The Exchanges

Q And then you hit me with your immediate thoughts. This one's not on the sheet, but I'm just interested. What skill do you think is really important for product leaders that you don't think you have yet?

A I think it's storytelling at scale. I think at every level of Product management. You need to be a great storyteller and audience and reach that you have changes at progressive parts of your career, but even at progressive parts of company growth and, and team growth. And so I think this is something that I'm just always working on, which is this moment in time is distinctly different from even a quarter ago or two quarters ago. Like the storytelling that I was doing To reach, you know, 200 people at Loom is gonna be very different than the storytelling I need now at Atlassian, where we have 10,000 employees, more than 16 products. Everyone has very, very different time zones and priorities, and so I think that's something I'm just constantly working on, is how do I tell a story at the various points in time of, of company and, and team growth.

AI assessment note: “I think it's storytelling at scale.”

Q I mean, there's, there's many elements that I want to kind of later on, especially the element of writing. I do want to just ask, you've worked at some incredible places kind of throughout your years now, and some of them include obviously Opendoor and Rippling, and I was told specifically by some people to focus on Opendoor, and first, what was your biggest lessons on pricing from Opendoor?

A I'd call out two things. I think first is I really learned how to be a GM and a business owner. I think being a PM at a low margin business is one of the best things you can do. To, to grow your business acumen. And I've since, since then have only worked at SAS companies, but in, in the world of pricing, accuracy and all the details mattered so much. One mispriced tone could wipe out the profit of 20 or, or 40 homes. And so just the act of needing to be right and margins playing such a huge factor really caused me to get into every component of understanding the profitability of a home. And Um, with our pricing algorithms, we had to understand things like outliers, and that required us to go deep and do a case studies on every time we got it wrong. And on the flip side, celebrate when we shipped wins to our pricing algorithms that saved a few basis points. I think I rarely have said the term basis points in a SaaS setting, and I think this attention to detail, knowing the full P and L of a business is The, the type of business acumen that I think serves me especially well in, in SAS settings, knowing the inputs and outputs. I think the other one is just, uh, learning in, in building products, how to combine automated automation with human touch. I think when you're building ML or AI products, you always go with the mindset of everything needs to be automated or like this needs…

AI assessment note: “in the world of pricing, accuracy and all the details mattered so much.”

Q I mean, there's, there's many elements that I want to kind of later on, especially the element of writing. I do want to just ask, you've worked at some incredible places kind of throughout your years now, and some of them include obviously Opendoor and Rippling, and I was told specifically by some people to focus on Opendoor, and first, what was your biggest lessons on pricing from Opendoor?

A I'd call out two things. I think first is I really learned how to be a GM and a business owner. I think being a PM at a low margin business is one of the best things you can do. To, to grow your business acumen. And I've since, since then have only worked at SAS companies, but in, in the world of pricing, accuracy and all the details mattered so much. One mispriced tone could wipe out the profit of 20 or, or 40 homes. And so just the act of needing to be right and margins playing such a huge factor really caused me to get into every component of understanding the profitability of a home. And Um, with our pricing algorithms, we had to understand things like outliers, and that required us to go deep and do a case studies on every time we got it wrong. And on the flip side, celebrate when we shipped wins to our pricing algorithms that saved a few basis points. I think I rarely have said the term basis points in a SaaS setting, and I think this attention to detail, knowing the full P and L of a business is The, the type of business acumen that I think serves me especially well in, in SAS settings, knowing the inputs and outputs. I think the other one is just, uh, learning in, in building products, how to combine automated automation with human touch. I think when you're building ML or AI products, you always go with the mindset of everything needs to be automated or like this needs…

AI assessment note: “in the world of pricing, accuracy and all the details mattered so much.”

Q What was the most recent wow moment you have with a consumer product and why, why was that a wow moment for you?

A I recently went to kind body. It's a women's healthcare provider in, in the U S and it's not that new of a, of a company, but it is one of the best healthcare experiences I've had. And also a mix of software in-person services, and just, I think pushing the boundaries on a really difficult industry to move. And I think after working in real estate, I have deep appreciation for that. And I think the, the things that I loved, Walked in, physical space and services were unlike anything I've ever experienced before, and it mattered a lot in, like, how I felt. I walk into, to Kindbody, walls are neutral color, amazing furniture, like, smells great, and when you're dealing with a healthcare experience, there's just, like, an immediate sense of, like, relief and calmness that comes in, and then I think in, in all of their services, they do an insane thing in healthcare, which is provide transparent pricing. And it's literally up front and center, and they tell you, if you want this service without insurance, it's gonna cost this much. If you want this service, it's gonna cost that much. And I think that just both engenders trust, but is, is something that I've never experienced before. And then I think the, the last bit is they've, they use software to, to tie it all together. Um, and so they have a health portal like most healthcare providers. I think the, Functionality is, is roughl…

AI assessment note: “I recently went to kind body. It's a women's healthcare provider”

Q The more specific, the better, so never, ever worry about that. Can I ask you, what are the biggest mistakes that you see PMs make when it comes to writing?

A I think people often share their writing before they get to, to distillation, and so I, I think people oftentimes mistake, like, volume of writing with depth of thought or clarity of thought, and you can get into a document, a strategy or PRD, be on page eight and still ask yourself, I don't know what I'm reading. There are a lot of details here. There are a lot of edge cases or requirements, but It, but I still don't know what, why, and how. And so I think that's number one, which is especially for folks who are trying to get better before you think it's ready. You probably want to take five more revs at, at simplifying is, is the biggest one. I think that the second one is not knowing who your audience is. Um, writing for an exec team to manage up is very different for writing for your engineering team. Who's going to take This and turn it into two lines of code and the level of, of context they need is very different, but also the, the language and the why is, is very, very different. And so I'd call out those two as the, the things that I see most often.

AI assessment note: “I think people often share their writing before they get to, to distillation”

Q And then you hit me with your immediate thoughts. This one's not on the sheet, but I'm just interested. What skill do you think is really important for product leaders that you don't think you have yet?

A I think it's storytelling at scale. I think at every level of Product management. You need to be a great storyteller and audience and reach that you have changes at progressive parts of your career, but even at progressive parts of company growth and, and team growth. And so I think this is something that I'm just always working on, which is this moment in time is distinctly different from even a quarter ago or two quarters ago. Like the storytelling that I was doing To reach, you know, 200 people at Loom is gonna be very different than the storytelling I need now at Atlassian, where we have 10,000 employees, more than 16 products. Everyone has very, very different time zones and priorities, and so I think that's something I'm just constantly working on, is how do I tell a story at the various points in time of, of company and, and team growth.

AI assessment note: “I think it's storytelling at scale.”

Q No, no, I actually just prefer writing on my hand. It's kind of easier. Uh, so my, my number one is you said there about kind of, is it as simple as it could be? Janie, is simple always better in product?

A I think it depends on who you're building for, but I think generally, yes, I do really, really believe in progressive disclosure in product experiences. And so I think in a world where you know exactly who your user is, exactly what they want, can you be as hyper-specific and personalized as possible? Absent that, how do you become really, really opinionated on Um, you know, in a given experience, what are the, the first level of actions you may want to take and only expose more if, if you really, really show interest in wanting to take that. But I do think, and this is a, a core product principle of, of Loom is it just has to be simple, fast, and easy for a product to, to be loved and adopted. I think there are obviously nuances and edge cases where, uh, the, the complexity Is required, but I'd say for most products on average, the simple, easy to want, easy to use ones often win.

AI assessment note: “I think it depends on who you're building for, but I think generally, yes”

Q Final one before we do a quick fire is just like product reviews are a cool part of The role of a product leader. How do you do product reviews? How do you structure them? Who's invited? Who sets the agenda? Just help me understand that.

A We have two types of product reviews that we have hold, holds on the calendar for every week. One is an exec review, and one is more of a casual product crit. The exec reviews are typically for products that are really high stakes because they're high cost, really strategic, One way door type products where if we get it wrong, it's going to be really bad. Um, and so for these reviews, uh, I, other execs will at the beginning of the quarter say like this product needs to go through the review cycle or PMs can self nominate. And I think there are different types of discussions that happen in these exact reviews based on the product life cycle. If it's earlier on, it's problem definition, like We're not looking at mocks. We're just saying, are we solving the right business and customer pain point? And you have to identify both. You have to identify what is the business outcome we're, we're achieving and like, how are we making our customers lives better? And then I think as, as products get more mature, um, and are farther along in their life cycle, we start to get into solutions and we have exact reviews on, on the solutions. Um, want the product teams to come to the table with a few options, but be really, Which one they recommend? And then I think the last one is a bit more in the weeds on execution. So once the team has built out the solution, um, how do we gain confidence tha…

AI assessment note: “We have two types of product reviews that we have hold, holds on the calendar”

Q I'm a product leader measuring the skills of a PM. So, totally agree with you there. Another, I had so many, like, where they said, Janie's great at this, and I wanted to unpack it. Apparently, you're amazing at question asking, which is something that I spend a lot of time thinking about being, obviously, an interviewer. What are your biggest lessons on what it takes to ask great questions?

A I think for anything that Is coming my way or, or to my desk. I have to be able to answer like some combination of these questions for myself. And if I can't, then that's when I ask a question. I think the, the first is just like, can I explain really simply like what it is we're doing and like, why are we doing this? And am I convinced it's worthwhile? If not, like, let's not take this conversation any, any further. Like we have to have to get to good resolution here. Otherwise, the solution, how we get there, the people you need to get there, they don't matter. And so I think that's my first level of, like, am I convinced and, like, can I explain it? If not, like, that's fine. You might have a great answer, and I'm just not there yet, and you need to explain it to me. Or maybe I'm there, and we just haven't gotten to, like, the root cause of why. And then I think as we get to, like, more of the secondary tertiary level of questions, I think it's, like, Can I, for myself, identify, like, the most important things that we need to answer or The biggest risks. Um, if, if yes, like what is the relative cost of not answering those or, or like getting the answer wrong? And I think that will determine like, how deep do I go? If it's really, really consequential, I'm going to keep digging in. If it's not consequential, I don't want to create more work for my team. And so I might still…

AI assessment note: “how deep do I go is really, really dependent on like, what is the risk”

Q What was the most recent wow moment you have with a consumer product and why, why was that a wow moment for you?

A I recently went to kind body. It's a women's healthcare provider in, in the U S and it's not that new of a, of a company, but it is one of the best healthcare experiences I've had. And also a mix of software in-person services, and just, I think pushing the boundaries on a really difficult industry to move. And I think after working in real estate, I have deep appreciation for that. And I think the, the things that I loved, Walked in, physical space and services were unlike anything I've ever experienced before, and it mattered a lot in, like, how I felt. I walk into, to Kindbody, walls are neutral color, amazing furniture, like, smells great, and when you're dealing with a healthcare experience, there's just, like, an immediate sense of, like, relief and calmness that comes in, and then I think in, in all of their services, they do an insane thing in healthcare, which is provide transparent pricing. And it's literally up front and center, and they tell you, if you want this service without insurance, it's gonna cost this much. If you want this service, it's gonna cost that much. And I think that just both engenders trust, but is, is something that I've never experienced before. And then I think the, the last bit is they've, they use software to, to tie it all together. Um, and so they have a health portal like most healthcare providers. I think the, Functionality is, is roughl…

AI assessment note: “I recently went to kind body. It's a women's healthcare provider”

Q said that, because I'd love for you to have an opinion on a question on art versus science, and, and we're not allowed to be in the middle, Janie, ok? So we have to have an opinion, which is very important apparently. So is product more art or science? If you were to assign numbers to it, which gives you a little bit of leeway, where would you put it?

A I know I'm cheating. Probably 6040 more art than science. I think there is an art in diagnosis and science in how to execute, and I think the art of being a product person is, can you identify what scenario you're in? And then can you then figure out what tool in your toolkit that you want to use to solve the scenario? And I think the, the science aspect of pulling on your, your toolkit is interesting because early in your career, you don't have a ton of tools in your toolkit. Most PMs are typically really great at one thing, something like execution, um, or something like writing a doc. And I think people expand their toolkit over time. And mostly by just getting the reps in of building and being in different circumstances. But I think that the ability to diagnose like what situation am I in and, and what do I need to do to solve it is art because I think there's just so much nuance and context that there isn't going to be a straightforward formula or framework for, for every single situation you find yourself in. I think like when there's this function on your team, You, you might need a great strategy because of the team has no, no, no north star. You might not need a great strategy. Like the team might be in such a bad place that you just need some quick wins for whatever it is just to get velocity. Um, and so I think because of all of the different permutations of context …

AI assessment note: “Probably 6040 more art than science.”

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 How do you want to make users feel? You said there about, it's about how you make them feel. How do you want users to feel as a product creator and as a PM?

A I want them to feel like superheroes. It sounds a little bit. Ultimately our job as product people is to make people do their daily tasks or solve their biggest problems in a way that makes them better than they were before. And so when people are using our product, I think I want them to feel like they've accomplished something, feel like they've gained a ton of value and feel like There are better product people, employees, um, humans as a result of using the product. And I think you can do that. I think both by choosing the right problems to solve, but the other bit is like how you celebrate cus users and customers on the product matter a ton. And sometimes you also have to make that ROI and value they're getting really, really explicit because, um, some people will kind of just go through the motions and Know that the product is helpful, but may not realize to what extent. And so, whether it is, like, specifically how much time you've saved, or the fact that, like, you just actually reached way more people than you would have had you, like, gone with another way of communicating. I think you, you, it's also our job to, to make people feel those things explicitly as, as well as implicitly by, by solving the core problem as well.

AI assessment note: “I want them to feel like superheroes.”

Q The more specific, the better, so never, ever worry about that. Can I ask you, what are the biggest mistakes that you see PMs make when it comes to writing?

A I think people often share their writing before they get to, to distillation, and so I, I think people oftentimes mistake, like, volume of writing with depth of thought or clarity of thought, and you can get into a document, a strategy or PRD, be on page eight and still ask yourself, I don't know what I'm reading. There are a lot of details here. There are a lot of edge cases or requirements, but It, but I still don't know what, why, and how. And so I think that's number one, which is especially for folks who are trying to get better before you think it's ready. You probably want to take five more revs at, at simplifying is, is the biggest one. I think that the second one is not knowing who your audience is. Um, writing for an exec team to manage up is very different for writing for your engineering team. Who's going to take This and turn it into two lines of code and the level of, of context they need is very different, but also the, the language and the why is, is very, very different. And so I'd call out those two as the, the things that I see most often.

AI assessment note: “people oftentimes mistake, like, volume of writing with depth of thought”

Q In what way, like write PRDs more, write updates for teams more, like what should I write?

A All of the above. I literally, for folks who on my team are trying to get better at writing, I kind of anchor on a few things as really, really tactical tips. I think there's the, the PRD aspect, it's much higher stakes and so requires a ton of revs, which is everything you need to do needs to be a great PRD for someone who is not good at it. You need to get started earlier, get more revs in and get the feedback before it's at a place where people are ready to consume. I think another easier day to day, lower stakes way to get better at writing is taking the mindset of how do I make Every single meeting I have more effective by clear writing. And so from a pre-meeting perspective, it's, Hey, like you should actually send out the goals and the agenda and the like desired outcomes of your meeting to everyone that is attending like a day before the meeting. I think it requires you to clarify your own thoughts of what is the best possible outcome of this? And then, um, do people know what they're expected to do as they get here? As they get to the meeting, I think after meetings is also something that I encourage PMs to be great at, which is after the meeting happened, how do you distill the key takeaways and the summaries simply and the action items? And if you take one look at it, it might feel like a lot of program management, but I think on the other hand, it also feels like fo…

AI assessment note: “All of the above.”

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

Q No, no, I actually just prefer writing on my hand. It's kind of easier. Uh, so my, my number one is you said there about kind of, is it as simple as it could be? Janie, is simple always better in product?

A I think it depends on who you're building for, but I think generally, yes, I do really, really believe in progressive disclosure in product experiences. And so I think in a world where you know exactly who your user is, exactly what they want, can you be as hyper-specific and personalized as possible? Absent that, how do you become really, really opinionated on Um, you know, in a given experience, what are the, the first level of actions you may want to take and only expose more if, if you really, really show interest in wanting to take that. But I do think, and this is a, a core product principle of, of Loom is it just has to be simple, fast, and easy for a product to, to be loved and adopted. I think there are obviously nuances and edge cases where, uh, the, the complexity Is required, but I'd say for most products on average, the simple, easy to want, easy to use ones often win.

AI assessment note: “I think it depends on who you're building for, but I think generally, yes”

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 it's really important to figure out your sales motions at SMB and mid market”

Q I'm a product leader measuring the skills of a PM. So, totally agree with you there. Another, I had so many, like, where they said, Janie's great at this, and I wanted to unpack it. Apparently, you're amazing at question asking, which is something that I spend a lot of time thinking about being, obviously, an interviewer. What are your biggest lessons on what it takes to ask great questions?

A I think for anything that Is coming my way or, or to my desk. I have to be able to answer like some combination of these questions for myself. And if I can't, then that's when I ask a question. I think the, the first is just like, can I explain really simply like what it is we're doing and like, why are we doing this? And am I convinced it's worthwhile? If not, like, let's not take this conversation any, any further. Like we have to have to get to good resolution here. Otherwise, the solution, how we get there, the people you need to get there, they don't matter. And so I think that's my first level of, like, am I convinced and, like, can I explain it? If not, like, that's fine. You might have a great answer, and I'm just not there yet, and you need to explain it to me. Or maybe I'm there, and we just haven't gotten to, like, the root cause of why. And then I think as we get to, like, more of the secondary tertiary level of questions, I think it's, like, Can I, for myself, identify, like, the most important things that we need to answer or The biggest risks. Um, if, if yes, like what is the relative cost of not answering those or, or like getting the answer wrong? And I think that will determine like, how deep do I go? If it's really, really consequential, I'm going to keep digging in. If it's not consequential, I don't want to create more work for my team. And so I might still…

AI assessment note: “I have to be able to answer like some combination of these questions for myself.”

Q Final one before we do a quick fire is just like product reviews are a cool part of The role of a product leader. How do you do product reviews? How do you structure them? Who's invited? Who sets the agenda? Just help me understand that.

A We have two types of product reviews that we have hold, holds on the calendar for every week. One is an exec review, and one is more of a casual product crit. The exec reviews are typically for products that are really high stakes because they're high cost, really strategic, One way door type products where if we get it wrong, it's going to be really bad. Um, and so for these reviews, uh, I, other execs will at the beginning of the quarter say like this product needs to go through the review cycle or PMs can self nominate. And I think there are different types of discussions that happen in these exact reviews based on the product life cycle. If it's earlier on, it's problem definition, like We're not looking at mocks. We're just saying, are we solving the right business and customer pain point? And you have to identify both. You have to identify what is the business outcome we're, we're achieving and like, how are we making our customers lives better? And then I think as, as products get more mature, um, and are farther along in their life cycle, we start to get into solutions and we have exact reviews on, on the solutions. Um, want the product teams to come to the table with a few options, but be really, Which one they recommend? And then I think the last one is a bit more in the weeds on execution. So once the team has built out the solution, um, how do we gain confidence tha…

AI assessment note: “We have two types of product reviews that we have hold, holds on the calendar”

Q said that, because I'd love for you to have an opinion on a question on art versus science, and, and we're not allowed to be in the middle, Janie, ok? So we have to have an opinion, which is very important apparently. So is product more art or science? If you were to assign numbers to it, which gives you a little bit of leeway, where would you put it?

A I know I'm cheating. Probably 6040 more art than science. I think there is an art in diagnosis and science in how to execute, and I think the art of being a product person is, can you identify what scenario you're in? And then can you then figure out what tool in your toolkit that you want to use to solve the scenario? And I think the, the science aspect of pulling on your, your toolkit is interesting because early in your career, you don't have a ton of tools in your toolkit. Most PMs are typically really great at one thing, something like execution, um, or something like writing a doc. And I think people expand their toolkit over time. And mostly by just getting the reps in of building and being in different circumstances. But I think that the ability to diagnose like what situation am I in and, and what do I need to do to solve it is art because I think there's just so much nuance and context that there isn't going to be a straightforward formula or framework for, for every single situation you find yourself in. I think like when there's this function on your team, You, you might need a great strategy because of the team has no, no, no north star. You might not need a great strategy. Like the team might be in such a bad place that you just need some quick wins for whatever it is just to get velocity. Um, and so I think because of all of the different permutations of context …

AI assessment note: “Probably 6040 more art than science. I think there is an art in diagnosis”

Q What are those tactics for developing product intuition and taste? As someone who's frequently told I have little taste.

A Yeah, I think there are, are a few things throughout the, the product process. I think When folks are crafting the strategy or just understanding a product, I think it's asking yourself, like, can I crisply articulate the customer problem and why this has to be solved? And you can ask a ton of PMS. You don't always get a great answer. And so I think that's number one is just being so clear on the why. And I think the other bit is, um, being able to articulate how you would talk about this in the market. And I think that gives you a really good foundation of why you're building, why you're building something, what is the value for customers and how do I actually sell it? And so I think that gives you the foundational framework. And then I think as we get into like very, very tactical, like how do you. Create the pixels of something that users will just absolutely love. I think there are probably a few questions. I always ask it's, is this as simple and intuitive for the user as possible? If it's not like, why is that? Um, how does this experience actually make me feel? And can, can, or does this actually make sense across the global product experience? I think product leaders, product managers, just hyper optimized for the thing that they own and actually forcing people to think about everything might actually change the outcome or the outputs of, of their solution. And then I t…

AI assessment note: “I think it's asking yourself, like, can I crisply articulate the customer problem”

Q How do you want to make users feel? You said there about, it's about how you make them feel. How do you want users to feel as a product creator and as a PM?

A I want them to feel like superheroes. It sounds a little bit. Ultimately our job as product people is to make people do their daily tasks or solve their biggest problems in a way that makes them better than they were before. And so when people are using our product, I think I want them to feel like they've accomplished something, feel like they've gained a ton of value and feel like There are better product people, employees, um, humans as a result of using the product. And I think you can do that. I think both by choosing the right problems to solve, but the other bit is like how you celebrate cus users and customers on the product matter a ton. And sometimes you also have to make that ROI and value they're getting really, really explicit because, um, some people will kind of just go through the motions and Know that the product is helpful, but may not realize to what extent. And so, whether it is, like, specifically how much time you've saved, or the fact that, like, you just actually reached way more people than you would have had you, like, gone with another way of communicating. I think you, you, it's also our job to, to make people feel those things explicitly as, as well as implicitly by, by solving the core problem as well.

AI assessment note: “I want them to feel like superheroes.”

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: “it evolved over time and it was highly dependent on the business needs.”

Q shit. So you absolutely can. Um, so I, I totally see that. Can I ask you, you mentioned that the North Star being revenue growth. Do you think that's a good North Star? I don't mean to critique, but like, I always say your North Star should never be revenue. For me, it's about number of videos created per month per user. That, to me, defines the value of Loom.

A It's interesting because for the longest time, our North Star was video views and that core engagement metric, and, um, in the last, call it one to two years, where we updated for the first time our North Star metric to be revenue growth, I think it's actually, among other inputs, um, driven some of the highest velocity best product and Best solving of both customer and business problems. And I think there are a few reasons. I think just being really explicit about the viability of your business, what makes you a great business always comes back to, to revenue at the end of the day, especially as you're in growth stages. And so I think making that abundantly clear and explicit was really, really helpful. And everyone had to tie back, like, even if I'm driving engagement, like, It made us do the extra work of understanding how does driving engagement actually lead to revenue in the long run? It doesn't necessarily need to lead to revenue in the next one to two months. It could refer to how we think about it in, in terms of longterm retention, but I think connecting the dots is something that it forced us to do. I think the second bit in product development, um, that is potentially a mindset shift is if you want to create products, people are willing to pay for, What does that mean? It means you need to do and build something that is so critical to them and solving it so well tha…

AI assessment note: “I think it's actually, among other inputs, driven some of the highest velocity best product”

Q I spoke to so many of kind of our mutual friends, and they said that one of your great skills was writing, and I do just want to dig in on this because I think it's so cool to the role of PM. What are your single biggest piece of advice to PMs on writing and written communication?

A My biggest advice, and this is also very personal to me, is I think writing can be a very powerful tool to clarify your own thinking and thoughts. Um, I think for me the process in and of itself is the forcing function to develop Really, really clear thought and do it at scale so that you don't need to be in every meeting to scale the context or the why or the how, especially in a, a hybrid world. And I think to get to really, really clear writing, I think it requires you and assumes that you understand things so well that you can explain them to other people quickly. And I think I really, really encourage all of our PMs to, to be writing things that requires a ton of detail go there, but what is the one or two pager that everyone can read such that they know the what and the why and the how and know exactly what their job is and can create the, the enough context such that when they're making micro decisions in their everyday, you trust that they have the underlying context.

AI assessment note: “My biggest advice... is I think writing can be a very powerful tool to clarify”

Q In what way, like write PRDs more, write updates for teams more, like what should I write?

A All of the above. I literally, for folks who on my team are trying to get better at writing, I kind of anchor on a few things as really, really tactical tips. I think there's the, the PRD aspect, it's much higher stakes and so requires a ton of revs, which is everything you need to do needs to be a great PRD for someone who is not good at it. You need to get started earlier, get more revs in and get the feedback before it's at a place where people are ready to consume. I think another easier day to day, lower stakes way to get better at writing is taking the mindset of how do I make Every single meeting I have more effective by clear writing. And so from a pre-meeting perspective, it's, Hey, like you should actually send out the goals and the agenda and the like desired outcomes of your meeting to everyone that is attending like a day before the meeting. I think it requires you to clarify your own thoughts of what is the best possible outcome of this? And then, um, do people know what they're expected to do as they get here? As they get to the meeting, I think after meetings is also something that I encourage PMs to be great at, which is after the meeting happened, how do you distill the key takeaways and the summaries simply and the action items? And if you take one look at it, it might feel like a lot of program management, but I think on the other hand, it also feels like fo…

AI assessment note: “All of the above. I literally, for folks who on my team are trying”

Q What do you want to hear there and what do you not want to hear?

A Talking less about the feature that you, you shift or even I think the first Like good, good answer is I ship something that had this impact. I think a great answer tells me, like, this is the problem the company or the product was facing. And like, this is why it was one of the most important things, um, and critical to solve. This is how I went about figuring out that it needed to be solved, how it needed to be solved. Like, this was my role. This was like the process in which I solved it. And this is how, how it landed with customers. And like, most often, If people really, really drove outcomes and like tackled something hard, they're not going to get it right the first time. And so talk to me about like reality versus plan and how you actually forced the, the reality to match up closer to plan. And I think someone who's really owned something end to end understands why they were doing what they were doing and tying it back to the importance, um, is, is really, really critical. And I've seen people do this Exceptionally well, even if they're not working on the most important thing from a top three company priority perspective, right? Like billing folks or a lot of platform products, uh, product managers, um, have to sell the why and the importance of what they do. And I think exceptional ones can talk about how it ties to the business rather than just building for, for scal…

AI assessment note: “Talking less about the feature... a great answer tells me, like, this is the problem”