Juan Betancourt
C-suite
Juan Betancourt spent over a decade placing C-suite leaders at Fortune 100 companies through elite recruiting firms like Korn Ferry and Heidrick & Struggles. Then he founded Human Intelligence (Ask Oracle), an AI coach embedded in Slack and Teams that uses behavioral science to help leaders manage their teams in real time. The company has 12 employees and zero turnover in five years. His biggest discovery: everything he learned about hiring at the enterprise level was the opposite of what works in early-stage startups.
At Korn Ferry and Heidrick & Struggles, Betancourt hired CFOs and chief marketing officers who had already exited multiple companies, graduated from Harvard or Wharton, and could get any job they wanted. He charged clients $150,000 to $200,000 for four weeks of work. That filtering was built in. By the time he met a candidate, elite institutions and prior exits had already vetted them.
Starting Ask Oracle was different. He had no brand. He had no Fortune 500 credibility. He tried to apply that same playbook to early-stage hiring and failed repeatedly.
I had to switch the flip the switch and say, I need to run a company like the Bad News Bears and hire Bs and Cs. Speed to market mattered more than having perfect A+ players.
Juan Betancourt, Human Intelligence
The shift required him to get over his ego. At Procter & Gamble, at Harvard, at Reebok and Puma, he had always been surrounded by top performers. At a startup with limited resources, that luxury didn’t exist. He needed people who would execute and move fast, not people who would demand perfect conditions before taking the job.
Betancourt made the same mistake repeatedly with senior hires in marketing and sales. He talked to candidates with strong resumes who said they had done it before and would do it again. He believed them. They had succeeded at other companies. Why wouldn’t they succeed at Ask Oracle?
The problem was hunger. At big corporations, good salespeople and marketers had both base salary and commission. They were already winning. At a startup paying less with equity as the upside, they needed to be hungry. They needed to believe in themselves enough to take the risk. Betancourt’s hires didn’t have that.
What might be missing is they used to be able to do it because they had hunger. Now they don’t have the hunger. If someone doesn’t have the hunger, they won’t do the work. They’re just going to give you strategy.
Juan Betancourt, Human Intelligence
Most startup founders are the strategist. They don’t need another strategist. They need a doer who will execute the strategy. Betancourt learned this lesson the hard way, cycling through senior hires over eight years before he got it right.
At Korn Ferry, reference checks for Fortune 500 hires were theater. A CFO who had been at four private equity firms and exited six times would have glowing references. Of course they did. They were already proven. The references taught him nothing new.
At Ask Oracle, especially for remote roles, reference checks became the most predictive tool he had. He needed to talk to people who had actually worked alongside candidates, not just their bosses or peers at large companies. He needed to know: Does this person work because someone is watching them, or because they have internal motivation to grind?
Remote work exposed that fast. Someone might tell you they work well independently. Their actual former colleagues would tell you whether they did.
Reference checking became critical, much more important at a small startup than when I was an executive search consultant.
Juan Betancourt, Human Intelligence
At Korn Ferry and Heidrick, Betancourt noticed something odd: very few consultants hired for sales roles. There were consultants specializing in finance, supply chain, R&D, marketing. But sales was sparse. When he started hiring salespeople for Ask Oracle, he understood why.
Sales isn’t a skill you can screen in an interview like finance or engineering. You can ask a finance person about a balance sheet. You can ask an engineer about architecture. Sales is personality. It’s reading the room, knowing when to push and when to back off, following up without being annoying. You don’t know if a salesperson will work until they’re three months into the job.
So he stopped trying to predict and started hiring based on what had already happened. He now requires referrals. He only hires salespeople who are currently employed (good salespeople stay employed). He hires only for the specific vertical. HR tech salespeople, not generic software salespeople. He hires only for the deal size and stage he’s selling into. Enterprise account executives with enterprise experience, not SDRs hoping to learn.
Critical: don’t ever hire a sales person without referrals. A good sales person is always employed.
Juan Betancourt, Human Intelligence
He also restructures the comp package to test commitment. Lower base, higher commission, with equity that vests only if the hire makes it three months. If they don’t believe they’ll win, they won’t take the deal. If they take it, he knows they believe in themselves.
For the first few years of Ask Oracle, Betancourt led like he had at Procter & Gamble. He was a dictator. He set the rules: Arial, nine-point font, blue text, subject lines formatted this way. He created templates for emails, for one-on-ones, for reporting cycles. He micromanaged every decision because he knew his vision and didn’t want it diluted.
People were paralyzed. Nothing happened. The company was failing. And Betancourt was exhausted, working 7 a.m. to 8 p.m. every day with no time for his family. He realized he had become the bottleneck.
One day he flipped the switch to the other extreme. He gave his team complete freedom. He stopped criticizing ideas. He stopped rewriting emails. He let them make decisions he knew would fail, because he knew they would learn faster than he could teach them.
I knowingly let them make decisions I knew would fail. When I started the company everything that was a bad idea I’d be like no that wouldn’t work and here’s why. I was criticizing everything.
Juan Betancourt, Human Intelligence
The results surprised him. People worked harder. They took ownership. They became invested in outcomes, not just tasks. A B or C player with freedom, he learned, could outwork an A player in a cage. The culture became fun. The product improved. And in the last five years, the company has had zero turnover.
His leadership role flipped too. He went from 90% doing and 10% leading to 90% leading and 10% doing. He now spends his time setting vision, removing obstacles, and trusting his team to execute. He got his evenings back. He watches his kids’ soccer games.
Ask Oracle’s core product is an AI coach that uses psychometric assessments and behavioral science to help leaders manage teams in real time. But Betancourt also uses the same tool internally when hiring. Every new candidate takes a ten-minute personality assessment. His team sees the results. They know what friction will come, and they prepare for it.
Most startup CEOs hire people who think like them, act like them, work like them. It feels good in the interview. Everyone gets along. But homogeneous teams fail at scale. A company of all decisive action-takers will panic when the business needs deliberation. A company of all risk-averse people will never try anything new.
Betancourt now hires deliberately for diversity of thought. He tells his team: “This person is very different from how you think. You’re going to butt heads. It’s going to be uncomfortable. But if we figure out how to work together, we’ll make a better product.” The behavioral science data gives them a roadmap for how to work across differences, not just why they exist.
If you have 20 employees who all think the same, you won’t be agile, you won’t be able to solve as many problems, and your company will fail.
Juan Betancourt, Human Intelligence
Betancourt left the United States at 22 and returned at 42. He lived in Germany, Brazil, France, Spain, Italy, Abu Dhabi, and Dubai. He speaks five languages. He managed tens of thousands of employees across multiple cultures for companies like Procter & Gamble. Early in his tenure in France, he nearly got fired.
He was brought in as a hired executive by a CEO managing 600,000 employees. Betancourt’s leadership style was American: ask for input, build consensus, develop people, delegate authority. In his French stores, he was rated as the worst leader. Employees hated him. The CEO pulled him aside and explained: In France, you lead by proving you know more than everyone else. You criticize constantly. You make them question whether they should be in their job. Only then do they respect your authority.
It was brutal. But Betancourt had learned to be a chameleon. By moving to a new country every three years of his childhood and young career, he had developed the ability to shed his identity and adopt a new one. He flipped the switch, became the demanding French boss, and within three years turned a bottom-ten store into a top-five performer. Then he got promoted to run the United States and Brazil.
Leading in France is very different than leading in the US. In France, the more you are directive and tell people clearly what you want, the dumber you come across.
Juan Betancourt, Human Intelligence
In France, leadership is an art of suggestion. You can never give an order directly. Everything is framed as a question: “Would you be willing to do this tomorrow instead of Friday?” The underlying message is clear, but the form is a question. It’s like parenting a teenager without telling them what to do. And in France, you must treat a janitor with the same respect you’d give a doctor. The energetic vibration changes everything.
The US, by contrast, is about clarity and directiveness. Tell people what you want. Make the goal explicit. Let them figure out the path.
Betancourt found Germany closest to the American style. But France and the US were polar opposites. And he observed something else: the smartest population he’d ever met, the French, were also the most miserable. The system was so rigid, so bound by class and bureaucracy, that even brilliant people rarely fulfilled their potential. The entrepreneurs left for San Francisco. The word entrepreneur, which came from French, no longer even existed in France.
Ask Oracle could hire developers and sales people in Mexico, Brazil, France, and Costa Rica. Betancourt knows how to do it. But instead, he licenses his product to local distributor partners. He gives up 20% of potential revenue to avoid the headache of hiring, managing, and building culture across cultures at this stage of the company.
It’s a learned decision. He knows how hard it is to lead across cultures. He knows the compliance, the legal structures, the communication overhead. At 12 employees with zero turnover, he’s focused on product and market. He can afford to trade margin for simplicity.
For a founder at his scale making that trade, it makes sense. Hiring in Latin America is viable, but only if you’re ready to invest the time in doing it right. Betancourt chose not to.
Betancourt distilled his learnings into three rules for founders making their first hires:
For salespeople: Get two references. Structure the deal so equity doesn’t fully vest until three months. Use a behavioral assessment to understand your company culture and where you need to go. Then hire someone from your industry vertical who has done enterprise selling if you’re selling enterprise. Don’t teach someone how to sell your product and your market simultaneously.
For developers: Betancourt has worked with developers across Latin America. Colombia has delivered the best technical talent he’s worked with, followed by Costa Rica, then Argentina and Brazil. If you’re building in nearshore, start there.
For all hires: Use a behavioral assessment, like a personality test, to understand the culture of your company today and where you need it to go. Hire people who fill gaps, not people who mirror you. Understand the trade-offs you’re making and be explicit about them with your team.
I used to be a dictator leader, the first
and I put the fear of God in everybody in every meeting and people were paralyzed and the company was failing. I was exhausted. I was working literally 7:00 a.m. to 8:00 p.m. at night, no time for my family and I was like I this isn't scalable. And so I finally flipped the switch one day and said, you know what, try the other extreme. Give them complete freedom and see what happens. And no turnover in the last 5 years. So I can trust them. Let's talk about that. How? I knowingly let them make decisions that I know will fail. Now I do 90% leading and 10% doing. You have pressure as well, right? You have investors, you have a board, your pressure to increase ARR per employee is real. And how are you looking at that? Are you using AI to replace anybody? I mean I'm Luis Sanz and this is Who We Hire. Today I'm with Juan Betancourt, founder of Human Intelligence known as Ask Oracle. Juan's spent over a decade placing C-suite leaders at Fortune 100 companies before betting that framework on his own company, Ask Oracle, an AI coach inside Slack and Teams. Currently at Accenture, Coca-Cola, Microsoft and we're going to be getting into his executive search background and what he got wrong about early stage hiring. The hardest hire he's ever made and what kind of team it takes to support an AI product at enterprise scale. Juan, welcome to Who We Hire. Thanks for having me, Luis. Pleasure is all mine. Let's dive in. So, you know, what does hiring look like at Ask Oracle today versus when you just started? Much more informed, right? I've been doing the startup thing for 10 years. Um when I left executive search to start my company uh I thought I would just apply all the great learnings that I did hiring C-suite executives, so chief marketing officers, chief executive officers, chief financial officers, so all the C-suite. And then obviously some SVPs and VPs for private equity portfolio companies. That was my niche. I was very, very good at it. And I just thought, oh, I'll just apply what I learned there to hiring for my startup. Um and it was quite different. I don't know if you want me to if you have specific questions or if you want me to free will at some of my learnings, but Yeah, yeah, do do share why, you know, what surprised you that was different about it. Were there anything that you could take away or did you have to completely rewrite the the playbook? Pretty much completely rewrite the playbook. So here's a few thoughts. You know, I was hiring the most elite executives in the world who either went to the best schools and then kind of exited five companies they ran, you know, at a multiples of 5x for private equity, right? Um who could get any job they wanted, but I was working for the best private equity firms with the best jobs. Trying to hire for a company that has no brand recognition, um you don't get all these A+ superstars applying and trying to get them to join, doesn't matter how well you articulate our opportunity, those kind of people are more risk averse and sniff out risk and challenge. And they kind of self-select into really good situations. So it was just harder to attract A+ superstars. So I had to go from the mentality of and by the way, I used to work at like Reebok and Puma and Procter & Gamble, you know, some great companies and having gone to Harvard and Wharton, I'd always been working around A+. I had to switch the flip the switch and say, I need to run a company like the Bad News Bears and hire Bs and Cs. And it's really about speed to market and getting my product out there than having the perfect team of all A+ players. So that was the first switch I had to change, which is settling for different quality, but still trying to achieve my vision. That was very difficult for my ego to swallow. And yeah, I can imagine. Were these Who was your first hire? Was it the engineering team? Was it uh sales? Like who did you hire first? It was the the developers, uh the software engineers. Um so it was more mid-level roles to start building the product versus executives. Cuz that was a whole 'nother thing of hiring a mid-level person or engineer versus someone who's going to be your partner and co-founder in the company. That's a whole 'nother experience. Um uh there was another challenge where I made the mistake, I would talk to people in sales and marketing when I was looking now for the executive, the person to do all sales, to do all marketing, um as part of the leadership team. I fell for the oh, I've done it before, I'm great, trust me. And their resumes were padded and did well and they had succeeded. The problem was they were no longer hungry. And so when I used to work in executive search, I mean, these people are getting paid so much money, they were still hungry. Um here we're not paying that much, so you really need someone who's hungry, who's going to do it on the equity component. Yeah. And I I struck out and hired probably three marketing people over 8 years and three or four sales people over 8 years and even a couple advisors, which is also like hiring to get advisors, who all sold me on how much wisdom they had and how they could come in and do it and just trust them. And so another lesson I would take away from those experiences, don't trust someone just because they've had success and they say I can do it for you, too, because what might be missing is they used to be able to do it because they had hunger. Now they don't have the hunger and doesn't matter how smart or how experienced they are. If someone doesn't have the hunger, they actually won't go and do the work and they're just going to give you strategy. And most startup CEOs and the founders, they're the strategy, they're the visionaries. They don't need someone coming in giving them strategy and vision. What do you need to do? They need doers, executive level doers. And that was something that I missed early on. Another uh thing is size of company, the phase, right? Hiring for a startup is different than hiring for 0 to 1 million or 0 to 2 million. Under 20 employees is very different than hiring for the 2 to 10 million phase, 10 to 100 million phase, 100 to a billion phase or greater than billion. You can take someone from let's say that second, third, fourth phase and move them up and down the chain or up the chain. The startup 0 to 1 million, you have very little budget. You need someone who's the ultimate doer who who enjoys doing more than leading. And you're not hiring leaders. A lot of executive search people I was hiring, they were strategy and leaders. I mean, 80% of what they were being hired for was their strategic vision and their leadership. When you're hiring a carry the back salesperson to do everything, it's not a chief revenue officer, it's a sales accounting exec, right? You're hiring a marketing person, it's not a chief marketing officer at a startup, it's a lead gen person who knows how to get fill the funnel, get leads and and have you rocking and and then hiring maybe one, you know, BDR, SDR. So it was very different in terms of what they brought and so that was very different. I had to learn that. Also, I my company's fully remote. This might not apply to all startups, but I think a lot of startups today are remote. I never hired for remote executives. I just took people for their word that they'd be fine working remote. Well, I I got bit in the you know where because some of these execs, they have all the best intention ever, but they were not cut out to work remotely. They just aren't as
What happened? Like what what they they were not working or they weren't productive or Someone who is self-motivated to work 50 hours a week without someone down their back or watching them is a very different profile than someone who works because they're being watched. And that's very hard to identify in an interview. Um one of the ways I've learned to get around that blind spot is whereas at big companies references never really led to like insight. You're a you're a CFO at a big company, all the references, bosses, peers, they're always glowing, right? There might be little things like, oh, well, they work so hard, they were too hard on the team. Like like, you know, yeah, like okay, that's a negative, but come on. Once I put in doing reference checks for any executive hire or even mid-level hires, talking to people who've worked with these people who've already worked with them in a real capacity, you will find out very quickly if they crush it and are never-ending workers just because they love work and they they have a passion for work and they're self-motivated versus those that don't. So reference checking became critical, much more important at a small startup than when I was an executive search consultant hiring. All my clients that paid me to do references at the big companies, but I never got the same insight such important insight, especially for remote work, for instance. Um Interesting. And you think that's bureaucracy based? Like they like can't go and say anything bad or what what why do you think that is? I think when you're hiring C-suite execs at larger companies, it's kind of like they're already great. Yeah.
So your your population of people is just you're interviewing and meeting great execs. So they they probably came from a reference, right? It's They've already been referenced four different companies. They it's, you know, it's like you you hire somebody from a community college or you hire someone from Harvard. Well, Harvard University's already done the filtering, so without even knowing the two people, you're probably going to get a better quality from the Harvard grad than the community college. I'm not saying that's always true. There might be somebody at the community college who never had the opportunity. But, you don't want to go through 100 people to find that gem. Yeah, that's that filter for you. It It filters for you. They got into Harvard, they got in, they wrote the essay. Right? Like Like they're already top student of their class of the high school. You know, I was hiring CFOs who've already been at four private equity firms who've already exited six times. Yeah. I mean, by the time I talked to them, like I already knew that like they're pretty darn good. A reference check isn't going to uncover something that in 20 years their experience didn't uncover. I love it. So, you know, a lot of learnings there for sure. But now you you built a product that uses behavioral science to coach people at work. Uh I've used it. I You know, we've had some stressful situations. Hey, how do we deal with uh with this person leaving? How do we talk to the team about this? How do we motivate uh them to do more, right? And the it it you know, really valuable product for our team, but how does it that change like how you evaluate candidates? Do you now introduce that into the interview process? Um or where, you know, where do you recommend companies uh that want to test something like like this out it it introduce it? Is it on onboarding after? Is it during an interview process? How do you How do you look at that and how do you use it inside your company? Yeah, I found the large companies when I was an executive search consultant culture fit wasn't as important, right? One person in a 12,000 person company isn't going to impact the culture of the company. Like they're diluted, if you will. Um and if you want the best CFO in the world to do, you know, balance sheet re-maneuvering, I hate to say this, but you're going to want the best CFO who knows how to do that, whether they're perfectly aligned to your culture or not. Right? That you're going to looking for is a But in a small company of five, 10, 20 people, one person does impact the culture, especially if they're managing five of the 10 employees as an executive. So, more so than before, our behavioral science, the Human Intelligence tool, or any behavioral science tool that you can use, what they call psychometric instruments, are really important to understand what you're hiring. Most CEOs of startups interview people and get jazzed by finding people who think like them, act like them, and work like them. What they don't realize is they're creating an imbalance where everyone on the team thinks the same. And if you don't have diversity of thought in your 12 employees, and everyone's decisive, well, when there's a moment in the business model that you need to be deliberate and not just go fast, you're going to fail. So, to be a great startup, you need to be agile. Only hiring people that the that the employees all liked in the interview process, like you would you know, go through the 100 applicants, you interview 20, and you get to the final five to full days, and at the end of the full days, all 10 employees vote, "Oh, we all like Johnny." Well, if you actually start looking at it, the reason you all like Johnny, even though all five could do the job, is because Johnny didn't challenge anybody in the interview. There was no friction. It was easy, and you want to go have drinks with them. Well, guess what? After two years at a company, if you have 20 employees who all think the same, you won't be agile, you won't be able to solve as many problems, and your company will fail. And the culture that got you to $1 million will be the culture that fails you going to 10. And so, you need scientific, data-driven measurement of where you're coming from culturally, what any one exact or any employee adds to that culture, culture add, complement, and what the culture you're in need for the next phase of your company. Because if you don't change and can't manage that culture shift with data, you will fail. And that's actually why most startups fail, not because they can't keep their culture, it's because they actually keep the exact same culture going from phase zero to one to one to 10. Wow. So, are you before you're introducing somebody new in the company, do you have them go through uh ask
We have everyone take the assessment. We show them how they're different or similar. Uh who in the interview process is going to butt heads with them, and that's okay. We let our own internal employees know, "Look, we're going to hire this person. They're very different than the way you think. They're very structured in process. You were really creative, and you guys are going to work together. It's going to be a pain in everybody's butt. But if we can figure out how to work together, it's going to be a better product, a better solution." And so, that's But you have to leverage the data in advance, not just have it and then not share it. And are there people skeptical taking it in the interview process? Hey, I I don't want to do this. It's This is too much. Because it's only 10 minutes, we rarely have someone say no. I mean, if somebody wants to work at a company, if taking a 10-minute personality test is too much, Yeah. good luck them working hard on the weekend.
Based on the poll. Yeah, you we we send, you know, hour-long assessments and tests and it you know, so, you're right, with 10 minutes it it shouldn't be a a huge blocker and uh you know, I think everybody that I've seen that ever has taken it has had fun uh with it, especially
it's also fun. And we don't tell you you're good or you're bad. There's nothing that can't be weaponized against you. We don't use high low, we use horizontal scales versus up and down. So, it it and it's value. It's value to you, right? At the end of the day, you can go and take it, and even if you don't get the job in that next interview, you come, you know, better equipped and and self-aware. So, It's a warning. You could It actually It's a gift that the company that declines you is giving you to take to your next role. Or I just love it. I love it. I love it. So, uh you know, you talked about marketing hires, you talked about sales hires, but like what's the hardest hire you've made at Human Intelligence? For sure, sales. Sales.
That's where I have failed the most. It's funny, when I was an executive search consultant at the two largest firms in the world, these are like the McKinsey, the Goldman Sachs, the the GEs, then. Right? Korn Ferry and Heidrick Korn Ferry means Yeah. And Heidrick Yeah, you get paid $150 to $200,000 for four weeks of work, right? It's You know, the average partner makes two to three million dollars a year, right? It is the It's the elite of the elite of hiring, right? And so, I was in that world, and like I always wondered, we hire for every industry, every vertical, chemicals mining oil gas consumer retail, right? So, there's all these practices. It's kind of like a consult professional services model. And we hired for almost every function. Marketing, finance, supply chain, right? R&D. But the one that there was not many consultants hiring for, very few if ever, were sales people. And I always thought that strange, like there's so many sales roles. Why wouldn't we be doing these? When I started hiring for sales in my startup 10 years ago, I realized why.
And those people are the only role that it's it's less of a science and more of a personality. So, you you can't ask interview questions that are that are, you know, a finance person you can ask them financial questions and understand like their ability to do finance, right? Like a skill set. Sales it is a skill set, don't get me wrong, but it's it's more of a skill set of personality, understanding, and reading between the tea leaves, and knowing when to put pressure and not, and follow up. Like it's just so hard to interview for, and most sales roles, you don't know who you're getting, if they're going to succeed or not, until they've been in the job for three months. Um you know, so, what I learned eventually was referrals. Critical. Don't ever hire a sales person without referrals. Um I also never will hire a sales person who's unemployed now. A good sales person is always employed. Um I also realized that if a sales person's not willing to pay to in a startup environment, not willing to take the um commission a strong commission structure and lower base, that means they don't believe themselves. Great sales people, they'd rather make a lot more money on commission, if it's like twice as much, than a guarantee, because they know they'll succeed. Someone who's not sure about themselves isn't going to play that game in the startup model. At the big corporations, good sales people, they get both. They get a huge base and a huge commission. Um uh what else about sales people? Um Sales is a role where if you were at least in software, like we do HR tech. I made the mistake to believe sales people tell me that they could their skills as a sales person were transferable into HR tech. Boy, was I wrong. I I only hire now HR tech sales people to sell HR tech. Wow. And you're focused on the enterprise, so enterprise and HR tech. And people who've done enterprise. If they haven't done enterprise, I'm not going to waste my time. Now, this is for like account execs. Like obviously SDRs and lower-level sales people, I'm open to to being more open to that. Yeah, you can train them. The And then, you know, so I definitely a lot of learnings there. Um you know, especially looking at it from the startup mindset versus an executive type search mindset and attracting uh you know, so being able to go go like where where do you go and find and and and attract that talent? Like you mentioned referrals, but what, you know, what what what what else? I mean, I because I was a search consultant, I mean, I I would search on LinkedIn. So, basically, I still do the search on LinkedIn when I try to find executives. Um whereas when I was when I was working for KKR, you know, Platinum Equity Partners, you know, all these big PE firms, everyone would respond. When I say everyone, let's say eight of 10 execs would respond.
Wow. the top execs in the country. For my startup with no brand recognition, I would get maybe one in 20 responses. So, one in 20. And is it for executive roles or also like account executives? Executives. Like Like the Like my head of marketing, my head of sales, like um uh just people are risk averse, and if they don't know your brand or your company, you know, But your brand's already possible like you have great customers. I mean obviously 10 years ago it was more difficult than than it is now and I imagine you're it's not one in 20 anymore, right? Yeah, but there's 17,000 HR tech companies out there that are all now now with AI just like VCs holding their money back and not investing in in SAS because they don't know what AI is going to do. I think a lot of people don't want to jump to a new startup until there's a lot more traction, until it's a lot safer. There's everybody's on a hold right now on this planet comes to technology roles like like it's Yeah, it's it's tough to to get people to respond um for roles. Well, you you have pressure as well, right? You have investors, you have a board, so they you know, you're pressured to increase ARR per employee is real and it's And so how how are you looking at that? Are you using AI to replace anybody? I mean we're using AI to to to develop our platform twice as fast. So what we've done in the last six months would have taken us two years. So developers are using AI.
Developers using AI um uh in terms of And how are they using AI?
marketing we're using AI on our marketing a lot in our marketing. Our sales team is now right now they're in the middle of implementing a whole new connection with AI to go through everything through and connect it with HubSpot. So we'll probably be you leveraging AI in the next two months in in sales as well.
Wow. So you got dev, marketing and sales all using AI, but it sounds like they're using it to supplement not really replace themselves in their roles. To supplement yeah. If we didn't have AI we probably would have to hire to do those things. Okay, so you're you know, you're not laying anybody off, but you're not opening that new roles because AI has made everybody more efficient.
Correct. We were always more lean than we wanted to be, so there was no fat to trim. Love it. Love it. Love it. Love it. Now you you mentioned the developers using it um any example like are are they using quad code or are they using cursor? Like what what does that look like behind the scenes?
tech CEO who's not technical, so they just give me updates on what's being done on the road map and how fast and I've just noticed that it's twice as fast. Why? I said how are they doing that because we're not hiring new people. They're like oh AI is doing it for us. That's that's incredible. So you just you you enabled them, bought the software and said go and uh Yes, I'm the CEO who I'm in a lucky place where I I have 12 people um in my company and no turnover in the last five years. So I can trust them.
Wait, what? Yes. No turnover in the let's let's talk about that. How? So I I used to be a dictator leader the first couple years. And and I put the fear of God in everybody in every meeting and people were paralyzed and the company was failing. And I realized that I couldn't lead and manage like I did at Procter & Gamble with all Harvard and Wharton and MIT and Stanford grads who were in business. I realized that I was scaring everybody and making them feel like crap. And so I realized that giving a B- minus or C player the the freedom to be their own boss in their own functional area is so motivating that they will work 80 hours a week 200% more than an A+ player. And you end up getting just as much but just in a different way. And so I I knowingly let them make decisions I knew would fail. When I started the company everything that was a bad idea I'd be like no that wouldn't work and here's why I did it. And so of course almost everything out of people's mouth I was criticizing. Do you think anybody had any more ideas or wanted to share them or do you think they did anything? Then I found myself micromanaging and doing everyone's job for them. I was exhausted. I was working literally 7:00 a.m. to 8:00 p.m. at night, no time for my family and I was like I this isn't scalable. And so I finally flipped the switch one day and said you know what, try the other extreme. Give them complete freedom and see what happens. What what triggered you
product. We were a better company. Um it's just it's everyone's happier. People work their butts off. I don't you know, I don't I can trust them.
You said that you flipped the switch like what something must have triggered that like now you can go to watch your kids soccer games. So like
what why just I saw the misery and the the tension on every call and that nobody was doing anything and I was doing the work for everyone and I was just breaking. I was like I I cannot do this. I'm I'm 90% doing and micromanaging and 10% leading. Now I do 90% leading and 10% doing. I love it. So you know, what what does structure and culture look like inside the org now? You mentioned complete freedom. Is that still the way or is there Yeah, I mean I did I used to I used I used to have a a template for how to write an email. What font? Blue font nine Arial like subject line has to be this way. You have to
drive me crazy. That that's what Procter & Gamble does around the world. 200,000 employees all write the same way. Well, we're not Procter & Gamble. I got to get over it. You know.
I love it. I love so some learnings on on running the team as well from your your executive experience. I I used to have like a weekly template for every one-on-one meeting that they had to fill out and reporting every two weeks and it was just so heavy. There was just such a I was putting in like corporate Fortune 500 quality management into a startup. It was just stifling everything. Like one day if we're huge I'll I'll try to insert that, but I've got to put the cart before the horse. Yeah, I mean it's it sounds like
it sounds like you and everybody else is having a lot more fun now. Everyone's having a lot more fun. Now we could be if we were more successful we'd be even more fun but there's things happening this year that that'll put it'll put that kind of extreme fun in the equation. Well, let's talk about that. What's the strategy to get there? You mentioned you don't need to hire you know, more people to grow faster. It's it's more nothing to do with internal or with hiring or or processes or culture. It's more we AI coaching is a category that three years ago when we launched it didn't exist. Wow. And so trying to sell and market to something nobody's looking for or knows what it is is exhausting especially at the enterprise level because that means they don't have a line item budget for it.
no budget. There AI code that doesn't exist. Where do I where do I put this? Right. So people loved our product. I if I did get meetings or sales people got meetings, people think oh my god this is amazing. What's amazing? Yeah, yeah, we'll trial it but then we just fizzled out because there was no mandate from their boss saying do this. So the biggest change is in the last three to four months basically by last fall into this year 30 companies got VC funding to do AI coaching. Wow.
Harvard Business School HBR magazine, McKinsey Conference Board have all come out with all these reports saying that AI coaching is the biggest space and opportunity for AI in the corporate world for HR tech. So it is the hottest category. Companies now are reading this. There's webinars every week. So the whole industry is doing marketing. I don't have to educate. So now instead of educating on a call what is AI and why do you need it? They're finding us and we're on a call. They know what it is. I can just go into why we're the best product in the market against the other five they know. Um so although it's much more competitive it's much easier to sell in that environment. And so that's what's happening uh it's AI coaching is here and the buyers have a budget, know what we do and now it's just kind of a feature function comparison and letting them experience it versus other tools. What what is one of the most valuable things that you know, you you would say you have against the the competition? Yes, so most AI coaching around leadership or talent development or collaboration they're just putting a layer on top of an LLM like quad or ChatGPT or copilot. Yep.
But it's not personalized. That's the biggest difference. We actually have a psychometric instrument that we used for recruiting back in the day where you give 10,000 employees or 100 employees this 10-minute personality test. And now the system ask Aura our coach which is 24/7 in any language verb uh voice activated or typing you can ask a question let's say you have a team of 10 people you just got promoted to this 10 people. Um you know, you can literally be like what are the dynamics in the culture of the team I'm about to manage starting tomorrow? And it's going to go through the 10 people their 20 pages each of their psychometric report. 200 pages in one split second and tell you oh this team are all decisive mavericks. Here are the dos, here are the don'ts. Okay, who's going to butt heads with me? Who's going to have conflict? Oh Mary, why? Boom. What should I do? So forming norming storming that takes three months you get in five seconds before you meet your first meeting with your new team, right? The other products don't have that. You ask how do I manage my team? 10 different leaders will get the same answer. Generic leadership tech tips. Ours is personalized and contextualized to the people involved. That's the biggest difference. The other difference and that's a huge moat. Nobody can develop a scientific instrument for like 10 15 years. Um and copilot and ChatGPT will never know you well enough to give advice based on you just asking questions, right? So we we don't have to worry about getting disintermediated by AI platforms on the psychology. Um the other difference is we're seamless. We're in workflow. So just like Grammarly got rid of the dictionary and the thesaurus and nobody in their right mind would ever buy those instruments again. No one will ever buy a personality test again. We give ours for free. There's zero value for you to take a personality test and then never look at it again. Ours, like Grammarly, is in workflow. So, you don't have to sign into a portal. Ours is in Microsoft Teams. Ours is in Zoom video. I'm on a Zoom video call. What's the culture of this meeting of these people? They're not listening to me. Why am I butting heads with Luis? I I need to get him to get to yes. Um you write an email and I'll look, push the button that rewrites the email for your audience the way they like to communicate. Right? You're in a calendar meeting, it'll tell you you're in the meeting before the meeting even starts. And who to assign what to and how to redo your agenda based on the dynamics of that future meeting. No co-pilot, no other AI can can do that. So, we have personalization with psychometrics and we're seamlessly interweaved throughout all your platforms Slack Teams Zoom Cisco Webex, you name it. Those are two big differentiators that nobody may have today. Yeah, so it can be implemented in their view workflow once they're on-boarded, can be implemented inside uh their their in You don't have to go anywhere. They're in, you know, which is amazing. I think that that's one of the biggest like gaps that you just have to go somewhere copy paste. Dude, no, it's it's here. It's with you. It's your coach coming. Well, and I think, you know, I I just imagined an executive going to meet an international team of 20 people and having never dealt with that culture before, being able to go and, you know, analyze that more and say, "Okay, how do I deal with, you know, a Latin American culture if I am, you know, an American executive and I'm, you know, managing 20 sales
Sorry, that's a great example you brought up. So, I worked 20 I left the US at 22, came back at 42, okay? Worked I speak five languages like English, worked in Germany Brazil France Spain Italy. Um Abu Dhabi, Dubai, right? And I always got a culture coach at these big companies. They would pay $40,000 every week. I had two-hour sessions for like a month, 2 months. And it would just kill me that they'd say, "Okay, well, all French people are this way. All Brazilians are this way." I've always dreamt, and we now have the product, a culture coach as a one of the modules in our AI coach, where if I'm working with a Brazilian guy named Luis Centenario or whoever I'm working with in Brazil, I can write their name and it's going to tell me how Luis is similar to his Brazilian culture, but where Luis is different. So, it brings in the generalizations that do apply to that person, but also personalizes and coaches you how to work with that person based on who they are, because working with all Chinese is not the same. Just like working with every United States citizen is not the same. And so, it's the only tool in the world that has got the culture coaching correct. Wow. Yeah, I didn't know you spent 20 years Is it 20 years outside of the US? Where So you
at 22, came back at 42. So, you got German, English,
10 years Latin America. Yeah, um German Spanish French Italian Portuguese, Italian German French Portuguese Spanish, Italian, and English. Wow.
So, and and then you hired internationally as well? Oh, I was I mean, I was managing that tens of thousands of people over the world. So, I I My whole career was hiring people from all different cultures. What You know, you know, what what what did you see in terms of, you know, executives in Italy versus France and, you know, what Were were there big differences or, you know, what was an an an executive in the US as an executive in, you know, Germany? It seemed like in terms of productivity, tricks and tools and the way people think, they're almost all the same. Like there's there's an action-orientedness, the way they take notes in a meeting, their follow-up, their decisiveness to follow up. All So, in terms of like how all these people think productivity-wise, you know, in in actioning and willing that to happen, very similar across every culture. The way they operate in meetings, the way they operate with human beings, the way they lead, completely different in every culture. The way you lead in France would guarantee you to be the worst leader possible in the US. And the way you lead humans in the US would guarantee you to be the worst leader in France as an extreme example. Those were the two most polar opposite culture differences in management that I found. The Germans were much probably the closest to the US uh in terms of uh with the different cultures I I I came up against. Yeah, I've read it in books, uh you know, like the culture map from from Erin Meyer, but never, you know, firsthand experience. Uh you know, you lived it. So, you were I almost got fired my first 4 months of work. I almost got fired in France. Why?
Cuz going there thinking I was the greatest leader in the world and I was a hired head on it by Russell Reynolds because of my leadership ability. And then the CEO of my company, 600,000 employees, right? So, the guy, my boss, manages 600,000 employees. Today he manages 1.6 million at the third largest company in the world, right? So, he's, you know, he's a really good leader. And he's like, "Listen, Juan." And you know, secret meeting. I was like a top secret project. "What are you doing in your stores?" It was a retail concept. "Your people in your store hate you there. We're getting these horrible reviews that you're the worst leader." And I'm like, "Well, let me describe what I'm doing." "I meet with them every morning. I ask for their opinion. I ask for their help to train me cuz I had no retail experience, right? In the US, you put people in power because of their strategy and their potential long-term, not because they're experts in the retail science, right? So, your team will train you because if management says, 'Hey, here's Juan, your new boss. Train him to make him as good as you.' Because all the subordinates had the expertise, they're going to train up." So, I told this guy, my boss, the CEO, like, "I go in, I ask each person to train me on different areas every day. I ask for their opinions when making strategic decisions. I get buy-in. I I I don't micromanage. I I That was great. That was like a great And he's going, "No, no, no, but c'est c'est pas vrai. C'est pas vrai." And I'm like, "What what's wrong?" He goes, "No, no, no, no, no. In France, you you were the boss because you know how to do what everybody does and you do it better. And they can never correct you or be right because then they think they should be the boss. You need to go into the store every day and criticize every employee and find things that are wrong every single moment of the day to prove to them why you're the boss. And constantly have them on their back heels." And I'm thinking
You did it. You changed. It sounds miserable. So, I was like, "Okay, I was getting paid a lot of money." Um yeah. Um So, how did you do that? How did you completely change your leadership style, you know, So, I'm you know, when you when you speak five languages like English and you are agile and you grow up in a country where nobody understands your culture and you have to become a chameleon like you know, every 3 years I lived in a different country and absorbed that culture to live. Like I wasn't like an expat to hang out. I mean, I was like reinventing myself every 3 years for 20 years. Wow.
You you get the ability to flip a switch and just be something different, like actors, right? Like when Tom Hanks went from like comedy to Philadelphia, right? People were like, "Whoa." Um and it's not inauthentic. It's just you're able to get rid of your ego and all the stories of who you are and how you're supposed to be and you're actually able to regulate yourself based on the moment and be in the present, not based on the history of stories of your childhood or your culture or your religion or what people or society have told you. So, I part of never fitting in gave me this superpower, right? So, I never fit in, right? I never I never fit in. That's not a great thing, either. But, it gave me the superpower to be anything. Um and so, I literally flipped the switch and the next day went in and treated everyone like crap. Made everyone feel like they were idiots. Showed them how much more I was than them. And my store went from 480 stores in France from like number 460, like bottom 10%, to the top five performing store for the next 3 years. Then I got promoted to be CEO for the United States and Brazil. Um so, it worked. Like leading in France is very different than leading in the US. Yeah, and then when you got from the US, you have to be clear on the deliverable. You have to be clear. You have to tell people what you want. In France, the more you are directive and tell people clearly what you want, the dumber you come across and the less they respect you. You have to be able in a nuanced French way. Bizarre in French, by the way. This is not in English. Wow.
to be able to tell people what you want without saying it. So, the skill of being a parent of a teenager where it's really hard to get your teenage kids to do something without telling them, how do you get a teenager to do what you want without ever telling them? This is what it's like to lead in France for everyone. Wow.
I even got to be able to do that, which I even amazed myself cuz I thought I wouldn't be able to do that. Because you can't tell someone an order. There's no orders in France. Everything is in the form of a question. Can you Can you Would you Can you give us some French? Say it in Let's hear it. Let's hear some of it. I don't know. Peut-être faire Euh cette live demain au lieu de de vendredi. Like would you Would you be willing to do this tomorrow instead of Fri- Friday. Like but it's always a question.
You can never tell people. You have to look at them with respect and that they're equal to you even if they're the janitor. That's why That's why when Americans come and they're like, "Oh, the service here sucks." Because Americans talk down to French like, "Hey, you're a service person. You I'm telling you what I want." Like, no. When you talk to the bartender, they feel like they're a doctor and you should respect them like your doctor. So, imagine the energetic vibration talking to a bartender, very different than when you're talking to your doctor who's saving your life. They expect the same energy. I agree with that. And that's I think I think you're giving everybody here some really good tips on on how to get better service as well. In the rants, always grovel like you need them. You will get the best service you've ever experienced. So, then you went from, you know, turning around the store, making it the most successful, getting promoted, and now you're back to leading in the US and Brazil. Did Did you need to adapt again or was it No, yeah. For the first time this It's I I know how to do this. This is I enjoy making people happy and not criticizing more than the French way.
The French way I mean So, you were happy to be back. You were happy to be speaking in English. to be back out of France. I mean, France I went to France thinking, oh, here's another great superpower country. Like, we always have this, like, you know, attention you I've never had more pity for a group of people in my life than that after I left France for 5 years. It is the smartest population I've ever encountered who are the most who are the most miserable in their day-to-day life. Wow.
No one ever fulfills their oppor- their potential. It's it's so demoralizing. Or you see a lot of great, you know, friend, you know, French software companies come in, where do they move? They move to San Francisco, they start building here in in in the US. You know, you don't really see a US founders going move to France or anywhere in Europe to go and build.
France France has the potential to be one of the greatest countries in the world, but their system is so rotten. And that's unfortunate for like Like, it's really sad. Like, even the word So, entrepreneur, entrepreneur, it's a French word. Really?
does not exist in France anymore. What?
That's from the 16, 1700s, when they were the greatest, you know, inventors of so many things. Today, they don't even know what that word means. That's crazy.
And only the only the rich have opportunity. There's no meritocracy. So
Their Their Their version of Mexicans are the the North Africans, the Algerians, Moroccans. Those people six generations in are just as poor as they were six generations ago. It's crazy. It's so sad. And you like going back to your team now, so, you know, you you went from went from millions of you know, hundreds of thousands, millions of of employees, now you have 12. Are you hiring internationally for your team as well or do you like everybody in, you know, a regional location? What What does that look like for you?
We have people in Mexico, France, England, and Brazil, and Costa Rica, but they're kind of distributor partners. We're kind of letting them we're just licensing our product to them to sell locally. So, it keeps the headache out of having to hire for those territories and cultures. Wow, brilliant. So, you know, you you know how hard it is to go and do that, so it's I'm willing to give up 20% of my revenue to avoid that headache at this stage of the company. No, it makes makes complete sense. Um, so, you know, some new founder that doesn't have your experience in hiring like you know, what what what are a couple tips that you would give them in making their first hire? They're listening to this podcast trying to figure out, hey, how do I hire my first sales person? How do I hire my first marketing, my developer? Um, what what should I do? What what are some tips that you can leave them with as we wrap up your one? I mean Salesperson, two references. Structure the deal where you don't give too much equity if you're giving equity unless they make it 3 months, cuz you really won't know if you want to fire them or not until after 3 months. So, the comp package and and not that they're not um uh investing equity for 3 months, but if they don't make it the 3 months, they lose that those 3 months, right? Like, um and and do reference checks. Um Also, sales, hire someone if if it's a more senior sales person from your industry, from your vertical. Like, you lose so much time someone learning how to sell that product or that that concept, right? Um that's sales. Uh Use a behavioral assessment, like a personality test, to understand the culture of your small company, where you are, what you think you need to where you need to go, and where that person fits and why you're hiring them. Um that's another top tip. And then, software engineers, I would recommend going to Colombia over any other country in Latin America. Next, I would say would be Costa Rica, Argentina, Brazil. But, Colombia, I've worked with all those countries. I've gotten the best results from Colombia. Amazing. I'm from that right now. Uh I saw the the architecture in the background. I was like, that looks like Colombia. Are you in Bogota or Medellin? Medellin. Medellin, yeah, it looks the beautiful valley. Thank you so much for sharing your wisdom and knowledge on who we hire and uh look forward to wat- watching you grow and accelerate Ask Oracle this year. Luis, thanks so much. You ask great questions. Thanks for making me sound smart.
Anytime, Juan. Thank you. Thank you. Thank you. Cheers.
