Reposition Your Platform Like an EventBrite PMM

26:09So I'm a huge fan and you can really scale your approach depending on your budget and your resources.

26:15Jameelah Calhoun:Yeah. I love the way that you were able to pull that off because I, I've done them before the one, the last time I did a focus group, we were, we leveraged a conference that was happening where all of our like target customers were going to be at this conference. And we just rented like a hotel suite and we invited like eight to 10 people to come. And we had little like worksheets that we printed out that were intended to just be like a discussion guide. And we had one person, our PM facilitate the discussion. And I just sat there and took notes and I would like interject here and there, but you know, it was amazing.

26:54Jameelah Calhoun:It was when it was pretty affordable too, but it was nice that we got to do it in person because we leveraged the conference. But otherwise, yeah, super scrappy, just get everyone on a Zoom meeting. Yeah. I love that idea of leveraging conferences to get it done. Anytime you can be a little opportunistic to really help yourself get in front of the customer, that's the priority. Having touch points with your customer is so important. And yes, they're busy and it can be difficult. So any way you can make it easier for them and for you, the better. Absolutely. Yes. Okay. So your step one was start with existing research.

27:33Jameelah Calhoun:Step two was to identify that big problem that you wanted to solve. And you talked a little bit about how you solved that problem. Then step three is to go to now the fresh research and ideally starting with the focus groups to help you said to help identify, okay, what are the big things like the SNF test, right? Like that we definitely want to then pursue with quantitative research. So what's next? What do you do with all that? Yeah. So, I mean, I think, you know, the big last step is really to find and design tests that are an effective and efficient use of your time and your resources. So I think there are so many different types of tests.

28:18This is another example of you could do the like huge pilot in a country outside of your largest market, or you could create a website that kind of leads to nowhere that just kind of sees who clicks on it. Like there's so many different ways to iterate and test into solutions before launching. And so, you know, as an example with the situation with the infrequent hosts, we wanted to test the idea of having them sign up for a non-renewing subscription, just like a one-time payment for a two months of marketing tool support. And we didn't want to yet build that into the entire experience. So we worked with our kind of servicing team to really do something that was purely handled on the backend operationally without kind of a ton of rebuild of the entire system.

29:13So that was one way we tested into that, which was really helpful and actually helped us validate that there wasn't as much interest in that solution for the infrequent hosts as we were thinking there was going to be. And glad we did not invest in building this whole thing out before recognizing that. Yeah, and it was definitely a surprising...

29:37Jameelah Calhoun:But you ran the test. Yeah, and you ran the test to find that out. So you didn't have to spend a ton of resources. Yeah. Exactly. We de-scoped it to something that was manageable for us to do. And so I think my biggest recommendation for people when you get to this phase is really lay out all of those business questions that you have or hypotheses that you have into your questions roadmap. And that essentially becomes the way you organize the team's work is what's the highest priority question to answer about our customer, about our solution or our path forward. And then designing the tests that are going to be the lightest way to answer those highest priority questions on your roadmap.

30:22Just walk through it one by one. And it really helps to focus the team because sometimes you can get into that analysis paralysis of boiling the ocean using all of my consulting phrases. But yeah, like you don't want to boil the ocean. You want to focus on like really what question is going to clarify our path forward the most and focus on that. And then we learned with that lightweight test and pivoted our approach after that. So it was really helpful that we did it that way and prioritize that question first.

30:57Jameelah Calhoun:Yeah, I love the questions roadmap. That is so brilliant. The other thing that I could imagine would be just an added bonus of having something like your questions roadmap is that, again, like you're working hand in hand with PM during all of this and probably I'm sure other teams as well. I think establishing that shows how you and your team are being super thoughtful about how you're spending everybody's time. And again, like all of this goes back to trust and confidence in each other and the team. So not only is this just like strategic use of your time and resources, but I just wanted to call out that I would imagine that having that level of communication with the team just helps establish more trust in each other and in you and your team.

31:49So I love that. Absolutely. Absolutely. Okay.

31:53Jameelah Calhoun:So now here we've done the questions roadmap and we've designed the tests and experiments that we want to run. I guess now do we test the hypothesis? Like what happens next? Or maybe that's part of the test or the questions roadmap. So what do you do after that? Yeah, at this point, you're basically walking through that roadmap and starting to launch the tests. So some people call it the learning agenda or experimentation roadmap or whatnot. But again, this is really a moment to monitor the product, continue to evaluate, learn, and then pivot as new information is coming in. So to me, this is a really exciting time because I always tell people as a PMM, I live for the aha moments.

32:39It's really that moment, those mic drop moments where you're like, boom, here's a new insight. So I get really excited about it. So an experimentation roadmap, I'm living. I am the same way.

32:51Jameelah Calhoun:It's like I get like a hit of dopamine. Like, yes. 100%. Yeah. And even when it's not working out. So again, I mentioned those one time bundles did not take off. You're like, okay. Exactly. It's still an aha moment. So I'm here for it. I love that. So great. And it was still a moment to continue the conversation. Like getting an aha doesn't mean like that's just the end. Like when it says, oh, this didn't work. Okay, move on. No. It's like, okay, why didn't it work? Exactly. And is there still opportunity to move in a different way to kind of get at what we initially thought? Or do we need to evaluate if this was as big of a problem as we originally thought?

33:35In this situation, we pivoted basically to making the subscriptions basically a lot more convenient to cancel and rejoin. We essentially matched the behavior that we were already seeing in product of people who were maybe hosting an event for Valentine's Day. They sign up a couple months later in March or April, they would cancel. And then if they're hosting that Halloween bash, they would rejoin. But the experience wasn't built for that type of coming in and out of the product. Most times you build a subscription and you say, OK, someone's left. and it's not necessarily cohesive in that way. And so we needed to rethink the journey to ensure that that behavior was not just a bug, but actually a feature of the way we wanted this subscription to work going forward.

34:33And that was better for the infrequent host. They liked it more. They felt like this would be more, less expensive long-term. They felt like the one-time bundles just felt inconvenient and potentially too expensive over time. And so this ended up being a much better solution.

34:53Jameelah Calhoun:Yeah, yeah. You're not going to be able to change the behavior of an entire segment of people. Or at least very, very, very, very unlikely to do that. so um i really like that the way that you just the way that you guys looked at this was that the failure wasn't just like okay we tested it failed like move on as you said it seems like you used us as as the opportunity to get clarity so just a few quick hitters before we move on here so first like obviously you guys moved very very quickly and so i imagine you'd have you you have some kind of like standup meetings and whatnot. But at the end of it all, you had such wonderful results.

35:34Jameelah Calhoun:How did you socialize that like internally so that it would actually get noticed? Because many PMMs do the work and they don't really get valued for it. So curious how you guys went about that. Yeah, well, I think a huge piece is not just waiting to the end of the results to socialize the work. The work is happening all the way throughout. And that's the moment to talk about what you're doing. Talk about the aha insight, then talk about the solution that you're going to test, then talk about the results of the test, then talk about the next pivot that you're going to make. So it really should be an ongoing conversation with leadership at every stage, showcasing how you're being incredibly thoughtful and strategic about each choice that you're making along this kind of journey of transformation that you're taking them on.

36:27The second piece I always tell people is really tying everything back to revenue impact. I think it's always great to, of course, highlight nuances of customer behavior or verbatims. Leaders love verbatims. But they also love dollars and cents. And so I think really, even if it's an estimate or a forecast, like if 5 % of customers show the same behavior that would turn into this amount of revenue, like that is really the type of conversation that executives want to have. And so anytime you're thinking about something that you have found out or you have tested, tie it back to the ultimate business outcome that is going to really ensure that you're being valued to the word that you used before.

37:25And then, of course, like data-driven storytelling. It is really important to bring the funnel visuals, you know, the waterfall graphs, like make it visual, make it data oriented. And that's really going to be the story that sticks with them and is undeniable.

37:48Jameelah Calhoun:I can totally picture the funnel just as you're describing the customer journey and where people are dropping off and where they're coming back or all of that. I could see those being really effective visuals for leadership. So that's such a good tip. And the other thing that you mentioned about basically bringing them along for the ride, and I think this is worth calling out because I've personally experienced this, where you tell your stakeholders, your leadership, etc., that, hey, these are the experiments we're going to run. This is why. And then coming back later and saying, hey, remember when we ran those experiments?

38:28Jameelah Calhoun:This was the result. Right. And here's what we're going to do with that information. because I think they like I've had I've experienced me myself being just young and inexperienced in my lifetime long ago where I I would say hey I'm gonna run these experiments and I would do it but then I would just like I would know the results be like oh okay now I'm gonna go do this and I'll just forget to like I mean my my immediate leadership knew but like my stakeholders maybe be like PM sales, like they didn't necessarily know. So it wasn't a big deal. But you know, to have them coming back to me like, Hey, remember that experiment?

39:03Jameelah Calhoun:What happened with that? Like, you know, so again, not a huge deal. But it's a reminder, it was that was a good lesson for me in my career to tell them what you're going to do, do the thing and then come back and show them the results and what you're going to do with it. So and what's fair is, you know, you're running a million miles per hour, usually, so you got the result and that immediately leads to a new to-do list of a couple of things to follow up on that. So I always work with my teams on stakeholder mapping pretty intentionally and early and ensuring that there's at least some ritual around each layer of your stakeholder map so that if nothing else, there's kind of a forcing mechanism to come back to them.

39:46It's like, oh, we have that quarterly meeting with this leader that's already on the calendar. I need content for it. Oh, what about that experiment we launched? You should go back and close the loop there. So having some of those standing kind of rituals can really help hold you accountable to bringing that story back, closing the loop and staying in constant communication.

40:07Jameelah Calhoun:100%. I cannot survive without a stakeholder map. Especially at larger enterprise-sized companies, you'll have 20, 30 stakeholders. Like there's just a lot of people to keep track of and to know what they care about and all the things. So such a good tip, PMMs, please make your stakeholder maps. Okay. So if I were starting from scratch here and I was trying to build out like a very similar path that you did to solve the problem with your solution, what resources is what I need as a PMM to pull this off? Yeah. I mean, the biggest one is definitely a strong partnership with product. I think literally when I came in to this, working on growing this product as well as into the company, one of the first things I did was sit down with product and kind of really build out of RACI or just discussed how we wanted the collaboration model to look like.

41:07Like this was a situation where we were turning this product around. I was meeting like it felt like probably hourly with my like counterpart in product and my counterpart in engineering, actually, because we wanted to move really, really quickly. And so we called ourselves a three legged stool. And the three of us were just wanting to also communicate and demonstrate to our team of really united front. And so that really was the undergirding that allowed us to be successful in doing this. So I would just say, like, start with building those relationships with a particular product, potentially engineering, if you needed to pull this off.

41:49Again, the UX journey and the product-led growth element of this makes it that partnership so important. If you're in a sales-led situation, like, clearly, like, sales would be that team that you want to have that three-legged stool dynamic with. But just assess who is really going to be the critical partner that will determine your success. And then, of course, like my data teams, my finance teams, research, just making besties with a few folks. And those key teams will really make your life a lot easier.

42:23Jameelah Calhoun:Yes, yes. Yes. All of this really does come back to your internal teams and building trust and confidence in each other, making each other besties for sure. I love that. Okay. I just have a couple more questions for you. How did you monitor success ongoing? going? Yeah, I mean, I think in what I was saying earlier about keeping in contact with your executives, like it's really important to really tie the success metrics to the revenue and the P &L ultimately. So I really went through and defined like what would a healthy P &L look like? What would, how does that translate into the different parts of the funnel in terms of how many people I want to see joining, how many people I want to see churning, et cetera, et cetera.

43:13So defining those success metrics along the entire kind of P &L journey is important. The second thing I always say is really look at cohorts or distributions versus averages. My team always laughs like I basically say this to them constantly. But I think it's super, super important, especially when you're turning a product around. that's where you start to really see the differences in how your product is operating for different customers. And sometimes that those insights can be really hidden within an average. So I think pick a segment that you know is really important to your revenue story and not just look at the overall metrics of your dashboard, but then maybe those metrics cut by the particular segment that you know is really important to continue looking at.

44:06And then really make looking at the data a collective ritual. So a lot of times you have your own personal view of your dashboard and you're looking at it. But I do think it was really important for us to have forums where the whole working team would look at the success metrics together. That way we could start thinking about, because everyone in the room will notice something slightly different about the data and what they're seeing. And it just allows for a really constructive and creative conversation. Yep.

44:37Jameelah Calhoun:And it holds, not necessarily holds people accountable to it, but it gives people like a, I guess like a sense of ownership or contribution. And then a shared contribution. It just adds to the whole, I feel like I see a theme here with like trust and confidence in each other. I'm really liking it. Okay. This is my last question for you on this topic. So if you were to give a PMM who is so inspired by the story and they're embarking on a very similar journey. They're trying to borrow some of your playbook and iterate on it. Like what's one piece of advice that you have for them moving forward? Yeah.

45:12I mean, maybe the thing I would really focus on is get comfortable with understanding the business. I think that that is really, really, it sounds like it should be messaging or customers. Of course, yes. Those are very important. But I think the ability to drive results comes down to really taking an interest and understanding the levers of how the company, whatever you're at, makes money and how it translates into value for customers, how that, how behavior of customers using the product translates into the money making, et cetera, et cetera. I think that really helps you focus your time. It really helps you get, be valued as a contributor to the team and the company and the customers.

46:10And it gives you a kind of fluency and confidence, especially when you're trying to influence at the either highest levels or an organization or to different types of teams. Maybe they don't think you're trying to influence the finance team to give you some resources to run one of those fancy market research studies. Like the finance team will not just hear like, oh, we really need to understand the nuance of the customer that they want to know the numbers. So like, it sounds crazy to say,

46:43Jameelah Calhoun:like there's lots of things that bring a company together, but like at the end of the day, everybody's going to be successful if the company's making money. That's like the one shared metric for everybody in that company. So that's the shared language. And a lot of what we do as PMMs is influence. I love it. So great. Okay. Thank you so much for walking us through such a powerful playbook, an incredible story. So now I would like to transition into the second and last segment of our show, which is so fun. This is the messaging critique. So this is where you and I as product marketing experts get to analyze real world messaging.

47:24Jameelah Calhoun:And the fun part is you as the guest on the show get to pick the company that we will look at. So just some quick round rules for people who may be new to this segment. So we're going to pick a company that either we are the target audience for or one where we know the audience really well. It would not be fair to critique messaging for a company that we have no idea who their target audience is and who am I to judge their messaging. But once we disclose or share out the company we're looking at, then we are going to talk about Jamila, what you're loving about their messaging, something you wish the PMM would have done differently.

47:59Jameelah Calhoun:And then we'll just iterate a little bit on how they can take it to the next level. So without further ado, please reveal the company we are looking at today. We are looking at Calendly. And I use this tool all the time. particularly with my podcast that I mentioned earlier. And so it is really a lifesaver. So I love what they do. I also use it for my podcast. Yes. So for those of you who may not know, Calendly is most commonly known as maybe like a scheduling tool. I'll just call it that. I think Like that's probably what they're most commonly thought of as. But I'll let you kind of walk us through like, who do you think their target?

48:49Jameelah Calhoun:I guess like quickly describe who they are and who you think their target audience is. Yeah, I mean, one of the biggest elements of, you know, business is managing your time. And so this is a app that really allows for easy scheduling without the tons of back and forth of I'm free from two to three next Thursday. Eastern Standard Time and somebody else replying, well, I'm free at 10 to 11 a.m. Pacific Time. Right, right. It eliminates all of the back and forth. I think this is in particular important for small business owners as, you know, you may not have an executive assistant or somebody else who's able to manage your calendar for you.

49:38and you're managing just a lot of different stakeholders who need access to you and your time. And so I think that that is really at the crux of what they do.

49:46Jameelah Calhoun:The crux of it, yep, absolutely. I totally agree. So for those of you who may want to follow along, we're just going to Calendly's homepage and just kind of talking through the messaging on the homepage. So Jamila, what is popping out at you when you look at their messaging? I mean, it's almost interesting when you were talking about at the beginning how we hesitated to say the word scheduling. And yet it is everywhere on this page. So the very top headline is easy scheduling ahead. And it says, join 20 million professionals who easily book meetings with the number one scheduling tool. Yes, yes.

50:22And we know as PMMs, like category definition is really one of the biggest levers you have for positioning, but also one of the most challenging. And so that strikes me as I, And then, oh, I think the next headline says Calendly makes scheduling simple.

50:38Jameelah Calhoun:Well, yes, they are using repetition, aren't they? Yeah, yeah. And so it's very clear that use case. I think one of the things that as somebody who uses the product, this really feels to me a little underselling what they do. Like scheduling is like the crux of it. But there are workflows. You can get paid for different time slots. You can, you know, really kind of use it almost as a mini CRM because it sends reminders to your clients that you're meeting with, et cetera, et cetera. So, yeah, I'm surprised by how often the word scheduling comes up on here, especially if I were thinking about positioning it as beyond scheduling.

51:27And I think they say that at some point on the page. Yeah. But if you're going to move beyond, oh, yeah, Calendly's functionality goes way beyond just the scheduling link. Yes.

51:37Jameelah Calhoun:More than a scheduling link. So it's so funny because I feel like above the fold, quote unquote, they're like scheduling, scheduling, scheduling. And then when you scroll down, like, but we're more than scheduling. So it's so, I think, to your point, they're like very, I would guess I'm making a ton of assumptions here because obviously I haven't looked at any customer data or done any research at all. But I would guess, just from a funnel perspective, they probably have a huge, very large number of people who just use it for scheduling. And then they have some more advanced, more sophisticated users who do more than a schedule link.

52:18Jameelah Calhoun:Maybe that's why it's hierarchy that's associated with size of segment of customers. I don't know. That's just a hypothesis that I have for that. I think what's interesting is like generally you're the people who want the most like baseline functionality. Like once you're established in the market, they'll come to you anyway. Like Calendly kind of already the mental model already owns that space. So I think where there is opportunity is to actually help the people who do want to go beyond that start to associate that with your brand as well. So to me, most times you won't lose the people who already associate your brand with scheduling anyway, if you actually pump up more of the beyond scheduling kind of aspect of your product.

53:12And, you know, this is a trade-off we also make, like when I was talking about Eventbrite earlier, it's like, we're still a ticketing company, but we do need to pump up the fact that we do marketing and all these other things. So what's kind of the trade-off there? And that's what I always found is that the more sophisticated user is the one you actually need to communicate with. And the person who just wants the scheduling link, one, probably already knows your brand name. That's so true. And two, are going to find it through many other different pathways. Not like you would never say scheduling on your entire page.

53:48Yeah.

53:50Jameelah Calhoun:Okay. So I guess tell me one thing that you're really loving about their messaging. And then, you know, it sounds like the advice that you would give to their PMMs would be to maybe explore elevating their offering or their value a little bit more. But I don't want to take words out of you or put words in your mouth. I mean, I think, you know, they do a good job here about really highlighting functionality. I think one of the things that is tough when you have just a product suite that's growing and you have many integrations and all these different use cases is really to cleanly show the functionality.

54:27And I think the tutorials, the how-tos, the kind of easy organization of connect your calendar, add your availability. Like it's very easy to grasp and understand the kind of core functionality. And I think it's just explained in a really clean way.

54:42Jameelah Calhoun:Yeah. I also noticed they do a lot of validation, which I think is really strong. Like they mentioned 20 million professionals, Number one, scheduling tool. Then they have all of their case studies. Then they also have the security features. So they just do so much validating of the product, which you don't see all the time in product marketing. So I think that was a win. Agreed. 100%. I love the social proof, which is awesome. Yeah. Okay. So last question about Calendly. How would you, I guess, how would you take it to the next level? Yeah. Ah, well, you know, call me up. No, it's kidding. But I think ultimately, like I said, um, there are so many more features in this beyond scheduling that I would think about speaking to the core kind of need that a business owner is trying to solve versus just the kind of functional benefits.

55:46So, you know, when you're doing your product hierarchy, you can think about, or rather your messaging hierarchy, you can think about functional benefits versus emotional benefits. And to me, like Calendly is your best first employee. Like this is like helping you basically like, you know, manage your time. They're the ones sending reminders to your customers. they're the ones like helping you stay on top of things. And so they're, they're kind of like your first chief of staff hire or something. And so I'm like, how do you pump that up basically as part of the messaging?

56:22Jameelah Calhoun:I love that. I would love to run some like experiments, maybe with a focus group. There you go. That would be so fun. It would be fun. Okay. Callum Lee, we're here. We're here. Exactly. uh seriously though shout out to the Calendly PMMs like I think they're you've clearly got some fans we love the product um and so we have some ideas we'd love your feedback okay yes okay all right so Jamila I love to make space on my podcast for what I call a gratitude moment so um and that's because preparing for this podcast takes so much work and you have been incredibly generous with giving us your time and your expertise.

57:07Jameelah Calhoun:So thank you first and foremost for that and for being with us today. Yeah. And before we wrap up, I want to turn it over to you and give you a chance to give some shout outs to some PMMs who have influenced you and help shape the amazing PMM that you are today. Yeah. Oh my goodness. It's so hard to think of just a couple of folks to shout out and give gratitude to because so much of my journey has been shaped by having truly phenomenal leaders and very gratefully phenomenal women leaders throughout my career. So I'll shout out a couple. Abby Weinstein, she was my leader when I was a PMM at Audible and she just really showed me the the crux of like the practice of being a great product marketer of being a strategic product marketer.

58:04And then I'll also shout out Tamara Mendelsohn. She was my CMO at Eventbrite and just continues to be such an incredible mentor and advocate for me. So truly, I feel incredible gratitude to their leadership and the way that they have helped me grow.

58:22Jameelah Calhoun:I love that. Shout out to mentors. I wouldn't be doing this podcast today if I didn't have the mentors that I've had. Like it's just, it's life, truly life-changing. So I'm so glad that you had that too. Okay, last question for you, I promise. Where can listeners access your expertise? Obviously your podcast. Please give us any more details about that that we need to know. And then is it best to find you on LinkedIn? Yes, definitely. Look for me on LinkedIn. I'm pretty sure I'm the only Jamila Calhoun on there. If there's someone else out there, like, please let me know. I would love that. Find each other.

59:03Yeah, yeah, exactly. But that's a great way to just continue to keep in touch. And then in terms of my podcast, unpopulardecisions.com, or of course, wherever you listen to your podcast. Would love for you guys to engage and let me know what you think.

59:21Jameelah Calhoun:Amazing. Thank you so much, Jamila. Thank you. This was so fun. Yes, of course. And hey, PMM listeners, if you liked this episode, please share it with a PMM friend. And I'd be so grateful if you would leave me a review. It helps tremendously with our reach. So thank you so much for coming on this adventure with us today. I hope this episode leaves you with inspiration to take in the next step of your own journey. Thank you.