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Meet Santiago Cardona, a seasoned product leader with over ten years of experience in AI, ML, FinTech, Healthcare, and HR/Payroll tech. Currently, Santiago is the Director of Product Management at Fingercheck, leading teams that craft top-notch applications for small businesses. Fingercheck transforms small business internal processes with AI and automation technology, boasting 100K active users daily.

In this episode, Santiago thoroughly discusses how to build an effective product strategy in times of uncertainty. He also shares his view on product roadmaps and frameworks, and common misconceptions around them that increase friction.

As a bonus, you’ll get advice on books to read to improve your tactical and strategic skills as a product manager.

Santiago's background

Santiago Cardona, Fingercheck

The transition from analyst to product leader

Ana Mydryk, Head of Product Management and Business Analysis at Cieden: Hi Santiago. I'm really curious to talk about different practical questions with you.

Santiago, Director of Product Management at Fingercheck: Thank you. Thanks for having me today.

Ana: Your background resonates with me a lot. You started as a business analyst, and system analyst, progressed to product management, and now you're a director of product management. What has changed or shifted in your mindset when you progressed from BA to PM?

Santiago: Yeah, so a lot. You often hear the term, I fell into product management, not that I set that as my goal or career objective. Most people end up falling into these roles and that was the case for me dating back to when I was a systems analyst. I started getting a lot of interest in the technology sector, but I always liked to be at the intersection of many different things. And that's how I kind of fell into the product.

Ana: And currently you're a director of product management. Do you manage different lines of ecosystems or do you manage other product managers?

Santiago: Yeah, so director roles vary depending on the stage of the organization. For FingerCheck, yeah, as a director of product, I manage the product team, product managers, and product designers, and you indirectly manage the engineering team as well. It's like leading without the authority type of concept.

Ana: And in terms of responsibility, do you manage the entire product and direction strategy or do you also dive into details sometimes?

Santiago: So my role is strategic and tactical as well. So it dwells into a lot of things. Going back to the stage where we're at. So we're in a high-growth stage at FingerCheck. We're experiencing tremendous growth. At this stage, you have to be strategic, setting the vision, the direction for the product team, the things that we're going to work on, what we build, and the problems that we're going to solve for our customers. But also, write the requirements sometimes and I have to test sometimes. Whatever we need to do to get the job done.

Ana: Right, yeah, product managers are multi-tools. They need to be able to fill in the gaps anywhere regardless of what needs to be done. 

The challenges of building an effective product strategy

b2b saas product strategy

Ana: As you mentioned, you're responsible for product strategy and roadmap. And I think that's a tough thing to do. There's so much to unpack here. Maybe let's start with why it is so hard.

Santiago: A very common misconception in product management is they believe that there is only one right way to do things. Like here's the right way to build products. So it often stems from an understanding that if somebody implemented a particular methodology or framework successfully, then they can do this, too. And then now we just assume that there is this universal formula for success, like the one-size-fits-all approach, but that's not it at all. So I would say that a good strategy starts with a good, compelling vision for the company. And this is the foundation for an effective product strategy to be in place. Like, where are you going as a company? What is the future that you're trying to create? What is your north star? And that's truly what's going to guide your decision-making and being able to articulate where you're heading as an organization in the long term. So once that vision is established, then there's a series of activities that you must do, right? You know, gather the user feedback whether that is qualitative or quantitative. You've got to analyze the data, and speak with your customers to understand their pain points directly, right? Understand the market and the competitive landscape. And from there, you're going to come up with a series of bets.

Ana: These are our kind of guesses about predictions or our assumptions that we need to come up with. And actually, because everyone says we need to be data-driven and make educated decisions. But in this agile and versatile world, it's really hard to get all the data at once.

Santiago: Yeah. So if somebody tells you that there isn't any gut feeling associated with it, they're probably lying. There is. You're always using your gut and your instincts. Of course, from prior experiences, you're using informed decision-making, right? Not only data-driven but data-informed, right? In the digital world, we never suffer from a lack of information, but it's the overwhelming, vast amount of information that is available. But what's going to dictate your success is your ability to analyze and funnel all that information, throw away what is not relevant, and what doesn't work, and move forward with that. So it's more of a mindset, learning and adapting, right? So. In terms of what we do in Fingercheck, we always try to do experimentation like testing hypotheses on a small scale, even if it's just with a small focus group of people before you commit resources. That way you are de-risking your strategy, right? And creating feedback loops, right? Continuously gather feedback from users, and stakeholders, and truly understand what's working, what's not, and being agile, right? Inspect, and adapt your strategy based on your learnings. This is truly the agile approach. And if you need to pivot, then you should be able to do that. That's why I'm not a fan of religiously following a framework or a methodology because that deviates from the basis and the core of Agile.

Ana: Don't you feel that you're building the plane on the go, on the flight? 

Santiago: You have to stay true to yourself, to what you set out to be your strategy. So you have to create, You have to understand what you are as an organization, right? So, what it comes down to, in my opinion, is focus. Your ability to focus. I love a phrase by Steve Jobs where he says that focus doesn't mean saying yes to a lot of things. It truly means saying no to a thousand things. And he goes on to say that he's more proud of the things that he said no to than the ones that he's said yes to. So if you have an ideal customer profile, you have a target market, stay loyal to that and remain focused. And that's how you can mitigate the risks.
Steve Jobs on focus in product management

Balancing long-term goals with rapid market shifts

Ana: That's a great insight. Yeah. And in terms of creating this strategy, how do you think what is the horizon for planning is reasonable in the current situation? Because of those latest technical advancements, I'm sure that a lot of strategies were messed up and companies are now not sure in which direction to go because they planned to introduce some new features which are not now relevant to the market. 

Santiago: This goes back to a really good book that I read too. It's called Playing to Win. Get clear on your strategy as an organization. So that truly defines what is the purpose of your organization, what they call in the book is what is your winning aspiration. Where are you going to play? Like what is the market, the geography? Are you staying national? Are you going global? What are the boundaries of your playing field, right? As soon as you start going through it, it could be as simple as grabbing a simple Google document and starting to write these things down. And you follow that order, right? And then after you lay down where you're going to play? Now you start focusing on, okay, how are you going to win? How are you going to achieve your winning aspiration? You choose a playing field, you identify value propositions. Now, how are you going to accomplish those things? And that's where you start coming out with a strategy. And then, what are the systems or capabilities that I need to put in place? Well, here are the things that we need to do as an organization. For example, we want to win more customers. If our target segment is the SMB, what are the things that you need to do to support a larger customer? An enterprise, for example. It involves setting up structures different processes, and metrics as part of that strategy, but getting clear on the first winning aspiration. That's what truly is going to define the rest of the initiative that you need to do.

Frameworks for navigating changes

Ana: And do you know any frameworks that can connect this like strategic vision?

Santiago: What I would say is that it always goes back to your culture because driving change is hard. And that's one of my learnings in my experience. Driving change is hard. You can come, that's why I'm not a fan of following religiously a particular framework or methodology, because you can just adapt that to any organization. Every company has a different set of challenges that you need to adapt to and different mentalities. What I do in FingerCheck, we focus on outcomes rather than outputs. And then we find meaningful ways of measuring the impact on users and business. And for that, we have a ton of metrics. If you want to measure engagement, you have ways of doing that, daily active users, and monthly active users, by getting clear on outcomes, telling a story, and keeping the customer at the center of whatever you're doing. Framing that in terms of customer needs and the benefits of what you're going to do. And then regularly review and adapt. Don't stay too loyal or religiously follow a specific framework. Use what works for your specific organization at that moment in time. Because what works for you, when you are in a startup stage, it's not going to work for you when you're in a high growth stage or when you become an enterprise. It's completely different. So know where you are as an organization in terms of this new stage.

Resource allocation in product teams

Ana: Also, an interesting question about what percentage of a team's effort should be dedicated to working on strategy.

Santiago: I believe that strategy must be done by the leadership or the organization. And then once that's established and in place, each team in your company should have their OKRs, their objectives as a team. You give them problems to solve. So based on that, you place your bets, right? Are you looking for the quick wins, the low-hanging fruit, the lighters, what I call them? Are you looking to create customer delight or are you looking to disrupt the market with this innovative initiative or solution, but that you know that's going to take up a lot of your resources and time? So based on your objective as an organization, you have to determine your resource allocation. But what I always do is, I always reserve some type of resource and capacity to support our customer base. And that needs to be in place at the outset of every initiative. We always reserve about 20% capacity for bug fixing or more what I call the delighters, like low-effort, high-value customer feature requests that we could accomplish and satisfy our customer base. 

Why high-level roadmaps?

high-level roadmap
This product roadmap example was borrowed from

Ana: What is your opinion about road maps?

Santiago: After having made a ton of mistakes, I've done pretty much all the types of roadmaps that you can do. I've done the spreadsheet. I've used the feature-driven roadmap. I've done the quarterly roadmap. I've done just so many. Honestly, in my experience from what I've learned is that the product roadmap should be very simple and high-level because if you have a feature-based roadmap that is focused on outputs, like here are the many features that we're going to accomplish in Q1, Q2, Q3, that doesn't communicate your strategy. And it shows a lack of strategy, I would dare to say because a set of features does not reflect that you're working on the outcome. Like what is it that you're going to solve for your customers? Like what kind of they're having, right? I always emphasize the importance of flexibility and iteration. So roadmaps don't have to be set in stone. I like the now, next, later type of roadmap, but keeping it high level because that reflects our strategic objectives, right? We want to increase… Get into a new market or increase user engagement on a specific product or product line Those are high level and then what are the set of? Task or initiative that you need to do to accomplish that goal and that's how we do it but it also helps with your organizational alignment and stakeholder management because when different stakeholders across the organization see something all right, well you have this in Q3 and here are the set of things that you said you were going to do in Q3. That's not realistic because, in the product, we all understand that you don't know when you're going to, you can have hard deadlines like that until you truly get into the weeds. You understand the product requirements. You understand the tactical implementation, and the scope, not only from a development standpoint, but also the testing scope. You go to market strategy. All these things are going to yield a different date line from what you had originally perhaps laid out in a roadmap document. So that's not realistic. And it doesn't communicate the progress and the alignment that you want as a product manager.

Ana: Yeah, I like this concept of like three buckets and it makes our roadmaps more versatile and it can be communicated to different stakeholders and there are no commitments. Like you can communicate to sales or customer support that we will have these features coming up but we'll see when we'll be delivering them. That's because roadmaps are tools to communicate and align the team across different stakeholders. 

How to achieve organizational alignment

Ana: Actually, a good thing we haven't discussed is how you align stakeholders around the vision.

Santiago: So it all comes down to communication and often over-communication. That's something that I've learned the hard way, making mistakes. But, if you want to drive that organizational alignment, you have to communicate and over-communicate sometimes. And even at the granular individual initiative project level, you want to tie it back to your overarching objectives as an organization. Even if it's a smaller project that you're working on, always tie it back to your vision, your mission, and your organizational objectives because truly everything that you're doing must follow your objectives, right? And that's how you create that alignment. And I often use storytelling. I love sharing customer stories and pain points. I make it a point to speak with a few customers every week. I honestly can tell you: you can't be successful in product management if you don't speak with customers directly. And I can tell you how many times I spoke with product folks at other organizations and you ask them how often you speak with the customer. Yeah, often. Well, when was the last time you spoke with the customer? Last month or I don't know, you know, it's like wow. I just don't understand it. I make it a point to speak with customers so I can understand that feedback pain points directly but what that also helps me is to bring that back to my teams and say, hey, I was speaking with these customers. They're having a really tough time with this specific process or managing the workforce in this specific scenario. And here's how we think we could help them. And here's what success will look like for us. So you always try to tell a story, tie it back to the customer, and highlight the pain point. Then you highlight the pain point and the benefits of the initiative that you're about to undertake. And then everything trickles down. It creates that alignment. It creates that rapport with your teams and your motivation. If you don't share the vision of what you're doing, if you don't share the why you're doing things, then it just becomes what we know as creating a team of mercenaries. It's a harsh term, but it's just focusing on task completion. But really, you want to highlight that the work that we do is meaningful and that is changing the lives of customers, which is what we're all about here at FingerCheck.

Ana: Yeah, that's great advice. I think that we need to circle back all the time and share as much information about customers as we get and have this constant loop and contact with actual customers. That's great. 

Product strategy and design

Ana: I would also like to discuss a question about the role of the design in the product strategy because as in the current setup, design is getting more and more important because people are getting used to working with some patterns, and product strategy is multi-layered. There could be aspects of design strategy or tech strategy. How do you align these strategies in one product strategy?

Santiago: Absolutely. So I believe in empowering teams by giving them autonomy to solve problems. With this, you can foster a culture of innovation and agility. And then once you do that, you also have the accountability that goes with that. For example, at FingerCheck, our product design team owns usability. They own the user experience piece. They own the research. They own the piece of the initiative to make sure that whatever solution we're implementing at that point, is truly user-friendly, and that it has a great user experience that is simple, and intuitive, but they own that piece. From a product standpoint, I would like to make sure that what we're working on is valuable, and that it makes sense for us as an organization to invest in that particular initiative. And then the engineering team will decide whether that's something that is the technical implementation if it's feasible for the organization, and whether we have the technology and the infrastructure to support that user experience. So having clear alignment, responsibility, and accountability on each specific product initiative, honestly fosters a collaborative environment. And that's how we manage it.

How FingerCheck tracks product design metrics

Ana: Thumbs up to your design team. I've checked G2 reviews and people comment on the use of use as one of the top pros of your system. So do you measure usability at FingerCheck? Do you track design metrics or UX metrics? Because you mentioned that you keep track of product metrics, but do you specifically measure usability?

Santiago: Again, we're at a growth stage, so we don't have a ton of resources because we're making investments in other areas. But yeah, we track NPS scores because that only tells you the satisfaction from a customer service standpoint, but it also can give you hints about the user experience from a product standpoint. We also track monthly active users, and daily active users for user engagement and we also track feature adoption what I wanna understand, and I partnered with my design team, is we wanna understand where our customers are getting value from our product. What are those features, and modules that they find most useful, right? Where they're getting their value from? So yeah, we do have some product analytics in place. And that's honestly, that's how I start my day. So I start planning out my day on Sunday nights, and Monday mornings. The first thing that I do is open our dashboard for analytics. And I start looking for trends. I start looking for insights But always with a goal in mind, right? I understand we've rolled out a specific feature and focused on product optimization for a specific feature set. So I want to understand what's the usage. What is the customer feedback and do we also create those channels for feedback? Surveys and we also have a channel for direct customer feedback on a per-module basis that gives us great insights as to how we're handling the features in terms of value and usability.

Collaborative design for thoughtful solutions

Ana: I know that there are two types of product managers. Some are very, have meticulous attention to detail when giving feedback to designers, especially, and others can entrust design decisions totally to the design team, to which they belong. So do you provide direction into design decisions as well, or do designers make those decisions on their end?

Santiago: If we're working on a particular initiative, I own whether that's valuable. So I need to explain to my team why we're doing it, why we are investing in a particular solution, right? And then from my user experience standpoint, yeah, I always, bring mock-ups, I love working sessions, and I tell them what I think would be good. The feedback that I've gotten from my design team is that they appreciate that because not only do I bring the why, I bring the customer story, I bring the benefits of what success will look like if we were to implement a particular solution and then I give them my idea and it could be just like a paper napkin sketch and they just turn that into an amazing design but I just let them run with that but giving them something to work off of often has proven successful for us in my experience. And I've gotten positive feedback as opposed to not bringing anything to the table. Now, that's not to say that I'm going to drive the design process. So I wouldn't get into that. They are the experts in their fields. And that's why we have a product design team, right? But it's a collaborative approach. And I enjoy that a lot.

Ana: Mm-hmm. Yeah, that's great because the picture is worth a thousand words and it's better to show it I think that it'll be something like that and they can pick up and have this input sometimes they're really good. 

How product teams can use AI to speed up handoffs

Ana: All right and one last kind of question will be about adapting to change because I've checked those recent updates from Microsoft, Google, and OpenAI about all those amazing things that they plan and everyone predicts that in a few years, maybe even faster, AI will soon create code by itself. SaaS positioning could be undermined because of that because you can create a custom solution for you at a low cost. How do you sleep at night, especially with those updates coming very, very fast? So how do you adapt to these changes?

Santiago: So I've always maintained a continuous learning mindset. I think I consider myself a lifelong learner. So I love learning new things every day. And I'm humble enough to say that I don't know enough, right? I don't think AI is a threat, especially in the product community. I think that's going to enhance our productivity. For example, with the emergence of no-code tools for products, we gain a lot.

Going back to my time as a business analyst and assistant analyst, I was required to know SQL and to understand how to create user queries, generate particular reports, and all that. So I had to learn that. And honestly, it's not that easy to learn SQL language, right? But now with AI, you can turn natural language into a SQL query easily. So you're not relying on engineering anymore to run a query, for example. So that's enabling product managers and product folks to get, gather those insights, get those analytics that they need without the unnecessary feedback loops and delays by relying on their engineering team. Also, there is the emergence of rapid prototyping.

As for AI in UX trend, I was using the UX tool the other day. With this AI-powered tool, you can generate mock-ups and low-fidelity wireframes with natural language. Like generating a FinTech app for payment processing, for example, and it gives you a really good wireframe so that you can start working off of that. So for rapid testing and rapid prototyping, I see that as an enhancement to our productivity. And for developers, they can troubleshoot and debug code and enhance their code by leveraging AI as well. So I think I see that as an enhancement to our productivity, not as much as a threat.

AI UX trends

Staying informed and motivated in product management

Ana: And how do you keep yourself up to date? Because you mentioned you're learning about some tools. Do you check the net every day?

Santiago: Absolutely. So there's just so much information out there and that is free and readily available. For example, this podcast, it's a great example. So I often subscribe to newsletters and forums. I tend to attend networking events. I love reading, so I'm always on the hunt for that next good book. And yeah, podcasts, LinkedIn is a great resource to network with like-minded individuals. There are special communities that are based on your interests, right? If you're interested in AI, there are just so many forums, channels, and newsletters out there. And I am now one that I like a lot is TLDR. So yeah, that gives you a really basic breakdown of what's going on in the world of product, web, design, tech, investments, startups, whatever it is that you want to learn about the information there, you just have to be intentional about what you're doing.

Ana: And maybe in wrapping up this conversation, I think that being a product manager is a very stressful role because you have a high level of responsibility. How do you keep yourself motivated?

Santiago: I've had conversations with my team and friends in the product world and I tell them about product management, especially for those people who want to break into product management. I tell them this is not a nine-to-five, 40-hour-a-week job. It's not. Let's be honest and be realistic. The amount of work that you do from a product standpoint, it's a lot. You have to know a little bit about multiple disciplines and that takes time, right? So depending on where you are in your career journey, you decide where you want to focus, on your strengths, mastering your strengths, or you want to focus on those weaknesses. But that's putting that out there and second staying motivated. It's just making sure that you're working on a product in a company that motivates you to be passionate about the things that you're doing. So I'm passionate about improving the lives of small businesses because they are the backbone of the economy. I think small, you know, I come from a background of small businesses. My family has small businesses. So I'm just genuinely passionate about small businesses. So find something that you're passionate about. That way you're not your days are in drag. You see new challenges as new opportunities and you get excited about those opportunities and then. No, when you need to take a break because product burnout is real. It's real and I've seen that especially in more senior roles once you get to a certain level of product burnout, it's a real thing. So know when you need to take a break and go out and do the things that you enjoy doing. For example, I love being outdoors. I love going into nature, boating, sports, and spending time with my family. My kids are 10 and 12 years old and I love doing outdoor activities with them, sporting events. I just love that. And you got to make sure that you take the time to recharge, doing the things that you enjoy doing that you love doing, get your mind off of things. And often in product, it's funny enough because your best ideas will come not when you're at the job, your best ideas will come when you're out there doing something else different. It will not come when you're sitting at your desk, it'll come when you're walking down the park or you're somewhere else at a particular event, social event, that's when you're like, wait a minute, something just sparked.

Ana: Yeah, that's true. I love it. It resonates with me so much. I had so many nice ideas when I took a shower, just like in relaxed mode. my God, that's a nice idea.

Santiago: Exactly, exactly. Yeah, shower ideas are the best and they're a real thing. They're a real thing.

Ana: Okay. All right, Santiago, it was an amazing conversation. I like it so much. You've shared so many interesting and insightful things. I'm thrilled to have you today. Thank you.

Santiago: Absolutely, thank you for having me.

That’s all for this time. If you think your colleague or friend could benefit from these tips, please share this episode with them. Thanks!

How to build an effective product strategy with Santiago Cardona Cieden

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