20Product: Loom CPO Janie Lee on Three Core Skills that Make the Best PMs, How to Find, Pick and Train the Best PM Talent and Lessons from OpenDoor and Rippling on Product Breadth, Pricing and Talent Density

Parker
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. This is 20 product with me, Harry Stebbings. Now this is the monthly show where we sit down with the best product leaders.

Harry Stebbings
And today we're joined by the product. Leader of a product that I love. And use every day. Loom. Essentially, Loom allows you to record videos and add them to emails and share them with people super easily.

I find it provides so much context to an email and I love it for hiring. Saying yes or no to a company, as tough as it can be to say no to a company, I find it provides so much tone and context and then for Janie. Janie is the head of product and. The owner of the self serve business at Loom. Previously, Janie worked at Rippling, leading the identity management and hardware teams.

And before that, Janie worked at Opendoor. During her time at Opendoor, Opendoor scaled from two to 20 markets and to $5 billion in revenue with 1500 employees. But before we dive into the show today, we're all trying to grow our businesses here. So let's be real for a second. We all know that your website shouldn't be this static asset.

Janie
It should be a dynamic part of your strategy that really drives conversions. That's marketing 101. But here's a number for you. 54% of leaders say web updates take too long. That's over half of you listening right now.

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Harry Stebbings
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Give it a try and visit Pendo IO 20 product podcast to learn how your team can use Pendo to start building better digital experiences. There, you can also check out Pendo's lineup of free certification courses, 12 hours of in depth training for your product management teams on topics from AI to product analytics to product led growth. To check it out, simply head over to Pendo IO 20 product podcast. That's 20 product podcast. You have now arrived at your destination.

Janie
Janie, 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. Of course, and thanks for having me here. I think feeling as mutual, some of my favorite people have been on the show and I think have learned so much and so excited to just get into it today. Honestly, I think it's a joke that this is even my job, but no one's caught me yet.

I want to start, though, on like the love of product. How did you fall in love with product and when did you realize that actually this was the thing you really wanted to devote your career to growing up? I think I just had a lot of the innate qualities of a PM. I think on one end I was just like a weird kid growing up that loved leadership. I was the type, type of middle schooler or high schooler who went to leadership camp.

Parker
I actually worked on a statewide nonprofit trying to lead teams of teenagers and I think if you can lead a group of hormonal teenagers, you're a pretty good track for the real world. I was also a humanities and very much a multidisciplinary background person. I studied public policy, african american studies, and so everything I did in college was writing and clarity to thought I might have taken maybe to multiple choice exams, but I was pretty much writing straight every day. 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 any one of them. And knew immediately that this was like the kind of dynamic job that I wanted.

Janie
I mean, listen, there's many elements that I want to unpick 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 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?

Parker
From Opendoor, 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 grow your business acumen. And I've since since then have only worked at SaaS companies. But in the world of pricing accuracy and all the details mattered so much, one mispriced home could wipe out the profit of 20 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 with our pricing algorithms, we had to understand things like outliers. And that required us to go deep and do case studies on every time we got it wrong. And on the flip side, celebrate when we share to 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 type of business acumen that I think serves me especially well in SaaS settings. Knowing the inputs and outputs in such detail, I think the other one is just learning and building products how to combine 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 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 automated today, it's going to be a really bad experience either for the customer because we haven't nailed it yet, or for the business because we're going to ship 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 and everything, right? 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 been hugely beneficial.

Not just in getting to really good algorithms, but even in how loom ships AI product today. My God, I love software businesses. You'll note that that was the only company that I did this in and have joined software businesses since. Very smart transition. The other element that I was told I had to ask about was actually your lessons on talent bars from your time at Opendoor.

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 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 talent density, and I think it's probably the single biggest predictor 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 asked people why they were at Opendoor, everyone said they followed the smartest people they knew there. 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 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 with folks when the coaching or the feedback doesn't work in a really transparent but also empathetic way. And I think that's the biggest mindset shift 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 a company, else they probably wouldn't be hiring me or looking for a new leader. And I think that that's something that I saw kind of on both ends at Opendoor.

Janie
What about rippling? Rippling is a beast of a business today. How did that impact your mindset? A few things. Parker was one of the best product visionaries I've ever had the privilege of working with.

Why was he so good? He understood the customer like no one could. You have the CEO of a company actually being our HR administrator at all stages of the company growth, and you have the CEO literally assigning onboarding tasks to new employees or administering hardware. And I think he develops customer empathy in a way that is unmatched across most folks I've worked with. And I think when you become the expert 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.

Parker
And you're probably right way more often than the average product person. And so your hit rate is also higher because, you know, the problems face so well. I think the other thing I'd call out is Parker was a great storyteller and salesperson. We always talk about the concept of selling ahead, selling the vision, especially as products companies are more nascent in their maturity. And whether you talked to Parker in 2016 or now, he's probably selling the exact same vision of the world.

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 existed today is also kind of matched by none. And I think when you can combine getting the problems and solutions right so often, great storytelling, and also having, I think, a real competitive moat of taking a somewhat contrarian point of view on do it all versus focus. You, you create a really unique opportunity, and the opportunity is, and was theirs to capture. And I think they're, they're doing a pretty good job of it so far.

Janie
What were your product lessons from rippling? One is how do you create a really, really great customer experience experience by being integrated everywhere. And I think the second is where and how does end user experience come into play when you're building so quickly and so many products at the same time? Where did that lead you in terms of the end user experience when you're. Building so much, so fast, very, very iterative cycle?

Parker
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 the actual users, the admins, aren't using the product, you're going to be in trouble, maybe not now, but a year from now when people 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 an enterprise software wide lesson. But I think you need to do both, even if you separate out the time at which you do the two things.

But I don't think you can retain. Customers without doing both 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 on art versus science. And we're not allowed to be in the middle, Janie, so we have to have an opinion. So is product more art or science?

Janie
If you were to assign numbers to it, where would you put it? Probably 60 40 more art than science. There is an art in diagnosis and science in how to execute. And 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? The science aspect of pulling on your toolkit is interesting because early in your career you don't have a ton of tools in your toolkit.

Parker
Most PM's are typically really great at one thing, something like execution or something like writing a doc. And people expand their toolkit over time, mostly by just getting the reps in of building and being in different circumstances. But the ability to diagnose, like what situation am I in? What do I need to do to solve it is art because 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 might need a great strategy because the team has 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.

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 this situation. I will also say like amongst the toolkit, product sense is the tool or the skill that feels most art like. But I feel like there are tons of tactics for developing product intuition and taste. What are those tactics for developing product intuition and taste? As someone who's frequently told I have.

Little taste, yeah, I think there are a few things throughout the product process. I think when folks are crafting the strategy or just understanding a product, I think it's asking yourself, can I crisply articulate the customer problem and why this has to be solved? And you can ask a ton of PM's, 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 being able to articulate how you would talk about this in the market.

That gives you a really good foundation of why you're building something. What is the value for customers, and how do I actually sell it? 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? 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? How does this experience actually make me feel? Can or does this actually make sense? Across the global product experience 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 their solution. And then I think the other question I like to ask is, like, what is the extra five to 10% that, like, might not fall into scope, but could really make this land? And 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 PM's who are really, really trying to develop product taste on my team, 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 good feedback, but I think 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 taste and intuition. And so that's the bit that is art, but also science like, because I do think there's a path there. So 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? Generally?

Yes, I do really, really believe in progressive disclosure in product experiences. 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 first level of actions you may want to take, and only expose more if you really, really show interest in wanting to take that. And this is a core product principle of loom is it just has to be simple, fast and easy for a product to be loved and adopted. I think there are obviously nuances and edge cases where the complexity is required, but I'd say for most products, on average, the simple, easy to use ones often win.

Janie
How do you want to make users feel? You said there about how you make them feel. How do you want users to feel? As a product creator and as a. Pm, I want them to feel like superheroes.

Parker
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, humans, as a result of using the product. You can do that, I think, both by choosing the right problems to solve. But the other bit is like how you celebrate 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 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 specifically how much time you saved, or the fact that you just actually reached way more people than you would have had you gone with another way of communicating. I think it's also our job to make people feel those things explicitly, as well as implicitly by solving the core problems. Well, you said about being opinionated. I think there's one part of Proloom'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.

Janie
That is quite an opinionated kind of paywall. How did you think about that? I'm just interested. Yeah, it's a great question. Goal number one is create a new market behavior and get as many people there as quickly as possible.

Parker
And then I think context also is 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 had a much higher limit that was actually never enforced. And so we really let people use our paid product 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, figured out what are the right limits to achieve the balance of goals that we need in this new phase of revenue growth. Being kind of 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. 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 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 25 limit, we made sure that everyone had an out, which is one, you could invite people to get a higher limit, or you could actually just delete videos. And is it zero friction? No.

Janie
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. Should you not be more opinionated? 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 getting.

Parker
The second is, no matter what you do, there are some customers who are never going to pay for your product. That's okay. And so there's a question 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? Do you even want them?

I think right now, like, Harry, I want you on our ecosystem. I'm hoping, or sending looms that have broad reach to customers. I think the value of you posting 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 storing your 25 videos 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 our current world, we. Harry, please don't stop using loom. Yeah, I think the human nature and the empathy is massive. When we send out offers to folks, we have everyone on the hiring panel record a loom and we send them a dock that has 1015 embedded looms in the dock. And I remember 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 choosing an offer that might not be as competitive from a financial perspective, but give you a real reason to join. Hard question. Loom is a PLG product. There's like a consumer adoption slant. Loom wanted to go into enterprise.

Janie
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 consumer product. Oh, shit. No, wait. We need to do an enterprise product. We have the big elephant in the room.

Parker
I think we're in a pretty competitive spot in that we've been acquired by Atlassian, and so I think that's one 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. A enterprise. PM and 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 create the space for that. How do you change that? Like, what changes? 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. There are a few components to enterprise. There are just some table stakes, things that are maybe unsexy to the average core product person, things like data residency or HIPAA or FINRA compliance that you're not actually going to see immediate dollars to, 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 actually building out data residency, this is how much more opportunity or how much more of our customer base we've unlocked. And the next quarter, the results that we celebrate may not be purely owned by product teams. 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 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 even my own success and ability to succeed and drive impact as a product person completely changes. And so that's kind of a big thing.

Janie
So I'm an angel investment of yours. We've got a great PLG product and I'm the CPO or the CEO, and we're going to move into enterprise because that's where we're being told we need to go. What advice would you give to me knowing all that you know now, having made and being in that transition? Two things. One method is working your way up to enterprise.

Parker
And then I think the second is like, like if you are seeing enterprise demand kind of at the larger scale, what do you do? I think the first mistake we made a few years ago in trying to go after enterprise is 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 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 1015 thousand 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. And when that happened, we built a bunch of features that like not a lot of companies or customers actually needed. Customers were no longer willing to buy wall to wall without that natural usage.

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, what to build, how to sell, how to create, resonant messaging on the other hand, and things that we're kind of learning as we integrate with Gopassian is you're either in or you're not at some point in building for enterprise, the jump to go from PLG to enterprise is a pretty big one at some point, and you could progressively get there 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 need a different permutation. And I think it becomes really, really painful 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 win that enterprise, we're not going to 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 on R and D, as well as go to market, that you're really going to win and go all in. I think at some point, after a certain amount of demand, you just need to get there and change the way you fundamentally operate. 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. It is another product requirement, but it unlocks 10 million in ARR from two or three large customers.

Harry Stebbings
When do you say yes, we will. Deviate versus no, we won't? Two answers to this. I think 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.

Parker
The actual number itself, I think is less important and more relative to like, like what your business needs at a larger scale. The broader commitment comes from at what point is PLG not gonna be enough, and how do we anticipate that? I think there's a really great article called the PLG trap that starts to outline why PLG companies, to be truly enduring companies need both PLG and sales led. The company needs to figure out at what point are they they willing to invest best to kind of go more full in relative to considering inbound requests at a customer and feature by feature level. I spoke to so many of our mutual friends and they said that one of your great skills was writing.

Janie
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 PM's on writing and written communication? I think writing can be a very powerful tool to clarify your own thinking and thoughts. 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 hybrid world 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.

Parker
And I really, really encourage all of our PM's to be writing things that are when it 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 enough context such that when they're making micro decisions in their everyday, you trust that they have the underlying context text. 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? Yeah, from a actual tactics perspective, it's not going to be fun, but it's to write more.

Janie
And when you say write more, in what way? Like write PR ds more, write updates for teams? More like what should I write? All of the bub 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. The PRD aspect, it's much higher stakes and so requires a ton of revs, which is everything you need to do.

Parker
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 meaning I have more effective by clear writing. And so from a pre meeting perspective it's hey, you should actually send out the goals and the agenda and the desired outcomes of your meeting to everyone that is attending 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 do people know what they're expected to do as they're getting to the meeting? I think after meetings is also something that I encourage PM's to be great at, which is, is after the meeting happened, how do you distill the key takeaways and the summaries assembly 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 even the process of forcing people to think about something before, like said event.

Forcing people to take said event or learnings, distill it down again, is just, 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 get better. The more specific, the better. So never ever worry about that.

Janie
Can I ask you, what are the biggest mistakes that UC PM's make when it comes to writing word vomiting? Honestly, I think people often share their writing before they get to distillation. And so people oftentimes mistake 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.

Parker
There are a lot of edge cases or requirements, but I still don't know what, why and how. And so that's number one, which is, before you think it's ready, you probably want to take five more revs at simplifying it is the biggest one. The second one is not knowing who your audience is 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 lines of code?

And the level of context they need is very different, but also the language and the why is very, very different. And so I'd call out those two as the things that I see most often. I totally agree with you there. In terms of the ICP, of the content. I say with every piece of content that we do, who's the buyer?

Janie
It also changes the positioning of every single question you ask. Why do I ask there about like, what are the mistakes? Because I'm putting my hat on of like, I'm an aspiring PM or I'm a product leader measuring the skills of a PM. Totally agree with you there. 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?

Parker
Yeah, I think for anything that is coming my way or to my death, 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, the first is just like, can I explain really simply, like, what it is we're doing and why are we doing this? And am I convinced it's worthwhile? If not, let's not take this conversation 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 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 the most important things that we need to answer or the biggest risk?

If yes, like, what is the relative cost of not answering those? Or like, getting the answer wrong? 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 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 conflict that I uniquely have that this team needs or, like, an area where I should need to be connecting dots that, like, answering that question for myself 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 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 dominate the conversation.

And if I can't, I think it's critical that I ask these questions so that we don't. A month before launch realize, like, all of these things aren't, aren't in place. 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. Vulnerability generally breeds vulnerability. Actually, I'm struggling with x right now, Janie.

Janie
I'd love to hear how you think about it. 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. 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.

And I find too many people aren't comfortable in silence when asking questions. Two big things for me. Yeah, I agree completely. I think only in the silence do people finally say the things people won't say. And that's usually right when, when the good conversation starts.

Parker
And so I agree completely. The hard element is in interviewing and in hiring. And I am a angel investment of yours. Okay. And I'm hiring a product team.

Janie
How do you advise me, an early stage company, on how to structure my hiring process for product team and product people twofold? And it really depends on are you trying to hire someone more senior or more specialized or not? You tell me. We're at a million in Arstimmers, but I'm not that late. And I'm not that early.

Parker
I personally am a huge fan of junior PM's. 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. The second is effort hungry people who are going to work hard naturally just have a much steeper slope because they're simply doing more in the same amount of time and getting all those reps in. And I think last one is, are they coachable?

Do they have the humility to know that they still have a ton to learn and are able to adapt? And I think junior folks are oftentimes the cheapest from a pure salary perspective, but also can be a huge force multiplier and just a large arbitrage opportunity. And especially in earlier days can hire for these like generalists who have these three traits, you can really train them to be effective. PM's very quickly. It doesn't get you all the way there.

But for earlier stage, like if you have someone who can spend the time, time with, with junior folks. I'm a huge fan. What are the questions that we ask in every interview? What are the must ask questions for product hires? I think in those initial parts of the top of funnel, I'm trying to get 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 closer to deciding if you want to hire a candidate, look for a much higher signal on the ability to, like, tackle the problems that we're tackling on. The track record of impact. Like, unpack that for me.

Janie
What questions do we ask? I think one is super straightforward, which is like, what is your background and what's your biggest professional accomplishment and why? I dig way, way deep into how or what they did and why they consider that to be their professional biggest accomplishment. What do you want to hear there and what do you not want to hear? One is talking less about the feature that you shipped or even I think the first good answer is I shipped something that had this impact.

Parker
I think a great answer tells me this is the problem the company or the product was facing. This is why it was one of the most important things and critical to solve. This is how I went about figuring out that it needed to be solved, how it needed to be solved. 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 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 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 product managers 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 scale and things like infra. And so I love to dig deep. I can talk to a candidate for 2030 minutes just on this question alone and leave feeling pretty confident on whether or not I want to keep having the conversation.

Janie
What percent of them impress you? It depends on if I have proactive outreach or inbounds? I think proactive outreach because I'm almost feeling the back channeling up front. Probably like 50, 75% inbounds, much, much lower just because there's really only one filter that's happening through my recruiting partner. Okay, so we're testing for harder skills.

What do we do to test for harder skills? And do we do case studies? Do we do any material test? I love. I know it's controversial, a take home, particularly before the super day.

Parker
And I use the take home to one assess should they come and meet the whole team? Very expensive use of team time and their time. And then two, if they come to the team to start to test out how they actually work with people, are they actually able to interact with critical questions? Do you come off as defensive or curious when probed? And so taking 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 going to do.

Janie
So you give them a loom problem specifically. Yep. And I say, hey, we are like roughly in this stage of maturity for our loom creator experience. Like, tell us what would, what you would do to drive a step change, improvement and getting more folks to create pretty broad. You can really take it in any way.

Parker
And for me, 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 be convinced by? I think 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 high effort and preparation.

I think, like, a good take home looks polished, 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 effort and preparation are highly indicative of how someone will attack something, how quickly and how deeply they, they will attack it. Is it a big, big investment and a big ask from candidates? Absolutely.

Yes. I think I'm extremely cognizant and grateful for that. But I think if there's a job you absolutely want, you're going to put in the effort and preparation. And I actually want to see that and what that looks like because I think it almost translates to how are they going to be in their 1st 30 days? Are they going to spend their 1st 30 days meeting people, having one on ones?

Or are they going to spend their 1st 30 days, absorbing context, but also getting really, really, really deep in their understanding and actually come out that 30 days with a point of view. 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. So you're asking how many people make it from take home to super day or super day to offer? What is super day? Super day is when they're meeting everyone on the team.

Janie
And really, okay, so basically we have first interview and like, hey, you're good enough, and then we do the take home and then the super day. What is the progression rate between each? Again, I think it depends on type of candidate. If it's a really strategic outbound, pretty high. And then if it is inbound, I'd say most of the drop off happens before it even gets to me, which is my recruiter will parse out all the resumes by the time it gets to me.

Parker
I'd say between initial conversation to take home, probably like 25%. What are the biggest reasons super days don't convert? 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 minutes hour deep dive on the take home itself. It's a small group of people within loom who show up. They've gone through your take home already, have watched a loom, and just come prepared with a bunch of questions.

They're not meant to be trick questions. We treat them as we would in a product review, which is, hey, we have a bunch of questions. We want to learn more. Let's use the time to uplevel, like, craft and quality of decisions. And I think the candidate's ability to interact with the team is really, really high.

Signal. Like I said earlier, when asked hard questions, are they curious or are they defensive? When are they open to being challenged and when do they have really high conviction? Do they have any high conviction at all and are willing to defend some of their points of view? Are they willing to be open to others?

And 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 with the team. And so I think it's as close to like, real life simulation as possible. And it's not a random case study. You've already taken the time to think through this.

And so I think it also solves for the fact that, like, not everyone is good at a random case study on the stuff, but how do you do when you've thought about something, put in the time and are then being asked to really grapple with hard questions? How quickly do you know when you've made a bad hire in product? 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 healthier spot? Did you drive clarity into a really ambiguous part of the strategy that we haven't had before? Bad hires spend the first three months still onboarding and 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 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 that first three months. Months, 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.

Janie
How do you do product reviews? How do you structure them? Who's invited? Who sets the agenda? Just help me understand that.

Parker
Yeah. So we have two types of product reviews that we have 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. And so for these reviews, I other execs will at the beginning of the quarter say like this product needs to go through the review cycle or PM's can self nominate.

There are different types of discussions that happen in these exec reviews based on 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. You have to identify what is the business outcome we're achieving and like how are we making our customers lives better. And then I think as products get more mature, we start to get into solutions and we have exact reviews on the solutions and 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. How do we gain confidence that this is going to land with customers and starts to bring in, go to market, and really talk about how we'll deliver this product? And we've evolved this process a ton. The few things that really have made this effective are the rituals we have, like before, after, and during the review itself.

Janie
What are those rituals? Before a exec review, the product leader or the PM will send out a loom pre watch 24 hours ahead of the review. 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 this artifact is prioritized in a self categorization way. And so.

Parker
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. And so for every artifact, there's always a section at the end. What does questions of cheap answers or expensive mean in product? 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 going to be many, many curiosities. 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, there are diminishing returns, for sure.

And it's time you're not spending in actually building the product. 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. How do you feel when you hear that?

I agree. How expensive is it to actually do the cheap talk exploration and when are you doing it? I think timing is really important. I think when you're at the beginning stages, like any, all ideas, like welcome, helpful. But as you get further and further along, I tend to agree you need to start prioritizing.

And when you don't, then I think you actually are causing a ton of distractions. And so when in the process are you collecting this and the types of questions that might be critical at the problem definition stage are no longer critical once you get to execution. And so I think it's when and why you're asking matter a ton and you should welcome it. But context and timing matters a ton. And the, the meeting itself, the full 45 minutes to an hour is spent on just the p zeros.

And so 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 it was really hard to open up meetings without sacrificing speed 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 really focused discussions. And that combined with after these reviews, making sure that product folks are closing the loop 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 why we made them anyway.

And that's the only way you get to disagree and commit. I do want to do a quick fly, so I'm going to pepper you with some questions 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? Storytelling at scale.

I think at every level of product management, you need to be a great storyteller and the audience and reach that. You have changes at progressive parts of your career, but even at progressive of parts of company growth 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 200 people at Loom is going to 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 that's something I'm just constantly working on, is how do I tell a story at the various points in time of company and team growth? How does AI change your role as a product leader? I think a few things. 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. What's that down to? Is that because of copilot? Is that because of. Why is that a lot of these, especially in the video space, the models are getting really good and getting better quickly.

And so we are constantly building with the assumption that the basic automation, or AI we have today is going to be 100 times better. And how do we build an experience that just gets better over time and build for that and trust that technology is going to 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 that's one. We've pulled up a lot of big bets that we may have taken in a few years, but we can take it now.

I think the second one is, in a way, it hasn't changed the way we build in a lot of ways, just because I think AI is, AI is a tool and it's not the end. And I think that's something that a lot of folks do get wrong, is like, how do I build AI? Is the question. People are AI products that people are trying to ask. And 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 it also doesn't change the way in which we build. And it's important that it doesn't. What was the most recent wow moment you have with the consumer product? And why, why was that a wow moment for you? I recently went to kind body.

It's a women's healthcare provider in the US, and it's not that new 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 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 kind body, 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 in all of their services, they do an insane thing in healthcare, which is provide transparency, transparent pricing, and it's literally up front and center. And they tell you, if you want this service without insurance, it's going to cost this much. If you want this service, it's going to cost that much.

That just both engenders trust, but is something that I've never experienced before. And then I think the last bit is they use software to tie it all together and so they have a health portal. Like most healthcare providers, I think the functionality is roughly the same, but they've nailed the user experience, which is ease of use and delightful. They also spend their time focusing on being interpretable. And so when I see a lab test and all the results, I don't usually know what most of the things mean and they tell me, 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 to grow this thing and I think it gives, gives me a glimpse of hope and excitement for this industry that's like extremely antiquated and progressively it feels like it's getting worse. And so might not be the most innovative, groundbreaking thing, but you mix all of these things together and it's still the best experience I've had. Final one, what do you know now that you wish you had known when you started in product? 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 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 didn't fully appreciate until later in my career. Janie, listen, I've gone completely off schedule for most of it, but I love a natural conversation. So thank you so much for moving with the very flexing schedule and you've been fantastic. Awesome. Thanks Harry for having me.

This was a incredible chat. So I do the vertical shows. 20 product, 20 growth, 20 sales to make advice as operational as possible for founders building today. Let me know if you would like me to dig in on certain aspects of company building, product building sales, building growth, building that we don't touch on. Let me know if there's leaders that you'd like me to have on the show and unpack those topics with.

Harry Stebbings
I'd love to hear your thoughts. You can check out today's conversation with Janie on YouTube by searching for 20 vc. But before we leave you today, we're. All trying to grow our businesses here. So let's be real for a second.

Janie
We all know that your website shouldn't be this static asset. It should be a dynamic part of your strategy that really drives conversions. That's marketing 101. But here's a number for you 54% of leaders say web updates take too long. That's over half of you listening right now.

And that's where Webflow comes in. Their visual first platform allows you to build, launch and manage web experiences fast. That means you can set ambitious marketing goals and your site can rise to the challenge. Plus, Webflow allows your marketing team to scale without relying on engineering, freeing your dev team to focus on more fulfilling work. Learn why teams like Dropbox, ideo and orange Theory trust webflow to achieve their most ambitious goals today@webflow.com.

Harry Stebbings
And talking about great companies like Webflow, let me introduce you to airtable. Half of product managers say bad processes and tools are their biggest challenges. That's why more and more companies are turning to airtable to transform their product operation. As one senior product leader put it, it's complicated to keep everybody in the loop, and airtable really helps us stay in the loop. With airtable, you'll build the right products grounded in what customers really want, unify your entire product portfolio and workflows in one place, and ship those products to customers faster than ever.

In fact, one global financial services company cut its time to market for new features by half. Maximize your team's impact, too with airtable. Give it a try for free today@airtable.com. podcast that's airtable.com podcast to get started. And finally, we need to talk about Pendo.

A really simple way to describe Pendo's value is to simply say, get your users to do what you want them to do. What is Pendo? The only all in one product experience platform for any type of application? What are the features that make Pendo so awesome? Pendo's differentiation is in its platform.

Every capability, from analytics to in app guidance to session replay, mobile feedback management and road mapping are all purpose built to work together. What is the social validity? 10,000 companies use Pendo, and we also manage mind the product, the world's largest community of product management professionals. Where do we want to drive people? Give it a try and visit Pendo IO 20 product podcast to learn how your team can use Pendo to start building better digital experiences.

There, you can also check out Pendo's lineup of free certification courses, 12 hours of in depth training for your product management team on topics from AI to product analytics to product led growth. To check it out, simply head over to Pendo IO forward slash 20 product podcast. That's 20 product podcast. As always, I so appreciate all your support. And stay tuned for an incredible episode this coming Monday with the one and only Danny Rymer at Index Ventures.

Janie
And stay tuned for an incredible episode this coming Monday with the one and only Danny Rymer at Index Ventures.

Harry Stebbings
And stay tuned for an incredible episode this coming Monday with the one and only Danny Rymer at Index Ventures.

20Product: Loom CPO Janie Lee on Three Core Skills that Make the Best PMs, How to Find, Pick and Train the Best PM Talent and Lessons from OpenDoor and Rippling on Product Breadth, Pricing and Talent Density

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1: Introduction

2: Core Skills for Product Managers

3: Talent Density and Career Growth

4: Automation and Product Development

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