“Everyone wants a silver bullet” — Selling lessons from Sam Taylor, of Dropbox, Quip & now Loom
Episode 29

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

Today’s episode is with Sam Taylor, VP of Sales and Success at Loom. Previously, Sam was Dropbox’s first enterprise sales rep, and also served as Quip’s first sales leader. In today’s conversation, we dig into the key learnings from each stop in Sam’s career so far.

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Today’s episode is with Sam Taylor, VP of Sales and Success at Loom. Previously, Sam was Dropbox’s first enterprise sales rep, and also served as Quip’s first sales leader.

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 Bret 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 Loom’s product leaders, and how they’re teaming up to achieve what he jokingly calls “total Loom domination.”

If you’re in sales, you won’t want to miss Sam’s insights he’s picked up over the course of multiple startup 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 fits in.

You can email us questions directly at [email protected] or follow us on Twitter @ twitter.com/firstround and twitter.com/brettberson

Sam Taylor: [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?

Brett Berson: [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.

We've shared standout company, building advice, the kind that comes from those willing to skip the talking points and go deeper into not just what to do, but how to do it with our new podcast. In-depth you can listen into these deeper conversations every single week. Learn more and subscribe [email protected]

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. 

Sam Taylor: [00:03:32] Likewise, thanks for having 

Brett Berson: [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 

Sam Taylor: [00:04:26] product led.

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. 

Brett Berson: [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.


Sam Taylor: [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.

Brett Berson: [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 

Sam Taylor: [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.

So unpack 

Brett Berson: [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. 

Sam Taylor: [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 

Brett Berson: [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 

Sam Taylor: [00:17:47] what you landed on.

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 

Brett Berson: [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 

Sam Taylor: [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.

One of the things you 

Brett Berson: [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?

Sam Taylor: [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 

Brett Berson: [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 

Sam Taylor: [00:26:35] of insights?

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.

So let's flip 

Brett Berson: [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 

Sam Taylor: [00:28:36] what order it starts.

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.

What's good for a more efficient way for us to be monetizing is good for the overall business. But also for me, when I think about it from a trade-off perspective, I'm not feeling that rub within our organization or teams between crediting or anything like that. So how do we structure our teams in a way where we have overall goal alignment, that's there as well.

And then finally is you got to add a dash of luck and the dash of luck component of this is a Nick is a really commercially oriented product leader. She wants to build a business. She wants to build a product that is valuable to these businesses. And so she's leaning in a huge way, right? From the get-go around wanting to be engaged with our customers, wanting to seek product feedback in a formal way and wanting to make sure that we're keeping our finger on the pulse for.

Where people are both finding value, but also experiencing gaps in our offering. And we've been able to put a really nice cadence together between our teams there. We recognize that the sales lead team that we have today is small from a headcount perspective. And what that means is just the number of data points, the number of conversations that they're having on a weekly, monthly basis.

It's just a different order of magnitude versus the insights that we're going to be gleaning from our 10 million users that are on loom today, or even other customer facing teams like our support organization. And so we've actually broken out our sales lists. And customer success feedback sessions in one cadence.

And we usually have that on a monthly recurring schedule, and it is everyone on the sales and success team, as well as a Nique and all of the PMs that are building the product. And we give structured feedback around what we're hearing, what we're blockers, what we're value drivers, what are the volume of conversations that are reinforcing this?

What are the dollar amounts that are associated with these opportunities? And so how do we start to weight and right-size that smaller dataset. And then on the flip side, our support organization, because of the scale at which they're triaging customer feedback, and also has more structured ways that they are tagging these different conversations that are taking place a much more volume-based feedback loop, that's happening to a NeoCon team on a more frequent cadence there, I think it's every two weeks at this point, 

Brett Berson: [00:33:00] how do you prioritize the needs of the downmarket customer base?

That's obviously more self-serve. With the needs of the 

Sam Taylor: [00:33:11] enterprise. Right now, we just have a healthy look at what is our current and aspirational split of the contributions from each of those different functions or revenue streams. And we try to make sure that our resourcing is in alignment with that.

And so back in the napkin, if we're saying, Hey, we expect 80% of our revenue to be from self-serve and we've got 20% that we think is going to come from our sales cycle organization. And within sales lead, we expect half of that to be SMB and half of that to be up market. Then how do we start to think about those?

High leverage opportunities for improving the product that we'll probably have a healthy trickle down effect. And so I think we benefit from the fact that if you're building something, that's going to be rock solid from a security and administration perspective for a multiple thousand seat deployment, probably going to be a lot of goodness in there for a multiple hundred seat deployment.

And so how do we think about that? Right. Upper bound for where we are with the customer conversations, where we are with our pipeline and the feedback that we're getting in the sales led front. But even now we're still talking about that 20% of product capacity, because we're not losing sight that that end-user experience for that individual that's on loom or that small team that's on loom is so paramount.

To driving and feeding our upmarket motions that we want to make sure that we're continuing to innovate and drive delight for really where that majority of revenue stream and majority of user base is always going to set for us. 

Brett Berson: [00:34:41] How do you you're out that split? So let's say we're thinking about over the next 12 months or maybe 20, 22, what should our split be between enterprise and self-serve?

Sam Taylor: [00:34:51] don't think there's ever a should, could I think there's a what's happening today, but the way that we're looking at this is in terms of investment and we're in a fortunate situation at loom where we're having a lot of growth in a short period of time, both from a user perspective, but a revenue perspective and keeping pace with the split.

Is aggressive because the scale and speed at which we are growing, our customer facing teams is tough to keep up with the pace at which with the scale and speed with which our self service business is growing. And so we think about it in terms of where are we today and where do we aspire to still have those revenue breakdowns a year from now?

It's easy to say like, Hey, we're keeping that 80 20 split, but when the numbers are growing the way that they are, those raw numbers of what each of those different revenue streams are producing, that's a lot of lifts that can go in on the sales side. And so I'd say we are working closely with our operations team to think through hiring plans, but hiring plans that are thoughtful and that are in line.

All of the productivity metrics and rent metrics that you would expect for both a sales and customer success team over time. And I think that we're in a really fortunate position where we don't have to just throw bodies at the problem. We can do it in a thoughtful way. And I think a exciting time for us at loom right now, where we are seeing are sellers that have been in seat now for nine to 12 months.

On average, we literally stood up a sales team for the first time in June of last year, as our product was coming out of beta, our limps for team product. And so a lot of learnings have impacted in the last 12 months. We just executed on our first two renewals as an organization, which gives you a sense of how early we are in the maturity of this motion for us.

And we're going to continue to push on it and be aggressive as we can to keep that split as healthy as we can. What do you continually 

Brett Berson: [00:36:47] find tricky about the surface area of work that you've seen. A lot of time on over a number of companies, this kind of interplay between product and sales, self service and enterprise product led growth.

What are the things you continually wrestle with given the amount of experience that you have 

Sam Taylor: [00:37:06] in the category? Everybody wants to 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 of just like, Hey, here's the one thing. If you tell someone to use loom for this, they get it, or Quip or Dropbox or any of these. And the wrestle has been, if you have an opportunity like we do at loom where we view our Tam is anyone that uses email.

That's the way that we think about our addressable market, which is massive. And through that, if you try and go with a generic. Hey, loom can be used by anyone for anything or Quip or Dropbox, which is true. It falls flat. 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 and where do you, whether it's data-driven or if you're not in a place where you have that data yet, what is your intuition saying that you should be trying?

And so I think the part that keeps drawing me back to this phase, but also these types of organizations is the experiments mentality that you have to approve. Your role with, cause it's fun. We all have that all figured out. It isn't a clear who is the exact persona, exact use case, exact thing that you're targeting your product with.

And something that I really enjoy as a revenue leader is the messaging, storytelling and experimentation that we get to do as a team because of this. And we're in a really fun phase right now where we're getting to try a bunch of stuff and it's fun to see heads nodding and stuff, starting to land. It's fun to see, Hey, that didn't work so hot.

Didn't work so well. But ultimately I think that the struggle will always be trying to figure out what is that one thing or one person that's going to be your ICP. And the reality is it would be too narrow to try and approach it that way. So 

Brett Berson: [00:39:07] on that point of experimentation, could you maybe walk us through, when you think about the last six months, maybe one, two or three experiments that you ran at your domain and maybe one that worked or one that didn't or one that led to a really crystallized insight, that's been really valuable for them.

Sam Taylor: [00:39:24] Recently, we are looking at different ways that we can activate our users in our onboarding flows. And so not in my purview, but something that's happening on the product side of the house is just different onboarding experiments with the product. We also have an assist team that is basically, we've got some folks that are engaging directly with our users, whether it be in the product or via chat.

And we're looking at ways that we can understand onboarding and where people have pinch points there. So one of the experiments was actually just having for a certain cohort of our users, an onboarding coach that was literally one of our roommates on chat, trying to engage and help you have that aha moment.

I think the fascinating learning there was folks really have specifically. Ways that they are thinking about loom from a use case perspective as they enter into our product and into our product experience. And then ultimately when we think about, are we able to move the activation needle with that limited number of conversations with that limited cohort, we had a lot of insights and learnings.

We didn't have anything that was stat SIG of what should we productize coming out of it. But an example there is just around how do we help lead people to water and be there as a resource live, almost similar to in a much more targeted way, but what superhumans been doing with their onboarding experience as well?

We're trying to have a flavor of that. No key insights that were there, an experiment that we're running on the go-to-market side right now is persona based outreach. And really trying to target who do we think are the folks that are going to be on the forefront of making a decision around what are the workplace culture and strategy drivers for their foreseeable as everyone just kind of entering into.

What is this next phase of our workforce going to look like who's tasked or who do we think is put in a position to have the opportunity to make those calls? And how do we start to position loom as a vector or a change agent for those employee empowerment conversations, those flexibility conversations and those workplace investment conversations, and so fascinating to see where it's resonating and where it's not, but very persona based targeted outreach based on current environment in the world today.

So those are just two examples of what we're doing right now at loom. 

Brett Berson: [00:41:41] When you think about enterprise sales on top of product led growth, do you always only sell into existing customers that have come in bottoms up or is there a role for more traditional outbound or more traditional sales outside 

Sam Taylor: [00:41:58] of that?

It all boils down to phase. And so in a similar way, Joining Dropbox early on, and you've got your sales capacity overwhelmed with inbound. Excellent. I think the area where it gets hard from an investment perspective is that moment or that time period, where perhaps that inbound demand begins to wane and how long it takes to actually stand up a true outbound organization, which traditionally, if you're really trying to get that thing humming 18 months, if you're really starting to have repeatability and an understanding there.

And so when I think about the marrying of the two or that moment, it's when do you have enough consistency in the conversations that you're having, the company profiles, the personas, the buyers where's that repeatability there, where you have confidence in being able to go out and target mimic accounts.

And so at loom today, we are seeing a ton of engagement with design organizations and we're seeing them use loom overlaid on tools like Figma or other ways. Loom is being put into their workflow and feedback loops. And so we have a bunch of inbound demand, but we're also beginning to point our outbound marketing efforts as it relates to round tables, panels, content that we're putting out there.

Sales development team is starting to reach out to other design teams within similar style companies. And we're also just using the amazing roommates that are on our design team as well, to push into their network and see if there are folks that we should be engaging with too. And so ultimately it's around the pattern matching.

And when you have confidence in the repeatability, you have repeatability, you can start to put some structure into the air quotes, plays that you would want to run. And then through that, you can begin to build that warm outbound. I will call it as opposed to are we just buying a phone book and calling down it we're definitely far away from that.

And I think that that's the beauty and opportunity of our model is if we continue to drive signups the way that we do, we should have a pretty consistent drip of product qualified leads and areas of opportunity within the user base. 

Brett Berson: [00:44:08] One of the things that I've noticed across a lot of mature companies is a lot of times in this path to either layer on enterprise, go up market.

Take product led growth, bottoms up adopted product, and then layer in top-down sales is either culturally or from a timeline it's almost like too little too late, or they struggled to do it excellently. And I'm curious, have you noticed that or are there ways to allow these two things? So ultimately co-exist as opposed to a bottoms up adopted product with relatively crappy enterprise sales or broken enterprise sales, or what have 

Sam Taylor: [00:44:51] you?

I think the cultural component is one of the hardest things to navigate when you're standing up that team. And I think that one of the things that's always difficult as you go through any of these growth phases or as certain teams or departments begin to evolve. And ultimately scale is the transition in the hiring profile from those foundational members of the team that are going to be.

The true believers on the mission side that are going to be saying, Hey, point me towards the fire. I'm stoked to run into it because I'm a sicko. I love it. I love building. I love doing it. I love, I love, and I put myself in that category of why I keep seeking out opportunities and companies that are in this phase.

And I think that the reality is a lot of folks that have made it in their careers to be excellent enterprise sellers. There's just a different level of structure. There's a different level of approach. And ultimately there's an expectation of being able to have that repeatability and have that repeatability in those deal cycles.

And at the scale that justifies the resourcing that goes into it. And when you've had a PLG motion, that's been serving you well for a long time and feeding. Velocity sales that are less resource intensive and perhaps much more gratifying in the sense that these deals typically close in a much shorter timeframe that shifts towards oh wow.

We're, we're hiring folks that are more senior we're hiring folks that wait, they haven't closed the deal this month. What's going on. What's wrong. There can be questions that you really have to get ahead of as a leadership team around. What's the goal, what's the timeframe in which you expect these teams to become productive.

And why is it worth the investment now looking forward 12, 18 months of where you expect to be and where you hope to be layering in a net new revenue stream on top of whatever you've been optimizing and delivering on to date, and that's really hard to navigate. And so I think for the teams that do.

Well, and what I like to say are the teams that I thought that particularly at Quip, we really had a strong enterprise sales motion that we were able to execute on pretty early on in the company and the piece that integrates and ties all of that together is executive team buy-in. And specifically, when I think about Brett at Quip, Brett wanted to close enterprise deals and he was excellent at being in that room, being an evangelist at an exec sponsor and at sometimes even deal driver for those opportunities.

And so really when you think about the resourcing and you think about the cultural component, if you've got your senior leadership bench that is wholeheartedly wanting to take part in this investment, and those teams become fully integrated into a team selling motion with those exec sponsors, that's where I see it done.

Well, trying to put an enterprise motion where it's oh man, we went and hired all the salespeople. Things have changed. Oh, well, hopefully they do well, having a disjointed in that way from a cultural perspective where it's viewed as, oh, the company shifted in a negative way, or, uh, I guess now we have to start talking about ACV or MRR in the way that we didn't have to do so before there can just be stigmas and negative connotations around layering in a air quotes, more traditional B2B sales organization.

And I think that those companies where it is fully embraced and resourced all the way up and down, not only the leadership chain, but cross-functionally is where it becomes just a net new part of the family and something that breathes more life into the area of opportunity for their Tam. On the point you just 

Brett Berson: [00:48:44] made about Quip, I think a bit earlier, you also saying that interestingly, it was a product that was less bottoms up adopted or product led versus maybe something like loom.

And I was curious if I got that right. Why do you think that was, or. 

Sam Taylor: [00:48:58] I think every company that's appealed to you company as an onboarding company and the code that we never fully cracked with Quip as an independent organization. And I was only there for 18 months while we were pre-acquisition was how do we take all of these folks that are entering our product experience in so many different ways, from a role within the company expectation of what Quip is, all of the things that make it difficult to sell a horizontal tool.

And I think that we struggled with how do we get people activated in a way that led to consistent and meaningful adoption of the product. And so ultimately that meant that we had to do a lot of handholding with our salespeople and with our support folks and the nature of loom as a comparison, very lightweight, relatively simple from a UI perspective and.

You just press record and you go. And I think that the barrier to entry for the behavior change is a lot lower with loom. That being said, we are still on the forefront of all of us getting comfortable with video as a medium. And that's something that we're continuing to push on as collectively a go to market team, as well as product organization.

How do we help normalize and reduce any friction that's there? But I think for Quip in particular, we found that we were able to do that same level of handholding as it related to someone having their aha moment around the product itself. Aha moment around the value that it could drive for their organization, but because we were doing so with so much of our human.

And team resourcing, ultimately what justified that level of handholding were larger and larger deals. And so from a breakdown, when we were talking about where is the error coming from, we were definitely lopsided even very early on at Quip towards larger sales led enterprise organizations from a revenue perspective than we were with our self service business 

Brett Berson: [00:51:02] a moment.

So you'd said something pretty awesome, which is every PLG company is an onboarding company. And you've talked a little bit about onboarding as it relates to the assist team. And some of the things that you learned about activating folks at Quip, are there other insights or best practices or ideas that you figured out around what great onboarding looks like?

Sam Taylor: [00:51:25] I think the ethos just has to be, do you have an understanding of the different categories? Of the jobs to be done with your product. What are the commonalities that are there? And then how do you find ways that you get people to have the lights turn on regarding, oh, I can apply this use case, this workflow, this behavior change.

And it's going to benefit me by using this product. And I think that the opportunity that we have with loom is particularly with me being an employee now for a number of quarters I joined in October of last year. And even just seeing the varied ways that my own use of the product has evolved as I've become more comfortable, more confident and engaged with the platform as a user and as an employee.

We have to lead people to those understandings and we have to do it in a condensed way. And so I think the challenge and opportunity on the onboarding side is ultimately how do you start to find ways if you have a large user base to begin to cohort users or bucket them, even if it's broad categories to make what you are spitting back or leading them to relevant.

And the truth of the matter is like sometimes it has to do with them being in a certain type of company type of role. But other times you just have to submit to, if you're a human being and you work, you do these things and we should talk about those things regardless of who you are, and we should try and make it.

Authentic and experience as it can be. And so I think that for us, when we think about loom, the interesting part that we run into right now on the trade offs, if we will, between the different use cases that we have, when we bucketed into two things like those that are creating the femoral content. So probably send, it gets washed once or twice.

No one watches it again, or evergreen content. Hey, I'm putting something on. My support Wiki or I'm publishing a formal update or something that's going to live on in terms of strategy, something that will be revisited again. How do we start to get people into those two different modes around tshirt?

Like we have editing tools. We should probably lead people towards a higher level of Polish if they so choose. And also the good stuff is just say what you got to say, show what you got to show and send it to someone and be authentic and be real and express yourself. And that's what I love about it. Our onboarding plans really go into those broad categories.

And then how do we do things from a product perspective, lifecycle marketing perspective, a user education perspective that get people comfortable with the behavior change as fast as possible. 

Brett Berson: [00:54:01] So I wanted to end our time together by talking about some people related topics. And the first one I was really excited to get your perspective on is I'm sure you have tons of founders that reach out to you either to recruit you or to get your advice on their first sales hire.

I was really interested. There's a lot of advice or perspectives on first sales or go to market person for more traditional go to market motions, but I'd be really interested to get your thoughts on you. Take the average founder that reaches out to you. Maybe they have a million or a million and a half in ARR, basically bottoms up.

Founder led. Product led or adopted software. And they're like, we're hiring our first person to focus on, go to market or sales. What advice do you give them? Or what's your framework or coaching that you provide in those types of conversations? 

Sam Taylor: [00:54:49] I have a lot of those conversations and I welcome them. I love it.

If you're putting the parameters of Brett, a mil mil, and a half error, I'm assuming that we're starting to circle around, Hey, maybe there's some of these customers that are growing organically via self-serve that are sizable enough. We want to see if we can up level those, or we've got sizable penetration at a domain level or within a company that we think warrants trying to standardizing and collect that.

The advice that I give is, well, I start with a lot of questions and ultimately I think it was down to the phase of what are the size of opportunities that you're expecting this person to close. I've been amazed at some of the smaller companies. Have offerings that they're able to get into low six figures or tens of thousands of dollars in deal size for a relatively small team and a relatively new offering.

But when you start passing those budget thresholds, it changes who's across the table from you. And it changes the level of rigor that you may need to approach that sales cycle with. And so there've been times where I'm actually surprised that there's a PLG motion and the natural pairing of where the sales team should be focused is way up market.

And that is less common, but it changes the profile significantly. The advice that I give and when I look back at the top performers at Dropbox at Quip, and even who I'm seeing be successful at loom it's folks, Can come with some sort of sales background. So I advise folks to engage with people or recruit people that have had some sort of closing experience in the past.

Particularly if you have a founder that maybe is on the technical side of the house, where maybe it just hasn't carried a quota themselves in the past, you want someone that has an understanding and comfort with the motion, the process, and the inputs that are required to ultimately get to the outputs that are going to be tracked.

The advice I really drive on though is going deep on cultural ambassadorship as a founder led sale more times than not heading into this. And this is going to be the first time that you're going to have someone that is not the founder being that physical human representative of your company and your brand.

And so making sure that you're going deep on the why of why this person would want to join your organization and. Also ensuring that to set that person up for success, you're in a place where the value proposition, the sales motion that you would expect this person to deliver on. And the storytelling that's required to convert these customers is something that someone other than the CEO is going to be credible saying.

And I think that that is a real. At least I've seen the light bulb go on for a number of folks in these conversations where they suddenly realize, oh man, like let's use bread as an example, easy for Brett, uh, as former CTO of Facebook to stand in front of a room and talk about future of work and where he sees things going and the vision that he has, if I try and stand up and regurgitate that as one of the first sales people on the team, I'm not the founder.

I don't have the background and the credibility that he has. I can't say those exact same words, the exact same way that he's saying it and move the needle in the same way. And so I think a big area of focus in these conversations is around, yes, there's the hiring profile. And you want someone that I always say would, err, on the side of, is going to live and breathe your mission and is going to live and breathe your brand and is a true believer in your product that is going to take you farther earlier days than someone that is a hyper established salesperson in my view, because.

It's both ARR, ACB, whatever the revenue metric is, as well as the insights that are so, so valuable at that phase. And if you're over rotating for someone that is chasing a W2 or thinking through I'm in sales, because I'm just focused on the quota carrying capacity of this, that is not the foundational member of the team that you're going to be looking for and recommend that folks just make sure that they're filtering for that.

You've had 

Brett Berson: [00:59:08] the opportunity to work with some really incredible leaders and CEOs in your journey across your last few companies. There, are there specific insights or concepts, frameworks, ideas that they've shared with you or inspired in you? That's part of your operating principles 

Sam Taylor: [00:59:26] today? One that jumps out right off the bat was joining Brett and Molly at Quip early days.

And Brett was very open in talking about what the goal of the company was. And the goal was. This is going to take a decade plus, and we're going after Microsoft as a way that we're going to display, like what should the new productivity suite look like? And that's the goal. So talking about like having a very large winning aspiration, that's a massive one.

The interesting trickle down effect and learning from that though, was seeing culturally how you structure a team, but also how you structure the cadence with which you operate, knowing that it's going to be for the long haul. And I think that the example that was driven and I think it had a lot to do with the life phase that Brett was in, he was still in family building mode.

When I was interviewing, he was actually on paternity leave. There was just an ethos around. We want to hire folks that are best in breed of what they do, and then give them the autonomy and the flexibility to live their lives and help us grow an amazing long lasting company. And I think that perspective changed for me, particularly coming out of how quickly we were growing at Dropbox and just the pace at which we were growing.

My initial reaction was, oh my gosh, we're at odds with what it's going to take for us to execute and do what we need to do. But my quick learning, particularly with the potency of our engineering team at the time was when you hire folks and you're intentional around trying to only bring 10 X-ers into your organization for whatever role it is that they're coming in, you can move.

Mountains with a very small team. And that was the really cool learning for me with Brett was you can be in it for the long haul. You don't have to burn people out, but it doesn't mean you have to give up operational and execution excellence if you're bringing in the right team. And so it was really kind of a fortifying learning around being really intentional and choosy with the people that you choose to go on the ride with and ensuring that everyone's going to be culturally additive, but also pulling more than their weights so that everyone can go execute on that.

Awesome. Well, I think 

Brett Berson: [01:01:36] that is a great place to end. Thank you so much for spending all this time. 

Sam Taylor: [01:01:41] Thank you for having me. It was a pleasure chatting with you.