Scaling Past $20M (Spotlight): When to Move Upmarket

0:00You 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, people with small companies. And now, like many other companies that I talk to, you guys are moving up market, showing that 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 six 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.

0:41Yeah. And so I'd love to hear about this journey and how you're navigating it.

0:45Harmony Anderson: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 those are your people. They're early adopters. They have high intent anytime they're starting to use new software. But then you hit a 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.

1:19Harmony Anderson: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. 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.

1:58Harmony Anderson:Usually they have typically have a lot of 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're thinking about earlier this year of, okay, we need to know 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 I look at that is I even have in our planning documentation, we have, okay, 70 % of our time and resources are going to go to moving up market because it's a big deal, right?

2:36Harmony Anderson: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 it 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 line in your P &L. Yeah. 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.

3:11Exactly.

3:12Harmony Anderson:And so I honestly was like, no, I was like, absolutely not. I'm not focused on this in January. And Raul or C &O and I were like, look, like we got to think about it a different way since we're not going to see them scale our revenue to 200 million. And so 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, the accelerators, and really make sure that we're maintaining our foothold within this community and supporting it as we grow.

3:53Harmony Anderson: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. 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? 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.

4:34Harmony Anderson:And so we're like, oh no, like, how is this happening? It's like, well, because we're, we haven't proactively built programs for them. And we also, we used to have a super, like a previous version of a superhuman for 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 use it basically your entire building, your entire like founding team. We look at it as like giving back to our startup community and our founders and our builders.

5:07Harmony Anderson: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. It was like one accelerator that we started just like losing our foothold in. And so it's a good indicator, though, of where we were heading, which is why we've now pivoted back to making sure we have resources there. 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? Yeah. I mean, it wasn't as, again, like the revenue is still little.

5:39Harmony Anderson:They're tiny, tiny deals and we're giving them big offers. So it's really just a 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 that after that. 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 an 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.

6:26So what have you been learning along this process?

6:29Harmony Anderson:And how's it been going? The great thing is that we never tried to move up market and failed. We're in the beginning stages of this. And we have a really solid brand already. 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 having us ask them to, which is great. We just have so much customer love. And to us, it's like, we don't need to rebrand. 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. And so it kind of goes back to the values, the outcome that our product is driving.

7:07Harmony Anderson:Like you can be a founder of a 5-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 increasing your speed. You're increasing your focus. It's a delightful product. We know you hate Gmail and Outlook. So use ours. And then the signals on top of that for enterprise, it's we also have SAML and SCIM.

7:44Harmony Anderson:We have really great implementation if you want it. We have security and admin controls. So 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 in the same brand narrative. Yeah, I was just reading a piece around how you should be writing those narratives for, for example, for a product like this, how your CIO is going to read your security for this product.

8:35Here, 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 it's going to save on headcount and time and whatever. and just having these documents ready for the whole network of buyers that will be waiting as you move into these enterprise deals.

8:52Harmony Anderson:Yeah, you're just expanding. 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. It's worked well for us. I feel very lucky to come in and not have to do a rebrand and not have to focus on that. 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.

9:24Harmony Anderson: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. 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. That's all he does. and he's really, really great at it. But we just did that three months ago, three or four months ago. We just kind of pivoted our teams to be organized that way. 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 just the startup's friend.

10:08And 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 like, oh, we're just like a basic tool for basic design. And now they're like, no, we can do everything that Adobe can do. Maybe like you should use us too, enterprises. But I'm like, it might be easier because you weren't branded for like a decade in the market as one thing for one group of people.

10:31Harmony Anderson:Well, it's so fun. I actually, we had our first ever like go-to-market offsite in February where we did, it was just sales marketing CS, did 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 have moved into the enterprise. And Canva was an example I used. So it's like, I had four slides and Canva was like, here's where they started this year. And 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.

11:11Harmony Anderson: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 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 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.

12:00Harmony Anderson:And that requires a lot from everyone in an organization to really get there, but it's fun. It's really fun to do. I mean, that's such a different mentality to how you just explained it, because one goes like maybe the original use case of 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.

12:36Harmony Anderson: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's your top five things. And here's what you need to do and what you really need to focus on in order to be a successful leader or operator. And I look at that, I'm like, that would change my life.

13:18Harmony Anderson:I'm using Superhuman, both personally and professionally, but I have two different login instances of it. So how do we 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 I'm looking at that for all of my tools right now when chat, we have our chat GPT enterprise account. And then I've got my personal Stephanie Postles 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 have to only do in the enterprise.

13:51Like, it just it's but it's interesting, because that's how the world was for a long time. keep it so separate and you don't want people seeing your dinner recipe accidentally and chat GPT on your work account. So I think it's interesting how now people are like, no, just make my life easier and just merge things. Give me time.

14:09Harmony Anderson:It's a mindset shift. It's a habit change. And we talk about it a lot. 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, yes, but the reality of it is sometimes my kids' school reports are more important than this business meeting. I know, crazy, but I might have to do that first or respond to that email first versus this one. It's also a very personal decision.

14:44Harmony Anderson:And so I'm all about build the flexibility for how people prefer to run their lives. And then like, we shouldn't tell that to them themselves, but we should let people build it.