
Every startup hits the same ceiling: your founder customers love you, but they won't get you to $200M.
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A
You all are at an interesting point right now where, like you just said, this company was built for founders by a founder, and that was who your initial customers were. And still a lot of your customers are entrepreneurs, founders, you know, people with small companies. And now, like many other companies that I talk to, you guys are moving up market, showing that, you know, enterprises can use you as well. And I would love to talk about this because this has been a theme when I've like, I can think of at least 6 CMOs at these different companies that also started in a similar place and then had to pivot or reposition themselves to then be attractive to enterprise buyers.
B
Yeah.
A
And so I'd love to hear about this journey and how you're navigating it.
B
It's every single company I've started, every single company I've worked at is doing the same thing. Yeah, you're starting with SMBs or founders because that's, those are your people, they're early adopters, they have high intent. Anytime they're starting to use new software and, and then, but then you hit point where you're like, okay, sure, if I want to stay at 15 to 20 million business, I can stay with founders, but if I want to hit 100 million or 200 million, I have to move up market. It's not sustainable to just be building for founders. It's a really interesting shift and I am a revenue marketer through and through. So typically, honestly, up until superhuman, I am just going to look at where the revenue could come from. And I'm going to say we're just focused on this like outcome driven, again, revenue driven. If we're going to get to 100 million, where is that money going to come from? And sit. And it's usually not from the SME, it's usually not from founders. And so with the caveat that founders and builders and startups, they might not drive you a large portion of your revenue or your net revenue or profit, but they have so much influence outside of that. They usually have a lot of clout in the market. They are evangelists, usually. They have typically have a lot of followers, followers on social media. They are influencers in and of themselves as founders. They're part of founder communities. They usually will go through, a lot of them will go through accelerators that have massive networks of people. And so we're, you know, we were thinking about earlier this year of okay, we need to know, we need to move up market and build our product for them. But we can't lose sight of the community that got us here. And so how, so how I look at that is I even have in our planning documentation we have. Okay, you know, 70% of our time and resources are going to go to moving up market because it's a big deal. Right. It takes a lot of effort and if you're not focused that much on it, it's not going to happen. You're not going to do a successful. But we're still dedicating time and resources to fostering the relationships within this community and ensuring that we're not leaving them behind because they will help us grow. Ultimately they're just not going to show up in your as a major like revenue Lin your P and L. Yeah,
A
but it's like what you mentioned earlier, there's a lot happening that you can't tie back to. Yes, it's this community that's helping drive it and you know that they also are the ones that got you here and can help with momentum as you move forward.
B
Exactly. And so I, I honestly was like, no, I was like, absolutely not. I'm not focused on this in January. And Raul, our CNO and I were like, look, like we got to think about it a different way since it we're not going to see them scale our revenue to 200 million. I'm actually actively hiring for a basically startup evangelist or startup program manager to build like host happy hours, be in the field, be having you know, really in depth conversations with founders and builders and the accelerators and really make sure that we're maintaining our foothold within this community and supporting it as we grow. So we're dedicating resources now while then a lot of the team is really trying to push us up in this mid market plus direction.
A
Yeah. So how did you know that a startup evangelist would have been like did you hear from your community? Like hey, you're forgetting about us. Like we need someone on the ground floor here or like how did you get that feedback to put someone in the communities?
B
So we just, we kind of just like I would say we forgot about the startups. We just, we weren't proactively communicating with them as much and we did see that we had a competitor that started taking over some of the accelerators that we originally were like 100% influenced in. And, and so we're like oh no, like how is this happening? It's like, well because we're, we have proactively built programs for them and we also, we used to have a super like a previous version of a superhuman first startups Program where we're like, just give them seats like they are our people. Right. And so we actually launched a new version of that where our offers are even bigger. You can join Superhuman with five seats for a year free. And that basically your entire build, your entire, like, founding team. We look at it as like giving back to our startup community and our founders and our builders. And we're trying to just go back and say, okay, I know you tried this other product, but ours is still better. Like, come back like, we're here. And it was. It was a little bit of a. Oh, we just lost this spec. It was like one accelerator that we started just like losing our foothold in. And so it was. It's a good indicator though, of what the. Of where we were heading, which is why we've now pivoted back to making sure we have resources there.
A
Yeah. And I'm guessing you could see direct metrics tied to losing that accelerator partnership as well. Like, that'd be a pretty obvious one, I would assume, right?
B
Yeah, I mean, it wasn't as. Again, like, the revenue is still little. They're tiny, tiny deals and we're giving them big offers. So it's really just a. This is more of an anecdotal and subjective view of, like, in the conversations we are having, we keep hearing about these competitors starting to pop up. And so we needed to stop and redirect then after that.
A
Okay, so now as you're moving up market, what have been some of the biggest learnings. Hiccups. I mean, I can imagine that's a. Interesting process to go from marketing to founders and positioning the company that way and being like, me too. We're the same. And then all of a sudden having to probably, you know, reorient in a very different direction, which would require. I mean, to me, it sounds like it could be a whole rebrand in a way of like everything that you've been doing. So what have you been learning along this process and how's it been going?
B
The great thing is that we never tried to move up market and failed. Like, we're in the beginning stages of this and so. And we have a really solid brand already. Like, if you. We have a wall of love on our website. If you just are Even ever on LinkedIn or following superhuman, it's just like people just talk about us without even ask, without having us ask them to, which is great. Like, we just have so much customer love. And to us, it's like, we don't need to rebrand. Our brand is fantastic. Fantastic. We just need to leverage what we have and do it right as we're moving up market and really building for this new audience. And so it kind of goes back to the values, the outcome that our product is driving. Like you can be a founder of a five person company and you can also be an executive at a 5,000 person company and the value is still the same. And so what we now have done is we're leading with our product value. We're really leaning heavily into, of course, the outcomes we're driving for you, what it means for you and your workflow. And then we're adding the enterprise credibility on top of it. So you're getting, you're increasing your speed, you're increasing your focus. You know, it's a delightful product. Like we know you hate Gmail and Outlook, so like use ours. And then the signals on top of that for enterprise, it's. We also have SAML and scim. We have really great implementation if you want it. We have security and admin controls. We add that on top for the actual buyer themselves. But we're leading with, you're going to see this value as a user and if your whole team is on it, you're going to compound that value the more people you have using it. And so we did have to add Personas, of course. Like we now have business transformation leaders, AI leaders, biz ops. Like there's just more people that now we have to build narratives for. But it's still rooted in the same product value and the same brand narrative.
A
Yeah, I was just reading a piece around how you should be writing those narratives for, for example, for a, like a product like this, how your CIO is going to read your, you know, security for this product here, you can give them this one pager so they know exactly how secure this is. And here's all the questions they're going to get or what questions your CEO is going to ask. Well, here's how much is going to save on headcount and time and whatever. Like just having these documents ready for the whole network of buyers that will be waiting as you move into these enterprise deals.
B
Yeah, you're just expand, you're expanding like, and I think some companies do need to regroup and say, okay, was the brand we built five years ago, is it still going to work? Hopefully if you went through that process correctly. Like, yes, because you want brand to keep going. It's such a marathon, right, to build that affinity. And that is what the Superhuman team did, which is great. Like it's it's worked well for us. Like, I feel very lucky to come in and not have to do a rebrand and like not have to focus on that. Like there's so much momentum. And so then it's taking that into your point, it's making sure you're saying the right things, you're building the right material to help have those conversations and move those deals through. It's not easy. It takes a lot of time. Right. Like I, I restructured my product marketing team so now I have a product marketer who is only dedicated on moving up market and landing managed deals with sales. Like, that's all he does and he's really, really great at it. But you know, we just did that three months ago, three or four months ago. We just kind of pivoted our teams to be organized that way.
A
I could imagine maybe it's slightly easier for you all because you haven't been around like a really, really long time. Whereas I'm thinking about other companies, even one, like maybe Canva for example. They've been around a while and they were really so branded as, you know, just the startup's friend and now them trying to move to enterprise. I feel like they probably could have a harder time because they just were so well known as one thing and just, you know, like, oh, we're just like a basic tool for basic design, you know. And now they're like, no, we can do everything that Adobe can do. Maybe like you should use us to enterprises. But it might be easier because you, you weren't branded for like a decade in the market as, you know, one thing for one group of people.
B
Well, it's so fun. I actually we had our first ever like go to market off site in February. Where we did it was just sales, marketing, cs, do a bunch of training. It was like vision setting. And I had this whole presentation on examples of companies who have started as B2C or self serve kind of individual products. And I've moved into the enterprise and Canva was an example I use. So it's like, like I had four slides and Canva was like, here's where they started this year, then it went to this year and then here's how their messaging and narrative changed along the way. And like Canva started as, yeah, a design tool where you built like ads, you know, for your or just for anything but like ads or flyers or whatever. And now they call themselves like the visual design tool or visual design for everyone. And there's all these different use cases and they've built Their team's work, you know, their team's workflows and Org structures and things like that from their product. And I was trying to paint that picture for our team of this is. And I had like, you know, a timeline. I was like, we're. We're like, early on, we're here. This canva did this really quickly. Right. Like, not a lot of companies can make that pivot as fast as they did. But. But that's where we're going. We're trying to become not just an email tool, but an AI native productivity suite that is email. It's calendaring, it's task management, it's, you know, you name it. Like, that's on our roadmap ultimately to build. And that requires a lot from everyone in an organization to really get there. But it's fun. It's really fun to do.
A
I mean, that's such a different mentality to how you just explained it. Because one goes like, maybe the original use case of Super Superhuman was this is your end destination. Like, this email solution is your end destination. And now you're saying that's just the starting point. Like, we're going over here with all the other things and how to open up the portfolio of like, offerings and showing people like, this is just the starting point is the email productivity solution and all these other things.
B
Yeah, and I think it's. I've my vision really for not just Superhuman, but productivity in general is if you use email, you can see value out of Superhuman. You have a lot of email, you can see even more value. But what if you could log in to this one instance of Superhuman, for example, and AI has now read your emails, it has read your calendar, and it's read your chat across personal and professional. And then it says, hey, today, here are your top five things and here's what you need to do and what you really need to focus on in order to, like, be a successful leader or operator. And I look at that, I'm like, that would change my life. Like, I'm using Superhuman both personally and professionally. But I have two instant, like, I have two different, you know, login instances of it. So how do we, like really combine that of like, you're a productive person versus you're just a productive professional. And I just think it could completely change the way I want that as a human. I want that.
A
I'm looking at that for all of my tools right now. When chat, we have our ChatGPT Enterprise account. And then I've got my personal Stephanie Postals one And I'm like just put them together. Yeah. And I want to be able to share all these with my team. I don't want to have to only do in the enterprise. Like it just it's. But it's interesting because that's how the world was for a long time. It's like keep it so separate and you don't want people seeing your dinner recipe accidentally in chat GPT on your work account. Like so I think it's interesting how now people are like no, just. Just make my life easier and just merge things. Give me time.
B
It's. It totally is a. It's a mindset shift. It's a habit change and we talk about it a lot. Like you know, a lot of some of the features that get requested of us is unified inbox so I can unify my personal and professional and there's a lot of schools of thought there where it's like but that makes you less productive. Like how do you have. Because you're thinking about things differently. I'm like, yeah. Yes. But the reality of it is like sometimes my kids school reports are more important than this business meeting. I know crazy. But I might have to do that first. Respond to that email first versus this one. It's also a very personal decision and so I'm all about build the flexibility for how people prefer to run their lives and then we shouldn't tell that to them themselves but we should let people build it.
Date: March 4, 2026
Host: Stephanie Postles
Guest: [Name not given, identified as "B"], Revenue Marketer at Superhuman
This episode dives into the critical juncture when a successful startup transitions from serving founders and small businesses to targeting enterprise clients. The guest, a revenue marketer at Superhuman, shares the lessons, strategies, and challenges involved in "moving upmarket"—a pivotal shift for any SaaS company wishing to scale past $20M toward $100M and beyond.
Key themes include:
Startup Roots, Enterprise Ambitions
"If I want to stay at 15 to 20 million business, I can stay with founders, but if I want to hit 100 million or 200 million, I have to move up market." – B [00:45]
Balancing Focus: 70/30 Split
"We're still dedicating time and resources to fostering the relationships within this community and ensuring that we're not leaving them behind..." – B [01:56]
"We did see that we had a competitor that started taking over some of the accelerators that we originally were like 100% influenced in. And, and so we're like oh no, like how is this happening?" – B [04:17]
Brand Strength and Narrative Consistency
"Our brand is fantastic... We just need to leverage what we have and do it right as we're moving up market and really building for this new audience." – B [06:56]
Personalization for Enterprise Buyers
"We now have business transformation leaders, AI leaders, biz ops... But it's still rooted in the same product value and the same brand narrative." – B [07:58]
Team Structure and Focus
"I restructured my product marketing team so now I have a product marketer who is only dedicated on moving up market and landing managed deals with sales." – B [09:30]
“[Canva] started as... a design tool... Now they call themselves like the visual design tool for everyone... I was trying to paint that picture for our team...” – B [11:00]
Productivity Platform Vision
“What if you could log in to this one instance of Superhuman, for example, and AI has now read your emails, it has read your calendar, and it's read your chat across personal and professional... I look at that, I'm like, that would change my life.” – B [12:49]
Changing Mindsets
“...sometimes my kids school reports are more important than this business meeting... It's also a very personal decision and so I'm all about build the flexibility for how people prefer to run their lives.” – B [14:24]
On the founder to enterprise transition:
"Anytime they're starting to use new software... if I want to hit 100 million or 200 million, I have to move up market. It's not sustainable to just be building for founders." – B [00:57]
On brand consistency and expansion:
"We don't need to rebrand. Our brand is fantastic... We're leading with our product value... and then we're adding the enterprise credibility on top of it." – B [06:56]
On learning from competitor encroachment:
"We just weren't proactively communicating... we had a competitor that started taking over some of the accelerators that we originally were like 100% influenced in." – B [04:17]
On product vision and unified productivity:
"What if you could log in to this one instance of Superhuman... and AI has now read your emails, it has read your calendar, and it's read your chat across personal and professional... that would change my life." – B [12:49]
In this episode, listeners get a grounded, tactical look at the challenges and opportunities that come when scaling from startup roots into the enterprise world. The Superhuman team’s solution is to maintain founder community ties, double down on their brand identity, build tailored narratives and teams for enterprise success, and set a bold vision for unified productivity—all while learning from peers and evolving customer expectations. If you’re considering (or already facing) the upmarket journey, this episode is both a roadmap and a reality check.