a familiar category rather than trying to recreate a new, like do world building, right? What are your what's been your experience on category building?

SPEAKER_00 15:26

I think it's all timing. So the because startups are doing something different and innovative, they want to um, you know, make a mark for themselves and they want to do something really meaningful, right? So it's like, oh, there has to be a new category. Maybe it's kind of sort of like that over there, but we're gonna rename it. And I've been in those rooms where it's like, let's come up with a three-letter word phrase.

SPEAKER_01 15:51

The three-word phrase, the magic three words, yeah.

SPEAKER_00 15:56

Which is such a waste of time in the early stages, right? Unless you have signals that there is a product market fit here, right? Then don't go off creating categories out the gate. It's not for the faint of heart, it takes a long time. And by the way, category create and it's expensive, yeah, not just in terms of resources, but like for tons of reasons. It takes the best part of a year-ish to um to category name it nowadays. A few years ago was more like two plus years. Um, I think category creation is interesting for the provider vendor, not so interesting for the buyer. So the buyer ultimately just wants to know can you solve my pain and how are you going to do that? And are you gonna stick with me? And can I trust you to do that? Right, that's ultimately all they care about. Yeah, so early on, you want to get enough traction in the market, enough customers, hopefully falling in love with what you're doing, even referring you to others. Now you have some foundation to build upon, and then go create a category and don't do it in a vacuum. Make sure that I love your example of um that story where no, no, that we're not that, we're this new thing, right? Right. Yeah, yeah. Yeah, differentiate from the incumbents.

SPEAKER_01 17:20

And often you don't get to be the one to pick the name of the category anyway, right? Now we can have a whole separate topic about what will the future of Gartner be. That we'll save that for a rainy day. But you don't get to you don't always get to pick. No, this is true.

SPEAKER_00 17:39

This is true.

SPEAKER_01 17:39

You can invest a lot of time, energy, and money only to have maybe even a bigger player move into that space who has much deeper pockets, influence analysts more than you can, and yeah, you're trying to fit into this other description.

SPEAKER_00 17:58

Yeah, and it's often, I do get this question a lot about category creation from founders, and it's often a windy path to getting there. So, like when we were both at Golden Gate Software, which ended up at Oracle, um one of the leaders on the team decided to call it like, I don't know, transactional data management or TDM replication under the covers. Oh my god, that transaction TDM was too damn much, right?

SPEAKER_01 18:25

We did have that joke. Yeah, we did. I don't know if leadership knew we had that, but we did.

SPEAKER_00 18:30

Yeah, that's okay. Now they know. So uh it was fun. Um, but we ended up just talking about it in the outcome basis. It is middleware, cool, whatever, there's lots of middleware things, but it would ended up being real time. So real time is actually the the outcome, what you get. Yeah, it's not like it's not three-word boring descriptor, right? Yeah, yeah. Yeah. And then I went through the same exercise when I was at Honeycomb, which is in the observability space. Right. And the incumbents were big companies like Datadog and New Relic, which is application performance management, very descriptive. Um, observability, not so descriptive. In fact, I was like, geez, do people know how to spell that? Like it's long, it's a long word, right? So, anyway, it turns out that no, that's the category. And we did actually end up with one word, and we just taught the world it was different. We definitely compared it to APM application performance management. Yeah, yeah, there's different paths.

SPEAKER_01 19:40

I so this is it kind of dovetails well to what we were just talking about, but and we touched on this a little bit already, but what are the signals you're looking for that it is time to pivot your messaging? Like what you've started with, what you're bringing to market, you've been can maybe relatively consistent about using it across your team and your content, and you know, you're just not seeing the results. You're you're or it you think it could be more, or maybe something else has happened that you know that's sort of obvious, right? If there's an external trigger, okay, we've added a new product, there's MA or whatever, then you're gonna have to adjust. But let's say things are status quo, how do you how do you know it's time?

SPEAKER_00 20:30

Yeah, and I do think it's sometimes it's easy to blame messaging, right? Like I like where this is going. I do, I have been in situations where it's um, you know, you work closely with sales, and sales is like, it's the message, right? And like we know that changing like a significant change to your message can be really difficult and time consuming.

SPEAKER_01 20:58

And they may not adopt it anyway. I'm talking about the sales organization. Yeah, right.

SPEAKER_00 21:02

It's a little scary, yeah. Um, or are sales actually using the messaging that you all agreed upon X time frame ago, right? There could be lots of different reasons under the covers. So I think you have to examine it closely. I think you have to um experiment before you do this carte launch, everything changes because messaging lives everywhere. Then you probably have to take a segment of the market, maybe you try it on for size, do something, experiment, get some feedback, and you know, you can turn really quick learnings around from doing some just very dedicated ads, for example, with this specific cohort. Um, I wouldn't advocate, oh, especially if you're further along, right? And you have gotten customers, or you go back out to the market and you just talk to your customers and do a lot more listening, which is kind of the original point we made.

SPEAKER_01 21:58

That's right.

SPEAKER_00 21:58

Yeah, and hopefully. You've got some gong calls that you can all listen and learn from.

SPEAKER_01 22:04

Right.

SPEAKER_00 22:05

And all the way through. Yeah. True. Thank you. And all the way through to you know your customer success people. A lot of times there's knowledge and wisdom that customer success teams have that doesn't always bubble back and close the loop and feedback to the top of the funnel. Right. Right. Um, yeah. So I I just be careful. You can make adjustments based on new product offerings, of course. But at the end of the day, um, it's the outside in signal that matters the most.

SPEAKER_01 22:34

Yeah. I think those are all really great practical pieces of advice that um I will click click down on twice, three times. That's good advice for early stage teams to listen to. Um certainly it can be messaging that's your problem, but I think you don't want to just automatically assume that that's the root cause. You have to really be thoughtful about how are you isolating that that's the issue. And then, you know, and I love the idea of testing that with small cohorts and you know, so small sample sets and getting that feedback and comparing it to what the main what the mean is for you know for everything else. So it's great. Um last topic I have for you, um, a big messaging kind of trend. Maybe it's not as trendy anymore. Sorry, I'm a little slow on the trendy stuff, but building in public um is a big theme right now, especially on social media, LinkedIn, X, what you know, name it, pick your poison. Um, you will see folks doing posts where they are, you know, sharing specific kind of things they're doing at their companies and making it very transparent, right? And so the build the concept of building public is that transparency, that under the you know, behind the scenes look, and what are the outcomes of that and giving people sort of this insider view? What is your feeling about that as a messaging strategy? Do you like it? Do you not like it? Like mixed feelings. What's your take?

SPEAKER_00 24:12

So I would say more mixed feelings. I like the the generally I like the authenticity factor. Yeah um, and you know, when you're being authentic and you decide to build in public, then you have to give the good, bad, and ugly, right? So I think we can all see through, oh yeah, they're just basically bragging again, right? So if it's if it's like try feigning authenticity, but ultimately bragging, I think we can all read to that. And that's that's a bit off-putting. Um it depends on your tempo. If you're doing it all the time, it can just be noisy. So I think you have to be a little careful and then ultimately like think about your audience. Like, what are you actually imparting and what's in it for them? If it's just a lot of more like, look at me, I'm gonna die awesome, then that just gets it, it's not gonna stand the test of time.

SPEAKER_01 25:09

Right. Is it helping you build trust with them? Is it helping you build a rapport or I get you, right? Like those are good things.

SPEAKER_00 25:18

Yeah. So I think like I read uh something just this week from the founder of Clay, and Clay is uh, you know, a go-to-market darling these days, and they've seen rapid growth. So hats off to not initially though, took them a few years, took them seven years to to get to that point, but um there was uh quite a long sort of share in it was in X, formerly Twitter. Um, but it was worth it was openly sharing how they run their own GTM engineering teams and learnings and practices from that. So he was exposing what we do as a company when we're doing GTM and the learnings thereof. So I did read that. That was really interesting. Yeah, it was useful, it was informative. One of my co-founders shared it with me, asked for my thoughts and opinions. So it already had like even a little viral effect inside our studio. So um, when it's useful, then great, yeah. But if it's just navel gazing stuff, no.

SPEAKER_01 26:21

Yeah. And I would add I it has to come from one of the founders, right? It it ha if it's being posted from the company account, you know, it just doesn't land the same, right? It it's it's storytelling, it's the founder or somebody that's part of like the the, you know, I wouldn't, they don't always have to be the founder, but somebody who's sort of fundamental to the team. In a leadership position. Yeah.

SPEAKER_00 26:44

You have to have strong points of view, you have to have some original thought, you know, can't just be regurgitating the same old, same old. Um the one thing I will say is uh so if you watch the Super Bowl and we all love Bad Bunny, the beautiful thing about Bad Bunny when he was on the field entertaining us, he didn't, he wasn't like I'm the front man chest pounding. So the way he presented himself was I'm part of the community, I'm in this together, here's my team, we're all providing this entertainment. Um, so I love founders that elevate their team. If you're gonna do this build in public, then promote what's happening, just like the play example. Like, look what our team is doing, as opposed to me, me, me. That can get a bit old. Great. So I think it's you it's important to just pay attention to how you're doing it.

SPEAKER_01 27:38

I think that's such great advice. I love it. This has been an awesome conversation. Any thoughts on founders for their messaging strategy?

SPEAKER_00 27:50

Um, so before we jumped on, I was thinking um the hard part, the hardest part about young companies coming out and starting is you're it does feel like you have to be you're creating original art, you're innovative by very definition. So it's like you have you're really painting an original art piece as opposed to stealing and composing art from other places or other genres, and that makes it harder because it has to be beautiful, it has to be interesting, it has to be engaging. So it is this constant art and science, right? And constant getting feedback. So that's often what it feels like, and I think that's why I love startups because it's so new and it's so refreshing, right? Yeah, yeah.

SPEAKER_01 28:34

I I do too. Um, and these challenges, as hard as they are, are also a lot of fun, you know. Yeah. Um and uh yeah, so thank you so much, Deirdre. I I'm I'm so glad that the portcos at Super Set have a great marketing advisor like you until they're able to get ramped up enough to bring their own on. But you certainly bring a tremendous amount of experience to your role for them that even if they hire somebody in-house, they're not gonna get it, Deirdre. So thanks again.

SPEAKER_00 29:07

And likewise with Troop. Troop is lucky to have you as an advisor. So they're doing some really interesting stuff, so yeah.

SPEAKER_01 29:14

We're excited. Um, well, thanks again so much, Deirdre, and uh, thank all of you for listening. Take care. Bye.