Janie Lee: Three Core Skills that Make the Best PMs | E1165

1. 0:00 – 0:57

   Intro

   1. JLJanie Lee0:00

      Parker was one of the best product visionaries I've ever had the privilege of working with. He understood the customer like no one could. I think one of the most impactful things you can do is to join companies where there's high talent density, and I think it's probably the single biggest predictor of career acceleration.

   2. HSHarry Stebbings0:20

      Ready to go? Janey, I am so excited for this. I heard so many good things from many different people before, but thank you so much for joining me today.

   3. JLJanie Lee0:41

      Of course, and thanks for having me here. I think feeling is mutual. Some of my favorite people have been on the show, and I think I've learned so much, and so, excited to just get into it today.

   4. HSHarry Stebbings0:50

      Honestly, I think it's a joke that this is even my job, but, uh, no one's caught me yet.

   5. JLJanie Lee0:54

      (laughs)

   6. HSHarry Stebbings0:54

      I wanna start, though, on, like, the love of product.

2. 0:57 – 2:19

   A Journey into Product World

   1. HSHarry Stebbings0:57

      How did you fall in love with product, and when did you realize that actually-

   2. JLJanie Lee1:00

      Oh, yeah.

   3. HSHarry Stebbings1:00

      ... this was the thing you really wanted to devote your career to?

   4. JLJanie Lee1:03

      I think, taking a way step back, I know you're not asking for my life story, but growing up, I think I just had a lot of the- 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 (laughs) 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- 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.

3. 2:19 – 7:09

   Lessons from Opendoor

   1. JLJanie Lee2:19

   2. HSHarry Stebbings2:19

      I mean, listen, there- there's many elements that I wanna unpack-

   3. JLJanie Lee2:21

      Yeah.

   4. HSHarry Stebbings2:21

      ... kind of later on, especially the element of rising. I do wanna just ask, you've worked at some incredible places-

   5. JLJanie Lee2:26

      Mm-hmm.

   6. HSHarry Stebbings2:26

      ... 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?

   7. JLJanie Lee2:39

      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 (laughs) you can do to- to grow your business acumen, and I've since t- since then, I've only worked at SaaS companies. But in- in the world of pricing, accuracy and all the details mattered so much. One mispriced home 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 into 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 PnL of- of a business is the- the type of business acumen that I think serves me especially well in- in SaaS settings, knowing the inputs and- and outputs. I think the other one is just, uh, learning in- in building products how to combine automate- automation with human touch. I think when you're building ML or AI products, you always go with a mindset of, "Everything needs to be automated," or, like, "This needs to scale." And in shipping a lot of these pricing algorithms, you actually realize, like, "Hey, we're directionally there, but if it's fully om- automated today, it's gonna be a really bad experience, either for the customer (laughs) because we haven't nailed it yet, or for the business, because we're gonna ship, uh, an algorithm that misprices a small set of homes." And so, I think really figuring out, like, where is the automation today? Being really, really clear on where it's bad. And, I think figuring out, like, where do you involve manual processes, whether it's, like, human operators or in, like, a product experience today. Like, you don't need AI in everything, right? (laughs) It's- it's starting to build that over time, and I think if you choose the right problems and the core things to solve first versus second versus third. You can still get there, but I think just that mindset of build your way to full automation has- has been hugely beneficial, not just in getting to really good algorithms, but even in how Loom ships AI product today.

   8. HSHarry Stebbings5:12

      My God, I love software businesses (laughs) .

   9. JLJanie Lee5:16

      (laughs) . You'll note that that was the only company (laughs) that I- I- I- I did this in and have joined software businesses since (laughs) .

   10. HSHarry Stebbings5:24

       Uh, very- very smart transition. Uh, uh, the other element that I-

   11. JLJanie Lee5:28

       Yeah.

   12. HSHarry Stebbings5:28

       ... was told I had to ask about was actually your lessons on talent bars from your time at Opendoor.

   13. JLJanie Lee5:33

       I think it's all about talent density and how you think about it when you're junior versus senior. I think when you're more junior in your career, and- and that's where I was when I joined Opendoor, I think one of the most impactful things you can do is to join companies where there's high d- talent density. And I think that's probably the single biggest predictor of- of career acceleration. I think when I interviewed, I remember feeling like...... the dumbest person in the room every interview. And I think more importantly, when I ask people why they were at Opendoor, everyone said they followed the smartest people they knew there. And for, for me that was just so high signal. And I think as you get more senior, it's actually your job to create talent density when you join a, a startup. I think there are components of, can you coach people to get from good to great? Can you actually hire people? I think nothing raises the bar more than bringing in, like, really, really, really great operators. And I think the last one that's hard that we don't like to talk about is also parting ways w- with folks when the coaching or the feedback doesn't work in a, like, really transparent but also empathetic way. And I think, um, that's the biggest mindset shift that, that you need to have as you kind of progress through your career is, like, at the beginning I was just always looking for talent-dense teams. And at some point you realize, oh, I need to create them, and my expectations should not be that talent-dense teams exist at, at a company else they probably wouldn't be hiring me or looking for, for a new leader. And I think that's, um, something that I saw kind of on, on both ends at Opendoor.

4. 7:09 – 11:12

   Lessons from Rippling

   1. JLJanie Lee7:09

   2. HSHarry Stebbings7:09

      What about Rippling? Rippling is a beast of a business today. How, how did that impact your mindset?

   3. JLJanie Lee7:16

      Yeah. I think there are a few things. One is, um, Parker was one of the best product visionaries I've ever had the privilege of, of working with, and I think-

   4. HSHarry Stebbings7:29

      Why, why, why was he so good?

   5. JLJanie Lee7:31

      A few things. One is, he understood the customer like no one could. And you have the CEO of a company actually being our HR administrator at all stages (laughs) of, of the company growth. And you have the CEO literally assigning onboarding tasks to new employees, or administer- administering hardware, and I think he develops customer empathy in a way that is kind of unmatched, um, across most folks I've worked with. And I think when you become the expert on, on the customer problem and you become a customer yourself, you have really, really clear sense of, like, what are the critical problems that we just have to solve and have really opinionated points of views on the solution. And you're probably right way more often than, than the average product person, and so your hit rate is also higher because you know the problems so, so well. I think the other thing I'd, I'd call out is, um, Parker was a great storyteller and salesperson. Um, we, we always talk about the concept of selling ahead, selling the vision, especially as products companies are more nascent in, in their maturity. And whether you talked to, to Parker in 2016 or now, he's probably selling the exact same vision of the world. Um, and in 2016, obviously vision versus reality was much farther apart. But the way in which he could sell a version of the world you didn't know, (laughs) um, existed today is, is also kind of matched by, by none. And I think when you can combine the getting the problems and solutions right so often, great storytelling, and also, um, having, I think, a real competitive mo- uh, taking a somewhat contrarian point of view on do it all versus focus, I think, um, you, you create a really unique opportunity. And, and the opportunity was, is, and, and, um, was theirs to capture and I think they're, they're doing a pretty good job of it so far.

   6. HSHarry Stebbings9:36

      What were your product lessons from Rippling?

   7. JLJanie Lee9:39

      I think two things. One is, how do you create a really, really great customer experience by being integrated everywhere? And I think the second is, um, where and how does end user experience come into play when you're building (laughs) so quickly and, and so many products at the same time?

   8. HSHarry Stebbings9:59

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

   9. JLJanie Lee10:03

      I think it's a, like, very, very iterative cycle. (laughs) 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 gonna be in trouble maybe not now but a year from now when 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 enter- like, an enterprise software-wide lesson, but I think you need to do both even if you separate out the time at, at which you do the two things. But I don't think you can retain customers without, without doing

5. 11:12 – 26:29

   Art vs. Science in Product

   1. JLJanie Lee11:12

      both.

   2. HSHarry Stebbings11:13

      In terms of having an opinion, I'm so glad you said that because I'd love for you to have an opinion on a question-

   3. JLJanie Lee11:19

      Yeah. (laughs)

   4. HSHarry Stebbings11:19

      ... on art versus science. And, and we're not allowed to be in the middle, Janey, okay? So we have to have an opinion, which is very important apparently. So is product more art or science? And if you were to assign numbers to it, which gives you a little bit of leeway, where would you put it?

   5. JLJanie Lee11:35

      I know I'm cheating. Probably 60/40 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 dysfunction on your team, you, you might need a great strategy because the team has no n- 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 in any given situation, I think being right is somewhat of an art to figure out, like, what is the thing needed in, in this situation? I will also say, like, amongst the toolkit, product sense is the, the tool or the skill that feels most art-like, but I feel like there are tons of tactics for developing, um, product intuition and, and taste.

   6. HSHarry Stebbings13:33

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

   7. JLJanie Lee13:40

      (laughs) 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 ab- 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, 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-optimize 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 think the other question I like to ask is, like, what is the extra 5 to 10% that, like, might not fall into scope but could really make this land? And I think those are some of the questions that I like to ask as I'm, you know, reviewing our own product, looking at others. And for PMs who are really, really trying to develop product taste on my team, it, it almost feels pedantic, but I literally say, "Every time you work with your design partner, like, give them at least five pieces of feedback. Here are some of the questions you can answer to try to get to, to good feedback." But I think, um, you know, at some point it becomes muscle memory, but until it does, I think even starting with these helps you think very critically and specifically about things that ultimately, I think develop the, the taste and, and intuition. And so that's the bit that is art but also science-like, because I, I, I do think there's a path there.

   8. HSHarry Stebbings16:04

      I, I've got, I've got notes, okay? So I'm taking notes. So when you-

   9. JLJanie Lee16:07

      (laughs) I gotta send you a notebook, Harry. (laughs)

   10. HSHarry Stebbings16:09

       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? Jamie, is simple always better in product?

   11. JLJanie Lee16:20

       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, you know, in a given experience, what are the, the first level of actions you may wanna 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 b- 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 w- easy to use ones often win.

   12. HSHarry Stebbings17:20

       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?

   13. JLJanie Lee17:30

       I want them to feel like superheroes. It sounds (laughs) 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 they're 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, uh...... 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 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 pe- people feel those things explicitly as- as well as implicitly by- by solving the core problem as well.

   14. HSHarry Stebbings18:49

       You said about being opinionated. I think there's one part of Pro- 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 wanna 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.

   15. JLJanie Lee19:09

       Yeah. It's a great question. I'd say it evolved over time and it was highly dependent on the business scenes. I think very, very early in, um, Loom'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 (laughs) . 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- that we placed in our pricing and packaging principles were really important. I think recognizing that, yes, we need to optimize for revenue, but also we probably have 1% market penetration of this behavior, and so we still need to really grow flywheel, willingness to dr- to- to- to try recording video was really high. And so a core principle was like, don't block people from recording or viewing, like always give them an out. And so even with driving new pricing and packaging limits at a- at a 25 limit, we made sure that everyone had an out, which is, one, you could invite people to- to get a higher limit or you could actually just delete videos. And is it zero friction? No, but is it still (laughs) ...

   16. HSHarry Stebbings21:25

       I- I- I'd delete videos. Yeah, it's really easy.

   17. JLJanie Lee21:27

       Yeah.

   18. HSHarry Stebbings21:27

       I actually... I hate it. I- I look back and I go like, "Oh, christ, you were young. Get rid of that shit."

   19. JLJanie Lee21:31

       (laughs)

   20. HSHarry Stebbings21:31

       Uh, so- so you absolutely can. Um, so I- I totally see that. Can I ask you, you mentioned there 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.

   21. JLJanie Lee21:52

       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- 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 long-term 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 need- it means (laughs) you need to do and build something that is so critical to them and solving it so well that they're actually giving you the benefit of- of their dollars n- n- their wallet. And I think, you know, in the worst case outcome of building or optimizing for revenue growth you're doing short term things that are incredibly bad for your product, forgetting about core engagement and especially for a- a PLG company like Loom. I think in the best case it gives everyone a really, really clear mandate to make sure that they know exactly how they're doing, what they're doing is- is tying to revenue and, um, raising the bar for the- the quality of products, and fortunately that's the- the area I think we landed.

   22. HSHarry Stebbings23:53

       Okay. Right. Couple of quick fires.

   23. JLJanie Lee23:55

       Yeah.

   24. HSHarry Stebbings23:55

       Do you think you're opinionated enough if you give people the chance to delete, to invite? Like, I don't pay for Loom, I love it, but I just delete videos. Like, should you not be more opinionated?

   25. JLJanie Lee24:06

       I think we can. I think there's a world where we might get there. But I think where we're at today is we really value our power users. Power users have an outsized impact on our ecosystem, both in their reach...... the number of viewers they're, they're getting. And I think the, the second is, no matter what you do, there are some customers who are never going to, to pay for your product. The- and I think that's okay. And so there's a question to, to be had of, like, how large do you want that group to be, and, like, what is the value of letting them continue to be on the ecosystem? And I think-

   26. HSHarry Stebbings24:41

       Do you even want them?

   27. JLJanie Lee24:42

       I think right now, like, Harry, I want you on our ecosystem. You, I'm hoping, are sending Looms that have broad reach to customers. I think the value of you posting a, a Loom on your Twitter feed or any of your channels actually gives us way more in top-of-funnel awareness than the cost of, of, you know, storing your 25 videos, um, in, in our infrastructure. And so I think, definitively, yes. And I think the question is, like, how large and- or little do we want that group to be? That probably changes over time. But in, in our current world, we... Harry, please stop. Uh, please don't stop using Loom (laughs) and we'll also see how we can get you a, a paid plan.

   28. HSHarry Stebbings25:23

       Do you know what I d- use it for primarily? And this sounds awful. I use it for turning down founders 'cause I find emails very impersonal. And so when you say, "Janey, I love Meeting. I found these were my three core struggles that I couldn't get over actually," and it's a much more human, nice way to actually make a hard decision and, uh, you know, potentially let someone down. It- but it's more contextual than email, and so I find it incredible for that.

   29. JLJanie Lee25:50

       I love that. Um, yeah, I think the human nature and the empathy is massive. We also love using it for the opposite use case, which is when we send out offers to folks, we have everyone on the hiring panel record a Loom, and we send them a doc that has 10, 15 embedded Looms, um, in, in the doc. And I remember on- being on the receiving end and feeling absolutely floored. It's one of those soft things that, you know, sometimes actually help you tip the scale to, to choosing an offer that might not be as competitive from a financial perspective, but give you a real reason to, to join.

6. 26:29 – 32:58

   From Consumer Product to Enterprise Solution

   1. JLJanie Lee26:29

   2. HSHarry Stebbings26:29

      Okay. Hard question. Loom is a PLG product that has, like, a consumer adoption slant. Loom wanted to go into enterprise. Loom, I'm sure, wants to go into enterprise. It is a different product game. It is really hard to make that product transition. You suddenly have a different buy. You have the problem of agency. For you, as the product leader, just talk to me about how you face that product challenge of building a, a consumer product. "Oh, shit. No, wait, we need to do an enterprise product."

   3. JLJanie Lee26:56

      I think there are a few things. I think, one, we have the, the big elephant in the room of I think we're in a, a pretty competitive spot in that we've been acquired by Atlassian. And so I think that's one. I think s- um, point number two is you just have to fundamentally change the DNA and makeup of your team, both in how you hire, but also how you operate. Like, a enterprise PM and a enterprise team is not going to be seeing the immediate quarterly results or impact to the business that a core product or growth team is. And so how do you fundamentally change how they operate, what gets celebrated? And you need to, to create the space for that.

   4. HSHarry Stebbings27:35

      How do you change that? Like, wha- what changes?

   5. JLJanie Lee27:38

      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 un-sexy to the average core product person, things like data residency, or HIPAA, or, or FINRA compliance that, um, you're not actually gonna see immediate dollars to, even if you spend six to 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?

   6. HSHarry Stebbings28:26

      Mm-hmm.

   7. JLJanie Lee28:26

      It's, "Hey, by, by actually building out data residency, this is how much more opportunity or how much more of our 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 wanna 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 (laughs) and you share those outcomes with the team that owns it, because as you move into sales-led enterprise, I could build the best product in the world, and it might not result in revenue. And so I think, like, even my own success (laughs) and ab- and a- and, I think, ability to succeed and drive impact as a product person completely changes. And so that's kind of a, a big thing.

   8. HSHarry Stebbings29:23

      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 gonna move into enterprise, uh, 'cause 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?

   9. JLJanie Lee29:41

      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- uh, 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, uh, company productivity. And obviously, we were excited that, you know, 10, 15,000, 20,000 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 (laughs) . 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 to learn, especially from a go-to-market perspective, like, what to, to build, how to sell, how to create resonant messaging. Um, and then I'd say on the other hand and things that kind- we're kind of learning as we integrate with Atlassian is, um, you're either in or you're not (laughs) at some point in, in building for enterprise. I think, um, the jump to go from PLG to enterprise is, is a pretty big one at some point, and you could progressively get there, you know, over the course of years. But at some point when you're talking with multiple big customers, they kind of need it all when it comes to the enterprise requirements. And what I mean by they kind of need it all is a lot of large customers may not need data residency, but they need XYZ. A different customer may not need XYZ, but they different- they need a different permutation. And I think it becomes really, really, uh, painful (laughs) for product teams to constantly figure out what is the next thing that we have to build to unlock this much more revenue? And instead, I think having the top-down commitment that, like, "Hey, we want to, to win at enterprise. We're not gonna iteratively get our way there over the course of four years." And at some point, I think the switch needs to turn on where as you're seeing more demand from these customers, you need to make a real commitment, both from a staffing perspective and, uh, uh, on R&D as well as go-to-market that you're really gonna, gonna win and, and go all in. I think at some point after a certain amount of demand, you just need to, to get there and change the way you fundamentally operate.

7. 32:58 – 34:18

   Roadmap vs. Revenue

   1. JLJanie Lee32:58

   2. HSHarry Stebbings32:58

      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 10 million in ARR from two or three large customers. When do you say, "Yes, we will deviate," versus "No, we won't"?

   3. JLJanie Lee33:20

      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 n- needs to figure out at what point (laughs) are they, 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.

8. 34:18 – 43:19

   What Makes a Truly Great PM

   1. JLJanie Lee34:18

   2. HSHarry Stebbings34:18

      I spoke to so many of, uh, kind of our mutual friends, and they said that one of your great skills was writing. And I do just wanna 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?

   3. JLJanie Lee34:33

      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, uh, 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, uh, enough context such that when they're making micro decisions in their everyday, you trust that they have the underlying context?

   4. HSHarry Stebbings35:40

      So I'm a PM, and I'm not great at writing, and I don't love writing. What would you advise me to get better at writing?

   5. JLJanie Lee35:46

      From a actual tactics perspective, I think it's, it's not gonna be fun, but it's to write more (laughs) .

   6. HSHarry Stebbings35:53

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

   7. JLJanie Lee35:59

      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 (laughs) 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 forcing great writing, which is distill the things that matter most, make sure people know what they are, and make sure they're communicated in a way that lands. And I think even the process of forcing people to think about something (laughs) before, like, said event, forcing people to take said event or learnings, distill it down again, is just building that muscle of, like, distill, distill, distill, and repeat, repeat, repeat. Very, very specific tactic, but I think it's a lower stakes way to just force yourself to- to get better.

   8. HSHarry Stebbings37:57

      Uh, the more specific, the better. So never ever worry about that.

   9. JLJanie Lee38:00

      Yeah.

   10. HSHarry Stebbings38:00

       Can I ask you, what are the biggest mistakes that you see PMs make when it comes to writing?

   11. JLJanie Lee38:03

       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 doc, or a PRD, be on page eight, and still ask yourself, "I don't know what I'm reading." (laughs) There are a lot of details here. There are a lot of edge cases or requirements. But I- I- it... But I still don't know what, why, and- 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 wanna take five more reps at- at simplifying is- is the biggest one. I think the- 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 gonna take this and turn it into- to lines of code. And the level of- of context they need is very different. But also the- the language and the whys is- is very, very different. And so, I'd call out those two as the- the things that I see most often.

   12. HSHarry Stebbings39:14

       Totally agree with you there in terms of, like, the ICP of the content. I say with every piece of content-

   13. JLJanie Lee39:19

       Yeah.

   14. HSHarry Stebbings39:19

       ... that we do, like, who's the buyer?

   15. JLJanie Lee39:20

       Totally.

   16. HSHarry Stebbings39:21

       Um, and that's really important, 'cause it also changes the positioning of every single question you ask. Uh, why do I ask there about, like, what are the mistakes? 'Cause I'm putting my hat on of, like, I'm an aspiring PM-

   17. JLJanie Lee39:31

       Yeah.

   18. HSHarry Stebbings39:31

       ... or I'm a product leader measuring the skills of a PM. So, totally agree with you there. Another... And I'm- I'm... I had so many, like, where they said, "Janey's great at this."

   19. JLJanie Lee39:40

       Yeah.

   20. HSHarry Stebbings39:40

       "And I wanted to unpack it." Apparently, you're amazing at question asking-

   21. JLJanie Lee39:44

       Mm-hmm.

   22. HSHarry Stebbings39:44

       ... 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?

   23. JLJanie Lee39:52

       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- 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 gonna keep digging in. If it's not consequential, I don't wanna create more work for my team. And so, I might still ask the question, but, like, how deep do I go is really, really dependent on, like, what is the risk of getting this wrong? And then, I think the- the last thing that I ask for myself is like, is there any context that I uniquely have that this team needs, or, like, an area where I sh- need to be connecting dots? Um, and so, that... Like, answering that question for myself not- might not result in a question, but I think, like, my job in a lot of meetings, if I'm speaking, is, like, ask the right questions that are most important or, like, share the context that people need so that they have a- a more foundational North Star or why of what they're doing, or even know where and who they need to be talking to. If I'm able to answer these questions for myself, I'm pretty silent. I don't want to- to dominate the conversation. And if I can't, um, I think it's critical that I ask these questions so that we don't, you know, a month before launch, realize, like, all of these things aren't- aren't in place.

   24. HSHarry Stebbings42:17

       I- I have two lessons for me, which is, like, you have two to five minutes at the beginning of every meeting where you have the chance to set the tone of, like, vulnerability and openness. Like, uh, vulnerability generally breeds vulnerability. "Actually, I- I'm struggling with X right now, Janey. I'd love to hear how you think about it."

   25. JLJanie Lee42:32

       Yeah.

   26. HSHarry Stebbings42:32

       When you ask for advice from someone, it engenders a feeling that they're sharing and giving, and it makes them much more willing to open up in the future conversation. So, I always do that in the first two to five minutes.

   27. JLJanie Lee42:41

       Yeah.

   28. HSHarry Stebbings42:42

       And then, I would also say the biggest mistake people make is they're not comfortable in silence. Sometimes you have to ask a question and let it sit.... and not continue, and like the magic will happen in the silence.

   29. JLJanie Lee42:55

       (laughs)

   30. HSHarry Stebbings42:55

       Um, and I find too many people aren't comfortable in silence when asking questions, two big things for me.
9. 43:19 – 54:23

   How to Structure Hiring Process

   1. HSHarry Stebbings43:19

      a product team. How do you advise me, an early stage company, on how to structure my hiring process for product team and product people?

   2. JLJanie Lee43:29

      Yeah. I'd say, um, twofold, and it really depends on are you trying to hire someone more senior or more specialized or not?

   3. HSHarry Stebbings43:37

      You tell me. We're at a million in ARR. We've got some customers, but I'm not, not that f- late and I'm not that early.

   4. JLJanie Lee43:45

      I personally am a huge fan of, of junior PMs. Um, I think we all know the rockstar PMs who are really earlier in their career, and I think they have a few key traits that I look for. I think one is just, like, incredibly high horsepower, both on the IQ and EQ front. I think the, the second is effort. Hungry people who are going to work hard naturally just have a much steeper slope because they're (laughs) simply doing more in the same amount of time and getting all those reps in. And I, I think the last one is, are they coachable? Do they have the humility to know that they still have a ton to learn and are, are able to adapt? And I think, um, a lot of times, like, junior folks are oftentimes the cheapest but also, like, from a pure salary perspective, but also can be a huge force multiplier and just a large arbitrage opportunity. And I think if you, especially in earlier days, can hire for these, like, generalists who have these three traits, you can really train them to, to be effective PMs very quickly. I think it doesn't get you all the way there, but again, I think for, for earlier stage, like if you have someone who can spend the time with, with junior folks, I'm, I'm a huge fan.

   5. HSHarry Stebbings44:59

      What are the questions that we ask in every interview? What are the must-ask questions for product hires?

   6. JLJanie Lee45:04

      It depends on the stage. I think in those initial f- parts of the, the top of funnel, I'm trying to get a, a really good sense of, like, what is your track record of impact? Like, how introspective are you, and, like, is there alignment on the opportunity? And then, I think as you get... And happy to go into any specific questions I ask there. And then, I think as you get closer to deciding if you want to hire a candidate, look for much higher signal on the ability to, like, tackle the problems that we're, we're tackling.

   7. HSHarry Stebbings45:37

      On the track record of impact, like, unpack that for me. What questions do we ask?

   8. JLJanie Lee45:41

      I think one is super straightforward, which is, like, "What is your background and what's your biggest professional accomplishment and why?" And I dig way, way deep into how or what they did and why they consider that to, to be their professional o- biggest accom- accomplishment.

   9. HSHarry Stebbings45:59

      Yeah. What do you wanna hear there, and what do you not want to hear?

   10. JLJanie Lee46:02

       Talking less about the feature that you s- you shipped, or even, I think, the first, like, good l- good answer is, "I shipped something that had this impact." I think a great answer tells me, like, "This is the problem the company or the product (laughs) 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 gonna get it right the first time. And so, talk to me about, like, (laughs) 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 (laughs) 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 scale and things like infra. And so, I love to dig deep. I can talk to a, a candidate for 20, 30 minutes just on this question alone and leave feeling pretty confident on whether or not I wanna keep having the conversation.

   11. HSHarry Stebbings47:43

       What percent of them impress you?

   12. JLJanie Lee47:45

       It depends on if I have proactive outreach or inbounds. (laughs) I think proactive outreach because I'm almost doing the back channeling upfront, probably like 50, 75%. Inbounds, much, much lower, um, just because there's really only one filter that's happening through my, my recruiting partner.

   13. HSHarry Stebbings48:04

       Okay. So we're testing for harder skills. What do we need to test for harder skills, and do we do case studies? Do we do any material tests?

   14. JLJanie Lee48:12

       Love, I know it's controversial, a take-home (laughs) , um, and particularly before the, the super day. And I use this, the take-home to, one, assess should they come and meet the whole team, very expensive (laughs) use of team time and their time, and then two, if they'd come to the team to start to test out, um, how they actually work with people. Are they actually able to, to interact with critical questions? C- do you come off as defensive or curious when, when probed? And so, taking a, a step back, take-home, usually a very, very ambiguous problem that we like to give folks that are tied to the work they're gonna do.

   15. HSHarry Stebbings48:50

       So you give them a Loom problem specifically?

   16. JLJanie Lee48:52

       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 in, in 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. (laughs) 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 have 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, and grateful for that, but I think if there's a job you absolutely want, you're gonna put in the, the effort and preparation. And I actually wanted to see that and what that looks like because I think it almost translates to, how are they gonna be in their first 30 days? Are they gonna spend their first 30 days meeting people, having one-on-ones? Or are they gonna spend their first 30 days (laughs) like absorbing context but also getting really, really, really deep in their understanding and, and actually come out of that 30 days with a point of view?

   17. HSHarry Stebbings50:49

       What percent of people do you put in the process of taking a day of the team's time, doing the test, and then they don't get it?

   18. JLJanie Lee50:56

       Yeah, uh, so you're asking how many people make it from take-home to super day or super day to offer?

   19. HSHarry Stebbings51:02

       Sorry, what is super day?

   20. JLJanie Lee51:04

       Super day is when they're meeting everyone on the team and really that final round-

   21. HSHarry Stebbings51:07

       Okay, so, so basically we, we have first interview and, like-

   22. JLJanie Lee51:11

       Yeah.

   23. HSHarry Stebbings51:11

       ... hey, you're good enough. And then we do the take-home.

   24. JLJanie Lee51:14

       Yep.

   25. HSHarry Stebbings51:15

       And then the super day.

   26. JLJanie Lee51:16

       Yeah.

   27. HSHarry Stebbings51:16

       What is the progression rate between each?

   28. JLJanie Lee51:19

       Again, I think it depends on type of candidate. If it's a really strategic outbound, pretty high, um, and then if it is inbound, I'd say most of the drop-off happens between before it even gets to me, which is my recruiter will parse out all the resumes. By the time it gets to me, I'd say, um, between initial conversation to take-home, probably like 25%.

   29. HSHarry Stebbings51:44

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

   30. JLJanie Lee51:48

       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 wanna learn more. Let's use the time to uplevel, like, craft and quality of decisions." And I think the candidates' 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, a random case study. You've already taken the time to think through this, and so I think it also solves for the fact that, like, not everyone is good at a random case study on the spot. Like, how do you do when you've thought about something, put in the time, and are then being asked to really grapple with, with hard questions?
10. 54:23 – 1:00:29

    How to Do Product Reviews

    1. JLJanie Lee54:23

    2. HSHarry Stebbings54:23

       Final one before we do a quick fire. It's just that product reviews are a core 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.

    3. JLJanie Lee54:34

       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 gonna be really bad. Um, and so for these reviews, uh...... I or 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 exec reviews, based on the, the product lifecycle. 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. (laughs) 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 lifecycle, we start to get into solutions, and we have exec reviews on, on the solutions. Um, want the product teams to come to the table with a few options, but be really, really opinionated on 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 that this is gonna land with customers and starts to bring in go-to-market, and, um, really talk about how we'll, we'll deliver this product? And we've evolved this process a ton. I think the, the few things that really have made this effective are the, the rituals we have, like before, after, and, and during the review itself.

    4. HSHarry Stebbings56:24

       What are those rituals?

    5. JLJanie Lee56:25

       Yeah. Before a exec review, the, the product leader or the PM will send out a Loom pre-watch 24 hours ahead of the review, and the expectation is that before people come to this review, that everyone's watched the review, they've all dropped in feedback and questions already. And I think most important, the feedback that is inputted into the, this artifact is prioritized in a self-categorization way. And so, I think one of my favorite sayings from someone I worked with at Opendoor is, "Questions are cheap, answers are expensive, and the exec review should not try to get through all questions."

    6. HSHarry Stebbings57:06

       Uh, what does, "Questions are cheap, answers are expensive," mean in product?

    7. JLJanie Lee57:10

       Look, for anything that you're shipping, we can ask any question that we want (laughs) 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.

    8. HSHarry Stebbings58:03

       It's, it's interesting. One of my great friends is Gustav Soderstrom. He's the CPO at Spotify, and he said that, "Talk is cheap, and so we should do more of it."

    9. JLJanie Lee58:12

       (laughs)

    10. HSHarry Stebbings58:14

        And I, I dis-

    11. JLJanie Lee58:15

        I agree.

    12. HSHarry Stebbings58:15

        I, I disagree with him thoroughly.

    13. JLJanie Lee58:17

        Yeah. (laughs)

    14. HSHarry Stebbings58:17

        I think he's complete y- but he's, but he's the CPO of Spotify, and he's much smarter and richer than me.

    15. JLJanie Lee58:22

        Yeah.

    16. HSHarry Stebbings58:22

        And so clearly, I maybe missed something. How do you feel when you hear that?

    17. JLJanie Lee58:27

        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. (laughs) 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, uh, 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 (laughs) 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, 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 t- (laughs) and, and the, the meeting itself, the full 45 minutes to an hour, is spent on just the P zeros. 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 h- 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 that, combined with, after these reviews, making sure that product folks are closing the loop to, to share and scale context is the other important bit. We don't always make decisions that everyone loves coming out of these exec reviews, but it's really, really important for people to talk about what the decision was, why it was made, what are the known risks or cons to making this, and, like, why we made them anyway.

    18. HSHarry Stebbings1:00:25

        (laughs)

    19. JLJanie Lee1:00:25

        And that's the only way you get to disagree and commit.

11. 1:00:29 – 1:06:39

    Quick-Fire Round

    1. JLJanie Lee1:00:29

    2. HSHarry Stebbings1:00:29

       I do wanna do a quick-fire. So I'm gonna pepper you with some questions.

    3. JLJanie Lee1:00:32

       Okay.

    4. HSHarry Stebbings1:00:32

       And then you hit me with-

    5. NANarrator1:00:33

       (laughs) Oh, God.

    6. HSHarry Stebbings1:00:33

       ... 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?

    7. JLJanie Lee1:00:41

       I think it's storytelling at scale. I think-

    8. HSHarry Stebbings1:00:46

       Mm-hmm.

    9. JLJanie Lee1:00:46

       ... 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 (laughs) and, and team growth. And so, I think this is something that...... I'm just always working on, which is, this moment in time (laughs) 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?

    10. HSHarry Stebbings1:01:46

        How does AI change your role as a product leader?

    11. JLJanie Lee1:01:49

        One is the speed at which we develop. It is just crazy how fast the future has- has come. And so, things that we thought we'd be shipping in five years, we're shipping in six months or a year.

    12. HSHarry Stebbings1:02:03

        What's that down to? Is that because of CoPilot? Is that because of... W- why is that?

    13. JLJanie Lee1:02:07

        Yeah. I think a lot of these, especially in the video space, the- the models are getting really good and getting better quickly. And so, we- we are constantly building with the assumption that the basic (laughs) automation or AI we have today is gonna be 100 times better, and how do you build an experience that just gets better over time? And- and be high conviction and- and just build for that, and trust that- that- that technology is gonna come not in a year, but in three months. So, we actually need to start building for it, even if it hasn't arrived yet. And so, I think that's one. We've pulled up a lot of big bets that we may have taken in- in a few years, but we can take now. I think the second one is, in a way, it- it hasn't changed th- the way we build in a lot of ways, just because... I think AI is- is a tool and it's not the end, and I think that's something that, uh, a lot of folks do get wrong, is like, "How do I build AI?" is the question people are- are... A-I products that people are- are trying to ask. And I think the- the question should actually be like, "How do I use AI to solve the customer problems I know about, like, better or faster?" And so, I think it- it also doesn't change the way in which we- we build, and it's important that it doesn't.

    14. HSHarry Stebbings1:03:22

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

    15. JLJanie Lee1:03:28

        I recently went to Kindbody. It's a women's healthcare provider in- in the US. 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 (laughs) difficult industry to move. And I think after working in- in real estate (laughs) , 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- into Kindbody, walls are a 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 (laughs) 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 (laughs) . 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 (laughs) . 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 roughly the same, but they've nailed the user experience, which is ease of use and delightful. It's... They also spend their time focusing on being interpretable- interpretable. And so, when I see a lab, uh, test and all the results, I don't usually know what most of the things mean, and- and they tell me (laughs) . And I think the exciting bit is it's better than anything I've experienced, but yet, as a product person, I'm like, "There's still so much room (laughs) to- to grow this thing." And I think it gives me a glimpse of hope and excitement for this industry that's, like, extremely (laughs) antiquated, and progressively, it feels like it- it- it's getting worse. And so, um, might not be the most innovative, groundbreaking thing, but you- you mix all of these things together and it's still the best experience I've had (laughs) .

    16. HSHarry Stebbings1:05:48

        Final one, what do you know now that you wish you'd known when you started in product?

    17. JLJanie Lee1:05:52

        I think when I started in product, I underestimated the importance of go-to-market and storytelling when it comes to actually landing a product really well (laughs) externally and with customers. I think you oftentimes think, "If I solve the right problem, build it really well, the users will come." And like, yes, sometimes it does, but when you add incredible go-to-market brand storytelling, the compounding effect, I think, is something that I- I didn't fully appreciate until- till later in my career.

    18. HSHarry Stebbings1:06:25

        Janey, listen, I- I've gone completely off schedule for most of it, but I love a natural conversation.

    19. JLJanie Lee1:06:29

        Yeah.

    20. HSHarry Stebbings1:06:29

        So, thank you so much for moving with the very flexing schedule, and you've been fantastic.

    21. JLJanie Lee1:06:35

        Awesome. Thanks, Harry, for having me. This was-

    22. HSHarry Stebbings1:06:37

        ... anything.

    23. JLJanie Lee1:06:37

        ... this was an incredible chat.

Episode duration: 1:06:39