5 Lessons Learned in Sales Leadership at Dropbox, Box, and Front w/ RevenueCat VP Sales Cailen D'sa

get started since these are rapid fire and the time goes quickly. I'm excited to introduce Kaelin. Is that how you say it? I guess we didn't actually get—

get to know him. That is. Yeah, you got it. You got it.

He's got some great experience and a great background that he's going to talk through. 5 lessons learned in sales leadership at Dropbox, Box, and Front. Before I pass it over to him, I'm just going to run through a couple housekeeping things. So if you want to go to the next slide, Cailin. First and foremost, we want to make this an interactive session. So we've got about 30 minutes to get to all of your questions and to hear from him. If you're comfortable with it, we encourage you to turn your videos off. If not, totally fine. And but hopefully you're here to watch the chat and watch the session. So if you'd like, please turn your videos on so we can see you and make this a little bit more of a roundtable style. Your audio will be muted, but at any time— he's going to make sure that we have plenty of time for questions at the end, so at that time, please feel free to either submit your questions in the chat or unmute yourself and ask live. You can also raise your hand using the button at the bottom of your Zoom. Friendly reminder, these sessions are recorded, so if you don't get to capture everything in notes, we'll be recording them and publishing them on SASR's YouTube channel. As well as the slides, um, via screen share or SlideShare, excuse me. Um, and then lastly, um, after this session, make sure you're taking advantage of the one-on-one meetings on Brella, our partner. I'm going to drop the link in the chat right now of how to sign up for Brella if you haven't already. Again, you can search by attendee name, company, um, role, so you can look for like-minded people that you'd like to network and connect with over the next 3 days. And that is it from me. So without further ado, Caelan, take it away.

All right, great, thank you. So I really appreciate everyone joining me today. I know there's a lot of things you could be doing in 30 minutes these days, but, you know, obviously really appreciate that you've come to join my session. I'm hoping that everyone gets a lot out of this, a lot of value and a lot of insights, et cetera. So to kind of kick things off, currently I'm the VP of Sales at a company called RevenueCat. If you're not familiar with the company, we are building the mobile subscription infrastructure for app developers and for apps on the app stores, iOS and Android. But prior to this, I've had the great fortune of working for some of the most notable iconic enterprise SaaS companies of this last decade. And so, you know, as you can imagine, you know, at an early stage, you're learning just so much, especially when you're joining companies that, you know, the first 20, first 10 employees, you're kind of getting a mini MBA of like how to build a company from scratch and seeing whole functions form. And so You know, I've tried to distill it down to like the 5 most important lessons I've learned, specifically on the sales leadership side. And I'm hoping— excited to share with you today. So, so to kind of jump straight in, give you a quick overview of my background and my journey to date. So coming out of college, I was applying for roles and I found this ad on Craigslist, if you believe it, for a job as an enterprise account executive at an early-stage startup. That company ended up turning into Box. Where I joined as their first sales hire and employee number 16. Most people don't know this, but they were very much focused on consumer at the time. And so kind of my charter mandate was kind of come in and help them figure out how to launch a B2B product and could we even build something that businesses would want. This is back in 2008. And so I spent about 2 and a half years there helping them build out their early customer base and kind of growing that team alongside some great mentors. Eventually that led me to Dropbox, where kind of I took a similar role but leading a lot of our early sales go-to-market efforts. Also Dropbox very much focused on consumer, for some of the tech historians here, and so I helped them launch their first B2B product, which is called Dropbox for Teams at the time. And I was employee number 17 there, and kind of like fast forward today, if you follow them on the public markets, they're doing close to $2 billion in ARR. So pretty exciting to kind of see this, their growth and success. And as it— around the time I left Dropbox, we were maybe about 2,000 employees. I got the itch to go back and do something early stage again. And so I ended up joining the very popular email collaboration app Front, where I joined as their first sales leadership hire and employee number 8. And similarly, kind of helped them build out their early go-to-market efforts at that company as well and spent about 2.5 years there. So kind of kick things off, I went into the archives and tried to dig up any sort of photos I could find that weren't embarrassing. And so you can see here on the left was a picture of us in the early days, back when we were in an apartment or kind of loft office at Box. So there I am on the left, on the bottom left. You can see I had a little bit more hair back then than I had in picture number 2 in 2015. So I will say the bonus lesson here, even though I'm only giving you 5, is that take a lot of pictures in the early days because the startup stress is real. And so you can see here on the right, this is a photo of me at Front and the team at a company office when we were small. So just fun, fun photos. And definitely if you're an early-stage founder or a leader of a small team, take as many photos as you can, hopefully after this COVID pandemic passes. So cool. So just to jump into lesson 1, which I think personally is the most important lesson, is hire full-stack salespeople early on. And so what I mean by this, some of you folks who probably have heard of the term like the full-stack engineer, You know, this would be someone who works on the backend or infrastructure, is an SRE, or does work on the API, etc. Very, very versatile engineering hire that is highly sought after in the early days. You can work on anything. I like to kind of look for the same kind of equivalent role in the sales space when I'm building out my teams. And kind of the value here is they can unlock a lot of interesting insights for you and your business around you know, what is the customer journey? Who is the ICP? Who is the buyer? Why do they buy? What are the value props? But also even after they become a customer, how do you onboard this customer properly? And taking those insights from the post-sale side and bringing it to the pre-sale side, do you have a little more deeper continuity? And so when I think through, you know, some of these kind of the traits I look for, and again, it's very segment agnostic, it's very like vertical agnostic depending on who you sell to. But the kind of 4 kind of universal traits I desire is versatility and someone who can adapt across various different roles, like someone who can prospect, someone who can give great demos, someone who can negotiate with, you know, their counsel to kind of get the contract over the line, but also someone who can work on onboarding and do a first call kickoff and do QBRs, but also, you know, work on renewals, things like that. You kind of want to look for someone who has the versatility to kind of play all those roles. I'm also looking for someone with attitude and just generally upbeat and excited and overly, eternally optimistic. I'm looking for someone with a good work ethic. So, you know, someone in the past who, you know, has put in, you know, they have some sort of quantitative or qualitative evidence that they actually put in the hours and the time and the effort to hit outcomes. And there's a lot of kind of interview questions you can implement into your recruiting process that help you suss this out. And then finally, just passion. And this is something that, you know, you as a founder, early sales leader, it's pretty easy to kind of determine based on, you know, asking questions like, why are you even interested in working for us? And then a sub-point here is actually looking for folks with a high ceiling. So what I found is that if you have these 4 characteristics and you groom people well to, you know, kind of, you know, do a good job in their core role that you hired them for, generally they turn into folks who kind of then can go on to own much larger scope in your organization. So these logos on the right actually, and a good anecdote here is of our first 10 hires at Dropbox on the sales side, 4 of them have gone on to be VPs of sales at these 4 great companies. These are my first 10 hires. So it shows that we did a pretty good job. 40% of our team, you know, kind of went on to, you know, building teams of their own at luminarious tech companies in the Valley today in this next generation. And so, you know, there's just a lot of value to unlock, you know, kind of really, really focusing on the talent you bring in early. And I'll use that kind of like to segue into what you do with all this full-stack sales talent once you have it. And so, you know, kind of shifting gears, you want to kind of start to look for trends or usage patterns in your business. And again, this really depends on if you have inbound leads coming in or if you don't even have any business and you're kind of starting from scratch. And so one of the things, you know, early on when you join, maybe your founder led sales, the founder is going out and trying to kind of— maybe you kind of— that founder has the intuition and vision and kind of know who they're building the product for. But for example, if you're building a horizontal product, like for example, a Dropbox or Box or Front even, where it's not as obvious what the use case is and your addressable market is any knowledge worker across any function, they can get value. It's a little bit harder to determine this. You have to really focus. And so kind of early on, you know, for example, at Box, I'll give you an anecdote here, is that like when we were selling early on, you know, I'd probably say we were about, you know, 20 to 30% inbound, 70% outbound. Of the inbound, we started to notice patterns. For example, small SMB construction companies or architecture firms or design firms were adopting our product. So, you know, just having dialogue with these folks, we learned that they were using the product for a very specific work stream called invitation to bid, which is very popular in the construction space. And so we kind of took that insight and applied it to our outbound motions. And so things like going after the largest construction companies in the vertical And over time, we ended up winning deals with all of them, mostly because we kind of knew that they had this same problem, but just at a larger scale. The same kind of approach and methodology held true at Dropbox with media and design. Dropbox, uniquely of all the file sync and share vendors out there, they do something unique called Delta Sync, where once you sync a large file, we only sync kind of chunks of the file that you iterate or improve on for large graphical design assets, for example. And so media and design firms love the product because it was just a very smooth process to get large files and iterate on large files once it was in the cloud. And then with front, 3PL and operations, so 3PL, if you're not familiar with the acronym, it's third-party logistics. We had a very, very large 3PL company come inbound to us in the early days when we didn't have too many customers. And not only did they help us really draft and understand what our enterprise roadmap would look like for this vertical, Um, but we also were able to kind of really, really understand the space deeply, in that again, we took those learnings and applied it to outbound, um, even doubling down to the point where we were going to all the big 3PL, um, uh, industry conferences, um, across the country. And that led to a lot of, uh, new wins for the business. So, um, this is something you want to look at in conjunction with like usage trends of how people are actually using your product, um, like for example using something like Mixpanel or Amplitude. Um, the third lesson is be the voice of the market. Um, so this actually, uh, this is a kind of a graph or just kind of a diagram of the continuous feedback loop that was coined by Eric Ries of The Lean Startup. Uh, and he kind of broke it down into three pillars. The first one is just build the product, right? Build something or turn an idea into something tangible that you can put in customers' hands. Number two is, uh, test or measure how they're using— are they getting value out of the product? And thirdly, constantly iterate and improve based on that feedback. And so I think this is something Google does pretty well, right? They've put a lot of products out in the wild and they just kind of iterate very quickly, even if it's kind of half-baked or still an MVP. And so, you know, kind of just beyond this, and, you know, this kind of seems like a very obvious concept, but one of the things on the sales side you really want to do early on is build a structured process around this. And so whether you do this in, you know, a spreadsheet or using something like Productboard or Clubhouse or Trello or whatever tool you use, to track feedback from the market, you want to do this in a structured manner and tie it to ARR. And so once you have that in place and tracking all, you know, your kind of feature requests or critiques on your existing product, you want to be able to kind of cut things by different dimensions, but also make sure this is in the hands of your product leaders, engineering leaders, or even the CEO if they're the gatekeeper of the product roadmap, and make sure you're meeting with them regularly. Make sure they know what the market's asking for and make sure they know You know, what are the drawbacks of the current product process? Make sure you know what the objections are, obstacles to winning those, those, those large deals, um, because this will just help you in conjunction with, you know, kind of like all the stuff. You know, I know a lot of people have the philosophy of, you know, we want to also build things that people don't realize is a problem. You can kind of marry that with market learnings, kind of make sure you're on the right track and kind of find that intersection. Um, you know, kind of, for example, a couple tactics here that you could actually use is, you know, You know, have your designers or product folks do Figma mockups of conceptual things they're thinking about, and then share that with potential customers or prospects so they can see some stuff that's coming down the pike and they'll give you real-time feedback. Or do targeted NPS, CSAT surveys at different points in the customer journey. Or even, for example, at Front, we made our roadmap public from day one. And so we had an upvoting system. We had a Kanban chart where you could see where everything is in the product process, a product development process, and you could upvote. And this, this had like immeasurable benefits in that, you know, customers really, really just got behind knowing that we had like a, like a very disciplined plan on what the things we were going to execute in our product roadmap. It allowed them to have some input into that process, which kind of helped build rapport and trust. And then finally, just kind of like a lot, it helped speed up our sales cycles because customers are like, oh, you're working on this stuff? This is stuff that we were going to ask you to build. Why don't we just have now, we'll be along for the journey so we can help mold that. That's the benefit of being an early-stage startup, right? You can be agile, and that's maybe why they'll partner with you over, you know, a bigger company who maybe has an incumbent who has a competitive solution. I'll give you kind of another great anecdote here is, you know, Dropbox had a very popular user forum in their early days. And so this is kind of the demographic was, you know, our most hardcore users or the biggest evangelists who were using the product. And there was a lot of, you know, kind of byproduct benefits to that, right? We reduced our support ticket count because our users were doing support for us organically. But it also led to top-of-funnel leads. Like, we had soft launched privately Dropbox for Business, and one of our power users posted on the forums. The next thing you know, you had 100 leads the next morning of people saying, I didn't realize Dropbox was building a business product. And so, you know, this kind of community-like growth, which is— I know is a hot topic right now in terms of like growth marketing. It's something that works really, really well if you have very vocal users. So moving on, I know it's a lot to unpack, and we again, we will have question Q&A towards the end. Um, I pulled up a tweet here, which is lesson 4, which is stay in your lane. Um, so I pulled up a tweet from the godfather of SaaS himself, Jason M. Lemkin. Uh, he posted this tweet a few months ago where he said, a VP of sales and success, a VP of sales and marketing, a VP of sales and anything else is usually not really a VP of sales. And this just rings so true with me when I saw it. I definitely favored it as soon as As soon as it hit the tweet line. But one of the most non-obvious lessons I've learned the hard way is trying to bite off more than you can chew. And what I mean by that is like, it's always alluring to pad your title with more scope. So, you know, BD and partnerships doesn't seem that far off the beaten path of like what sales is, right? Which is still relationship-based. Or, you know, you're working on converting leads at the top of the funnel, why not just own marketing, right? Like that seems simple. Or customer success, right? You know, it should, you're still working with the customer. It should generally be the same thing. But I think when you're a revenue leader, especially early on when you're on the trajectory to, you know, kind of triple, triple, double, double, double in the earliest days, it's very hard sales, you're kind of disrespecting the sales function by not giving kind of all of your attention bandwidth and just kind of mindshare to that function. Because, you know, things like sales also encompass sales ops, which has a high degree of complexity itself and is ever-evolving, or sales development where it's like, you know, it's kind of really— you're playing the numbers game, right? You're also doing a lot of— it's very much— you have to go through kind of the volume motions in order to kind of generate pipeline. These are all just very discrete functions that should be owned by someone directly. And so, you know, one of the things that you kind of want to do early on is to really, really just focus. I know it's hard to not take on more scope of responsibility. But, you know, if you want to beat the company plan, you should kind of generally stay in your lane. And the solution here is hire your contemporaries or your peers. Hire someone who can own that part of the function because they're just going to do a far better job than you are. But it's also going to be that beneficial for you as a shareholder in the company in that, you know, you'll be focused on sales and hitting revenue targets and company plan. And, you know, everyone wins, right? Versus, you know, trying to, you know, trying to, trying to pad your resume. So And then lesson 5, which is, you know, probably one of the most important lessons that I've learned, is forecast your future. And so again, there's a lot of things going on in the business that you have to think about as a revenue leader, and you might be on the hamster wheel on monthly goals or quarterly goals, and, you know, the numbers are aggressive, and, you know, you're, you're feeling the heat. And, you know, again, there's a whole other, you know, set of scope, as we talked about earlier, within the sales realm that you have to focus on, right? Like strategic priorities or product roadmap or You know, it's kind of like hiring, things like that. But one thing I found to be very, very useful, that's something I applied directly at Front and Dropbox and other places, is kind of really modeling out your operating plan as a sales leader. And so kind of what I mean by this, like, I start this planning process, you know, I'd say probably late August, early September, and I really push the founders I report to or the CEO to kind of do this very early on, which is let's build a bottoms-up and top-down model that includes, you know, kind of worst, medium, and best-case scenarios. And let's make it really, really usable through layering in, you know, things that, you know, beyond just quota capacity or top-of-funnel leads or conversion rates or kind of year-over-year growth. I also want to look at actuals, right? I want to look at, you know, what is— you need to have historical. So sometimes you have to give it a month or a couple quarters to get actually get some real actual data to kind of predicate your model off. But you want to kind of build a model that kind of helps influence when you need to start hiring, because that's very important. But also, what is the productivity output of, of the reps you hire? Incorporating other attributes like seasonality or rep productivity, or even just rep attrition or ramp time. These are things you need to incorporate into your, into your model to make sure that you're always on track and you don't end up in a situation where you're undersigned or, you know, way overassigned in quota, and you're kind of you have a lot of inflation on your team where people are just not kind of, you know, hitting, you know, healthy OTE to quota multiples for the business. And so Dave Kellogg, actually I pulled this from his blog, he has a really, really phenomenal write-up where he talks about this, where you can also incorporate things like judgment and other kind of levers that, you know, a VP of sales or CRO can actually pull to adjust the numbers based on, you know, kind of catastrophic things that happen maybe throughout the year. But the other more very, very important aspect here is you also want to just not throw this in the closet and forget about it every year after planning. Season, you want to make sure that you are working on it and you're iterating on it based on new historicals that you're gathering and getting over time. So, um, so, yeah, I mean, let me— I know this is, you know, there's a lot of content to unpack here, and I'm sure that, you know, you're going through multiple sessions, each of you, throughout the day, especially during this Zoom era. And so I've actually just captured the takeaways here of the 5 lessons we've talked about on this slide. Uh, so again, reminder: bring in the best versatile talent, and that really will unlock potential and value for their business. Uh, secondly, act on any trends or patterns to augment growth and take those insights and apply them to your outbound motions or the events you attend. Um, really, really focus, um, on those verticals that really love your product and start there and then expand, right? Don't bite off more than you can chew. Uh, number 3, create a strong feedback loop with product engineering and make sure that's something you're visiting every single week. And put that into practice and make it a serious kind of focus for the organization. Number 4, focus on your core role and embrace your contemporaries. It's okay to just be a VP of sales. That's awesome because it's a lot of responsibility in itself. And, you know, it's a— it's not a 40-hour job. It's an 80-hour job, 100-hour job, especially at an early-stage startup. And then number 5, I know we all heard— we all probably seen Glen Gary Glen Ross, and we all talk about ABC, always be closing. The term I'm going to introduce today is always be planning. And so make sure you build that plan, make sure you iterate on that plan as you get new historicals or new data points based on the last trailing 3 months or trailing 6 months, and continue to improve that plan to make sure that you can look around corners and avoid any, you know, short-term pitfalls that may come your way. So without further ado, thank you so much for listening. I hope that was insightful. So I'm going to actually open it up to Q&A. Um, so let me open the chat. Looks like we got 11 questions here. Um, Dave, excited that you used Front. So, um, it is a great product as well. Um, and if you haven't checked it out, you should definitely check it out. Um, cool, Dave. Yeah, it sounds like you brought up the Kanban charts. This is awesome. Oh, we got a question here from Rob. Uh, what is the one thing you wish you knew at the beginning of your sales career as an— and as an individual contributor? I think it a little bit is just think long-term and try to acquire as many skills as you can as early on when you're in a sales role. Try to shift your brain to start to absorb as many concepts and start to think bigger picture versus just thinking about your individual quota. That's one of the reasons why, you know, I was fortunate enough to join a startup early and I, you know, I've been addicted ever since. Uh, but I would— the, the benefit of joining an early-stage startup early on in your sales career is you just learn a ton. Like, I've gotten to see the whole marketing function form from the first hire all the way to a team of 50. I've gotten to see all the tactics that have worked and not worked. But I also have— I learned over time working for multiple startups, you start to piece together the bigger picture of why do you do things that kind of lead to success longer term, that eventually help you, um, change your career trajectory. Oh, a lot of questions are coming in now, so I'll try to get to them and make sure we're, we're doing well on time. We got 6 minutes, I'll try to get through all these. Um, Garrett asks, what are any recommendations on training content for a salesperson transitioning to managing a sales team? Um, I would say Saastr has some great stuff. I think Jason and, um, any other folks that are contributing content there, obviously Saastr is great. And I actually have heavily used Saastr for years since Jason launched it, um, to Just kind of read about things like, you know, kind of planning or quota carrying, things like that. Atrium, which is a startup, also is writing some great stuff. I think their CEO Pete just wrote a book. So there's some really, really great stuff there. And just honestly, I'm just kind of generally a student of the game. I grew up in Cupertino and I've been around. My father was a serial entrepreneur in the '90s. And so a lot of time I'm just kind of— I try to network. I try to go— I'm actively on Twitter following people way smarter than me, trying to learn about anything I can about building a company beyond just the scope of sales. So John here asks, which of the 5 items are most difficult for CEO founders to help the sales leader accomplish? I think a lot of the biggest like kind of wall to jump over for a sales leader, I mean, I think it's like finding the balance of, you know, realistic growth with what your product can accomplish today and being just realistic. I think a lot of times it's easy for you to say, let's triple, triple, double, double, double. Let's run 200 miles per hour and build this company from a revenue perspective, but maybe you don't have the historical data to prove that. Sometimes it's okay to slow down. Look at Atlassian. They were— now they're 20 years going, and I think they went public in 2013, and they're well over $1.5 billion in ARR. You know, it took them, you know, I think over a decade to get over a billion in ARR. It's okay to slow down. And growth at all costs is not always the answer here. You want to make sure you're just continuing to build a great product that people love and use and are willing to pay for. And then you can do things to add layer and value on your product over time through iteration that eventually you increase your deal sizes. There's a lot of here, a lot of questions here. I'm gonna try and get through as many. I think we've got a few. "Uh, what's your take on sales-led versus product-led?" This is a very hot topic right now, actually, on Twitter. Um, I think that, you know, obviously I seek out companies that are product-led because you already have a groundswell going on. And I just generally, you know, I look at the universal characteristic, right? So, you know, I think of Notion, Slack, uh, Dropbox during its time. Um, there's just so many companies that very much were self-serve, and those are kind of the companies I seek out. When I go for full-time employment. But I do strongly believe, I think there's, you know, the controversial topic is, do you just go product-led and just wait until you really start to, until your growth kind of starts to taper before you start to layer in sales? I'm a big believer you should hire sales early. And the reason being is there's a lot of insights you're missing out on. You may have enterprise customers or buyers are not going to self-serve. Maybe they will if you have a product that can be used at the line of business level. But they're probably not gonna be using your product if you have a horizontal product that can be used top-down. And so you wanna get sales folks in there early, number one, just 'cause like, you know, if you have something that you're onto a big idea, the incumbents are 3 to 4 years away. Microsoft, Google will start to launch a product. I think we saw it very recently with the Slack acquisition, although Slack had an amazing outcome. You know, I'm sure they would love to be an independent company. And so, you know, but Microsoft came along and started to, you know, build a competitive product very quickly and then bundled it in with Office 365. We also saw this at Dropbox as well with, you know, making, adding it as another feature within the suite. You wanna start to do this stuff early, invest in enterprise, build an enterprise sales team. It's only gonna augment your ability to grow or maybe change your growth trajectory. I think we got time for 2 more. And by the way, I'm on Brella. So feel free to add me and send me any notes, or I'm very accessible on LinkedIn. So feel free to connect with me. I add everyone. Do you outsource ST? Jess asked, do you outsource it? SDRs work in early-stage startup, or do we really need to find full-stack AEs? I don't think you— I mean, there's some platforms out there. Again, I come from the early era where there wasn't sales dev as a service firms out there. This is kind of a new phenomenon. Generally, I like to keep everything in-house because, you know, again, when I'm joining companies, I'm maybe the first sales go-to-market person, or maybe I'm inheriting a team of 2 or 3. I want to know what the positioning is like, and I just don't think if you're working with an outsourced firm, they can do your product or company justice. You wanna capture those insights in a way that's very structured and you want someone just full-time living and breathing this stuff, but also being around other folks cross-functionally who can help like influence their knowledge and their understanding of your product value and your product positioning. So kind of leave it at that. I'm trying to see if there's any, there's a bunch here.

Uh, any that you can or want or need.

Yeah, I think there's some organic conversation going on here about Snowflake and Shopify, which are both amazing businesses.

Um, one I'm not sure if you saw, which is really cool maybe to end on, is what if a few of the most important things to get right starting from a sales team, starting a sales team from scratch, that you'd focus on?

Yeah, so