Sam Taylor: How I Became VP of Sales at Loom; Lessons from Dropbox | 20VC #908

1. 0:00 – 1:44

   Sam's background

   1. HSHarry Stebbings0:00

      (beeping) Three, two, one, zero. You have now arrived at your destination. Sam, this is such a joy. You know I always love our chats, but, uh, thank you so much for putting up with my dulcet tones once again.

   2. STSam Taylor0:15

      Get out of here with that. It's always great to see you. Always great to hear from you.

   3. HSHarry Stebbings0:20

      You know, fake humility is always good to have.

   4. STSam Taylor0:22

      (laughs)

   5. HSHarry Stebbings0:22

      Um, but, uh ... (laughs) But, uh, for those that missed our first show, tell me, how did you make your way into the world of tech and, most importantly, sales? What was that entry point for you?

   6. STSam Taylor0:32

      So, definitely not a direct line from university or school straight into it. Held a number of random jobs in a number of different industries. So, studied environmental science, did environmental consulting. I was on the purchasing side of the house, that got me on the phones, uh, at a silicon wafer distribution company. Won't even get into-

   7. HSHarry Stebbings0:51

      (laughs)

   8. STSam Taylor0:51

      ... or unpack what that means. Take a whole show. Um, but ultimately, uh, got my start on both the technology and sales side at Salesforce back in 2010. Um, was fortunate enough to stumble my way into the Dropbox organization as one of their first five salespeople back in 2011. Uh, and it's really snowballed from there. And so, have been having the opportunity to learn from and work with some amazing teams between the Dropbox crew/now mafia. Uh, I think a number of folks have been on this show with you. And, uh, then also ended up on, on a couple of small growth teams at Quip, which brought me back to Salesforce, and then now, been holding things down with the Loom crew for the last, roughly, 18 months.

   9. HSHarry Stebbings1:35

      I mean, actually it's perfect timing 'cause we released a show, uh, just, just recently with Zhenya, and obviously he spent time, I presume, with you at Dropbox. And-

   10. STSam Taylor1:42

       He did. Yep.

   11. HSHarry Stebbings1:42

       ... so I'm, I'm fascinated to hear. When

2. 1:44 – 3:18

   Takeaways from Dropbox

   1. HSHarry Stebbings1:44

      we think about Salesforce and Dropbox, two such iconic companies, if we were to isolate, like, one or two takeaways for you from each, what would you say those are that've really shaped how you think today as a sales leader?

   2. STSam Taylor1:56

      So, I think Dropbox, with it being a decently early pioneer, if we want to call it, on the product-led side of the house, I think the, the early learning for me particularly is we were building the direct sales motion in tandem with the product-led side, is-

   3. HSHarry Stebbings2:12

      Yeah.

   4. STSam Taylor2:12

      ... security's not enough. You need to find more value than just security when you're thinking about a consolidation plan. I think a learning for me along the way was we were really trying to take the density of user engagement and our, our de facto was going and selling to IT or CIOs around, "How do we roll this up and how do we protect the house," so to speak. Um, which when you put it in those terms, like, you're basically positioning your service as a liability as opposed to a value add. Uh, and effective in certain ways, but, you know, in a, a environment where I think that we have to make sure that we are continuing to align with the goals of our customers, align with the impact, and particularly on the future of work side of things, like, what are we doing to enable a more effective and efficient workforce? And so I think, for me, really taking that lens, particularly when I went to Quip, which was my next opportunity, um, and really focusing on the workflow and the day-to-day engagement and impact, and then how do you roll up that positive, that additive, um, experience as a core part of your value prop. That was a key takeaway for me through

3. 3:18 – 5:03

   Can you do product-led growth and enterprise sales at the same time?

   1. STSam Taylor3:18

      Dropbox.

   2. HSHarry Stebbings3:18

      Before we move into Dropbox, I do just wanna ask, in terms of, like, the product-led growth and the enterprise in tandem-

   3. STSam Taylor3:24

      Yeah.

   4. HSHarry Stebbings3:25

      ... uh, when you advise startup founders today, given what you've seen in terms of what it takes to do both of them at the same time successfully, do you advise startups to not do them both at the same time? Or do you think startups can execute both the PLG and the enterprise heavier touch sale at the same time?

   5. STSam Taylor3:41

      I think it depends on the offering that you have. And so, as an example, if I take Loom, uh, Loom has only had a sales team for two years at this point. So, relatively nascent. Um, Loom has had customers and users, which we've been monetizing for more years than that, roughly four years. The product shift and strategy that we were making was moving from you were only, in previous, prior to a sales organization being here, able to consume and use Loom as an individual, and then it wasn't until we were moving into there being a multi-player team and company state, where you're going to be expanding and looking at the use cases, but also the potential buyer personas that you're trying to go after, expanding in a more significant way. And at that point, it makes sense to layer on. So, if I'm reversing back what I just said, it's think about who is going to be involved in being able to make a decision of, "Is this applicable to me and do I wanna pay for this service?" And if that individual can go and make that on their own, or small teams can do it without inserting a human into the process, that will always be a more efficient path to acquisition. Uh, and so I think really when you're looking at your opportunity to move further and further upmarket, um, that's where you start layering in, should we have selling capacity that is incremental and complementary to what you have going on the product side?

   6. HSHarry Stebbings5:01

      You know me, I never stick to schedule. They're boring

4. 5:03 – 8:33

   The problem of agency between buyer and consumer

   1. HSHarry Stebbings5:03

      as shit.

   2. STSam Taylor5:03

      (laughs)

   3. HSHarry Stebbings5:04

      Um, how do you approach the product marketing challenge? Because you at Loom have the product-led growth side, where, you know, end users love it in companies.

   4. STSam Taylor5:13

      Yeah.

   5. HSHarry Stebbings5:13

      But actually someone else pays for it, and so there's the problem of agency between buyer and consumer.

   6. STSam Taylor5:18

      Yeah.

   7. HSHarry Stebbings5:18

      How do you approach that today as a sales leader?

   8. STSam Taylor5:21

      I think it requires that you have an authentic curiosity to learn from your users. And how do you train and teach your sales force to take that discovery, take those learnings, and package them up both from the anecdotes and the stories that you're learning from the individual users that are finding value? And then the more broad ROI that, or impact that the business is gonna be experiencing if they're making the investment at scale. And so, I've used this term from my Quip days, and it was definitely parlaying that Dropbox learning to what are we doing at Quip, and, um...... I refer to our early sales team as workflow therapists. Like, lay on the couch, tell me all your problems, like, let's understand, like, there has to be an innate reason of why has someone individually gone and signed up for your product and inserted it into their day.

   9. HSHarry Stebbings6:11

      Mm-hmm.

   10. STSam Taylor6:11

       And how do you find the trend lines between those? How do you share those stories and make them applicable, but also consumable because you are learning the right vernacular that works for that company, that team, that department? Uh, and then how do you get your sellers really attuned at the different plays that you would have associated with that, depending on who you're talking to within the organization.

   11. HSHarry Stebbings6:32

       So if the sellers are our therapists asking those questions-

   12. STSam Taylor6:36

       (laughs)

   13. HSHarry Stebbings6:36

       ... my challenge is, what questions really discover the truth? Because a lot actually don't and customers and early users kind of say what you want to hear. They feel pressured. What questions do you like to ask to really determine and discover the truth without leading the witness, so to speak?

   14. STSam Taylor6:55

       Well, I think there has to be a- a first principles of, why were you compelled to go through and sign up? And just see what they say. Leave it super open-ended, like what it ... And then also I think the- the next piece is, you know, particularly when we are using data effectively as our sales team, which means that we're trying to talk to heavily engaged users, power users if you will, those that have the potential to be champions internally, I like to ask, "What's preventing you from sharing or forcing other folks at the company from using this?"

   15. HSHarry Stebbings7:27

       Hm.

   16. STSam Taylor7:27

       Uh, if you are. Or they may flip it on their head and be like, "No, I'm singing Loom's praises. It's all over the place." Like, "We get- we have to go and, uh, make sure everyone's using this." And then we go, "Okay, let's ask why are you needing to do that versus the product, uh, being able to expand in its own way." And so I think for us, we start to learn, frankly the cultural idiosyncrasies, uh, that are really important for how do you change behavior, and that informs then what are we doing in a proactive state as sellers to bring the right cross functional groups into the fold, the right use cases that we want to be anchoring on for a pilot group. What are the success metrics that we want to set up as a part of the sales process that we're using? And so for us it's really, how do you o- ask open-ended questions around why someone has taken personal initiative, and then how do you go through that fact-finding mission to figure out how does that play into the existing culture and workflow of the team.

   17. HSHarry Stebbings8:20

       Now you mentioned Loom having a sales team for the past two years, but actually having customers and paying customers for a lot longer.

   18. STSam Taylor8:26

       Yeah.

   19. HSHarry Stebbings8:26

       And I'm always quite perturbed by this one, which is like-

   20. STSam Taylor8:29

       (laughs) .

   21. HSHarry Stebbings8:29

       ... before we actually, actually let's just take a step back. In terms of the sales

5. 8:33 – 10:50

   The Sales Playbook

   1. HSHarry Stebbings8:33

      playbook, what does the sales playbook mean to you? Because people have many different definitions.

   2. STSam Taylor8:39

      I don't love playbook as a term because it sounds rigid. And from what I just described to you around the types of conversations that are moving the needle for us and are leading to like the true great under- understanding of our customers, I hear playbook and it's, "Let me follow the steps, let me regurgitate these things, let me ask this line of questioning," and that doesn't actually incorporate the most important part of it which is listening and then making, making moves along the way based on that. So to flip it around, I refer to it as frameworks. I apply this when I'm hiring a new leader on the team, a new rep on the team, is bring the frameworks that have worked effectively for you in the past. Playbooks are not going to be a one-to-one, "Hey, I can rip and replace and take over there." So when I think about frameworks for us and what that means for our organization, Loom, Dropbox, Quip, I've had both the blessing and the challenge of horizontal tools that can be used by almost anybody at an organization, which is an amazing opportunity from a TAM perspective and a challenging opportunity from a where do we start and why? Uh, and I think for us when I look at frameworks, it's whether it be vertical specific, whether it be persona pacific- specific, how do we start to layer in applicable stories? I think storytelling is such a key part to sales.

   3. HSHarry Stebbings10:01

      Mm.

   4. STSam Taylor10:01

      Uh, and so how do we have relevant stories that our customer facing teams, regardless if they're- if they're quota carrying, like are they, are they adept at being able to tell the meaningful stories from our user base, our customer base, et cetera? Um, and then also how do we then look at the different types of plays if you want to put it that way, or frameworks for are you going to have more of a bottoms-up adoption driven play? Are we going to have a more tops-down initiative because we're actually aligned with power, uh, and we're attached to a more strategic undergoing at the company and Loom is going to be a vector or in service of that strategy? Um, and those are the sorts of things that we need to capture in terms of what are the elements of health for those pursuits, uh, and then what are the right frameworks to be applying and the right stories to be inserting based on that?

   5. HSHarry Stebbings10:49

      So me and Jenia had

6. 10:50 – 12:55

   Who should create the first Sales Playbook?

   1. HSHarry Stebbings10:50

      different views here. I believe that founders should be the ones to create the first frameworks, to create the first stories, and to really be the creators of them.

   2. STSam Taylor11:00

      Yeah.

   3. HSHarry Stebbings11:00

      He said that actually they shouldn't be and that it should be a sales leader, actually, that is brought in. Should it be the founder who creates the first framework? So, is it okay for it to be brought in by a sales leader?

   4. STSam Taylor11:13

      Well, I'd kind of call bullshit on the founder can't create it. Like if you raised money, you started a company, and you have the capital to hire anybody, you're in sales, so you've already created that sales pitch. The question is, is it actually credible for folks that you are hiring that are not you, Mr. or Mrs. Founder? Um, can they deliver that message credibly? And so I think the iteration then becomes what are the nuggets and what are the key valuate- value areas that have been uncovered during early customer wins or even losses? Uh, and then what are the ways that we want to package up those things for an early customer facing person to be able to run with? I think the ability for folks early days, so if you're a founder that's just hiring the- the first set of folks on your team, allowing them access to...... you pitching, in some way, shape, or form. That can be you capturing it or you having some sort of log of the, the conversations that you're doing, or actually taking the time to allow them to write shotgun on, um, their onboarding experience because there's so much that can be taken away from what is going to probably be perceived as table stakes things that you've been saying for years that are actually gonna be a huge unlock and highly applicable and inserted into the frameworks that that customer-facing person is gonna be able to reuse. And so, don't discount, uh, the special sauce that you've practiced.

   5. HSHarry Stebbings12:42

      What do you recommend, then? I'm the founder, I've got us to kind of 30K MRR.

   6. STSam Taylor12:46

      Yeah.

   7. HSHarry Stebbings12:46

      Should I create, like, Word docs with, like, the script that I use, the core value props that I say to the different people within orgs? Should I record my calls on

7. 12:55 – 14:58

   Should you record calls?

   1. HSHarry Stebbings12:55

      certain SalesLoft or whatever we're using? W- uh, how can I document it for you coming in, so you can go, "Oh, I've got a treasure trove of, you know, potentials?"

   2. STSam Taylor13:04

      I think the... I don't think there needs to be overly detailed. Like the lift here, like there, there's like a 80/20 value a- approach here, absolutely, of who are the folks that you've engaged m- where there's just been an unlock. They get it. Like, I think in most companies you find that there's going to be certain customers that just... th- they got it from day one, they're off to the races, they're ripping. Analyze those. Don't take them for granted. Why? Like, what were the dynamics of the role the person was in, the phase of company that they're in? What are th- what are the key identifiers that might be that map for where someone might want to spend their time proactively or pattern match what health is going to look like? And then how do you unpack, ultimately, your product experience, your onboarding experience, all the things that you would want? So like, how do you have the highest likelihood that someone is going to end up in that state which you consider to be really healthy? So, those usually are very- are, are bullet points. I think the recording of calls is actually where the most value can be had.

   3. HSHarry Stebbings14:06

      Mm-hmm.

   4. STSam Taylor14:07

      Um, and only because it's so rare, in my experience, that the founders are actually recording that and then making it available to the rest of the employee base, because it's really personal (laughs) -

   5. HSHarry Stebbings14:19

      (laughs)

   6. STSam Taylor14:19

      ... and it feels intrusive at times, and it feels like, oh my gosh, like did I even do it right? Who am I to say that I'm the expert on XYZ thing? But again, it's the- that objection handle, that positioning, that, uh, extra question that that founder asked along the way which you built the muscle memory for by getting your company to the place that it's in because you have been in sales the entire time. Uh, you just may not actually unlock and think that that is something that can be used by someone other than you.

   7. HSHarry Stebbings14:47

      I'd be so good at this. I've, I've got quite used to recording myself. (laughs)

   8. STSam Taylor14:51

      See? Nailed it. (laughs)

   9. HSHarry Stebbings14:52

      There we go. I, I should be a startup founder.

   10. STSam Taylor14:55

       (laughs)

   11. HSHarry Stebbings14:55

       Uh, no, it was a terrible idea.

   12. STSam Taylor14:57

       (laughs)

   13. HSHarry Stebbings14:57

       Uh, no, I, I do have to

8. 14:58 – 20:55

   What type of person do you hire as your first Head of Sales?

   1. HSHarry Stebbings14:58

      ask. In terms of, like, that first hire that we bring in, though, and we said kind of should the founder be the one to create the framework.

   2. STSam Taylor15:03

      Yeah.

   3. HSHarry Stebbings15:03

      Whatever, uh, in terms of that. Like, in terms of the person that we bring in, do you think that we should bring in younger reps who are more plastic, kind of jack of all trades, or should we be bringing more seasoned heads of sales to then build a team beneath them?

   4. STSam Taylor15:20

      In my view, the answer is C, neither, potentially.

   5. HSHarry Stebbings15:25

      (laughs)

   6. STSam Taylor15:26

      Uh, and the, the reason for that is it depends on what you want. Like, uh, like are you at a place where let's say that you're a pretty niche product and you have a pretty solid value prop and it's very clear who the buyer persona is and it's like, we need folks to be triaging an inbound queue and possibly outbounding into this narrow thing that we are building in service of. You could make the argument, let's get some junior resources in and let's start seeing if you can scale to the next level if you're just having more customer conversations. More times than not, in my experience, and I, I draw on both Loom as well as Quip in this case, there's a blend early days of, uh, are your first customer interactions support, more customer success oriented 'cause you're helping them figure out the value that's there? Is it actually sales? Like do they know what they're getting with your solution? And so, with these early hires, and I still repeat this, and my team if they listen at some point are gonna go, "Oh man, there he is saying it again," but I really view that our team is on the hook for two things, RR and insights. And the insights are almost as important, if not more important, the earlier you on- e- earlier you are on your go-to-market journey, because that helps inform where do you want to resource and how do you want to go to market more broadly? How do you build conviction in the right ways? And so, I've personally seen that having folks that are more excited around just customer learnings, feedback, interactions, and first principles like inquisitive thinking, and then being able to take that in a structured way and translate it to the CEO, but also to your product lead. If there's a marketing person that's there, how do you get them on the same page? And there's so much more value, in my opinion, on how do you get the cross-functional company bought into the voice of the customer? And that may not be a quota-carrying rep that can deliver that, if that's the most important thing to you early on.

   7. HSHarry Stebbings17:30

      Do you have a conflict running a PLG and an enterprise motion in one? 'Cause you could have, you know, certain people in the organization saying, "Hey, we need the product team focused on referrals within app, within whatever, natural kind of growth tactics, much more product-led initiatives." And then you could have the enterprise rep saying, "Hey, we need RBAC, we need SSO, we need, uh, you know, enterprise requirements."

   8. STSam Taylor17:57

      Yeah.

   9. HSHarry Stebbings17:57

      Uh, do you have that conflict given the ge- like dual-running of both?

   10. STSam Taylor18:03

       I don't see... Conflict sounds like it's like this, and I think that the, the reality is...And I'm probably well skewed based on the organizations that I've selected into along the way. But, uh, the product leads everything. And, the more compelling thing in my view, if, if you're going up into the enterprise, having depth of engagement, having there be masses of folks that are gravitating towards your product, regardless of even talking to someone, and that being the statement of users speaking with their actions, that's gonna fast track you through so many more enterprise conversations because of the conviction on value to the organization in the early days, versus the unlock of RBAC, or whatever it may be. You have to figure out a path then on, okay, if that is the, the balancing act and you want to be doing both, at what threshold as a product marketing and sales organization are you all aligned on that it becomes statistically significant, if we want to put it that. It's probably not even that regimented. At what threshold does it tip us into this is something that we need to be resourcing and roadmapping in a more proactive way than what we've been doing in terms of core product innovation to date? And I think that that is always going to be a trade-off that has to be made if you're in a resource-constrained environment. But ultimately it's also about like what is your ability to go and capture a market? And I think for us as we're, you know, really trying to carve out a category here at Loom in terms of the way that people are interacting with video at work, um, we feel that there's a huge opportunity for us to grab market share by going into the enterprise and influencing larger organizations and the way that they're working, not only because we're trying to force our way in, but we're in a fortunate and privileged position that they're coming to us looking for that. And so, I think as we look at and as we can stack up, here are the common themes and threads, that voice of the customer that our sales organization and insights that we're delivering back, how does that build conviction and therefore the roadmap that we wanna build towards of what unlocks the right type of customer and how do we have agreement then as an organization on what is the ICP that we're willing to go after? And the reason the ICP thing, in my opinion, is important is you're gonna get a lot of inbound interest, particularly from very large enterprises, many of whom are in regulated industries that you are not even remotely close to equipping and servicing in a realistic way. And so I think, uh, having very defined filters of what you will or won't entertain as a collective company, um, as a guiding and north star for you is, is important in my opinion.

   11. HSHarry Stebbings20:53

       I have so many questions.

9. 20:55 – 24:55

   Running Inbound and Outbound Sales at the Same Time

   1. HSHarry Stebbings20:55

      I think my first question (laughs) is like you mentioned kind of, you know, being lucky to have many inbound, and like, of course, um, that's a fantastic privilege and great.

   2. STSam Taylor21:04

      Yeah.

   3. HSHarry Stebbings21:04

      But you also can't rely on it because at some point in the future, you don't know when, but at some point, it tails off...

   4. STSam Taylor21:10

      Yeah.

   5. HSHarry Stebbings21:10

      ... and you have to have outbound. How do you think about the dual running of inbound and outbound, and what are some big challenges you find companies face when layering on outbound when they've relied on inbound for a long time?

   6. STSam Taylor21:26

      It's a completely different motion for your organization. Um, and that may sound very obvious, but let's unpack what that means. Uh, you have assumed intent on the inbound side. You have assumed value, especially if you've got users that are engaging and, and utilizing your product at work already. Versus outbound, like no clue. Maybe, maybe they're using us, maybe there's some indications of where you wanna be outbounding, but typically you are moving from team level, end user, and department level engagement being the driver of the why, why you, why now approach. And as you're moving into outbound, you as an organization need to be much more opinionated on here's why you should have an initiative that's aligned to what we're doing. Uh, here's the impact that you should be experiencing and we would be delivering for you, and then how do we make sure that ultimately we are, we're delivering on that a- as a team. And so I think from an outbound motion perspective, you know, we've already started to do this at Loom of like we're in the early innings of experimenting and building that motion, not because we need it, because we know that someday we're gonna need it, and it's a muscle that you have to build over time. Um, and in my experience, that's a, that's a 12 to 18 month runway of actually getting the learnings, getting the motion, and getting, uh, the fruit of that labor so to speak. And so going back to your original question of should you do both or are they a- at odds, they're not at odds, but you have to treat them as completely different go-to-market motions as you're resourcing it from a PMM positioning perspective, from a rep accountability and activity perspective, and then ultimately, um, the way that you are structuring the evaluations that come from it.

   7. HSHarry Stebbings23:10

      Can I ask, what's the biggest challenge of building an outbound team? (laughs)

   8. STSam Taylor23:17

      I'd say the early days of like knowing it is a muscle that you're building. I, I put it as like you decide to work out for the first time and it feels like you're, you're going to the gym and it sucks. You're not... You're sore, but you're not seeing any gains and you're not seeing any impact, and you have this moment of like, "What the F am I doing? This sucks and I'm not seeing any benefit. Why do it?" Uh, and so I think that maintaining the perspective on how do we push our teams, how do we push the collective company to continue making the investment, um, and how do you start to set more incremental, um, milestones for what success looks like. And I think if you're focused just on output metrics around what have we closed, these deal cycles are gonna be longer. The, uh, engagement that you expect earlier on is going to take longer to build. The perspective on what is actually resonating versus not, um, is also something that you have to be taking inventory on. And so I think, uh, cherishing repeatability and cherishing the, uh...... the pipeline as you bring it in, to put it in sales terms of like, what are the early indications of success? And that doesn't necessarily mean that revenue's even hit the books yet. But how do you actually embrace the learning process? Uh, and I think that if you can begin to figure out what gets people to say yes to talking to you when they've never heard of your company before, and how do you make that repeatable? That is a huge next step to, great, then how do we start to figure out the right ways to engage structure and run these deal cycles? Just because they're going to be very different than the conversion funnel that you have already established on the inbound side.

   9. HSHarry Stebbings24:52

      We're gonna get on to those kind of crucial lessons and insights

10. 24:55 – 31:18

    Structuring the Hiring Process for Sales

    1. HSHarry Stebbings24:55

       on what causes conversion. I do wanna just touch on the hiring process itself, 'cause you're an angel in my hypothetical company. Congratulations.

    2. STSam Taylor25:02

       Yup. (laughs)

    3. HSHarry Stebbings25:02

       Um, thrilled to have you, Sam.

    4. STSam Taylor25:03

       Thrilled to be here. (laughs)

    5. HSHarry Stebbings25:05

       (laughs) Amazing. Um, uh-

    6. STSam Taylor25:06

       (laughs)

    7. HSHarry Stebbings25:06

       ... but I have no idea how to hire a sales rep or sales leader. In terms of structuring the hiring process itself, I know it sounds stupid and kind of, um, naive of me, but literally, how do I do it on an interview-by-interview basis? Who do I bring in at what point? What data do I give them? Do I do case studies? I don't know. Help. (laughs)

    8. STSam Taylor25:29

       Yeah. So, and to be clear, are we talking about first hires that you're making?

    9. HSHarry Stebbings25:34

       First hires that I'm making, 30 to 50K MRR. It's working, but I need to bring in the first salespeople. (laughs)

    10. STSam Taylor25:41

        Yep. I think as a founder, I would be taking inventory of, what is the reason why you need to hire sales capacity today? Is it, I don't have strong inclination around deal structure and approach, and we're having a bunch of inbound interest, but we're not actually not sure the right way and the right cadence to be setting up our sales process? So do we want people that have a lot of structure? Uh, I think, and this is going to candidate profile. We'll get into the- the actual, uh, way to tease these things out. On the flip side, it could be, I actually just have a lot of conviction that if we, if we increase the number of conversations that we're having, um, we already have strong conversion, like we have, like, a strong ICP we're going after. Um, we need people that can kind of triage and just handle the inbound that's coming to them. That's gonna be a different set of skills. So I think looking at the- the founder's side of, what are you actually trying to remove from your plate with these hires? And what is the complementary, hopefully, approach of, where are you getting energy in customer conversations or not? And how do you make sure that you're hiring the right profile of folks that is going to scale and compound the effect of their being there, uh, versus just being potentially carbon copies of- of what you've already been doing? So when we get into the actual interview phase, like based on those criteria, that's where I start to structure in different ways of, what are the early filters that you wanna be setting up? And so for some, it may be much more process-oriented. In my opinion, personally, spiking for product enthusiasm, curiosity, and structured learnings, uh, 'cause the learnings and the insights are gonna be so important. And so asking questions and talking about what may have been not related to sales, but, "Tell me about subject matters that you've been interested in. Tell me about, uh, group projects that you've been working on and the- the way in which you've rallied other folks around it. Tell me about times where, uh, you've had to convince people to do something that maybe they didn't think they wanted to do at first." And so we... I ask very open-ended questions there. I think when we're getting into the actual, like, what is the way that we want to measure this talent? I'm a big believer that whoever the hiring manager is, whether that is the CEO, whether that's gonna be another member, like there should be, uh, a very much like 50-50 split in terms of time of getting to know one another and feeling out the two-way street. That is like, do you seem to be a fit and have the right filters that we are looking for in terms of your experience? But also on the flip side, like there's a decent amount of selling in the early days of, why should this candidate take a risk on you and your opportunity? Like what- what- what are you on, and- and what is your mission, and what are your values? Um, as you get through that and you find at least your early conviction of like, "Oh, I think we may have a- a mutual benefit here," um, that's where we start moving into a more cross-functional group. And I think, I'm- I'm a big believer early days that what you absolutely don't want is for your customer-facing teams, your sales team, whatever it is that you're hiring to be on an island in any way, shape, or form. And I think that that's something that, um, can be challenging, particularly with companies that are leading with an early team that is much more product engineering and design-focused. This- this new function being inserted into, uh, the company can be something jarring at times if not handled properly. And so that's why-

    11. HSHarry Stebbings29:02

        So how do we pre- How do we prevent that? Do we bring in the CPO and designers and devs into the hiring process as like a hiring panel? How do we integrate them to make it a more kind of holistic process?

    12. STSam Taylor29:15

        I personally, when I'm putting together panels, look for who culturally has some of the most deep cross-functional relationships and the highest level of credibility across those folks. And how do I make sure that those people are- are inserted into our hiring panel? And I think the- the biggest thing that I'm looking for there is not necessarily this person is going to be filtering and looking at the sales competencies for this potential candidate. Um, does this person pass the test on being able to build credibility with folks across the company? And is this person, um, going to be able to build those relationships? And I- I go back to my early days. Armando Mann is who hired me at, uh, at Dropbox back in the day. Um, he's been on an amazing journey since then at a few companies, most recently Hopin. And, you know, he sat us down early days at the- the lunch table literally, 'cause we were all in the office. He's like, "The absolute best thing that you can do for your career is to sit at lunch every day with anyone other than the sales team. Go and make relationships with the product organization, the engineers, the folks that are here that are building, because guess what?... they're all the ones that are about to go start a company in the next five to ten years. And you being able to have those relationships, but also the context of what it takes to build in the early days, is actually the most important thing that you can learn and build a muscle on. And I think that if you take that ethos of... Really a filter that I'm looking for for early customer-facing teams is, can you sit at that virtual or physical lunch table and be the only person potentially that's actually in a customer-facing role? And are you going to have the, the EQ, the product enthusiasm, and the mission alignment that everyone else does that's gonna create those bonds and have a healthy culture at that point?

    13. HSHarry Stebbings31:12

        I love that in terms of sitting at a lunch table, going from like super nice and personal and human,

11. 31:18 – 35:37

    Should you use case studies when hiring?

    1. HSHarry Stebbings31:18

       to another thing that I was intrigued that Genya said. He said, "I don't like case studies. I don't like them. Don't find them useful." How do I actually test your ability to have pipeline coverage, to construct pipe, to really be rational about pipe conversions? Uh, how... Do you like case studies, and should I use them as a founder in this process?

    2. STSam Taylor31:40

       I don't like case studies because I think they're overly structured. What I do like is the opportunity for someone to show you how they work or how they think. And depending on the phase or role that you're hiring for, if you've got someone that is going to be working heavily cross-functionally, I would include a working session with that person. And in this situation, you would give them a prompt. You could argue as a case study, but ideally it's something that's much more of a, "Here's a problem that we're trying to tackle. We are not going to give you a ton of information, but we want you to guide the discussion between us of, like, how do we start to problem-solve and work through this together?" That would be one-

    3. HSHarry Stebbings32:19

       (sighs) What, what, what would be a type of problem, just so I have an idea?

    4. STSam Taylor32:23

       Sure. Um, you could have it be customer objections, uh, where we're consistently hearing X. Someone's not comfor-... We'll use Loom as an example. Uh, someone is consistently telling us, or our customers are consistently telling us, um, they're not comfortable reporting, whatever. Making stuff up. Uh, and we want to figure out the right way to think about our go-to-market, but also our product and our marketing initiatives to go and tackle this common objection. Like, how would you think about giving us that feedback? And so it gives them an opportunity of like, to set the table and deliver the feedback. But then also, how do you structure a discussion around the go-forward path? Now, we're doing it for something-

    5. HSHarry Stebbings33:07

       Do you think-

    6. STSam Taylor33:07

       ... that's-

    7. HSHarry Stebbings33:07

       Do you-

    8. STSam Taylor33:07

       ... would be applicable for someone that's really, really generalist as opposed to sales-specific. I think that if you're looking-

    9. HSHarry Stebbings33:14

       Do you-

    10. STSam Taylor33:14

        Go ahead.

    11. HSHarry Stebbings33:14

        Do you give them time to do the work? Do you g- say, "Hey, go away."

    12. STSam Taylor33:18

        Oh, totally. Yes.

    13. HSHarry Stebbings33:18

        Yeah. Okay. So it's not in real time.

    14. STSam Taylor33:20

        Not in real time. And I think that that is something where if you're gonna give someone the expectation that they are doing something on the fly, in my view, you owe it to them to have that be in a subject matter area that they have deep expertise and context, their existing role, existing company, whatever it may be. Many founders and many companies I see, they want to use the learning opportunity for things that they are navigating as an organization. So it's value-add in terms of the conversation regardless of outcome. You can learn something in every conversation. Uh, but many times trying to ask somebody to solve your company's problems on the fly in real time is broadly not setting anybody up for success. We do something called take-homes, and it sits in between the initial hiring manager screen and the on-site panel. And we give folks, if you're in a sales leadership role, for example, that we're hiring for, it would probably be a couple of prompts between, "How do you think about building culture, building rapport, and investing in your team? Let's talk about your, your leadership philosophies." And of course, we're, we're dogfooding hard. And so people are submitting Looms for that to us. Um, but then also we get into more tactical sales management principles approach, um, and how they would think about structuring the accountability for their team. Uh, and the flip side of it, of, of how do you start to move us from early days squishy in terms of process to how do you help us transition and, and work towards, not necessarily a full machine, but definitely more of a funnel view of the business? And, uh, by giving those prompts ahead of time and allowing people to do it, but also time boxing, like we say, "You got five minutes tops to, to deliver this information. We don't want this to be, you know, a dissertation that you're going forth and, and bringing back to us." Um, we found that that pairing gives us insight into, what does this person look like in terms of polish when they've got, uh, time on their side to, to prepare? Uh, but also, frankly, with video as a medium, we just start to see a lot around the communication style, skills, et cetera. And the entire panel, assuming that they pass, is able to consume those Looms prior to them joining, uh, for the live sessions throughout that interview day. And so, you're short-circuiting some of the relationship-building and

12. 35:37 – 35:41

    The biggest mistake founders make when hiring

    1. STSam Taylor35:37

       context-building, uh, which I think is beneficial for our panel as well.

    2. HSHarry Stebbings35:40

       What are the

13. 35:41 – 37:25

    Advice on Sales Compensation

    1. HSHarry Stebbings35:41

       biggest mistakes you see founders make in the hiring process?

    2. STSam Taylor35:45

       One, not having clarity on what they want-

    3. HSHarry Stebbings35:48

       Mm-hmm.

    4. STSam Taylor35:48

       ... early on. Like, what is, what is the actual goal of this role? And in having conversations early on, I'll see it span everything from, "We need someone to help us figure out our entire go-to-market approach, because this is gonna be the first, air quotes, 'go-to-market hire.'" Uh, or on the flip side, it's, "We want this person to, to come in and build an outbound motion, because we got the product thing already taken care of." And by having either too wide of an aperture or too narrow, you're, y- you can't have it all, right? And so, I think that you just, uh, need to have really clear conviction around, uh, what it is that you're hiring for, why, and then how do you structure both the questions that you are gonna be asking individually, the filters with which you're looking at these, um, these candidates through, and then ultimately the focus areas if you have a cross-functional panel of what are the key things that you want to be dividing and conquering on in each conversation. So it doesn't just end up being a repetition of the conversation before.

    5. HSHarry Stebbings36:47

       Do you have any advice to me on sales comp? It's a bit of a kind of, um, opaque topic, I find. For a first-time founder, any advice on big mistakes made, often wins that can happen? What would you say?

    6. STSam Taylor37:01

       I think variable compensation is an excellent lever at the right time.

    7. HSHarry Stebbings37:05

       Mm-hmm.

    8. STSam Taylor37:05

       And I don't think the right time is going to be your first couple of hires because you got no data. And if we're looking statistically at someone having, you know, let's call it between 50 and 30% of their compensation tied to these outcomes and you have no idea what's possible or repeatable from an outcome perspective,

14. 37:25 – 40:55

    How to onboard Sales Reps at a startup

    1. STSam Taylor37:25

       that fee- feels misaligned. I think a way that you can continue to bring folks in that have upside of some kind is, how do you structure different incentives that aren't just revenue-focused earlier on in the process as you're conn- continuing to build that, um, that conviction and what the targets should be? And so I'd say, you know, for me at Quip early days, uh, we had compensation models that were very loose in terms of, um, you were mostly base salary, but you would share an upside as you would go and perform at certain levels, but your base was enough that you should be able to live in San Francisco and be a productive member of this company. Um, and then even early days here at Loom, it was a combination of both revenue but also, um, the input metrics that we would expect folks to do just because we were trying to build those customer learnings early on. And so I'd say don't lean too heavily into standard variable compensation, uh, just for the sake of it. I'd say give yourself the time to actually build an informed data opinion on why those targets should be what they should be, uh, and why you would expect someone to ramp at the rate that they're ramping.

    2. HSHarry Stebbings38:32

       So now that we've hired this first person, we've gone through that process, they've accepted our offer, fantastic.

    3. STSam Taylor38:37

       Yeah.

    4. HSHarry Stebbings38:38

       It's the first sales hires and I'm busy found- I'm fundraising as well. Uh, uh, w- I rock up for first day. How do I do onboarding? What do- what does that look like?

    5. STSam Taylor38:49

       So, in my opinion, there's a, there's a sliding scale of how do you, how do you narrow eventually towards someone's core role and the core competencies of those roles. Most important thing is you are hiring someone, in its most simple form in my opinion, to be an ambassador and extension of your product and your brand. And for them to do that effectively, they have to understand, what is the community that I've just joined? What do we stand for? And, you know, if we're using Loom, like what does it mean to be a Loommate, uh, which is what we refer to ourselves as. And I think that there's a huge part of how do you bring people in to understand the structure of the company, the mission, the values? Um, how do you lead with a bunch of cross-functional conversations so they can get to know Loommates, in our case, from across all sorts of different functions? I think a fast follow to that is product evangelism requires product knowledge. And so how do we go deep on enabling and teaching folks to be power users and have a deep understanding of not only what are we delivering from a product perspective, but almost more importantly for going back to that workflow therapist, uh, analogy earlier on, um, what's your perspective on the workplace today? What- what do we, what are we seeing in terms of trends? What are we seeing in terms of experiences, um, that we are trying to lead people towards? And I think that, uh, in our case, in- in the industry that we're in, there's actually a pretty healthy blending right now of people understand as it relates to Loom of, "Sure, I can- I can click on the icon on the desktop and hit record and get a three, two, one countdown and I'm going." When should I do it? Why should I do it? And how does that actually layer into modern work? And how does that actually get us to a place where we're talking more about employee empowerment, flexibility, and the cultural as well as efficiency benefits that you're going to get by embodying that as an organization? And so for us, we have to equip our sellers with, how do we talk about the industry? How do we talk about why Loom fits into the trends that are happening today? Uh, and then ultimately, how

15. 40:55 – 42:37

    When do I need to bring moola in the coola'?

    1. STSam Taylor40:55

       does our pro- product ultimately get into being in service of those things over time? And then we start-

    2. HSHarry Stebbings41:01

       So after- af- af- after this indoctrination do we do a-

    3. STSam Taylor41:03

       (laughs)

    4. HSHarry Stebbings41:04

       ... do we, do we do a test? Do we say, "All right, Sam, you've, you've had two weeks on, on the coaching academy."

    5. STSam Taylor41:09

       Yeah.

    6. HSHarry Stebbings41:10

       "Sell me this pen."

    7. STSam Taylor41:12

       Absolutely. Uh, I think it's- there's a- there's something ceremonial about getting through the fire, so to speak, of, um, validating your readiness to, to talk to customers in front of your peers and in front of a cross-functional group. I also just think there is a huge benefit early and upfront of building a culture of coaching and being open to feedback and, and cherishing that feedback. And so, uh, we have all of our folks within the first... They usually have their first week, which is gonna be much more of the company and cross-functional. As we get into their second, third, and fourth weeks, um, very much gonna be more tactical around what are we doing in terms of the- the motion, uh, with the- the sales team today. Um, and we- we accelerate that. So usually by the end of the second week that someone's here, they are doing a full demonstration as well as running a, a mock, uh, discovery. And we solicit feedback from not only the folks that they are aligned to in terms of their onboarding buddies, um, but also a broader swath of the team so they can get feedback as well.

    8. HSHarry Stebbings42:16

       When do I need to bring moolah in the cooler?

    9. STSam Taylor42:19

       (laughs)

    10. HSHarry Stebbings42:19

        When do I need to be delivering some value? You know, 'cause it's great, we've had this first month, but actually sometimes the rubber hits the road. How long do we give people before they start delivering?

    11. STSam Taylor42:29

        I think broadly I look at this from a segment perspective because you're gonna have different, different deal cycles and different

16. 42:37 – 43:40

    Early signs you've hired a dud

    1. STSam Taylor42:37

       expectations. Um, for our commercial business, for example, like our, our SMB reps are in the roughly 45-day window for average deal time, which means that, you know, if you're- you're getting your first customer conversations, there's going to be a bit of a- an inefficiency early and upfront as you're building, uh, those early...... that early pipeline, so to speak, um, you're roughly in a 2X deal cycle timeframe of like, within the first 90 days you should start to see deal flow. Realistically, within, um, the first 60 days you should have some later stage pipeline that's sitting at, you know, pricing negotiation or aligning to the right, uh, the right buyer personas internally. I think for the enterprise, you're gonna have a lot more extended time that's there, which means that the, the expectation is going to be much more on the leading indicators, like how, how much progress were you making in terms of multi-threading into your accounts? Uh, what early commitments are we getting in terms of pile and engagement, uh, structuring criteria there? What is our path to you starting to put yourself in

17. 43:40 – 45:42

    Cross-functional engagement in the world of Remote Work

    1. STSam Taylor43:40

       a place from a coverage ratio perspective that aligns to the ramp schedule that we've given you? Uh, just because those deals statistically are going to be more in the six-month to nine-month range, and, um, you're probably not gonna be having significant ARR that's retired until that point.

    2. HSHarry Stebbings43:56

       What are some early signs that actually we hired a dud, sadly, and they're not very good? What are some of those early signs?

    3. STSam Taylor44:05

       I'd say you can, you can see it from a cross-functional engagement perspective. Those that are coming in that are great hires are asking really high-quality questions, and they're not just asking them of their team. They're going on a fricking f- fact-finding mission cross-functionally, and they're building relationships to go and do it. And so I'd say those that have come in early and have had sustained success are just absolutely passionate about learning as much as they can around not only the what, but the why and the why behind the way that we're architecting and building our product or the way that we're positioning go-to marketing. And so I'd say very, very early on you can see the enthusiasm as well as the quality of the questions that are being asked. Uh, if you're seeing that those that are, that are treating their opportunities to be learning in a much more passive or just not pursuing them at all, those are major red flags early on.

    4. HSHarry Stebbings45:02

       Is that cross-functional engagement much, much harder in a remote world, where if I'm a new sales rep, I'm, you know, a little bit younger than you, I'm a little bit intimidated-

    5. STSam Taylor45:11

       Yeah.

    6. HSHarry Stebbings45:11

       ... to go and ping some people in product just on email when I haven't met them, but actually saying hi in the lift and then going and hanging out with them at lunch. It's much easier when we're in that office.

    7. STSam Taylor45:22

       Yep.

    8. HSHarry Stebbings45:22

       And, and so I guess my question is, what can leaders do to create that engagement in a world where it has to be manufactured more?

    9. STSam Taylor45:30

       We literally give people a list of cross-functional folks that should be on their... we refer to it as a listening tour. Uh, and we also give prompts of... not for each person by,

18. 45:42 – 50:07

    How to set up a Deal Review

    1. STSam Taylor45:42

       by function, but just what are the types of themes or types of questions that you should feel emboldened to ask that person? Uh, and an example of that would be like, "Hey, if you're talking to someone on the product side, um, tell me about the way that you're approaching milestones and road mapping. How do we have inputs into those? What are the ways that you're being influenced by the customer, and how can I think about packaging up my learnings in, uh, the most effective way so it can be consumed well by you?" Those sorts of things. Um, and we make sure that that spans OG, early engineering talent folks that are going to be within kind of the broader go-to market between our PMM team, our operations team, um, different parts of the sales organization. Uh, I think a center of absolute unbelievable treasure trove of knowledge sits within a support organization, if you have one, just because they're hearing, uh, both the blemishes as well as the praises of the product on a daily basis, and typically at a much higher volume than any other customer-facing team. Uh, and so how do we go and point these folks to the right well-stocked knowledge?

    2. HSHarry Stebbings46:50

       Well, actually, I, I, I loved OJ at Asana, who I'm not sure if you worked with at your time at Dropbox. Um-

    3. STSam Taylor46:54

       Absolutely. Yep.

    4. HSHarry Stebbings46:55

       Yeah. S- so he puts all new reps in customer support as one of their first weeks. It's like-

    5. STSam Taylor47:00

       Yeah.

    6. HSHarry Stebbings47:00

       ... you are there for the whole week. I love that.

    7. STSam Taylor47:03

       Yeah.

    8. HSHarry Stebbings47:03

       Um, c- can I ask you, one thing that I find, um... final one before we do a quick-fire, but I find deal reviews fascinating. Um, when you think about deal reviews, how often do you do them? Who sets the agenda? Who comes to the deal review? Can you just walk me through it? 'Cause I've never done them before, but we're scaling and we need to now.

    9. STSam Taylor47:22

       Totally. Um, so I'd say intuitive for us as we've scaled the team, just because we've moved from being, there being four sellers a year and a half ago, we can all just sit in the proverbial Zoom room and break it down together, to, um, broader cross-functional teams. And so we put the, um... the cadence is being driven by the segment leaders, so whether it be our commercial sales leader, our enterprise sales leader. I think the person that we want driving the conversation is absolutely the deal team that was involved. I think the cadence with which we're doing it at this point is biweekly.

    10. HSHarry Stebbings48:00

        Mm-hmm.

    11. STSam Taylor48:00

        Um, and the thing that we are really anchoring on for us is, it's both deal review but also post-mortem. Uh, and I think that we have to... Celebrate is probably too far of a term, but it's like, we're all gonna be making mistakes and we're knocking about a thousand. You look at average close rates and healthy ones being in the 30-something percent range. You're not, you're not closing them all. And so how do you reverse engineer why, and what are the potential things that we could have done differently, or what are the things that ultimately did or did not end up resonating in a way that we want to learn from as a group? I think the amazing part that I've seen with our team at Loom is that who is sitting on that invite, it is not segment-specific. And so we invite sellers, CSMs, whoever it may be are free to attend. Uh, we also use it as an opportunity to invite members of the product organization as well, uh, particularly those that are building in service of our move up market, uh, just so they can get more nuance and context and have the ability to ask questions as well.

    12. HSHarry Stebbings49:04

        So there's a consistent reason why we're not converting customers. It's because it wasn't urgent for the customer, and they pushed it back a quarter.

    13. STSam Taylor49:12

        (laughs)

    14. HSHarry Stebbings49:12

        We both know that one. Um-

    15. STSam Taylor49:15

        Always.

    16. HSHarry Stebbings49:15

        W- what's your answer as my advisor? 'Cause this has happened a couple of times now, Sam. What do I do?

    17. STSam Taylor49:23

        Ultimately, you are having to go through the process when you're doing that postmortem on, "Why wasn't it a priority?" And you could argue that that is ultimately what sales is, is how do you take something that is not a priority and find a path to making it one. And when I see-

    18. HSHarry Stebbings49:42

        Can, can you, can you do that though in real time? Sorry, I don't mean to interrupt you. But when you have a customer who's like, "Hey, it's not a priority," they're not off lead. Like, they might convert next quarter.

    19. STSam Taylor49:51

        Yeah.

    20. HSHarry Stebbings49:51

        And you don't wanna seem too pushy, too transactional-

    21. STSam Taylor49:54

        Yeah.

    22. HSHarry Stebbings49:54

        ... and lose that humanistic side of the relationship.

    23. STSam Taylor49:57

        Yeah.

    24. HSHarry Stebbings49:58

        So can you even get that data back in the pre-close process?

    25. STSam Taylor50:02

        You're not gonna get it every single time, and it's gonna b- it's honestly going to

19. 50:07 – 51:36

    #1 Reason People won't Buy Loom this Quarter

    1. STSam Taylor50:07

       depend on the relationship that you've built. I think our most successful reps are coming back in that situation where they're saying, "This thing pushed, and I had the opportunity, and I asked why, and I got a real answer on why." And that could be, "There are other things that are in the pipeline that took precedent, and here's the reasons that those took place." Uh, you get insights into what are the either decision-making, political, whatever the dynamics are in terms of how things are prioritized at that company. And you get better insight into, how do we position and how do we work with that champion to move us to the top or higher up on the list that it is prioritized? Um, but that is really where you have to anchor in the relationships that you're building, so you can have the candid conversations from there. Uh, I'd say if you're seeing reps on your team that are consistently getting the, "We're pushing," and when you ask, "Well, why и how would we avoid it?" and they haven't been able to go back and have those conversations, again, not saying you're gonna be able to have it every single time. But if you're building deep relationships that are rooted in understanding your customer, understanding what is valuable to them, and understanding their priorities, y- you should have a higher hit rate on that, in my opinion.

    2. HSHarry Stebbings51:17

       Yeah. And that's when you say, "You're fired." (laughs)

    3. STSam Taylor51:22

       (laughs)

    4. HSHarry Stebbings51:22

       No, I'm joking. Uh-

    5. STSam Taylor51:23

       I don't wanna work for you, Harry. Let me tell you. (laughs)

    6. HSHarry Stebbings51:24

       Yeah, "Uh, um, why, why did you accept my offer? Gee." Um, final one for you, and it's just us on the line, so it's all cool.

    7. STSam Taylor51:31

       Oh, of course.

    8. HSHarry Stebbings51:31

       What's the number one... wh- what's the number one reason why enterprises don't buy Loom this quarter?

20. 51:36 – 52:28

    What sales tactics haven't changed in the past 5 years?

    1. HSHarry Stebbings51:37

    2. STSam Taylor51:38

       Well, I think broadly, we're in a macro environment where everyone is just looking at spend across the board. If we take that off the table, I think that we at Loom are still in the very early innings of showing up as a enterprise initiative. And when I say that specifically, it's... We have so much momentum and goodness that's happening across the organic growth that we're seeing, the early customer base that we have, and this is always going to be that chasm crossing that we're going through. And so I'd say for us today, it's, how do we actually educate on this category? And then how do we lead folks to understanding the value that they're gonna be receiving particularly in the enterprise? And I think for us, we're, we're still pushing on,

21. 52:28 – 52:53

    The biggest mistake founders make when hiring Sales Teams

    1. STSam Taylor52:28

       what does that look for us, like for us in the tens of thousand of employee organizations? Um, and how do we package up the goodness that we're seeing in smaller companies and bring it to them?

    2. HSHarry Stebbings52:38

       I, uh, no, I totally with you. I find also just the category creation play when you move into enterprise and the stodginess of mindsets, yeah, challenging. But if anyone-

    3. STSam Taylor52:48

       Yeah.

    4. HSHarry Stebbings52:48

       ... can do it, Sam, it is you. Um-

    5. STSam Taylor52:51

       Heck yes.

    6. HSHarry Stebbings52:52

       Heck yeah. So are you ready

22. 52:53 – 54:04

    Biggest Advice for New Sales Leaders

    1. HSHarry Stebbings52:53

       for a quick fire? I say a short statement, you give me your immediate thoughts.

    2. STSam Taylor52:56

       Let's do it.

    3. HSHarry Stebbings52:57

       All right, let's do, what sales tactics have not changed over the last five years?

    4. STSam Taylor53:04

       The genuine and authentic curiosity in understanding your customer's needs is the consistent... Like, how does that play into your discovery? How does that play into your approach? If you're going deep and being extremely focused on va- al- adding value to your customer, you gotta stay consistent.

    5. HSHarry Stebbings53:23

       What sales tactics have died a death?

    6. STSam Taylor53:27

       I think with all the automation that's taking place, particularly on the mostly email side, I think there's just an exhaustion around, around email today. And so trying to find ways to cut through that noise in different, more compelling ways.

    7. HSHarry Stebbings53:44

       Whenever I get email, there's, like, a notification function for, like, unsubscribe. (laughs)

    8. STSam Taylor53:49

       (laughs)

    9. HSHarry Stebbings53:49

       You know what I mean?

    10. STSam Taylor53:50

        It's a tough one.

    11. HSHarry Stebbings53:51

        Yeah. Uh, tell me, what would you say is the biggest mistake founders make when hiring sales and revenue teams?

    12. STSam Taylor54:00

        Not being intentional into the integration with the rest

23. 54:04 – 54:46

    What's the one thing you wish you could change about Sales today?

    1. STSam Taylor54:04

       of the company. How do we make this be an unlock and a superpower f- and learning engine for the company, um, as opposed to it ending up being kind of an orphaned function?

    2. HSHarry Stebbings54:14

       Flip it, baby. We've got a new sales leader, and they're joining a company. What advice would you give them on coming in?

    3. STSam Taylor54:23

       It's all about relationship building cross-functionally. Because if you're, if you're delivering feedback or if there's things that you have conviction that you've learned that you wanna be doing from a go-to-market perspective, but it's falling on deaf ears, or you don't have the credibility to deliver that in the right way, um, you have to go deep on those relationships. At, at Loom, my

24. 54:46 – 56:56

    What's one company's sales strategy that impresses you?

    1. STSam Taylor54:47

       partnership with Anique, who is our VP of product, and us being on the same page around what are we learning, how are we approaching, how are we thinking about the trade-offs, how do we be in the boat together on going and building a business across our different funnels and go-to-market motions, that unlocks so much efficiency and speed in what we're doing. And so, um, as you're taking that approach then, your job is to also learn how to be a translator coming in. And this is probably a longer answer than the quick fire that we're saying, but, uh, I wholeheartedly believe that a huge part of success early days is being able to take what you're seeing from the customer and find the right ways to articulate it to the different parties within the company.

    2. HSHarry Stebbings55:25

       Other than cross-functional relationships, what is the one thing you'd like to change most about sales today?

    3. STSam Taylor55:32

       I think we're still fighting the, the ali- the, the potential misalignment between what I just said is the most important thing at, at the, the top of this rapid fire, which is, like, your genuine curiosity and customer, uh, understanding and value that you're driving for them, um, and the way in which sales can be perceived particularly on the coin op side of things of just here for the paycheck. Uh, and so how do we, how do we do away with the latter, and how do we be there be a celebration of what we're learning and uncovering and the value that we're driving? So it's a perception on sales.

    4. HSHarry Stebbings56:09

       What one company sales strategy have you been most impressed by recently?

    5. STSam Taylor56:14

       It's, uh, it's close to home. Um, my wife, Kate, who you've chatted with in the past, is, is over at Notion. And I think that Notion has done an amazing job of unlocking and unleashing the power of their community as a, a way to compound not only their growing user base but the ecosystem that they're building in terms of monetization. I think community is a, a huge part of what they're doing and something I'm taking notes on.

    6. HSHarry Stebbings56:41

       Let's be honest. You were sleeping on the sofa if you didn't say that. (laughs)

    7. STSam Taylor56:45

       (laughs) 1000%.

    8. HSHarry Stebbings56:46

       Sam, thank you so much for joining me. I absolutely love our chats, and you're so brilliant to chat to, so huge thank you.

    9. STSam Taylor56:53

       Harry, as always, appreciate it. So great to see you.

Episode duration: 56:56