Jason Monberg - Adapting to constant technology shifts to endure market value

Jason, welcome to our podcast. We're very, very happy to have you here today. Anything you want to add to the introduction?

Jason Monberg: Thank you. Well, I'm, I'm thrilled to be here and I'll, I'll just add that I've been I've been doing this work for, for 25 years, helping companies develop digital products and worked across the spectrum from like two person startups to some of the largest companies in the world.

And I'm just, I'm just thrilled to share my experience. So hoping it can be helpful to folks out there.

Tim Butara: Well, so let's just go ahead and start with that. So can you share in the context of the conversation that we're having today? Can you share the most important lessons that you've learned from, from, you know, the 25 years that you've been doing this?

Jason Monberg: Yeah, absolutely. And that's, you know, in some respects, that's such a hard question because I'm still learning. There's, there's so much to learn. And I feel like, you know, one of the most important things is just, you, you have to constantly pay attention. But when I think about like companies actually managing technology and developing products and thinking about where they're going, a few things really rise to the top.

And One of the most important things I think is patience, and it sounds, it's a little bit counterintuitive, especially coming from Silicon Valley, where I think everything is, is go, go, go, you need to be first. But the reality is that really large technology shifts. take years, if not decades. And I'm thinking about, you know, when the internet arrived, it didn't just arrive one day and suddenly we had Amazon.

It took years and years. And it's not always the, the, the first company to get their product out. That's going to quote win. And these, these products utilizing technology evolve over time, right? So we have different generations of, if you just look at like, CRM systems. We've had, we've had generations of CRM systems that come through.

And so I think this notion of patience and being thoughtful is really powerful. And related to that with technology is also this notion of understanding why you're doing something. So I see a lot of people making What I would consider sort of knee jerk reactions and it's it's the type of thing where I think if they if you can step back and this doesn't take this doesn't have to take a long period of time.

This is just stepping back, making sure you're getting the information from your internal sources, your external customers and really thinking through why. You're going to incorporate some new technology or follow some shift that you perceive. And we have some really fantastic examples. Like if we look at AR and VR really popular several years ago, and you saw lots of companies like piling and trying to do something, but it wasn't, it wasn't a shift that was at the magnitude that every end user.

Was going to suddenly start using it. They're not going to wake up tomorrow and spend a thousand dollars on a headset. And I think that's, it's just a, it's just a good example where this is, it's still playing out. Right. And, and I think there are some fantastic uses, but is it, is it the type of thing that, you know, target, which, which is a leading physical retailer out in the United States, do they need to suddenly have a VR strategy?

Maybe, but probably not, you know, or they probably have some time to think about it. And so I think we see a lot of people jumping in without really thinking about why they're going to do it. What kind of value are they going to give to their customers? What does it mean for their business? And so I think there's a lot of efficiency that That one can find there and then there's two other things that are more about how we do our day to day job.

And so the other one is communications. I think that a lot of times when we're. Working in an environment with rapid change, the, the way that you communicate can really impact whether you're successful or not. And this, this comes straight into things like agile development and what type of processes you use.

But we're, we're like huge fans of writing things down as, as, as a It might seem a little pedantic, you know, when we're like rapid fire, making decisions in Slack and things like that. But ultimately we want to have sort of a a document somewhere that's telling us why we did what we did. And we're communicating what we want to actually accomplish.

And when we do that at the, and this is really at the sort of micro level even thinking about change in terms of the library that you might be using in a product. It's incredibly valuable to be able to go back and see this history. So we're always looking for that when we talk about big changes, like, Hey, should we incorporate Gen AI into our product?

Or even the small changes, like we're going to swap out a library because all of these things have massive ripple effects. And then the very, the very last thing, which is it's a little bit orthogonal, and this is more of just a really general purpose learning from all the years is I think that the relationships that we develop in our work are absolutely profound and they, they really impact where you go.

And I think as a, you know, when I was like a 20 year old developer, turning into a product manager, trying to be an executive. I had zero idea that the relationships I was developing then with people were actually going to impact where I went and what I did 20 years later. And I still get phone calls from people saying, Hey Jason, I remember a conversation we had, you know, 15 years ago, and I'm working on a project that's related to that.

Can we talk right? And just, just being able to nurture those relationships I think is really powerful. And when we talk about Change. That's where I get a lot of my information. Certainly I read the news. I read blogs. I really like talking to people who are having experiences with this technology to find out what they're up to.

I just, I actually recently had someone that I worked for at one of the startups. He started a company, he recruited me and he's gone on to do all kinds of interesting things, investing, executive roles, and he was coming To AI. And he just gave me a call and said, Hey, I know you guys are working on some AI stuff, and I've got a bunch of questions cause I've got this big project I want to do.

And and we just chatted, I introduced him to some other folks that I've been talking to. And just through that process, it was keeping me up to date on where the trends were going to technology. So I think that that is immensely powerful and really important for folks.

Tim Butara: Yeah, but that was a great start.

Some really great points here, but basically all of the points that you highlighted. are really important in business, but they're also just, you know, if you adopt everything that you just said in your personal life, then you know, you'll, you'll be, you'll be that much better for it in your personal life as well.

So it's patience, knowing the why, having good communication and having good relationship that you nurture and that, you know, that, that as you just as you just exemplify, it can bring you a lot of value down the line if you do nurture them properly. Absolutely. Yeah. So when it comes to, you know, enduring market value, or I guess, I guess when it comes to scalability, right, what have you found to be kind of the most important factor or factors in order to scale, not just succeed, you know, in a like in a one shot manner?

Jason Monberg: Yeah. Yeah. Well, and, and so I, I had a question for you. Like when you think about scalability, are you thinking about technology or teams or the, the product from a feature set standpoint, or maybe all of the above?

Tim Butara: Yeah. I mean, I'm guessing that if you wanted to scale the product properly, so that it would continue satisfying and meeting its users needs That would just automatically necessitate expanding your team as well.

So I'm getting, I'm, I'm kind of meaning all of the above.

Jason Monberg: Okay. Yeah. So I'll just tackle it sort of like one layer at a time. So when, when I think about scaling from a technical standpoint, I think one of, one of the aspects of this that a lot of people might not have experience with is that when you're really doing.

large scale scaling or hyperscaling, you are actually rewriting your product. So, you know, the, the initial version of a product typically doesn't last that long. If you're going to go through a massive scaling cycle and we've seen name brand products that are pretty well advertised. I think Facebook is probably one of the best examples, but you know, you can, You can find people talking about, you know, the five or six different major kind of like rewrites as they went through like different levels of scaling.

And so I think the cautionary side is don't try to preemptively scale for every situation, right? You don't want to over optimize early on. What you really want to do is get a product that's successful so that you have that scalability problem. Now there's lots of things you can do to to prepare yourself.

And maybe that's the, maybe that's the, you know, the message is like, be prepared, but don't over optimize. And so when I think about preparing, I think a lot more about the infrastructure and the data structures. These are like really the fundamental components of your product that will let you have flexibility.

If you want to have, say a publicly accessible API later on, you really have to have like intelligent data structures, but I, but I also think you have to be very open about the fact that you're probably going to. Rewrite this at some point in time, if you're, if you're really finding success and there are also lots of products that maybe don't need to scale.

Because they, they sort of, they hit their natural point and what you're really interested in is scaling the features or making sure that it's easy to maintain. And so when I think about it at that level, I think about really clear code. I personally don't like products that are written in obfuscated code.

I like stuff Unpacked. I'd rather see really verbose code that any engineer could look at and go, Oh, I, I can figure out how to fix this as opposed to like some really dense, functional programming. That's, you know, it's doing a lot of stuff in a, in three lines of code, but you really need to be an expert in that.

Code and product to unpack it. So I think about that sort of like scalability from a maintaining standpoint from a feature standpoint, I really like to look at the, the UX that's generated and, and like, we often have conversations about like, what kind of space does our UX have? So obviously like when you first create a product, if you're not going to.

Have every feature in it. But if you can look forward and you can say, well, we're, you know, we probably think we want to have this analytics portion of it, but that's probably a year out. And you just look at the user experience. Like, do you physically have space on the screen? Or additional features, or have you done something that's like really putting yourself in a corner and it's like, this is all you have.

So think about from that standpoint. And then of course, like your, your team and your organization, I was actually reading last night about linear and how they organize their teams. And I loved their, they're about 50 people, but they are going through lots of growth right now. And what they were talking about was how they like to have.

really small teams, you know, two engineers and a designer work on a feature on one part of the product. But then when they're done with that part of it, move on to another part of the product. And their goal very clearly is to have lots of people that understand the entire product. And I, I love that as a philosophy, particularly at this stage that they're at, I think at a certain point, that's, you know, you're not going to have any runway with that.

But I do think about like, When, when you're putting your teams together, what's your unit of measure, right? Like, is it a five person team? Is it a three person team? Is it a 10 person team? And I think particularly in the early stages working with that unit. And so how many, you know, if, if I get a five person team, that's, that's working very well, can I replicate that with two more five person teams?

And then can I get that to like five, five person teams? And And as you're scaling, and this is, this is similar with the product where you might be at a point where you need to rewrite it, I think you have to be open with your teams to say, Hey, now we have five, five person teams. Are we at a point where we have to rethink how we're organizing ourselves and managing ourselves?

Or maybe we can continue in this pattern. And I think that that's, that's probably one of the fundamental things about scaling in general is that you're, you're going through these phase shifts as you scale. And what you want to understand is whether you're, whether you're at a plateau and you're staying at that plateau.

Or if you're going through a phase shift and when you go through a phase shift, you have to rethink how things are organized. And so this is really to say, you, you really need to understand where you're at in the cycle, and then you have to apply your kind of what, what you want out of it. You know, what are your goals around this?

Why, why are you going to change things up? Maybe you need more efficiency and maybe your quality is suffering a little bit, but you have to look at things like that. in terms of your team. And then there's, there's a whole lot about business scaling, but that's not, not as much my purview.

Tim Butara: This basically all still tied back to, to the four points that we highlighted in, in the first question, right?

So patience, knowing the why good communication and relationships. And also, I mean, I guess preemptiveness is also a very important part of it, right? If you want, like in terms, especially in terms of something like, Feature scaling you know, when you roll out features later on, as you said, and you know, and you might realize that you don't didn't leave enough screen space for the new feature to be able to be incorporated in a user friendly manner that doesn't break stuff.

So yeah.

Jason Monberg: Yeah, absolutely. Right. And there's this notion of I think there's this, like, there's this balancing act of like solving the problem that's right in front of you and looking ahead a little bit. But not too far, right? Cause you don't want to overdo it, but you do, you do have to have some future thought for sure.

And, and try to be as preemptive as you can within reason.

Tim Butara: I mean, if we're talking about enduring constant technology shifts, you know, a bigger feature or a bigger, more important product might take it a really long time to develop, which might mean that, you know, From the time you start working on it from the time that you realize, Oh, that this is like a potential market niche.

It's something that the market could benefit from. It's something that we could benefit from if we roll it out quickly enough, but then by the time that you actually develop it needs and the market. will have changed, not just might have changed, right? So, so you can't really get anywhere if you only develop for the current need, because the current need might not be a need still once you actually finish developing for it, right?

So you need to be future ready.

Jason Monberg: Yeah, yeah, absolutely. And, and that, that comes back to that notion. Like when, like, if we really look at like incorporating new technology into what we're doing, those, these ideas of doing experiments, or doing small releases first, I think are really powerful. One of the things I was just thinking about recently was when, when I started out in the 90s you know, I, I was really influenced by extreme programming.

Like that was the first kind of like literature I read. About this, what we consider sort of agile ways of development. And you know, they, they were promoting these fast release cycles, but a lot of the software that they were writing then was, it was released on the scale of years. So they would spend like a couple of years doing something.

And so, or a few years. And so a fast release cycle for them might be six months, getting a feature out and testing it, and then another six months for us. We, we regularly release the first version of our product. Of the entire product in four to six months. And so we have this, this like a really great situation where we can, many organizations, I think can experiment with new technologies in a matter of weeks or a small number of months.

And I do think that that's a really, really important factor. If, if you get to the point where you're saying, we really need to try this, we need to invest some time in it, that ability to. Push out those features to whether it's a small group or or your entire audience. That is, I mean, it's really profound in terms of the ability to distribute and get feedback.

And I, and I think if you're right, if you're, if you're deeply involved in your product and navigating technology change, I think that's a must for you to be able to do these, this sort of rapid iteration prototyping experiments.

Tim Butara: Yeah. So you just said that you started in the nineties. We said at the beginning that you have over 25 years of experience, but you know, I'm, I'm not sure how well, The 20 years of experience then was able to prepare you for what came when COVID happened, so wondering what were like, what, what were some of the most important shifts, some of the most important changes that you've noticed in your career post COVID that came with COVID.

Jason Monberg: Yeah. I think in 10 years, we're going to have an amazing amount of experience written down, and we're going to talk about these changes. I, again, I think it's one of the things we're still learning about, but I think nothing really prepared us. I do think that it was, well, certainly coming from the San Francisco Bay area, we were already doing a bit of distributed work.

I think that working like we, we often work with teams that are in other countries and I think that ability and, and certainly the type of work we do where we're on a screen all day. Is easier if you're remote. And so I do think that the natural state of our business made it easy to transition to at home.

But the, you know, the changes are, they're so much more fundamental. And so the biggest thing, okay. So, so COVID happens and what we're, we're like, maybe our. We consult with companies. We do a lot of in person work. We find in person work to be incredibly powerful. We can move so fast with people. So that all goes away for a couple of years.

And we were concerned about our business. We just didn't know if it would, if it would exist. So the first thing was, can we do business? Not just the work that we do, but also the sales cycle. Can we generate trust with people? Over a video communication link and pretty quickly, I think I'd say about three months into it.

We saw that we could conduct all of our business online. And initially, that was a fantastic thing. I think we changed our processes a little. There was more written. work that was required. I think communication became a little bit more challenging, and so we had to adjust. That has not been easy or evenly distributed for everyone, but everyone I think sort of like slogged through that.

The really interesting part has been coming back to the office. So now we can be in person, and I think we're in this state where We are, we're, we're probably never going to go back to how it was where everyone comes into the office every day, but we're in this really deep hybrid sort of state. And so as a, as a business owner, And someone who's working on these projects where we feel like being in person is, can be really powerful and is really important.

I think that we've had to pick and choose when we ask people to come in to the office. And this also means a lot of people moved. So this also means a lot of people are getting on planes and staying in hotels in order to make this happen. So, so there's a lot of emphasis on really taking advantage of that in person time.

The other side of it is when we're remote is how do we maintain a culture that's gonna, that's sort of like self reinforcing where people are feeling connected. That's been That's been a real struggle, but we do things. We'll do online events. We'll do additional, you know, if we do have people coming in, we're going to try to do some other activities like a social activity.

And so, so these are all the things we're working on. Interestingly, I don't think that it's really impacted the quality of the work per se. So we've still been able to design and develop the quality still feels Very high. I think, I think we're just losing out on some of the speed and interesting communication we can have when we're in person.

And I do think we need, we're going to keep getting better at that. We need better tools. I'm certainly concerned about like the intersection of, of post COVID and AI. And like, what does that mean for work? There's some really big questions there, but that's, that's how I've, how I've seen it. We also have done a fair amount of work with physical hardware products.

And so with those teams, there is a, I think there's more of a consensus that you need, you need to actually be with the physical product. And so if we can't ship out a version of a product, you know, if it's, if it's a big expensive machine that we're working on, we're The teams are comfortable coming together.

So we see pockets of work that actually operate in the, as they did pre COVID, but certainly with where, you know, most of what we do is pure software and people can do software from anywhere and they are. And I think as a, as a, as a community, we just have to accept that. That's, that's how it's going to be.

And, and find other solutions for getting, keeping our teams together.

Tim Butara: I mean, that was definitely one of the. Biggest changes that we've all experienced right on a personal level and probably, I mean like you as a CEO, you experienced it both on the level of the CEO, somebody who's leading the company and on a personal level.

So, so I'm guessing that, you know, that this is something we probably talked a lot more about hybrid work and remote work, you know, in the first few years after COVID now the conversations have kind of died down, but I still think that it's relevant to discuss here. You know, in the context of these adaptations and these shifts, which are, you know, technology, you know, COVID was, COVID fueled a massive technology shift.

It wasn't in itself a technology shift, but it was related to a lot of technology shifts, right? So it doesn't necessarily mean to, need to mean, like, the release of GPT 3. 5 or something like that. It can also be another driver that kind of drives these shifts, right?

Jason Monberg: Yeah. Yeah. And you see, you see a lot of like people who are developing products are taking into account the fact that their customers are going to be distributed.

So you're starting to see that actually impact some of the feature sets as well, which is really interesting, right? Like it's a, we've all taken this turn in terms of what the products need to support, particularly in these Desk job, high tech environments.

Tim Butara: So, so this is like in terms of like some kind of B2B selling B2B hardware, stuff like that.

Jason Monberg: Yeah,

Tim Butara: yeah, absolutely. Cool. A very, very great and very interesting conversation, Jason. Just before we wrap it up, I just like for you to maybe, maybe based on everything that we've discussed today to kind of sum everything up, what will be your top tips to listeners for being able to better adapt to all of these shifts that we discussed?

Jason Monberg: Yeah, I mean, for sure. Coming back to the sort of introductory points of really having patience and understanding why you're going to follow some kind of technology change or why are you incorporating a new technology into your product? What is the value there? I think that is It's so fundamental for a business and it's, and it's, it can be very easy to overlook.

And then, you know, making sure that you have a great communication and you're paying attention to the relationships because these are the things that are going to support you in the future more than anything else.

Tim Butara: Awesome. And if people wanted to learn even more or connect with you or learn more about presence, where can you do that?

Jason Monberg: Oh yeah, absolutely. So I'm on LinkedIn, it's just, it's just LinkedIn slash Jason Monberg. And then you can email me Jason at presence pg. com and we have, you know, go to our website. We have all kinds of blog posts, but I'm happy to talk with people directly as well.

Tim Butara: Awesome. Awesome. We'll make sure to include that in the show notes.

And Jason, thanks again for coming to the show today for sharing your insights, your lessons with us again. It was great having you here. Yeah, absolutely. My pleasure. Thank you. And well to our listeners, that's all for this episode. Have a great day, everyone. And stay safe.

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