Prepare to Sell to Enterprises After Finding Product-Market Fit, with Superhuman CEO Rahul Vohra

In this episode, WorkOS CEO Michael Grinich and Superhuman CEO Rahul Vohra cover what happens after a company finds product-market fit: getting Enterprise Ready. They also talk about when to hire a sales team, how to scale up high touch onboarding, and the philosophy driving a product that hundreds of thousands of people are on a waitlist for.


Michael Grinich (00:02):
Welcome to Crossing the Enterprise Chasm, a podcast about software startups and their journey moving upmarket to serving enterprise customers. I'm your host, Michael Grinich. I'm the founder of WorkOS, which is a platform that helps developers quickly ship common enterprise features like single sign on. On this podcast cast you'll hear directly from founders, product leaders and early stage operators who have navigated building great products for enterprise customers. In every episode, you'll find strategies, tactics and real world advice for ways to make your app enterprise ready and take your business to the next level.

Michael Grinich (00:39):
Today I'm joined by Rahul Vohra, the founder and CEO of Superhuman. For those of you unfamiliar, Superhuman is building the fastest email experience ever made. In April of 2021, Superhuman was reported to have over 20,000 users with a wait list over 10 times as long. In August Superhuman raised $75 million in Series C financing and I'm super excited to chat with Rahul about how Superhuman is getting enterprise ready and crossing the enterprise chasm. Rahul, welcome to the podcast.

Rahul Vohra (01:07):
Hey, and thank you for having me.

Michael Grinich (01:09):
So let's kick off by giving us a quick update on Superhuman. Where's the business and team today, and what's your current focus?

Rahul Vohra (01:16):
Well, I would say that our biggest accomplishment is that our customers are now getting through their inbox of about twice as fast as before and many of them see inbox zero for the first time in years. By the numbers, folks have sent more than a hundred million messages. They've triaged more than 350 million conversations and they've used, and this is an odd metric for a company, but they've used over a billion keyboard shortcuts. And we know from those cut alone that they've saved tens of millions of hours and when you zoom out to everything else that Superhuman does, over a hundred million hours.

Michael Grinich (01:50):
That's pretty incredible. I mean, in just a few years having that kind of adoption and time savings for people across the whole world. A few weeks ago, I believe your co-founder Vivek tweeted about an upcoming feature called Superhuman for Teams. I was wondering if you could walk through that and why you decided to build it?

Rahul Vohra (02:07):
Of course. We've since renamed this to be Superhuman for Business, which is Superhuman, but packaged and positioned for businesses. So why did we build it? Well because in today's world, the fastest organizations win. And we found that teams that use Superhuman, they move faster, they become more responsive and they end up feeling less stressed. Now, historically there was no easy way for companies to buy Superhuman. In fact, I would go so far as to say it was hard. So we're making Superhuman for Business.

Michael Grinich (02:39):
So lots of these products, similar to Superhuman start off with sort of a single player mode. Individuals can adopt it, sign up, get started and you move to having teams in multiplayer. I'm curious if you can talk about what you think is different about multiplayer, what features startups should prioritize, how Superhuman is thinking about this and maybe what you look to for inspiration as well.

Rahul Vohra (03:01):
I would say that we took a very unusual path into multiplayer. We took the time to really hone and polish the single player experience first. It took many years, and this was because of a philosophical belief, a belief that we had from day one, which is we want to make the kind of software that you want to use because you love it, not the kind of software that you have to use because it's what your team uses or because your manager says so. That said, multiplayer brings a whole host of added complexity, roles and permissions, administrative consoles, provisioning, de-provisioning and that's before you get into the actual multiplayer features themselves. So I would say it's not something to be taken lightly at all.

Rahul Vohra (03:47):
In terms of who we look to for inspiration, I would say in technology, Figma and Notion are both very impressive. For me they're great examples of combining the value propositions of single player and multiplayer, which when you do it right, can unlock very rapid revenue growth.

Michael Grinich (04:05):
It's been incredible to see how fast those companies have grown as well from the revenue side, starting off with smaller teams or smaller groups using it within companies and spreading out from there, eventually taking over the whole organization in a way. Do you see this happening with Superhuman? I know you're not fully multiplayer yet. We haven't released Superhuman for Business, but do you see that kind of adoption? How does it spread within teams?

Rahul Vohra (04:29):
We do see very rapid adoption within teams. It's primarily through word of mouth and through making people happy. It isn't the case that the there's a particular piece of data inside a Superhuman that colleagues need. It really genuinely is, we're helping people save three hours per week. And if you are the kind of person that does a lot of email and for whom that time is valuable, you'll end up talking about this. It turns out that one of the topics that people love to talk about, and this works very much in our favor, are their latest productivity tips and tricks, their hacks, how it is they're becoming really great at what they do and so naturally Superhuman ends up being a topic of conversation.

Michael Grinich (05:12):
Earlier this year, you folks hired your Head of Revenue and I wanted to unpack that, as you're looking to expand the financial side of the house. When did you know it was the right time to make that hire? What went into that thinking? What was sales process like before then? And what did you look for in that hire?

Rahul Vohra (05:29):
It was a few things that went into knowing it was the right time. The onboarding team was reaching a size where we would benefit from a seasoned leader who had seen this level of scale before, someone who could take us to the next level. I would say, number two, we were getting a lot of market pull from businesses, either directly, they were reaching out to us and saying that they wanted to buy, or indirectly where we were organically acquiring lots of individual seats. We recently estimated that about half of all Superhuman seats are either expensed or paid for directly by businesses. And I would say, thirdly, we wanted to create new go-to market motions at Superhuman. Now one motion is to consolidate existing individual accounts into a centralized contract and then of course, growing those accounts. Another motion is to attract new organizations where we don't have any existing seats.

Rahul Vohra (06:26):
And I think therein lies the answer to your other question, which is what kind of person did we want to bring on. We wanted to bring on the kind of person who we be equally at home hunting new logos as they would be growing accounts. So someone for whom sales is just as within reach and expert as success. But also someone who can actually run the whole end to end life cycle. We ended up moving what we call our delights organization, which in other companies might be called customer support, although in the case of Superhuman, they have the remit to go above and beyond, we ended up moving that organization into the revenue and customers organization also. So this team now has multiple sub-teams, each of which represent a portion of the customer life cycle. It is the onboarding team, which is relatively well known, it's the delight team, which is also well known, but it also has new teams that were just spinning up, customer success, sales, and account management.

Michael Grinich (07:29):
That's a pattern I've seen with actually a lot of different companies where the onboarding customer success aspect isn't pulled away from the sales team or pulled away from the revenue focused team members, it's sort of under one umbrella. I've seen this at Figma and I think Dropbox did this early on as well. What's the current focus of your sales team? How are you thinking about that go-to-market motion for sales and what is the sales team focused on today?

Rahul Vohra (07:53):
We aren't yet doing new logo sales to the extent that we're doing sales, that almost always companies where we have an executive sponsor and they're interested, I mean, they're usually super fans of Superhuman and they're interested in spreading Superhuman to the rest of their team or indeed to the rest of their company. A plan that has worked well for us so far and I should add that we're in the earliest innings, are that we meet with the executive sponsor, we have a conversation with them and share that we'd love more seats of Superhuman at the company. They're usually excited by the prospect, because they love the product so much. And then we experiment with an all company or an all team demo.

Rahul Vohra (08:38):
So there was a recent company, I would say there are about 300 employees in total. We ran a webinar essentially, a demo, where one of our sales people who used to be an onboarding specialist and our head of revenue attended from the Superhuman side. And we demonstrated Superhuman showing off the best of its capabilities and really making it clear how it would save you three hours a week. Now about 70 people attended that demo of the 300, so pretty high turnout. Superhuman has a good brand name, which we're able to leverage in these conversations.

Rahul Vohra (09:15):
And then from there, they were then able to book onboarding sessions, which I think listeners of this podcast would know well from Superhuman, but essentially it's a one-to-one, 30 minute onboarding call with one of our onboarding specialists. And so I find this really interesting because it's a extension of our classic strategy, which is one to one onboarding. We're definitely not giving that up. We know it's magic. We know it's rare and we know it works, but it's adding process around it. And in this case, two steps prior, number one, identifying an executive sponsor with whom to work and number two, having them hosting an all hands meeting where people can turn up and see the value of Superhuman as demonstrated by an expert salesperson.

Michael Grinich (09:58):
And are those deals all coming inbound, that executive sponsor, are you doing outbound traditional sales going after them? Where does the new business come from?

Rahul Vohra (10:06):
It's a little bit of both. We have a constant stream of people saying, Hey, I love Superhuman. I'd really like to buy it for my team or company. How do we make that happen? We used to say, sorry, we're not ready to do that. But now that we have the team and personnel increasingly in place, we now say, that's fantastic. Let's have a conversation. Let's figure this out. Let's design an implementation plan.

Rahul Vohra (10:29):
Part of it also is reaching out to people who've expressed that in the past or just companies where we have a lot of penetration, where we're able to say, Hey, by the way, it looks like you have 50 seats. Everyone's paying by themselves. That surely is an administrative burden, it sounds like an expense overhead. Why don't we get this all consolidated? Why don't we make it really easy to buy? And why don't we work together on unlocking productivity for your team? So far, everyone's been really excited to actually work with us to unlock the next level of productivity.

Michael Grinich (11:00):
You said something earlier. I wanted to go back to, where you said one of your salespeople started off in your delight organization, I believe the onboarding organization. Talk with me more about that. Why do you think they made that transition? Is this common at the company? Why do you think that there was a good transfer of skills there?

Rahul Vohra (11:18):
We deliberately hired a very diverse set of people for the onboarding team. Some of them, like this individual, came from a traditional account executive background. This person is Ryan. I believe they had two plus years of AE experience, actually, if not more. We've also had really good success hiring out of hospitality, out of food and beverage. That team is an incredibly diverse team. As a result, when people have been in the role for a number of years, they understand the product really well. They've onboarded one, 2000,3000 customers. They then have the context and the knowledge to start to integrate that into potentially a different role. So we've had one person jump from onboarding into account management. We've had two more people jump from onboarding into customer success. And again, some of those folks actually had professional customer success background previously.

Rahul Vohra (12:17):
So I would say the interesting lesson here, and this has worked out well for us, is if you are considering building an onboarding team, staff it diversely. So a whole variety of different people, trainers, people from sales, people from success, people from account management, because you will eventually have all of these functions. And you might just then find that the best people for the jobs are the people who've been doing an adjacent job already for years.

Michael Grinich (12:43):
And I guess at that point, they're super familiar with the product also, nice benefit of them having grown up there.

Rahul Vohra (12:48):
Absolutely. And you know, in this case, being able to do a demo that just is natural. They've been demoing it to thousands of customers. So it's a very easy thing to be able to then extend that into demoing it to a whole company or a whole organization.

Michael Grinich (13:05):
So speaking of entire companies and entire organizations, I know that Superhuman right now isn't really going after the enterprise yet, but I'm curious if you break down maybe what have been your first bigger opportunities that came inbound, like the first enterprise potential that you're seeing. When were those? What did you see? Was that earlier on? When did you start having the conviction that, we actually think we can go up market and serve these customers.

Rahul Vohra (13:31):
I would say it did start to happen really early on. One of the great things about building a horizontal tool, indeed, one of the great things about building a single player tool, there are not that many advantages, but there is one very big one, which is any individual person can start using it without convincing anybody else. And that's kind of remarkable. That means that at every single tech company that you can imagine and a significant percentage of Fortune 500 and Fortune 1000, we have Superhuman seats. And in some of those, we have many Superhuman seats. Now I would say we are some ways off from being true enterprise. What we're really doing right now is focusing on growing the seats in the segments of the market that are probably more accurately SMB and mid-market. But that's mostly enterprise readiness, which of course you guys are all about, having all of the things that an enterprise buyer would expect and we're not quite there yet.

Rahul Vohra (14:35):
What we're working on right now is the fundamental value proposition. It's basic things like an administrative console. Would you believe that today there's no way to remove somebody from a Superhuman team? Sounds ridiculous, but it's true. And that's just because we've been so focused on building the actual core experience itself. So we're coming around again, we're building all of these basic things and I do think that's going to unlock a lot of potential with SMB, with mid markets and eventually enterprise.

Rahul Vohra (15:04):
The other part of your question was why do we have conviction? Well, people are knocking on our door trying to buy this today and we're just not ready. So the best possible place to be in, we have product market fit. People want this for their teams and now we just need to go and unlock all of that.

Michael Grinich (15:23):
So it sounds like it's early, you're going through this process of becoming enterprise ready. Have you had pushback from customers not having these features or security concerns or just generally the things that maybe enterprise organizations typically will ask for? I'm curious what your experience has been selling into those organizations without those features today.

Rahul Vohra (15:43):
Security only comes up in so far as people want to understand architecture and read a white paper. That seems like a very reasonable ask. And they're almost always pleasantly surprised about how thoughtful and careful we've been on that topic. I would say apart from that, one of the main themes has been user provisioning and de-provisioning. A lot of our potential customers, themselves being technology companies, are quite sophisticated. So they're using either Okta or Rippling to provision and de-provision, and what we're seeing is past scale. So let's say you are no longer SMB or mid-market, there is just this desire to have absolutely everything automated. Think of a company where maybe a hundred people are joining every month and maybe 20 people are leaving every month. That would be a lot of provisioning and de-provisioning to do. And so that's probably the biggest feature request that we've had from true enterprise customers, is to make sure that our skim integrations are working well.

Michael Grinich (16:45):
Are there other directory systems that you are asked to tie into? I know today Superhuman doesn't support Exchange I think, or Office 365. I'm curious if there's a pull into that and a pull into other maybe directory or IT systems today.

Rahul Vohra (16:58):
Oh my gosh, huge pull. Today from our current customers, we have to remember they're G Suite only. And so the Microsoft ecosystem doesn't even figure in their minds, they're all using Rippling or Okta or they may even be still doing it manually. That said, our biggest feature request for Superhuman in general is support for Office 365. And I would not be surprised that when we do that, that then the biggest integration request becomes any of the Microsoft directory systems, because these companies, if anything are actually larger and the desire to not manually provision, de-provision will be even greater.

Michael Grinich (17:39):
Can you talk a little bit about the choice not to work with the Microsoft ecosystem initially? I know Superhuman's Google Workspace, G suite, Gmail only today. Do you think that was the right decision, not integrating with Exchange and not supporting those users? Looking back, what would you say?

Rahul Vohra (17:56):
I would say that we made this choice, because our key features are speed, design and quality. Superhuman is the fastest email experience in the world and people expect a very high degree of polish. Now, one of the best ways to unlock speed from an engineering perspective is to code directly against the platform. One of the reasons why Superhuman for Gmail is so fast is because we coded against very specific idiosyncrasies of the Gmail APIs. In other words, we do things that most Gmail clients would not do, because the techniques are very, very specific to the API. We're now repeating that playbook with O-365, we're coding directly against the Office APIs and doing things that most email clients would not do. But as a result, Superhuman for O-365 will be blazingly fast, much faster than any normally constructed email client.

Rahul Vohra (18:47):
So was it the right to choice? I would say yes, I think so. It's very hard to build a 10X better product, so you want every possible advantage in doing so. And for us, the ability to focus on one platform has let us built something special. And I'm not sure that we could have done that if we spread our efforts.

Michael Grinich (19:06):
I think you've described Superhuman as like a prosumer piece tooling, a prosumer product, and you have a higher price point at that rather than something that's a commodity consumer product, $30 a month, rather than maybe just a few dollars a month. Can you talk about this a little bit more? How you think about the prosumerization of the enterprise?

Rahul Vohra (19:26):
Sure. So as an industry, we first saw the consumerization of the enterprise and I think we're all very familiar with that. As consumer software has become increasingly polished and delightful, we then came to expect the same of our business software. But I think we're now at the start of a new wave, the prosumerization of the enterprise. It does not matter whether you are a CEO, an executive, a manager, prosumer needs have been ignored for years. And yet there are tens of millions of prosumers out there waiting to buy software and they're willing to pay a premium for the best in class software. That's why folks pay $30 a month for Superhuman.

Rahul Vohra (20:07):
I think another interesting lens is, why now? Why is prosumer a thing that is happening today, but didn't happen previously? And I would say that historically it's been super expensive to play in this space. Let's say you wanted to build a new email client or a new browser, to do it well and to survive for the most part, you really had to be a multi-billion dollar tech come like Microsoft or Apple or Google. But now thanks to better APIs, better developer tools and better distribution channels, a startup like Superhuman can actually play in the space.

Michael Grinich (20:43):
So before we wrap up, got a couple more questions. Zooming out, this is your second company. You're a serial entrepreneur. What's the most important thing you've done differently at Superhuman than you didn't do with your previous startup.

Rahul Vohra (20:56):
We charged from day one. For those that don't know, Rapportive was one of the first Gmail plugins to get to millions of users. It became a beloved tool like health classic. It survived for 10 years, but the one thing we never did is charge for the product. With Superhuman we've held ourselves to the bar of building something that people would pay for and rave about right from day one.

Michael Grinich (21:19):
And maybe to dovetail into that, if you were to give advice to somebody say working on a B2B SAS product, a founder looking at going upmarket and growing, what advice would you give? What would you tell them they should focus on?

Rahul Vohra (21:32):
There is this very palpable shift from pre-products market fit to post-products market fit. And I think as I reflect and I look back on how we could have done things differently with Superhuman, one thing I would've done is just press down the pedal a little harder, pour more gas on the fire as we went through that transition. Now of course I'm able to say this with the benefit of hindsight and things always seem different when you are in the thick of it. But I think we could have done better and moved faster still with a larger engineering product and design team along the way. But as they say, hindsight is 20-20.

Michael Grinich (22:11):
Well, I know Superhuman continue to grow and you guys have a full roadmap for product ahead, so we'll be very, very excited to keep watching. Thanks so much for joining the podcast. I really appreciate your time.

Rahul Vohra (22:22):
Thank you Michael, for having me today.

Michael Grinich (22:29):
You just listened to Crossing the Enterprise Chasm, a podcast about software startups and their journey moving upmarket to serving enterprise customers. Want to learn more about becoming enterprise ready? The WorkOS blog is full of tons of articles and guides outlining best practices for adding features like single sign on, skim provisioning and more to your app. Also, make sure to subscribe to this podcast, so you're first to hear about new episodes with more founders and product leads of fast growing startups. I'm Michael Grinich, founder of WorkOS. Thanks so much for listening and see you next time.

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