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 Kaelyn. That you say, I guess we didn't actually get that is.

Yeah, you got it. You got it.

He's got some great experience. I'm in a great background that he's going to talk through five 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, Caitlin, 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, 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 Sasser's YouTube channel as well as this slides via screen Share or SlideShare. Excuse me. And then lastly, 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 role, so you can look for like minded people that you'd like to network and connect with over the next three days. And that is it from me. So without further ado, Kaylin, take it away.

All right, great. Thank you. So I really appreciate everyone joining me today. I know there's a lot of other things you can be doing in 30 minutes these days, but 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, in an early stage you're learning just so much, especially when you're joining companies that you know, the first 21st 10 employees, you're kind of getting a mini MBA of like how to, 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 five most important lessons I've learned specifically on the sales leadership side. And I'm hoping excited to share with you today. So just 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 state 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're 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 two 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 was 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 their growth and success. And around the time I left Dropbox for 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 our first sales leadership hire and employee number eight and similarly kind of helped them build out their early go to market efforts at that company as well and spent about two and a half 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 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 bok. So there I am on the left, on the bottom left you can see I had a little bit more hair back then that I had in picture number two in 2015. So I will say the bonus lesson here, even though I'm only giving you five, 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 offset when we were small. So it's 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. Cool. So just to jump into lesson one, 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, this would be someone who works on the back end or infrastructure or is an SRE or works on the API, et cetera. Very, very versatile engineering hire that is highly sought after in the early days. You can work on anything. I like to look for the same kind of equivalent role in the sales space when I'm building out my teams. 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 into the presale side to have a little bit more deeper continuity. And so when I think through 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 four 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 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 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, you know, someone in the past who you know, has put in, you know, they have some sort of quantitative, 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 something that you as a founder, early sales leader, it's pretty easy to kind of determine based on 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 four characteristics and you groom people well to kind of 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 antidote here is of our first 10 hires at Dropbox on the sales side, four of them have gone on to be VPs of sales at these four great companies. These are my first 10 hires. So it shows that we did a pretty good job. 40% of our team kind of went on to building teams of their own at Luminarius tech companies in the Valley today, in this next generation. And so there's just a lot of value to unlock, 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're 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 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 drop or drop, Dropbox or box or front even where it's not as obvious what the use case is in 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, when we were selling early on, I'd probably say we were about 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 products. So 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 median 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, 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 of 3PL, if you're not familiar with acronym, it's third party logistics, we had a very, very large 3PL company coming down 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 robot would look like for this vertical, but we also were able to kind of really, really understand the space deeply. And that again, we took those learnings and applied it to outbound, even doubling down to the point where we were going to all the big three PL industry conferences across the country. And that led to a lot of new wins for the business. So this is something you want to look at in conjunction with like usage trends of how people are actually using your product, like for example, using something like Mixpanel or amplitude. The third lesson is be the voice of the market. So this actually, this is 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. 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 test or measure how they're using, are they getting value out of the product? And, and thirdly, constantly iterate and improve based on that feedback. And so I think this is when 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 structure 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, 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. Make sure they know, you know, what are the drawbacks to the current product process. Make sure you know, what the objections are, obstacles to winning those, those, those large deals. Because this will just help you in conjunction with, you know, kind of like all the stuff you, 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 learning to kind of make sure you're on the right track and kind of find that intersection. You know, kind of. For example, 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 development process and you could upvote and, and this, this had like immeasurable benefits in that, you know, customers really, really just got behind knowing that we had like, 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 were like, oh, you're working on this stuff. This is stuff that we were going to ask you to build. Why don't we decide 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 are using the product. And there's a lot of, you know, kind of byproduct benefits to that. Right. You know, 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 a hundred leads the next morning of people saying I didn't realize Dropbox is building a business product. And so you know, this kind of community led growth which is, I know it's 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 again we will have question Q and A. Towards the end I pulled up a tweet here which is lesson four, which is stay in your lane. So I pulled up a tweet from the godfather of Saster himself, Jason Lemkin. 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 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 it's always alluring to pad your title with more scope. So BD and partnerships doesn't seem that far off the beaten path of what sales is, which is still relationship based or you're working on converting leads at the top of the funnel. Why not just own marketing? That seems simple or, 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 mind share to that function. Because you know, things like sales also encompass sales ops which is, has a high degree of complexity itself and is ever evolving or you know, sales development where it's like, you know, it's kind of really, if you're playing the numbers game right, you're also doing a lot of, it's a 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 you 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 if you want to be at 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'll be focused on sales and hitting revenue targets and company plan and everyone wins. Right. Versus trying to pad your resume. And then lesson five, which is 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 you have to think about as a revenue leader and you might be on the hamster wheel on monthly goals or quarterly goals and the numbers are aggressive and you're feeling the heat. And again, there's a whole other set of scope as we talked about earlier. Within the sales realm that you have to focus on like strategic priorities or product roadmap or 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 up front in Dropbox and other places and 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, I'd say probably late August, early September. And I really pushed 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 kind of worst, medium and best case scenarios. And let's make it really, really usable for through layering in things that 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 what is you need to have historical. So sometimes you have to give it a month or a couple quarters to 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 the reps you hire incorporating other attributes like seasonality or rep productivity or even just repetition 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 have in a situation where you're under assigned or way over assigned in quota and you're kind of, you have a lot of inflation on your team where people are just not kind of hitting healthy ote to 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, other kind of levers that you know, a VP 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 gather over time. 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 five lessons we talked about on this slide. So again, reminder, bring in the best versatile talent and that really will unlock potential and value for their business. 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. Really, really focus on those verticals that really love your product and start there and then expand. Right. Don't bite off more than you can chew. Number three, 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 four, 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 to especially in a real estate startup. And then number five, I know we all heard, we all probably seen Glengarry Glen Ross and we also 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 three months or trailing six 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 and A. So let me open the chat. Looks like we got 11 questions here. Dave, excited that you used front. So it is a great product as well and if you haven't checked it out, you should definitely check it out. Cool. Dave. Yeah, it sounds like you brought up the Kanban chart, which is awesome. We got a question here from Rob. What is the one thing you wish you knew at the beginning of your sales career and as an individual contributor? I think it a little bit. Just think long term and try to acquire as many skills as you can as early on when you're, when you're, 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 to join a startup early and I, you know, I've been addicted ever since, but I would 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 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 doing well on time. We got six minutes. I'll try to get through all these. Garrett asks, what are any recommendations on training content for a salesperson transitioning to managing a sales team? I would say Saster has some great stuff. I think Jason and any other folks that are contributing content there, obviously Saster is great and I actually have a heavily used Saster for years since Jason launched it to just kind of read about things like 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 five items are most difficult for CEO founders to help the sales leader accomplish. I think a lot of the biggest kind of wall to jump over for a sales. I mean I think it's like finding the balance of 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. I think 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. It took them 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, and use and are willing to pay for and then you can do things to layer in 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 got a few. What's your take on sales led versus product led? This is a very hot topic right now actually on Twitter. I think that 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 price. So you know, I think of notion, Slack, Dropbox during its time 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 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 going to be using your product if you have a, again if you have a horizontal product that can be used top down. And so you want to get sales folks in there early number one, just because like you know, if you have something that you're onto a big idea, the incumbents are three to four 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. I'm sure they would love to be an independent company. But Microsoft came along and started to build a competitive product very quickly, then bundled it in with Office365. We also saw this with Dropbox as well with adding it as another feature within the suite. You want to start to do this stuff early, invest in enterprise, build an enterprise sales team. It's only going to augment your ability to grow or maybe change your growth trajectory. I think we got time for two more. And by the way I'm umbrella 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 SD? Jess asked do you outsource SDR's 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, 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 don't I like to keep everything in house because you know again when I'm joining companies I may be the first sales go to market person or maybe I'm inheriting a team of two or three. I want to know what the positioning is like and I just don't think if you're working with an outsourced firm that can do your product or company justice. You want to 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 their knowledge and their understanding of your product value and your product positioning. So kind of leave you with that. I'm trying to see if there's any, there's a bunch here.

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.

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.