The Exchanges

Q 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?

A 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 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, because we're 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 10 years, and you being able to have those relationships, but also the context of what it takes to build in the early days is actuall…

AI assessment note: “make sure that those people are inserted into our hiring panel”

Q And then after this indoctrination, do we do a, do we do a test? Do we say, all right, Sam, you've, you've had two weeks on, on the coaching academy. Sell me this pen.

A 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 going to be much more of the company and cross-functional as we get into their second, third, and fourth weeks. Um, very much going to 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 teams. They can get feedback as well.

AI assessment note: “by the end of the second week that someone's here, they are doing a full demonstration”

Q When do I need to bring Moola in the cooler? 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?

A I think broadly I look at this from a segment perspective because you're going to have different, different deal cycles and different 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 two X 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 are we making in terms of multi threading into your accounts? Uh, what early commitments are we getting in terms of pilot engagement, uh, structure and criteria there? What is our path to you starting to put yourself in 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 …

AI assessment note: “within the first 90 days, you should start to see deal flow”

Q I'm a little bit intimidated 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. So I guess my question is, what can leaders do to create that engagement in a world where it has to be manufactured more?

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

AI assessment note: “We literally give people a list of cross-functional folks that should be on their”

Q that. Um, can I ask you one thing that I find, a 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.

A Totally. Um, so I'd say iterative 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 or 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 bi-weekly. 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 going to be making mistakes and we're not going to bat 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 ma…

AI assessment note: “the cadence with which we're doing it at this point is bi-weekly.”

Q 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. 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 frameworks, or is it okay for it to be brought in by a sales leader?

A 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 it, 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? Can they deliver that message credibly? So I think the iteration then becomes what are the nuggets and what are the key value areas that have been uncovered during early customer wins or even losses? 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 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 conversations that you're doing, or actually taking the time to allow them to write shotgun on 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 going to be a huge unlock and highly applicable and inserted into the frameworks that that customer facing person is going to be able to reuse. And so don't discount the special sauce that you've practiced.

AI assessment note: “I'd kind of call bullshit on the founder can't create it.”

Q super nice and personal and human to another thing that I was intrigued that Xenia 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? Like, how, do you like case studies, and should I use them as a founder in this process?

A 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.

AI assessment note: “I don't like case studies because I think they're overly structured.”

Q You know, fake humility is always good to have. Um, but 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?

A 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 give in or unpack what that means. Take the whole show. Um, but ultimately, uh, got my start on both the technology and sales side at Salesforce back in 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 I've been having the opportunity to learn from and work with some amazing teams between the Dropbox crew slash 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.

AI assessment note: “got my start on both the technology and sales side at Salesforce”

Q 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?

A 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 want to 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 loom my. 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, 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.

AI assessment note: “It's all about relationship building cross-functionally because”

Q What would be a type of problem? Just so I have an idea.

A Sure. Um, You could have it be customer objections. Uh, we're, we're consistently hearing X. Someone's not comfortable. 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 something 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 as something that would be applicable for someone that's really, really generalist as opposed to sales specific. I think that if you're looking, go ahead.

AI assessment note: “You could have it be customer objections.”

Q 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?

A I think variable compensation is an excellent lever at the right time, 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, that 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 continuing to build that, um, that conviction and what the target 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 based 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 act…

AI assessment note: “don't think the right time is going to be your first couple of hires”

Q So now we've hired this first person. We've gone through that process. They've accepted our offer. Fantastic. It's the first sales hires and I'm busy found. I'm fundraising as well. Uh, I rock up for first day. How do I do onboarding? What, what does that look like?

A 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 loom mate? 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 loom mates, 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, if we're going back to that workflow therapist analogy earlier on, um, what's your perspective on the workplace today? What, what are we, what are we seeing in terms of trends? What are we seeing in terms of experiences, um, that we are trying to lead peo…

AI assessment note: “fast follow to that is product evangelism requires product knowledge, and so how do we go deep”

Q What are the biggest mistakes you see founders make in the hiring process?

A One, not having clarity on what they want. Mm-hmm. Early on, like, what is, what is the actual goal of this role? And, and 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 going to 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, You can't have it all right, and so I think that you just need to have really clear conviction around what it is that you're hiring for, why, and then how do you structure both the questions that you are going to 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.

AI assessment note: “One, not having clarity on what they want.”

Q And then after this indoctrination, do we do a, do we do a test? Do we say, all right, Sam, you've, you've had two weeks on, on the coaching academy. Sell me this pen.

A 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 going to be much more of the company and cross-functional as we get into their second, third, and fourth weeks. Um, very much going to 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 teams. They can get feedback as well.

AI assessment note: “by the end of the second week that someone's here, they are doing a full demonstration”

Q I'm a little bit intimidated 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. So I guess my question is, what can leaders do to create that engagement in a world where it has to be manufactured more?

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

AI assessment note: “We literally give people a list of cross-functional folks that should be on their”

Q that. Um, can I ask you one thing that I find, a 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.

A Totally. Um, so I'd say iterative 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 or 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 bi-weekly. 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 going to be making mistakes and we're not going to bat 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 ma…

AI assessment note: “the cadence with which we're doing it at this point is bi-weekly”

Q terms of like the product-led growth in the enterprise in tandem, 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?

A 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 multiplayer 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 want to 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 up market, um, that's where you start layering in. Should we have selling capacity that is incremental and complimentary to what you have going on the…

AI assessment note: “I think it depends on the offering that you have”

Q You know me, I never stick to schedule a boring shit. 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, but actually someone else pays for it, and so that's the problem of agency between buyer and consumer. How do you approach that today as a sales leader?

A I think it requires that you have An authentic curiosity to learn from your users, and how do you train and teach your Salesforce 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 going to 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, 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, 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.

AI assessment note: “package them up both from the anecdotes... and then the more broad ROI”

Q So if the sellers are that therapist asking those questions, 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?

A 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? 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 like to ask. What's preventing you from sharing or forcing other folks at the company from using this? Uh, if you are, or they may flip it on their head and be like, no, I'm singing Loom's phrases. It's all over the place. Like we get, we have to go and 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 these success metrics that we want to set up as a part of this sales process that we're using? And so for us, it's really how do you ask open-ended questions around why someone has taken personal…

AI assessment note: “first principles of why were you compelled to go through and sign up?”

Q 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. 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 frameworks, or is it okay for it to be brought in by a sales leader?

A Well, I'd kind of call bullshit on the, 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 value 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 going to be a huge unlock and highly applicable And insert it into the frameworks that that customer facing person is going to be able to reuse. And so don't disco…

AI assessment note: “I'd kind of call bullshit on the, the founder can't create it.”

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

A 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 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 going to be longer. The engagement that you expect earlier on is going to take longer to build the perspective on what is actually resonating versus not is also something that you have to be taking inventory on. And so I think cherishing repeatability and cherishing the. 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 revenues 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…

AI assessment note: “I'd say the early days of, like, knowing it is a muscle that you're building.”

Q super nice and personal and human to another thing that I was intrigued that Xenia 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? Like, how, do you like case studies, and should I use them as a founder in this process?

A 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.

AI assessment note: “I don't like case studies because I think they're overly structured.”

Q What are the biggest mistakes you see founders make in the hiring process?

A One, not having clarity on what they want. Mm-hmm. Early on, like, what is, what is the actual goal of this role? And, and 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 going to 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, You can't have it all right, and so I think that you just need to have really clear conviction around what it is that you're hiring for, why, and then how do you structure both the questions that you are going to 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.

AI assessment note: “One, not having clarity on what they want.”

Q 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?

A I think variable compensation is an excellent lever at the right time, 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, that 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 continuing to build that, um, that conviction and what the target 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 based 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 act…

AI assessment note: “I don't think the right time is going to be your first couple of hires”

Q So if the sellers are that therapist asking those questions, 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?

A 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? 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 like to ask. What's preventing you from sharing or forcing other folks at the company from using this? Uh, if you are, or they may flip it on their head and be like, no, I'm singing Loom's phrases. It's all over the place. Like we get, we have to go and 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 these success metrics that we want to set up as a part of this sales process that we're using? And so for us, it's really how do you ask open-ended questions around why someone has taken personal…

AI assessment note: “why were you compelled to go through and sign up?”

Q founder. I've got us to kind of, um, 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 certain sales loft or whatever we're using? How can I document it for you coming in? So you can go, oh, I've got a treasure trove of, you know, potentials.

A I think the, I don't think it needs to be overly detailed. Like, the lift here, like, there, there's like an eighty-twenty value approach here, absolutely, of who are the folks that you've engaged with 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, that 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, 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 bullet points. I think the recording of calls Is actually where the most value can be had. 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 and it feels intrusive at times. And it feels like, oh my gosh, like, did I even do …

AI assessment note: “I think the recording of calls Is actually where the most value can be had.”

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

A 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 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 going to be longer. The engagement that you expect earlier on is going to take longer to build the perspective on what is actually resonating versus not is also something that you have to be taking inventory on. And so I think cherishing repeatability and cherishing the. 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 revenues 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…

AI assessment note: “I'd say the early days of, like, knowing it is a muscle”

Q 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. 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 frameworks, or is it okay for it to be brought in by a sales leader?

A Well, I'd kind of call bullshit on the, 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 value 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 going to be a huge unlock and highly applicable And insert it into the frameworks that that customer facing person is going to be able to reuse. And so don't disco…

AI assessment note: “I'd kind of call bullshit on the, the founder can't create it.”

Q What would be a type of problem? Just so I have an idea.

A Sure. Um, You could have it be customer objections. Uh, we're, we're consistently hearing X. Someone's not comfortable. 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 something 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 as something that would be applicable for someone that's really, really generalist as opposed to sales specific. I think that if you're looking, go ahead.

AI assessment note: “You could have it be customer objections.”

Q Now you mentioned Loom having a sales team for the past two years, but actually having customers and paying customers for a lot longer. I'm always quite perturbed by this one, which is like before we actually, actually, let's just take a step back in terms of the sales playbook. What does the sales playbook mean to you? Because people have many different definitions.

A 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 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 specific, Specific. How do we start to layer in applicable stories? I think storytelling is such a key part to sales. Uh, and so how do we have releva…

AI assessment note: “I don't love playbook as a term because it sounds rigid... I refer to it as frameworks.”