How focusing your efforts on the correct buyer persona will scale your business

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-Off. On this podcast, 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. Today, I'm joined by Vinay Hiremath, the co-founder and CTO of Loom. Over 12 million people across 200,000 companies use Loom today for asynchronous workplace video messaging, including large enterprises, such as Olympus, Procter & Gamble and Lacoste. Along the way, this meant Loom needed to become enterprise ready and start building new features and functionality for enterprise IT admins. We're going to dig into all this and more and talk about how Loom is moving up market in Crossing the Enterprise Chasm. Vinay, welcome to the podcast.

Vinay Hiremath (01:09):
All right, sweet. We're good to go.

Michael Grinich (01:12):
So, let's just dive right in. Give us a quick update on Loom. Where's the business and team today and what's your current focus?

Vinay Hiremath (01:19):
The business and team is, we're going on about a 195 individuals. We're distributed from New Zealand to Poland with the majority of the employee base within the US plus or minus those time zones. And the focus for the company really, 2021 was a foundational year for the company. We spent a lot of time building out two new pillars specifically. One is our integrations and SDK pillars. So, we just released recently our record SDK, which allows you to record videos. Loom's within the browser for anybody that implements the code within the browser, no download for extension, no installation necessary. And we've been able to partner with folks like Trello and Miro and Figma, be able to deliver these video recording experiences directly within their problems.

Vinay Hiremath (02:12):
So, that's something that we built and released really just a month ago. And then another foundation that we've been building is something that we're calling our destination. Basically our team's base product, which is really just like a Google drive experience for videos was great for IT admins and being able to unlock the consolidation story for making Loom a multiplayer story. But in actuality, we found that Google drive model when you're creating these videos at scale, is actually really archaic and outdated and not the right information model. And so, we've spent a significant amount of this year building the foundations in place to allow for a really flexible tagging system, allow for people to publish Looms within their workspace and discover content that is relevant to them, without them having to find it or understand the imposed structure that other people pull within their workspace.

Vinay Hiremath (03:06):
And then there's a lot of really cool stuff that we're doing, like being able to auto ag things using OpenAI GPT-3 against the transcript, being able to auto title Looms. I think 30% of people title their Looms and having titled your Loom when you have this ecosystem and workspace for teams that use us at a large clip, like Atlassian, HubSpot, some of our biggest customers, they have hundreds of thousands of reportings, having these titles, having these tags are really important. So, we've been building a lot of foundations for these two pillars. We've also been scaling up quite a bit within our create pillar, which is where all of our recorders live. We've had a ton of growth on our platform.

Vinay Hiremath (03:45):
And so the great thing, and I think the thing that, Michael, you're probably appreciating, basically we have this O of N sort of device problem where as long as Logitech keeps existing as a business, Loom is going to break in new ways that we didn't foresee as we add more people to our platform. And so a lot of 2021 was also building these stability foundations for our create pillar. And basically 2022 is going to be about us fully focusing on driving up the volume of activated work signups for our platform and being able to really build within these foundational pillars that we've sat within this year. And so that's kind of where we're at and where we're going to be going in 2022.

Michael Grinich (04:25):
That's fantastic to hear. I mean, the set of enterprise companies you're already working with today is super impressive. And it sounds like you have extraordinary ambitious plans for the next year. I want you to bring us back. Take us back to those earlier days when you were just launching Loom, people were just starting to record their first Looms and bringing it to the workplace. How were you thinking of the product in that phase before you had all these enterprise features before you had enterprise adoption, what were those moments that you went through when you started really seeing it click from the product design and experience itself?

Vinay Hiremath (04:56):
It's funny when we first built the product because the Loom is a new workplace behavior, we actually really didn't know what we had. When we had released the product, the first incarnation of releasing the product was okay, there's this cool thing that we did. Hopefully, we gained some traffic, and that traffic we can drive back into our user testing platform, which is what we started as. And then hopefully we can raise some money to just keep working on video user testing. And so Loom taking off as a product was a surprise, to be honest. And there were multiple sort of light bulb moments for us. One of the light bulb moments that I tell people all the time is like there's this person who reached out to us in the customer support chat, and they wanted me to repair their video.

Vinay Hiremath (05:44):
And basically, in order to repair the video, they were like, there's green lines in the video. Can you repair it and send it back to me? I had to look at the video, and it was this person who's screaming at their screen in Portuguese. And there was a stock ticker that was going down. And so I repaired the video, and I returned it back to the user. And I was just like, Hey, you don't have to answer my question here, but I would kill myself if I didn't ask what is going on this video? What are you using Loom for? Up until now, we've only seen it used as bug tracking or one-off videos that people want to send to each other. And he was like, well, me and my partners won a hedge fund in Brazil.

Vinay Hiremath (06:22):
And we manage over 75 billion worth of assets. And one of my partners made a really bad decision, and I thought your tool was the perfect tool to let them know how I felt about that decision. And so that was kind of like those types of stories started taking off. And that's when we started to realize, okay, there's a lot more to this. It's starting to organically grow. And people are starting to pick it up for new and expanding use cases that we never knew about before. And so what we started to see was a bunch of pockets of smaller teams and evangelists starting to pick up video messaging. They didn't really know when or how to use it. And the cool thing about the Loom journey for Loom mates internally, that's what we call our teammates, Loom mates. For Loom mates internally. The cool thing was that we were kind of going on this journey with our customers.

Vinay Hiremath (07:08):
We were figuring out hybrid and remote work with them. We were using Loom in new ways that seemed natural. And then we used it in ways that were totally unnatural. And we're like, okay, we're definitely overusing our product at this point. But basically around like a year after that launch, we went through this interesting transition phase where we started to use it for basically all operational areas where you needed a lot of fidelity, and you wanted to cut down on back and forth communication and drive away ambiguity and know exactly what you're talking about. So we started using it for analytics updates. We started using it for investor pitches and memos. We started using it for sales and BD outbound. We started using it for code reviews. And basically we were probably three or four years ahead of where we're at right now.

Vinay Hiremath (07:54):
Where we're using the product the same way that people are probably using it in market right now, about the three to four years before it. So we've always had this viewpoint on how to use video messaging at work way ahead of the market, just by the merit of us being within remote and distributed for a while and kind of understanding this new behavioral change. And so when we start to see companies start to pick it up in the same way, really the first lighthouse customer that we had was HubSpot. I remember us having, I think it was like 20 employees at HubSpot using Loom regularly. And it was just a crazy sort of number for us at the time. We were like, oh my God, 20 people are using it. They're not just using it, they're using it every single day, just like we use it.

Vinay Hiremath (08:39):
It was a really full moment. And then it started exploding. And then it was like a hundred people. And then it was a thousand. And then we were like, how the heck are we going to sell into this company? We have no idea how to do a wall to wall deployment. We had no idea what we were building. And now that people are actually starting to use Loom the same way that our company uses Loom, we have to figure out our enterprise story really quickly. And up until that point, we had really hyper focused on the single player user experience. We wanted to make sure the recording stability was as good as it possibly could be. We wanted to make sure that the user experience was really dialed in, the onboarding was as fast as possible. We wanted to make sure it worked as much as possible across all the platforms that we started to support.

Vinay Hiremath (09:20):
We were building features that our users just wanted. We were very much selling this phase of, okay, our users want a download button, ship it to them. We didn't have real product planning. Right?

Vinay Hiremath (09:31):
And so we had to take this thing that was largely a single player user experience and go through this transition of understanding how do we actually make it multiplayer? How do people actually manage videos at scale? And how do they think about the information hierarchy? And what is the buying persona that actually cares about this? And that's been a long journey. We're still in the middle of it. And it's evolved rapidly at several different points along the journey. And I'd say that we're still going through a bit of a nexus of it where our buying persona, especially through the pandemic, has really shifted from these individual teams that have these specific use cases to now heads of ITs, CIOs, CHROs who want to use Loom as a way to create culture and cohesion, who want use Loom as a way to be able to bridge the context gap between employees who are coming into the office every single day.

Vinay Hiremath (10:21):
So it's been a long journey. We're kind of in the middle of this journey of we're finally just selling into these enterprises where we're able to do wall to wall deployments, multi tens of thousands of seats. And we're really at the beginning of that journey, that repeatable sales journey.

Michael Grinich (10:35):
You talk about shipping that download button for the individual user, right. Asking for, I want to download my Loom. What things came from those teams, those team use cases, which was maybe different than the individual use case? And if you could walk through the path from that to these larger and larger organizations, I'm just curious to hear about how kind of your product roadmap evolved and changed in conjunction with your customer base evolving and changing?

Vinay Hiremath (10:58):
Yeah. So the individual roadmap and the team roadmap, I think that we took a very utilitarian view on the team roadmap for a long time. And so this was the result of multiple things, but I think that one of the reasons why we took a very utilitarian view on what team features could be, is because quite frankly, we just didn't have a use for it ourselves. And we were the biggest power users of Loom. And so the biggest thing that we really shipped at the beginning that was the team feature was consolidated billing. And it didn't even have a shared dashboard. When I say consolidated billing, it's like one account could just tie several accounts together, but still the user experience is the same for all of the individual accounts. And that was the first teams thing that we delivered.

Vinay Hiremath (11:45):
Then we started to realize, okay, people are actually really consolidating all of these videos into these Google docs or these notion docs or whatever else. And they want a place to be able to structure that content within their workspace. And so we started to deliver folders and a Google drive experience, which in retrospect was actually a huge mistake. I think that if we had looked at first principles of how should video information actually be structured? We would've gone with the tagging system way earlier. And we probably would've been way ahead on our team journey and roadmap. And all of the things that we had built this year would've been more about innovation versus just foundations. Which who knows what that opportunity cost looks like? Who knows if the market would've been ready for it? But I think it's something to acknowledge.

Vinay Hiremath (12:31):
And so really the way that we started to think about the different use cases that popped up between team and individual, is that a lot of the team use cases that we were hearing from our customers, we just didn't have a need for. Because basically at the point that HubSpot was adopting our tool at scale, they were adopting Loom at the hundred plus mark when our company was like 20 people. And so basically, we had all these customers, we knew the most about how to use Loom operationally, but our customers started having these pain points that we didn't really understand early on because we just couldn't. Our company just wasn't big enough. We didn't have enough customers that were using us at several hundreds of employees recording thousands of videos. So really we only had these few customers that could give us the insights as to how their company runs.

Vinay Hiremath (13:22):
Obviously that's very different now, but what it ended up being is that we ended up doing 90, 95% still individual features that focused on the individualistic user experience. And really we ended up making, in my opinion, short-sided product calls on the team's experience. And we ended up paying for it in the long run. I actually have a blog post on Loom called engineering lessons, shipping Loom pro. And we talk about all this stuff. We also talk about the teams experience, all that kind of stuff and all the mistakes that we made both technically and from a product standpoint. I will say that despite the fact that we overly indexed on our own use cases, our own problems, the individualistic user experience, I actually think that overall that was the right call. This might be specific to Loom because we're a new user behavior.

Vinay Hiremath (14:10):
So a lot of times it just takes a long time for that initial champion who you uses video messaging at work to actually have it proliferate to other people within the organization. But because we focused on the individual so much, we really do have a fanatic user base that loves using Loom and swears by it. And that has been a massive driver for the enterprise deals that we're seeing today.

Vinay Hiremath (14:32):
It's basically the major driver. We have a very typical bottoms up sort of motion where people start adopting Loom. There's somebody who's really comfortable with video, is sort of evangelizing it in their organization. It's really like this nine to 18 month journey. And then all of a sudden it starts exploding within the company when they start to realize there's a need for it. And so even though I think that that sort of prioritization and focus on the individual and those pro features that they needed call to action, custom thumbnails, was overall it led to an unideal outcome, and we started to think about the team's experience. I actually think that the ratio of spending that much time on the individual was still the right call for a bottom self tool.

Michael Grinich (15:12):
Do you have a sense of what percentage today is focused more on the team based approach, the groups versus the individual? It's probably not 95 5 today.

Vinay Hiremath (15:21):
Definitely not. So it's funny because even the team's features, we still try to take the approach of what do the team's features look like to the individual? And the incarnation of what that means at different areas is different, right? So for our manage or admin and enterprise team, they think about the IT admin, like how wonderful an experience is it for the IT admin to go out and hook up Okta or whatever else, ADFS into their org, and just seamlessly, get everybody onto tool. What is their experience with other products? Is it shit? Because if it is then, how can we do better? How can we actually have to light the individual still something that's really core to our product and design teams at Loom? But if I had to guess, teams based experiences, we're probably spending at least 50 to 55% of our product design and engineering resources on that right now at our current stage.

Vinay Hiremath (16:16):
My guess is that that will become even more over the next year. And also this is largely driven by the fact that we finally went zero to one on marketing this year. We just hired a VP of marketing this year. We just figured out how to do a repeatable sales motion with multiple thousands of seats. And so we're about to more than double our sales team next year. And so there is a driving function on the go to market side that is driving this kind of focus on the product side. But if you actually look at the org as a whole, we're going to become more and more sales driven. Not because we're not a product line to org. We're always going to be a product led org. But because there is just so much opportunity out there, especially with what the pandemic has accelerated a necessity for collaboration in a different way than people are already doing it.

Vinay Hiremath (17:04):
So lots of focus on teams based experiences, lots of focus on enterprise and admin. We fully expect to own everything from a one person mom and pop shop and make that experience just as wonderful for them as it is for a multi hundred thousand person, large public bank. I can't disclose names, but you can probably extrapolate what are the biggest banks that you use? We're talking to some of them, so it's really all over the place. And we're trying to own the entire market at this point.

Michael Grinich (17:36):
You mentioned this bottom up approach, which is very common today for modern B2B SaaS products, and that individual focusing on the individual experience drives that adoption. I saw that you guys recently hired, I guess, about a year ago, your VP of sales and success. I'm curious when was the right time to hire that? How did you think through that? And what did you look for in that leader in bringing that person in, particularly around this bottom up approach and how that drives forward your sales?

Vinay Hiremath (18:02):
As soon as we started working on the team's product, we knew we would need to start experimenting around sales. And so the one thing that I'd say is that I think there's kind of an aversion for a lot of product led founders to hire in a VP of sales. And they end up doing it very late. It's a meaningful dampener on the total amount of velocity that you can have in the long run. And so we knew, even though we were just starting to close these team based accounts, we were just starting to do it. We wanted to hire a VP of sales ahead of time to own all of it, because it was our intention to go after large whales and large enterprises in the long run. And we knew because Loom is a wall to wall product or one that philosophically we felt should be wall to wall.

Vinay Hiremath (18:51):
We knew that we wanted to bring forward that VP of sales ahead of closing any of those types of deals. What that means is that the typical quota structure that you end up giving a VP of sales, you can't do that early on. You need to give them some leeway to figure out what that repeatable sales motion is. But the great thing about doing it early is that you build a significant amount of trust leading up to that kind of quota structure. And then you also build a significant amount of IP in that sales leader. And that IP is really important because if you have a bottoms up SaaS company, how important is expansion versus going in for a new deal for your company? I don't know, but we've figured that out at Loom and it's like all of success and all of customer experience also reports into our VP of sales because of it.

Vinay Hiremath (19:35):
And so I think a lot of these questions about expansion versus going after new accounts versus, where do you go top down? What are the different markets and segments? If you hire forward a VP of sales, especially if you're starting to see mid-market accounts, smaller accounts start to close and you know your intention is to go wall to wall or you know that your product takes up a significant amount of expenditure on an IT budget, I think that it's actually a good idea to probably hire out a VP of sales anywhere from eight to nine months ahead of the time that you actually think that you need them. Because you actually want them to be in your company, absorbing all of that IP, building up that intuition so they can be more effective and be able to scale themselves out of areas that maybe aren't as important or that aren't their bread and butter that are still important for the company.

Michael Grinich (20:22):
What does your typical enterprise journey look like for your enterprise customers? Are they coming to you inbound? Are you doing outbound to those IT directors of those procurement folks? I know you've had a bunch of momentum from the bottom up motion, but how does that turn into those commercial enterprise deals today?

Vinay Hiremath (20:38):
It's a good question. The answer for Loom might be a little different from other companies. And the reason I say that is because a lot of our enterprise motions are like, okay, there's already a lot of people using it. There's this bottom up groundswell that came up, and then we're coming in top down. And we're really just trying to understand where the opportunity is from a buying persona. That is a lot of our deals, but increasingly we are seeing a lot of deals from CHROs and CIOs who just understand that remote work and collaboration is something that they are not good at, and they're not informed about. And Loom as a tool ends up coming up a lot, probably at the same or similar rate as Zoom or Slack. We're in this interesting sort of transitionary period from a how we work as an economy standpoint where we've also been getting a lot of tops down interest that honestly, I wouldn't have been able to predict.

Vinay Hiremath (21:34):
I think that it would've been difficult for me to predict that the pandemic would've lasted as long as it did and it would've had as big of an impact on remote work as it has. And that there would be this giant resignation that a lot of people are seeing, and so people are trying to keep and engage their employees that they already have to keep the IP in house. I wouldn't have been able to foresee it, but we are also in this really special place and position as a company where we are getting these tops down, sort of sales coming in. One of those is these C level executives who have inbound interests. We've also been doing things like running these account based marketing meetings with other industry leaders, trying to talk to them through our BC firms.

Vinay Hiremath (22:16):
We also went to Saker where we were able to get a bunch of inbound demand and generate a lot of lead demand that we didn't have before. And also we've been approached by resellers and distributors like TD Do Bu whoever else. And so we're starting to entertain those conversations. I think that we're not quite ready to go through a lot of those resellers just for where we are in the enterprise motion. And hopefully WorkOS will help us in the long run there. Basically, we're trying to get into these companies, given that it's a special place and time for collaboration and remote work. We're trying to get into these companies in any way we can. We're not super opinionated about, okay, we're only going to take deals from CHROs that come through our VC network. For us, a deal's a deal. And we think that Loom and video messaging is broadly useful for everybody. And there's a real value add. And so we're going to go into those deals anywhere and just learn as much as we possibly can.

Michael Grinich (23:09):
Vinay, last question before we wrap up, a lot of the listeners to this podcast are early stage operators, founders, CTOs, folks like yourself, but maybe a few years ago, what advice would you give those early stage entrepreneurs looking at going up market and building new business products?
Vinay Hiremath (23:27):
I think it would be understanding what your actual value add is as a product. Like whether it's a service, a platform or a tool, really understanding what is the value that you to make that buying journey easier. I see a lot of startups. I see a lot of startups, and I'm an angel investor across a few companies where I see a lot of companies and founders focusing on the best user experience. And I'm like, oh man, the person that you're selling into is the CIO. You need to fully focus on that journey. I can already see it. It's like you are an admin tool. You should be focusing on how to make the CIO's journey as seamless as possible. But then I also see a lot of companies that are fully focusing on the enterprise motion and I'm like, but the reason that you're getting in the door at all is because a bunch of people love your product.

Vinay Hiremath (24:22):
And there's all of this block that you're getting publicly about how your product is filling in all of these different ways. So you need to wait more of your attention towards the individual user. And obviously these are extremes, but I think that everybody kind of falls on a spectrum. And I would say that the number one thing to keep in mind is just really understanding intuitively and also by talking to your customer is what is actually getting you in the door for these enterprise sales. And I think that not understanding that leads to a lot of loss cycles. And then also not understanding that and kind of just going forward leads to a lot of loss of focus, which ends up becoming incredibly expensive as you start to scale on your team. So if they just understand what the actual thing is that gets you in the door up market.

Vinay Hiremath (25:11):
And the answer might not be something that's out of a traditional playbook that you're bringing from your previous company. It might be that you have to take a real hard look at, okay, how am I actually growing within the company? And just hyper focus on that one thing. Hyper focus on that one thing, because focusing on just the user or focusing just on the admin could be really expensive any direction.

Michael Grinich (25:34):
Vinay, I think that's really sage advice.

Vinay Hiremath (25:36):
Totally. And we were so early in not even knowing what our tool was, that we were just happy to just service the individuals who were using our tool. And it was so natural that individuals were signing up to just record and send these videos that we naturally hyper focused on the user. As we started to see companies pick up Loom, and we started to have investors ask us, Hey, are you going to verticalize into sales?

Vinay Hiremath (26:04):
Hey, are you going to verticalize into all of these different cross-functional groups where there's specific buyers, specific personas? We made the conscious decision because we had all of these years of leeway to kind of see this tool grow and this behavior grow. We made a conscious decision to stay horizontal. We really didn't verticalize, and we stayed horizontal, and we stayed individualistic in nature. Now you can make a case, did we stay into the individualistic for too long? I think many people would say, yes. I'd probably say no. But it definitely worked out in the long run to be really intentional about that point. And it didn't come without its fallout. There were definitely investors on our team who were like, okay, we're not interested in future rounds. We're here because we think the biggest opportunity for you is the enterprise sales motion right away.

Vinay Hiremath (26:48):
And we're like, we're not going to go there. We're just going to keep building out the thing that we know that users want. And we've actually had real loss of investment, whatever else it might be by making that decision. But I think in the long run it was absolutely the right decision. And we're winning at least right now. We'll see where it goes. I think that each of these chapters refreshes, and you have to reorient the way that you think about your customers and where you're playing, but that's how it pans out for Loom.

Michael Grinich (27:14):
It sounds like 2022 is going to be a big year for you. Can't wait to see what's ahead. Thanks so much for joining us. This has been fantastic.
Vinay Hiremath (27:20):
Thanks, Michael.

Michael Grinich (27:27):
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, SCIM 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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