E25: Transitioning from Product-led to Sales-led Growth with Andrew Johnston of Superhuman

And we've had to teach the problem that email inherently sucks. Everyone has an email problem. And so I think people don't realize that it affects and can actually improve the lives and actually improve productivity for everyone in the organization if you make it better. But a lot of people just think it's an executive problem, that they get the most emails, that they're blocking people. It's actually the entire organization that has that problem.

And so much of your day-to-day is just answering goddamn emails. Hello and welcome to the Revenue Leadership Podcast by Topline. I'm your host, Kyle Norton, CRO at Owner.com, and every Wednesday we dive deep into the strategies and tactics being used to drive success by the best revenue leaders in the world. So join me as I sit down with revenue operators to discuss actionable frameworks that you can implement in your business today with no fluff, no sales pitches, and no platitudes.

This episode of the Revenue Leadership Podcast is brought to you by SurePeople. SurePeople helps teams communicate smarter with science-backed personality insights that make every interaction more effective. By understanding how people work best, teams can collaborate better, make faster decisions, and drive real results. Get free access to SurePeople's Prism self-assessment at surepeople.com. That's S-U-R-E people Now back to the show.

And I'm excited to welcome today's guest, Andrew Johnson, who is the VP of Sales at Superhuman, which is the most productive AI email application built for working professionals. Previous to Superhuman, Andrew spent 4.5 years at SendGrid and Twilio going through the SendGrid IPO, then the acquisition by Twilio, where he then became the head of all SendGrid sales. Since then, Andrew spent a year and a half at Scale AI, who's doing fascinating stuff in the AI landscape before taking this role at Superhuman almost 2 years ago. And we're going to crack into all things PLG and SLG, dig into AI and sales a little bit, talk about what Superhuman's doing there because I know you're doing some cool stuff. So excited for this one and welcome to the show, Andrew.

Thanks so much, Kyle. Looking forward to it.

So what did I miss in your background? What do you want to fill in for folks?

I don't think you missed much. It's been a really fun journey. I think before that, I spent some time at a small e-commerce startup, so it was bootstrapped. So I've seen everything from very small bootstrapped companies all the way through very large public organizations. And so that's been a fun journey. My career started in the entertainment business, so I actually was in the Like I was Lloyd, if you watched Entourage, I'm probably dating myself. I actually did that job for a few years out of school.

Oh, very cool. Or it might have been very difficult depending on how real that interpretation is. So when you're at Scale, had they started to raise like silly money yet, or was that just after?

No, they hadn't raised. So I came there when they were probably, I think we were 500, 600 people at that point when I first joined. Oh, it was that big? Wow. Wow. It was that big. Revenue was quite high. I'm not sure if I can say exactly where it was at that point, but it was quite high. And they had raised, at that point, they were at their $7 billion valuation. So they had raised pretty crazy money at that point. And then right after, right as I was leaving, they did that doubling of the valuation where they raised, I think, another billion funding up to $13 billion in evaluation. But it was a crazy time because that was right when ChatGPT launched. We actually did the early training of ChatGPT-3. And then all the other models that were out there, we did a lot of training for those models as well. So it was really interesting to be part of that early sales motion, selling into kind of these startup companies and LLMs that were building what we now are very comfortable with.

Very cool. And so other than that, you've basically been an email guy for like 9 years. So what is your obsession with email?

It was not intended. I think I got to know it because when I was at that e-commerce startup, we did a lot of outbound email. A lot of our strategy was actually setting up these deployed e-commerce shops for online publishers, and email was the common channel. So I learned a lot about that as a channel and then made sense as I transitioned into SendGrid. But email infrastructure, especially a dev tool, is a far cry from e-commerce. And so I think it was just by luck and happenstance, and then I started to fall in love with the channel. And then, you know, now it's hard to get away from it.

Yeah. Once you build your reputation as, as like a senior revenue person in a particular category like this, your, your unique value to those companies is so different than your value to like any other B2B company that it's, it's hard to unstick yourself really.

Totally. 100%.

At least there's good companies in the space. I mean, I've been a Superhuman customer for a couple of years now and It's a great product. And so it's nice to like, you know, SendGrid was a great story. Now you're in a great spot. So you're picking, you're picking some email winners along the way.

Well, thank you for being a customer. I know you, you've been a huge advocate, so it means a lot.

Yeah, I'm bad at my referral code. I'm like always just being like, dude, you got to use Superhuman. Like, what do you do? Like, you just go through your email like a, like an ancient barbarian, like clicking around and doing stuff. But I never, I never think to like send my referral code. So I think I've probably I've maybe got like 2 or 3 official referrals out of like 30 because I'm always, I'm always like berating people about email best practice. So I'm a, I am a like a super user, I would say, and an advocate. So I want to know from you, like, what are the best— you're in the company, so you got to have like really good tricks. So what are the advanced level superhuman tricks that I might not know about yet? I think we just explain to people before that, explain to people like what makes Superhuman different because they probably have no idea. I sound like a crazy person.

Yeah. The way that I sell or talk about Superhuman is imagine if you took Gmail and you redesigned it in 2025. Gmail really hasn't been touched. Sure, they've added features, they've added integrations, they've added AI now in Gemini, but they really haven't done much to that workflow. And it's still a pretty poor experience, I think. And that is even worse if you look at an Outlook. And so the way I think about it is if email were designed today, how would that look and feel? And that is Superhuman. So much more streamlined, very responsive, very intuitive, makes it easy to segment and focus on what you need to prioritize. It's really built for the modern era and we're seeing incredible results in the way that we can make working professionals operate faster, save time, all those things. And so that's what's Superhuman.

Is. The way I pitch it, I'm like, shortcuts and like shortcuts and templates everywhere. Everything you can do from a, from like one button. So I can rip through my email and like, like maybe a quarter of the time I'm just like, now trash this, move this here. Like, you know, I'll drop in a snippet because I do so many things repeatedly. Interviewing, like booking interviews or scheduling, like scheduling follow-up time. People on the podcast. Oh, it's like the— I don't even know what the button is. The squiggly button. I type in podcast, then it's like scheduling, and then it's— that's my superhuman pitch is just like snippets and hotkeys.

And I think that is the pitch. Some people get scared by that. They're like, I have to go into shortcuts. I'm used to using the mouse. But I think when you're a power user like you and I, you become so obsessed with how fast it is to move in between those things that it's second nature and it's just a huge hack.

Yeah. Okay. So what are the expert level hacks that I need to know about?

The big ones for me, some of this is just the newer functionality that we've recently launched. So a lot of folks are on the beta now. We're releasing more. But the biggest things, we just launched AI labels. So you can prompt and say all emails from Kyle go into this template, or I want to capture all things about podcasts, you can custom label an email based on a prompt. Really, really cool. And so I've built custom labels for customers, for types of customers, for my team. I built them for certain use cases, like, for example, approvals, rather than having to go into Salesforce or our approval tool, our CPQ tool, I can have them coming through my email and I can have a certain inbox that I'm triaging those. And so it kind of has even further increased my ability to just hack the whole system with email. So that's a big one for me.

So you're creating split— the inbox splits, but with a, like a natural language prompt.

Correct. That's right. So, and just for people who don't know, we'll get you access after this. For those who don't know, we have splits built in, like all of your calendar invites are split out of its own, you know, dedicated, we call them a split or its own inbox such that they remove the clutter from things that you actually have to respond to. So that's a big one. The last one I would just say. I'm just the automatic reminders and then auto drafts. Yeah, yeah, yeah. That's a huge one for me.

Yeah. Okay, nice. Yeah. Reminders is like the best because I like zero inbox. So being able to just hit like H tomorrow, H Friday and just like have everything like, okay, just like get out of my, get out of my eyes for, for a while until I can come back. That's cool.

Yeah.

All right, let's get into PLG to SLG. So, so Superhuman, you know, had a lot of notoriety for in the early days for one being like an expensive email product. People like, what, you're charging for email? It's $30 a month. Like that was sort of crazy at the time. But then customers would go through like a very curated onboarding. I think like what caught a lot of tech Twitter's attention about Superhuman success in the early days was, was like, one, it was email that you were paying for, and two, this, this like very curated onboarding process that had humans in it. Like you, you actually did an, like an onboarding call for a B2C product, which was very atypical. And now you're trying to layer on a sales motion on top of this like very prominent PLG motion. So just talk us through the journey first. Like, why did you get hired to do this thing? What was the timing and what are you trying to achieve? And then I want to get into some of the building blocks from there. Yeah.

So part of my remit was— so first of all, let's take you back to around 2021. Superhuman raised its Series C and off the heels of that had decided, let's start investigating more of a B2B motion. So started off in a very SMB, who are the customers that have 3, 4, 5, maybe even 10 seats? Can we consolidate those seats together and put them on a contract and kind of contract that revenue and then potentially expand that revenue? So that was kind of the first motion. When I was brought on, it was how do we double down on that motion but then continue to move upmarket? So larger opportunities and then even into the enterprise. And that was the core focus is how can we go unlock and what we know to be true around power users and get not only them and those 10, 15, 20 people on it, but large portions of those organizations. And we've been quite successful in doing so, but it definitely has been a journey when you think about how you go from that PLG, who's the right customer, and then how do you shift to this new buyer, multi-buyer world inside of large organizations?

So what's the hardest thing trying to go tops down now? Is it, is it the customer, the user education? Is it getting people to want to pay for email? Like what, what are the big like SLG blockers, sales-led growth blockers?

It's the— so let me back up just slightly. I think the, the key thing has been when we first made the transition, you got to know who your ICP is, right? So we first took a look at who are the buyers that are usually buying Superhuman? What do they look like? And we used a PLG tool to identify those signals and then reach out to them. So we did kind of like an outbound sales-led motion off of the ICP that we already knew. We then learned that we had to craft and iterate that ICP and that persona slightly to make sure that we were thinking about the way that that person now might bring into the org versus just themselves. So that was the biggest shift. That was the first thing, like, how do you outbound correctly to that new audience? As we've gone upmarket, what we found is we actually often inversely compared to most companies have access to very senior level people very early on because that's who's using the product. So I'll give you an example. There's a Fortune 500 company I'm talking to right now. My champion and the person that I'm on texting terms with is the COO because he's been a Superhuman user. They had 15 people on it and then their IT department blocked Superhuman and it was like he lost the second brain. He's like, I can't live without this tool. I got to go back into it. And it's great because you have instant access to that economic buyer and that champion. The hard part for us is then how do you work down and how do you convince them that the ROI and the cost of Superhuman is worth what they're paying for it as an executive? That's the hard part for us. So going from 15 to 20 to 100 users actually can be easy. Going from 100 to 75% of the organization when pitching that everyone should use Superhuman, that's hard.

And so what makes it hard in particular going from 100 to like 1,000?

People don't believe, and we've gotten better at this, and I can talk a little bit on how that Superhuman is widely applicable to everybody. They think it's a niche product, that it's the people who like keyboard shortcuts who are going to nerd out to Inbox Zero are going to get the value from it. And we've had to teach the problem that email is inherently sucks. Everyone has an email problem. And so I think people don't realize that it affects and can actually improve the lives and actually improve productivity for everyone in the organization if you make it better. But a lot of people just think it's an executive problem, that they get the most emails, that they're blocking people. It's actually the entire organization that has that problem.

And so much of your day-to-day is just answering goddamn emails. Totally.

Yeah. Especially for outbound professionals. So sales, marketing, customer success, like those organizations, typically if you get more than, I think our threshold is around 30 or 50 emails a day, you typically are a strong fit for Superhuman. That's usually around the threshold. Regardless if you're having to respond to them, if you have to just triage those inbox for knowledge, like even if you're a product manager or an engineering leader, you can be a strong fit for the product.

And so is sales, is It's sales and CS, like these are the core target functions now for the, the enterprise motion?

I would say that that is one of them. We say outbound professionals because we don't want to limit ourselves to just the sales team. But yes, outbound professionals. Yeah. People who are emailing externally for a core part of their job description is a key focus for us. Hmm.

Okay. And so are you doing any like cold net new outbound or is it always pockets of PLG users that you're trying to roll up into bigger, bigger accounts?

It is now for the enterprise side. We have started doing more of that cold outbound tactic where we take lookalike customers or find lookalike companies from places that we've won. We won a very large consulting firm, actually was written up in a Newsweek article. About how their managing directors, one of the big 4 consulting firms, their managing directors of a cohort of about 4,000 people have now access and approval to use Superhuman. And so what we're doing then is finding what are the other companies, other consulting firms that have likely similar problems, and then going outbound to those cold. And typically that method resonates quite well. So we're slightly starting to dip our toes more in that, but it's very predicated on what we've learned about PLG motion. Okay.

That makes a ton of sense. So as you're building this, this new motion from scratch, what are the building blocks? So sounds like data is, is one of them. So trying to find, find those accounts in your base. What are the other things that you had to, if you could break down sort of the components of infrastructure and capabilities that you had to build for somebody trying to add an SLG motion to a PLG team?

Yeah, I think, and thinking about this off the cuff a little bit, the biggest things are, so first one is data, right? Do you have the right data around what you're tracking? Does that data support a sales motion? Are you reaching out to customers with the right intent signal? Like, is that data correct? Is it giving you the right signal? So you've got to validate that. Probably even before that, you have to validate what is our ICP and how does it change? You're probably now not only building for the end user, but you're building for the buyer, especially as you go. So That leads me into the next thing of what does that buyer care about versus the end user and what are we going to need from a product standpoint to win over both those people? So the product today might win over Kyle Norton, who's the CRO of Owner, but it might not win over your workplace technology lead because it doesn't have standalone skin or another enterprise protocol. And so we had to think through how does the product need to develop? And then the second thing is, as we push for the product to be more collaborative and be more widely applicable to larger parts of the organization, not a siloed product, we had to think about what are the features that the product needs to have such that that's true. So you not only get value as an individual, but you get value as an organization. So ICP, data and signaling, and then product. And then the fourth one is just the team. How is the team architected? Do we have the right persona of people in seat? A PLG seller, can be very different from an SLG seller. Do we have the right customer success motion to support larger organizations in those rollouts? So you've got to fundamentally shift. And then the last part, and maybe the most important part, is does our marketing and does our messaging and positioning website where we're putting content out match the level of demand and can drive the demand such that it's saying the message so that you, Kyle Norton, say, I want to bring Superhuman to the rest of my team. I love this as a user. That has to shift because often when we first started reaching out to folks, they said, love Superhuman, but why would I bring it to my team? I've always thought of this as an individual product. It doesn't make sense for me to bring it to my team. Before we do that outreach, we've got to pre-nurture them with the messaging around, hey, the product should be thought of as a team product. It should be brought to your team. So there's a lot of marketing work that needs to go into that ICP content and positioning network as well.

I wasn't at Shopify at this time, but you could still feel the remnants even when I was there, 2019 to 2022, that people still really felt like Shopify was a mom-and-pop product, or it's like us, it's a product for small businesses. And, you know, we were, we were already winning deals with sort of the Mattels of the world and like really big enterprise customers, but Even then, the typical understanding was that it wasn't an enterprise product and they had enterprise-grade customers for like 5, 6 years. And, but those preconceptions, like they don't go away very easily. So I'd imagine you guys have had the same experience.

Very similar. Yeah, that's, I always forget that Shopify had that motion too, but it was very, very key part of their early growth. So that makes sense.

Yeah, Shopify was only product-led for years and years and years. And like, I don't think they had the Plus product until after the IPO.

Oh, wow.

And the Plus product at the beginning was like, we'll give you a CSM. That was basically the only differentiator for a while. I want to go back. So you mentioned the, so team, you know, getting the right butts in seats in a PLG seller is different than SLG seller. What are the big differences? Like what makes a great PLG seller? What makes a great SLG seller? Like what are, what are the differences there?

There's this element of being able to hunt and do more outbound, more of that like commercially minded person versus how do you lock down a customer on a contract and how do you use the signal that you're already getting? And so that person who's a really good PLG seller can grow into a role of being more of that hunter mentality that you see in an SLG motion. But oftentimes you need to bring other people to kind of create that culture. What does it look like to be a little bit more aggressive? How do we think about the buyer? How do we run a more strict, like, medic process in our sales cycle? When you're in PLG, often it's how do you unblock them and how do you make sure that it's easy to buy, easy to win, easy to bring on their team, but you're not necessarily challenging the customer to think about Hey, why don't you bring this here into our team? Are you looking at the metrics this way? It's a little bit more of that reactive. I'm not saying it's not important and being a strong PLG seller can be hard in its own right, but it's just a different, different mentality, different approach that you have to take.

What percentage of PLG sellers can make the leap versus what percentage of them should really end up in like CS or onboarding, like a different function?

I think it depends on the product you're selling. If you're in a dev tool, I actually think PLG sellers can do quite well because that approach of customer service, a little bit more friendly, a little bit less aggressive, can work really well. The catch is they have to be willing to ask hard questions. They have to really be willing to go deep and challenge that, that end customer, that developer, and then be technical enough to have the trust to do so. So PLG sellers on a dev tool looking quite well, and I saw that at SendGrid, Twilio. I think if you are in a product like Superhuman, a little bit more of a non-tech tool or a dev tool, having more like that soft sales skill that comes with being more medic-focused or methodology-focused, being able to do a little bit deeper discovery because you have to do more value selling, you have to create that pain a little bit more acutely. Is really important. And so I would say it really depends on the product, what type of company you're in. But typically I've seen PLG work well in DevTool companies kind of graduating into that portion.

Makes sense. How big was the sales team when you started versus now?

Very small. We were, gosh, 3 AEs. We had about 3 customer success reps, and then we had a team of longer tail support folks that ended up bleeding into, you know, supporting upmarket customers. And we almost doubled that motion entirely. So across the board, so, you know, now closer to about 15 total. Okay.

And did most of the first 3 AEs make— were they able to make that transition or do you need to— was it about bringing in new people for like a very new approach? How did you think about transitioning culture versus like just creating something totally new?

Great question. Most of them are still here. One individual left to take another opportunity, but most have made the transition and we've thought about different roles, whether that be inbound focused and closing, locking down deals. Some have made a transition to more of an account manager, so they're working with customers and have a little bit more of that, I'll call it like superhuman love delight. And so maybe they want to be less salesy, less aggressive in making fit really well into that nice role for upsell and expansion. And then we've had to certainly hire folks, especially in the enterprise segment, to bring some of that new energy in that we want to build inside the organization. In addition to that, we've had to hire roles like our first lead sales engineer. We've had to hire a go-to-market ops person, and then obviously some more commercially minded CSMs. And similarly, we've upleveled and tried to train the team as much as we can. I think the great part about Superhuman is everyone who's worked here loves the product, uses the product. And so it's so much harder to let go of someone who has that delight for the customer and delight for the product. I think we can train them if they're open to it versus trying to cut ties and bring some new blood in who don't have that same kind of historical just love for the product. So we've been trying to train as much as we can.

But you've had to, in order to get that hunter mentality, you had to bring in like people with that craft already.

Correct. Yeah, that's right.

Makes sense. And was it people from like— did you, did you need prior experience in the market segment or it's a fairly easy product to understand, so you just need like great sellers, more great sellers, people who really just on the motion.

I think we found sellers who have used the product in past lives do really well.

I bet.

And that is like, I wouldn't say like a key criteria, but has worked really well of people who just understand like where the product shines, where it doesn't. And then similar to you, have been their own advocates, almost like unofficial sellers out there saying, hey, I've told my buddies about Superhuman. I told the rest of my team about Superhuman. Those people do really well. So we actually look for that and screen for that.

Yeah, I need superhuman.com/Kyle Norton, and I'll just tell people to go there so I don't have to think of referral codes. Like, go to—

go here.

This is— this is my special one.

We can create your own landing page that works well. We can do that. Yeah, yeah.

Just my, like, shining face ripping through an inbox. That makes a ton of sense. And I bet there's enough sellers out there who are in the product that you could go really, really find great folks. So I wanted to go back to data. So how much of this, how much of this was internal data functionality that you needed to build? What was already there? Just talk to me about building this baseline.

It was more of a surfacing of the product than it was actually finding the data. We have an unbelievable analytics team and it's one of the great parts about coming from a B2C business is they measured everything. And so it was about two things. First, translating those into a place that we could see them. So Salesforce, we also adopted a tool called Focus. And so we leveraged that to like show those signals in a place that's easily digestible for sales. And the second piece was how do we interpret them? We have all this data, but does it mean the same thing in a B2C world as it does in the B2B world? So figuring out which signals correlate to action and Action that means like intent to buy or intent to potentially scale and expand inside of an account. So it was more of translation of the data. We were very lucky, which I think a lot of PLG companies don't have. We had all the data there. The big mistake that I often see made is like, I'm going to turn on PLG motion, go the opposite way from SLG to PLG. They want to open that up and they don't have the data. And so they're like, let's just turn it on and see what happens. And they don't really understand or have the ability to understand any of those signals and what the customers are actually telling them from the product.

Instrumenting that customer journey so that you can actually move them along. And so then the data, so do you understand the intent signals more deeply? And so does that then lead to a score in Salesforce or like what happens with Pocus? Like how does that piece of it work?

That's right. So we score them in Pocus based on, we have different, we call plays. So things that we're tracking, there are specific motions, and then we score the different leads inside of those plays. So a company has 3 or 4 individuals who are 50% plus engaged in their product month over month. They're in the top percentile of people who use reminders. There's those types of single signals, and then we can even then enrich that data. So it's also an outbound professional or the type of role that we would classify in an outbound persona. That would be a strong signal of a person that we can reach out to or a company that we might target and try to use the fodder that you have, 15, 20 seats of people who are separately using the product, and then we can use that as an engagement tactic.

Okay. And then Pocus runs those plays or then they're going into like a Salesloft Cadence? Like what's the next step?

It's the latter. So they— Pocus runs like the data intelligence piece and then you can push and build outbound campaigns from that place. You can have it all sequenced through such that it makes sense from— In Pocus? Yep, in Pocus. They connect directly to whatever outbound tool you're using, whether it be Apollo, Outreach, Salesloft, they can connect to all of them.

Okay, so Pocus is orchestrating and then it goes into a cadence. The rep sits down and how much does the rep do versus it's centrally orchestrated?

The rep is the one that is— so a couple of things. We have SDRs and reps who are running plays. So SDRs will often do like the long tail, like less nurtured, a little bit more cold or lukewarm outbound. Reps are then either doing outbound to expand accounts that they already have contracted. Or accounts that have higher intent or more senior contacts. You can one-click add them into these sequences or these plays, right? So it can be very automated. We've found, as I'm sure you've seen the theme across the board, the more manual you can get or the more personalized you can get with the message. So often we will take the data and the information from Pocus, and then rather than just pushing it through outreach, we'll actually build it out in Superhuman and send a very personalized note, or the rep will flag to me and say, hey, Andrew, I saw that the CRO Kyle Norton is using Superhuman. Here's his data. Here's his company's data around their usage. Can you send me— can you send him an email and leverage this kind of template that we've built out? So often we'll do like your shared team templates in Superhuman. Correct.

Yeah, that's smart.

Hmm, cool.

So zooming out a bit. So we've talked about these like core pillars, positioning and marketing, team, the whole product, ICP plus product, make sure you have what you need for both user and buyer, and then data.

Mm-hmm.

Any, anything else that I need, that we need to add to that framework? Is that like a pretty good—

I think those, I think those are, to keep it simple, those are like the 4 or 5 key pillars that people should think about.

And just like infrastructure. So like you've got Pocus, it's Salesforce stuff. There's probably new infrastructure to run a motion.

Yeah.

What are the, Sorry, go ahead.

No, I was just going to say, I mean, there's so many interesting tools now. Pocus is a great one. There's a lot of cool things that Clay's doing. I mean, name your tool. There's some great infrastructure that you can build, but I do think you've got to have a pretty, you know, PLG ultimately is instrumentation as you mentioned earlier. And so you've got to have a really strong opinion and very well-built-out instrumentation on that process. That's a key part too, as well. It can't just be, hey, we're going to measure one signal and try to pipe that into you know, an email cadence into a rep. It's got to be very instrumental.

Yeah, cool. So for companies that you see adding SLG to their PLG motion, what are the most common failure modes? Like, where do people go wrong?

I think the first one is not adapting the ice cream product. That's the biggest one because everything stems there. If you fail to understand who you're selling to and how that process is going to change, or if there's going to be multiple stakeholders, you're going to market to them wrong. You're going to have the wrong messaging and sales. You're not going to be able to outbound. So that's huge. And then as a follow-on too, if the product doesn't meet that understanding of that new buyer or what that company is going to need when you move into a sales-led motion from PLG, you're also going to not be able to either A, close the deal, Or B, expand the deal. And so those are probably the biggest ones that I see. And then I think the third is just making sure you have the right team and the right new culture around that team and process around that team. It fundamentally shifts. Not to say that you can't have both a PLG or PLS motion at the same time, but you've got to really think about how you're now measuring the team against goals and what that's going to look like.

Okay, that makes a lot of sense. What did you guys, what did you do at Superhuman to unlock the sales culture? Because sometimes, you know, you're in a fairly big successful company, sales is this like new thing over there. You might be working with a bunch of devs who aren't used to now salespeople playing a more prominent role. Like, how did you think about transitioning and building the culture in a right way at like a company level?

It starts with everyone from tops down at the, we call it our M team or it's our executive team being bought into, hey, we're going B2B because ultimately we can't just build for the B2C customer anymore. We've got to build for the type of company that we want to land and what that looks like. And so everyone's got to be bought into the vision of being more sales-led. That's number one. And I think with that, The best way I found to be able to do that is bring people along for the ride. So when you get into deals that are really meaningful, bring in your CTO, bring in individual engineers, make them feel and hear the pain that's coming from the customer, and also make them feel and hear the excitement from when you win a deal. That big, large consulting customer, that was a company-wide effort. That wasn't Andrew, that wasn't an individual sales rep. That was the entire company winning that deal together. And it was celebrated as such. And so I think you see this switch flip in people's minds of, oh, that's huge impact. And we could go get 10,000 customers or we could go get one large consulting client and that the impact of that is the same, but the stickiness of the product, the customer feedback that you get, all of those things just amplify when you get a very large deal. And so yeah, bringing people along for that ride as well as being bought in to that motion was very, very key. I think that's the big one. And then you can get down to the tactical around how do you change, like, you implement things like medic or again, a methodology such that there's this new repetition and expectation that I'm setting, the team is setting with the new sellers that are in seat around how we operate moving forward versus a little bit of a different, more laid back culture like PLG motion from a sales perspective, at least.

That makes a ton of sense. It's interesting, like sales is such a rush and it's so fun that even if you're like a PM or an eng and like you've never thought about sales, you can, if those people are involved tangentially and are involved in a win, like no matter who you are, that feels fun. You know, like we're, we've had some product folks involved in deals and saves and stuff here. And like, I totally agree. The best way to get people invested in is, is like, you know, give them the bug, you know, give them the, the, that sales bug, give them a taste and like, you know, make sure that they feel part of the recognition and the, you know, the, the vibe because it's, it's, uh, it's only natural to gravitate towards that. Totally.

We've even done— I mean, this is probably common, but we give— like, I give my other executive team members quotas. You know, like, I have my head of finance. Like, I'll say, like, hey, I have $100,000 in your head or $50,000. Like, I want pipeline from you, you know, based on you introing us to, you know, vendors that we might sell them to. Right. And that's one way. And then I think to your point, if you bring those product leaders or those engineers into calls, Oftentimes they'll go back and think about that call with the customer and then develop a solution and they'll bring to us. They're like, this totally changed their game from being internal only to now having this external piece, which is addicting to a certain extent. We get that all day being in sales and we take it for granted, but people who are internally focused don't get that customer thing that we're building for on a day-to-day basis, which is, again, super invigorating across the board.

Awesome. So let's transition to AI in go-to-market. And so there's a bunch of AI built into the Superhuman product. AI replies is something that I use a bunch, and it's actually since the beta that I was in a while ago has gotten like so much better and it's started to really like sound like me more and more. But where are you using AI in go-to-market today, if anywhere?

We're using it quite a bit. So we've adopted a fair number of tools. I mean, The cool part about building sales inside of a relatively established org that's somewhat large and kind of being like a Series A startup inside of the Series C company is I can build like a Series A startup. I don't have to go to the old traditional model of hiring a bunch of reps. And so we've tried to automate what we can. So we obviously are using kind of the Superhuman suite. We are using things like Gong and adapting into automated Salesforce enrichment, automated Salesforce field management, things like that to help the AEs focus on selling their time. We also have a tool that helps us with RFPs. So we've got an SE can turn our turnaround time on RFPs is almost less than 24 hours for 250 questionnaires that we get from large organizations. We only really have one person in that role.

And so, like, that's such a no-brainer. Yeah, such an easy one.

Easy one. And then so we try to implement everywhere. And then even personally, I encourage people and we use Claude at the company level as well as ChatGPT. I encourage everyone to get a license and using the pro version. Personally, I've built like an Andrew interview GPT so I can gut check myself and I can upload transcripts into that and it helps them with hiring. It makes sure that I'm being unbiased. And so there's all these little hacks outside of the tools that you can go buy, again, like the Clays, like the Gongs that do a great job, but just using the LLMs out there to really explore and build and automate some of your own workflows. And we try to do that as much as we can at Superhuman.

So you're using Gong for CRM enrichment or another tool?

We're using Gong. We also just explored another tool called Wiser, which we're implementing right now. Oh, and I know Corey. Okay. Corey is a friend of mine as well. And we looked at a couple of tools and we thought he was a great option. So we just are implementing that right now. So yeah, we're using Gong, but we didn't feel like Gong was hitting all the benchmarks that we need to.

I just yanked out Gong a couple of months ago because it was just so expensive. And we're doing it through Momentum, which is similar-ish. CRM enrichment, but they have a call recording tool now. Obviously it's like not feature parity to Gong today, but for like a fraction of the cost and to consolidate just in one vendor, we took the plunge pretty early. Yeah, that's, that's like probably one of the first places I would tell people to start is like CRM enrichment because AI does such a good job with it. It's, it's pretty low stakes, really high value from a productivity perspective.

Totally. That's a big one. The other tool, if you've heard of a company called Cinch, we're doing like automated Cinch or withcinch.io, I think it's the website.

Supercharging sales, is that it?

Let me just make sure I'm looking withcinch.com. Excuse me. And it's spelled S-Y-N-C-H. Yes, you're on the right page. Yeah. So it's a forecasting tool. I didn't like the native forecasting in Gong either. And so, yeah, so this is the most—

I don't mean to beat up on them.

I know. Great call tool, not a great anything else. And we use them to do forecasting, but also they have AI-built natural language reports. So you can say, Show me a report with this sort of thing. It's greatly increased our productivity of our single RevOps person as well. So that's another area like the SE use case that is super helpful to have an AI tool built in.

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Very cool. And the seed round led by Jock Altman, who's on our board, who I know well. So there you go. Small world. Um, and so what skills do you think a rep really needs to triple down on in an age of AI? So like the world of selling will likely change a lot in the next 3 to 5 years. What does that mean for the rep in your mind?

In my mind, it's two games. First is you have to be really good at the soft skills because the AI can't yet replace that. And so you have to really know how to be persuasive with customers. You have to know how to take feedback. You have to know how to ask the right discovery questions, do your homework, track test those things, do the mock mock calls with your team. I think that's really important. Learn those skills. And then I think the second piece is most teams are going to operate with less things or less supporting functions. You've got to be a builder, so you've got to learn how to build and leverage the tools that are either accessed at your company or you go request access to them such that you can build workflows that make you supercharged, whether that be helping you automate outbound and pipeline gen, whether that be automating follow-ups, it could be anything. But I think you've got to be willing to build your workflows in AI and understand and know those tools. But I think really getting good at the soft skills is going to set you apart because you can't just be mediocre anymore. You've got to be really good.

Yeah, I was thinking about this the other week. It's like, man, I would kill to be a rep right now in a company, in a company that has like, you know, some AI in go-to-market, but not a lot because I would be in there like building clay tables and running my own automations and going completely rogue. And there's just so much opportunity at an individual level. We're doing most of it top-down, like building, building a bunch of the stuff. We're SMB, so it's, it's a slightly different, slightly different environment. But you look at some of the, what people are building on, on Twitter or LinkedIn and some of those automations, I'm like, man, I would be using Operator to like do a bunch of stuff. It's wild.

Actually, I have to ask, what are your favorite tools right now? I know Operator, I haven't used it, but I've heard good things about it. But what do you kind of have in your stack right now that you're really liking?

Like, Operator is not that functional. It's really fun to use and you could do some low-stakes stuff like research and have it crawl websites and do certain things. I use deep research all the time, constantly on ChatGPT. Yeah. So, so I, I use ChatGPT for problem solving when I'm thinking through a problem. Like if I need to, to write, like I'm writing a proposal for something right now. And so I, I use SuperWhisper to just like talk as like a dictation app. So I'll just like use SuperWhisper, yammer away into O1 Pro and deep research and like talk about my problem. Like go research all of the people who have solved this problem, the experts in the field, bring back that research and then format it into whatever I want, like a proposal, like a a plan with like these work streams, but tell me what work streams I'm missing. So like the problem solving and synthesis I use ChatGPT for, and I find myself using Deep Research like constantly now. Cool. And then Claude I use for writing. So I've got a bunch of writing projects in there. So it's got— so I've taken a bunch of stuff I've written, I've gotten it to like describe my writing style in a whole bunch of detail. And so I can now, uh, when I record the podcast, I'll take the transcript, put the transcript into my newsletter writer, which is built on a bunch of stuff that I've already written, and it will just like crank out a really good, like a really good version, like a version where I'll do a 20 to 30 minute edit on it. And I look at it, I'm like, this is like a 4-hour piece of writing and it took me 30 minutes. And it's funny, I get asked, people jokingly ask me like, how do you have time for all this? Like podcasts and company and all this stuff. And I would jokingly say it's like, I don't know, I just like work a lot because I do. But I really think, I really don't think I could do the podcast and write the newsletter and like keep doing LinkedIn content without some of these workflows. And I have stuff for like any little thing that I do a lot. I find I'm like, oh, I should just like, I'll spend 20 minutes, do this meta prompting process where like I'll tell the AI to build the prompt for me and then I'll put that into either a Claude project or a custom GPT. Actually, I'm, I've stopped using custom GPTs. I just use, um, projects now in, uh, in OpenAI because it takes all that into the context window. I just, custom GPTs don't work well for some reason. Like the, my output of just a normal chat is better than an output of a custom GPT for some bizarre reason. I don't know. I don't know. Maybe somebody can tell me if you're listening. Um, yeah. So like that type of stuff.

That's cool. Um, I, I just did my first deep research. I was like late to the game. I use ChatGPT a lot, but I had not done a deep research. Prompt yet, and I was blown away. So definitely be using that more.

Yeah. So like, I'll give you a funny example because it's just my default now. I'm like, you know, my hair has been receding now for a couple of years and you get—

yeah, yeah, yeah.

And so you get pinged with like all— like the internet's full of like, oh, it's this miracle thing. You got to do the little, little spiky roller or it's a topical. You got to take this pill. And I'm like, just go tell me, I was like, do it. I did a deep research thing. I'm just like, tell me what are the most science-based non-pharmacological interventions for hair loss. And it's in my— I have a health folder in ChatGPT that has like my Oura Ring data and like a health dossier. And I told it to like ask me a bunch of questions, like ask me as many questions as you need to understand my health profile to then give me like tailored answers. So this is a chat in my health project in ChatGPT and the, like, the, the, like, the feedback is just so clarifying because you're like, okay, now these are the research papers with, like, clinically proven results. And it's basically none of the crap that people are, like, trying to shove, shove to you through Instagram ads. And so I just find this is my default now. Like, I just default to chat, to deep research for most things that, like, I really want to know. A lot about with like a level of precision. Uh, I built a gambling GP— I built like a gambling one, which is pretty funny, with GPT and O1 Pro— with, um, Deep Research and O1 Pro— that was on a heater for like the— for a while. It's still like pretty good, but like it was, it was like hitting it like 80% correct for a while. So it's— I don't know, I'm obsessed. Um, okay. I want to ask a couple, one more question before we get into the quickfire. So I think like one of the, one of my concerns with AI tools is so much of the output is like really generic and it has bot breath. Like you can tell it was written by AI. And when somebody sends me like an AI, very clearly AI generated email, I'm sort of offended by it. Because it's just like, it's like, ah, you didn't even take the effort to like research me or do anything. And so I use Superhuman AI, the AI response a lot for like low stakes stuff, things where I'm like not that interested or it's like not something super important. And it's great for that. But I haven't quite gotten, I haven't graduated to like responding to to higher stakes things with AI written. And so how do you think about blending the two and getting people to really leverage, like, how do you get your sales team to use your AI tooling while also sounding personal and, but in being able to get it at scale?

Yeah, it's a good question. I think, I'm excited to get you in the beta. From Superhuman, just real quick, I think it's gotten better as we now auto-draft every reminder email you have, we'll auto-draft a response, which has been really helpful in that the response is a little bit better because it's using the context from the thread. So it's improved. So I would say things like that. What I tell my team is leverage the AI, but then put your filter on. Don't just click fire, send. It's not going to work. You know the customer, do your research, do all the things that you do to be a good AE. In fact, if you're leveraging AI the right way, it's going to give you more time to do that. So what I typically say is leverage the tools. It's going to make you operate faster. I mean, you and I probably both know that if you can have it create a thing and then have to just edit, it's going to be faster than wanting to type the whole thing out and make 3 or 4 versions. And so that's what I try to do is blend between being a filter and editor, but still using the tool. The other thing is, I think the more that you can get really good at prompting, which sounds like you've gotten masterfully at, and teaching my team to spend time working on that, the better the output's going to be. And knowing what are the things that you can prompt that's going to give you the type of output that you want. And then the editing becomes less and you can add in that piece of really powerful personalization of content it's going to matter. Another tool that I love, just like throwing out, is called Whisperflow, which is basically dictation. And then it will—

it's like Super Whisper.

Yeah, it's awesome. But what I've done is, or I've told my team, dictate up front using that into ChatGPT. So spend like 3, 4, or 5 minutes just dictating entire prompts of what you want. And then you can even add in research bullets that you've collected, things that you've learned about a customer. The output is way better, and then you can use that and put that into an email. So there's a lot of ways that I think finding the tools and melding your deep research with the customer, with how the tools are helping create the content, you can get to a really good place that doesn't sound just robotic.

Yeah. One thing that I would love to have in Superhuman is to be able to tune tune the AI response to specific things. Like, I want to say, it's like, hey, if there's ever a scheduling thing, CC my admin, CC Viviana, and defer scheduling to her. Because I'll get a thing, hey, grab some time, and I want to cram into the context window every time the superhuman drafts a response to be like, hey, default to this or default to that, or like be a little less formal. Like the, that, that's the thing I wish I could tune a little bit more or like feed it more of my own writing intentionally to be like, like tune it in this way. That's a part of scale.

We, um, we're thinking about a couple of different things. You know, none of these are product commitments. Um, so one is just saying that out loud. So Laura on our product team doesn't kill me, but, um, One of them is bring your own AI. So if you have ChatGPT for your business, you can plug that into our Ask AI feature functionality, and it will leverage that context through your business or whatever you've written before and use that in terms of responses. That's an interesting one. Kind of difficult, but there's a lot of things there. The other one is the ability, what you just said, of fine-tune responses. So I have one that I found, like, if I write something and then I change the message and I say improve, keep casual, it kind of nails the tonality that I want. But that prompt is not available. I have to type it each time. So being able to have a saved prompt that you could tune. And the last one that Rahul, I think, has talked about in a few places is workflows, which is exactly what you're talking about. If I get an email from a candidate or a recruiting email, automatically CC this person, and it builds out an AI-built workflow. So it knows the type of email based on natural language. That's a big one that probably will be built this year. Just timing is the web.

Yeah, I do that with snippets now. Like the one, like if it's a, I've got like a vendor one, a partner one, an interview one, uh, like a personal one. And I just hit the squiggly, like, what is it? The semicolon. I hit like semicolon and then the, the like semicolon partners. And then it's just like the partner scheduling thing as CCs Viviana. But like, I want, I just wish that could be baked into the AI. I feel like that's probably coming from— if anybody's going to figure out, it's you guys.

I'll relay that feedback. I think you're not alone there. There's a lot of people that want very similar things. So, but I'll make sure the product team gets that. That's a good one.

Yeah. This is a podcast/product feedback.

We love— I love it. It's great.

Yeah. There's so much opportunity, I think, in this space. It's really cool. This is why I think folks should be thinking about an email tool like this because you can just, as long as you put in the effort to like tune things how you like it, you can, you can fly.

Yeah.

Okay.

It is, it's become my second brain. It's my last plug is it literally is my second brain. I couldn't, I couldn't live without it.

So, yeah, I feel the same way. Um, all right. Quickfire round. Uh, what do you think separates a good sales leader from a great one?

I think no matter the size of the business and the organization, you have to be willing to get your hands dirty. If you can't go in and be called in to sell a deal or help a rep sell a deal, I don't care if you're CRO of Snowflake or you're at Superhuman, you've got to be able to drive a deal forward and be willing to get your hands dirty and be willing to engage in that way. You can't just farm everything out. Like, at the end of the day, this is still an art, and being able to be like that thought leader and that like go-to person, I think is really important. I think you build a couple of things, a lot of trust with your core group of reps, right? Hey, Andrew actually knows how to sell. He actually takes the time to learn the product and knows how to position it such that I can bring him in. And if he can do it, there's a way that we can learn how to do it too. I think it just builds a ton of trust in the team. So I think that's a big one.

Yeah. What's the most common advice you find yourself giving to mentees, like first-line managers that are figuring out— what do you find the advice is you most frequently give?

I think a lot of sales reps who transition into a leadership role, it's hard for them to go from individual quota attainment and how do I operate in a very narrow-focused view to how do I think about both my team that I'm now managing, my own quota, but also what's good for the company and the customer. And so the feedback I often get is raise your altitude a little bit more and think about when I'm answering a question or making a strategic decision, you can make a strategic decision that has a short-term impact that's negative for your team, but could be the long-term benefit of things to move forward in the right direction. And so you've got to be able to take your step, take your place out of it from just quota achievement, your own quota. And that's hard to do.

100%. What's the hardest lesson you've had to learn?

I think it's just to go slow. Go slow to go fast, which I think you, again, coming from being a seller and going through the ranks of mid-market enterprise, you operate of how do I keep things moving forward? How do I have constant pressure? And sometimes, especially as you then graduate into leadership, you have to see the whole playing field and make sure you take time to sit back and go slow and make a very informed decision versus a fast one. And I think that's a big one that I've had to learn because I've made those— I've made one-way door decisions by accident when I thought it was a two-way door. And it's very hard to do.

Yeah, that'll get you. What's the best thing you've read in the last 12 months?

There's a book called Super Communicators by Charles Duhigg.

I just finished it.

Yeah, I finished it not too long ago. We just had our SKO and I presented on it at our SKO and I just thought it was— some of it's obvious, but I think it's told in a way that really resonates.

Yeah, I think so too. It was great. A lot of good takeaways, good reminders. It was solid. Well, Andrew, this was great. I think this is going to be really helpful to folks as they think about layering in this SLG, SLG motion. I think that, that framework is really helpful about how do you transition the team, how do you think about ICP and product infrastructure, the data and tech. So tons of really actionable insights for folks. Appreciate you joining. If people want more from you, where should they go?

You can find me at andrew.johnson@superhuman.com or hit me up on LinkedIn. I'm responsive to both. Okay, cool.

Appreciate it. And yeah, thank you for taking my product feedback.

Thank you, Kyle, for being such a super fan. I really appreciate it. Thanks for the time. Yeah, for sure.

Thank you for listening to the Revenue Leadership Podcast. If you enjoyed it, don't forget to subscribe, and you can find a link in the show notes. And be sure to leave a 5-star review, share it with your network, and please join me next Wednesday for another great conversation.