Calendly CPO Annie Pearl: Hiring Advice for Product; Calendly's Second Product | 20VC #921

1. 0:00 – 0:30

   Intro

   1. HSHarry Stebbings0:00

      (beeping) Three, two, one, zero. You have now arrived at your destination. Annie, I am so excited for this show. Rarely do I have such a fun chat pre-recording.

   2. APAnnie Pearl0:13

      (laughs)

   3. HSHarry Stebbings0:13

      Uh, I'm mostly very glad that that wasn't recorded. Um, but, uh, I... Thank you so much for joining me today.

   4. APAnnie Pearl0:19

      Thank you so much for having me, Harry. Super excited to be here.

   5. HSHarry Stebbings0:22

      I'm excited for this one, I have to say. So let's start with a little bit on you. So you've led some of the most fantastic product orgs, and most recently with Calendly.

2. 0:30 – 1:47

   How did you get into the world of startups?

   1. HSHarry Stebbings0:30

      So how did you get into the world of startups? And then how did you come to Calendly in a very swift, two to three minutes?

   2. APAnnie Pearl0:36

      Yeah. Absolutely. So, uh, started my career off actually intending to be a lawyer. Uh, and while I was in law school, I actually worked for a management consulting firm, and we specialized in working with startups. So, I was in law school, um, and, uh, assuming I would be a lawyer, but I was getting much more interested in technology and sort of the idea of building companies and products. So, uh, after passing the California bar in 2009, with the intention of being a lawyer, I ended up actually joining the founding team of a startup, uh, called Expert Financial, and we were trying to create a stock market, but for private companies. Um, and so yeah, after raising venture capital money, we hired a bunch of engineers and designers, and I took the role of leading product. So that's really how I got into product management. Um, and my time, you know, at Expert was very much zero to one. How do you get a product off the ground? How do you find product-market fit? All the peaks and valleys of kind of early stage startup life. Uh, and I think that experience really taught me about sort of the power of focus, uh, especially in the early days of finding product-market fit, just how important it is to kind of maniacally focus on solving one problem, uh, and solving it better than any alternative, um, on the market. Um, so yeah, from there I went to-

   3. HSHarry Stebbings1:40

      Thank you for-

   4. APAnnie Pearl1:40

      Yeah?

   5. HSHarry Stebbings1:40

      Ca- can I ask you quickly, otherwise I forget-

   6. APAnnie Pearl1:42

      Yeah.

   7. HSHarry Stebbings1:42

      ... when you get to my memory's terrible. Um-

   8. APAnnie Pearl1:44

      Of course.

   9. HSHarry Stebbings1:45

      One pro- one problem, I agree.

3. 1:47 – 2:45

   Framework for deciding what is the one big problem

   1. HSHarry Stebbings1:47

      What's the framework for de- deciding what that one problem is? And does that change over time, what you focus on?

   2. APAnnie Pearl1:55

      Yeah, I think at the beginning, you really wanna focus on finding where's the sort of most acute, uh, sort of visceral pain points that someone might have within some sort of problem space or some sort of market. Uh, and it may feel really narrow. Uh, it may feel really narrow at the beginning, but I think the mistake that early stage founders take... make, and we certainly s- we, we certainly, uh, struggled with this, uh, at our startup as well, is sort of, um, the shiny objects, right? We came in saying, "We have this really acute pain point around, uh, private market liquidity and being able to, to, to sort of provide private market liquidity to employees and shareholders," given how long it takes to have, you know, some sort of, uh, exit. But then we, you know, said, "Well, let's also do a capital raising platform. Oh, and let's also build a data... uh, a data room. Oh, and let's also build a way for, you know, connections to be made in a networking platform," right? And so, as opposed to just sort of narrowly sticking to this acute

4. 2:45 – 4:55

   When’s the right time to do a 2nd product

   1. APAnnie Pearl2:45

      pain that we knew was being felt in the market, we sort of decided to build new products far too soon. And I think that's, that's probably my biggest lesson from that experience.

   2. HSHarry Stebbings2:54

      How do you know when's the right time to do a second product?

   3. APAnnie Pearl2:58

      Yeah. I think you sort of get to a, a place with your first product where, um, you know, it's very clear that you found product-market fit, right? Your target customers are actually using and buying and talking about your product. Um, there's a lot of definitions out there of what product-market fit is. I think that, you know, sort of when you see it, you feel it, uh, and you know it's there. Um, and I think you have to be really diligent of, of even once you've found product-market fit, really doubling down and scaling the existing product for quite some time period. Um, and then you sort of get to a place where, okay, things are pretty repeatable, things are pretty predictable, growth is, you know, uh, something that we can really model out. Now let's actually start to think about what the next product is to build. Um, and, and I think actually maybe one of the bigger mistakes that companies make is doing that too late. Um, and so they stay on their current product, and they don't actually know how long it's gonna really take to build a brand new product, to actually get it to market, to finally see impact in the business, and so they find themselves behind the eight ball, uh, having not actually invested early enough or at least laid the foundation for what they might want to do, um, as their second product.

   4. HSHarry Stebbings4:00

      Does the second product always have to have direct tie back to the first product? Like, do they have to be completely adjacently provided or aligned?

   5. APAnnie Pearl4:08

      I don't think they have to. I think that it increases the likelihood that you'll be able to do it faster, uh, and that you'll be able to deliver additional value to the same set of users if you do. Um, uh, you know, and I think oftentimes, you know, you, you sort of think about the second product as you have an advantage because of the first, right? You have a distribution advantage. You have a data advantage. You have, you have something that you're taking, uh, advantage of. And so I think usually, it- it... they, they happen to be pretty well tied together. I don't think it has to be the case, but, uh, more often than not, I think there's a reason your second product re- relies on your first product to become successful.

   6. HSHarry Stebbings4:45

      Can I... 'Cause I used to be such a little timid interviewer, but I was like 18 when I started. Um-

   7. APAnnie Pearl4:50

      I love it. (laughs)

   8. HSHarry Stebbings4:50

      And so now I've got more like, you know, uh, sassy over time, I think would be the-

5. 4:55 – 8:39

   Does Calendly have a 2nd product?

   1. HSHarry Stebbings4:55

   2. APAnnie Pearl4:55

      (laughs)

   3. HSHarry Stebbings4:55

      ... the statement. When you look at Calendly, you know, you have such strong brand recognition within a certain-

   4. APAnnie Pearl5:00

      Mm-hmm.

   5. HSHarry Stebbings5:01

      ... market and within a certain like specific function, like role. Uh-

   6. APAnnie Pearl5:04

      Yep.

   7. HSHarry Stebbings5:05

      Is there a second product? And if so, is, is, isn't, like it's not so well known obviously, 'cause it's so dominant within, and if not-

   8. APAnnie Pearl5:15

      Mm-hmm.

   9. HSHarry Stebbings5:15

      ... have you not waited too long?

   10. APAnnie Pearl5:17

       Yeah. It's a great question. So I think about Calendly as our history and where we've come to date, we really started off as this very horizontal scheduling automation platform, right? Allowing whether you're a solopreneur or you're, you know, a, a lawyer or a real estate agent, or you own a nail salon all the way to a sales rep in an organization or a customer success rep in an organization. Um, you know, the, the breadth of use case was very broad in terms of who we served, and that really represented what we call kind of horizon one or the first, uh, you know, the fir- sort of first act of Calendly. And that's really where we grabbed a lot of market share, uh, and became kind of ubiquitous. Where we're actually transitioning to now and have been for quite some time, is going deeper into these sort of use cases where you have really strong product-market fit. So what our customers have pulled us into externally facing roles within organizations. So that's sales, that's, um, recruiting, that's customer success. Anyone who's in an externally facing role, Calendly can play a really great role in helping you schedule your meetings more efficiently. So that's the pha- the phase we're in today, going deeper there.The third phase, where I think we'll go eventually, is beyond that and to really trying to own and, and, um, and, uh, help support and deliver on the entire meeting life cycle. So, scheduling is really just a wedge into a much broader meeting life cycle. That's everything before the meeting, during the meeting, after the meeting, and there's really no one out there who's kind of orchestrating, uh, some of the most important interactions you have with your customers around meeting management.

   11. HSHarry Stebbings6:45

       I, I, I totally get you. On the verticalization side, and when you look at the different, um, requirements from each, they are very different, whether it's sales, marketing CS, or whatever we-

   12. APAnnie Pearl6:54

       Mm-hmm.

   13. HSHarry Stebbings6:54

       ... cater them to you within these different functional areas. My question to you is, does that not turn a very product-like growth organization into a verticalized sales approach dependent on the function that you're selling into, and how does the org change with product-like growth, chapter one, to verticalized use cases, number two?

   14. APAnnie Pearl7:13

       Great question. Uh, uh, so I would say this is the beauty of starting off horizontally and then going vertically, versus trying to start off vertically and then going horizontally. So, when you think about starting off horizontally, 80% of the functionality we have today will solve the use cases of those departmental users. Um, and then there's some functionality that very specifically is for the departmental users, but actually crosses across departments, right? So, as you think about meeting scenarios where you have multiple individuals within an organization, it might be a sales rep and an SDR, it might be a hiring manager and a re- and a recruiter. Uh, you've got multiple individuals in an organization who need to schedule time with someone externally. Um, we could use that same functionality to support multiple verticals, which is what we call a collective event type, a certain type of meeting to support that kind of collaborative use case within the organization. So, you get a lot of benefit from starting horizontal, call it 80%, and then when you go vertical, you try really hard to say, "What are the things we can go build that are actually gonna solve for problems across multiple of these, uh, departments?" And we, we draw a line, right? We say, "At the end of the day, we're not looking to be a point solution just for sales reps," and so if there are things that are gonna be too narrowly focused on that audience, uh, you know, we sort of have to make a judgment call around whether we're gonna go do it or not.

   15. HSHarry Stebbings8:28

       It's a really interesting strategic question of, like, what's big enough and what's attractive enough, 'cause you could outcome scenario plan in many different ways.

   16. APAnnie Pearl8:35

       Right.

   17. HSHarry Stebbings8:35

       But, uh, that, that would be an interesting internal discussion to sit in on.

6. 8:39 – 10:40

   Every PLG company eventually needs to embrace Enterprise

   1. HSHarry Stebbings8:39

      My question that I have, and you said it fantastically well before, and I love this, and so I have to pick up on it, which follows from this-

   2. APAnnie Pearl8:44

      Mm-hmm.

   3. HSHarry Stebbings8:44

      ... which is every p- product-like growth company eventually has to embrace the enterprise.

   4. APAnnie Pearl8:48

      Mm-hmm.

   5. HSHarry Stebbings8:49

      Why? (laughs)

   6. APAnnie Pearl8:50

      (laughs) Yeah. So, you know, I think there's a couple different reasons for this. I think the first one is, uh, the sort of PLG motion, which, you know, in a lot of ways is really just a self-service motion, can get you into the several hundreds of millions of dollars in revenue scale. Uh, but typically the ACV is really low, or the account value of those users. And so, just the law of, you know, sort of large numbers, uh, makes it hard to sustain kind of high year-over-year growth rates when you reach that sort of, you know, triple-digit, um, million, uh, revenue scale. I think you also o- oftentimes hit sort of a market size limitation-

   7. HSHarry Stebbings9:22

      Mm-hmm.

   8. APAnnie Pearl9:22

      ... of just solo users who can kind of pull out a credit card and buy your product. So, the first is you s- sort of growth of the PLG channel naturally slows at some point once you get into sort of, you know, hundreds of millions of dollars in ARR. I think the second thing is then you sort of have to think about the pursuit of expansion opportunities. And while you can do some of that online, going from a solo user to a small team, if you're really trying to go to, you know, medium size or large teams or multiple departments in an organization, that's gonna be a, sort of a conversation with a buyer, right? That's gonna be more of a tops-down sale. And then lastly, I'd just say almost all PLG businesses, the goal is to get as many people in the organization using your product as possible, and we kind of call wall-to-wall deployments. Um, and to do that, you know, you, you sort of have to t- engage with not just the department heads, but actually kind of your IT buyer, the ultimate decision maker around standardization, uh, of tools across an organization. So, I think, you know, you see every iconic PLG company, whether it's Slack or Dropbox or Asana or Zoom, you know, at some point they, they have to add on that sort of direct selling motion to complement the PLG business.

   9. HSHarry Stebbings10:28

      No, I, I, I agree. My, my big worry is I see so many founders move into enterprise too early. They're at like two million in ARR, and they're going, "We're gonna layer on enterprise." And I just get very worried.

7. 10:40 – 14:04

   When is the right time to move into enterprise

   1. HSHarry Stebbings10:40

      And so my question to you would be, when is the right time, do you think, to move into enterprise, and what are signals that actually you should go there? 'Cause often they'll pull you there. Should you just listen and go, or is there a right signal?

   2. APAnnie Pearl10:53

      Yeah. I think, I think we, um, to start, you nailed it, which is going too early can be detrimental, right? Hiring a bunch of sales rep when there isn't demand creates a bunch of noise, it creates extra cost for the organization, and ultimately, you know, those reps aren't gonna be successful. So, um, you know, definitely wanna, wanna be very careful around making sure you're timing it right. Um, I think, you know, one of the, the pulling mechanisms you see really is in usage data. And so at Calendly what we started to see was these core ICPs, sales, recruiting, you know, um, our, our customer experiences teams within organizations starting to become, um, you know, some level of, of mass, right? 50 sales reps within an org, 100 sales reps into an org. And you sort of start to see this pattern emerging across all of the organizations that use Calendly to say, "We've sort of hit a threshold where, um, if we were to go have a conversation with someone internally, there's enough mass here, uh, that that conversation would be productive, and there's a likelihood that they would actually want to standardize Calendly, on Calendly, uh, you know, beyond just the department or the subset of users that are using it today." So, I think you have to use the data, uh, to, to really help inform, are you ready? Um, and then I think the, maybe even a more important question is, are you ready organizationally? Uh, and that's probably one of the biggest challenges I see when people start to move up, uh, and layer on, uh, a sales team.

   3. HSHarry Stebbings12:14

      Well, let's talk about that. From the organization perspective, what are the biggest changes that you need to make when moving from PLG to enterprise?

   4. APAnnie Pearl12:21

      Yeah. So, I think, uh, really the hi- at the highest level, there's just an increased complexity that sort of happens across the whole organization, right? For, for the product org, you're going from serving sort of individuals to teams of users to departmental admins to the IT buyer. You know, you no longer get to just maniacally think about this end user. Uh, you know, on the, um, sales team, on the sales side, maybe you went from no sales team to building one from scratch or from an inbound motion mostly to an outbound motion. Similarly on the CX side, right, mostly reactionary support to how do I have now like a, a managed accounts team that's, that's working with our large customers? So, everywhere across the organization, you're sort of getting complexity within those departments. I think the second thing that happens, not just within each department, but as in across departments, and so all of a sudden now you have these dependencies popping up everywhere, right? Product can no longer just go build an AB test and release things for end users. They have to think about, "How do I involve sales? How do I make sure sales knows? How do I know that our... make sure our CS team knows?" So, a really big integration between product and the go-to-market teams and integration between, you know, the demand gen teams and the sales team, the sales and CS teams. So, all of a sudden you've got like many more dependencies across the entire organization. And then I think the last piece is, you now as an organization have multiple priorities. And again, it's no longer just PLG and the funnel and optimization of an online funnel, but you've got both of these motions. And so at all times there's gonna be questions around, which is more important? Should we be investing in this one over that one? Uh, so I think just across all those dynamics, it becomes, um, just a lot more complex in nature. And if you're not prepared for that, uh, you know, it, it likely won't be very successful.

8. 14:04 – 16:42

   Biggest challenges moving into Enterprise

   1. APAnnie Pearl14:04

   2. HSHarry Stebbings14:04

      Can I ask, for you as CPO, does this not suck? Like-

   3. APAnnie Pearl14:08

      (laughs)

   4. HSHarry Stebbings14:08

      ... you go from, like, customer delight, you know, doing product roadmaps on like incredible, like, workflow designs to, like... I mean, the... what people forget is SSO, RBAC, security enhancements-

   5. APAnnie Pearl14:20

      Yeah.

   6. HSHarry Stebbings14:20

      ... everything that comes with it. This sounds awful.

   7. APAnnie Pearl14:24

      (laughs)

   8. HSHarry Stebbings14:25

      Uh, (laughs) wh- wh- wh- wh- why, why would you do that as a product person? And from the product perspective, not an org perspective-

   9. APAnnie Pearl14:33

      Yeah.

   10. HSHarry Stebbings14:33

       ... what needs to really change?

   11. APAnnie Pearl14:35

       I think there's, there's two answers to that question. I think first is, you're absolutely right, there's blocking and tackling you have to do from a security and compliance and, uh, sort of scale perspective to help support larger and larger customers. And that's, you know, that's just sort of work you have to do. Um, uh, I think the more interesting work potentially is that as you think about these larger organizations, you think about the dynamics in them, you're actually now going from a simple use case of, "I just need to think about this one solo user," to potentially a team of users, and then potentially a team of users working with a team of users. So, from a product perspective, that's actually really, really interesting. Uh, you know, you have to think about, "How do I create value across departments in an organization who maybe don't ever talk to each other except for this product?" Uh, "How do I think about going deeper and helping to solve the needs for, again, this recruiter in a way that's also gonna unlock this use case within the sales department?" So, I actually think from a product perspective it becomes more dynamic, um, and, and actually really more interesting, even though yes, there is the blocking and tackling you just have to do, uh, in order to be able to sell into the, to the enterprise.

   12. HSHarry Stebbings15:39

       What are the single biggest challenges for you? As you layer on enterprise onto a very successful PLG motion, what has been the biggest challenge?

   13. APAnnie Pearl15:48

       I think for me and, and what you typically see is the prioritization. Um, and I think this really starts with making sure there's incredible alignment at the executive level around, how do we think about these two motions coming together to serve the overall needs of the business? Um, are we okay, for example, with slower growth in sort of the PLG business for some time period while we're investing in, in, in growing the sales business? Are we okay with just overall the sales business not growing nearly as fast because we wanna continue to, to, to grow at really high rates of PLG? So, I think the, the most important and the biggest challenge that organizations face is not having that alignment at the executive level, and then so the folks on the ground don't know, "Am I supposed to be working on a feature and service of, uh, you know, the self-service buyer? Am I supposed to be thinking about a departmental use case? Am I supposed to be thinking about, right, meeting the needs of the security and IT buyer?" And so I think it all starts with that executive

9. 16:42 – 18:56

   Can you do PLG & Enterprise from day one?

   1. APAnnie Pearl16:42

      level alignment.

   2. HSHarry Stebbings16:43

      Can you do PLG and enterprise from day one?

   3. APAnnie Pearl16:49

      That's a very good question. Uh, I don't know that you need to. Um, I think that the beauty of the PLG business is that it enables you to build a highly profitable, uh, uh, engine that in theory should allow you to, you know, with incredible unit economics, in theory it should allow you to almost kind of bootstrap the business to sort of get the opportunity to then go invest in sales and marketing dollars to unlock the larger deals. So, it's, uh, the beauty of the business model is it's much cheaper, uh, you require way, way fewer resources, and if the product sells itself and markets itself, then you really don't need to build out sales teams and, and, and marketing teams until you're really ready. So, I think the ideal approach is if you can find a way to build PLG from the bottoms up from the beginning, you, you're able to unlock a much more efficient business which allows you to then sort of, you know, be in charge of your future and decide, "When do I wanna go actually take some of this money and invest it in sales and marketing and, and move up market?" Uh, I think-

   4. HSHarry Stebbings17:52

      Mm-hmm.

   5. APAnnie Pearl17:52

      ... it's also... The, the only thing I'll say on that is I think it's also really... it's much harder to scale down than it is to scale up. Um, and when I was at Glassdoor, I had the opportunity to, um, build our self-service business from the ground up. Uh, when I joined, we were very much a enterprise focused business. We had a huge direct sales team. We were very successful in sort of mid-market and enterprise customers, and we wanted to build a self-service product from the grounds up. And so, um, the challenge with that is when you have a direct selling motion already, you, you come into, um, you, you can come into some challenges around rules of engagement as it relates to the channels. And so, you know, you sort of, you have... We had this experience of we built this self-service product, it was starting to, to sort of do well, and so you'd have a customer sign up online, post a couple jobs, and one day later a sales rep reaches out to them and says, "Hey, I wanna upsell you." Right? And, and that's a really terrible customer experience. Um, and so I think it's, it's actually a lot easier to nail the sort of bottoms up motion first and layer on top of that, um, more of a direct selling motion, I think,

10. 18:56 – 20:36

    What is great product marketing?

    1. APAnnie Pearl18:56

       than it is to come down market.

    2. HSHarry Stebbings18:57

       In a world of PLG, product marketing matters more than ever, 'cause you don't have the stabilizer of the sales rep.

    3. APAnnie Pearl19:03

       Mm-hmm. Mm-hmm.

    4. HSHarry Stebbings19:04

       Um, I think product marketing today is really, really shit. Um, it's bland. It doesn't make you feel anything. Um, when you think about great product marketing today, especially given that coming from PLG where you have a website to sell and that's it-

    5. APAnnie Pearl19:19

       Mm-hmm.

    6. HSHarry Stebbings19:20

       ... what do you think great product marketing is?

    7. APAnnie Pearl19:22

       That's a great question. You know, I, I actually would start with I think that great marketing of PLG products, uh, is not actually about product marketing. It's about the actual product itself. Um, and so the product, quote unquote, "marketing" is I use the product, I introduce the product through the course of using the product to someone else who uses the product, who then gets value, and then introduces the product to someone else. Of course, that's just one version of PLG, right? That's the viral loop of PLG. But to me, the essence of PLG, sort of quote unquote "product marketing" is using the product and getting value out of the product and therefore introducing the product to new people, and in fact, your sort of product marketing are the users versus a function within an organization. Uh, I think then as you start scaling and, and actually start moving up market, that's where the product marketing team really becomes much more en- embedded into the product org, because now you're thinking about different audiences, you're thinking about positioning, you're thinking about the, the, the buyer and, "How do I think about, um, you know, introducing the product to different buyer segments?" And product marketing, the role of product marketing, I think, actually becomes much more important as you're thinking about moving up market versus the product marketing itself is most important when you're sort of just thinking about the PLG channel.

11. 20:36 – 21:31

    How do you define product management?

    1. APAnnie Pearl20:36

    2. HSHarry Stebbings20:36

       And now that we're speaking kind of product marketing now and kind of the definitions changing over time, product management is one which is just super loosely defined.

    3. APAnnie Pearl20:44

       (laughs)

    4. HSHarry Stebbings20:44

       And I always feel too, um, naive to actually really ask what it actually is.

    5. APAnnie Pearl20:48

       (laughs)

    6. HSHarry Stebbings20:48

       Um, uh, so help me out here. Uh, it's just us. Um, how do you define product management and what does it mean to you?

    7. APAnnie Pearl20:55

       Yeah. Yeah, to me I think it's really boiled down to two main components. I think the first is prioritizing the right problems to solve. It's all about prioritization. Uh, you have limited resources and, um, the job of the product manager is to make sure that you're working on the most impactful things for the business. So, the first is prioritization of the problems that you're gonna go solve, and then the second is being able to actually build winning solutions to those problems. And ultimately your goal between both of these, prioritization and execution, is delivering impact to the business. So, that's how I, I define product management.

    8. HSHarry Stebbings21:27

       Can I ask, the other one is, like, is pro- and again, I'm peppering you

12. 21:31 – 23:12

    Is product art or science?

    1. HSHarry Stebbings21:31

       with questions here, forgive me.

    2. APAnnie Pearl21:32

       I love it.

    3. HSHarry Stebbings21:32

       Uh, is product art or science? I'm always, like, edging between the two and I'm never really sure where I land because it's so back and forth.

    4. APAnnie Pearl21:40

       Yeah.

    5. HSHarry Stebbings21:40

       How, how would you think about that?

    6. APAnnie Pearl21:42

       Yeah, so as I think about that definition of product management, right? Prioritization of problem statements are the problems you're gonna go after and then being able to actually build a winning product solution, the science can be very well applied to that first part of that in terms of identifying the biggest opportunities to go after. You've got quantitative data. You can understand how are use- people using the product today, where do they have challenges when they're using it, uh, who are our most successful users and what does their user journey look like? So, you can use a lot of data, both qualitative and quantitative, to really help you prioritize what are the biggest opportunities or what are the problems we're gonna go after. I think when it comes to the... and so science therefore, I think is very heavily influencing that part of product management. When it comes to then how do we build a winning product solution, this is where I think it becomes much more art. Uh, and there's this definition of, of sort of, quote unquote, "product sense" that, that we talk about a lot which is just sort of this combination of, you know, curiosity and creativity and intuition around how to solve a problem. Uh, and that to me is something that's, that's of course you can still use some science. You'll do discovery, you'll talk to customers, you'll get input, but at the end of the day, there's a lot more art to, to building the winning solution than I think there is science.

    7. HSHarry Stebbings22:54

       So, art's almost harder because you can't learn art like you can science I think. And so when we think about this discussion, uh, so many founders listen to the show and, uh, you're gonna be a hypothetical angel in my company. Thrilled to have you. Thank you. Uh, uh, wonderful. Um, uh, my question

13. 23:12 – 27:13

    When to hire a head of product

    1. HSHarry Stebbings23:12

       to you is, I'm founder and CEO, when do I hire a CPO or a head of product? What are the signals that now is the right time?

    2. APAnnie Pearl23:19

       Yeah. Uh, so what I typically see as you sort of... the journey around when to bring in a product leader really, really corresponds to where a company is in their growth trajectory. So, pre-product market fit, you know, uh, founder's usually doing most of the product management, working with- directly with the engineers, getting things built. Um, then usually, you know, you sort of pri- find product market fit and, and maybe you bring on your first product manager or your first, you know, sort of quote unquote "product leader," and really the job is to continue to execute on the founder's vision. Um, and so you gotta be really clear that that's the job, right? The founder typically is the one who's really driving and your job is really to execute. And then when you sort of hit this, like, level of scale of, you know, things are working well, we're humming, uh, then your job as the product leader becomes not just executing the founder's vision but, "How do I create predictability? How do I create repeatability? How do I start to hire, um, you know, a team and start to make this machine move faster, uh, to continue to essentially execute?" And then I think you hit another phase which I'll just call kind of hyper growth or late stage where a little bit of what we've already talked about. You have a product and it's humming and now it's time to, uh, to open up new growth levers. So, you're talking about new products, you're talking about new geographies, you're talking about new channels, and that's where you typically see someone bringing in a CPO, someone who's, you know, seen the movie play out before, uh, hired great product teams, you know, able to work in a really complex environment. Um, so that's- that's typically how you see the kind of trajectory.

    3. HSHarry Stebbings24:49

       Can I... Pff, again, I- r- incredibly rogue forward suggestion. I've- I've seen different profiles from interviewing the best CPOs in the world and there's like visionaries early, and I think Shreyas Doshi says this quite well, visionaries early, you know, really kind of foresee the future, craftspeople who really kind of craft it in, in different ways, um, and then there's operators. Um, and the operators are good at process repeatability, um, but they're not very...... creative, (laughs) or artistic.

    4. APAnnie Pearl25:19

       Mm-hmm.

    5. HSHarry Stebbings25:19

       And my question to you is, do you have to lose creativity and artistry and the art with scale of product management of teams? Do you know what I mean? Being CPO of, you know, 100% plus product team or whatever that is, do you have to lose that craftsmanship?

    6. APAnnie Pearl25:38

       Absolutely not. And the best product companies out there find a way not to. Um, I think maybe, uh, uh, an important part of, of that formula is, one, what's the role of the founder? Uh, typically founder CEO, but what's the role of the, uh, sort of the founder who, who sort of started with the product vision? Uh, and this is where I think, um, the relationship between the CPO and the CEO or the founder CEO becomes really critical at this stage that you're talking about, because the mistakes that I see happen is that the CEO founder goes to hire for a skill set that is either at odds with what they really need or they're not actually honest with themselves around the role that they wanna continue to play within product. And so, if you're, if you're a strong visionary founder CEO, really you just need an operator and an executor, but you go hire someone who is strong on vision, well, then you're just gonna clash. Or, you know, the, or opposite, right? You, you really need someone who's gonna bring that vision. The founder or CEO has moved into a, a, a much different role, but you go hire what you just described as sort of the, the operator. Well, yeah, you're gonna start to lose that product culture and that, that vision and that craft. So, I think it really actually comes down to understanding the dynamics between the sort of what is typically a founder CEO and the CPO and who, who's, who has what strengths, how do those complement each other, and making sure there's incredible clarity around who's gonna be doing what as it relates to product.

    7. HSHarry Stebbings27:02

       So, when we think about the hiring process, again, I'm a young first time founder, but my company is, poof, fantastic. Um, and you're an angel, so lucky you. Um-

    8. APAnnie Pearl27:12

       (laughs)

    9. HSHarry Stebbings27:12

       But we need help

14. 27:13 – 30:55

    How to structure hiring process

    1. HSHarry Stebbings27:13

       on this hiring process for the product team. How do I literally structure a hiring process? How do you do it today, and what do you wanna get out of each subsequent meeting?

    2. APAnnie Pearl27:22

       Yep. I think the most important part is starting first with, what do you describe as the competencies with which you evaluate product managers or what you need out of product managers at your company?

    3. HSHarry Stebbings27:32

       Okay.

    4. APAnnie Pearl27:32

       This can vary company to company. Um, and as we've already talked about, the definition of what product management is, uh, even something that is, uh, described differently by different product leaders. So, I think most importantly, before you even start bringing anyone in through the door, is getting onto a piece of paper, what are the core competencies that we believe are required out of every product manager here or very specifically the role we're hiring for, and how are we gonna test each of those competencies? Um, and so once you sort of have at least a general framework for what you're looking for for candidates, then it typically goes through sort of a, a three-part process. The first is usually the hiring manager phone screen, uh, or the first sort of meeting with the hiring manager. This is typically where you wanna really understand more deeply their background and their experience and their skill set, uh, and maybe even most importantly, their interest in the role. Uh, and if you can get ahead of, you know, sort of wasting time across a whole interview process just to find out that, you know, really this person's interests don't really align with, with the role, you'll save yourself time and you'll save, you know, all the folks on your team's time who have to go interview. So, hiring manager phone screen first. Assuming that goes well and the hiring manager feels confident that their experience and their skill sets are relevant to the role, then you sort of typically will move on to the panel interview, and the panel interview will really be taking those core competencies, assigning them to each of the individuals on the panel, and having a very clear and repeatable way with which you're teasing out, um, whether someone has that sort of competency or not. And the biggest m- uh, uh, the biggest mistakes that folks make on the hiring panel is they're not a lot of order and structure, and so you've got, you know, one person goes in and asks one question, the other person goes in and asks another question. Those questions are actually, like, pretty similar, and so you don't actually tease out anything new from, from, uh, you know, each of the different steps of the panel. And then post-

    5. HSHarry Stebbings29:19

       Can I ask you about-

    6. APAnnie Pearl29:20

       Yeah.

    7. HSHarry Stebbings29:20

       ... are there, are there co- are there commonalities in the competencies that we look for? Again, I have no idea. So, it's like, what, what are those, if there are some commonalities?

    8. APAnnie Pearl29:29

       Yeah. I, for me, I look at really kind of four main components of, of, uh, what I would expect out of, of product managers. The first is really all about sort of synthesizing large amounts of information, um, and data points and being able to use that to prioritize the right problems to solve. You might call that sort of strategy. Um, the second bucket is, can you then use your curiosity, your creativity, you know, your intuition to sort of tell a compelling story around what a winning product solution might look like to that prioritized problem? And that's where we sort of talk about product sense. Uh, the third for me is, can you then inspire and influence your team to deliver this winning solution that you've sort of come up with? And that's sort of the bucket there is leadership, and communication, and, and execution. And then lastly, can you sort of set up the right success metrics to ensure that you know whether you've actually made the impact to the business that you were expecting to? And if you didn't, are you sort of adaptable to testing and learning and iterating until you get it right? So, I think those are the strategy and product sense and leadership, communication, execution, and analytical thinking tend to be sort of the different buckets that, um, you know, most product organizations are looking for in product managers.

    9. HSHarry Stebbings30:41

       The reason I was looking down is because, I don't know if you can see, but I was writing on my arm. (laughs)

    10. APAnnie Pearl30:46

        (laughs)

    11. HSHarry Stebbings30:47

        Like, uh-

    12. APAnnie Pearl30:47

        A lot of things. (laughs)

    13. HSHarry Stebbings30:49

        I, I told you, my memory is not so great these days. So, okay.

    14. APAnnie Pearl30:51

        (laughs)

    15. HSHarry Stebbings30:52

        So, we're, we're testing for these competencies. Strategy, number

15. 30:55 – 34:00

    How to test for a strategic ability

    1. HSHarry Stebbings30:55

       one.

    2. APAnnie Pearl30:56

       Mm-hmm.

    3. HSHarry Stebbings30:56

       Are you a strategic mind, Annie? How do I test for, like, strategy and the ability to be a strategic thinker within product?

    4. APAnnie Pearl31:04

       Yeah, I think the strategy question really comes down to-... how do you, um, take, again, lots of different data points, uh, how do you sort of synthesize those and come up with a, essentially, prioritization framework to help you make decisions? To me, sort of product strategy is all about, um, identifying sort of what are the markets we're going after, um, what do we need to do, sort of do and build in order to win within those market, within those markets, and then ultimately, what are the competencies or, or things we need to go build in order to win within those markets. So it's a series of decisions around ultimately what you need to go build, but it's all in service of how you're gonna win within the market, the target market that you have identified for, for, for yourself. And so I think what you're looking for with strategy is, how do I essentially create a framework for decision making and prioritization that's sort of backed by this, um, you know, this cohesive plan around how we're gonna ultimately win within the target market that we're going after?

    5. HSHarry Stebbings32:03

       Can you expect a candidate to know that? And what I mean by that is that I may be a brilliant product leader. I just don't know Calendly as a business anywhere near as well as you do.

    6. APAnnie Pearl32:12

       Yeah.

    7. HSHarry Stebbings32:12

       And so, it m- it might be quite a base strategy to you. O- obviously, it would be (laughs) 'cause I don't know the business nearly as well as anyone in Calendly, but I might still be a brilliant product leader.

    8. APAnnie Pearl32:23

       Right.

    9. HSHarry Stebbings32:23

       Uh, how do... Is it wrong to expect them to come up with this strategic wisdom on a business that they don't know? Do you see what I mean?

    10. APAnnie Pearl32:31

        Absolutely. So I would, um, most of the competency questions, typically we don't see them happen either through the lens of use something from your experience, so tell me about a time when, you know, you created a product strategy or winning product strategy that ultimately, you know, uh, ended in some sort of positive impact to the business. And so you let them use their experience to, to help describe to you how they would approach a problem, or use a hypothetical, uh, which sort of puts you on the same footing as the candidate of, you know, neither one of us necessarily know, know much or are experts in this space, um, but you sort of use a hypothetical. So I think the, the, um, this set of the, uh, interview process all about, um, should all about be drawing on your past experience and, and sort of using hypotheticals. When you move into the last phase, which is, we call it kind of a collaborative working session, you see companies call it sort of the presentation, that's when you're really trying to get down to the brass tacks of how would you approach this job? Uh, then you give them the opportunity of, of time and space and the ability to really think deeply about your product, and the prompt there could be much more around what you might expect the, the, uh, the types of problems they'd need to solve in this role. So if they're a growth product manager, it might be, you know, look through and play around with our sign-up and set-up and onboarding flow, and identify where are the biggest opportunities to improve activation, right? You're trying to understand how would they approach the actual, uh, job that they'd be hired to do. Um, but I think in that panel interview, you, you know, you can be much more, um, explicit around drawing on their past experience, as well as creating

16. 34:00 – 35:07

    Presentations 101

    1. APAnnie Pearl34:00

       hypotheticals.

    2. HSHarry Stebbings34:01

       I f- I'm so glad you brought up the presentations. For the presentations, we give them kind of the problem use case, say. Um, how long do we give them? What materials do we give them? Who comes to the actual presentation? How is it structured? Never done it before, so I'm learning from you.

    3. APAnnie Pearl34:16

       Yeah. Yeah. It varies, absolutely, uh, company to company. I think it's really important to be clear with candidates how much time you want them to spend on these presentations. Um, I think it's, it really important to acknowledge the time that's being spent on the presentation, so you wanna time box it, and, and that also will allow for consistency in terms of being able to evaluate across candidates. If everyone sort of said, you know, "Don't spend more than five hours on this presentation," then you sort of can see the out- the work output from, from a similar amount of, of time being spent. So I think that's the first. Uh, the second is, you know, the prompt typically is something, uh, around your business and, and how they would actually, uh, tackle a real problem within your business, at least that's how we do it here at Calendly, um, and really allows you to hear more around how they would approach a problem they might see in the wild. And then the third piece, I think this may be the most important part, which is, to me, the presentation is actually less about

17. 35:07 – 37:17

    Mistakes founders make when hiring product leader

    1. APAnnie Pearl35:07

       me as a hiring manager or a product leader sitting on a panel. Um, yes, it's very important as, as, as, as part of the overall evaluation, but I think it's more important for the candidate to actually dig into the details of what is the types of problems I'd be working on day-to-day, and is this actually the work I wanna be doing? And I find more often than not, the presentation is a wonderful way to weed out candidates who, you know, thought they were maybe gonna be doing one job, and then they got the sort of presentation and learned, "You know, I'm not exactly sure those are the problems I wanna be tackling in my next role," and it's actually a really great opportunity to have alignment long before there's a hire made around w- what are the types of problems you'd be facing in the role.

    2. HSHarry Stebbings35:46

       What are the single biggest mistakes you think founders make in hiring this product leader or kind of a, yeah, product PM, uh, senior product PM/product leader? What do I need to be wary of?

    3. APAnnie Pearl35:57

       Yeah. I think on the leader's side, you know, some of the things we've already touched on around just sort of misalignment, uh, around what the org needs, and so again, you know, they hire an executor when they need a visionary or they hire a visionary when they need an executor. So I think on the leader side, it's much more around, um, the, the, the missteps happen when you're, you know, sort of not either honest with yourself or, uh, or explicit around what you're actually trying to optimize for. On the PM side, I think it's actually more when there's misalignment on where the company is in their growth curve, and therefore, what the actual role of a product manager is. Uh, so some PMs who were really great at early stage, um, you know, they feel stifled at late-stage companies. They don't like process. They don't want to have to, you know, do, uh, you know, um, a bunch of updates and, and, and (laughs) uh, provide statuses. Uh, and then you've got folks who are great at late stage, um, but they really can't handle the ambiguity of early stage, and so I think you kinda call this the like, uh, you know, product, um, manager and sort of, um, growth fit, uh, and I think that's usually when I see the wor- the, the biggest challenges with hires, is they aren't able to actually adapt to the needs of what the role is based on where the company is in their growth curve.

    4. HSHarry Stebbings37:12

       So, if we say we hire this very new candidate, and they're actually a junior.

18. 37:17 – 38:53

    Most important skills to build when new to product

    1. HSHarry Stebbings37:17

       Uh, let's take this as an example. They're a junior in the product team, and we think back to their early career. Um, what are the most important skills to build early on in your career in product, do you think?

    2. APAnnie Pearl37:28

       I think at the very beginning, it's all about those core PM fundamentals, right? It's all about honing everything from, uh, you know, problem prioritization, being able to use that product sense to be able to figure out how you build up a winning product solution. You know, mastering communication and storytelling and getting people on board with what you need to get built, and then, you know, building that analytical thinking muscle to be able to make sure you're setting the right KPIs and success metrics so that after you release something, you have a way to understand whether, whether it's working or not. And if it's not, you know, you, you test and learn until you get it right. So, I think that that is the most important thing, is nailing those fundamentals. I think as you start to move up in your career, a couple things happen. I think the first is, you have to do those same things, but with a larger scope, and with more complexity, and do it with more autonomy. And so, the same fundamentals are, you know, are, are gonna be there, it's just that they're gonna become, um, you know, they're gonna become more high stakes, uh, and the scope will be, will be bigger and, and the problems will be more complex. And then I think also as you start to move up, you do go from sort of that execution to strategy ownership. Uh, and so sort of early stage PM, and it's really all about execution and showing and demonstrating that you can deliver value, um, and impact to the business. And then, as you sort of start to get promoted and you move higher up in, in sort of the, the organization, you, you start to own more of that strategy and you're really responsible for kind of, kind of building that strategy

19. 38:53 – 42:27

    Thoughts on resource allocation

    1. APAnnie Pearl38:53

       and then working with the teams, uh, on execution.

    2. HSHarry Stebbings38:56

       And speaking of complexity and, and big bets as you scale into even more of a heroic sales leader, um, talk to me. Resource allocation is tough.

    3. APAnnie Pearl39:05

       Mm-hmm. Mm-hmm.

    4. HSHarry Stebbings39:05

       Do you favor concentrated bets, heavy con- concentrated resource allocation? Or do you prefer kind of scattered bets-

    5. APAnnie Pearl39:14

       Yeah.

    6. HSHarry Stebbings39:14

       ... and seeing which flowers bloom? It's almost like venture in some ways.

    7. APAnnie Pearl39:17

       Yeah, yeah, yeah.

    8. HSHarry Stebbings39:17

       How do you approach resource allocation?

    9. APAnnie Pearl39:20

       Yeah. So again, I think this really depends on where you are in your company's growth. And so, if you are, you know, pre-product market fit, your only job is to get to product market fit. Uh, if you sort of see early signs of product market fit, your job is to get that thing humming and scaling and repeatable, and you know, you wanna make this thing that's, that's starting to, to blossom, you know, blossom even more. Uh, and then as you get into, okay, this thing is blossoming, now I gotta go find the next, the next growth lever, then, then that changes as well. So, I think the, the kind of most important element of this is actually making sure there's really strong alignment at the company level around, again, kind of where you are in your growth curve, but then therefore how you have to think about investing in the core product that exists today, or placing bets for the future. And I think ways to sort of mitigate this risk really start with having a really clear product strategy. If you know where you're trying to go over the next couple of years and how, um, you know, the, the bets that you wanna place, you know, a year or two years from now, then you work backwards from that to say, "We actually have to start working on at least the discovery and the research and design for the thing we want to launch, you know, six, nine, 12 months from now." Um, and so the resource allocation, I think, can really be driven by a clear and articulate, uh, product strategy. And then I think the second thing is, you know, as companies grow into scale and, and get larger and larger, sort of that culture of innovation, um, you have to really foster that, and you have to find ways to ensure that individuals in the organization continue to feel really empowered, uh, whether it's through innovation sprints every quarter or continuing hackathons. Uh, whatever it is, making sure that there's a real culture of, of innovation so that that doesn't sort of, you know, slowly fade away, uh, as the business grows and scales.

    10. HSHarry Stebbings41:03

        How often do you revisit product strategy and when is it time to change it? If something's not looking good, how do you give enough data, but also not too much that it, it's out there for too long?

    11. APAnnie Pearl41:15

        Yeah. I think a good time horizon, a realistic time horizon for kind of the combination of a, of a product vision and strategy is, call it two to three years. Um, and I think that you then take that strategy, and again, I mentioned a little bit of around of sort of of a horizon framework, which is, uh, what we use at least at Calendly. Um, you know, we are in this horizon today. We will exit this horizon when we, you know, have met X, Y, and Z criteria and move to the next horizon. Uh, and then with it, while we're in this horizon, here are the things we need to do over the next six months to make us, you know, get us closer to essentially feeling like we've gotten to the place that we can exit this horizon. Um, so you know, I think two to three years is, is reasonable in the sense of, uh, a timeline that you would have, you know, a length of time that it would take to actually execute on your current product strategy. I think you reevaluate it, uh, quarterly. I mean, it doesn't mean you're gonna change it quarterly, but you know, on a quarterly basis you should be looking at the data, you should be looking at the market, you should be looking at the competition. You should be looking at the users and the, the sort of mix of your users and saying, "Do we still have it right? Is this still the right strategy?" Um, so I think it's check it often, but you know, hopefully you're not changing it every quarter and hopefully it's something that can endure, call it two to three years.

20. 42:27 – 43:40

    How much do competitors impact strategy?

    1. HSHarry Stebbings42:27

       Penultimate one. How impacted do you think you are by your competitor's product strategy? It's hard not to be. Everyone's like, "No, row your own race." But it's hard. You look to the side and ooh, they did that? Ooh, that looks good. (laughs)

    2. APAnnie Pearl42:37

       Mm-hmm. Yep.

    3. HSHarry Stebbings42:38

       How impacted are you?

    4. APAnnie Pearl42:40

       I personally try to, to, um, pay attention and, and understand and learn, but I try very hard to focus on our customers and our users. Um, and, and again, if we're really clear and articulate around our strategy, unless there's something our competition is doing that should make us materially doubt our strategy, um, I think, you know, we will gain far more by maniacally focusing on what we believe we need to do to win versus chasing, uh, you know, what a- another product's doing. I think the other thing around competitors is you often see, oh, their, you know, competitor just, just launched X feature. In reality, sure, you may like live in the same space, but you're not actually really competitor products, right? Uh, you know, we, we might be solving, for example, the external scheduling use case for small teams or large teams, and that might be all about calendar productivity. And so from the outside you see, oh, these two companies are, are competitive, and look, they've launched this feature. In reality, if we have a really clear product strategy, we shouldn't build that feature, 'cause it's not in service

21. 43:40 – 46:46

    Lessons from a mistake in product development

    1. APAnnie Pearl43:40

       of what we believe we need to do, uh, in order to be able to go and win.

    2. HSHarry Stebbings43:43

       Speaking of product strategy and decisions, and this is the final one, I promise, 'cause I could talk to you all day. But, uh-

    3. APAnnie Pearl43:48

       (laughs)

    4. HSHarry Stebbings43:48

       ... can you tell me a story of a product decision that you made that was a mistake? And what did you learn from it?

    5. APAnnie Pearl43:55

       Yeah. Um, so when I was at Box, uh, so I went to Box after, um, uh, my startup in, back in 2012, and had the opportunity to actually build our first kind of add-on products or our, sort of our transition from single product to multi-product portfolio. Um, and so we, you know, we did a ton of customer diligence. We did a bunch of market analysis. We had, you know, a, a very clear prototype. We validated with customers. We felt pretty, pretty, um, confident that there were gonna be sort of quote unquote, "product-market fit" with this new product. Uh, and so we made very aggressive revenue projections around what we believed we could deliver out of this new product in year one, in year two, and year three. Um, and so year one, we went to market, lots of excitement from our sales team, lots of excitement from our customers. Um, but we missed, you know, sort of those, those internal projections around, a- around what we believed we could deliver to the business, uh, pretty substantially. And there were really a couple rea- learnings from that experience. By year two and by year three, we had caught up to our projections. So it wasn't a matter of missing the mark in terms of the product decision. The lesson for me was really more around bringing new products to market within an organization where you already have a very successful core product. Uh, two things about it. One, it always takes much longer for, um, the sort of payoff of that investment to really start to materially, um, lift and impact the business. And the second is, if you have a sales organization who knows how to sell an existing product and they know how to meet their quota with that product, unless you create incentives, uh, and you find a way to sort of force them to start to sell this new product, they're always gonna go to the path of least resistance of, of essentially, how do I meet my quota? And so it was a real lesson to me of you can't just build a product and launch it and expect that the business is gonna be there. There's a lot of go-to-market implications on these new products that you have to be a sort of ahead of if you're gonna expect to see a real material lift in, in sort of year one.

    6. HSHarry Stebbings45:49

       So what would you do differently as a result?

    7. APAnnie Pearl45:52

       I think it's two things. One, I would be more realistic with my expectations and the modeling that we did around when we could expect, uh, the actual revenue. But I think more importantly, uh, I would have, I would partner more closely with and integrate more closely into the sort of selling motion and get the upfront commitment and buy-in from the sales leader or CRO, whoever that might be, that, you know, when we bring this, this, this new product to market, we're also going to do X, Y, and Z to ensure that the sales reps are incentivized, um, to actually sell the product and, and, and actually allow us to, um, you know, potentially hit our, our target for year one.

    8. HSHarry Stebbings46:29

       Annie, I'm gonna move into a quick fire round. Otherwise, I will just continue talking.

    9. APAnnie Pearl46:33

       (laughs)

    10. HSHarry Stebbings46:34

        Uh, (laughs) which I've loved. So tell me, when do you listen to users versus when do you ignore them?

    11. APAnnie Pearl46:39

        You always listen, uh, but make sure you have a sort of framework to judge whether the users you're listening

22. 46:46 – 47:38

    Which product leaders do you most admire?

    1. APAnnie Pearl46:46

       to are sort of mass market or more of an edge case.

    2. HSHarry Stebbings46:50

       Which product leaders outside of Calendly do you most admire?

    3. APAnnie Pearl46:54

       Yeah. This one's a hard one. Um, I'm a big fan of a few kind of former product leaders who are now sort of helping to educate the market on sort of best in class, uh, product management and, and kind of how to build high functioning product teams. So Gib Biddle, who was the former VP of product at Netflix. Uh, he writes and teaches a lot about product strategy. I've been able to learn a lot from him. Uh, Teresa Torres. She runs Product Talk and, and teaches a lot about continuous discovery. Uh, and then of course, Marty Cagan, uh, of Silicon Valley, Silicon Valley Product Group, really helping product leaders create empowered product teams, uh, and helping to really focus on how you deliver, uh, better results for the organization. So, I really like to draw from sort of several leaders who have now kind of moved more into the sort of teaching and,

23. 47:38 – 48:38

    Advice for product leader starting today

    1. APAnnie Pearl47:38

       uh, and, uh, and, and take those lessons to my team.

    2. HSHarry Stebbings47:41

       What one piece of advice would you give to a product leader starting a new role today?

    3. APAnnie Pearl47:47

       I would approach it like, uh, you would managing any product. I would say, what is the impact that you ultimately wanna deliver, uh, after your first year, at the end of your first year? And kinda work backwards from there to create a roadmap of, you know, what do you need to do in the first 90 days? What do you need to do in the first half? What do you need to do in the second half of how you're gonna actually ultimately deliver that impact by the end of the year?

    4. HSHarry Stebbings48:08

       What would you most like to change about the world of product?

    5. APAnnie Pearl48:11

       I would love to see more folks transition into product management from other disciplines, like customer success and support, product marketing. Uh, I think this sort of diversity of thought and experience and background that a team can really, um, learn from, from folks who come from all different parts of organizations, this can really drive kind of an outsized impact on the solutions ultimately you're delivering to customers. So I'd just love to see more sort of internal mobility across organizations

24. 48:38 – 49:34

    What company’s product strategy has impressed you?

    1. APAnnie Pearl48:38

       from folks moving into product management from other disciplines.

    2. HSHarry Stebbings48:41

       Other than Calendly, which other company product strategy have you been most impressed by recently?

    3. APAnnie Pearl48:48

       I think the way that Slack has actually been able to successfully replace the majority of my email communication, which I was very leery of when they first sort of, you know, came out with the product and, and, and sort of stated that or, or, uh, maybe didn't fully state it, but that was the goal. So I've been pretty, pretty impressed by how well Slack has been able to execute, uh, on, on sort of their strategy to ultimately sort of remove a lot of communication that maybe traditionally would have happened through email. So it will happen, you know, either asynchronously or synchronously th- through Slack.

    4. HSHarry Stebbings49:19

       Annie, listen, thank you so much for this. I'm sorry for the wayward questions. Uh, but I absolutely loved having you on, and I, I can't thank you enough for sharing (laughs) the wisdom with me.

    5. APAnnie Pearl49:27

       (laughs) Thanks, Harry. Really enjoyed it.

Episode duration: 49:35