Episode 175: Evolution of Product Management and the Importance of Diverse Backgrounds with Ryan Johnson of CallRail
I recently sat down with Ryan Johnson, Chief Product Officer at CallRail to hear all about his fascinating journey in product management and how he feels the role has changed since his career began.
And it’s not only the role of the product manager that he sees as being all-change in recent years. Ryan explained to me how he sees storytelling being far more important than it used to be in boardroom environments.
Read on to hear more about Brian's journey and his valuable insights on product strategy and communication within a company.
You’ll hear them talk about:
10:07 - Moving from being a VP to Chief Product Officer had a realigning effect on what Ryan thought made a good C-suite leader. Previously he had thought that the role of a Chief Product Officer was to be a dominant presence and a visionary sort of figure, wielding power and making things happen through immense talent and force of will. But this slightly overblown vision of the role changed, as he himself made the transition and realized that the principal desirable quality of someone in that position is to be a trusted business partner. Ryan now sees that a successful Chief Product Officer is someone with whom all the other members of C-suite feel absolutely comfortable approaching with their problems and goals. The more honest and trustworthy that relationship is, the more frank and productive the conversations had at that leadership level can be.
22:16 - Ryan previously discussed how he feels that the role of product managers has developed since he started his career, and that where before a couple of years ago there was no such thing as a product manager degree, nowadays there are lots of classes, boot-camps and other avenues to learn and get into the field in a more straightforward intentional manner. Nonetheless his takeaway advice for budding Chief Product Owners is to first look internally. Getting your head around the financial element will be vital to progress down the road, so speak to the financial and accounting departments at your work in advance of the change to your duties.
26:44 - One of the biggest and most interesting changes that Ryan has noticed in his time with CallRail is the way different departments present their reports in board meetings. He has been a part of the company for around six years and where in the past he has noticed the various departments presenting their updates in a fashion that was quite divorced from the rest of the company, now he points to an emphasis on storytelling and presenting a united cross-department front.
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Intro - 00:00:01: Creating great products isn't just about product managers and their day-to-day interactions with developers. It's about how an organization supports products as a whole. The systems, the processes, and cultures in place that help companies deliver value to their customers. With the help of some boundary-pushing guests and inspiration from your most pressing product questions, we'll dive into this system from every angle and help you think like a great product leader. This is the Product Thinking Podcast. Here's your host, Melissa Perri.
Melissa - 00:00:37: Hello, and welcome to another episode of the Product Thinking Podcast. Today, we're joined by Ryan Johnson, the Chief Product Officer at CallRail. CallRail is a lead intelligence platform that makes it easy for businesses of all sizes to market with confidence. They serve more than 200,000 companies worldwide. Ryan has over 15 years of diverse technology and product development leadership experience. And prior to CallRail, he was a VP of product at Banjo, which is now MiiM, where he helped grow the product development organization by over 300%, creating world-class AI and machine learning technology products, which led to a $100 million Series C round of VC funding. Today, we're going to talk about how product executives can think of themselves as business leaders and should rise to the occasion to help steer the ship forward with the rest of the executive team. We'll get into great topics on financials and product management, how to set and deploy strategy, and the power of shared goals in executive teams. But before we talk to Ryan, it's time for Dear Melissa. So this is a segment where you can ask me any of your burning product management questions and I answer them every single episode. So if you have a question for me, go to dearmelissa.com and let me know what it is. I'll answer it in an upcoming episode. Let's look at this week's question.
Dear Melissa, should there be project managers or scrum masters in product teams working with the product manager on execution the same way there are developers, designers, and testers? I've seen this pattern in different companies and it makes sense. On one hand, it reduces the amount of management of the day-to-day build activities, leaving the product manager to focus more on product strategy and customer and business value creation. On the other hand, this could also fit with the realms of what product operations offers at guests.
All right. So this is a good question and a very hot topic as people are evaluating the roles of agile Scrum Masters. I've seen a lot of debate about this out there in the market. So first off, though, I want to talk about the difference between Scrum Masters and Project Managers because they're actually very different. Scrum Masters specifically are there to help the team find better ways of working together. And in an agile Scrum cadence, Scrum Masters are usually a role on the team. Now, in some organizations, I've seen it where they're not a separate role. They are something that's kind of given as a title to one of the developers and they act as a Scrum Master as well. I can't tell you if that is Scrum canon or not. I don't really remember and I don't really care. But that is what I've seen. In other places, I've seen Scrum Masters be a dedicated separate role where all they are doing is Scrum Mastering, whatever that means. Scrum mastering is really, again, about trying to figure out what are the best processes for the development teams? How do we reduce hurdles to working together? And at the end of the day, I don't know if there should be dedicated Scrum Masters on each team. In my opinion, there shouldn't be. The work that they're doing, I think, can fall on engineering leadership in that team. Usually you have an engineering lead. I think it should be their responsibility as well to help figure out how the team should work better together. That's what leaders do. So if you're going to be an engineering lead on a team, I believe they should be doing that. Now, project management is different. Project management is really about how do we streamline and coordinate and make sure that projects are going to get out the door well, and they pull a lot of stakeholders together to figure that out.
Now, I don't believe there should be dedicated project managers on every single development team, but I have seen them be handy when it comes to large-scale products that have a lot of dependencies, and there's a lot of initiatives there to get it out the door. So for example, at athenaHealth, we had a program manager slash project manager who worked across many different units of product development that were under different VPs. And when we had to do cross coordination across large initiatives, they helped pull those things together and make sure that we were aligned. I saw that become really, really helpful. Now, I don't think there should be a one-to-one relationship between project management and product management by any means, but I have seen at scale when there's complex initiatives and a lot of dependencies where people with project management background, can be really helpful there to help coordinate people, bring them together and talk. Now, in smaller organizations, a lot of those product leads over those different initiatives play that project manager role and get together themselves and talk about it. And that's also great. Now, the way this differs, though, from product operations is that product operations is really trying to help enable you to get the right inputs at scale and think about cross-functional relationships and working patterns at scale. So they are implementing tools or systems that can help us work better together across many different departments, not necessarily at a team level. It's more like, how does go-to-market work with product management? That's where we would get into those types of relationships there in product operations. And usually it's about creating the systems around that that will make it easier, right? What are our playbooks?
How are we actually going to approach this? What are our cadences for meetings? That's where product operations would come in. Or they would be enabling insights into teams. They'd be creating the system for sales to get the feedback back to the product managers, about what customers are actually looking for, and then vice versa, so that product management can tell sales what they're looking for, what they're going to release as well. So that's where the difference is there. Now, that might be controversial to some people out there because there are a lot of Scrum Masters out in the world. I believe that trying to marry that with a leadership position is pretty helpful. I'm sure there are some cases where Scrum Masters have been extremely helpful for companies, though, who are just getting enabled into certain ways of working. But for me, from a product management perspective, it's not that the Scrum Masters are taking away a lot of work from the product managers, unless it's a very junior team. And there's a lot of figuring out how to work together. That's the only place I've seen where people have come in and been helpful for helping them establish a cadence for working together, running retros, getting them used to working more in an agile pattern. But I don't know if that should actually be a full-time role that stays with the team forever, or if you can enable that through coaching or leadership roles. So that's how I would really look at that. But it is good to really focus on things like product operations and then having program managers or project managers across large initiatives so that product managers can focus more on their product strategy and the customer and business value. So I hope that answers your question.
And again, this is just my opinion for what I've seen out there, but I'd welcome other thoughts of where people may have seen Scrum Masters be helpful before to help share some knowledge with me. That would be fantastic. And again, for those of you listening, if you have a question like this for me, please go to dearmelissa.com. Let me know what you're thinking. I'm happy to give you my opinion on an upcoming podcast. All right, let's go talk to Ryan. Are you eager to dive into the world of angel investing? I was too, but I wasn't sure how to get started. I knew I could evaluate the early stage companies from a product standpoint, but I didn't know much about the financial side. This is why I joined Hustle Fund's Angel Squad. They don't just bring you opportunities to invest in early stage companies, they provide an entire education on how professional investors think about which companies to fund. Product leaders make fantastic angel investors. And if you're interested in joining me at Angel Squad, you can learn more at hustlefund.vc/mp. Find the link in our show notes. Welcome, Brian. It's great to have you on the show.
Ryan - 00:07:57: Thanks for having me, Melissa.
Melissa - 00:07:59: So you have journeyed through your product management career to end up as chief product officer at CallRail. Can you tell us a little bit about your journey so far and what it was like to step into the C-suite?
Ryan - 00:08:11: So I've been in various roles inside of product development for probably the last 15 years. So as an engineering manager, kind of on the other side, managing teams, execution teams, scrum teams, all those fun things, but also bled over into product. And so I kind of did this ping pong for a number of years. And, you know, I realized because I'm not an engineer in training, that product was something that fit better for me. And so as I started my first product owner role and product manager role and kind of assimilated up, it's been a really interesting journey because I think the role has evolved so much. And everybody just comes from different backgrounds. Like up until a couple of years ago, there was really no such thing as a product management degree or all these programs and boot camps and that type of stuff. And so I think all of us that have been in it for a while, we all come from very unique backgrounds and it makes it really fun in different paths. And so most recently, I've been at... I've been at CallRail for about six and a half years. I worked with a number of folks at another company called Vitrue and we had an exit to Oracle a little over 12 years ago. So the CTO and gosh, like 10 or 15 people, engineers and people I worked with were at CallRail and it was the right time. And so I originally came in to kind of help scale the product management organization at the VP level, like put it in process. Like all the PMs were homegrown. They were great. They came from support and sales and all those things. But they never had someone that understands the craft and the processes and what we need to do. So that's really what I started in CallRail. And then over time, you know, really assimilated the product leadership executive role to most recently CPO. So focused on certainly strategy of the product direction and alignment with the company strategy, but also like on the business side, being more involved on a number of different topics.
Melissa - 00:10:07: When you made that transition from VP to chief product officer, what was one of the biggest realizations for you?
Ryan - 00:10:14: I always had it in my head that the chief product officer is like this visionary and on stage. And you just have to have this kind of presence and power. And what you realize, there are many different flavors of CPOs out there. And I was so fixated on that piece of it. And in reality, through some great advice and coaching, when you're getting to that level, there's so much more emphasis on being a trusted business partner. And what that means to me is that the CEO, CFO, anybody on that leadership team can come to me. We can have frank conversations. We have mutual trust and safety. And we're aligned on the same goals. And so when I focused a lot more on that, it really accelerated things to get me to my role today.
Melissa - 00:11:00: That's one of the biggest things I tell people when they're trying to make it into a CPO role or they really want to be promoted to an executive. I find that one of the fastest ways to get replaced as a CPO is to basically just go into your team as a product manager, right? And just get into the weeds there, but forget that you have peers now that are in the C-level. So I always tell everybody your first team is now the C-level team, right? And that you need to make sure you level up and you see them as a team. What did you do as a chief product officer to kind of ensure that you were working well with your CRO and your CEO and the rest of the team? What types of steps or even meetings or discussions did you start having so that they would look at you as that trusted advisor?
Ryan - 00:11:44: I'd say like two or three years ago, CallRail was a very product-led growth company from the beginning, and didn't have a sales team for a long time. Founders, all technical backgrounds and those types of things. And as that kind of changes to a mix of sales-led and product-led and how do you evolve and scale, it's really interesting as a leader to how do you evolve into that and how do you support these different folks? And I think what dawned on us is we kind of did these retros and we had all these product launches and it was like, okay, they went all right. Not bad, but not great. And then we looked at the ones where go-to-market teams, sales team, support team, all those leaders were in lockstep. They had all these meetings, there were milestones, there were goals, everybody knew. And the difference, the impact to our customers and the business was just dramatic. And so for me, it was like, as a product leader, we can't do this in a... Kind of in our own bubble or even in EPD, having buy-in from our sales team and our support team and getting the inputs from them that probably make it a better product because they're talking with customers every day was like a really big change to kind of go down that path of like, okay, I cannot, literally cannot be successful in my role without the partnership with you. And it's very reciprocal with CRO and CMOs, all those types of things.
Melissa - 00:13:09: So on a day-to-day basis, what types of business metrics are you looking at and staying attuned with so that you can actually develop the product strategy or make sure that it's on track?
Ryan - 00:13:21: I think it starts by level when you wake up in the morning, like how many new customers did we get yesterday? And how many new credit cards did we get? Because we have a free trial for 14 days. So you're kind of monitoring this as some leading indicators. And then looking at MRR growth, weekly, monthly basis, ARR. Churn is certainly something that's top of mind. So it's kind of like start at the very top, like what are all the things that are happening? And then based on that information, kind of dig into certain areas to say, oh, that's kind of interesting. We had an uptick in Churn this week. Is there a reason? Do we have a launch? Or is there a holiday? Like, who knows? And so really trying to start to form some hypotheses. And then I think it's really important, like, you're going to your team to help, have them help you distill and analyze it. Because most likely they have more information than you do. And so they can really help you kind of cut through the noise of like, why did this happen in this? And they can probably be like, oh, this is exactly why. And okay, what do we learn from it? How do we not do it again? Or how do we do it again if it was a positive thing?
Melissa - 00:14:25: And how does that work? Do you have a dashboard set up or people bringing you insights? Like what gets you the right information?
Ryan - 00:14:32: Yeah, so we have a lot of dashboards through Looker and we have a BI team and all that type of stuff. So we've done a lot of great moves to make sure that we have the single source of truth for data, what are their certified dashboards, right? Everybody agrees on the outputs. So it starts there. And then I think from the product side, we kind of have our own dashboards that are more focused on metrics of user behavior. And so we look at things of not necessarily daily active users, but like, what are they doing when they come to the platform? Like, oh, they added an integration. That's great because I know if our customers have at least one integration, their likelihood to churn goes down by 50%. And so we've built out these specific dashboards for the product. And then I think outside of that, with the different teams running different tests, it's a lot of show and tell just because the timeline to get that data is a little bit longer.
Melissa - 00:15:22: One thing that I see teams struggle with is trying to figure out how to define those value driving metrics for the organization or what are the things that actually matter for us. In some situations, I see like the CFO just tells everybody what they're measuring. And I don't feel like that works well sometimes, right? Because we're not talking about product leading indicators. So they'll sign them up for lagging indicators. And it's hard to tell that as a driver. What was your process for figuring out, you know, we're looking for credit cards, right? Or we're looking for this. What was your process working with the executive team and working with your team to say, hey, these are our metrics that matter?
Ryan - 00:15:57: I think it's interesting because I think in the early days of being at CallRail, I was scratched my head of like, okay, how do people not align their work to ARR growth or term reduction and all that? And so I think a big realization, especially as we grew dramatically, is you have to spend that time to connect the dots. And you have to start there and get agreement by saying, like, whether you have OKRs or strategies or whatever it is, you have to help those teams until they get comfortable. If you think of a designer, a designer is going to go like, I'm so focused on user behavior. Help me connect the dots and draw a dotted line minimally or a solid line to one of these things. And the best part about it is they want to work on impactful things. At the end of the day, the engineering product design group, they want to make sure that whatever they're working on has an impact to the business. So I think that is really the first step is aligning that. So they kind of have the aha like, oh, okay, I didn't realize that. And integration plays into how churn happens. And so, okay, great. We're going to focus on this.
If they add integrations, sure, churn is a lagging indicator down the road. And so it's really connecting the dots. And I think at the executive leadership team, the metrics, I think we just socialize them and say, hey, here are the things that we're looking at in product from usability and those types of things. And then how do we combine that with maybe some of the other data that the BI team or the ops team has? And really, I feel it's so fluid, right? There's new information. You're launching new products. And I think, you know, most importantly, one of the biggest things that we've done in our planning process and roadmap process is like, everything starts with your hypothesis. And what are you going to track? You got to do it out of the gate, because if you do it after what you learn is you can fabricate the metrics that you really want to look at to make it look good or bad. And so having that up front that we can share with the leadership team and broadly around the company of like, this is what we're going after with this work that we're doing is so critical.
Melissa - 00:17:56: You talked a little bit about this before we jumped on the call, but how product people shouldn't be afraid of signing up for those business metrics for driving AR growth and signing up for that. Can you talk a little bit about what that means in practice and how you think about it when you run your team?
Ryan - 00:18:11: There's so much commentary around this in the market right now, especially with product-led growth and those types of things. And I think at CallRail, the advantages, I mentioned earlier, that it was a product-led company from day one, very little hand holding during the process. And so certainly as the product has evolved to more of a platform and more complexities, we had to learn how to assimilate and take the best things that work together in a more cohesive system. So I think one, we just had an advantage because we were kind of wired not to be afraid of it. I think as we've grown, it's really an agreement and partnership with those teams that are working on this and saying like, okay, go-to-market team. If we build this, how many trials do you think this will generate? And how many will convert? Do we think it's going to be higher or lower based on this great sales team? And so I think it's a lot around socializing that to get to numbers for key results for OKRs, for example, to say, okay, for the whole year, we want to decrease term by X amount. And on a monthly basis, we're in a quarterly basis, we're going to kind of track these things. And so it's been a process. I think it goes from leadership down and I shouldn't be scary to sign up for these things. No different than I think marketing and sales have worked together. Like it's not a great relationship if marketing says, hey, here's all your leads. They're all wonderful. Throw them over the fence. And not my problem if we don't, if sales isn't closed and vice versa, sales going like, oh gosh, all those leads you threw over were horrible. I think this is just the evolution of the organizations coming together and saying like, hey, these should be shared goals. And they're so interconnected these days.
Melissa - 00:19:50: Talk to me a little bit about how you decide about shared goals, because I feel like this is a big thing. I was working with an organization a couple of years ago, and the CEO in that organization wanted every single leader to have different strategic goals for their organization. And what I observed there is that it created a lot of infighting in the leadership team. And also, it felt like everybody went, oh, that's just product problems to solve. I'm marketing. I can't do anything because product makes all the decisions, right? Or I'm sales. It doesn't matter if I hit my goals, even though they were signed up for AR goals. But it's all the product's fault if they don't build me these things. And it felt like a product in that place just felt like this single throat to choke. And everybody else was like, oh, I don't care. And there seemed to be a lack of ownership over that feeling like we're driving the business forward from an executive team. And to me, a lot of that comes down to those shared goals. In that organization, we actually cut that all out and put shared goals in. And I saw a tremendous change. How do you do that at CallRail? What's been your experience for how you work with your executive team and how you work with your CEO too, right? To say, these are our goals. This is how we rally behind them. And then how do you think about it, okay, this is what product does versus marketing versus sales?
Ryan - 00:21:04: I think it starts with, and we've done a really good job here of, what are our company strategies before the year starts? What do we really want to focus on and make it really understandable so that it just rolls off the tongue? It's really easy. Anybody in the company. And so, the example is this year, we want to ignite the teams and get more engagement. We want to provide a wonderful customer experience to help with onboarding and reduce turn in. And we want to grow our product portfolio with all this wonderful AI technology that's coming out. And so, it's very simple at the top. Like, okay, here are the three big buckets. Like, as a company, the whole leadership team, everybody agrees, this is the stuff we want to focus on. I think in previous years, then a subset of that leadership team, or maybe a level of set the OKRs around it and we're responsible and kind of overseeing it. And what we realized over time is it still created a disconnect between the teams executing on this and said, okay, I get the strategies, but I don't really get the OKR stuff. I'm not involved. And then when they were involved, they're like, well, y'all made the decision already. Like, so are we just going to execute on it? And so, I think for us, it was like, okay, how do we provide guidance to say, these are our strategies. Here are the OKRs. But the teams are going to tell us. How we are going to achieve those goals. Like, we can't do that anymore.
And it's just been a huge boost, right? With people being engaged and feeling more ownership and less scary to sign up for numbers, right? Like, versus, you know, you're starting with this number. Like, they're starting with, you know, how do we solve X problem? And then they're proposing a number. And then it's a negotiation to get there. So, I think that's been a really big piece is that, you know, if you were to pull anybody from the top of the company down to the bottom, what are your company strategies? Like, we all know... We're all focused on it. And we all know that we can't achieve it in a silo either. And so, we're very purposeful around things like, for example, utilizing an AI to obviously grow the product and grow the company. An aspect of that is like, how do we embrace AI internally to make ourselves better? That impacts every single department. And so, it's being clear on those nuances. Same thing with like, ignite the team's potential. And, you know, some people may say, well, that's like the People Operations Department. And then, you know, or talent and culture. And no, like, yes, they can provide a kind of high level, but it's up to us as leaders to kind of help understand how we are getting our teams to work better together in igniting that. And so, I think it's been so enjoyable because you don't have that infighting, right? Like, we all have the same goals. We're all, you know, held accountable for those goals.
Melissa - 00:23:43: When you're deploying the strategy down to teams and then asking them, like, how do we reach this? What's that process kind of look like? How are you communicating it to them? What kind of time are you giving them to go figure out how they actually reach it? And then what do they bring back to you?
Ryan - 00:23:57: We set our OKRs, we look at them quarterly before the quarter starts. I would say like a month or so before we're really giving the team early indication. This is where we think the OKRs are going to land. So start thinking about this. And honestly, it's giving them space to think through it. And I know that's difficult in product development. Sometimes we're so focused on like, gosh, we got to be like hands on keyboard delivering things. What you learn is you'll actually move faster and get better outcomes by just giving them that space to breathe and like think about it. And so for us, you know, we've kind of set up a formalized process of like how it cascades and dates. And we have someone in the company that's wonderful that manages that for everybody. So she's going to every team and reminding them and she's setting up the group Slack for it. She's setting up check-ins so that everybody understands like, hey, this is the dates that we're shooting for. Pressure testing, things. That people want to work on and sign up for and goes really amazing. It's so much work that goes into it. But having someone internally that's kind of the champion of it has made a huge difference too.
Melissa - 00:25:01: And what's her role?
Ryan - 00:25:02: So I'll give a shout out to Carrie. So her role, it's unique. She's actually from the marketing group. So she kind of became this de facto kind of project manager where we learned over time, like, gosh, we have these big projects and we need someone to like tie in the dots. And she just had a natural affinity towards it. And it just grew from there. And as she's grown, so I think now her position is director of project management and something else. But it's really awesome. Like her and now she has people that work for her that really help company wide. I think sometimes we think of project management just inside of product development. This is like across the board, like connect the dots, make sure everybody's aligned and OKRs are part of that.
Melissa - 00:25:49: So when you are looking at setting these OKRs as well, we talked a little bit about how we're signing up for business metrics here. You mentioned, too, that you have a finance and accounting background. And I'm curious how that has helped you get better at being a chief product officer or how that's maybe changed the way that you look at setting those goals.
Ryan - 00:26:09: So I feel fortunate that I have that background. I came out of school thinking maybe I wanted to be a CPA or go into traditional finance. And just through a little bit of luck in relationships, was able to bleed those together with technology and, you know, been a product manager in a financial aid, you know, very niche part of finance. So I learned some of the product craft while understanding those financial metrics. And I think for me, it just gave an advantage where it didn't matter what company I was walking into. Like I understood EBITDA, I understood ARR, I understood lifetime value and on and on and on. And so I didn't have to kind of learn like, okay, what does that actually mean? It was more about like, okay, I understand what it means. I can focus on these other things. So I think for especially like new folks into it that maybe don't have that background, it's like that natural curiosity. And so some of the things we've done here is our CFO will actually have lunch and learns and meet and greets and like literally just go and pick his brain. Because he knows the value. Like if you understand this stuff, we're going to grow better as a company, you're going to develop better product or market better. And so here we're very transparent about the health of the company, what metrics matter, what metrics don't. And so I think that's been a really big thing for folks that maybe don't have that background of like, oh, okay. They want me to understand. I think also pushing them to hold some self accountability there of like, you have to understand this. If you're going to be in this business, it's important. And it's up to us to help support them to where they feel comfortable.
Melissa - 00:27:42: If you were to give advice to a new chief product officer or somebody who wanted to become a new chief product officer on where to start learning the financial pieces, what would you say? What should they start with? What should they be looking at?
Ryan - 00:27:55: So one, certainly look internally. If you have some great partners, maybe in financial planning or accounting or finance, they usually will love to talk to you about things. Just be prepared for spreadsheets. So I think there internally, I think there's a lot of great resources. I think outside of that, there's just wonderful programs that you can do that are both remote or blended remote on site through a ton of different organizations and universities out there that have really kind of understood like, oh, okay, there's like strategy and finance for product managers. Like you see that stuff now. And from what I've seen, there's a lot of great content out there. So I think there's a lot of different options that probably you and I didn't have years ago that are pretty easily accessible, which is wonderful.
Melissa - 00:28:41: Did you know I have a course for product managers that you could take? It's called Product Institute. Over the past seven years, I've been working with individuals, teams, and companies to upscale their product chops through my fully online school. We have an ever-growing list of courses to help you work through your current product dilemma. Visit productinstitute.com and learn to think like a great product manager. Use code THINKING to save $200 at checkout on our premier course, Product Management Foundations. I feel like I had learned a lot about finance in school, but then I never thought about bringing it into product management until I started working with VCs. And then I realized board presentations, they're basically slices of your profit and loss or your balance sheet in different ways that relate back to the product. And that's all they care about, right? It's like, what is this going to do to make the numbers go up or down? And that to me was really eye-opening once I started to get into that. But otherwise, I feel like as product people, we talk a lot about adoption and we talk about usage and we talk about NPS. But it's like, what does that do to drive the business forward that we got to connect it back to?
Ryan - 00:29:49: That's right. And I think the board level is like an important aspect that you mentioned. I think as you kind of assimilate up and you're presenting in board meetings as a CPO, again, like you said, your brain is wired about all these product metrics. And at the end of the day, I had a board member tell me, he's like, listen, Ryan, I know you guys are building great things because I see it in ARR in term. So that's when I look at how you get there. Like, yes, please share in this, but like... At the end of the day, they look at the highest metrics. And if there's some delta there, positive or negative, that's when the questions come up. So I think that's a big piece of it is like, how do you succinctly tie in those things that you're doing and the impact to the business? Because the one thing you'll realize real quick, they don't understand your day-to-day. And so you really have to connect that dots in a very seamless and simplistic way. Because otherwise, you'll open yourself up for probably a bunch of questions you don't want because it's like details that don't necessarily matter to what the message that you're trying to get across is.
Melissa - 00:30:51: I find a lot of product leaders do struggle with that. It's something that I try to teach people too is how to do those board slides or communicate that story. What have you found that works well for you when you're trying to tie the roadmap back to those financial metrics? Like what types of views or information do you put together where the investors are like, okay, cool, I get it.
Ryan - 00:31:12: So what's interesting is the six years I've been at CallRail, the evolution I've seen with this board is I feel we would go in there. It was very departmental focus, right? Like product is going to give their updates and engineering and sales and marketing and all that, which is fine. But one of the things that was a pretty dramatic change to our leadership here and in our CEO was you have to tell that cohesive story and it has to be back to back. It can't just be a product thing and assume that the board is going to make the connection to something else you're talking over here in marketing, for example, like they just don't. And so for us, the real big thing was storytelling. Like, okay, we're going to give a product update. But in the product update of, let's say, a new launch, there's go to market, there's support, there's sales, and how we speak is like fluid between each other. So we all have a speaking part for those. And that was just the huge thing where, you know, we came out of there, the board didn't have any questions. And they were like, yeah, y'all are talking to each other. And it makes a lot more sense because we're connecting those dots. And so I think that was a big positive that we've done over the past couple years, is like we collaborate every day. We're partners every day. How do we show that through the board and have that messaging, so it's not so split up? And it's given them so much more confidence in us of like, okay, yeah, we know that you're locket staff because very apparent based on how you're telling this narrative.
Melissa - 00:32:42: I love that. And I haven't seen many board presentations actually given that way. So I think it makes so much sense to show like a united front across the C-suite too. Like we're all working on this together. So when you do that, do you do any like mini department updates or is it like, hey, here's the big update. Let's like, we're going to weave this story through. What does that kind of look like?
Ryan - 00:33:01: So I think it really depends on the type of board meeting that's happening, the time of year. We put a lot in the appendix. And I think that's the stuff that used to kind of get pulled up into a 200-page prezzo for a board meeting. And so they're all super intelligent and smart people. Like they'll read through it. And if they have questions, I'll let you know. So we do some individual department type of things like bug variances and those types of things in engineering and updates on roadmaps. Like here's the holistic roadmap. How are we progressing against it? What are the call-outs? But again, we really kind of left that to the smallest part of maybe covering during the actual board meeting and really focusing on what are the big things that are moving the business? What are the big concerns or challenges that we're solving? And then kind of a smaller focus on the individual departments towards the end, if you will.
Melissa - 00:33:53: That's really neat. And has the feedback been positive from the board members? It sounds like yes. Do you hear any negative feedback about it or is everything swimming?
Ryan - 00:34:02: It's sometimes shocking, like you don't have any feedback. You know, he's kind of on edge the whole time. Like, okay, what question, what feedback am I going to get? And it just resonates better. Like you've connected all the dots. It's been really awesome to see and be able to feel that partnership because that's how we're operating day to day. So why wouldn't we do that during a board meeting? So yeah, all very, very positive feedback on that. And I would tell people like test it out with an area. Like maybe just if you have one big project, like have all those people kind of collaborate together and have different speaking parts. And I think that's how it evolved with us too. I don't think it was a light switch. I think it was like, okay, here's one big project. We'll do that. Then we'll do the company. And I think over time it was like, okay, we have a lot of big things we need to talk about. That's the majority of the meeting versus the individual department updates.
Melissa - 00:34:53: That's really cool. So this story that you're weaving for the board, how are you bringing it back to the teams too? And how are you connecting it back to the product strategy? We talked a little bit about deployment. I'm curious, are you telling similar stories when you go out and deploy your strategy? Are you doing company presentations on how that's all going to work? What do you do to present that united team, I guess, back to your own teams?
Ryan - 00:35:15: I think it's a mix of a variety of things. One is I try to have them collaborate on the presentation itself and the information itself from the beginning. Because again, they have some details and things that they're closer to. And so one is bringing them in to help create the storyline. And so I think they feel really great about that, that it's just not a readout from the board meeting. It's just like, oh no, those are like the slides that I did. And in some cases we invite them in, which I think is great for career growth to kind of understand and come and present in front of the board. And so we regularly do that. And one of these projects of like, okay, bring the lead PM and the engineering manager and let them talk about this new project on the EPD side. So that's a piece of it. I think giving a readout to the team, they kind of desire, right? Like everybody knows, oh, there was a board meeting this week. So how do you distill that information back to them and be transparent about it and say, hey, here are the, the things that came up here, the things that they're thinking about, here's what went well, here's their concerns. And so I think it's that communication to them. But the hope is that you're not presenting anything to the board and then being like, okay, board approved it or board agrees. And now you'll have to go figure it out. Been there, done that. It can work, but it's certainly more engaging for folks to be in there as a part of that process. And then it's no surprise. They're usually asking like, oh, did you get to that slide? What did they say? They're craving that feedback.
Melissa - 00:36:43: I bet that helps you in preparation for the board meetings too. So it's not just all on you.
Ryan - 00:36:50: Oh my gosh, yes. I wouldn't know what to do without some of my key people in there from the design and look and feel of it to the content. So yeah.
Melissa - 00:36:59: That's a nice way to bring everybody together. I wanted to dive in now a little bit to product strategy and talking about kind of like portfolio strategy with you. We talked a lot about like strategic OKRs and where we're going after with them. Another thing I see product leaders struggle with is how to balance innovation with growth goals from our existing product. And then also things like keeping the lights on or things that just need to get done, right? Like if we had to replatform something, how do we put that in? How do you think about balancing growth with those other key factors?
Ryan - 00:37:31: I think one is starting out being very transparent as you kind of cross the company. So we used to kind of do this roadmap exercise in the past and it was mostly inside of product development to decide. And we met with the CEO and CPO at the time and all that. And of course, they're engineering product people. And it was like, yeah, we should go and do this. And we had some systems to get feedback from other teams, but it just, as we grew, it just did not resonate. Right? It's just like, well, I have ideas on that and I could help with that. And so really we started to get a better formalized process with that of like getting feedback early of like, hey, okay, we want to invest in these or this is what the next quarter looks like. There's going to be more work on cloud services stuff just because we have to get through these updates and they're really complex. So we can't do as much new features. Number one is just trying to be so transparent about it. This is what we're thinking for the next quarter or two quarters. Pressure testing that against as many people as you can to say like, are we missing something? Is something misaligned? And then I think the balance of innovation, it's tough. I feel there's ebbs and flows. Think back to the pandemic. I think everybody kind of went to like, just tell me what to do. I'm dealing with all this stuff around me. I don't have the brain space. And I even felt that way some days. Just give me a task list. Let me go execute on it. And then what you see now is the resurgence of like, no, people want to be involved with strategy. They want to have that time. And so a piece of it is our company kickoff theme was create space. And so create space to think, create space and realize like, hey, we have to pull you out of this day-to-day execution to think about things.
We've done programs like CallRail Labs where it was, we would see every day something on LinkedIn, the AI about competitors or pseudo competitors. And it was like, how the heck are they, delivering something like on a monthly basis? And I was like, well, we can actually do that too. Like this and that. And it was like, okay, we should do that. And so it was like, great. Let's put alpha features out once a month and get early feedback. And then we'll figure out how to productize once we get that feedback. And then it turned into a program in marketing said, hey, like we should celebrate this. This is good for customers. They're a part of the process of developing the latest and greatest features and product. And so, you know, that was a piece of it too, to realize like this type of work is very different than revenue or churn reduction or those types of things. And I think it's a challenge for all of us just like, making sure we really are serious about creating space. One of the things we specifically did in product development, and we're still early days, kind of did these six-week blocks and cycles of work. And it was really focused on like, okay, what do we want to accomplish in six weeks? What can we demo? And at the end of it, you have a reflection week, and that was really important, because I feel the way we were planning in the past was just like, oh, gosh, like the next quarter is here. And it just seemed never ending. And I think with this, it's been really beneficial to like, no, the teams are not working on new features this week. They're analyzing, did they meet their goals? And is it the metrics? And what do they learn? And they're sharing demos with each other. Like they have time so that I was left out of it. Like any leadership and product and engineering, like we didn't even get invited. It was like literally the team showing off work to themselves. And it was so impactful. Like it's kind of amazing that just being able to share those things with your peers was like and giving them the space to do that has really kind of shown balance, like we need to spend more time doing things like that.
Melissa - 00:41:11: I see a lot of organizations do the like one week reflection before they go into the next sprint or things like that. Do you ever find that there's times where the team needs longer to actually like pull together a strategy or experiment around something or do a deeper dive in customer research? And how did you handle that?
Ryan - 00:41:29: Certainly team by team, you know, you have variances there of, hey, we would like more time and those types of things. And so we try to accommodate it as best as possible. We realize so many things can change and maybe a tactical thing changes and they need to react to it. And it's just not reasonable to hold them to that one week. And so we try to flex where it makes sense with that.
Melissa - 00:41:51: For the labs too, I want to go back to that piece. I like the idea of pulling people off into innovation centers, but where I feel people struggle with it is like, how much do you invest in that? How do you think about that compared to everything else? And then if they do create an alpha that works, how do you reintegrate it back into your strategy?
Ryan - 00:42:09: Great question. So I think our initial kind of driving force with alphas was like, how do we just get feedback from customers early and often before we even figure out how to fully productize this? So one, can we set up a process so that we can do this once a month? So very short cycles, a couple of weeks. And that's kind of how we capped it of like, okay, don't create an alpha. It's going to take two months to make. Hopefully, it's like a week and then we could test it and we put it out there and start getting feedback. So I think giving the team clarity and context on that, it was really important around the like, okay, this is the purpose of this program. This is what we're trying to do. And then what was amazing is they would literally just tell me like, hey, this is the alpha that's coming out. This is what we're trying to test. This is where we think it is. We've already talked with the go-to-market team. They feel this is something they can go and talk in the market, which is great. I think the hardest part, and I talk about this quite a bit, especially with AI technology, the AI itself, the tech is so amazing and it can solve so many more things than we even understand today. I don't think that is the challenge in the market.
The challenge in the market is to me, how the heck do you productize this stuff? Because you can't assume user behavior is going to be the same, that they're going to want to digest data in the same ways, or they want to view things in the same ways, like that whole thing could change. And so I think that's the hardest part of like, okay, how do you productize something that's not noise in the market that actually provides value and people understand it? And so for our alphas, we look at user behavior, we look at feedback, and then we say, hey, we think this is a good candidate based off of that to be part of a new product. And so maybe we wait for a few of those, which is what we're doing now, where we have three alphas that we previously had success with, and now it's being built in and being productized to a new product in the portfolio. Or is it, hey, from these learnings, we should go and help provide more value to existing products. So it's a mix of those. And it's a debate, right? It's outside of even EPD of the business stuff that I've been talking about. So working with the go-to-market team, do they feel it's marketable and all that? And it's really been great for us. I think that muscle was somewhat new for us to be that iterative and quick and dirty. And we've really seen the dividends of it on our most recent product launch almost a year ago. Again, started out with some alphas and it's really taken off.
Melissa - 00:44:41: And do you have like a separate team who's running these alphas or is it like baked into the product teams?
Ryan - 00:44:46: So there is a team that it falls under today, which is like our conversation intelligence team, because that's where it's coming out of. But the goal is to make this broad, right? Because what you don't want to happen is like, oh, these are the innovator teams and these are the lights on teams. Like that never works. That's so... Unmotivating and demotivating. So for us, it's like, how do we broaden that and say like, okay, it made sense we started here, but then how do we keep labs to say like, oh, and this other piece of the product that maybe had nothing to do with it, like getting the teams to think about that. So that's kind of the next evolution we have with that is like, great, we have one big team that really embraced it, kicked it off. How do we kind of scale that across the company?
Melissa - 00:45:29: So you talked a little bit too about AI just a minute ago. I'm curious, as you're looking to the future of AI and thinking about strategy, like we talked a little bit about, hey, I don't think people are going to view data in the same way. What other challenges do you see or what are you keeping a pulse on as a CPO?
Ryan - 00:45:46: One of the challenges is getting organization and certainly the product organization comfortable with the new technology. Like, how do we use these things in our everyday kind of working life that really make things better? I think if you talk to a lot of PMs, it would be some of the research stuff is hard to distill, some of the data. And so cutting down on that cycle time and being able to prototype and being able to do these things that just took a lot longer, I think is exciting. And so as leaders, we have to really empower the team and say, hey, if you're using these things, share with the team. Let's learn from it. No one should be afraid about job displacement. It's really about how do we make better product managers and other types of roles inside of the company. And I think that goes to taking mundane tasks out of your hands to helping me formulate strategy. I can take all this data now and kind of say, hey, give me a rough draft of where you think this is going. That's wonderful. It saves so much time. And so I think it's really embracing it. The watch out is moving so fast, making sure people are doing it the right way, making sure you have an organization. And we have some great people here that think about it every day, which is compliance, the security, those types of things, because that's what matters to our customers. And it has for since the beginning of CallRail. But now it's just the next evolution of it, of saying like, okay, like, yes, these things that we use that are AI based, your data is not being trained on it. And these are the safety provisions that we have in here. And this is how we think about it. So I think that's where like the cautionary stuff is. And, you know, I always mention like we're going to have an oh crap moment at some point with all of this. Right. That's going to have us take a pause in the market for someone that's doing things with AI that just isn't isn't great. So I think it's empowering people to be innovative and think about it, but also protect the company, protect your customers, those types of things.
Melissa - 00:47:38: Well, this has been really fascinating to learn about. Thank you so much, Ryan, for being on the podcast. If people want to learn more about you and CallRail, where can they go?
Ryan - 00:47:46: You can find us at callrail.com and also on LinkedIn. So I regularly post all of our updates and cool things that we're working on. So feel free to connect or drop me a note.
Melissa - 00:47:58: Thanks again for being on the Product Thinking Podcast, Ryan.
Ryan - 00:48:01: Thanks for having me.
Melissa - 00:48:02: And thank you to our listeners out there. We will be back with another episode next Wednesday. So make sure you go to productthinkingpodcast.com, like this episode and subscribe on any of your favorite platforms or on everything, Spotify, Apple, YouTube. And if you have a question for me about product management, you can submit them to dearmelissa.com where I answer one of those questions every single podcast episode. We'll see you next time.