Why Smart Pricing Strategies Fail in SaaS Businesses

Alexa, it is so fun to have you on the podcast. Um, I've gotten to know you over the last few months and you've had this incredible career in monetization. But going way back, you studied international studies at Bryn Mawr. You, you did nearly 3 years at Deloitte. I think you did a year in sales, if I'm not mistaken. And then 18 months at ProfitWell, where you were a pricing strategist, followed by 8 months at Paddle after the acquisition, a year at Seismic leading pricing and packaging. And then you joined Dashlane and you're the lead PM on pricing and packaging. So there is a lot of surface area to cover, a lot of learning. I'd love to hear you talk about your journey in your own words. How did we get to now?

Yeah. And first, I want to say thank you so much for having me on today. This is a great chance to get to talk through what I've experienced and share some of the hard lessons that I've learned and kind of what's getting me going in this space. You know, I entered the career force as a consultant at Deloitte. And that was really because I didn't know what I wanted to do, but I did know that I wanted to learn a lot about the way in which business ran and how we could evolve business to be more virtuous and equitable. I always had this desire ever since I was at Bryn Mawr to figure out a way in which to optimize business, not only for the customer, but for the people that are part of that business. And so my journey in my professional career has taken me down a series of paths, but it's really been a journey that has allowed me to listen to my gut and respond to what feels good and what feels right and allows me follow my curiosity. So I entered the world of monetization through ProfitWell, and I was so lucky to have had that experience. Uh, during my time there, I learned an immense amount about what monetization actually meant within the software world and how it was evolving and where the opportunities really lived. I worked across a variety of interesting products with amazing teams, and I realized when I was a consultant in that space, I really wanted to continue to understand the way in which businesses were optimizing or working with monetization to to create amazing and great products. And so, that my desire, you know, what I'm really looking for in my career and the impact I'm looking to make is focused on how do we evolve business models to truly be virtuous? And virtuous is, you know, virtue is a big word, right? What does it mean? How does it look? But when I think about it, it's really about making sure value is one-to-one. The customer is getting immense value from what is being created. And internally, the people that are running these companies, the people that are putting their minds together to create something great, also are experiencing the same value. It's a value, value-led journey is what I'm on here.

That's very cool. Let's go back to ProfitWell for a second. I mean, ProfitWell's famous in the world of monetization and, you know, ProfitWell, Price Intelligently, Paddle. Can you, can you talk a little bit about kind of what stands out to you as the key lesson or lessons you learned at that experience?

Yeah, absolutely. During my time at ProfitWell, I had the opportunity to work across a very interesting portfolio. Of clients, um, clients that spanned B2B and B2C, clients that were changing their strategies, really doubling down on what their current strategies were, were extremely confused about what to do and why they hadn't touched their pricing in so long. It really, you know, it was across the board on why people came to ProfitWell to help them. And across all of these different teams that I worked with, the biggest thing that stood out to me was that the teams that had a single center of control when it came to pricing and packaging whether that was within product marketing or at the executive level, were more likely to not implement or move forward with any of the recommendations that we ended up coming with together. And I asked myself, well, why is it that you can't take these recommendations that we vetted in the market that show so much potential that you're so excited about and actually implement them within your product? What it came down to was that single center of control was actually the antithesis of greatness within that company and the ability to monetize more effectively because it didn't allow for complete awareness of how the product was actually built to continue to monetize. So, to break that down even further, right, like what I saw in those single centers of control is that those people oftentimes had a very poor understanding of what the true current state was of their monetization engine, of the operations that surrounded what makes monetization so important and effective within a company. And we spent so much time going through, well, what does the market want? How do you guys think about this? What is your business strategy? Only to get to our current state doesn't support this, or we need to evolve our tech stack to move forward with this. So the biggest lesson that I learned, and what was most interesting, which is what took me down this path of really going into being a tactical operator within the monetization space, was if you don't have a strong grasp on your current state and you don't understand where your opportunity areas are within your current state, or what it takes to evolve the current state of technology, of people, of processes, you can have the greatest strategy in the world built out and thought out, but it's not going to work because your single center of control is keeping people away from contributing to something that requires close collaboration and thought leadership across the board. And that was a profound insight because it makes you think about the way in which businesses are organized.

So, it's one of the more unique answers I've heard on this podcast, and I'll explain why. I think what you're saying is, hey, I'm doing all these consulting engagements to help software companies evolve pricing and packaging and reinvest in these incredibly data-driven analyses of their market, their competition, elasticity, you know, all of the things that make Price Intelligently, Profit Well famous for what they do. And then the company can't implement our recommendations, which is a massive waste. And the reason they couldn't implement most, more often than not, was ownership of the initiative was siloed. Is that a, is that a fair playback?

That's a fair playback. Yeah, siloed and— sorry, it was siloed and it was, um, it was because of its siloed nature, it was always too ambitious in scope. And ambition isn't a, a bad thing, right? It's great to be ambitious, but there's a difference between being ambitious and being impatient. And I think we saw that play out in a lot of different scenarios. And so you create this really ambitious plan that has a lot of potential, but oftentimes impatience takes over and then you just kind of piece it together and continue to to build something that may or may not scale, right, when you get to that point.

And so the danger of that ambition is it lacks a lot of context across other key functions in the business that would have to be stakeholders' dependencies in this work.

Precisely. The order of operations for how to get there is suboptimal, right? You can parallel path a lot of your discovery of what your current state is and understand how you should frame things. But if you think of, if that's an afterthought to the strategy work you've done and you're trying to retrofit your strategy into it, suboptimal, right? And your ambition kind of goes out the window at that point.

Well, one of the things that is so interesting to me about that observation is another observation that I have made, and that I think many people have made on this podcast, is that pricing and packaging often has ambiguous ownership within companies, which makes it difficult to mature as a practice or as a function. But what's interesting about what you're describing is there may have been ownership, but the ownership was in some ways not effective because it was siloed, because it lacked context, because it was ineffective at cross-functional collaboration and practice building.

Yeah, I think that's precisely it. I actually think that this is a hot take, but my belief is that the overemphasis on having a single point of leadership for pricing and packaging is actually going to be very ineffective for companies that need to make large transformations. It's not about having one person that's responsible for coordinating across the board and leading stakeholder engagement and, you know, getting cross-functional buy-in. It's about educating everybody who touches that monetization engine, that system, in what the right approach is is for growing your business. It's about enabling everybody that is a leader, that is tapped in to grow the business, to have that mindset and to have those tools to continue growing. I think having one person do it is a bottleneck, right? Having one person own that, it's collective ownership that is required.

So, okay, so let's go to best practice. I was going to save this question for later, but how does a company mitigate the risk that they set up pricing and make the mistake that you saw regularly at ProfitWell? What's the right way to set up pricing as a practice that can be very successful at a company?

Yeah, this is the loaded question. Best practices, right? Like, are they truly the best practice for everybody? I think one of the first thing you have to ask yourself when you think about how do we set up pricing and packaging is where are we in our growth and what should be our focus today? If you are just getting started and established as a company, you are starting at a very different point than if you are pivoting your entire business strategy to say, go from B2C to a B2B market, or if you're introducing an entirely new product line. And I think the, the foundation, right? What is required for any company that's thinking about what the best practices for how to establish a good monetization system within your organization is, do you, are you fully aligned on what the value of your product is? And now I think there is an overemphasis in the market to be a value-driven product, to do value-based pricing. Um, and that's not true for everybody. Some products do very well being cost-based, right? Others do very well being priced by services, right? And the time spent on those services. And it's unique to every company, but I think the most important thing is when you set the intention for creating a monetization engine, you have to be really real with yourself about what it is that you're delivering and the value that you're offering. Because you can say like, oh, you know, if you're in a super commoditized market, and I know there's like, You know, even if you're a commodity, you can go value-based pricing, sure. But if you're in a super commoditized market and you're trying to inflate your prices based off of, you know, what marketing thinks is the best way to position your product because somebody's convinced you that you're the leader in this marketplace when you're not, you're going to have a much harder time creating an effective monetization system in your product than if you get real with yourself about what it is that you're offering. And that's a hard realization because customers feel it too, right? You can say, oh, we're the number one product on the market and we have all these cool things, and then the customer uses it and they're like, No, it's not, right? Like, it's hard to lie in this world now. We're so— buyers are more knowledgeable than ever. The people creating products and on teams, most, you know, my generation really gives a shit about what they're doing and wants to do the best work that they can. And so, it's really hard to just, I would say, gaslight an organization and customers into thinking that your value's there when it's not. And that really is the foundation of what you build a monetization structure off of, in my belief. If you understand your value, if you know exactly how you're going to deliver that value, right, or if you have an idea, an ambition around that, you can then create your entire monetization structure off of it. And then you start to ask yourself, really, I think what it's fundamentally about is asking yourself critical questions and being really real with yourself as you're figuring it out. There is no one-size-fits-all. Some people, for a period of time, need a very seasoned leader within the world of monetization to come in and help them assess their current state and define what it is that they're looking to do. That's phase 1. Phase 2 is, okay, what we've learned about what our growth mindset is and how we should go about growing, let's make sure that we train all of the leads, all of the managers, all of the people that will be a part of this into this mindset. Let's make sure we codify it into our culture, that it's embedded in the DNA of what we're building. And then we go on to phase 3, right? And that is, You know, we have a new system or process for, you know, launching our products, for getting them to market, for continuously evolving them. Whereas some others, if they're just starting up, right, it's just about making sure that you, you understand where, where you are now and where you want to go and you set up the right course for the people that you have involved. I think going into like the world of consulting and thinking about what Deloitte taught me so much about is like, it's really boils down to people. Processes and technology. And it's that simple, but it's hard because you have to ask yourself the critical questions and be prepared to make shifts when they come, but still hone in on what your value is. If you don't know what your value is, if you don't know what your purpose is, you'll have a really hard time monetizing your product.

That's a great answer. And it makes me curious about why you left consulting to be an operator and what have been the differences. In terms of what it's like to be a consultant around monetization versus being in the trenches and figuring out how to push for these types of best practices, push for this type of self-reflection, push for this clarity of value? What have been the big— how would you riff on the differences between those two worlds?

Yeah, you know, it's interesting. My, you know, I started off at Deloitte in consulting. And I think in the past 10 years, the perception of these large consulting companies has evolved quite a bit. You know, they were seen as industry titans that had all of the expertise in them, and kind of the, the rug has been pulled back, and they're like, you know, maybe they're not, maybe they're not, you know, the experts that we consider them to be, and maybe they're not shaping business the way in which we want them to. Maybe the, the intent fully isn't there. And, you know, when I was working at Deloitte, I, I felt like a fraud. You know, I was working with these great clients, and I felt like I didn't have the the tools, the skills, the knowledge, the know-how to effectively guide them in what they were coming to us for. And when I entered the world of monetization consulting, I, you know, took it upon myself and having great mentors and leaders at that company was empowered to learn as much as I possibly could. And that was like huge. It was a huge learning curve. And I climbed up that learning curve and I learned as much as I could about monetization. But I still realized at the end of the day, because of that big aha moment of the single center of control is what's really, you know, creating inefficiencies and what we're recommending was, I don't know anything and I want to know more, right? And I still don't know a whole lot, right? Like, I'm on a journey of curiosity. That's what's guiding me to where I'm going. And my curiosity of wanting to know how companies were setting up their product operations, how companies were setting up their development cycles, why they were using certain tools over others, how they were tracking their metrics, what was driving their decisions day to day, and how they were really getting to market and how those, all those things connected together really drove my next step into being an operator. Personally, I didn't wanna feel like a fraud. I don't wanna give people advice on how to do something without actually knowing what all of those things could be, or if not knowing, knowing how to ask the right questions and knowing how to slow myself down to ask the right questions. And so, you know, I believe that while I was at ProfitWell, I did amazing work with the clients I had, and I'm so grateful for the opportunities that were presented to me. And, you know, I know that now, years out from ProfitWell and the experiences I've had since then, I know a whole lot more than I did when I was at ProfitWell. And it's allowed me to develop this very growth mindset, this very critical mindset that isn't necessarily based on best practices per se, but is based on critical inquiry that will get me to whatever the best practice needs to be in that environment. So yeah.

You know, I've interviewed a couple people that have gone from consulting into operating and not necessarily in the context of monetization specifically, but consulting to operating. And I wonder if you, is it true that one of the primary differences becomes when I, when I am a consultant, I make a recommendation and that's largely where I stop. Whereas if I'm an operator, I don't stop at the recommendation. I have to persuade, negotiate, influence towards actioning the recommendation, compromising with the recommendation. Can you talk a little bit about what that experience has been like for you?

Yeah, absolutely. I mean, you're spot on there. I would say that being a consultant is a very fun thing to do. And I think that it is, it's exciting, right? It requires a mindset of curiosity and, um, and storytelling that is extremely important when you are an operator, right? But when you're an operator, you know, your strategy may sound fantastic and it may have all this market research behind it, but the reality is you are then working with other functions who may or may have not been brought along for this entire journey of creating the strategy to then tell them the story of why it's so impactful to them. You really bring in a deeper level of what I'm going to say is emotional intelligence, right? When it comes to implementing the strategies that you're offering and tactical know-how, it gets much more complicated when you bring it in internally. And this is oftentimes where, you know, I think we talk strategy, what's the strategic approach we can take without fully understanding what the current state is, right? Of how we can implement it. You bring your strategy forward and, you know, somebody who has deep technical expertise in one small component of what your strategy's gonna entail rips it apart because it's not gonna work. And then you have to pivot and you have to go through this. So, I think for me, and this has been my experience in going from a deeply strategic role to a very tactical operational role, it's a very hard skill to develop and something that I'm definitely not perfect in yet and that I'm working through, you know, by, you know, taking on deep reflection of myself and how these projects are going and making sure that I'm, I have the right touchpoints as these projects go on. But it's incredibly difficult to strike the balance of how you bring in strategy into an operational context and actually get it to delivery. And seasoned professionals, they've got it down packed. I'm still new in my career and I'm trying to help lead these efforts and initiatives. And so, it takes a lot of learning. It requires that you're willing to compromise and that you're willing to disagree and commit to stuff when it comes down to the brass tacks of how you're going to implement it. But it also requires that you have to never stop learning about how to be a better collaborator, a better, um, a better colleague, a better person when it comes to doing this work. It's, it's difficult. I think strategy is very fun. Consulting is very fun. Operations is also very fun, but a totally different beast.

Has there been a moment in this shift from consultant to operator where you felt like, oh, I fell on my face there, and yeah, learn from it? Can you, can you tell that story if one comes to mind?

Yeah, so many times. Um, and I think that is really— those moments of failure, those moments of realizing, oh crap, there was a way better way to go about this, have been the most influential and formative moments of my career. It hasn't been the successes, right? Those are awesome. You know, you launch something, it goes off without a hitch, there's no incidents, metrics are looking great. Like, that's cool. But truly the most influential informative moments have been those failures. And those failures have come from, you know, I think about the way I need to work. My best work comes from moments of calmness. If I'm able to find calmness in my life and take the time to slow my brain down, I get to my biggest aha moments. And when I succumb to the pressures of external forces, whether they're on my team or the environment that I'm in, I oftentimes have to use an immense amount of willpower to get to delivering whatever it is that I'm doing. And I found that in, you know, from delivering a strategy to actually delivering, you know, the, uh, you know, like launching a product and getting to the tactical parts of it. My biggest failures have come from, um, not allowing myself to level out and fully take into consideration all of the things that are going to play into it. And it, I feel it as a failure because oftentimes it makes my colleagues have to compromise on what they're doing, right? Because we're under these rush, you know, these time pressures, because we need to hit these goals, because we've set these timelines for ourselves. I don't approach it correctly, um, you know, I, I find that I haven't approached things correctly. I've learned, I've evolved, I've taken a different approach. There have been moments where I allowed myself to feel too much of the pressure and not have that clarity, which has resulted in Having my colleagues have to overcompromise on what they're doing to get something to delivery quicker, or, you know, getting something there and then having to do a series of fast follows that totally detract from whatever was next on our roadmap. And that's really hard, right? But that also speaks to the way things ladder down and how they come into, you know, the space of monetization to take forward. When you're dealing with money, there's always pressure, right? So there's really, there's no way to escape it. It's just how do you create a space for yourself in the pressure chamber to do your best work?

It reminds me of a story. There's a, you may know him, his name's David Kaufman. He is running pricing and monetization at Docker. And yeah, he had come from Simon Kucher and, um, I asked him a similar question, like, was there a moment where you felt like you fell on your face? And he was like, well, it was the time when I kind of told the engineers what our strategy needed to be. And I hadn't really figured out, you know, what was kind of the reality within the context of how pricing worked within, within the codebase. And it was a real fall-on-my-face moment. And what he did subsequently is he kind of created two different pricing committees, effectively. One was the executive pricing committee and the other was the operational pricing committee that had to have the context first and foremost, well before the executive committee. I thought it was fascinating.

That's a lesson I've also learned and have seen, especially in my, my current role where, you know, we're, we've gone from being a B2C to a B2B company and there's, you know, shifts in how we're approaching our target market. Pushing a strategy on the engineering team that has not been thought of in the current state and what is possible can create a lot of technical debt because engineers will tell you, we can do anything and they can, they're brilliant. They can truly do anything. But do you want them to do anything? No, right? Like, do you want them to approach it in a way that is not going to make, you know, future growth impossible because they built it in one way versus another way? And both those builds were equally feasible. We just didn't direct them properly. And that's, I think, part of not necessarily knowing the depth of what the current state is and the complexity behind it. One small direction without clear insight can lead to catastrophic failure in the future. That's terrifying.

Take us into Dashlane. So you joined this company, what, about a year, year and a half ago?

Not even, earlier this year in February.

Okay. So tell us, tell us what attracted you to the company and, and kind of what the charter, what the charter and the mandate was when you joined the business.

Yeah, absolutely. So, you know, I spent a year at Seismic within product marketing, and during my time there, I learned a lot about the close connection and the importance of having product guide go-to-market, but having go-to-market helps set, set like kind of rails for product to create within. And that was a really interesting realization to me. Again, going from just being a consultant and strategist really to getting into the operational world was how product is built and the work that's put into it really can make or break successful go-to-market, go-to-market, right, efforts and also make or break successful monetization efforts. You can only paper skew or bandaid things together so much. Much before you reach a level where you can't scale any further. And so, what I was really looking for after spending time at, at Seismic was a role where I could get really into the weeds when it came to how a product was built and what the monetization engine needed to be. And the mandate at Dashlane when I joined was, we need somebody who has experience with pricing and packaging strategy, understands the different approaches you can take when it comes to how to grow your product and what it means to go to market. But We also need somebody who has technical curiosity to help us determine the levers we need to pull and what we need to clean up to continue growing within this B2B space. Dashlane is a credential management product, and credential management products are, you know, I used this word before, but they're a commodity now, right? Like our phones have a credential management app on them. Apple announced theirs not too long ago. Google Chrome has one built into its browser, right? And Dashlane transcends all of these point solutions that we have and creates a comprehensive tool that secures things that are so vulnerable to, you know, hackers today. And to me, Dashlane is a product that provides an immense amount of value. If we can secure your data and help you ensure that you have safety in that, that makes sure that we mitigate a ton of risk in your life. Right. And so, Dashlane has this incredibly important role within the market, but it's also one that, and to be very blunt, like, is very, can be overlooked by businesses as being something that's, oh, you know, this is just an afterthought, a compliance box that we need to check. And so, I joined to really help Dashlane figure out what are the changes we need to make within the fabric of our business to continue to grow within this B2B space while still honoring and serving and really protecting our consumers. Right, and the product that we're offering them, especially as the market provides them with more and more point solution options that may not meet their needs in the future.

Yeah, it's, I mean, it's a fascinating challenge. If I'm hearing correctly, it sounds like we're, we're in the midst of a material evolution in the business from B2C to B2B that will require a material evolution in how we think about pricing, packaging, monetization that will further require a material evolution in how our systems support said evolution. And the businesses, I think, you know, it's a meaningfully sized business. It's a growth stage software business. So there's real history from a systems perspective. And can you talk a little bit about like what have been maybe the biggest surprises or where your energy has been most focused and most drawn to within the first year?

Yeah. You know, you framed it perfectly. There is a lot of history in these systems and with history comes debt, right? And how you build and how you want to grow. I think it, if we think about why was Dashlane created, what was its purpose, what value was it looking to deliver? Dashlane was created for the consumer, right? It was created for you and me to have password management on our devices and make sure that our credentials, our notes, our information was secure. And when we go to input it somewhere, it can easily be there for us, right? And we don't need to go looking for it. Scaling from a consumer to a business where you go from an individual to an entire team, requires a very different setup in how you think about monetization. I think because of the type of tool we are, you inherently think about, okay, credential management, price by user, right? It's about the amount of users that are accessing it. But then you think about, okay, in a business environment, we now have, you know, most of the tools that we use have SSO. So, we actually don't have a password to access them. Oh, there's passkeys, right? I don't need to remember anything to get into this. Tool, you know, I signed in once, I'm never going to have to sign in again because my computer is going to keep re-authenticating me being here. And so you think about A, what is the strategy behind how you're pricing and does it still hold? And then you think about B, how do we, how do we adjust? And because we were built on this, this mission around the individual user, our systems kept on with that. And because we were built by a brilliant team of engineers who were so lucky to still have a variety of the founding engineers that have been on the team since Dashlane's inception, a lot of the technology stack was built by them and is maintained by them. And it's incredible to see what they've created. But Dashlane entered before Stripe, before Zora, before Chargebee, before all of these massive payment billing system providers were truly established to help companies think about subscription management, think about feature entitlements, think about billing and payment processing. And so, as we evolved from just being B2C where everything was simple, one account to one user, flat price, right? To now evolving to one account, hundreds of users, thousands of users, different levers, different features. Our system has been pieced together to fuel the growth in our e-commerce avenues and our sales avenues, but it hasn't been tuned to actually scale that growth effectively. And so we're able to do a lot because we have brilliant people. But again, going down to the people, processes, technologies aspect, the technology aspect of it does need a strong refresh. And so a majority of what I've been focusing on this past year has been what is the technology we're using? How does it match up to our strategy or how doesn't it? And if we're still refining and thinking and learning and testing when it comes to what is the right strategy as we look to go deeper into the B2B world, then what do I need to be prepared for, right? And how can I prioritize things once they come to us? You know, I really have taken less of a strategic role within my current, you know, my current function at Dashlane. And it's really been about creating the right processes, the right structures, and assessing our technology in a way that ensures that our team is doing valuable work, and they feel as though the work they're doing is important. And that translates directly to the customer and how they're valuing and of using the product. And it's, it's a tough balance.

Yeah, you're going in, you're going into the belly of the beast, like you're really deep into the mechanics of pricing and packaging, like the architecture of pricing and packaging in B2B SaaS. And, you know, it's apparent to me that for a successful B2B SaaS company, pricing and packaging ends up often governed by multiple big complex systems, systems in the sales stack, like the CRM system, the quoting tool systems, and the billing or finance stack, like the billing system, the subscription management system, the ERP, and then systems in the product stack, like your feature flagging products, how you're going to think about building metering. There's a lot. And I'm curious the extent to which you've begun to develop a philosophy or a point of view on an architectural standard that you think would give companies the type of flexibility that, you know, you're probably kind of running into issues with?

Yeah, that's, that's a great question. You know, I've been deeply focused on the potential and opportunities within Dashlane at this moment. And again, you know, our product was built by brilliant engineers, therefore our billing systems were also built by those brilliant engineers. And at this moment, thinking about the type of product we're offering, the potential for our growth, where we can start to pull certain levers— Dashlane is not an overly complex product in the same way that a lot of information security products are, are complex, right? We're not anywhere comparable to a lot of the, a lot of the complex tools that you see within, within B2B SaaS, right? Like, you know, what comes to my mind is observability tools— very complex, lots of consumption models, right? You mentioned Docker. Docker systems, extremely complex, lots of different models. They've also just changed their pricing structure and strategy. They're thinking through how are we going to build our engine, right, when it comes to, um, you know, this evolution within our structure. We have the luxury at this moment of knowing where we can start to pull different metering levers, where we can start to pull different feature differentiation levers to really create more robust and targeted offerings. But we also have the luxury of being simple in a lot of ways. And so, with a simple product, right? And I'm not— not to discount the product at all. What our engineers do to create the secure product we have is not simple. But when I think about when you perceive this product and when you look at it, when you're making a purchase, it doesn't require a huge cognitive load for you to say, "Oh, I understand what this product is doing," right? You don't need to be a deep expert in credential management to know what Dashlane does for you. It's a fairly simple story that it tells. We don't need to be billing experts, right? We don't need to manage our own billing systems and create complex, flexible systems. We need to understand and define what our guardrails are. And who we want to be and how we want to continue to grow. And then we need to be comfortable with getting rid of the responsibilities that other people do for their jobs, right? Like billing is an entire job in and of itself. Stripe does a great job at billing and payments. Zora does a great job. You know, Paddle does a great job. These companies were created to do that for you. And so, as you get an understanding of, okay, we know that these are levers we can pull either now or in the future. The question becomes, should we continue to build this in-house and support it, or where do we start to outsource? And it's not about just flipping a switch and getting everything out. It's about understanding with your growth strategy, with your approach, where can we start to transition things over and start to take things away so we don't have to build them on our own, right? And where are we comfortable with maybe spending a little bit more time on, you know, bringing the data connection points together and ensuring we have visibility. Versus having, you know, 4 or 5 engineers just work on tax compliance or making sure that the entitlements weren't coded incorrectly and that we don't have any incidents, right? Like having your entitlements in your billing system is not ideal, right? It is not ideal to have those two things built on one system and done together. It is not ideal to have to manage and build out your own user interface for your sales and CSM teams to interact with, right? That all becomes huge technical debt that when you want to grow, you then have to consider and have to scope into a project that may have taken 2 weeks to implement, but now will take, you know, 3 months because you have to take on all of the debt that you've created historically to get to that next phase.

Right. You know, one of the things that's so interesting about this experience is, I mean, this isn't a startup that was founded 2 years ago and elected to build their own billing system. This is an older software company. That decided to build a homegrown billing system prior to the tools that you mentioned being on the market or being like pervasively understood and on the market. And I imagine that part of your challenge is how do I communicate to different audiences, executive audiences, as well as product and engineering audiences? We need to move away from a homegrown system. We need to outsource these types of systems. They're not core to our product. I imagine that's part of your challenge. It's part of the challenge of the role that you're in. And I'm curious what you've learned about communicating effectively and successfully to two discrete audiences with often with different language sets.

Yeah. You know, this is part of, part of my learning journey right now is, is how to effectively do that. I've faced moments where I've said one thing and I haven't been clear enough, and then it's taken us down an entirely different route. And we've, you know, dug into a conversation that we just didn't need to have because I said the incorrect thing or I didn't use the right term. Being a product manager, there's so much around like code switching and language and how you're communicating things. Like you have to be a master of communication, which for me, if I'm not calm, I'm not a master of communication. Like I know this about myself and I'm learning how to find calmness in my day to day, right? Like it's hard, point, like period. It's hard. And you know what I found and what's most effective to me is first I need to know what the hell I'm talking about. If I don't have all the context and information, I'm not going to be a good communicator. I also need to know exactly where are my stakeholders' heads at? What's on their mind? What have they been dealing with? What is their priority? And shift my narrative to what is top of mind for them to make sure that it's important. You know, when I speak to engineering, engineering really thinks about security, right? We're, we're a security tool or credential management tool. Everything that we push forward on needs to be from the lens of security, even if it isn't necessarily a security-first thing that we're doing. It has to be from that perspective. Whereas at the executive level, when you're talking to those that are, you know, really driving our pricing and packaging strategy right now, it's revenue, it's cost, it's thinking about value, it's understanding the long term, it's understanding, you know, everybody's heads are here. Okay, let's start here and make sure we address their immediate goal. But then also let me sprinkle in, and maybe not in this first conversation, but let me start to sprinkle in how this will enable us in a year, 2 years, 3 years out. So the balance between what is right now, and what are we setting ourselves up for later has been very challenging because so much of this environment that we're in is, and that you see this across all companies, is that the balance between ambition and impatience, and those two things blur very quickly. Yeah.

And those two things often also make it hard to be calm too, I would imagine.

Totally.

This has been such a fun conversation. I'm curious to, you know, one of the closing questions I always love to ask is, And you, you've mentioned this a little bit, you've touched on it, but is there a single moment that you feel is truly most formative for you in your career? It was like an inflection point in some ways.

Yeah, I think the biggest inflection point came when I was at, at ProfitWell, and it was after spending months with a client developing a brilliant strategy. Like, we nailed it, only for them to come back to me to be like, hey, you know, we missed all of these vital questions on how it could actually be implemented and then how we could operationalize it. And so, we can't do any of this. And it was like a stab to the heart because we felt so good about this strategy. It was future-proof. It was bulletproof in the current environment. And it was so value-driven, only to be told that we didn't do enough work to consider the implementation operational aspects. And that was the big aha moment of, I don't know anything. I need to get really deep into the operational of this because if I'm on this mission, right, to better the world of work by creating more virtuous operations within software, which will always be here, whether it is the way in which we experience it now or evolves into something totally different, this concept of interacting with products that are not actually here, but have so much impact on how we do things and the value we receive, I need to understand how things are working now, how they're evolving. And what will or will not succeed in the future from a deep operational level. Otherwise, I'm not going to accomplish my mission. So, it's a lifelong mission I'm on here. And that was my big, oh my God moment. I don't know what I'm doing. I need to get much more knowledgeable.

It's such a good story and it's so resonant for me. And I can't remember if I've told you this, but you know, one of the reasons that story is quite close to home for me, because one of the reasons I started Schematic was at my last company, we were our CMO and I were looking at bringing in Price Intelligently. And we ultimately concluded we could not action the recommendation that Price Intelligently would provide to us, even if we had it. And that set off my own curious journey into why it's so hard to evolve this so powerful lever on how value is created. So thank you for that story. Where can people learn more about you, learn more about Dashlane?

Yeah. Um, well, and thank you for sharing your story too. And when we first spoke, you shared a bit about, you know, your journey and it made me really excited to talk about my life and my journey with you and hear more about yours. So, so thanks a lot. People can find me on LinkedIn for now. I am planning on releasing a Substack with my ramblings and thoughts. So keep an eye out for that in the future, but LinkedIn is the best place to look for me.

Awesome. And Dashlane?

And at Dashlane, my email?

No, Dashlane.com.

Dashlane.com. Yeah. You can reach out to me on Dashlane.com. Get out, get in touch with us. Our customer success is awesome. Or you can reach out directly to us via our contact sales forms.

Alexa, thank you so much. So much fun.

Thanks, Fynn. I appreciate it. This is great.