Inspiration

Episode 59 with Guest Esteban Contreras

Hosted by Sean Flaherty & Matt Bush

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About Esteban Contreras
Product Momentum Podcast guest Esteban Contreras
Esteban Contreras
Hootsuite

Esteban Contreras is a Senior Director of Product Management at Hootsuite, the global leader in social media management software. Esteban has spent over a decade at the convergence of technology and marketing. He is passionate about solving problems with software and developing customer-centric, mission-driven product teams.

At Hootsuite, Esteban has driven the vision for social media marketing solutions and led product portfolios responsible for publishing, engagement, mobile, analytics, integrations, and machine learning initiatives. He has advised tech startups in SaaS, gaming, social networking, and e-commerce. Originally from Guatemala, Esteban lived in the United States before moving to Vancouver, BC where he now lives with his wife and two kids.

What does it really mean to be obsessed with serving your customers? How can we balance mission and vision to build great products?

In this episode, ITX product leader Matt Bush joins Sean in a lively conversation with Esteban Contreras, a Senior Director of Product Management at Hootsuite. Like many so organizations in the space, Hootsuite deftly adapted to a pandemic-driven business climate to continue serving customers from a fully remote work environment. Esteban shares how celebration and culture were key to this process.

Some customers seem less concerned with the long-term vision of your product. Even product teams sometimes struggle to grasp their long-term goals when they don’t know the path for getting there. For some, Esteban adds, “A successful day simply means getting out of work on time.”  And that’s why mission is so important. Mission explains why we exist in the first place.

Listen in to catch more from Esteban; learn about his unique entrance into product management and cools ways to celebrate activities that are integral to customer success.


Sean [00:00:19] Hello and welcome to the Product Momentum podcast. This is a podcast intended to entertain, educate, celebrate, and give a little back to the product leadership community.

Sean [00:00:32] Well hello and thanks for joining us today as we interview Esteban Contreras from Hootsuite. Exciting, exciting interview. And today is a little change of pace. I’m joined by Matt Bush, veteran product leader at ITX. He works on some of our largest accounts. Hey, Matt.

Matt [00:00:48] Hey, Sean. Thanks for bringing me on. It was an absolute pleasure to be a part of this conversation with Esteban. Awesome insights. There’s a quote that stood out to me: celebrating art and science of delivering, which I thought was just something that resonated really well.

Sean [00:01:01] Yeah, and keeping a healthy balance between vision and execution and how we spend our time. Esteban has a lot of really great insights to share. I hope you enjoy this podcast. Let’s get after it.

Matt [00:01:11] Let’s do it.

Sean [00:01:15] Well, hello, everyone. Welcome to the Product Momentum Podcast. Today, we’re going to be interviewing Esteban Contreras, who is the Senior Director of Product Management at Hootsuite, a global leader in social media management software. He’s been in the product space for over a decade at the convergence of technology and marketing. He’s a passionate, passionate dude, from one of my favorite countries, Guatemala. Maybe we’ll talk about that a little bit today. Esteban, welcome.

Esteban [00:01:40] Thank you. Thanks for having me. It’s great to be here.

Sean [00:01:42] Yeah. So what have you been working on lately? What are you passionate about these days?

Esteban [00:01:46] What am I passionate about these days? Yeah, well, it’s something I think we should all be thinking about, considering how 2020 went. You know, we’ve been super busy at Hootsuite. 2020 was a shifting year for probably everybody, so going fully remote. Our users went remote. We saw a new phase of growth for our company. So seeing two hundred thousand paying customers, probably the largest in our space. So we did a lot of things and it was a busy, busy year. I think this year we’re refocusing on, where do we want to go long term and what are we doing? So we’ve done some acquisitions. We have a new CEO. It’s an exciting time at Hootsuite.

Esteban [00:02:23] And then in terms of what I’m seeing and what I’m passionate about, probably on the Internet, I think there’s a nonstop flow of information and content and media and new ways of consuming that, you know, new ways of doing community and new ways of thinking about social networks and human networks in general. So it’s an interesting time for the world and I’m kind of fascinated by a lot of things that are happening and how humans are coping and surviving and thriving.

Sean [00:02:52] Anything you want to share about, like, I think this is an interesting subject, like, we had to adapt. We’ve all had to adapt. In the product suite specifically, are there any, like, pivots that you made or adaptions that you made as a result of the things going on in the world? Just curious.

Esteban [00:03:05] Yeah, I think one of the biggest things was really trying to make sense of customer obsession and, what does it mean to put customers at the center? I think we’ve always said it, right. It’s a pretty common thing to say and to think about. A big shift for us was trying to make it more tangible and really figure out how it is that you can revolve around customer outcomes and what your users are really trying to do and understand them more from a more human level. So I think that everybody going to remote is a simple example, but it shows you that people have to adapt.

Esteban [00:03:43] People have lives, you know, people, sometimes for them, a successful day using a product is getting out of work on time, you know, and it’s as simple as that. They’re not looking necessarily for your long-term roadmap or for a lot of the things that we’re concerned with. They’re just concerned with getting home and getting some dinner. So really getting to the bottom of, why do we say these things and how does that affect how we do things and how should it affect what we do on a day-to-day in terms of what do we celebrate, what do we track, what do we measure? Celebration is an interesting thing. You know, if you’re always celebrating shipping, then that’s what you’re prioritizing, right. If you’re always measuring delivery, then that’s what you’re focused on. So we did some introspection in really trying to understand why we say certain things but sometimes do other things.

Matt [00:04:37] Some interesting perspectives there, honestly, like the whole concept of designing things or using a product in order to just get out of work on time. I think that’s the first time that I’ve ever heard anybody say that only it makes total sense to me. It kind of just resonated. But I wanted to switch gears a little bit and just kind of focus a little bit more on product and leadership and kind of what your path was. I’ve heard a lot of interesting things of how you came into the space and how you kind of grew within product. So can you tell us a little bit about your journey from being that visionary in Guatemala to being a leader of the product realm?

Esteban [00:05:10] Yeah, sure. We all have our stories and I’ve interviewed a lot of people over the years and everybody has a really interesting path into product management. From time to time, you hear somebody that went through school thinking they wanted to be a PM and then they became a PM and now they’re trying to move up as a PM. But for many of us, that’s not really the way that we got into it and it’s probably because, in many ways, it’s a relatively new role and function that is getting more mature and more solid.

Esteban [00:05:41] I was born in Guatemala City, Guatemala. My parents had a small business and my dad had a computer and we had a small apartment. So the computer happened to be in my room and that’s where the data entry happened. And then one day my dad said, “Hey, you’re going to be responsible for data entry,” and I started doing data entry. And in no time I was sending feedback to a point of sale software vendor and I was building the first HTML web page at the time with a guest book and everything. So my turning point into product was really seeing an opportunity to help my family and an opportunity to do work without really expecting anything in return, just the reward of helping the small business that my parents had.

Esteban [00:06:27] You know, I wouldn’t say I was a visionary in Guatemala because I was only there until I was 18 years old. But I started working early and I started pursuing everything online and digital because I was an immigrant in Texas. As a college student, I couldn’t get a job. My first three jobs were unpaid internships. So you have to figure out a way to make a living by finding ways to build websites or to outsource designers and just find a way to get started. And I really wanted to stay in the US so my path to product management was just probably a combination of my passions and the desire to survive and make a living doing something that I didn’t understand how people could get paid for it because it seemed fun for me.

Sean [00:07:15] I always love to hear stories because it’s amazing to me how many different places product leaders come from, you know, and your story is unique for sure. I want to pull a thread about something that you said earlier. Like, your customers don’t really care about your roadmap. Like, we kind of know that. They’re not in the product every day. They just want to get home and have dinner with their families and they just want to get their job done. And it reminds me of an experience I had with a Fortune 500 company with a multi-month customer focus group. Six figures they spent on this focus group exercise. And at the end of it, I remember going through the book that they produced and all the learnings and all the findings. And you know what the one usable nugget that we got from that whole exercise was? Your users just want you to get out of their way. Especially in the B2B world, which is where you are and this is where this company was, they want to get their jobs done and everything you can do to make their job and their life easier, that’s really what it’s about.

Esteban [00:08:12] I mean, absolutely. Making their life easier, right? And that’s where sometimes I think my point about getting to dinner is that there are moments in which your buyers are very interested and all they can think about is a tool they’re going to buy. And when they’re using it, there’s a moment in which all they can think about is all the things they wish they had. But day-to-day, they’re not thinking about all those products as roadmaps, right, and all the things that they’re missing. Sometimes they just need to know that they can trust you to solve the problems that they’ll have.

Esteban [00:08:42] And at Hootsuite it’s interesting because a lot of what we do is on top of social networks and integrating with our large ecosystem. So in many ways, it’s impossible for us to just think about the features and the things that we want to build. We really need to understand what’s happening in the broader space and truly the ecosystem that our customers have, which can be pretty big. You know, there’s all kinds of systems that they have, things that they want to integrate with. And I think that’s why I’ve always gravitated towards B2B. That’s where I started and that’s kind of what makes sense for me. And I try to see it from a very empathetic view of, you know, “this is someone who has a regular life; they’re living, breathing people.”

Esteban [00:09:22] It reminds me of, there’s a book by Paul Graham called Hackers and Painters. I don’t know if you’ve heard about or seen it, but Paul Graham is known for a lot of essays. He has at least one book that he published that I know of. And in it, he writes about how all the greatest paintings were paintings of people because people are what people are interested in. And so all creators create for this human audience and all software makers make for a human audience. All influencers on social media make for a human audience. And it seems very obvious. But that’s sort of what separates great software and great products from the bad ones or the OK ones is just really trying to get a little bit deeper into what makes people move and what gets them to accomplish something, as opposed to a lot of the bells and whistles and a lot of the stuff that we decorate it with.

Matt [00:10:11] There are a lot of interesting little tidbits through all of that answer that I really enjoyed, but I think all of it really, you’re customer-centric. You want to always be thinking about who you’re trying to cater to. I think that leads really well into the next area that I wanted to touch on a little bit. When you think about customers, you have to think about where you’re headed. What are you trying to build for? What are you looking to do? What are you looking to accomplish? So kind of that mission and vision concept, where if you’re really talking about vision all of the time, then it’s really at the expense of what you’re trying to drive towards, right. But if you’re really looking out three years into the future all the time, then you’re really not focused on those users. You’re not focused on what you are trying to accomplish for your users. So I’m curious to get your insight into, how can project managers really think about vision differently to create that better alignment between what they’re doing and why they’re doing it?

Esteban [00:11:05] Yeah, so this is exactly the kind of thing that I’ve been thinking about a lot. Obviously, a vision is essential and a mission is essential. Vision is ultimately where you’re going. Mission is about the what, the how, the for whom, the why. It’s about today and every day and how do you do what you do and get enough motivation and drive and reasoning for getting to that future state, that tomorrow that you’re trying to get to? What’s been interesting for me has been a shift in mindset. When I was younger, I imagined myself as a visionary. I think of, like, what the world could be. And it’s easy for me to get into a situation of understanding or imagining a very ambiguous end state where you can make a statement or you can say, “here’s where we’re going to get 5 years from now, 10 years from now.” Some people really struggle with this, but I just tended to go in that direction. And as I became a product leader myself, I got myself into situations where you’re leading an entire product team. And that vision, if you’re not good at communicating, first of all, you lose people and they see the realities, they see the roadblocks, they see all the problems, they see the next sprint or the next quarter and they get hung up on that and you lose them. You sound like a crazy person sometimes.

Esteban [00:12:24] So that’s one consideration with vision, overemphasizing vision. The other potential problem, I think, with only thinking of the vision of where you’re going to get to is that you can take shortcuts, right. If you’ve overfocused on vision, I have seen people get tempted with going through the workaround or finding a way to do things in maybe not the best way that they should have done it and taking corners or skipping steps and then maybe doing things that they wouldn’t have done otherwise because they’re so hung up on trying to get to somewhere and sometimes as fast as possible. So I think being missional is something that I’ve embraced much more and just trying to understand, how do you motivate your team and yourself about what you have to do tomorrow, right, versus just where you’re going to end up? But obviously, you can’t do one without the other. You need both.

Sean [00:13:14] Yeah. So I think there’s a healthy balance that you have to strike between where you’re going and where you’re going to get right now, like the roadmap and getting things out the door right now. It kind of reminds me of the conversation that we had in the pre-call about making sure that you’ve got the right amount of built-in tension between discovery and execution because you got to get stuff out the door and we all have limited budgets. We can’t just be doing infinite discovery.

Esteban [00:13:38] Yeah, that’s a good point. There’s definitely, you know, discovery, at the end of the day, is about building the right product, right, and delivery is about how well you build that product. If you’re so hung up on a future state or an end state, you can easily turn that vision into a very specific solution. And I’ve seen product leaders do this. I’ve seen product managers, I’ve seen CEOs and CPOs do it where they just decide, “the future vision equals this specific solution and we are going to figure out a way to get it done and we’re going to do it in record time.” And sometimes it works out, other times it can be disastrous, right. Especially if you’re building the wrong thing and then you end up losing customers, you end up losing the market, you lose your employees, and you’re really struggling to figure anything out because you’re aiming for a good future state, but you don’t think about how you’re going to get there.

Sean [00:14:35] That’s amazing. You mentioned earlier the importance of celebration. And this one’s kind of close to my heart, like, having a proper cadence for celebrating. And you talked specifically about celebrating the shipping itself, which I thought was profound. It’s something I never thought of. We always try to think about celebration from the actual accomplishment, but I like the concept of shipping because you prioritize what you celebrate, you prioritize what you measure. Right. What gets measured, gets managed. At Hootsuite, you have a bunch of teams, not just one team, I’m assuming.

Esteban [00:15:04] Yeah.

Sean [00:15:04] Do you have a trick, you know, an arrow in your quiver around celebration? A way of talking about it?

Esteban [00:15:09] Yeah, we have portfolios, which are teams of teams, and we have multiple portfolios. You know, Hootsuite has a great culture in that we have a good balance of certain things that we standardize across all our teams. And there’s also a really unique element of autonomy and I would say very healthy autonomy where it’s not about being independent, but it’s more about being independent, but doing it in a transparent way and in a collaborative way. So I think we’re still trying to figure out that aspect of celebration and something that I’m spending some time thinking about and asking our product leaders, how do we do more of that? How do we do it well? Because I wouldn’t say that we are there yet. I think we celebrate when we release something, when we ship something, even when it’s an internal release, right, or a beta. We celebrate those, but we’re also starting to think, how do we celebrate traction? How do we celebrate adoption and engagement from our customers?

Esteban [00:16:01] And I think culturally, what’s happened with a lot of tech companies is that most people in a software team are software developers, they’re engineers. So we allocate the most people and the most time to delivery. So we celebrate first and foremost this art and science of delivery. And I think that that’s a good thing, but it shouldn’t be the only thing that we celebrate, right. We should celebrate things like discovery. We should celebrate, ultimately, getting to where we thought we were going to get to in terms of what is going to make an investment or a project or a feature successful. And I really think it comes down to the culture. Some teams will do this just automatically, and other teams, they need to be reminded or they need to be encouraged to do this so that you don’t have just this culture of pure shipping or even cost-saving, as some people would think about it, right. Like, “oh, you shipped earlier, you saved some money,” right. But more of a culture of traction, of progress, and the right things that the company cares about and ultimately what your users care about. If you could get to celebrating their outcomes and what they’re trying to do because you know that they’re accomplishing it… And sometimes you don’t get to see that, but if you’re able to, that’s amazing.

Sean [00:17:12] All right. To summarize, I heard a bunch of things here and there’s a theme to what we’re talking about. You need a healthy balance between vision and execution, you need a healthy balance between discovery and execution, and you need a healthy balance about how you celebrate and what the cadence should be. And the reality is, we build products. That’s what our industry does. Until we release them in the wild, they didn’t exist before. Every team is different, every team’s culture is different, every product is different, and because of that, this autonomy thing is really important. In recognizing that, we have to customize our cadences by team to maximize motivation. I love it.

Esteban [00:17:50] Yeah.

Sean [00:17:51] Maybe that wasn’t a summary. It was a little longer.

Esteban [00:17:55] Yeah, I agree with that.

Matt [00:17:57] So, yeah, listening about all of the ways of celebrating and everything I think was really cool to hear, especially with when you talked at the beginning of the session about how the transition over into the remote aspect of, like, the workforce and then also your customers. The celebratory aspect around that’s been something that I’ve thought a lot about as well, just with my teams. But I wanted to transition a little bit more into, well, and I guess it’s kind of in the same vein as what you said with trying to determine how best to celebrate, but dig into the ideas of around discovery. So with all else being equal, it seems most organizations have like this built-in tension between discovery and execution. So I’m curious, do you see any root cause within the industry’s kind of bias towards delivery at the expense of discovery?

Esteban [00:18:44] Yeah, I think it comes down to what’s just a very natural tendency going back to the fact that if you allocate the most people, the most time, the most attention to delivery, then that’s what you’re going to see as success, that’s what matters, right? It’s, let’s not celebrate activities. We’re not going to celebrate just coding or writing documents or creating UX flows. Let’s celebrate when that activity culminates into something tangible. And I think that’s just a common, human thing to do, you know. If we were doing this with physical objects, it would be the same thing.

Esteban [00:19:21] I think the gigantic difference is that the idea of a release doesn’t exist in the same way that you have it with a chair or with a table, In software, it’s never finished. So I think we are trying to measure things that show progress and we’re trying to celebrate the teams that are doing it and that’s for good reason and I think we should continue to do that. The question is, how do you celebrate some of the things that are not as evident, right, such as having the right strategy or having the right objectives? Celebrating seeking truth, you know, like that’s ultimately what discovery is about. And of course, you can’t celebrate everything. You can’t be celebrating all the time. Maybe that’s another reason is that you can’t just be all celebrating or feeling bad and dwelling about the things that didn’t go well. You need to learn and you need to adapt. I think just having the intention of thinking about it starts to change how you do things. And when you share these thoughts with others in your team, they usually resonate. And then everybody starts having thoughts on how to change that and make things a little bit more balanced versus so oriented towards the shipping and delivery piece.

Sean [00:20:27] Well, that kind of leads into my next question. How do you define innovation at Hootsuite?

Esteban [00:20:32] The way we tend to think of innovation is we think of examples of people who have done great innovations. You know, you think of a Nest or you think of an iPhone or you think of a Tesla. I think that that’s one element of innovation. It’s something where there’s a remixing or a rethinking and to do something in a way that looks and feels so different than anything you’ve ever seen. I think that’s one element of innovation.

Esteban [00:21:00] I think there’s also another element of innovation of just seeing your past self as the one that you’re sort of competing with or that you’re trying to get better than and just innovating over your previous self, if that makes sense, which is kind of like, if you want to become stronger, then you probably shouldn’t be looking at people who are, you know, ten times stronger than you. You should be looking at, “how strong was I yesterday, and how strong was it two days ago?” And that probably applies to any hobby or interest or line of work.

Esteban [00:21:31] So I do think that there is an element of innovation that’s less exciting and less interesting and we don’t hear about it on blog posts or on Clubhouse conversations. And it’s more around, how do you actually solve a problem? And it doesn’t really matter whether it’s new or shiny or cool or interesting or buzz-worthy. It’s really about solving problems, not just in the way you always have, but trying to solve the problem and sometimes that requires you to think differently and rethink things and bring in people that are different than you and find a way to solve that problem in a creative, unique way.

Sean [00:22:06] Yeah, I’m a big believer that the small innovations matter and they add up. You know something is in innovation when it changes the behavior of your consumers or anybody in your ecosystem for the positive. So thank you for that.

Esteban [00:22:18] Yeah, absolutely.

Matt [00:22:20] I thought that was great. The one question that we tend to ask everybody who comes on to the podcast is, what are you reading and what would you recommend?

Esteban [00:22:28] Oh, man, I’m reading a lot of books all the time, so I’m probably not a good person to give you a single book. I recently did reread Hackers and Painters. I think that’s why I brought it up is because it’s a book I read years ago. I like to sometimes go back to books that are 15, 20, 30 years old and see how much it resonates today. And so, you know, one I would recommend is Hackers and Painters by Paul Graham. And then a more recent book, I’m currently reading The Product Led Organization by Todd Olson. I think that’s one that I picked up recently.

Sean [00:23:06] Well, thank you, Esteban. It’s been awesome having you on the show. We learned a lot and I look forward to getting this out to the community.

Esteban [00:23:13] Thanks a lot. Appreciate it.

Paul [00:23:17] Well, that’s it for today. In line with our goals of transparency and listening, we really want to hear from you. Sean and I are committed to reading every piece of feedback that we get so please leave a comment or a rating wherever you’re listening to this podcast. Not only does it help us continue to improve, but it also helps the show climb up the rankings so that we can help other listeners move, touch, and inspire the world, just like you’re doing. Thanks, everyone. We’ll see you next episode.