SaaS Management at All Stages | With Expert Adam Berke

You know, specifically for SaaS, you know, so we talk, it's kind of like a broad topic, you know, 80/20 on how you approach it, but You know, you also have specifically SaaS, you have, you know, security, you have onboarding, you have team management on, you know, you mentioned the one-on-ones. How do you guys at your team, you know, help in those, you know, maybe those different stages of the operations, or is it just kind of specific areas that you guys—

Yeah, I mean, like, yeah, I mean, so like, you know, an example of thing that might, that might change is maybe the cadence at which you do goal setting, right? You know, in the earlier stages, let's say you are, you know, 4 or 5 people maybe, or, you know, you're just starting to get your first, uh, non-founder, uh, employees. Um, yeah, you're not gonna set annual targets. Uh, that would be, you know, those would be out of date in, in a month or a week. Um, so, you know, the way we think about it in our product is we want to let that be very flexible. And, and again, I think that's a problem with some of the products that we got from our, uh, you know, HR team in the past that were very rigid. And it's like, okay, you're gonna do this quarterly OKR process, you know, very bureaucratic. You know, very heavyweight. You know, we want to— we think goals are a great thing, but we want them to be lightweight and quick and flexible. So, you know, it's very rewarding to achieve goals, so you shouldn't have to wait, you know, till the end of the quarter or whatever it might be. And probably that's the wrong cadence, especially for earlier teams. So, but, but still having monthly or biweekly or things like that, you know, if people had a goal-setting product that they could spin up quickly, And not have to, you know, enter a bunch of different fields, but just have something as a quick marker to track their progress, that can be really tangible and really rewarding. So, you know, again, having some sort of intentional system, always beneficial. Like, you don't want to be having to— I make this probably poor analogy to the, like, apocryphal Steve Jobs turtleneck where, you know, he wore that. He didn't want to have the mental overhead of choosing his wardrobe. Management is sort of similar. If you can take the mental overhead of having to remember to give feedback, check in on a goal, give recognition, you know, of course how you do that needs to be human, but having the reminder to do that is something— is a great thing to take mental energy kind of off your plate so that you can be more human in the actual delivery of the feedback, of the recognition, whatever the case may be.

So just, just before stepping back, before you get into actual management, I think, you know, more important is, is, you know, bringing on the right people. And I imagine, you know, you probably saw this at AdRoll, right? You have to have an all-star team if you want to build a world-class kind of product and, you know, scale as big as you guys did. Um, so when it becomes— when it comes to actually developing or building that highly effective team, do you have any kind of general best, best practices that you, you've kind of, you know, had in the past, or maybe you're, you're, uh, you know, implementing today as well?

Well, you know, I'll say, you know, and this is, this is not something that I necessarily— that we've necessarily perfected, but just something that I've observed, um, and it's a hard habit to break, but, um, not over-indexing on domain expertise is a big one. Um, so it's very tempting, you know, to use, uh, like domain experience that this person worked at a similar— in a similar— at a similar company or knows the space really well. Um, as you know, because there are so many people out there, and especially as people are now recruiting from across the country more frequently, um, it's just the talent pool has become much bigger. And so you, you need ways to kind of shrink, uh, shrink that, uh, uh, pool down. Um, but, but time and time again, I've had to relearn this lesson that, you know, super high, uh, performing people, they are going to be successful, you know, almost anywhere you drop them, um, in many respects. And so, you know, it just so happens, you know, if you can find a top performer in your domain, like, that's great. But, but often, um, that's not the case. And, you know, if you can find, um, the folks that might be coming from a different space, not only, um, will you— are you, are you maybe able to find like untapped talent pools, but you're also going to bring, um, perspectives and learnings from other categories, other industries. And, and, you know, as we all know, like That's kind of where the magic ends up happening. Like, it's hard to, you know, if you are in a startup environment, it's going to be really hard to like out— just out-execute incumbents. They have more, they have more resources, they have more people, and they can, you know, sort of just like cloud the sky with whatever it is they're doing in their message. So, you know, it's almost like an imperative that you find a different tack, find a different angle. find a different, you know, line of attack. And that's just more likely to happen when you have people from outside the industry. Like, this is like, again, I'm totally recognizing this is hard to do because there are so many people.

Of course.

And so if you just, you don't narrow it by anything, then, you know, you're just gonna be overwhelmed. But I think to the degree that you cannot, you can avoid the temptation of dismissing at least an interested employee or someone who you like, but like, oh, do they really know the space? use that as a red flag and say, oh wait, wait a minute, let me not dismiss them because they don't know the space. That usually ends up not being a good reason. And I've seen time and time again, people come into an industry from like even a fairly seemingly unrelated one, bring new ideas, bring a new slant, and then crush it. So yeah, easier advice to give than to follow, but a lesson I've had to learn over and over again.

Okay, I want to drill into that just, just kind of a little bit deeper. So, um, for example, your first— I would say your first 10 employees are probably super important, right? Because that builds kind of the strong pillar of your team. I imagine, you know, you've been there recently. Um, if you have kind of, you know, you're trying to build up that team of top talent, you have 2 options. One is, you know, highly experienced, maybe, you know, with or without strong domain expertise. Then you have somebody maybe with less experience, but they have that that grit, that hustle, they're interested, they're committed, maybe they have the soft skills, but you can maybe possibly develop them into potential being part of that kind of core group. How do you look at those both options and how do you generally approach that?

Well, I mean, I think of it as a portfolio and it is a team. And to use a probably overused sports analogy, but any team has people that play different positions and play different roles. And if a if it's a football team, either version, American or European, like, you know, if all you have is like, you know, super fast strikers, like, you know, you're not gonna have any defense and you're gonna, you know, you're gonna get scored on all the time. So you need, you know, you need people with different skill sets. And so I think the, you know, the goal of like team building is recognizing what your team needs at different stages and finding those things and understanding where you're weak and looking critically and in a self-aware manner at, you know, what your own personal strengths and weaknesses are and what gaps, uh, that you might need to fill. Um, so yeah, I mean, that's how I would, I would think about it. And like, you know, and then just to like go to the initial premise, like, yeah, the initial team is super important, but like for the same reasons that the job changes as you scale, um, your team should probably change as you scale. And the, the, the roles that people have should change as the company scales. And I think some of that stuff needs to be a bit destigmatized. And because that might mean like, it's just like, if you're growing fast, the company is an entirely different company every year. So why should you assume that just like, oh, well, I'm in this role, I should just stay because the name of the company has changed, even though the role, the need, the organization has totally changed around me. And so, you know, I think some people can adapt and some people want to adapt and are so passionate about the problem space and the way the company is attacking it. And all the things that don't change, that, that, you know, they should take any role that is needed as long as they're still a fit. But oftentimes there's not, and I think that should be okay also. And yeah, and the team you need at different stages is gonna naturally change.

So I'm assuming you've done this, you know, with all your hires you've made, you've obviously made some mistakes or maybe brought on the wrong people. You thought it would be a good fit as part of the team or the football team you're trying to build or the All-Star team. So they're not a good fit, or maybe they're just, you know, struggling. Let's use that word. Um, whether they make mistakes or goals are just not met, you know, continuously based with these employees, how much do you typically like to invest in, let's call it like an underperforming member before, you know, considering replacing them, firing them? And, you know, what's that kind of best strategy there for giving, you know, that balance of more time and effort to improve versus, you know, say cutting your losses and maybe finding a replacement? Do you have any tips there?

Yeah, it's such a hard, it's such a hard, hard problem, obviously. I mean, the 2 things that come to mind on this general topic are that generally speaking, um, people tend to regret waiting too long to make a change versus making a change quicker. Um, generally speaking, um, you know, and, and obviously, you know, this is a difficult topic and it's complicated and, you know, and, and things can, things can evolve with respect to how someone's performing, especially as the company changes and the needs change. But, but generally that, uh, early-ish intuition, you know, not, not at week 1, but at, you know, month 9, um, if you have a sense that it's not working out, that's probably— you're probably— it's probably going to be hard to change because it's probably going to be hard for the other person to change. It's probably going to be hard for you to change. That's one thing that comes to mind. Like, I— and again, I, I, I've fallen victim to this a number of times. And again, it's not, um, it's not necessarily the person's fault, right? Like, and again, this is one of those things that, that's that stigmatize. And frankly, it's probably more often my fault in way more ways, either that I had the wrong skill set in mind, that I didn't well enough understand the person's skill set for the role. I didn't really understand what I actually needed. My management style wasn't right. So, you know, this brings me to the other thing that, you know, that comes to mind. And I just think, you know, if you're— I think it's worth just I think a lot of people view it as, is this person performing well versus are there things that I can change with respect to how I manage them? And that can be easier to change than asking the other person to change, which is like very vague and whatnot. So, you know, I think to the degree you can make an attempt to change the way that you manage them, and maybe that's part of a conversation, asking that kind of awkwardly and directly. Like, you know, is there like— and that is the one trick that I've seen, not trick, but just like tactic, I guess, that can change the course of things. That like some things are simple. You know, I went back to the recognition thing. I fall victim to this all the time. You know, as an executor and operator, I'm, you know, I can be very linear and just, okay, we're gonna need to do this and then this and then this. And just like as soon as we finish something, start moving on to the next and not pausing and not recognizing individual people. And it's amazing how like I mean, such an obvious thing, but having that moment to pause and recognize people can cause them to just have a, just a total change in their motivation, in their commitment, in their interest, and a free thing to give, you know, and as obvious as it is, having that moment to pause can change the course of things.