SaaStr Podcast #403 with Loom VP of Sales Sam Taylor

Ep. 403: Sam Taylor is the VP of Sales and Success @ Loom, the startup that helps you get your message across by making it easy to record instantly shareable videos. To date, they have raised over $73M from some of the best in the business including Sequoia, Kleiner Perkins, General Catalyst and Point Nine to name a few. As for Sam, prior to Loom, Sam spent over 4 years at Salesforce following their acquisition of Quip, a startup Salesforce acquired for $750M where Sam was also the 1st sales leader. Before Quip, Sam spent an incredible 3 years at Dropbox where he was the first enterprise sales rep in the entire company.

In Today’s Episode We Discuss:

* How Sam made his way into the world of SaaS with Dropbox and how that led to his leading the sales and success team today @ Loom.
* What was Sam’s biggest lesson from scaling the sales team at Dropbox? How did his 4 years at Salesforce change his operating mentality? Thinking of Dropbox, how does Sam justify the role of sales in a world of product-led growth? How do product and sales work together most efficiently? What can one do to structure that relationship?
* Does Sam agree that the founder is the one who has to create the sales playbook? When is the right time to hire the first sales rep? Should you hire 2 at a time? What does one look for in their first sales hire? What measurements should be used to determine their success? How does this change when selling to SMBs vs enterprise?
* How does Sam think about the relationship between sales and marketing? Are marketing becoming the new sales team with their content being used more and more in the sales funnel? How should the success of marketing be measured? Does it have to be tied to a number related to revenue?

If you would like to find out more about the show and the guests presented, you can follow us on Twitter here:

Jason Lemkin
SaaStr
Harry Stebbings
Sam Taylor

Below, we’ve shared the transcript of Harry’s interview with Sam.

Harry Stebbings:

This is the official SaaStr Podcast with me, Harry Stebbings. Today, I’m joined by an awesome guest, such a unique set of experiences from Dropbox to Salesforce to Loom. And so I’m thrilled to welcome Sam Taylor, VP of Sales and Success at Loom, the startup that helps you get your message across by making it easy to record instantly shareable videos. To date, they’ve raised over $73 million from some of the best in the business, including Sequoia, Kleiner Perkins, General Catalyst, and Point Nine, to name a few. As for Sam, prior to Loom, he spent over four years at Salesforce, following the acquisition of Quip, a startup Salesforce acquired for $750 million, where Sam was also the first sales leader. Before Quip, Sam spent an incredible three years at Dropbox, where he was the first enterprise sales rep at Dropbox, such an incredible journey there.

Harry Stebbings:

We’ve had quite enough for me. So now I’m delighted to hand over to Sam Taylor, VP of Sales and Success at Loom.

Harry Stebbings:

Sam, it is so great to have you on the show today. I’ve heard so many great things from our mutual friends, Joe Thomas, obviously at Loom, and then also Carl Perry. So thank you so much for joining me today, Sam.

Sam Taylor:

Thank you, Harry. Pleasure to be here.

Harry Stebbings:

Well, I’m very excited for this one. But before we dive in, I do love to context that a little bit. So tell me, how did you make your way into the world of SaaS? And how did you come to lead the sales and the success team at the rocket ship, and one of my favorite products, being Loom?

Sam Taylor:

I can tell you, it was not a straight line. I’m a California kid from the Bay Area. I studied environmental science and played hoops at a liberal arts school called Bates College. And I stayed in that track for a while. So I was doing environmental consulting. I worked in solar. I worked in semiconductor before getting into the tech side of things. And I was over rotating heavily on stuff. I even joined the hazardous materials waste cleanup crew at one point for a hot second. That’s a whole different story. But I got an introduction from a former colleague to Salesforce, and that was about a decade ago in 2010. And that really was the turning point for me going on this ride I’ve been on for the last decade.

Sam Taylor:

And so, I joined as a sales development rep at Salesforce, best move I ever made. I met my wife in sales boot camp. We were hired into the same role, same start date, competed head to head. She kicked my butt in every metric you could possibly imagine. And so, I ran over to the Dropbox. I’d been ignoring them. I was reached out to by a recruiter there. I was too busy chugging Kool-Aid at Salesforce. And upon meeting the team, I was just blown away by the people. I had an opportunity to be one of their first five sales reps. The company grew from 60 to 1500 people over a three and a half year period. And so, I got to just grow up, if you want to put it that way.

Sam Taylor:

On my first leadership role, I was the first enterprise sales rep, a manager of mid-market team. And during my time there, one of my close friends and mentors, his name is Steve Carpenter, gave me a nudge and said, “Hey man, when are you leaving?” And I’m like, “What are you talking about? This is off to the races.” He said, “It’s time for you to go learn some more.” And so during my enterprise days, I had closed a large deal with Facebook and somehow ended up on a list of people that the Facebook team had enjoyed interacting with. Quip was founded by Bret Taylor and Kevin Gibbs. Bret was formerly the CTO at Facebook. And so, they actually reached out to the Facebook folks, asking for salespeople they enjoyed engaging with, and I was on that list.

Sam Taylor:

And so, I met Bret. I met Molly, who was the COO at the time, Molly Graham. And it was just a step function change. And I’m going to learn a ton from them. Let’s go do it. And so I was their first sales leadership hire. This was in early 2015. We were acquired by Salesforce 18 months later. So I’ve been building the commercial team at Quip internally there. To keep my head in the startup game, I’d always been advising, engaging with early founders. I saw the Series B funding announcement for Loom last November and just had this crazy aha moment around the mission and the product. They just made a ton of sense for what they’re trying to solve. And so, I texted Ilya, who’s the partner that led the A at Kleiner. We worked together at Dropbox. I haven’t talked to him for like five years. It was like, “I want to learn more. I want to meet Joe.” And Joe being the CEO of Loom, we were off to the races and we’re staying in touch throughout the year. And 10 months later, here I am.

Harry Stebbings:

So I do have to ask, though, Sam, because you mentioned some incredible companies there, from being first enterprise sales rep record at Dropbox and then also to the time at Salesforce and such instrumental times of growth for those companies. If we take them one by one, what were your biggest lessons from scaling the team at Dropbox? And how do you think it maybe impacted your operating mentality today?

Sam Taylor:

So no matter what, I mean, Dropbox, no matter how you slice it, what function you’re in, was just insane from a growth perspective, headcount-wise, user base-wise, you name it. But I think for me, the interesting lesson was on how to place go-to-market bets, sitting with and understanding how uncomfortable that can make you feel. And ultimately, just how you have to have a bias for action and ultimately be charging forward in that way at all times. And so for me, I’d say the early learnings were tough to have. Our sales team was closing 50 deals a rep a week at times. And so, there wasn’t a lot of feedback in the moment around gaps that you have.

Sam Taylor:

But fast forward a year into the job, and I move over to the enterprise role, and it’s literally just like pulling the emergency brake on everything. It was our first time going outbound. It was myself and Kevin Egan, who we had hired from Salesforce to be our VP of outbound sales. We were just sitting at a table at an indeed road desks and went, “Well, I guess we should make a deck.” And so for us, it was placing bets on target accounts, buyer personas, sales messaging, and we really didn’t have any historicals. And so, as you can imagine, some of it landed, most of it didn’t early on, but we skipped the whole go from SMB to mid-market to enterprise and just went SMB transactional right after the Fortune 500. And so, right,wrong, or the other, it was an amazing lesson in learning to iterate quickly on the fly and just, you got to make a call, get in motion and be comfortable with making changes along the way.

Harry Stebbings:

Can I ask, I’m sorry, this is off schedule, but often people say, “Growth simply solves all problems.” You saw such incredible hypergrowth at Dropbox. Is that something you agree with, or it’s something where you go, “Well, actually, things break when you grow as fast as they do. That’s a little bit nuanced”?

Sam Taylor:

It’s definitely nuanced. I mean, stuff is broken everywhere. I mean, you look around, process is broken, communication is broken. It is fundamentally flawed. But ultimately, you’re also having this sense of winning. And so it’s almost that winning masks everything. I’ve seen that in my athletic career on the basketball side, where it’s like, “Hey, we’re putting together a solid winning streak. We’re getting it done.” There’s definitely things that need to be addressed that aren’t perfect with the dynamic of the team, but you’re able to mask over a little bit of that because of the macro success that you’re having. And so I think there was definitely an element of that at Dropbox too.

Harry Stebbings:

And then, again, sorry, I’m completely getting off schedule, but I’m too interested. When you think about onboarding enterprise sales reps, the challenge is [inaudible 00:06:57] the sales cycles are so long and you can lose confidence when you’re new in a company and the cycles are as long as they are. How do you think about building confidence in those tweener months? And do you advise and recommend, “Hey, close a couple of logos as fast as you can. It doesn’t matter what the size and build the confidence”? What do you recommend?

Sam Taylor:

I think no matter what, you have to have opportunities to make mistakes. And if we’re just swinging for the fences on the enterprise side, and it’s either a seven figure deal or bust, that’s a big learning curve for somebody. And so, whether it be formal or not, I mean, for the early, early stage teams, we have folks coming in and working, not only support tickets to get a sense of, “How do I solve problems? How do I understand the product itself?” But we also get people going on SMB leads regardless of the segment that they’re there to sell, just so they can get some at bats under their belt as well. You can do a lot of mock scenarios as much as you want. You can enable folks and have as many decks as you’d like. But until you’re having that moment where you’re first forced to go and find information because a customer is asking you for it, we want to front load as many those experiences as possible.

Harry Stebbings:

Totally agree with you in terms of the front loading there. Switching tacks a little bit, you obviously some time at Salesforce and such an incredible company and hailed for many things, but especially its V2MOM process. I’m intrigued, how did those four years change the way you think about scaling teams?

Sam Taylor:

So I’ve been at Salesforce twice in my career. If you could argue, it’s two tours of duty. So when I was there in 2010, the company was about 4,000 employees. When we were acquired in 2016, it was about 30,000 employees. And most recently, it’s around 55K. Honestly, from an individual rep perspective, that order of magnitude scale, there’s going to be no small changes, right? The number of products that are in sales reps’ books, the partners that are in the ecosystem, there’s no denying that. But I was blown away from an operational rigor perspective and the drum beat of just the monthly, quarterly, annual cadence of the go-to-market machine that they have, it didn’t miss a beat. And that’s astounding when you’re looking at six to 10 years with that kind of growth rate. And so my takeaway, it’s tough to absorb it in the moment and it’s more when you’re reflecting on it. You’re basically taught about what does it take to enable a field sales team? How do you get a distributed workforce unified on the mission, the message, the metrics?

Sam Taylor:

And if anything, like I’d say that the key learning for me that’s more applicable in the startup world that I’m in now at Loom is the mission and the message. Repetition does not ruin the prayer. And so making sure that you are constantly layering in the why, and also the way that we want to be articulating what we’re doing as ambassadors for the brand in the field, that’s a huge learning for me. And so I had the opportunity to build a team across North America, and some reps were isolated in their homes, some were in offices. And so really being able to lean back and have that process and that operational rigor allowed us to have success. And I know there’s a lot of eye-rolling that happens when Salesforce is talking about their V2MOM. And for those that aren’t familiar, it’s vision, values, methods, obstacles, and measures, and it’s a planning and alignment process that the company does with a lot of rigor. But as I say, I can’t argue with the clarity and alignment of drives that scale.

Harry Stebbings:

You said there about not missing a beat. I’m really interested because you are absolutely right in terms of that, effectiveness in terms of that planning and sticking to plan. I guess my question is like, how do you think about effective sales planning today? It’s such a tough thing. How do you think about effective sales planning?

Sam Taylor:

Ultimately, it has to be the acknowledgement of the gaps and the risks. And so I think through your planning process, obviously, like any forecast, you’re going to have, “What’s your call? What’s your best case? And what’s your worst case scenario?” And so I’d say, for us, calling out known knowns, known unknowns, and then also making sure that we’re measuring in and putting in enough buffer for ourselves for unforeseen market conditions. Not at the scale of what we’re experiencing this year in 2020. I don’t think anyone had that in their plan. But at the same time, I think when we’re looking from a planning process perspective, it’s how do we look at the speed with which we can get particularly the salespeople ramped and productive, and a huge part of that goes into this drum beat that I was talking about earlier.

Harry Stebbings:

Again, I should never bother writing schedules because I’m just too interested when I have [inaudible 00:10:30]. You said about sales ramp. It’s something I’m really passionate about, which is obviously one of the many reasons I have very few friends. But when we think about sales rep effectiveness, what does it take to minimize ramp time in your experience? Is it a playbook? Is it a very structured process? What can we do to minimize ramp?

Sam Taylor:

So my philosophy on onboarding is here comes a really crappy metaphor for you, but if you’ve ever used Google Earth and you’ve got the whole view of the earth, and then you click in and it does this kind of like crazy warped down to a specific location on the planet, I like to think of an onboarding process that way. And so, when someone’s walking in the door at a new company, so let’s use Loom as an example, they need to learn how to be a Loommate. That’s the internal term that we have for our employees. They need to know what is it to be a member of this community. And so there’s an element of how do you start really, really high up on, what is the mission? What are our values? What is the strategy that we have at the company level? How do you go a layer deeper on what are we doing from a product perspective? Having that as your foundation of just what it means to be a part of this organization and what that stands for is huge.

Sam Taylor:

Then when we’re looking at the actual rep productivity piece of it, I think that building confidence on establishing a point of view is one of the most important things that you can do for a rep. You can train on the feature sets that we have, the value statements we want to make, the decks that we want to train you on. I think reps are truly empowered. It can start really running with their book of accounts and with their customers when they have that confidence to have an understanding. Let’s say, for example, what’s our stance on Loom’s bit in the productivity space, in the collaboration space? How do we play nicely or where do we overlap with other tools that are out there?

Sam Taylor:

And so I think for anyone that’s in a constant state of sales environment, you have to have the perspective that goes beyond the company that you’re in, so you can be credible as a trusted advisor. And so a big piece of onboarding for me is working with our marketing team, working with our engineering product and design team, and working with the other go-to-market functions, just to ensure that we can establish that point of view quickly and then get people out, having meaningful conversations.

Harry Stebbings:

My God, Sam, I do love having you on the show. This is such a fun conversation for me. Again, moving away from the schedule, but you mentioned that in terms of the ramp times. Often, ramps don’t work out. It happens. My question to you is how do you know how long to give them? And my question being like, how much is enough data to know that it’s not working versus too little and they need more time? How do you think about that?

Sam Taylor:

I don’t think there’s a fast and easy rule on output, just because, especially at these early stage teams, you can put your finger in the wind and pick some targets that are out there, but you’re usually not dealing with a deep wealth of historicals that help build that case. And so, for me, I think it is, depending on the segment that they’re hired in, there’s going to be a different kind of range for that view for when we start seeing productivity from an actual deal closed perspective. You mentioned on the enterprise side, yeah, it can take 18 months for sizable deals, so unreasonable to make a call on month three. On the flip side, there are a ton of leading indicators around how structured is this person? How well are they engaging? Are they asking the right questions? Is there activity, meaningful activity, not just for outbounding to their accounts, but what are they doing to ensure that they have a strategy that is sound based on the data that’s available to them? And are they executing on that strategy in a meaningful way?

Sam Taylor:

And I think if you have a lot of rigor around the expectations and the check-in process for how folks are progressing against their plan, the actions that they’re taking, and there’s always going to be that murky zone of the analysis paralysis, right? Everyone’s going a little too deep and not hopping into action. And so similar to what I was talking about as a call-out from my time at Dropbox of just bias towards action, we’ve got to get people in motion. But I think on a transactional SMB or downmarket sales cycle, you’re going to know within probably two quarters if this is really working or not. You’ll probably have those leading indicators in that first quarter when you do that retrospective. And obviously, it’s going to be an extended timeframe for those that are selling at the enterprise.

Harry Stebbings:

Totally with you there in terms of that extended time period in the enterprise, very granular in terms of ramp time and productivity. If we move a little bit up to the teams themselves and how they integrate, especially we’ve got a great product-centric company that we seen at Loom, one of the most product-centric companies. I’m British, so I don’t like direct questions. And so I hope this isn’t rude, Sam, but how do you think about justifying the sales team’s existence in such a product like growth organization when marketing and word of mouth does so much in the sales process?

Sam Taylor:

It’s rude, Harry. It’s so rude. What are you talking about?

Harry Stebbings:

Very rude. How could I?

Sam Taylor:

It’s so rude. Honestly, it’s easy. You just name the fear. You take away that fear’s power and case closed. No, I’m joking. The truth is at these early stage teams that I’ve been a part of, yeah, sometimes there’s confusion around a need for a sales team, a need for the organization. And particularly usually when that first team is getting stood up, it probably is not overtly clear why now for the broader employee population, the rest of the company. And I found in my experience that the path to relevance is its own sales cycle. And you have to identify something valuable that you can package and sell to your customer. In this case, the customer are your new colleagues.

Sam Taylor:

News flash, ATV, ARR, MRR, that ain’t the currency of your cross-functional team that you’re working with and particularly when the product is delivering that on its own. And so you have to ask yourself, “What do we, as a team, have to offer?” You’ve probably heard, Harry, that feedback is a gift maybe in your personal and professional life. But for me, I think taking that mantra around how do we position sales as an ear to the market and how are we delivering market feedback, product feedback, aha moments, adapt in the workflow? How do you take those juicy learnings from the people who are actually trialing, evaluating, and frankly, deciding if the product has value, that’s being delivered to them and then cycle that back to the rest of the organization? I’ve seen that just be an aha moment for a cross-functional group of why sales is valuable. Oh, and don’t forget to hit your revenue numbers. You got to do that too.

Harry Stebbings:

All right. By the way, feedback being a gift, total bullshit. I’d rather [inaudible 00:00:15:56]. I do want to ask, you mentioned there the product feedback being so helpful. I totally agree with you, but it brings me to the cross-functional relationship between product and sales. How do you think about the ideal relationship between products and sales today? I guess for you coming in today at Loom, what have you done strategically, and maybe deliberately, to try and build that in the early days?

Sam Taylor:

For me, an ideal world, we’re waving the magic wand and this is a virtuous cycle, right? Market feedback is informing product improvements, which leads to greater value for the customers, increasing demand, conversion rates are up, right? This is the utopian version of this relationship. I think the challenge with this feedback loop is actually a language barrier. So bear with me here. On average, if you ask a sales team for product feedback, you’re going to get a feature request list. Have you heard the saying of like, if Henry Ford built what people wanted, you’d end up with a faster horse and not an automobile. And so I think there’s an element of that here as well. And so, because that isn’t translating to product, we have to figure out the right way to bubble up the problems that a customer is trying to solve or the gaps in their workflow that are existing.

Sam Taylor:

And so, first and foremost, the awareness of this language barrier is huge, right? And so we need to call it out and put process in place for following relevant data funnel information and insights to the product team in a way that they can digest. So, that’s the first part of it. The added bonus and the holy grail, if we put it there, is getting to a place where this relationship is tight enough, that you are engaging product managers directly with your customers at a pretty consistent frequency. And you would not believe the weight that they carry in a conversation with a customer or prospect. And frankly, it’s awesome. It’s just amazing how forthcoming and willing to answer detailed second layer questions when the folks asking them aren’t carrying a quota.

Sam Taylor:

And so, I can’t speak to what I’ve already delivered at Loom because I’m literally on business day 11 at the company, but I will say the early conversations with Anique, our VP of product, have been around how do we start putting early stage process in place to make sure these feedback loops and lines of communication are open on the team and we already have a V1 of that stood up. And the ultimate goal is also how do we have alignment and sponsorship from the product organization on the deals where it’s going to be a great learning and feedback loop for them, and also going to help accelerate the deals that we’re trying to close.

Harry Stebbings:

Can I ask, in terms of the communications, what’s ideal? Is it a monthly meeting between you and Anique? Is it a monthly meeting between your sales team and the product team? Is it a weekly meeting? How do you think about how often and who should go?

Sam Taylor:

So I think there are two meetings that have to take place at different frequencies. And if Anique is listening to this, I’m not saying we have to do this, it’s just my take. But on the flip side, I think the tightest alignment and the most consistent feedback loops need to be at the leadership level, frankly because there need to be bubble ups of what are we seeing from a [inaudible] perspective. And I would say bi-weekly make sense for this, but also there has to be calls to action. And I think when we’re looking at this at the deal alignment level, two weeks is a reasonable timeframe for those executive sponsorship asks, particularly from sales to product.

Sam Taylor:

On the flip side, at the AE level, we currently have a product manager who’s owning the major milestones for our business offering and enterprise offering embedded it in the team meetings at a weekly basis with the team. And that’s really more for just context on listening around deal reviews and more passive learnings that are there. But I do think there is a monthly cadence between product and the sales team, both for sharing learnings, but also the flip. I think that when you’re in an environment, particularly like Loom, like a Quip, like Dropbox, so much is getting shipped with regularity, that there have to be these formal touch points where we can enable and talk through both what’s immediately on the roadmap, or maybe what is live as well. You wouldn’t believe in previous companies, the number of times that our reps gone into a demo and the UI change has taken place because they just didn’t even know that the thing launched yet. And so, that’s top of mind for us as well.

Harry Stebbings:

Yeah, I’m sure that’s a unnerving situation, I bet.

Sam Taylor:

You wouldn’t believe the panic. Yeah.

Harry Stebbings:

That’s a product and sales team connectivity. The other one is marketing, content marketing. And I think content marketing and marketing have really become almost the new sales teams for a lot of product, like growth companies and products. If we switch tacks to that, how do you think about that relationship and how you should work in an effective way in terms of communications and strategizing with the marketing team, given their role in front of funnel?

Sam Taylor:

So the lines are getting blurred, for sure, especially if we’re making personal purchase decisions or business purchase decisions, the level to which an individual is able to go down the buyer journey on their own is unbelievable. And so I think the handoffs have always been between, in my view, at least, between marketing and sales is when there’s actionable interest or actionable demand. And so it’s that prospect needs to have some sort of back and forth interaction to make their informed decision. And I think the wrinkle today is just how structured and labor-intensive the interaction needs to be. And that’s the call that a sales and marketing team needs to make when they’re evaluating their funnel.

Sam Taylor:

And so if we’re looking at this through the lens of practically growth environment, both sales and marketing have to be tightly aligned on a few things in my book. I think driving customer delight as foundation, number one. Making sure that we are sharing value stories, so we have an understanding of where these aha moments where value is being driven for the customers, but then also just a joint effort and focus on reducing friction to convert. And so they’re going to be times where sales should engage with the prospect right from the jump. And we’re talking more direct sales motion, discovery, demo, trial, the whole works, but it’s not warranted. That is such a crappy experience.

Sam Taylor:

And I know that we’ve all experienced it in our personal lives in making a decision where it’s like, “I just need my question answered, and I’m going to go buy, or I’m not going to buy it, but I don’t need this over the top experience.” And so I think for sales and marketing being really tight on a conversion metrics, where they are choosing to double down and optimize along the way, that informs where the handoff needs to be. And ultimately, I think we’re seeing the emergence of, particularly for these larger user bases, the need for a more scaled customer experience for sales assist team, which can be complimentary, but much lighter touch than the traditional direct sales model.

Harry Stebbings:

I have to ask, the challenging thing for me when I think about marketing is the messaging. And when we look at your experience being the first sales rep for enterprise at Dropbox, and if we think about Loom scaling into enterprise today, the messaging for freemium and bottoms up is very different compared to the messaging required for enterprise. How do you think about that contradiction in terms and how you manage messaging when trying to hit both at the same time?

Sam Taylor:

So it’s going to different place. And it’s not to say that you don’t have brand consistency around what you’re trying to drive, but if you break it down into just the elaborative environment that someone’s in. An SMB company versus an enterprise company, the interactions at that small business, so let’s say it’s 15, 20 employees, are really going to mimic the types of interactions that you’re going to see within a team at a larger organization, particularly a cross-functional team if it’s there. But I think for us, when we focus on messaging, you then have to have different stances.

Sam Taylor:

Again, going back to this point of view on if I’m looking at this through the lens of Quip, which was also a horizontal play that we were making, because it was a productivity and collaboration solution. If you’re talking to a sales leader at a massive company, we can be positioning Quip as an amazing sales enablement, account planning, and Salesforce add-on if we’re talking post-sale. If you’re talking to a small SMB customer, Quip is a pervasive transparency and communication layer where you can literally run most of your decision making and project management process off of that. And so the value story that’s there is really going to be shifted in terms of order of magnitude based on, one, the addressable employee population, not just at the company, but frankly for the evaluating team. So I think us having clarity on how that product, whether it be Quip, Loom, whatever it is, how that value is driven at either individual team or corporate level, and then aligning our messaging and our value story there.

Harry Stebbings:

I’m totally with you in terms of the importance of that alignment. I guess my question is actually–goes back to one that I have from founders really every day, and it’s one that we skipped a phase on, really, which is like you have that core side of PMF in the early days. It’s selling, you’re getting velocity of sales. How do you think about it? And as I’ve touched on many times, being a first enterprise sales rep at Dropbox, how do you think about when’s the right time to hire the first rep? It’s the biggest question founders ask me.

Sam Taylor:

It boils down to CEO capacity. I’m making a broad assumption, but in my view, CEO has to be the best salesperson at the company for a long time. No question. I mean, it’s how you’re raising. It’s how you’re getting those first customers, the whole bit. The tricky part is how do you bottle up the mission, the message, the pitch in a way that someone else can credibly deliver. And so bear with me on the story here, but imagine me, employee twenty, and helping build out the sales motion at Quip. And my example of who’s giving the pitch and talk track right now is Bret Taylor. And so he walks into a room and talks about his stance on the future of work, where Quip fits into that spectrum and what we’re trying to do. And then you’ve got this former Dropbox sales dude who comes in and tries to deliver the same message without being the former Facebook CTO or Google Maps co-creator, it just doesn’t land.

Sam Taylor:

And so I think making that first hire is when the inbound interest or the investment that you want to make and learnings in the market are strong enough that the CEO no longer has capacity to do it. And when you’re thinking about hiring at this phase, you’re probably hiring a less traditional sales profile and more of a generalist who can talk to early users, understand where they’re finding value, package those insights and stories, and formulate that early go-to-market, that’s if you’re not handling a big inbound volume. If you do have a bunch of demand that’s coming in, you could probably skew a bit more to someone that has a bit more of a sales, a direct sales background, but I’ve always pushed the boundaries that I’ve been with, who record themselves, pitching customers or walking through their vision, their value story for the product, because there’s always a nugget, a one-liner perspective that can be repurposed and really effectively used by the sales team, but it’s not going to be a straight rip and talk track that way.

Harry Stebbings:

Can I ask, you’re saying the sales hire works out well, the challenge is always in culture. Well, creation is one, sure. But the most challenging is in culture maintenance. I’m really interested, how do you think about the balance of focusing on culture versus skills and experience when building out that of core sales team in the early days?

Sam Taylor:

Culture fit is fascinating to me. It’s a catch all term and unless very articulated and defined by a company, it just kind of becomes this anything term, but it’s also one of the biggest filters that I see when assessing talent when debriefing. And so the disconnect that I’ve seen is that folks will over-rotate on culture fit when it’s not well-defined. And so it’s more of just this gut feeling, as opposed to what are we actually looking for and what are the key things that we’re sussing out in stress testing. So when I looked at the early stage teams, the main questions that are coming to mind for me are on the sales side, we’re all here to problem solve. We’re all here to collaborate and we’re all here to execute. And the environment that I can guarantee is ambiguity.

Sam Taylor:

And so in my mind, building a strong culture and when we’re thinking about the hiring profile for these higher performing teams, you need to have a group of people that can be level-headed when it’s chaotic. You need them to be creative and solution-oriented when thinking through a path forward. And then ultimately, they need to be willing to take action, because they’re not going to have all the data they need. They’re not going to have the historicals. They’re not going to know if this sales messaging is going to work, whatever the example is, but they got to get in motion and go. And so when I’m thinking about these early teams, I’m looking for examples in their lives of showing grit and resilience. I’m looking for creative problem solving. And honestly, I’m looking for displays of high empathy.

Sam Taylor:

And ultimately, for me, I think you want to have a diverse set of experiences, perspectives, backgrounds that are coming in. And so that way there are different voices that are being additive to the culture that you’re trying to build, but empathy has to be at the core of everything else because it’s going to be a slog no matter how you cut it. And so I think the teams that are able to acknowledge how stressful and intense the environment is, being at a tiny company that way, and then learn and collaborate well together and do it in a way where even if you lose, everyone’s feeling good about the process that you just went through together. That’s the magic that we’re looking for.

Harry Stebbings:

Can I ask, what questions do you find the most revealing in terms of those leading indicators of culture success? So, a lot for me is around, “How do you think about your relationship to money? How do you think about your relationship to risk?” A lot around actually childhood and growing up, because I think that says a lot about an individual’s core character. What questions are leading for you in terms of revealing that culture fit?

Sam Taylor:

Two jump out. One, I ask someone to describe a pivotal decision they had to make in their life when the right answer was not clear. And I ask them to describe it. But more specifically, I ask them to walk me through their approach to the decision and how they made the call. I actually don’t care what the outcome was. I want to know what the process was and how they looked within to make that decision. So, that’s led to some interesting conversations along the way. And I’d say the other one that I like particularly trying to suss out working relationships and empathy. I like to do a hypothetical. Harry, you’re just interviewed for this entry-level role, you get the job. How would you imagine us working together? What would you want our relationship to look like? And what are your expectations of me?

Sam Taylor:

And I think the last piece, the expectations of me, are actually the most revealing part of that question, because you hear the language that that person uses coming back to you and the way that they’re describing honestly, their needs and then how they would hope to interact and engage. And it’s really telling just around how empathetic that that person is and how they’re probably going to be as a teammate because of the thoughtfulness with which they respond to that.

Harry Stebbings:

Trust me, Sam, I think my definition of myself would be troublemaker. So I didn’t think [inaudible 00:28:21].

Sam Taylor:

You need to be able to break some glass too. Come on in, Harry. Let’s do it.

Harry Stebbings:

Listen, I’m very touched. [inaudible 00:28:26]. I do want to ask, if you hire incredibly well and velocity of sales comes in, the sales team grows, as you saw with Dropbox, you saw it with Quip, you saw it with Salesforce. When did things start to break? And I guess what are the indicators that things are starting to break?

Sam Taylor:

Communication is the first thing to go. And so, leading indicator to me are questions. And if anything, I take inventory of the types of questions that are being asked, particularly the types of questions that are being asked by newer team members. And look, everyone gets a pass. You get to play the newbie card for a significant amount of time. Trust me, I’m using that right now in my first few weeks at Loom. However, there comes a point where you start hearing some of these questions and the ears start to perk up a little bit. You’re noticing, “That should have been covered in onboarding,” or you should have had enough at bats that you know where to go find that information, or you should have experienced that. And so you’ve got a small team of five folks, you know where to go. Even if you’re new and you’re the fifth of the five, you have four built-in mentors that you can ping on the side, ask for resources, et cetera.

Sam Taylor:

You step that up to 10 to 15 people. And while those relationships are really tight, it’s not clear who is leading the information flow and you have to be more structured. And so when I look at Loom, we’ve gone from 40 to 100 employees in 10 months. The sales and success team has gone from two to 12 in 10 months. And so even walking in the door over the last couple of weeks, I’m already starting to see areas where the team is going to need more structure. And so it’s not to say I’m going to go full Salesforce enablement field rep focus on this off the bat, but I do think that there are pared down versions of that operating cadence, the enablement resources that are there, the drum beat for the message and mission that we’re on. And I think that we’re going to need a flavor of that for us to execute quickly while we’re growing so fast.

Harry Stebbings:

I think you should text Ilya again, “Ilya, ship us some more cash fast.” I do want to move into my favorite, though, Sam, which is a quick fire round. I say a short statement, and then you give me your immediate thoughts. How does that sound?

Sam Taylor:

Let’s do it.

Harry Stebbings:

Okay. This is tough given it’s 11 days in. So far, what’s been the biggest challenge of your role with Loom?

Sam Taylor:

Focus and prioritization. There’s so much to do. It’s how do you stack rank it and go after it?

Harry Stebbings:

You’ve seen so many different companies in the world of SaaS and cultures, people. What would you most like to change about the world of SaaS today?

Sam Taylor:

It’s an easy one. In sales, bro culture has got to go, and it’s just so easy to see the trap of an early sales den and how that can spin the culture of that team out of control compared to the rest of the company. So, I’m hypersensitive to that.

Harry Stebbings:

Which sales leader do you most respect and admire? And why?

Sam Taylor:

I’ll go with Kevin Egan, who was the VP at Dropbox back in the day I rolled to and who now runs North America at Slack, an amazing operator. He’s scaled teams, iconic companies, the whole bit, but most importantly, he’s shown me the value of a relationship that transitions from boss, friend, and mentor. And he’s been a huge influence on my career post-Dropbox.

Harry Stebbings:

Not in the schedule, but you mentioned bro culture within sales teams there, I totally agree. My question is like, how do you strategically and deliberately try and remove bro culture? I find like it’s setting on aggressive targets. It just instantly leads to this kind of, I don’t know, competitiveness that comes out in bro-iness. How do you deliberately mitigate that?

Sam Taylor:

One, I think you would need to be regimented with your hiring plan and ensure that you’ve got a diverse group of sellers. And huge shout out to Pete Prowitt, the director of sales at Loom right now on the team that he has assembled early on. I think we’re an amazing place for me walking in the door there. The second piece is I think that you have to be really intentional around how is this team going to be additive to the community that you’re a part of, and meaning the broader employee population.

Sam Taylor:

And going back to what we were talking about, about feedback loops, et cetera, for me, early days in Quip, Dropbox, all the others, the key take away for me was being able to build relationships with folks with completely different backgrounds, approaches to life, you name it. And that was the focus for us early on. The gentleman who hired me, Armando Mann at Dropbox, was so intentional with us of, “You better go get your butt at the lunch table and go meet some new people. We don’t want to see you sitting in a clique.” You need to go and push yourself to extend your network and expand your horizon. And I think that it takes a lot of leadership and intention at the top to make sure that that is a part of the ethos of your team.

Harry Stebbings:

Final one, what do you think your biggest weaknesses as a sales leader? What do you do to try and mitigate it?

Sam Taylor:

I think imposter syndrome and self doubt, maybe not a traditional answer, but I’m a big believer that we need to be constantly investing in our own mental health if we want to be the leader, the husband, the father that you want to be. And so, mindfulness practice, not shying away from a few chats with a therapist along the way, have been a huge unlock for me. And trust me, I ain’t perfect. I got a long way to, but it’s been a big help for me so far.

Harry Stebbings:

Listen, Sam, as you can tell from my completely wayward questions that have deviated from the schedule so many times, I’ve so enjoyed it. Thank you so much for joining me today, and I really appreciate the time.

Sam Taylor:

It’s been my pleasure, Harry. Thank you.

Harry Stebbings:

I mean, if you couldn’t tell from incredibly wayward questions, I absolutely loved doing that one with Sam. And if you’d like to see more from us behind the scenes, you can on Instagram at hstebbings1996 with two Bs. 

Harry Stebbings:

We have some amazing shows coming for you in the next few weeks, including one with Sam’s wife, Kate, which really is a special one. So, stay tuned, and I so appreciate all your support.