“Everyone wants a silver bullet” — Selling lessons from Sam Taylor, of Dropbox, Quip & now Loom

[00:00:00] Everybody wants a silver bullet. What's the use case, or what's the one thing that unlocks someone finding value on these services? What's the thing that we can just bottle up and ship out to folks and everyone's going to get it. And that's something that I get asked for, frankly, it'd be a whole lot easier if that existed out there, just like, Hey, here's the one thing.

If you tell someone to use them for this, they get it, or Quip or Dropbox or any of these. And so ultimately I think what I constantly have wrestled with across all of these different experiences has been the trade offs, but then ultimately, where do you place those initial bets?

[00:00:41] Welcome to in-depth a new show that surfaces tactical advice, bounders and startup leaders need to grow their teams, their companies, and themselves. I'm Brett Berson, a partner at first. And we're a venture capital firm that helps startups, like notion, roadblocks, Uber, and square tackle company building firsts through over 400 interviews on the review.

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today's episode of the in-depth. I'm really excited to be joined by Sam Taylor. Sam is the VP of sales and success at loom leading all things revenue. He joins loom with a resume stacked with sales experience at product led growth companies. He climbed aboard Dropbox in 2013 as its first enterprise sales.

Next you join Quip as its first sales leader and stayed on for years as a VP after Salesforce acquired Quip. Before he, once again got the startup bug, which brought him to loom in today's conversation, we dig into the key learnings from each stop in Sam's career. So far starting with his earliest experience at Dropbox.

He walks us through his aha moment. That sales is an insight driver, which includes his lessons on pricing and packaging, as well as plotting the feature roadmap as Dropbox moved up market next, he reflects on his time at Quip, including what sticks with him from working closely with its CEO, Brett Taylor and COO Molly Graham.

He also digs into his tested tactics for selling in a competitive market where you're going up against plenty of established players like Google and Microsoft. We then turn our attention to his current role at loom and how he's threading all of those experiences together. He pays particular attention to his partnership with looms leaders and how they're teaming up to achieve what he jokingly calls total loom dominance.

If you're insane nails, you won't want to miss Sam's insights. He's picked up over the course of multiple startups, success stories, and folks that work for other functions at product led growth companies will come away with a greater understanding and appreciation for how sales. I hope you enjoy this episode.

And now my conversation with Sam. Well, Sam, thank you so much for joining us, really excited for this conversation. 

[00:03:33] me. So one place that I thought we could start is maybe talk at high level philosophy and frameworks, and through the course of the conversation, go a few levels deeper.

And the place I was interested in starting is maybe when you look across your experiences at Dropbox at Quip, maybe some of the time post acquisition at Salesforce, and now at loom, you've really been at the forefront of product led growth or the intersection of something that's more product led with maybe some top down sales or sales interfacing with that motion in some way across different companies and also across different points in time.

The Dropbox experience was I think in closer to 2012 and 13, and obviously the loom experiences now in 2021. And so I thought maybe we could talk a little bit about your philosophy of product led growth and maybe specifically, how you think about sales and service or sales or customer success fitting together in companies that are predominantly 

Absolutely. So as you're alluding to a few different phases, a few different categories, if we want to call it within the broader productivity or collaboration space across these companies, I think the interesting constant has been trying to figure out what the currency of the organization is from an insight perspective.

And I think the interesting part early days with is. That was my first selling job. I was coming out of a sales development role at Salesforce. I was in a closing role for a short period of time, and we had so much inbound demand that had we been farther along in the AI bot or outsourcing game, whatever way that you would think about scaling the organization.

I like to joke kind of tongue in cheek. If it had been me or a trained monkey and those charts are going up into the right, in terms of revenue and in terms of growth. And so I think the reflection on the Dropbox experience was there wasn't an early sense of incrementality and rightfully so, because we were just trying to figure out a new motion, but as that scaled over time, Drew a sensitivity for me around what's the goal of the sales team.

If the efficiency may not be there in the same way that obviously your self service engine, or maybe even an assist function might have over time, then what are the insights that you're really driving? Right. There's a piece on the product development that goes into that, which we can get into I'm. Sure.

And there's obviously the logo and customer story and storytelling component that you're bringing to the organization too. And so my introduction to PLG was definitely an interesting one. Given the phase, when I joined Dropbox, it was roughly 50 employees. There were five of us in the sales den at the time and went through a period of significant growth from an employee count perspective and user growth perspective as well.

The, I guess, learning there or the, the impetus to move to Quip was an organic good natural one. And if anything, I probably rotated in a different direction of in talking with Brett and talking with Molly who were on the executive team at Quip at the time, a little bit of an underdog mentality, like team and product.

Excellent. But there was not this organic. Virality that was experienced at Dropbox. And so the sales led motion was necessary and so much more of a revenue driver versus insights driver. And then now being here at loom, we're in a fortunate position where we've got a lot of tailwinds coming out of the last 14 months, both from a macro perspective, but also just a viral perspective within our product.

And it gives us a very different lens on where to sales add value today. And so, honestly, it's almost like a blending of my quick bit and Dropbox experience and a microcosm because we're still early as a relatively small company, but it loom, I think the fascinating part has been my. Intersection with product.

I have a really, really strong relationship with our VP of product and Nick drum, right. And she and I are really driving on what are those intersections and touch points between all of our customer facing teams and the product organization. And that's the good stuff. That's the fun stuff. Bread is the, how do we get some stat SIG insights from our large user base, but how do we also get these really meaningful anecdotes from our sales organization?

And how do we use that in a way that drives hopefully a world-class product experience, which we're focused on, but also a world-class experience with the loom mates that are delivering on that. So I've been rambling across three different companies, but I'll pause there. 

[00:07:55] That's sort of a great place to start.

So going back to Dropbox, you shared that sales was this insight driver, and so maybe you could expand, what does that actually look like? And in hindsight, do you think that was ideal or. Knowing what, you know, now it should have played a different role or the way in which sales and the organic go to market fit together could have changed in some way.

[00:08:22] I think it boils down to where you want to place bets as an organization. And I'd say my early experience at Dropbox was much more around how do we figure out what someone's willing to pay for in terms of monetization. And as we started to get more and more customers, then there was a natural blend towards what are we doing with our product organization to deliver those insights, to deliver that feedback.

We had some amazing PMs that were aligned to our Dropbox for business team. George O'Brien was someone that I worked really closely with. He's gone on to be a part of the Instacart team since then. And the ability to have minds that are willing to hop on customer calls is just the special sauce of that.

Go to market motion. Ultimately the issue we all run into and this, I think applies to humanity, not just companies, not just different departments within companies, but it's all a translation and communication challenge. And so something that I, with my most positive intent as a salesperson may be trying to deliver back to the product team in terms of feedback, insights, customer conversation, there's going to be something missing there because the vernacular might be different or the lens or way that I'm approaching that conversation or just.

My role and what I'm focused on in that conversation is different. And so I think the evolution that we had were the very, very early days of us selling was triaging inbound queue, not a lot of insight because we're just trying to stay above water. In terms of that demand, flipping into an enterprise role.

It was myself. And we had hired a VP named Kevin Egan who joined us from Salesforce. And he and I were sitting there going, I guess we should build a sales deck and go try and pitch this to some people. And we went upper enterprise to begin and a lot of learnings along the way around where people were associating value.

With Dropbox and then ultimately that starts to inform, all right. How do we think about the positioning that we have? How do we think about the feature roadmap and administration that we want to cater to? And I think that those dueling priorities, if we want to put it there around what is the north star and is the north star user growth at Dropbox, less at that because of the vitality, are we getting the tangible insights that dictate our roadmap that started to come to the forefront?

Whereas the north star, Hey, we need to go prove rep productivity. I think we got to a good place about six to nine months into our outbound selling motion where we really, really started to value those insights. And that's where the feedback loop with our product team became a core motion of ours.

[00:10:57] Couple of things to jump off there. You mentioned that when you got in there, one of the things you spent time on at Dropbox was figuring out what someone was willing to pay. And so I'm curious, how did you do that? What were the steps to figure it out? And what did you figure out in that process? We were 

[00:11:11] in a fortunate position where we're not doing any true outbounding, we've got some sort of penetration within these accounts, which is leading to our prioritized list of who we're going and targeting.

The interesting part of that was the learnings around who within an organization was willing to take a sales call. So you started to get one vector of learnings were around the personas where Dropbox as a tool being evaluated and being deployed, formally understanding who within an organization would do that.

Ultimately it started becoming much more of an it sell than I think anyone expected. We really were trying to focus on line of business, but all roads ultimately started pointing back towards that side of the house. And then ultimately it became a question of what are the gating features between our business enterprise and other skews.

That really start to be the drivers for why someone is evaluating that next step up in our PMP. And I think that that component of one. A lot of folks in the valley were SSO. Is that key to the next phase? I think it's a standard level of maturity. And also there's a lot of regulation that goes into a bunch of the certifications that folks are chasing for their own systems and processes that are really that hinge and that driver.

But what's beyond that. What are the insights that start showing the value that the customer would be receiving from your service? We see this at loom, we see this equip. And so I think the interesting discussions really came down to, yes, we understand our users are there. The question is what are we getting out of it, what's the actual value to the organization?

How do you help us quantify that? So we can make a business case that's one piece. And then also, how do you just easily serve up and visualize and, and let people know that it's not shelf where they're receiving consistent value. And I think that's a question mark, that a lot of buyers have today. And ultimately, when you think about just PLG as a broad motion, the expectation is depth of engagement ongoing.

[00:13:05] that a little bit. You were just sort of mentioning the phase. You started to go and figure out what enterprise might look like. And so when you had this bottoms up, you had a sense that X number of people at Airbnb were using Dropbox, for example, or X number of people or Coca, or pick up market or mid-market company.

And you went and you met with them, what do you do in that meeting? How do you structure it? Or what are you trying to get out of it? And what's the role of, as you were mentioning insight gathering versus. Actually getting a huge deal direct with a given company. 

[00:13:40] I think there's been much more of a shift in the last few years, and it was still there, but it felt newer at the time.

And the shift is around employee empowerment. And so ultimately the function or traditional relationship that you'd have in the selling environment is, Hey, you're, you're pitching those that are holding the purse strings and they're making the call on what's going tops down to the organization. And so particularly at Dropbox in particularly going into these enterprises, the concept of there being shadow, it was still relatively new to a lot of these folks and frankly uncomfortable.

And so I think the approach early on, and definitely some bumps and bruises along the way of learning the hard way of coming in, strong around this being a security threat or this being your users are here. We have your data like anything where there's an imbalance of power around. What's already taking place.

Did not land did not go well. Maybe that is the ultimate reason that people ended up purchasing. But I think the learnings along the way in the approach to those initial meetings were, how do you socialize? What is happening, but how do you do it in a way that spun around? There's a gap somewhere, and there's no fault around who created this gap in the tool, set the workflow, whatever it may be, but ultimately like folks at your company are trying to be as productive as possible to make Coca-Cola Airbnb or whoever.

It may be a place where they can be effective and they can drive that business forward. And so a lot of this ultimately boiled down to storytelling early on the data remained the same. It was the framing of how are we taking this user engagement? How are we making it aspirational? How do we ultimately start to shift someone.

Thought process around this shadow, it deployment as something that's an opportunity for cultural change or employee empowerment. And I think that that learning and that approach has carried on throughout both my time at Quip. And now at loom where you have these hyper horizontal tools for these three specific product offerings, the truth of the matter is the use cases are never ending.

And so the approach ultimately has to be, how do you go really, really deep on discovery and learning around these companies? How do you understand the inner workings of what their workflows are? What their philosophies around are around the tools that they use, but tools are just in service of the process and the processes and service of the strategy.

And so ultimately you got to reverse engineer all the way out to what is the strategy for that company. And then how do we find a place where we can articulate Dropbox, Quip, looms, value in light of that strategy? And I think the way that. You see the light bulbs turn on for folks when it starts to be positioned as a way that you can bring, whether it be a company that might be a bit outdated and some of those strategies or processes into the modern world.

And that's an opportunity for those that are going to be the change agents in those companies. That's an opportunity, but ultimately I think the cool part of what we're seeing and frankly, what we're really seeing it loom over the last 14 months is the shift in employee empowerment. That's been driven by what's happened over the last year and we have this kind of interesting paradox of folks want to get back to seeing people, but they also want to make sure that they maintain that flexibility and autonomy that they've experienced in some regard over the last year and finding ways that you can attach your product offering to.

These movements within workforce culture is really what has moved the needle, both Dropbox, Quip and loom alumni, I guess, sort of a 

[00:17:20] closing thought on that early enterprise motion at Dropbox. What is the pricing model and packaging that you landed on and maybe the why or how behind it, and maybe how that co-existed or how you thought about it.

Coexisting with all the bottoms up X number of people at Airbnb took out their credit card, or some of them are using it for free. Some of them maybe have took it, taken out their credit card, and then you're going in and figuring out how do you price and package in the early days and be interested to learn about 

So it started with security and authentication as I was talking about before. And I think that that's a pretty safe place where a lot of folks differentiate between air-quotes business versus enterprise offerings. I think the interesting learning. And value driver that we pretty quickly started to put into our product development and roadmap was around.

Yes, we have this employee population that is adopting this service today. We want to wrap our arms around that, but what's the go forward motion. And I think the fascinating part was this acceptance that this is here to stay. This engagement on the platform is already here. And so how do we begin to wrap our arms around those incremental net new folks that are going to be joining the way that someone flows through and ends up in the right environment?

That's going to be in Dropbox's case, the right set of folders, the right team structure, the right persona or profile. And so very quickly it went from the value of the security component being taken care of too. How do we quickly start to put things in place that reduce any sort of friction around that end user's workflow, whether it be transferring their content, whether it be engaging with their specific team or function or serving up the relevant spaces in places where they would want to work.

And so I think the evolution very quickly from a PNP perspective was great. You've got the security box checked, but now what what's the value add? What's the reason why doing this at scale is a net positive for our end user and employee experience. And that's really where we started to put our product resources.

There were around driving that end user delight, because I think that that ultimately is the engagement driver and the value driver that people are seeing and expecting coming out of this PLG motion. And so what we learned quickly is that having the tops down, maybe checkbox requirements, They have to still be there, but you have to build to execute and deliver those in a way that doesn't sacrifice what brought people into your service in the first place.

And so our PMP really evolved to be in service of that motion. I 

[00:19:57] guess one thing I was reflecting on when I think about your last 10 years is a lot of the products that you've been involved with bringing to market you're often competing against the status quo of like whatever the existing cross sold or bundled solution is for the thing.

And so Dropbox may be, it was SharePoint or something else at the time. Quip is obviously Google docs and Microsoft office loom. You could, I would assume it's sort of a DIY use case of whatever solution someone's using or maybe some bootstrap sort of video and audio recording type product. Are there any frameworks or thoughts you have around how you approach go to market or sell.

Of these products that are somewhat similar to a nearly free product that the company might already have 

[00:20:43] it boils down to. Where do you spend your time up market? Because you're right. I think the number one competitor that you have in any of these scenarios is apathy. What if we do nothing? What if we just continue doing what we're doing?

And so you have to have someone that is feeling in traditional sales terms, some sort of pain and needs to be significant enough that they're willing to change their behavior and behavior change is one of the most difficult things to do with folks, period. And so I think that the scrutiny really came into.

The early phases of our discovery process with any of these larger deals, we would have folks that were bleeding edge adopters, or starting to get into the early majority that are coming inbound. And that's great. Those folks typically have found our service for a reason. They get it, the light bulbs on, I think the interesting component of our sales motion up market was that early adopter or champion, usually not the person that's making the ultimate decision and the one that's holding the budget for a sizeable deployment.

And so the way in which we would do these sales motions is you've got to be deep into the vernacular of that company. I was talking about reverse engineering, the tools or product offering in service of process and strategy. Like if you don't align yourself to a strategic initiative that someone has going on or a major log jam that they have in a workflow, that's been identified as something that needs to be.

Solved in a certain timeframe, you're going to be spinning your wheels with that company for a very long period of time. And so I think the way that we began to approach these conversations were through both equip. And particularly now at loom the concept of structured pilots, it sounds very enterprisey, but ultimately, what are we trying and to do, we're making compelling events, we're driving someone towards a decision and we're trying to time box it and we're setting distinct success criteria for it.

And it's also a formal mechanism where we can try and bring a lot of folks cross-functionally to help multiple thread the offering and the potential license pool, or other departments that we would be deploying to. And when you've got such a variety of folks in the room from a role perspective, maybe even from an altitude within the organization perspective, like where they are in the org chart and what their purview is within there, You've got a bunch of smaller sales cycles that are happening simultaneously to ensure that that person is having the light bulb.

That aha moment, that understanding yeah. How this can be a major shift for their company or a major value for their company, and then tying it all together in a very buttoned up way. So we've even started to getting, and you asked me to get tactical Brett, we're getting super tactical, but we've even gotten to a place where we are setting success criteria.

We are doing mid-point check-ins and surveys within these pilots. We are getting it, understanding of that pilot group NPS, really get a sense of how loved there appearance was with the product. And then ultimately we have, whether it be a large pilot or small, at least some sort of data set to go back and point back to.

You are seeing value. This was the goal. Here's where we delivered on it. Here's the feedback you were able to give to our team. And here's how we'd like to partner with you during this timeframe. And it's early days across the board, particularly here at loom, but really seeing a lot of success in that motion and a great way for us to dual track, not only our monetization strategy, but also making sure that we get the product feedback to the appropriate folks on the team too.

[00:24:23] just shared a minute ago that I really loved was this idea of you have to be deep in the vernacular of the company. And I'd be interested in hearing about how do you do that? What are you asking for? Or what are you asking a meetings or what is the way in which you learn and figure out the vernacular of the company?

[00:24:43] It's a combination between. Your research around a company. And also just the questions that you're asking when you're live. And I think it all boils down to active listening and then being able to tie that back in, we've had a bunch of deals that loom recently where the icing on the cake is value alignment.

And it's literally us either, frankly, doing diligence on someone's website and getting an understanding of what their approach is and how do they think about articulating values for their organization and them doing the same with us at loom, there are key initiatives. If it's a more formal pilot that usually have a specific name and have a specific set of departments, it's making sure that if you're talking to a design team or a product team, you've started to pick up the ways in which they talk about.

They do a one-on-one. So they're doing stand-ups or they're doing code reviews. What are the things that they use to describe their day, their week, their operating cadence as a business, and when we're spitting back. Those use cases where we're spitting back. Those examples are when we are bringing someone net new into the conversation and talking about the current state of where we are with loom or Quip or Dropbox's deployment.

We want to make sure that that feels as organic and natural and integrated into the way that they not only talk, but think about their world as a member of that company as a member of that community. And so ultimately it's how do we just feel like we're a partner in the room? That's there almost as a consultant versus someone that's just talking about their service.

And I think common language is a really powerful way to do that. Are there 

[00:26:19] any other questions that you often lean on when you're trying to learn about the vernacular or the way in which a company operates, or if you think about the last month when you met maybe with an enterprise customer for the first time, how you're structuring that time to leave with the largest number 

I learned this from Molly at my time at Quip and. There's a lot of power in saying you don't understand or don't know something being willing to ask the dumb questions of just like, Hey, you mentioned X, Y, Z thing. I don't know what that is. What does that mean? And it could be, oh, that's the way that we talk about this workflow with our engineering or EPD team.

I think approaching with curiosity and approaching in a genuine way where the questions just come from a place. Understanding and therefore feel less intrusive. I think the art versus science component of a sales motion is how do you do that tactfully in a way where you're not overstepping, but I think the most successful salespeople that I've seen are able to ask those next level questions.

And they're just doing it in a way that feels naturally curious versus, Hey, they're trying to check a box on the list of questions they walked in the door with. And so thank you, Molly, but I think ultimately it's how do you kind of put the ego aside? You can go, I don't know what you're saying. And, and I think that there's a lot of power in that.

And so maybe it's just my style that I've adopted, but something that I've tried to infuse in the team is how do you bring levity to the conversation? How do you fall on the sword or put your ego at the door or call it whatever you want. And I think that being super genuine and having that level of curiosity has just unlocked some great conversations and have led to ways.

We're talking about stuff. We're at the top of the hour, when you set the agenda and you were planning how to spend that 30 or 45 minutes together, you didn't expect to be going in this way. And ultimately that's the really good stuff that you can begin to tie back into and speak that common language on.

[00:28:16] gears and pick up a thread. You talked about a little while ago, which is the way in which sales and product fit together. And you were sort of talking about it specifically at loom, the way that you work with your product counterpart. I'm curious how the two of you coexist and collaborate and maybe ultimately how that leads into and informs ultimately what gets built in 

What's our common goal and TLD is the common goal. Total loom domination. This is our joke internally of like we've got really big aspirations for what we think this could mean in terms of addressable. Knowledge worker population that's using loom and it's a broad opportunity. And so if we have alignment from the get-go of like, we want to grow and a by-product of us growing from a user perspective, from an engagement perspective, there's an element of on the revenue side.

Like my life is going to be a whole lot easier. If we have an entire market that's seated with heavily engaged and delighted LUME users. And so those first sets of conversations were around. What are we here for? And why are we excited about this opportunity? And what's our common ground that's there.

Okay, cool. We've got that box checked. The next piece is how do we start thinking about team interaction, but also goal alignment and something that, uh, Nick and I were really intentional about at the beginning is making sure that we had strong counterparts on either side of the house, from my revenue organization and her product organization, where there's sometimes clear lines on who owns what?

And there are also times where. Yeah, it's going to be kind of muddy because it's sitting right in that triumvirate of product marketing sales, it's kind of somewhere right in the middle of who's really driving this initiative or this release, whatever they may be doing. And so I think there's also been just some really healthy conversations going eyes wide open on it's going to be messy.

Like the known quantity is going to be that it's messy. And how do we just continue to put checkpoints in place where we're reinforcing each other around what we're trying to do? And we go from there so very table stakes stuff, but the team alignment and goal alignment at the beginning is important.

The next phase, though, for me, when I'm thinking about the way that we structure, particularly the revenue organization is we have self-service revenue as well as our sales lead revenue. Rolling through me, I guess is the way to put it an important distinction there though. What's good for our self service business.

In this episode with Sam Taylor, we get super tactical with the lessons he’s picked up from his career as an early sales leader at top product-led growth companies — Dropbox, Quip and now Loom.