The Exchanges

Q So you give them a loom problem specifically?

A Yep. And I say, hey, and, uh, we are, like, roughly in this stage of maturity for our loom creator experience. Like, tell us what would, what you would do to, to drive a step change improvement and, and getting more folks to, to create. Pretty broad. You can really take it in any way, and for me, I think it highlights a few hard skills. Like, one is just Can you add clarity of thought to a really ambiguous problem and clear structure that folks can, can be convinced by? I think the, the second thing I look for is real creativity. Can you teach me something new or make me think about something in a completely new way? And I think last one is, um, high effort and preparation. I think like a good take home looks Polished, like well-organized, thorough, smart, and like reads really well. Great. Looks like you've actually gone so far as to like create mocks or tell me about competitors. And I've actually gone through and like maybe recorded looms of different competitors. And I think that level of. Of effort and preparation are highly indicative of, um, how someone will attack something, how quickly and how deeply they, they will attack it. Is it a big and Big investment and a big ask from candidates. Absolutely. Yes, I, I think I'm extremely cognizant and grateful for that, but I think if there's a job you absolutely want, you're gonna put in the effort and preparation, and I actua…

AI assessment note: “Yep. And I say, hey, and, uh, we are, like, roughly in this stage”

Q How quickly do you know when you've made a bad hire in product?

A Probably within the first two to three months. I think it's a few things. I think one is ability to deliver real impact and impact doesn't need to mean you moved a metric. It's like, is your team in a, a healthier spot is, did you drive clarity into a really ambiguous part of the strategy that we haven't had before? I think bad hires spend the first three months Still onboarding and, um, still getting an assessment or the lay of the land. And I think the time from content and information absorption into behavior and impact, three months is plenty of time to see that. If they can't do it, then I don't think they have. I haven't seen yet someone who's able to do it in six months or nine months if they weren't able to do it in, in that first three months.

AI assessment note: “Probably within the first two to three months.”

Q But what does questions are cheap, answers are expensive mean in product?

A Look, for anything that you're shipping, we can ask any question that we want and try to get more information, but there are going to be questions that are absolutely critical to answering such that we are building the right things for customers. There are things that like are important to know and might change some decision making or execution. And then there are a lot of questions that are actually just like, Curiosities, and I think you bring in more and more people, there are gonna be many, many curiosities, and I, I think it's really important to identify when asked a question, which one of these are they, and it should directly correlate with the amount of time I spend grappling with it, because the more time you spend answering questions, I think there are diminishing returns for sure, and it's time you're not spending in actually building the, the product.

AI assessment note: “more time you spend answering questions... it's time you're not spending in actually building”

Q Honestly, I think it's a joke that it's even my job, but, uh, no one's caught me yet. Uh, I wanna start, though, on, like, the love of product. How did you fall in love with product, and when did you realize that actually this was the thing you really wanted to devote your career to?

A I think taking away step back. I know you're not asking for my life story, but growing up, I think I just had a lot of the innate qualities of, of a PM. I think on one end, I was just like a weird kid growing up that loved leadership. I was the type of middle schooler or high schooler who went to leadership camp. I, uh, actually worked on a statewide nonprofit trying to, to lead teams of, of teenagers. And I think If you can lead a group of hormonal teenagers, you're, you're on a pretty good track for the real world. Um, I was also a humanities and very much a multidisciplinary background person. I studied public policy, African-American studies, and so I think everything I did in college was writing and, and clarity to thought. I might have taken maybe two multiple choice exams, but I was pretty much writing straight every day. And I think just generally a really curious person. And so when I got into the real world, I was really fortunate to jump into a rotational program at box. And my last rotation was on product and I was like, oh my God, I can do all of these things without sacrificing on, on any one of them. And knew immediately that this was like the, the kind of dynamic job that, that I wanted.

AI assessment note: “knew immediately that this was like the, the kind of dynamic job that, that I wanted.”

Q So I'm an angel investment of yours and, uh, we've got a great PLG product, uh, and I'm the CPO or the CEO, and we're going to move into enterprise. Uh, because that's where we're being told we need to go. Um, what advice would you give to me, knowing all that you know now, having made and being in that transition?

A Yeah, I'd say two things, um, just in having done both methods, uh, I think one method is, um, working your way up to enterprise, and then, um, I think the second is, like, if you are seeing enterprise demand kind of at the larger scale, what do you do? I think the first mistake we built, we made a few years ago in trying to go after enterprise is, um, not figuring out or learning how to win All the customers in between PLG and enterprise, and you talk to different people, people have different definitions for what constitutes an enterprise customer. But in peak COVID, we were, you know, originally selling to small teams, and suddenly we had very large customers with C-suite execs freaking out about company culture or company productivity. And obviously we were excited that You know, 10, 15,020 thousand employee companies wanted to buy us, and so we jumped straight in trying to build for these customers, and we never figured out our playbook for SMBs mid-market enterprise before then, and that made the jump really hard because obviously demand dried up, and when that happened, we built a bunch of features that, like, not a lot of companies or customers actually needed, and Customers were no longer willing to, to buy wall to wall without that natural usage. And so I think it's really important to figure out your sales motions at SMB and mid market, because you're getting forced …

AI assessment note: “I think the first mistake we made... is not figuring out or learning how to win”

Q You said about being opinionated. I think there's one part of Loom's product which is quite opinionated, which is when you reach 25 videos, I think, it's like a hard cutoff, and it's like you have to delete videos if you want to do more, or you pay more. That is quite an opinionated kind of paywall. How do you, how did you think about that? I'm just interested.

A Yeah, it's a great question. I'd say it evolved over time and it was highly dependent on the business needs. I think very, very early in, um, Wim's journey, it was grow, grow, grow, right? There is this asynchronous video is a pretty new behavior in the market. People were really used to consuming short form video. They were really used to being in, in zoom meetings and live video, but the act of Recording yourself, sending it to people at work was still fairly new. And so goal number one is create a new market behavior and get as many people there as, as quickly as possible. And then I think context also is we, we experienced the COVID boom where everyone suddenly had much larger appetite for adopting any new behavior really. And so in that moment, we actually didn't have those limits. We, um, had a Much higher limit that was actually never enforced. And so we really let people use our paid product kind of to no end. And then obviously COVID bust and revenue pressures came about. And so I think as that period happened, and I think as most companies did, we took a really hard look at our pricing and packaging and figured out what are the right limits to achieve the balance of goals that we need. I think in, in this new phase of Revenue growth being kind of the, the number one north star at our company obviously needed to drive new revenue, but I think the other constraints were…

AI assessment note: “took a really hard look at our pricing and packaging and figured out”

Q How do you change that? Like, what changes?

A I think from a celebrating the types of success, I think in core product growth, we're typically really, really oriented around, have you driven more engagement usage or revenue? And you can usually see that within a quarter. I think for, for enterprise, I think there are a few components to enterprise. I think there's the, there are just some table stakes things that are maybe unsexy to the average core product person. Things like data residency or HIPAA or, or FINRA compliance that, um, you're not actually going to see immediate dollars to you, even if you spend six, nine months building the thing. And that's because sales cycles are much longer. And so for something like that, how do you actually celebrate the top level of the inputs or the pipeline? It's, Hey, by, by actually building out data residency, this is how much more opportunity or how much more of a customer base we've unlocked. In the next quarter, I think the, the, the results that we celebrate may not be purely owned by, by product teams. I, I, I love sharing core outcomes with my sales counterpart. After we build the thing, unlock the revenue, I actually want to see in the next quarter, like how much have we actually been able to turn into pipeline? And that's the thing we celebrate. And I think as you think about these sales cycles being so long, you celebrate the input you can drive and you share those outco…

AI assessment note: “you celebrate the input you can drive and you share those outcomes”

Q Where did that lead you in terms of the end user experience when you're building so much so fast?

A I think it's a, like, very, very iterative cycle. Um, I think when you're selling, and this is kind of the same across so many enterprise products, right? You're selling to a buyer who may not be the user, and you're selling Products that like people don't really get to, to play with or actually use until it's, it's purchased. And so I think it's really creating a clear point of view on what's the minimum level of usability that you need to get the purchasing decision. And then that only gets you partway through the door. If, if the actual users, the admins aren't using the product, you're going to be in trouble. Maybe not now, but a year from now, when people People aren't able to actually administer, like, core critical roles, and so I think making sure that you have a point of view on what gets you sold versus what gets used is probably an, like, an enterprise software wide lesson, but I think you need to do both, even if you separate out the time at which you do the two things, but I don't think you can retain customers without, without doing both.

AI assessment note: “making sure that you have a point of view on what gets you sold versus what gets used”

Q But he's, but he's the CPO of Spotify, and he's much smarter and richer than me, and so clearly I... Maybe miss something. How do you feel when you hear that?

A I agree. How expensive is it to, to actually do the, the cheap talk exploration, and, and when are you doing it? I think timing is really important. I think when you're at the beginning stages, like any, all ideas, like welcome, helpful, but as you get further and further along, I, I, I tend to agree you need to start prioritizing, and when you don't, then I think you actually are causing a ton of distractions, and so When in the process are you collecting this and the types of questions that might be critical at the problem definition stage are no longer critical once you get to, to execution. And so I think it's when and why you're asking matter a ton and you should welcome it, but context and timing matters a ton. And because we ask people to self prioritize, we actually spend time discussing the things that matter. I think you can tell And, and the, the meeting itself, the full 45 minutes to an hour is spent on just the P zeroes. Because we ask people to prioritize, it's probably been the biggest unlock and also allows people to join the conversation. I think in previous worlds, um, it was really hard to open up meetings without sacrificing speed to, to make decisions. And when you force everyone to prioritize, Their questions, context, or thoughts. You're able to scale context much more quickly and still maintain the integrity of, of really focused discussions. And I think…

AI assessment note: “I agree. How expensive is it to, to actually do the, the cheap talk”

Q But he's, but he's the CPO of Spotify, and he's much smarter and richer than me, and so clearly I... Maybe miss something. How do you feel when you hear that?

A I agree. How expensive is it to, to actually do the, the cheap talk exploration, and, and when are you doing it? I think timing is really important. I think when you're at the beginning stages, like any, all ideas, like welcome, helpful, but as you get further and further along, I, I, I tend to agree you need to start prioritizing, and when you don't, then I think you actually are causing a ton of distractions, and so When in the process are you collecting this and the types of questions that might be critical at the problem definition stage are no longer critical once you get to, to execution. And so I think it's when and why you're asking matter a ton and you should welcome it, but context and timing matters a ton. And because we ask people to self prioritize, we actually spend time discussing the things that matter. I think you can tell And, and the, the meeting itself, the full 45 minutes to an hour is spent on just the P zeroes. Because we ask people to prioritize, it's probably been the biggest unlock and also allows people to join the conversation. I think in previous worlds, um, it was really hard to open up meetings without sacrificing speed to, to make decisions. And when you force everyone to prioritize, Their questions, context, or thoughts. You're able to scale context much more quickly and still maintain the integrity of, of really focused discussions. And I think…

AI assessment note: “I agree. How expensive is it to, to actually do the, the cheap talk”

Q What is the tipping point for when you will change product roadmap to gain a segment of revenue? So you have your product roadmap and then deviated well away from it is another product requirement, but it unlocks ten million in ARR from two or three large customers. When do you say, yes, we will deviate versus no, we won't.

A There's the one-off feature answer of, Hey, if certain things hit a certain revenue threshold, let's do it. And I'd say before a company makes a real commitment to enterprise, that's typically the way it's, Hey, create some revenue threshold. The actual number itself, I think is less important and more relative to like what your business needs. And then I think at a larger scale, the, the broader commitment comes from PLG not gonna be enough. And how do we, Kind of anticipate that. I think there's a really great article called the PLG trap. What, um, that starts to outline like why PLG companies to be truly enduring companies need both PLG and sales led. And I think the company needs to figure out at what are they willing to invest to kind of go more full in relative to considering inbound requests at a customer and, and feature by feature level basis.

AI assessment note: “create some revenue threshold. The actual number itself, I think is less important”

Q Where did that lead you in terms of the end user experience when you're building so much so fast?

A I think it's a, like, very, very iterative cycle. Um, I think when you're selling, and this is kind of the same across so many enterprise products, right? You're selling to a buyer who may not be the user, and you're selling Products that like people don't really get to, to play with or actually use until it's, it's purchased. And so I think it's really creating a clear point of view on what's the minimum level of usability that you need to get the purchasing decision. And then that only gets you partway through the door. If, if the actual users, the admins aren't using the product, you're going to be in trouble. Maybe not now, but a year from now, when people People aren't able to actually administer, like, core critical roles, and so I think making sure that you have a point of view on what gets you sold versus what gets used is probably an, like, an enterprise software wide lesson, but I think you need to do both, even if you separate out the time at which you do the two things, but I don't think you can retain customers without, without doing both.

AI assessment note: “point of view on what gets sold versus what gets used”

Q What is the tipping point for when you will change product roadmap to gain a segment of revenue? So you have your product roadmap and then deviated well away from it is another product requirement, but it unlocks ten million in ARR from two or three large customers. When do you say, yes, we will deviate versus no, we won't.

A There's the one-off feature answer of, Hey, if certain things hit a certain revenue threshold, let's do it. And I'd say before a company makes a real commitment to enterprise, that's typically the way it's, Hey, create some revenue threshold. The actual number itself, I think is less important and more relative to like what your business needs. And then I think at a larger scale, the, the broader commitment comes from PLG not gonna be enough. And how do we, Kind of anticipate that. I think there's a really great article called the PLG trap. What, um, that starts to outline like why PLG companies to be truly enduring companies need both PLG and sales led. And I think the company needs to figure out at what are they willing to invest to kind of go more full in relative to considering inbound requests at a customer and, and feature by feature level basis.

AI assessment note: “create some revenue threshold. The actual number itself, I think is less important”

Q What are the biggest reasons super days don't convert?

A One thing that I love in our super day outside of the typical one-on-ones you have with leadership, cross-functional partners, is actually a 45 minute hour deep dive on the take home itself. So everyone, it, it's a small group of people within Loom who show up. They've actually gone through your take home already, have watched a Loom, and just come prepared with a bunch of questions. And They're not meant to be trick questions. We treat them as we would, um, in a product review, which is, hey, we have a bunch of questions. We want to learn more. Let's use the time to up level, like craft and quality of decisions. And I think the candidate's ability to interact with the team is really, really high signal. Like I said earlier, like when asked hard questions, um, are they curious or are they defensive? Um, when are they open to, to being challenged? And like, when do they have really high conviction? Do they have any high conviction at all? Um, and, and are willing to defend some of their points of view? Are they willing to be open to others? And, um, how do you actually just naturally work with other folks? I think this environment is pretty akin to what you would be doing in your day to day, uh, with the team. And so I think it's, As close to, like, real life simulation as possible, and it's not a random case study. You've already taken the time to think through this, and so I t…

AI assessment note: “when asked hard questions, um, are they curious or are they defensive?”

Q What are the biggest reasons super days don't convert?

A One thing that I love in our super day outside of the typical one-on-ones you have with leadership, cross-functional partners, is actually a 45 minute hour deep dive on the take home itself. So everyone, it, it's a small group of people within Loom who show up. They've actually gone through your take home already, have watched a Loom, and just come prepared with a bunch of questions. And They're not meant to be trick questions. We treat them as we would, um, in a product review, which is, hey, we have a bunch of questions. We want to learn more. Let's use the time to up level, like craft and quality of decisions. And I think the candidate's ability to interact with the team is really, really high signal. Like I said earlier, like when asked hard questions, um, are they curious or are they defensive? Um, when are they open to, to being challenged? And like, when do they have really high conviction? Do they have any high conviction at all? Um, and, and are willing to defend some of their points of view? Are they willing to be open to others? And, um, how do you actually just naturally work with other folks? I think this environment is pretty akin to what you would be doing in your day to day, uh, with the team. And so I think it's, As close to, like, real life simulation as possible, and it's not a random case study. You've already taken the time to think through this, and so I t…

AI assessment note: “One thing that I love in our super day outside of the typical one-on-ones”