The bouncer at the door is you from a hiring standpoint, of how good the club’s going to be on the inside. You have to pick the right people to come in.

In this episode

Do you ever think about the importance of the types of people your company hires?

When hiring, many companies focus on the experience of their candidates. While this plays a large role, who a person is and their level of entrepreneurial talent could be even more important. 

Jason explains the nuances of hiring the right fit for your company, breaking down the distinction between generalists and specialists. He also shares how to get your company ahead by leveraging AI and developing relationships with your competitors. 

Jason Smith is a product driven, sales and marketing centric tech entrepreneur. He has been the cofounder, investor or early employee of 5 start-ups. He’s led sales, marketing, product and services teams, advised great companies like Mobify (acquired by and Strutta (acquired by LX Ventures) and received E&Y’s Emerging Entrepreneur of the Year for the Pacific Region. He is currently the CEO and Cofounder of Klue, an AI-powered Competitive Enablement platform.

In episode #165, Jason shares his experiences as an entrepreneurial leader to help you delegate, hire and manage better.

Tune in to hear all about Jason’s leadership journey and the lessons learned along the way!

Like this episode? Be sure to leave a ⭐️⭐️⭐️⭐️⭐️ review and share the podcast with your colleagues.


Delegation reluctancy


How to know when to have a tough conversation


Hiring entrepreneurial people


Ambiguous interview questions


Looking at a candidate’s past


Develop relationships with your competitors


Company-wide AI day


Being the bouncer of your company

Resources mentioned in this episode:


Jason, welcome to the show. 

Jason Smith (Klue)  03:02

Excited to be here. 

Aydin Mirzaee (  03:05

Yeah, really excited to do this. I mean, you and I have known each other for a number of years now, I’ve always really enjoyed our conversations, you always have so much wisdom to impart. So I’m glad we get to do this and press record. So you obviously have the, you know, extensive management and leadership career worked at companies like Columbus group guy, ultimate Elida, which was formerly vision critical today, founder and CEO at Klue. So lots of different experiences that we’re going to touch on. But as you know, we always like to start with the mistakes. And so do you remember when you first started to manage and lead a team? What were some of those very early mistakes that used to make?

Jason Smith (Klue)  03:56

Alright, is that the entire podcast because we could just keep going on the mistakes that were made. Because my first business was straight out of university and founded with two of my best friends, that’s always a good idea. So we had no idea what we’re doing. So it was a bit comical on that. I think, you know, at that stage, when you’re 23 trying to build a business, there’s, there’s so many management errors that you make, and it was so just context. Columbus group was a web services business. And so every time we landed a couple more clients, we would add more people. And so when you add more people, you’re naturally having to manage and lead those people. And 23 you do it in the way that you think you should, which is basically you doing everything yourself and not letting anybody do anything. So we call it delegation. reluctancy is probably the number one mistake and it’s probably true of most early stage founders where you’ve got this. You’re used to doing everything. You’re used to probably doing it better than anybody Eltz could do it. So you have this trust issue, when you’ve got great employees coming in and letting go and letting them make decisions, make mistakes. And you instead of doing it are providing guidance and input into that journey of decision making. And certainly in those early days, I was not sophisticated enough to think about proper delegation. It was like, What’s your thought? Okay, here’s my opinion, we’ll do that. Right. Was comical. The other thing that I actually find interesting was, those tough conversations that are pretty easy to have now, you know, five startups in were very difficult early on. And they were hard conversations that you needed to have, if there was always an elephant in the room that would crop up and they’d be small in the beginning, and they turn into big animals. And if you didn’t have those conversations, it would create blockages for the entire company. So avoiding those hard conversations, thinking being nice was the right way to be. And instead, I should have just attacked, you know, some of the issues right off the bat.

Aydin Mirzaee (  06:02

I’d love to dig in there. So on the delegation thing, so I am curious. So like you said, five startups, and you’re very well known founder had lots of successes, but five startups and do you ever make the delegation mistake again? Or do you think like, this is something that you do really well, you know, you hire someone new, trust Him fully give him everything? I’m just wondering, like, is it a spectrum? Because this is something that people talk about? And I feel like, even though the broad lesson maybe makes sense, maybe you still make the same mistake, but maybe in a slightly different form? Like does it ever go away? Or is this like a lesson that one keeps learning? Like, how do you feel about from from the delegation angle? Or do you feel like now, for the most part, you’ve mastered it? Like, have you think about that? Yeah, I

Jason Smith (Klue)  06:46

think it’s definitely lifelong learning. I don’t think whenever masters, I think what you do get is you get more sophisticated in how you communicate, and how you share opinions in a much more contributor way than a directive way. And so that’s something I think you get more elegant at over time with more and more interactions. But look, the reality on startups is you can’t afford to hire the best and most experienced people in every position. So you are going to have this delta, on folks that are really effective in a role and those that maybe are new, or generalists in a role that need some of that guidance. And so they might be smart. And so you want to lay the breadcrumbs for those smart people. But I think there is the spectrum of dictator and almost like reckless delegation where you’re just letting people flow on their own. Somewhere in the middle, there is that contributor, that guidance where you’re asking some of the right questions, because you probably have some experience across some of these spectrums. And so you’re asking, have you thought about that? Are there new variables compared to the last time that we might have tried that? What’s your perspective? You’re asking all of those may I know better way, you’re asking it in a purely curious way. And that’s maybe one of the learnings in the early days, I’ve asked the same questions. It was dripped with I know better. Instead of now, it’s much more truly I am curious. There are new variables that pop in, there are different experiences that people have. And I want to learn that and I want to test my own paradigm, my own frame of whether or not I should be evolving. And so once you look at it through the curious lens, then I think it gets easier to provide some guidance. One last thing that I think for us, you know, a Klue one of the I use the term grenades, CEO, grenades, founder grenades that you you have a handful that you can pull out. But if you keep throwing grenades all the time, it really is a warzone. But every now and again, it can keep people on their toes. And so I kind of think of myself as having a grenade a quarter that I could throw at maximum, where I feel very strongly about something with that conviction that I’ll drive it through, and really force a decision. Otherwise, you know, at the stage that we’re at with hundreds of employees, now, I have to give people the room to make some of those mistakes, provide the input. And as long as it’s not a material mistake that’s going to blow many millions of dollars. You can let them run and go learn. The smart people want to learn, they don’t want to be told. So yeah, use your grenades wisely as a CEO today and contribute in a very genuinely curious way.

Aydin Mirzaee (  09:26

Let me also ask you about this tough conversation piece. I feel like this is also one of those things that you get better at over time you’re never perfect at. And I’m curious, like, is there a feeling that you have or a way that you know that hey, it’s time for me to have a tough conversation? You know, like, how do you know that you need to have one or that you’ve delayed one for longer than you should have?

Jason Smith (Klue)  09:50

Oh, yeah, it’s this is a great one. And again, we could spend a lot of time on it. I think, you know, certainly I think you develop your instincts better over time through 1000s of hires. 1000s of conversations, multiple startups. So I think, you know, experience obviously makes a difference where you can sniff things a lot earlier, and then know that you need to address them that early as well. So, but clearly lifetime of learning, I think, you know, for me, the instinct is one thing, but I think most people end up having a bit of a spider sense, you know, when it feels a little bit awkward, when it feels frustrating when somebody is not being candid, authentic, genuine. And as soon as you have that, I think it’s your duty and your responsibility to try and get past the veneer and figure out what’s going on. It ultimately will impact your relationship with that person, but it’ll impact the performance of the individual and you if you’re managing them, and overall as the company. So in terms of sniffing it, I think everybody can just trust their spider sense, just that little bit more than this is a little bit off. And whether it’s moving from a group situation to a one on one, hey, I want to have that follow up, I just want to have that discussion. And I found starting being vulnerable myself makes a big difference. I might have been Miss reading this. But this is something that it felt like was there, I’d been in a situation where I felt awkward like that, and I share an example. And that usually sets the stage for an open conversation. But the other thing that you know, I do now and and struck a lot of folks a Klue to think about is candidness is a core part of a lot of company cultures today. But it’s one thing to be candid, in a very direct way without care and curiosity. If you’re candid, without that sense of I care about you, and I’m genuinely curious about you, you’re a jerk. You’re just candidate as a jerk. You can be honest and direct and hurt people. But if you have you proceed that candidness that direct conversation that you think you need to have with some level of care and genuine curiosity, then people are game, they’re usually for it. I’m curious, and why are you thinking that? And what was it about that, like, I helped me understand it. And people can tell when you’re dripping with sarcasm on that, or you’re loaded, and genuine. And I think if you can come at it from that genuine, caring curiosity proceeding candidness the whole world opens up.

Aydin Mirzaee (  12:23

I love that. If you’re just candid, you’re a jerk. But if you’re a candidate and curious, and people think that you actually care, because you do, that’s a different way to approach it. And I agree that that does make a whole world of difference. You know, Jason, this isn’t part of like, the usual set of questions. But one of the things I have noticed about just because we haven’t known each other for a while is it seems like you you’re just very thoughtful. Right? And so you when you do respond to things, or when you do opine on things, it’s clear that you’ve done a lot of thinking, and you’ve thought things through so my question is, do you have a reflection process? Or do you do some sort of journaling? Or is there anything that you rituals that you have in place that allow you to, you know, holistically look at what’s going on, maybe in your style of doing things or the way that the company is going, you know, how do you generate insights for yourself,

Jason Smith (Klue)  13:17

number of things, I’m listening to smart people like you and others on your podcast to make sure that I’m elevating. So there’s inputs that you’re going to get from a variety of different people. And you’re going to take different elements of what you learn in those or a direct manager experience and kind of choose what you get. But in terms of like micro habits, and little things, but one thing that’s really made a difference for me is I would often wrap a meeting, and have thoughts and not get them down, think that I’m going to get them down later. And recall that information. And then you know, by the end of the day, you’ve kind of lost it. And so I’ve really become strict about posting a meeting or writing my thoughts, and whether that’s to myself and a note, or whether that’s directed in a Slack combo to others inside the company. It’s very much like I want to get my outtake of my perception of what it is. And that can create a frame for me to kind of now jump off of our board that I can launch from another discussion on. So it’s a simple little app. But truly it is at the end of a conversation with somebody, whether it’s somebody you’re learning from or whether somebody you’re managing, you’re going to have mental thoughts that need a place. And I note those down and come back to those and either share them directly, or tune them before sharing them with the team.

Aydin Mirzaee (  14:37

Yeah, I mean, that’s a good tactical hack, and we love those on the podcast. So thank you for sharing that. I also want to talk about hiring. So again, you’ve hired hundreds, maybe more than 1000 people, lots of people and many acts that in interviews, so you’ve had a chance to seeing what’s worked, what hasn’t worked. And so what have you learned about hiring and maybe we can think about it actually like the early stages of when you’re starting something new. And I know that people might think, okay, that’s mainly startups that start something new. But new teams formed all the time, new departments form new products within companies. And yeah, what have you learned about just hiring people that really help organizations in those early stages?

Jason Smith (Klue)  15:20

Yeah, there’s I mean, there’s, there’s a lot in the earliest stage, you know, you know, from startup land, you’re either building the product or the service offering, you’re selling it and marketing it, or you’re servicing it, it’s kind of one of those three cores. That’s in the early stage startup. As you mature, though, the evolution of generalist hiring to specialist hiring is another big change, right. So in the early days, I’m constantly looking for jazz musicians. Those generalists who are comfortable with ambiguity they see around corners are willing to jump in, they’re willing to own it, they might not know, they’re almost leaping before they’re looking, but they’ve got the ability to pick up the tune and run with it. And I think that’s super critical in the early days of whether it’s a new department, or whether it’s a new company launching, you need the generalist, and then you know, as it matures, you’re looking for more of the specialists, you’re looking now symphony, you need the pros that know how to play that specific instrument, and you get better. And you know, I don’t know where that perfect line is where the hundreds of employees, but you’re going to layer in more of those specialists in around the generalist, and then you start to see the shortcomings of the generalist, as the structure of the company gets more and more defined. And the people that Excel are the people that excel in that structured environment, it becomes pretty natural, you can kind of see it, but those early days, you got to have the jazz musicians that can pick up a tune, I got that beat, let’s roll with it. Yeah, maybe that maybe that. And it’s an idea. And it’s more iterative. And there’s this like unknown that they’re willing to jump into. And very few specialists are really good at that are keen on that even they’ve got a historical reference point. This doesn’t look like what I’ve done before. Now I’m a little bit awkward. Who do I talk to generalist and early Day Startup people, much more entrepreneur. Now. I’m a core entrepreneur, five time entrepreneur, I can’t help but want to hire entrepreneurial people. So no matter what I’m looking for those folks that are just going to try and see around corners and problem solve. And there’s you know, now I’ve got fairly specific hiring criteria they look for, for individual relative to the rule, there’s kind of two different sets that we look at.

Aydin Mirzaee (  17:27

Yeah, and I remember this one time, I was I think I was hiring for a sales role or something. And you were like, Oh, here’s my list of questions, and like my mental model and framework for like sales roles. And it was really awesome. Are there any generic things? I mean, you said, it sounds like even though you might look for specialists, you’re looking for maybe an entrepreneurial specialist or you appreciate those sorts of qualities. Yeah. How do you test for that? Like, how do you know that someone has that?

Jason Smith (Klue)  17:54

Let me just back up. Because I think the thing that I’ve now come to I’ve kind of distilled some really core attributes that I find are required for the types of businesses that I’m running, I actually look for the cognitive agility or just plain smarts now i skew towards that cognitive agility, how quickly can they move and adapt to some of the thinking that combined with resilience and grit, you know, you’re looking for something in their past, or how they approach problems without resilience and grit. And then, you know, the third set is kind of their ambitious achievers, they just want to do more, they want that 1% better every day. And you’ve seen that reflected in their career or even how they’re asking the questions. So that curiosity lens will kind of flow through all of that. I’m very curious about what you’re doing. I want to understand it and the last five more questions, and then how that one person is getting better. What could I do in here, and you can just see it in some of those early people. This other maybe the fourth thing that is kind of like the sub context, it’s really critical for me is I want to get past the veneer, I want to know the person. And some people are just too damn polished, and I can’t work with them, I need to know and feel who they are. So I’m looking for that genuine, authentic self to come through. And if I can’t get past the veneer, I’ve got this weird motion of like, do I truly trust them? And so you know, some people are very quick to have no guard, and they are who they are. Other people are well groomed. Salespeople in particular are very good at saying what needs to be said. So poking at that real person and understanding them. And usually what I do there for all of these things, the smarts, the resilience and the ambitious mindset, because I’m throwing ambiguity at them. Now, hey, how have you approached this one particular element in your career when you did that, that looked like it was something new if you’re going to come into this company, there’s going to be this new space that you’re into, we’re building this new category, what are your initial thoughts on that? And you start to see people kind of run with that ambiguity in a way that either is a step back, let me take some time a theoretical construct shirred or just jumping into it and kind of rolling in, you can see them unravel their brain in front of you. So I’m constantly asking questions that really aren’t that crisp. They’re leaving out some pieces and they’re jumping to maybe some conclusion. I think what you mean by that, Jason is this? If that’s the framing, then let me answer it this way. I love kind of leaving half questions that might not be fully clear, we’ll stumbling over how I’m asking the question so that they need to create that That’s one of the pieces. Yeah,

Aydin Mirzaee (  20:34

yeah. So four really good thing to look for? And is that how you test for cognitive agility? Is that what you mean for people to be able to solve in ambiguous situations and, you know, when things aren’t clear instructions aren’t clear for them to be able to just piece things together and figure it out.

Jason Smith (Klue)  20:51

It is an it’s like, literally purposely ambiguous questions that maybe aren’t crystal clear.

Aydin Mirzaee (  20:57

Can you give us an example? Like, what’s an example?

Jason Smith (Klue)  21:00

An example might be looking at your past and saying, so, you know, you came from this this area, you might have had a, you know, a struggle of how you’re doing it? And how did that struggle get reflected in you your approach to how you might think about joining a company that’s building a category? And it’s kind of like an all over question where they’re kind of going, Well, what I’m trying to get out here, and the people that I find, you know, with really good commentary are kind of connecting that going, I think what you mean is like, how am I going to be able to jump into that company and run, when there’s a lot of ambiguity with the company itself, or this category that you’re building? And, you know, and I struggled in the past with that, let me give you an example. They run with it, others are like, they make a guess. And it’s just completely off, you know, and they’re like, oh, right, you want to talk about when I, you know, had trouble in that classroom. And I know, that was in it, I was kind of meandering to this other thing. So it’s, it’s seeing how well they can kind of piece together enough of the ambiguity of the question to get at what I’m hoping to get at. And honestly, a lot of that’s in the flow of looking at their history, and how it might connect to you know how I’m seeing Klue.

Aydin Mirzaee (  22:17

Hey, everyone, just a quick pause on today’s episode to tell you about a new feature that I am so excited about, we’ve been working on this one for quite a while, and excited to announce it to the world. We’re calling it meeting guidelines. So there’s all these things that people already know they should do when they organize a meeting. So for example, you should make sure that you shouldn’t invite too many people or if you’re booking a recurring meeting, you probably want to put an end date on that meeting. Or if you’re going to invite someone to a meeting, you should probably you know, if they have more than 20 hours of meetings that week, maybe be a little bit more considerate, and ask Should I really invite that person to the meeting. So there’s a bunch of these sorts of things that you might even know about. But what happens somehow in larger organizations, is that people forget all of these things. And so that’s why we built this feature called meeting guidelines. It’s super easy to use, it’s a Google Chrome extension. So if you install it, what will happen is it will integrate with your Google Calendar. And that way, whenever anyone within your company is about to book a meeting, these meeting guidelines will show up and make sure that people know and take a second look at that meeting that they’re about to book and make sure that it adheres to these guidelines. So if you want to book or within your company, have a no meeting day, or if you want to make sure that every meeting has an agenda in advance before it’s booked. So all the different sorts of guidelines that you may want. And they’re all obviously highly configurable, because every company is going to be slightly different. But this is the first time that there is a way that you can get an entire organization to change their meeting behavior. It’s something that we’ve been working on for a very long time, super proud to announce it to the world. It’s called meeting guidelines. If you’re interested in checking it out. We’d love for you to do that and give us feedback. You can get to it by going to Again, that, check it out, and let me know what you think. And on the grip piece, you know, give me an example when times were really tough and you just didn’t give up or like how do you tease that out?

Jason Smith (Klue)  24:32

Yeah, I think you know, there’s maybe some biases and shortcuts there. You know, I love athletes that have gone through you know, a lot of challenges rejection had to get up and do it again. There’s people that have done things in their earlier part of their career. I always start interviews in hiring with just almost like the WHO method just tell me walk me through your your background. You were born on a farm where you know, let’s start there. And they’re like, Whoa, really that far back and and I really just want to see their journey and you Usually, within that, you’re gonna hear something about, you know, the hardest thing they did was, you know, teach tennis, you know, that probably doesn’t compare to, I was an immigrant that landed here. And I made no friends for the first four years in school. And I had to figure out how to, you know, come through that. So I jumped into my studies here. And one of the jobs that became open to me where I can make a lot of money and put myself through university was pre planning, and I figured out how to plant over 3000 trees a day, you’re hearing that and going, okay, that’s very different than maybe the person that hasn’t gone through any of those challenges. Now, I don’t preclude the people that haven’t gone through those challenges. Sometimes you can kind of dig at them a little bit and just see that they did have challenges in a different way, and how they’ve approached it. But what you’re looking for is that push back that strength of like, yeah, I went through some rough stuff, and I figured out some things and I can go at something and I can be pushed down and I’ll get back up, not in a chip in the shoulder way, just I have confidence in myself. And so historically, you’ll look for going way back what they’ve done in their career in their life and look for those little threads.

Aydin Mirzaee (  26:07

Yeah. And I think what’s the most interesting part about this is you’re optimizing for the type of companies that you are building, which are early stage, but also category building doing a thing that people didn’t necessarily buy before. It’s like a new way of doing things. So all of these things are the, you know, the pieces that people need to be successful at those types of companies. And it’s really cool that you’ve put that together. And I think like this probably fits into that, which is just on the notion of being able to think big. That’s obviously something that that you practice, but can you talk about that in terms of, you know, how that materializes? In the team that you hire?

Jason Smith (Klue)  26:49

Yeah, I think there’s, you know, so this is, so I’m a Canadian entrepreneur, I’m based in Vancouver, I grew up in Toronto, you know, my first business, I was pretty excited about getting, I don’t know, BC Hydro as a client instead of Verizon. And, you know, I didn’t think Verizon was in the realm of possibility. And what I’m constantly trying to do with my current set of employees, forget even about hiring that but looking at how do you expose your current employees to think bigger and elevate is demystifying Verizon, it’s demystifying the people that are doing big things. And that can start by just listening to them, there’s a lot of podcasts and reading their tweets, and watching videos, and that kind of thing that can give you exposure to their brain and how they’re thinking, and then literally reaching out to some of those people that are at the top of their ladder in whatever position and what they’re doing. And you’d be surprised about how many of them would actually give you a bit of time. And if maybe not the top, it’s the next top. And so I found demystifying these people that are thinking bigger, you know, it’s pretty hard to get a conversation going with Elon, but there’s other people that, you know, might be, you know, connected Elon and exposed to that thinking big and have gone into it that you might have that conversation with. And as soon as you have the combo, you realize, okay, they’re super smart, they’re ambitious, they’re motivated, they’re doing all these things. But I’m not that different. Maybe I can, and as soon as that switch turns in people’s heads that maybe they can, then they start seeking again, if they’re smart and ambitious, if you’ve already got those core characteristics, they’re smart, and then they’re seeing, Oh, maybe I’ll look for that one little thing. And I’ll try that little thing. And it opens up the realm of possibility of maybe me, maybe I can do, I’m from a small town, but maybe I can do it. And it’s just exposure, I think, to the people that are already doing it, and realizing they were kinda like you.

Aydin Mirzaee (  28:43

So if there’s someone on your team, and you feel that they should be thinking bigger, what do you do specifically? Like, what’s the example of what you might do? Or tell them to do?

Jason Smith (Klue)  28:55

Yeah. And so like, literally, I start with, like, Who do you think the best is and what you’re doing, if you’re a salesperson who’s the best in the world, salesperson, what’s the company with the best salespeople in the world? Start by going to research those people or those companies. And that could be again, just following on Twitter, it could be or acts, it could be podcasts, it can be videos, it’s just exposure to how they’re thinking and how they’re talking and absorbing some of that insights, kind of like what you’re trying to do in the ScrumMasters. Like, you’ve got the sense of like, exposure to people that have done some things. The more people hear that the more they take some of these tidbits and go maybe I can do that. But to me, the next step is reaching out to some of those people to actually talk to them, see them, see them live, be part of it. And you know, for better or worse, the Bay Area is still is the magnet for you know, probably some of the most ambitious big thinking people in the world. And so you can go to conferences in the Bay Area. You can have coffees, you can have one on ones you can reach out there’s a lot of Pay It Forward mentality in the Bay Area. So once you start getting exposure through a one way medium, you move to the second, which is reaching out and physically being in the presence and talking to some of these people directly. And again, that totally starts to demystify the god status that those people might have in your head, and you start to think that they could do it. So literally, it’s exposure, its exposure to the bigger thinker, starting from listening podcasts through to then being in person and trying having one on ones.

Aydin Mirzaee (  30:29

Yeah, that’s really good advice and a good way to do it. The other topic that you know, I also have to talk to you about is just competitors. And obviously, Klue is a competitive intelligence platform. This is your bread and butter. This is what you do, what you help your customers do. But I wanted to maybe start with something that I’ve learned about you, which I find is different. And not everybody does it this way, which is, you like to actually talk to your competitors and actually get to know your competitors, whereas other people may not want to do that you’re potentially enemies. And so why do you want to talk to your enemies, maybe they might learn something about you that you, you accidentally let slip, but you’re very candid about it, and you just go meet them and talk to them. So maybe you can talk to us about just like how you think about competitors to begin with,

Jason Smith (Klue)  31:20

you’re just picking up on that threat. I think it’s an absolute, I mean, if you went to a conference, and you physically sat next to your competitor, or you’re not going to talk to them, you’re going to talk to them, and you’re going to talk about a mutual competitor. And you’re both going to share insights, and you are going to connect over that mutual competitor or a market view, the irony of not reaching out to competitors, his that they know everything that you know, but from a different lens. They’re the most knowledgeable, they’re probably the people that you could relate to most in building your category. And yet, you’re like, No, they’re the enemy. And truly, you want to beat them. But that human knowledge sharing is often far greater. And so clearly, when I speak to my competitors, I’m relatively evasive of sharing what I’m specifically doing, certainly relative to them, they’re going to be the same with their own. But we have common ground on things like mutual competitors, things like investment, things like growth, things like growing the category, things like approaches to where non competitors, but potential incoming competitors, if we grow, the category could come in. And so there’s so much common ground that you can have your competitors, that I just think it totally makes sense to reach out to them and develop a relationship. And then when other pieces, depending on how you grow relative to them, you might find them. And so it’s a really good idea to get to know those founders in advance of doing that, or people on their team in advance of doing that.

Aydin Mirzaee (  32:53

And so is this something that you as the CEO and the founder do? Or like, do you recommend your VP of marketing to do that with VP of marketing spin competitors? Like how deep does this go? What do you recommend there?

Jason Smith (Klue)  33:07

Yeah, that’s interesting. At our company, it goes all the way through. So like, literally, we have people all the way through the ranks reaching out to different competitors. It’s not something that we’re focused on, it’s just, if they do something interesting, we might reach out and say, Hey, that was a really interesting thing that you did inspiring. That’s great. Hopefully, it helps build the category. Like there could be those types of reach outs at the VP level. I don’t know about at the you know, the junior level, you know, I don’t think STRS are reaching out, I don’t think you know, first time CS person is, but certainly at the director VP level, we have, you know, a lot of common ground. Are you going to that conference, we are you like you actually want some of your competitors there. So we’ll do that.

Aydin Mirzaee (  33:53

Yeah, that is super interesting to when a competitor does something well to tell them that they actually did that. Well. I mean, that’s, I mean, you know, it’s very sportsman like, and it makes sense when you think of business as a sport. And yet, but for whatever reason that framing isn’t maybe the first place that people go to. So thank you for explaining that in that way.

Jason Smith (Klue)  34:15

It’s like an MMA fighter, like you are going to be in the ring, and you are going to want to win. But you get out of that ring. And like that MMA fighter just like you is a fighter, and like, that’s your living. And so you connect on a lot of those fronts. But make no mistake, I want to beat my competitor very badly in the ring. But I still think you can do that and be respectful of what they do.

Aydin Mirzaee (  34:38

Yeah, that makes sense. So Jason, the other thing that is very topical these days and I know you’re focused on it is everybody’s talking about generative AI is changing the way that everybody is operating people are building it into their products into the ways that they sell and market and develop software, everything. And so maybe we can talk about You know, what are the things that you’re doing and things that you have learned and the ways that maybe you have incorporated it into your style of leadership?

Jason Smith (Klue)  35:09

Let me separate the AI trend into two buckets. One is, you know how it impacts my product. And at the end of the day, our product is trying to find signal and a bunch of noise that exists from many, many data sources. So clearly, like ML has always been a core part of Klue. And now you know, large language models and how genetic is working gives us kind of a boost and accelerator on the product side. And I think every company is probably looking at how to get a boost from API’s that they can plug in and leverage large language models. And Jenny, I’m certainly we are, we’re deep down that path, we’ve already launched a number of features, we’re probably not going to build our own specific LLM. But take something that can be controlled, and then add, you know, proprietary data on top of that, that could be beneficial for our particular use case, and competitive and market and buyer insights that’s on the product side. But there’s another piece like we held, we did a company wide AI day. And what this was, was just trying to create the room for everybody in the company to go down the rabbit hole of different AI tools, everybody’s kind of played with some different, or what everybody would catch a tee, but probably some other AI tools, more and more tools are baking AI into but there’s a whole bunch of Gen AI pure play startups that could be quite interesting, whether it’s writing or whether it’s presentation layer, or whether it’s analytics, there’s a number of pieces that you can play with. The problem is, it’s a bit like the iPhone in the early days, where you’ve got a million apps for flashlights, and you know, which one is it. And you know, the OS is probably going to build in the flashlight in the future. So you’re like, oh, how much time do I spend on this, and there’s the same thing is happening, I think in the world agenda, there’s all of these new applications, you don’t know which one’s gonna win. There’s a whole bunch of marketing veneer, and you have to get through it like all products and understand doesn’t truly provide the value. And so I wanted to create room for our employees to do that. So we literally just blocked off an entire day, we built our own software, we use coop cards to actually illustrate these are the things that we found. People were voting on different tools and sharing that and had this very vibrant Slack channel through the day, did you see this back and forth. And it resulted in like this list of roughly about 100 tools that we’ve come across now where we’ve all spent a bit of time on these different tools. And now that’s kind of our repository of like, Klue reviewed, AI tools that we think might have legs. So it’s a shortcut for a lot of others when they think, what’s the presentation tool? Oh, there’s three that a whole bunch of people have reviewed already. I’ll start there. It’s kind of like your intro library. And so I truly encourage every company, every manager to dip into that and try and find space, because there’s a bunch of wasted time of like, that tool wasn’t any good. And you’re probably going to look at five before you find the one you like. And from a manager standpoint and like I’m just like, which employee Do you want the employee that says, I know how to leverage these five AI tools that are going to make me way more efficient, or the one that says I haven’t really used those tools. So you’re clearly going to want the one that’s kind of creating an AI system for doing things more efficiently. So it’s not only important for my company, it’s important for individual careers.

Aydin Mirzaee (  38:18

Yeah. And is there a way that you are encouraging this on a ongoing basis. And the reason I say that is because obviously there was a lot of hype early on. And there’s still a lot of hype. But as with any hype cycle, I feel like the hype will go away. And maybe a lot of people will go back to normal and their old way of doing things. And I do think this time is a little bit different than anything we’ve seen before. But it’s just is there like a constant almost like an OKR or something that you have in place, which is maybe getting people to think about the way that they do things differently, maybe there’s different ways to sell are different ways to market or, you know, something that allows people to keep getting more efficient using these tools.

Jason Smith (Klue)  39:01

So I think my hope, and I’m still early in this journey right now is that we’ve created a spark that created some experimentation and investigation and created some collaboration and sharing across different things that might be valuable. And the taste of productivity that you can get with some of those tools, creates the reinforcement loop to say, Ooh, there might be something else that gets my job done faster. That is beneficial for both the company in my personal career. And I’m starting to see those dividends right now. So literally, I think you need to force function it with time dedicated, like block off a day, all meetings, create something that gets everybody down this path. And now what I’m seeing is, you know, that’s the rock starting to roll down the hill and gather steam. So from that standpoint, TBD. If it’s not going to be sustained, but like think your phone, like do you scroll through to the eighth page on your phone and look at those apps anymore. Like it’s whatever apps end up on the first So I think we’re in the download a ton of apps moment experiment like crazy. Pick up your friend’s phone of going, what cool apps do you have, and create that inspo collaboration, sharing? Maybe I’ll try that it works for you. It doesn’t. And you know, when in very short period of time, I think we’ll end up with that one screen have apps that are beneficial for you personally. And that’ll be true of kind of the Gen AI apps.

Aydin Mirzaee (  40:23

Yeah, it always seems things in tech, it’s always the winner takes most so you make it on the home screen or you don’t. So there, Jason, this has been an awesome conversation, we started talking about delegation, tough conversations. I love the just the idea of being candid and curious. At the same time, you had your hack about writing things right after the meetings, the thoughts and insights, you recorded, the four things you use in order to hire and of course, we also talked about AI, which is awesome. And of course, your view on competitors, which I think is a very refreshing view. And everybody can learn from so the final question that we like to end on is for all the managers and leaders constantly looking to get better at their craft any final tips, tricks or words of wisdom that you would leave them with,

Jason Smith (Klue)  41:10

maybe I’ll circle back to kind of the hiring, I do think that moment of the bouncer at the door is you from a hiring standpoint of how good the club’s going to be on the inside, you got to pick the right people to come in. And so from my standpoint, you need to be very clear on the cultural and values alignment, super clear on the expectations in the workplace that they’re going to join. And literally in many cases, try and talk them out of it, particularly in early stage tech companies. There are way easier jobs, there are ways your jobs than joining a high growth tech startup, or a struggling startup that is not got the next round of funding yet or has some challenges. I think you need to be really clear on that. And the right people will self identify on that and go no, actually, that’s what I’m looking for. I want to challenge I want to work with, you know, highly ambitious people that might not make it on this product or this company. But I want the shot. And so I think when they fully opt in to that, you know, expectation reality, they walk in and days one through 60 On that first kind of onboarding. They’re like, Yep, this is what I expected. Okay, this is our part. And they’re approaching everything with a can do instead of what we were what I thought this was going to be a little bit easier. So that cultural values, alignment, very clear expectations about the workplace are joining I think is critical. I’m a big fan of the no rules rules. Reed Hastings book, I love that there’s probably 80% of the things in there that I totally agree with that kind of really kind of put forward the idea of being candid and clear about the workplace and the expectations that they’re joining ahead of time.

Aydin Mirzaee (  42:46

Yeah, Jason. That’s great advice and a great place to end it. Thank you so much for doing this. And that’s it for today. Thank you so much for tuning into this episode of the Supermanagers podcast. You can find the show notes and transcript at If you liked the content, be sure to rate review and subscribe so you can get notified when we post the next episode. And please tell your friends and fellow managers about it. It’d be awesome if you can help us spread the word about the show. See you next time.

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