Ryan Barry
Appcues
Ryan Berry inherited AppQues as CEO after spending a decade building Zappify from the ground up. His first move: ditch the executive assistant and chief of staff to force himself into AI-first productivity. His second: remove almost all one-on-ones from his calendar. The result is a team doing harder work, not busywork.
When Ryan joined AppQues in March, the company was only a year into the Claude and AI agent boom. The ground was moving fast. Instead of assuming the playbook from Zappify would work, he committed to radical observation first.
He spent his first months testing dozens of AI productivity tools, meeting customers, and listening to the team he inherited from founder Jackson Falkowitz. He kept his own opinion formation separate from his market research. One fed the other only after enough discovery happened to know what was right and what was wrong.
This approach came from watching good CEOs fail at transitions. He saw executives arrive at day one thinking they had the answer. That arrogance kills momentum in change periods, especially now when the nature of work itself is shifting week to week.
There’s pattern recognition and there’s first principles. When everything about how we work is changing, you have to keep reminding yourself what’s actually real.
Ryan Berry, AppQues
AppQues’ support team used to spend their days closing login tickets and deflecting basic issues. Now they run advanced technical engagements for customers. Sophia, one of the support engineers, noticed documents were getting out of date relative to customer questions. She built an AI agent to detect and fix it herself. A month later, she presented the work to the entire company.
This is not automation. This is amplification. Ryan was not looking to cut headcount with AI. He was looking to move people from repetitive work into work that matters. Support teams are now among the strongest AI adopters in the company because they see the clearest path to better customer outcomes.
The same principle applies to his own role. By refusing a chief of staff, Ryan forced himself to become fluent in AI tools. He moved his own calendar friction into AI systems instead of delegating it away. The productivity unlock wasn’t in hiring someone to manage his time. It was in rethinking which tasks should even exist on his calendar.
I’m not looking to replace roles with AI. I’m looking at how you amplify people so agents can elevate them by doing mundane tasks.
Ryan Berry, AppQues
Ryan has hired across finance teams, engineering teams, sales teams, and marketing teams. The personalities differ. The operating styles differ. But the traits that separate high performers from the rest stay the same: curious, adaptable, smart, and growth-minded.
Curious means you ask yourself questions naturally. Adaptable means you can follow customer and market signals without breaking. Smart is job-relative. And growth-minded is non-negotiable now.
If someone isn’t self-aware, isn’t trying to improve, and isn’t taking control of their own career and skills, Ryan won’t hire them. This matters more now than it did three years ago because the game changes weekly. People who wait to be told what to do get left behind.
When recruiting his leadership team at AppQues, Ryan didn’t use outside recruiters. Instead, he crowdsourced the search and thought deeply about how different personalities would converge. He wasn’t hiring roles in isolation. He was hiring people who would work well together and push each other forward.
If you’re not self-aware, if you’re not trying to improve yourself, if you’re not taking control of your own career, your own job, your own skills, particularly now, I don’t know what to do.
Ryan Berry, AppQues
Ryan pulled almost all recurring one-on-ones off his calendar. He does this not to avoid people, but to protect time for what matters: customer conversations, market research, and actual product work.
The hard truth he shared: many one-on-ones become therapy sessions or complaint venting. That’s not what a CEO should be paying for. He’s not his direct reports’ therapist. He will help people think through priorities, but the frame matters. The contract needs to be explicit.
Instead, he does quarterly full-day sessions with his leadership team, zooming out on how things are working. For his customer-facing teams, he’s tightened the structure around coaching. Pipeline reviews are formal. Discovery call coaching is explicit. There’s clarity on what the conversation is actually about.
The benefit isn’t just his calendar back. It forces the team to think for themselves. If you know you won’t get a weekly check-in to process, you start making decisions faster. You start owning problems instead of bringing them to your boss.
One exception exists. His VP of Engineering and head of product both value working through priorities with him. They contracted on what that means. It’s not a recurring slot, not a therapy session, just clarity on when it’s useful to both of them.
I don’t want weekly silo creation meetings where I meet with the engineering VP, then the product VP, then the marketing VP. Why the hell didn’t we just get in a room?
Ryan Berry, AppQues
AppQues has engineers in Brazil, Uruguay, and Colombia. Ryan has managed distributed teams before. At Zappify, core engineers sat in Cape Town while commercial people were in Boston and London. The time zones don’t kill distribution. Bad communication structures do.
Chris Brookins, VP of Engineering, creates the rhythm. Two hackathons a year bring the team together to execute on projects. Engineering does documentation well. They’re launching a major product rewrite in July and pulled people in from across the country and world for the kickoff.
Ryan takes his mornings back. No calls before 10 a.m. unless a customer needs him. He works on strategy, thinking, and writing. His head of product, Bernie, does her best work before 11 a.m. So they find the overlap and let async work carry the rest.
When Ryan needed Bernie’s help on something one night, he worked on it while his kids slept. He left comments in the shared Notion. Bernie woke up, saw the work, added her thoughts, and by the time Ryan checked it at 10:30 a.m., they’d made real progress without a single synchronous meeting. That’s the distributed team working well.
The real requirement isn’t location. It’s knowing your team’s work style, respecting when someone does their best thinking, and building the communication structures that let people overlap just enough without forcing everyone into the same eight-hour box.
When Ryan took over AppQues, he and Jackson Falkowitz already aligned on fundamentals. Both valued agency, flexibility, and transparency. Both believed in trusting people to do good work outside an office.
But Ryan is different. He’s brash, direct, and talks fast. He works at a different pace than Jackson. Some people loved it. Others didn’t. He told them the truth: if this doesn’t work for you, leave. Don’t stay and get bitter.
He learned this from Mike Broshu, the hired-gun CEO who took over Ryan’s first company. On the day of acquisition, Mike said: “You’re either on the team or you’re not. That’s your choice.” It stuck with Ryan.
He also published decision-making guides in Notion so people know when they can move without approval. Two-way door decisions are theirs to make. One-way door decisions need conversation. Budget decisions inside department scope are theirs. Budget outside scope needs leadership buy-in.
Most decisions are reversible. Sleep on it. Let it breathe overnight. Come back with a clear head. The ones that matter—buying a company, rewriting the codebase, firing a customer—those deserve more thought.
If you're not self-aware, if you're not trying to improve yourself, if you're not taking control of your own career, your own job, your own skills, particularly now, I don't know what to do. Here's somebody who probably 3 years ago was like waking up to a bunch of tickets that she had to deflect. And that was her only, you know, that was her job. All that's happened at AppQus is most of our support people are doing really advanced technical engagements for our customers instead of fixing login issues. Like an app defront tip. They're happier. There's a woman Sophia on our team and she just like took it upon herself a month ago to detect when documents were out of date relative to customer asks, and she built a little agent to fix it for her.
Why you know, if it doesn't sound like you replace any roles with AI, like that already exists, but instead of going and creating a new role, you're looking AI first.
She has agency, she saw a problem, she went and fixed it. It was like so awesome to see.
So it's really interesting how from support, we're really getting these AI leads and they're really embracing AI as like they see so much process that can be automated to create a better experience for customers. Everyone, I am Luddy Sent and this is Who We Hire. We're joined today by Ryan Berry, uh father of three, a husband, and the CEO of AppQus. Ryan, thank you so much for being here. Really excited to have you on.
Thanks Luddy Sent. I am
Wonderful fellow. Ryan, you have spent the last decade building a culture and building a business from the ground up. Now, as the CEO of AppQus, you've inherited a culture. What are the first thing that you're thinking about in terms of team structure, uh AI, and and hiring when you go and inherit a team?
Yeah, I mean so it's it's crazy too. Like you you mentioned AI in there. Like when I joined AppQus last March to today, uh we're recording this this podcast in April. Um the game's changed in a year, completely. Everything's changed. Everything's exponential and like it makes it makes Moore's law law feel like a joke, you know, like there's exponential and then there's what's happening right now. So, I would say like it that's been an interesting thing. So, I guess I'll start there. Um when I was building Zappify from a much smaller size than we are here at AppQ's through the end, I had the the great partnership of an executive assistant and a chief of staff. And one of the first things I did when I joined AppQ's was say, "I'm actually not going to do either of those things." Not cuz I don't value the partnership of those two roles, but I was like it's a way to force me to figure out the cutting edge of what productivity tooling actually is as AI continues to explode. So, that was interesting. And you know, my first several months I tested dozens of products. Um So, that was part of it. I think what's interesting is like you inherit a business that's been there. It has a culture. It has a customer base. It has people who are really talented and great. And so, there's that backdrop and there's also like, well, you're there for a reason, right? You're not there to come in and like drive uh stability. You're there to like increase value. You're there to grow the company, to transform it. Whatever reason you're brought in. Um and you know, as a backdrop before I joined AppQ's, I helped bring in So, basically the way that Zappify ran was Steve Phillips was our founder and CEO, one of my very close friends. Um and I was the president. So, we kind of like co-ran the company the whole time. And when it was when like when a new CEO was coming in to Zappify, we were recruiting and his name's Aaron. He's a wonderful guy. We were recruiting Aaron and then obviously handing over keys. And I was there for 6 months like sort of helping. So, that was a really cool uh front-row seat to like what would then be my experience last March, right? To watch like, okay, how did he go about doing that? And
Wow.
Yeah, so it was it was a really like I I was uh grateful for that experience and and also for his partnership as like he took over my day-to-day, you know? Like I love Zappify and
from the
You got to transition it and then you got to be transitioned, too. and then yeah have
pretty much in in succession, you know? I think cuz I I had the chance to work with Aaron for about 6 months and then got recruited to join AppQ's. So, you know, maybe a month or two later I was here. And yeah, so it was like from one from one vantage point to the other um which I thought was really cool. Um and then, you know, coming into to AppQ's was was um you know, you want to balance like what about the existing strengths work? Like and really understand and respect the people that are there and like every decision was made with good intentions and so like trying to really understand the context of like how you get to this place. Um and then like meeting with like a lot of customers, meeting with a lot of prospects, trying to get a holistic view of the market. And I would say like I kept the space for both of those things to be done independently. So, like in one closet it was like what's my actual take on the market? So, I you know, I took a job in a completely different space than I've ever worked in. Um so, I had to form my own opinions of what I thought the problem was. Now, I had the benefit of being a customer of my uh of this category. So, I had some opinions. And then separately like first principles like let me let me re-evaluate everything and sort of keep those two things separate until they're not separate until you've done enough discovery to be like here's where I was right, here's where I was wrong, here's what I've learned and then you know, the plan is
So, you didn't come in to the team like hey, I already know what I'm doing. You came in with a observation mentality first.
100%. I I um I mean, you have to keep in mind too like I I over nearly 11 years at Zappy, I went through a lot of I made a lot of mistakes. I went through a lot of like scale-up things. I brought in VPs from big companies and so, I got to watch a lot of people come in hot. And I think there's a difference between coming in hot with passion in any new role and coming in like well, because this worked at company X, it's going to work here. Cuz you know, every company's slightly different and so, I think now in this moment of AI, what I just said is even more important because like there's pattern recognition, like, oh, I've seen this, okay? And then there's first principles. And when everything about the way in which we work is changing, and it really is. Like, everything's getting turned on its head. Now, everybody's in their own AI adoption curve, but it is actually changing. And so, you have to kind of keep reminding yourself like, what's actually real? And I found from my experience, too many people would come in and assume they knew the answer in week two. Um and for me it was like, who is actually our customer? What actually keeps them up at night? What are the structures that we have in place that work? What are the structures that we have in place that don't work? What do we actually need from a talent perspective? Um and so, those are questions I come in with a lot of curiosity about to then form a strategy to then go and execute.
Um
And I was going to thank you for your to your talk in Austin, uh and and you talk about, you know, hey, how AI's becoming stressful. I was like, you know, when I'm done with this talk, three new releases are going to happen and Um
That talk was in in November. Like, that was before Claude Code really popped. You see how that is? Like, in only a few months, you know?
Uh yeah, that's not That thing got published like a month or two after, which, you know, it's all old news by then, right? It's uh w- w- Which is fascinating. And you talk about uh you said you made an AI agent, right? So, like, you came in, which I thought was very fascinating. Uh you didn't want a personal assistant. You didn't want a chief of staff. You're like, what can I do with AI, you know, so it doesn't sound like you replace any roles with AI, but it like that already exists, but instead of going and creating a new role, you're looking AI first.
Yeah, I'm not looking to replace roles with AI, just to be super clear. Um like any CEO, you got to balance expenses and outcomes. It's part of the job, right? Like, it's just part of that. Unfortunately, you're responsible for P&L of the company you lead. Not unfortunately, it's just part of the job right?
The uh I've seen uh with myself, I've never been more productive than I am at this moment, but also a lot of my colleagues um just their availability to spend more time thinking. Like I actually posted about this on LinkedIn today. Like yesterday I was in a meeting with my head of sales and she was taking me through our like our entire customer base and she had segmented it. And um I said to her I was like, "You know what would be great to get like the nitty-gritty product usage data in here." Now, if you go back in time even a year ago in most companies and candidly in most companies still today.
Yeah, I've never had that in a sales rep. I've It would have been my dream so so many companies.
Exactly. And then like an hour later I'm in another meeting and I was like I I thought she was going to give the same update that I had already heard. So I was like I was like checking my Slack for something. I'll come back. And then I saw she had fundamentally changed the analysis, already had the data and it was in a robust discussion with our head of product. And I just thought to her
I saw
Holy Like we just broke down six silos and two hours later having the conversation that a year ago would have happened three weeks later. Um and so so I'm I'm looking at like how do you um how do you get all your data accessible to all your employees? How do you get the company's key strategic information, its cultural artifacts embedded into AI so that everybody has the right contact so that they can make the right decisions? Um And then how do you like amplify people, right? So like agents can elevate people cuz they can do mundane tasks for them. Um Like as an example, support automation was one of the first big uh big I think industries before engineering it was really support and um all that's happened at App Annie's most of our support people are doing really advanced technical engagements for our customers instead of fixing login issues. Like in that the front tip.
And they're happier. Fulfilling work.
I mean it's This woman is Sophia. Um shout out to Sophia. I don't know if she'll ever listen to this, but there's a woman Sophia on our team and she just like took it upon herself a month ago to detect when documents were out of date relative to customer asks, and she built a little agent to fix it for her.
What?
Yeah, and
They love it.
Right, and here's here's somebody who probably 3 years ago was like waking up to a bunch of tickets that she had to deflect. And that was like her only, you know, that was her job. And not to say Sophia doesn't have tickets to deflect any longer, but like that's that's her she presented to our entire company 2 weeks ago. I was like mind-blown. Brilliant. She has agency, she saw a problem, she went and fixed it. And it was like so awesome to see. I was like so I was I was like so inspired by that.
That we're we're going to have to send her to this podcast. So she's going to have to listen to this huge shout out. And uh
Sophia's humble. She wouldn't like that.
So our one one of our customers, Travis Marye, founder of Flex Point, we helped him hire a support rep and then he was on the pod telling us he turned into our AI czar. So it's really interesting now from support we're really getting these these AI uh leads and they're really embracing AI as like, you know, cuz they see so much process that can be automated and and they can create a better experience for customers. So it's really really fun to to hear that that's happened for you as well.
Yeah, bro. Totally. Yeah.
So yeah.
No, please.
No, I was just going to say the surface area in which we work is definitely changing and I think like th- this has been happening since supply chain automation, right? Like Um but then
I knew that was going to be your answer where you wanted to amplify people because I you know, I've been following your journey where you've recruited an executive team, right? A a head of marketing, a a CMO of uh VP of product. And I think the way you go about recruiting as well is you know, you talk about the tenure that a classic VP of marketing might have and it's 24 months and you know, you shout out to the the current one who had been there 6 plus years and you you what you're looking ahead in the future and how you want to build and partner. Um do you think like your personal brand and posting on LinkedIn and being active is that one of your recruiting superpowers or you do you work with um Whispered uh which is a executive recruiting platform or an agency? Like how do you look at recruiting these executives?
Um well, I mean, I I'm very grateful for the group of people who joined me. Um and I'm equally grateful to not be recruiting executives right now. I love the team I get to work with. Um I similarly to the chief of staffing and I've had some great experiences. I mean, just for full disclosure, I got placed at AppQues by TrueSearch, an executive search firm. So, like I and I have used True and other firms like this. I've used a lot of executive recruiters, recruitment companies, um outsourced like so I had a lot of exposure to these, you know, I've been hiring and building teams for a while, but um Kaylin Schaponick is our head of people here at AppQues. Um She's an amazing partner to me on so many things, not just not just recruiting related issues. Uh strategy issues. She's personally leading our AI expertise automation as an example. Like that's her project that she's running. Um but anyways, we uh we didn't use any outside recruitment help and we crowdsourced and open-sourced all the recruitment for um our VP of products, our VP of finance, our VP of marketing, our our VP of sales and CX. So, those are all new roles that we've brought into the company. Um and I mean, I I I have to be honest. I think some of what happened was it's a unique job market and I think there's something cool about a really interesting category where you get to rebirth a company and uh work for work for like an outside sort of like new CEO agenda. I think that's like attractive for executives who maybe been in founder-led businesses or in bigger businesses where maybe it's all about the reporting. So, there's like maybe something refreshing about like ooh, the cap table's clean, this this company has a good vision and there's patience and I can go and, you know, um but I also like I'm not for everybody, right? So, it is important to real real about like the type of person I am to work for. I mean, I have high expectations, I work fast, I talk fast, um you know, so like I I'm not like the easiest guy to work for, but equally like there's, you know, there's certain people that really enjoy that pace. Um and then it was really cool cuz like we were doing so much recruitment, so it was like not just about So, we'll just use Kristen who's our VP of Marketing who's amazing, but like how is Kristen's energy going to complement Bernie, our head of product side cuz we're building a team, not just hiring in an isolated silo. And so, I I actually spent a lot of time thinking about like how the different personalities would converge to get to the right outcomes and um you know, I'm having fun with the group. This is a great group of people.
I love it. I love that. You You do talk fast. I when I was prepping for this, I was watching some of your other podcasts and usually I listen on 1.5 speed. I was like, "Ah, I got to got to knock you down to 1.2." Couldn't I couldn't do it at 1.5. I was like Who?
Great.
What? What? To listen.
Yeah, a little bit, man. And the more excited I get, probably the faster I talk, you know.
Yeah, I wish I could put you on 1.25 and then the host on 1.5, so it then it then it could listen to us perfectly. Um
I wonder what the average cuz I do an internal video every Well, I've been doing this uh for almost 10 years, but once a week I record a video and I send it to the employees. And I haven't missed a week ever. Um it's just like a brain key. Uh Anyways, I wonder what the average uh speed people replay me on this.
That is Yeah, that'll be a good metric to to look at.
I think it's a loom, but I would like to know I'm curious I didn't figure
Um You You talk about when you're hiring people that you look for curious, adaptable, smart. Are those like written down or just those in your head? How, you know, you you you partnered with your your head of people. Um what are some of the core values that you're hiring on that are non-negotiable for you uh what when you're looking for these folks?
Oh, you you just said them. I mean, kudos to you for doing homework. Um I I did this project years ago. Like I tried to invert of all the roles, you know, so I've I've been responsible for finance teams, engineering teams, sales teams, marketing teams. And those come with different personality types, right? So, I was trying to like invert like what are the constants across introverts, extroverts, people of all walks of life. Like and it was are they curious? Like did they just naturally ask themselves questions? Are they adaptable cuz like I'm going to follow the customers in the market cuz I believe like if you do that, your business will always be able to survive hard times and and changes in the world. But that means that like change is a constant, right? So, you have to be adaptable to change. Um I think smart is sort of like a non-negotiable. It's smart Everybody's good at something, right? So, smart relative to the job like do you have the other technical skills to the job? Do you have the ability to like figure that out? And then growth minded was the only one you missed and I I can't emphasize that one enough because like if you're not self-aware, if you're not trying to improve yourself, if you're not taking control of your own career, your own job, your own skills, particularly now, I don't know what to do. Like I can't help you. Like I said this internally many weeks ago like you know, there's this whole notion of sales enablement and tell me exactly what to say in my PowerPoint and I'm like it's the game's over. You got to go in and try to stuff and figure it out and make it relevant for your customer. And so like somebody who's growth minded like gets that. They're like, "Okay, I'll pick up the things from the company. I know my customer. I'm going to go figure out what to do." And so you know, honestly across all walks of life, I've I've had that the pleasure to work with some badass people in my life and they they possess those traits every single time. Like every single time. Uh so I I don't and I won't hire if I have a red flag against any of those. Um you know, now obviously I don't hire everybody that walks through App Queues, right? So like um you know, like we're small enough where like I do usually meet with most people who we bring in before they come in, but not everybody, you know.
Yeah, and you mentioned you you inherited a great team from Jackson, all right? He built a great culture. Now you're coming into this culture rather than you know, building it from from the ground up. Uh and then like how do you go and impose some of the I I guess maybe you just really align with those those values to you know, and Jackson to begin with and you didn't even need to impose that on on the current team, but um like how how is that different than be building the the values from scratch verse hey, this is who we need to hire moving forward or you know, who doesn't have this on the current team? Is that is that something that you go and look at?
Um yeah, so I think I'll like I'll I'll start with like what was maybe and it's a good really good question, so I'll answer it as quickly as I can, but I'll I'll try to break it into a few parts. Um I think it started with like understanding where Jackson and I were aligned. So um there's a um uh What was the word? Um there's a generational alignment between us. We're both older millennials. So that comes with some natural, at least on a stereotype level, shorthand understanding. We believe teams should have agency. We believe that people don't need to be like chained to their desk to do good work. That people should have flexibility. Um we believe in transparency. So like there was a lot of like alignment on like a human level between him and I just as guys. Like we I Jackson is somebody who I talk to all the time still. Like so he's our board, right? Like so I know Jackson. I text with him all the time. Like, but he also was here for my first 2 months roughly. Um so it was like a nice slow handover, but there was some of that that kind of um alignment. Um I'm also like very clear on like some things that I won't deviate from. I start with the customer and work backwards. That's like just how I am. Like
I love it. Yeah, you had to pick up the phone.
Yeah, it's like if it's how I work. Like I and I and I like that's how I build strategy. Like if I if I I I sit with customers and I ask them a whole bunch of questions and I then pattern match that and then the answer's always obvious to me. Um so like that was important to me is like bring that customer focus into the company. I'm not even saying we worked customer focus before, but I'm like really customer focused. That was maybe a change.
Yeah, you wrote you wrote a book.
I wrote a book about customers. It's right there, the orange book in the top corner over there. Um you know, and like and by the way, it's so funny like some of the stuff I talked about that book 3 years ago is so true with data connectivity. But um so customer thing was one. Um trust and truth are big for me. They were also overlap with Jackson. Like trust people, tell the truth, you know? Like I'll employee can ask me any question and I'm going to tell them the the answer. Like I don't have a lot of like I don't know. I just don't it's too hard to have a work face and a not face. Um but there's obvious changes, right? Like I am I could be brash. I'm very direct. I I as you said, I talk really fast. Jackson's pretty chill, right? So it's like a very different disposition that came in and you know, that that was a that was obviously like maybe jarring for some people and maybe exciting for some people. And so some people were like this isn't this isn't for me anymore. And that's okay, too, right? Like I think my advice to anybody listening to this is if there's a change in leadership or change in strategy or change in ownership, do yourself the service of like seeing if it works for you and then just decide if you're in or you're out because it's all you can do. I think the worst thing you can do is be there, but be jaded and bitter. Um you know, and like I was first company I ever worked for which is an amazing company called GMI. It was a founder uh founder led business that then they brought in outside management. They scaled the company. They sold it. And the CEO was like the hired gun CEO. His name's Mike Broshu. Awesome guy. And he said the day we got bought, "You're either on the team or you're not. That's your choice." And I just like it really stuck with me. I'm like, "Yeah, just play your dog." Like you know, and and um and I think like I have a pretty like open feedback loop so that like helped me understand like what were people expecting, what were they missing, what was clear, what wasn't so I could tighten that up and and and ways that I thought would make sense for me. Hopefully that answers your question.
Yeah, absolutely. You know, so you're you're no stranger to building international teams. You started the US entity at Zappi. Um a lot of originated England, right? Um coming to you from And then uh had workers in South Africa globally, but nobody in Latin America. Now, I did correct me if I'm wrong, but you you inherited a team of engineers in Brazil. Um I guess Boston's no stranger to Brazil. It's the the actually the uh area where we have the most Brazilians in the US. Uh I'm I'm originally from there so I like to know that fun fact. Um the second most is South Florida. So, was that like intentional because they're you know, New England companies like, "Okay, this we already have some of this Brazilian culture." Like how did that transpire and how you know, how is it leading a South American team uh maybe for the first time?
So, um so yeah, like I think geographically dispersed teams is not new to me. Um we all figured out how to do that during COVID, I think. Like how do you communicate? When do you get on a plane? When do you be zoom? Like that sort of stuff. Um but for for me it goes way back like uh so Steve as you said founded Zappi in London. That's still that company's uh headquarters. Boston kind of became the commercial hub of the business. But about 5 years in his app, he we pivoted to being an enterprise company and we we merged with a South African entity. And so, similar to what I'm about to explain to you about Brazil and AppQ's, a lot of our core engineers were in Cape Town. And so, and by the way, a lot of engineers were in London and a lot of the commercial people were in Boston. So, you have to kind of find ways to connect people. Um and I think that that like there's a lot we could talk about there and it's an important skill set. So um I was comfortable with cuz our our uh staff in Brazil, Uruguay, and Colombia. So, we have we have people spread out across Latin America, actually. Um our uh first of all, they're awesome dudes. Um they all just happen to be dudes at this exact moment because plenty of uh diversity across our business, but um they're awesome dudes. Um they work hard, they communicate really well, and I and I think like that works here at AppQ's really well because of Chris Brookins as our VP of Engineering. She's an outstanding engineering leader and he's actually the constant since the CEO change. So, I'm very very grateful that Chris um uh stayed with me. Um I I may relate. Chris, we actually I don't know if you ever do like Myers-Briggs and stuff. We have the exact same personalities.
What is it?
I'm pissing him off or he's pissing me off. We're always like, "We're doing a plea." Um
I don't know. Actually, let me look it up. I'll tell you the exact one. Every time I've taken it, I get ENTP, ENTP. Uh we're we're doing this thing with Human Intelligence AI. And I said at the end of this, I mostly agree that that's right.
Oh, what is it?
Assertive Commander is what 16 Personalities says about
Assertive Commander.
You know, I I don't know if you ever do the 16. I We did this exercise when I joined when the whole team was recruited of like we did Myers-Briggs, but we had everybody self-identify with like, "What are your What is your kryptonite? What are your strengths? How do you like to handle conflict? How do you engage and learn? Um what's your why for being here? And like what time of day and where do you do your best thinking?" And so, we should we did that up like a lot of teams do this when they're forming. We did that, we created a charter, and now that's all embedded in our AI. So like if I'm going to go and talk to Chris, it's going to be like I wouldn't talk to Chris that way because of these things he said. And I'm like, oh yeah, no Right, uh Uh but to go to back to your Brazil question, like that's but that was part of the that was a decision that Jackson and Chris made years ago. Um it was a good decision. We have great we have really great people there that are doing key thing for us, and they're working in cross uh in in the same code base teams with people in Boston, and they they really just make it work. I think Chris has a lot of really good rhythm in place. He does uh two different hackathons a year where the engineering teams get together and create projects and execute them. Um we get together in person as much as we can, but it's actually been a Zoom thing. So they they do Zoom, they do documentation really well. Um we're in the process of relaunching the product in a few months. I don't know when this will air, but in July we're relaunching the product, and like a lot of people came in from uh other parts of the country and world to be part of the kickoff meeting for that, whenever that was, a month or two ago. Um so yeah, so I I'm no stranger to it. I think it's like it is about having the right rhythms, it's about having the right communication structures, it's about having shared kind of cultural alignment. Not every culture is different from a country perspective, but like around the business values. And then to the question you asked, knowing when to get on a plane and break bread with people. When when to get when to like get out of whiteboard marker. Like literally before this I was on the phone with Ricky who runs our support team cuz we're all going to assemble in Boston in two weeks. So there's a couple of key things we just need to work on.
That's going to be fun. That's going to be So uh do you have
Yeah, you know cuz you made the point about Boston, um I my wife grew up in Framingham, Mass, which might have more people from Brazil than like parts of Brazil at this point in time. All right. You're right. I think there's like Brazilian markets all around here. Uh and it's cool cuz most of our team's from Belo Horizonte, and that's where a lot of the people who have like decided to live in the Metro West, which is where I live, are from. So, it's it's like now I have this like connection point, which is kind of cool.
Do you get the Brazil team to Boston, or do you guys go to Brazil?
I I haven't made it down there yet, cuz everybody's in like sort of different places, but it's been most of them coming here. Uh
Nice. We're we're going to have to get your trip. They they made it complicated for America. You got to get a visa now, which is never fun, but uh it's an adventure, for sure. Do
I will get my ass down there at some point.
So, I you know, you you alluded to another question that I had prepped where you talk about when people work best, right? Some people want to wake up at 10:00 a.m. and work till 3:00, and you know, some people are better at night. How you know, you you you how how do you manage that? How did you manage their their energy and you know, that that ability to say, "Hey, like we need you present for this, but maybe they're not at their best at that time?" And I I know you talk about like, "Hey, I removed one-on-one from my calendar, and I unblocked this." So, like I I want to hear more about how you manage and lead people to for them to be their best.
Yeah, I mean, it's it's tricky. I mean, I think what happened is we started at factories, and then we went into offices, and we all converge around 9:00 to 5:00 is when we work. I remember this guy, Jack Millership, who's a really good friend of mine. I worked with him forever, and he like just didn't come to the office before 11:00. Cuz he's cuz he was like he was a night guy, night owl. And it never bothered me that Jack was not really like on until 11:00, because Jack was an absolute rockstar, like just an incredibly talented man. And oh, by the way, he would work later. Not that I care how many hours of the day somebody works, but like it didn't matter. And and that was a lesson I learned from him many, many years ago, like how you figure out like when you got to get everybody to align around a time versus like when it's okay, and and now like with with my team now, like I'm now for the first time in my really in my career or at least in a really long time, I'm not waking up to 50,000 emails from London, which I used to for sake of this. And um so I've decided to take my mornings back. So I don't do calls before 10:00 a.m. unless it's a customer who needs me. Um and what do I do between then and 10:00 a.m.? I work on stuff. I think, I write, I I have like I I just it's their really productive unlock frame. To contrast that, Bernie, our head of product, does her best thinking before 11:00 a.m. So we have to decide like when to meet in the middle and then or when she's going to go, "Ah, I got to like buckle up." versus when we're going to meet her where she is. And then I think it's just like a constant um it's a constant ebb and flow in a communication. So like I was working on something last night that she asked me to help her with at night because I I also like usually when my kids go to bed, I get like a little bit of energy. And I know what Bernie's like often, she's her brain's done for the day. But I so I wasn't surprised to wake up at 6:00 a.m. and had a ton of comments in my Notion doc, which I didn't get back to until 10:30 cuz I look, I was doing my morning thing. And so I think like leaning into asynchronous rhythms of people is when the works uh divide and conquer. And then trying to find common ground when you're trying to converge and align on something is is really the the balance that you have to strike. It's hard, man. I think it takes a lot of intention and a lot of over communication because as much as we've all been conditioned to work 9:00 to 5:00, which we I mean, we all do, right? But like when's the best time for someone to have a really intense conversation might differ across a team. And so how do you balance that? You know, I think it's And like for someone who maybe is like, "Okay, let's just take somebody who doesn't like to be in a super intense discussion at 4:00 in the afternoon." One of the leadership hacks that I have is like then don't let that be a decision-making meeting. Get it all on the table and then I've gotten very comfortable with the phrase, "Let's let this breathe overnight." And then and the next morning got a night's sleep and and brain can sort of process it. So those are some of the things that I've done. Very very
to talk about being flexible, very hard to make it work.
But, like what? Like, what are some of those decisions that I we don't need to make this right now?
So, it's funny cuz I'm as we've talked about in this podcast, I I move fast, I talk fast. Most decisions you can you can you can let have a night's sleep. Like, you know, now if it's I don't know if you know that like Jeff Bezos framing of one-way door, two-way door decisions. I believe like anybody in a company should be able to make any one-way door decision. Like, cuz you can make it, you can be wrong, and you can iterate. So, like, there's way too much bureaucracy in companies in my opinion of people who making getting approvals for one-way door decisions.
So, in terms of the decisions, you also talk, you know, on another talk or podcast that you did, you talk about VPs just needing to take action or like get out of the way. Just don't don't be the one just going to approve something, right? So, how do you how did you empower your team to go and do that?
Well, I think empowerment is the thing, right? Like, I don't I try to break down bureaucracy wherever I see it. Bureaucracy exists. Like, I mean, that was the thing Steve and I always held constant. Like, we value autonomy. I really do. Like, I don't want to have multiple layers of management. I don't I don't want people who were just like pushing paper around.
Did you come in with a peace offer? Did you did dump the kitchen sink? Like, what? How?
No, because I don't I think like everybody's trying their best, man. So, I think the best way to solve that problem is to break it down on a case-by-case basis and coach to it. Like, um when there's decision-making paralysis, it's like how do you break it down at the person level, at the decision level, and then and then use that like you don't need to ask anybody for that as a way for that individual to burn to build the muscle and the confidence that they need. Now, there's also scaled things you can do. Like, I I mean, I have published verified in our main Notion, which is our kind of intranet, decision-making guides. Like, and it basically says if it's a two-way door decision, make it a one-way door. If it If it involves money and you need to get approval to spend money and it's in your department budget, just do it inside your department. If you need money that's not in your department budget, well then you got to ask your department heads to bring it to the exact team and we'll figure out how we can save money somewhere else to pay for it.
You have decision making guides for everybody. You So, you have decision making guides in the company.
Yeah, but we haven't published and verified and as part of the work I told you K1's doing, that's going to just be embedded in in people's quads. So, that way if they're you know, everybody's talking to their quads at work these days or their chat GPTs, I want that to go right out to an employee. So, as they're thinking about like, oh I got to go talk to Tommy and Jessica and Philip, yeah, you could talk to them to get advice, but you don't need to ask them. Like, measure your decision, make it and then iterate is what I want for most decisions cuz like I said, most decisions are reversible. You can be wrong and just iterate. Now, if it's a buy a company, uh completely rewrite our code base, um fire a customer, I don't know. Like, a a decision that like you can't come back from, I'd like us to be a little bit more measured and I think those Those are always like, what's the problem we're trying to solve? What's the current state? What are we like What are the implications? They're more measured decisions. I think even with two-way door decisions, I still want people to be thoughtful. It's not like guns blazing, like what am I trying to do? What are my assumptions? You know, and that's where like even with those sometimes a night sleep is good. Like, you know, for me one of my personal test of it needs we need to let it breathe is if I don't feel calm and clear at the end of a conversation or something's being left unsaid, I usually I'm like, let my subconscious like process this and then I'll wake up tomorrow with like the two bullet points I still want to talk about. Um So, it's I like that's like a know myself thing or or like as a facilitator or leader of a meeting, like knowing like is there is there convergence around a direction even though there's maybe a disagree and commit dynamic or is it like still like up in the air and there's no right answer and that's obvious to us. So like let's just like sleep on it and see what the right thing to do is.
Uh I I I love the team you've built. It it sounds very exciting and that you, you know, you're going to get everybody together in 2 weeks to do whiteboarding, but you removed most one-on-ones or or all one-on-ones. How Tell me more about that cuz uh you know, some people say you need to have one-on-one to to be successful and to you know, manage people.
Yeah, it's so like I don't get a lot of energy from sitting on back-to-back Zoom calls all day at all. I'd rather work on the thing that's most important to the company and the customers every single day and that changes. Like so for me every week I'm like, "What's my theme this week? What's my theme today?" What it was I'm constantly like in a fight with time. Here's the other thing, which is probably going to be polarizing for whoever's listening to this. I'm not my direct reports therapist. And I found for a long time in my career a lot of one-on-ones were someone bringing me a monkey to put it on my back or wanting to complain about something. And like that's not what I get paid to do and there's a difference between leading somebody and coaching somebody and like being the dumping bag. Uh and I'm like just that's, you know, that's just not me. I'm not going to like I I I'm not willing to do that. I I I think it's a bad use of company money for me to be the one doing that. Um you know, so those are like some of the backdrops. Um I do believe like I do this with my directs like once a quarter I like to spend a day with somebody. Like just doesn't mean in like
In person?
Yeah, like as as we're at as much as possible in person, but like let's zoom out. Like how we doing? How we like That gives me a much better opportunity. Now some people So I'm just trying to think of my direct team right now. I only have one-on-ones with two of seven people on the team. Now that is because those people value the help talking through priorities. So, we've contracted like it's not going to be a therapy thing. Like if you know, we very much contracted. So, I sort of like as a starting place I don't want to have one-on-ones. But, um you know, but that's like that's where that sort of landed. I also like I want to talk to people around the business. So, my first year at AccuQuest is really quite interesting cuz like I needed to be out in the market figuring out like customer problems, jobs to be done so I could like help lead the company. It was a new industry for me. I had to figure all that out. But, I get as much value from like when I get off the phone with you I'm meeting with one of our product managers. It is actually a one-on-one, but it's not a standard one-on-one. We're just going to like jump in to talk about business context because he's he's operating with different context than I am. And so, by us sharing with each other I'm going to get smarter, he's going to get smarter, we can both divide and conquer. So, I think about like every 3 months how do I canvas key people in the company that like are driving something critical at a different lens than maybe I am and like how can we do that? And so, like that's it that's a shape of a one-on-one that I like. But, I think the thing that I'm guarding against is like the weekly silo creation meeting where it's like I'm going to meet with engineering VP and then I'm going to meet with product VP. Then I'm going to meet with marketing VP. And actually all four of us need to talk. And so, why the hell didn't we just get in a room? You know, where does where I would say there's a big exception to my rhetoric around one-on-ones is in customer-facing roles. Like I think like week-to-week coaching around calls, around messaging. Like I do think that that's valuable. But, I I would say the contract needs to be more formal like what is it about like I'm just speaking go-to-market but like when is it about the metrics? When is it about skill development? And I think sales and CS leaders particularly need to have their together on that cuz there's too often it's like a conflation of therapy, what's up with this deal, and oh by the way, can you look into that? And I think like the space needs to be created like as an example, pipeline reviews should be a really formal thing. Discovery call coaching should be a thing if somebody needs that. Like, let's work on discovery call coaching.
Everybody needs that. So, I'm going to send this card for how to go to market. This is uh this is a great take, Ryan. Really valuable lesson for anybody organizing, you know, go to market teams calendar and time. I I I love that take. Thank you.
Yeah, no problem. Thank you.
The So, you know, as we wrap up here, I know you got to jump on a on a call and this is going to launch before your product release. So, mid-May, uh we'll promote this out. Uh and we'll be excited to see what, you know, the new product is is looking like based on, you know, all the work y'all have been doing the last year. Uh but somebody being a, you know, first-time founder or inheriting a team for the first time, like, what's one takeaway that you want them to have on on hiring and you know, through your your decades of experience, um leading and growing teams, you know, what what for for them doing it for the first time, what's one takeaway that you want to make sure that they they leave with?
If you're a founder, don't give away your cap table before you have product market fit. Uh Like, hear some Like, you know, a lot of founders who call me and I'm like, don't do it. You're not product market fit yet cuz once the investors are great, but once they're at dinner, they come every night. Um with respect to being uh to having teams, um make sure your um really clear about who you are and what your strengths and weaknesses are and be transparent about what you expect with people. Be transparent about the company throughout the interview process so that they can really get to know you and you can really get to know them and I would I would say be very intentional about the types of DNA that's going to complement you because you're listening and you're different than me. So, what you know, what every team cohesion is like really important to think about. So, I think if I was to say one word, be very intentional about the team that you create. The team is going to be the the the team is going to be the thing that the company relies on. Like I I don't care about all the AI. I'm a very AI forward guy. I use AI all the time, but people still build great companies. And teams are the are the reason for that happening. Um whether they're smaller teams or not is a different thing. Like obviously there's all these wonderful stories of three-person startups turning into a billion dollars or whatever, but there's still a team of people that work really well together. Um so that would be my advice.
I love it. It's uh I mean you're you're building teams with of executives and uh coaching little ones in in basketball. So your your life revolves around teams. Uh really what a pleasure learning from you today, Ryan Berry. Thank you so much for for coming on Who We Hire.
Thank you so much, Louis. This is really fun and thanks everybody for listening. Get at me at LinkedIn if anybody wants to connect.
Yeah, so on LinkedIn, Ryan Berry, and you have two newsletters that you promote there. Um can you tell us what
I'm only I'm only maintaining one. It's called the Experience Shift. So I talk a lot about the things that happen inside of companies that show up for bad customer experience. And then how you can create customer experiences that will make you money. The last one I did is Ryan's Rants. There's some very funny articles in there about corporate dysfunction. So keep in mind I spent a lot of time selling to very big, large, matrixed organizations, which are still our customers here by and large. Um and uh I I talked a lot about the dysfunction that got in the way of execution. So uh those artifacts are probably still useful, but I maintain the Experience Shift.
Amazing. So we'll link to that in the show notes and uh excited for your product release here soon.
Yeah, thank you, Louis. Thanks for everybody for listening.
All right.
