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Janie Lee

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2024-06-14
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2024-06-14
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  1. “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.”

    2024-06-14 · The Twenty Minute VC · 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 · IDENTIFIED FROM THE TRANSCRIPT · source

  2. “Think it 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.”

    2024-06-14 · The Twenty Minute VC · 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 · IDENTIFIED FROM THE TRANSCRIPT · source

  3. “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.”

    2024-06-14 · The Twenty Minute VC · 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 · IDENTIFIED FROM THE TRANSCRIPT · source

  4. “I recently went to Kind Body. It's a women's health care 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 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 transparent prices.”

    2024-06-14 · The Twenty Minute VC · 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 · IDENTIFIED FROM THE TRANSCRIPT · source

  5. “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.”

    2024-06-14 · The Twenty Minute VC · 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 · IDENTIFIED FROM THE TRANSCRIPT · source

  6. “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 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 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.”

    2024-06-14 · The Twenty Minute VC · 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 · IDENTIFIED FROM THE TRANSCRIPT · source

  7. “I think a few things. One is the speed at which we develop. It is just crazy how fast the future has come. And so things that we thought we'd be shipping in five years were shipping in six months or a year.”

    2024-06-14 · The Twenty Minute VC · 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 · IDENTIFIED FROM THE TRANSCRIPT · source

  8. “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 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.”

    2024-06-14 · The Twenty Minute VC · 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 · IDENTIFIED FROM THE TRANSCRIPT · source

  9. “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, contexts, or thoughts, you're able to scale.”

    2024-06-14 · The Twenty Minute VC · 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 · IDENTIFIED FROM THE TRANSCRIPT · source

  10. “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 meeting itself, the full 45 minutes to an hour, is spent on just the P0s. And so because we ask people to prioritize, it's probably been the big.”

    2024-06-14 · The Twenty Minute VC · 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 · IDENTIFIED FROM THE TRANSCRIPT · source

  11. “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 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 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.”

    2024-06-14 · The Twenty Minute VC · 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 · IDENTIFIED FROM THE TRANSCRIPT · source

  12. “Before an exact review, the product leader or the PM will send out a Loom Free 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 I think one of my favorite sayings from someone I worked with at Open Door 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 that says”

    2024-06-14 · The Twenty Minute VC · 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 · IDENTIFIED FROM THE TRANSCRIPT · source

  13. “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 start 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 entering the review itself.”

    2024-06-14 · The Twenty Minute VC · 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 · IDENTIFIED FROM THE TRANSCRIPT · source

  14. “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 PMs 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.”

    2024-06-14 · The Twenty Minute VC · 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 · IDENTIFIED FROM THE TRANSCRIPT · source

  15. “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 move the 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.”

    2024-06-14 · The Twenty Minute VC · 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 · IDENTIFIED FROM THE TRANSCRIPT · source

  16. “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 spot. 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?”

    2024-06-14 · The Twenty Minute VC · 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 · IDENTIFIED FROM THE TRANSCRIPT · source

  17. “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. 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 up level 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, 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?”

    2024-06-14 · The Twenty Minute VC · 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 · IDENTIFIED FROM THE TRANSCRIPT · source

  18. “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 will attack it. Is it a 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 it to see that and what that looks like because I think it almost translates to how are they going to be in their first 30 days? Are they going to spend their first 30 days meeting people having one-on-ones or are they going to spend their first 30 days absorbing context but also getting really, really, really deep in their understanding and actually come out of that 30 days with a point of view?”

    2024-06-14 · The Twenty Minute VC · 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 · IDENTIFIED FROM THE TRANSCRIPT · source

  19. “Yep. And I say, hey, we are roughly in this stage of maturity for our Loom creator experience. Like, tell us what you would do to drive a step change improvement in getting more folks to create. Pretty broad. You can really take it in any way. And for me, it highlights a few hard skills. Like one is just, can you add clarity of thought to a really ambiguous problem in 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 create mocks or tell me about competitors.”

    2024-06-14 · The Twenty Minute VC · 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 · IDENTIFIED FROM THE TRANSCRIPT · source

  20. “I love, I know it's controversial, a take home, particularly before the Super Day. 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'd 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.”

    2024-06-14 · The Twenty Minute VC · 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 · IDENTIFIED FROM THE TRANSCRIPT · source

  21. “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.”

    2024-06-14 · The Twenty Minute VC · 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 · IDENTIFIED FROM THE TRANSCRIPT · source

  22. “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 are 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 20, 30 minutes just on this question alone and leave you feeling pretty confident on whether or not I want to keep having the conversation.”

    2024-06-14 · The Twenty Minute VC · 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 · IDENTIFIED FROM THE TRANSCRIPT · source

  23. “One is talking less about the feature that you shift or even, I think, the first good answer is I shipped something that had this impact. 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 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 them.”

    2024-06-14 · The Twenty Minute VC · 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 · IDENTIFIED FROM THE TRANSCRIPT · source

  24. “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”

    2024-06-14 · The Twenty Minute VC · 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 · IDENTIFIED FROM THE TRANSCRIPT · source

  25. “I think in this 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 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 much higher signal on the ability to like tackle the problems that we're tackling.”

    2024-06-14 · The Twenty Minute VC · 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 · IDENTIFIED FROM THE TRANSCRIPT · source

  26. “I personally am a huge fan of junior PMs. 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 the 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 PMs very quickly. It doesn't get you all the way there, but for earlier stage, like if you have someone who”

    2024-06-14 · The Twenty Minute VC · 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 · IDENTIFIED FROM THE TRANSCRIPT · source

  27. “I agree completely. I think only the silence do people finally say the things people won't say. And that's usually right when the good conversation starts. And so I agree completely.”

    2024-06-14 · The Twenty Minute VC · 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 · IDENTIFIED FROM THE TRANSCRIPT · source

  28. “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 a conversation. And if I can, 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 in place.”

    2024-06-14 · The Twenty Minute VC · 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 · IDENTIFIED FROM THE TRANSCRIPT · source

  29. “The most important things that we need to answer or the biggest risks. If yes, like what is the relative cost of not answering those or like getting the answer wrong? That will determine 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 what is the risk of getting this wrong? And then I think 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 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”

    2024-06-14 · The Twenty Minute VC · 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 · IDENTIFIED FROM THE TRANSCRIPT · source

  30. “Yeah. I think for anything that is coming my way 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. 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?”

    2024-06-14 · The Twenty Minute VC · 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 · IDENTIFIED FROM THE TRANSCRIPT · source

  31. “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.”

    2024-06-14 · The Twenty Minute VC · 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 · IDENTIFIED FROM THE TRANSCRIPT · source

  32. “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 beyond page 8 and still ask yourself, I don't know what I'm reading. There are a lot of details here. There are a lot of edge cases or requirements, but 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 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 going to take this and turn it into lines of code. And the level of context they need is very different.”

    2024-06-14 · The Twenty Minute VC · 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 · IDENTIFIED FROM THE TRANSCRIPT · source

  33. “Of this, and then do people know what they're expected to do as their 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 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 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 get better.”

    2024-06-14 · The Twenty Minute VC · 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 · IDENTIFIED FROM THE TRANSCRIPT · source

  34. “You say 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. 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, you should actually send out the goals and the agenda and the like 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.”

    2024-06-14 · The Twenty Minute VC · 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 · IDENTIFIED FROM THE TRANSCRIPT · source

  35. “I think writing can be a very powerful tool to clarify your own thinking and thoughts. For me, the process in it 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. And I really, really encourage all of our PMs 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 one and the why and the how and know exactly what their job is and can create enough context such that when they're making”

    2024-06-14 · The Twenty Minute VC · 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 · IDENTIFIED FROM THE TRANSCRIPT · source

  36. “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, the actual number itself, I think is less important and more relative to like what your business needs at a larger scale, the broader commitment comes from at what point is PLG not going to 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 willing to invest to kind of go more full in relative to considering inbound requests at a customer and feature by feature level?”

    2024-06-14 · The Twenty Minute VC · 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 · IDENTIFIED FROM THE TRANSCRIPT · source

  37. “Neat at all when it comes to the enterprise requirements. And what I mean by the kind of need at 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 of, I think having the top-down commitment that like, hey, we want to win at 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&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.”

    2024-06-14 · The Twenty Minute VC · 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 · IDENTIFIED FROM THE TRANSCRIPT · source

  38. “And that made the jump really hard because obviously the man 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, want 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 Elassian 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”

    2024-06-14 · The Twenty Minute VC · 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 · IDENTIFIED FROM THE TRANSCRIPT · source

  39. “Two things. One method is working your way up to enterprise, and then 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 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 teens 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 10,000, 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 SMVs, mid-market, and our prize before then.”

    2024-06-14 · The Twenty Minute VC · 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 · IDENTIFIED FROM THE TRANSCRIPT · source

  40. “With my sales counterpart. After we build the thing, unlock the revenue, I actually want to see in the next quarter 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 lab and 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.”

    2024-06-14 · The Twenty Minute VC · 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 · IDENTIFIED FROM THE TRANSCRIPT · source

  41. “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 Finro 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. In the next quarter, the results that we celebrate may not be purely owned by product teams. I love sharing core outcomes.”

    2024-06-14 · The Twenty Minute VC · 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 · IDENTIFIED FROM THE TRANSCRIPT · source

  42. “We have the big elephant in the room. 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 an enterprise PM and enterprise team is not going to be seeing the immediate hardly 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.”

    2024-06-14 · The Twenty Minute VC · 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 · IDENTIFIED FROM THE TRANSCRIPT · source

  43. “I think right now, like, Harry, I want you on our ecosystem. I'm hoping our 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 how large and or little do we want that group to be? That probably changes over time. But in our current world, 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.”

    2024-06-14 · The Twenty Minute VC · 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 · IDENTIFIED FROM THE TRANSCRIPT · source

  44. “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 there they're getting. 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?”

    2024-06-14 · The Twenty Minute VC · 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 · IDENTIFIED FROM THE TRANSCRIPT · source

  45. “That we placed in our praising 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 a 25 limit, we make 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.”

    2024-06-14 · The Twenty Minute VC · 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 · IDENTIFIED FROM THE TRANSCRIPT · source

  46. “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. 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 best 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”

    2024-06-14 · The Twenty Minute VC · 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 · IDENTIFIED FROM THE TRANSCRIPT · source

  47. “That, like, 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.”

    2024-06-14 · The Twenty Minute VC · 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 · IDENTIFIED FROM THE TRANSCRIPT · source

  48. “I want them to feel like superheroes. 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”

    2024-06-14 · The Twenty Minute VC · 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 · IDENTIFIED FROM THE TRANSCRIPT · source

  49. “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.”

    2024-06-14 · The Twenty Minute VC · 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 · IDENTIFIED FROM THE TRANSCRIPT · source

  50. “Yeah, I think there are a few things throughout the product process. I think when folks are crafting the strategy or just understanding,”

    2024-06-14 · The Twenty Minute VC · 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 · IDENTIFIED FROM THE TRANSCRIPT · source