Pearl AI: The "Let Them Run" Playbook for Scaling with AI | Ben Plomion (Podcast 569)

In this podcast, COO Ben Plomion discusses his transition from a marketing executive to the COO role at Pearl AI, a dental AI SaaS company. He explains how he leveraged cross‑functional marketing skills to manage large teams, built G&A functions (HR, finance, legal) from the ground up, and shifted the company’s cultural framework from static values to dynamic operating principles, including the "let them run" motto that empowers teams to act without excessive oversight. Ben shares practical tactics for creative problem solving, such as delivering interim value to customers to improve collections, and describes how Pearl uses AI tools—particularly Anthropic Claude—to create a company‑wide knowledge base, analyze large event datasets, and generate actionable insights. He outlines the company’s scaling journey from Series A to Series B, the adoption of OKRs, and the rollout of a printed Pearl magazine for onboarding. Ben also references learning resources that helped him, like Cameron Herold’s book and a Harvard Business Review article on the CEO‑COO relationship. Throughout, he emphasizes the importance of connecting the dots across departments, making decisions with imperfect data, and fostering a culture of experimentation and rapid execution.
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Sometimes being creative does not mean something incredibly exciting and flashy. You could have a set of issues as a CEO, you have to think in a creative manner to go and solve them. If you're trying to improve collections from customers and you realize you are billing the customer before the customer gets a service from you, it's an issue because the customer is going to be disappointed. So you have to think creatively about what can we give to the customer right now as a value with our software, and then the remaining will be delivered maybe in 1 week, 2 weeks, but that allows you to build a customer on the spot as to wait for 2 weeks to build a customer. It's a creative way of solving a very tactical kind of dry issue that CIOs come with a sort of background because they used to think about problems in a very creative manner.
Love that example that you just gave. What has shifted since then?
So that's a funny thing. I'm glad you're asking the question. When I—
Ben is the Chief Operating Officer at Pearl AI, the leading AI SaaS platform in dentistry, and brings more than 20 years of leadership experience across AI, computer vision, and emerging technologies. Before stepping into the COO role, Ben built his career as a growth and marketing executive, including serving as CMO at Dibs and Chief Growth and Marketing Officer at GumGum. In this episode, we talk about how to successfully transition into the COO seat from other executive roles, how to identify and learn the skills that actually matter, and why Ben believes principles outperform core values when it comes to scaling teams. We also unpack his operating philosophy. One of the new mottos that he has released to his team is the concept of let them run. We'll talk about what that really means and why empowering leaders is essential for building fast-moving, scalable organizations. If you're a COO or an aspiring second in command, this episode is for you. Let's dive in.
Okay, a quick note before we continue. Today's episode is sponsored by our trusted partner, Next Level Growth. They work with CEOs and COOs who are growing fast and starting to feel the strain, seeing some priorities slipping, execution slowing, and even leadership being stretched thin. Next Level Growth guides leadership teams to get aligned, establish real operating rhythms, and execute better without burning your people out. This is practical operator-level work, not theory. Check them out. Proactive always wins over reactive. Details are at cooalliance.com/nextlevelgrowth. Partners. That's cooalliance.com/partners and go check out Next Level Growth.
We are live with Ben. Welcome to the show.
Thank you, Sivana. Thank you for having me. I'm excited to be here.
Me too. Let's start right away. Tell us a little bit about the company that you're with, Pearl. What do you do and who do you serve?
Yes. So the company is called Pearl AI. What we do is we operate in the healthcare space, more specifically in the dental industry. The company was incubated, I guess, in a larger company called GumGum here in Los Angeles. What we do is we use AI and computer vision to elevate the standard of care of dental industry. Particularly, one of the things we know for is AI diagnostic. So we have a number of engineers, we have a number of algorithms, and we can scan dental X-rays at scale, find pathologies, let's say a carie, for example, and help doctors educate the patient through the software that we offer to them. The company is about, well, not about, the company was established in 2019 and I joined 2 years ago as Chief Operating Officer. Our customers are dentists in the US, in the UK, and beyond. We have 20,000 customers as of today, and I'm excited to be here.
Amazing. Okay, tell us a little bit about your personal journey, a little bit before Pearl, but mostly how did you get connected? And tell us a little bit about that initial kind of hiring process you went through.
So the founder of Pearl is also the founder of the company I mentioned previously called GumGum. When I was at GumGum, which is a large ad tech company, advertising technology company in LA, it is a $1 billion company, 600 employees organization. I was a chief marketing officer and then I became the chief growth officer. Our CEO, his name is Ophir Tens, was the CEO and founder of GumGum and is now the CEO and founder of Pearl. So we have worked together for maybe the last 10 years. I have been his Chief Marketing Officer, Chief Growth Officer, and now Chief Operating Officer. So I like to go around through different executive positions.
Did you get hired originally for the COO position or CMO?
I was hired for the CEO position back then. That was 2 years ago. The company had found product-market fit. The company had traction with dentists in the US and beyond. And I got this, it's not even the phone call, I got a text message from Ophir saying, hey, I'm ready to scale. You know, we have good traction in the market. I need someone who can come in and help me organize the company, help me scale different operations, sales, customer success, accounting, and finance. And, you know, I'd like you to be this person. For me, it was a no-brainer because I've known the CEO for a long period of time. I know the company was going to be very successful. And I figured that even though I hadn't been a COO before, I will be able to transfer some of the skills I had as a leader early on in previous companies and bring them to Pearl, which is exactly what I did. The pitch, to be precise, was, Ben, I'm a great CEO, I'm a visionary, I'm a product person, I like to do investor relations, I like to do business development, but when it comes to running the company day to day, looking at things like accounting, looking at things like sales performance, looking at things like legal and compliance, I'd rather have someone else do it and you're gonna be my dumpster. I'm gonna dump everything I can into that bucket. You're gonna handle those things that way I don't have to be concerned about those things and I can focus on being a great CEO. So the pitch was very compelling, very easy to understand, and obviously I got very excited and, uh, jumped in.
What were the skills that transferred easily versus the ones that were really difficult?
I'll start with the easy ones. In general, I think if you are a leader, if you are putting at a C-level in a midsize to large company, you have a very large team. Typically, I had more than 20 people reporting out to me, so I knew how to manage a large organization. I knew how to communicate internally and externally to a variety of stakeholders. I knew how to work with teams from different organizations. So when you're marketing, you work with marketing, communications, product, sales. So you develop this sort of cross-functional ability that you can take any role that you go to. And I think the COO by definition is the ultimate cross-functional role because you have to communicate not just with marketing and sales, but also HR and customer success. And product engineering. So that was really, um, a talent that I think I had was very easy to apply to the new COO role. Now CEO takes you to one or two levels deeper because not only you have to understand your teams, but you also have to understand those teams very deeply. You have to understand if you're making a change, let's say in a sales plan, let's say you're changing the way a bonus is being structured to a sales team, this would have an impact on a number of things. Let's say on collections in terms of, you know, collecting money from customers. Let's say in terms of HR principles, you wanna make sure you're being fair and equitable. If you make a change for the sales team, do you make the same change for the marketing team? So being a CEO means you have to go 1 to 2 levels deeper across every single team. You don't have to be an HR expert, you don't have to be a product expert, but you have to understand enough to ask the right question across every single team. Otherwise, it's difficult to connect the dots. And I think one of the primary job of the CEO is to connect the dots across the organization. Hmm.
How did you go about understanding those pieces at a deep level? Like when you say it's so important to understand the team super deep, a couple levels down, how do you actually go about that while also not getting trapped in the weeds?
Yeah, I was lucky that I knew, I'd say a third of the business. So a third of the company would be sales, marketing, customer success. I was proficient in those areas because I was a CMO before. You know, there's one more third I had to learn, and there's a third I'm still learning. In terms of the third element of the company I still have to learn will be what we call G&A, general administrative functions. So I had to learn how to operate with an HR team, human resources. I had to learn how to operate with finance and accounting. What's the difference? Finance is future-forward, accounting is really looking at the historical data. I had to learn to operate with the legal team. I had to learn, um, how do you report quarterly earnings to the investors? And the way I learned this was, you know, by doing it. Essentially, you start, it's day number one, you learn that, and this is very common for CBB's organization, you know, consider companies that have product-market fit, that scaling, but not quite, you know, profitable yet, you learn that the financial, um, discipline that you have may not be optimal. So this is day one. This is Ben. I'm at Pearl. I'm realizing, oh my goodness, we don't have one person dedicated to finance and accounting in this organization. Everything is being outsourced. It takes some time to get a response. And the people that we hire, those outside fractional consultants if you like. I just don't have the sort of skin in the game. So you learn to in-house things. You learn to go and hire a head of finance, for example. You learn to understand the differences between, you know, between EBITDA and cash flow management. Those are very different things. So you learn by doing, you learn by making small mistakes. You cannot make very large mistakes, but you can make a lot of very small mistakes. And along the way, You get more educated on the space and now able to sit down with the CFO and have a conversation about, you know, let's say, uh, depreciation cost or tax implications. Again, you don't have to be an expert, but you have to be dangerous enough to ask the right questions. And then you proceed to the next team, which is the legal team. So you learn the differences between corporate lawyers, lawyers who represent companies when it comes to equity investor relations, and then you have commercial lawyers. Commercial lawyers are dedicated to special deals and contracts with customers. You basically learn on the go. And none of that is really rocket science. You just have to sit down, speak to a lot of people, get some help from experts, and be logical enough to understand what actually needs to be done right now and what needs to be postponed maybe in the next year or two years because it's less of a priority. It is very easy as a CEO to get lost in the details of each department where your perspective is really to understand how they interact with one another and make a decision in department A that will have a potential impact on department B. That is really the role of the CEO. I give you an example. If you decide to work with the customer success team and change their goal from, let's say, um, NPS, net promoter score, to let's say a goal that is more, um, focused on retention, then when you make that change, you also have to understand the change is gonna impact the sales team. If you're asking the customer success team to have better customers, happy customers, then the value proposition you deliver to the sales team has to be aligned with the value proposition the customer team is gonna deliver to the customer. So you learn to connect the dots.
Hmm. It seems like an overall theme I've heard from CEOs that are working at larger companies is they tend to mention that way more often about connecting the dots versus CEOs that are working at smaller companies, they seem to get caught in the weeds more. So how do you keep yourself from getting caught in the weeds when you're going through that deep process? You're trying to learn, you don't wanna make big mistakes. How do you ensure that you are able to connect all the dots without getting sucked in?
It depends on the stage of the company, I guess. When, when I was hiring to Pearl, the company was a Series A company, right? Meaning Series A company is defined as you raise a bunch of money, you know, we've got clearance from the FDA, Federal Drug Administration. We have some product market fit and we have a number of customers. So when you come to an organization like this, I has, let's say, I think we had 40 employees back then, 4-0. You are the G&A person. You are the one person doing HR, accounting, legal, to some degree compliance, and a bunch of other things because you don't have enough traction yet to hire a team. So I was an individual contributor for the last 6 months at Pearl. I was by myself. And, and that joke I like to tell the board, I'm G&A, I'm the only cost you're ever gonna pay at least this year for G&A. And you learn to do things by yourself. You learn to produce financial reports, you learn to develop, let's say, you know, an HR playbook for employees. You learn to develop a system where for very basic legal questions, you can answer those questions without having to go to a general counsel because you're very cost-centered then. So you learn to do some of the things, but quickly you realize I'm not that great at going that deep in terms of finance or accounting, but operations. And then you start bringing some experts. So I hire a head of finance, I hired a head of HR, I hire— he was actually here, but we positioned someone as a head of operations. Um, so I think the answer to your question, when you're a very small company, you get to do a lot of things, wear a lot of hats. And as the company gets bigger, you realize I should probably not spend a month looking at employee benefits. You know, this could be done by someone better who's more qualified. Let's have this person do employee benefits. That way I can spend a bit more time with the investors or the customers or employees. And as you move into a Series B company, which we did, then it's a no-brainer. Your talent becomes your ability to connect the dots between the different departments, and you cannot allow yourself to go too deep into the weeds. Unless this is something very critical for the business. Employee benefits are important, but the business is not gonna die or live because we have better employee benefits. The business may die if we don't figure out a way to incentivize our customer success team in retaining our customers, and we don't connect the customer success into the sales team, as I mentioned earlier. So you have to pick your fight, and it's very difficult because there's a lot of things on your plate.
Right?
And that becomes a conversation with the CEO and investors. Where should I be spending my time? You agree on key priorities for a quarter on a couple of big bets, and that's where you spend your time and try to outsource everything else to people you can trust. So sometimes, you know, outside agencies and partners that we have. Hmm.
Before we jumped on the podcast recording, you had mentioned when you found yourself in the CEO position for the first time, you actually read Cameron Herold's book, and we were talking about how there's very few resources for COOs, and sometimes you, you find yourself in a role and you have to learn all of these things really quickly. It sounds like you're saying that you were asking a lot of questions to the current team, learning things on the go. I'm curious, were there other resources or places that you were looking to— like, when I think of learning finance at the level that you need to learn it for Pearl AI, that would feel very overwhelming to me because I don't consider myself to be great with financials. What, what was your process for getting outside information, or was it just asking those questions, or what was that process like?
So when I got— 2 years ago, when I got a text message from Ophelia, who's now my CEO, and asked me to jump on as a CEO, my intuition was to do a little bit of research And I did two things, just two. Number one, I got Cameron Herold's book and I read it, probably memorized, you know, some of the key takeaways of the book. For example, this idea that the CEO is gonna be throwing balls at you is 100% accurate. This is exactly what a CEO comes in and do. You get balls being thrown at you in terms of going and figure the financial reporting or go and figure out the company culture and you have to go and take those balls and just, you know, come up with something that is beneficial for the CEO and the company. The other thing I read and studied is a Harvard Business Review article. I'm sorry, Harvard Business Review article called CEO, the Second in Command. And that may have been the inspiration of Cameron Herold or vice versa. Maybe the article is inspired by Cameron Herold. Who knows who comes first? This article, if you go to Google and look for HBR CEO, second in command, is I think 67 pages, very dense and detailed article that really trying to figure out what are different type of CEOs. And I think the challenge with CEO, all the different types, you have the go-to-market CEO, someone like me initially comes from marketing and sales background. And whose primary skill is gonna be, you know, on the commercial side. And then you have the ops-driven chief operating officer who come from a different background, finance, accounting, operations. And those are very different individuals. The HBR article laid out, I think it's 6 or 7 different archetypes of CEOs. So my first, the first thing I did is was to read the article and understand where do I fall under. Right? What am I the type that is the most needed right now? And my type is the complementary type, which is we have a CEO who's again, a product visionary, who's amazing with investor relations, amazing with business development. But there's a number of things like running, you know, bonus plans, running a customer success team, understanding the, the company culture and coming up with operating principles that just not something that is what it does best. You basically have to find your place. And I think the most challenging part for the CEO is to go identify that place. How does it look like? Particularly in the context of companies evolving over time. I was hired as an ops-driven chief operating officer because we had to build the accounting team from the ground up. We had to build the HR team from the ground up. We had to build processes. We had no bonus plans in this company. I had to build them all, but then I realized 2 years later, now I'm shifting a bit more into a go-to-market COO type because the next need for us is to grow revenue, become profitable, you know, upsell and cross-sell our customers. So I'm moving back into the sort of a CMO mindset, right? And I think in some way this new role I'm into is kind of a combination between COO, CMO, and chief revenue officer. Which is exactly where I belong. Now that we have operating principles, we have an operating rhythm, we have the function of G&A being built out, I'm going back to what I know and do really best, drive revenue for the company. But I think my advice for any CEO, and I wish I was given this advice when I started, is like there's different flavors of CEO, trying to find where you're gonna add some value and try to specialize in this area.
Hmm. What would you say are the key things from being a CMO that you think every COO, no matter what archetype they fall into, would be an amazing skill for them to learn, or that has been really useful that you're transferring? Is it the cross-functioning of, of team or like leading team like you were doing?
It's two things. Number one, the ability to operate cross-functionally is very transferable as a skill. Because if you're a CMO, you're driving a marketing campaign and you're gonna have to work with your media relations team. You're gonna work with your media relations agency. You're gonna have to work with your automation, marketing automation team. You're gonna have to work with your creative team. You're gonna have to work with the sales team. So you end up as a CMO working with 6, 7 teams for a marketing campaign. A CEO is someone who's doing that on steroids. If you launch a new, let's say, company playbook, why, let's say you're building a playbook for new employees, it's touching every single department. So you have to work with the marketing team, but you also have to work with the accounting team. You also have to work with the product team and engineering team. So I think that's a big transferable skill, uh, that could be applied. The other one is think creatively. There's one thing I miss in existing role is when you're a marketer and you are on the spotlight and you have those flashy marketing campaigns and you go to fly to Germany or other places to speak about marketing ideas, it's kind of fun and super creative and very inspiring. I don't do any of that. What I do is much more internal focused. What I've learned though is some of the creative skills that I had as a CMO can be applied as a CEO in a very different capacity. Am I going to be the person coming out with an amazing marketing campaign on Facebook? Not right now. But am I going to be someone who can apply those marketing skills to produce, let's say, a Pearl magazine? A Pearl magazine is something that we're releasing in a week that is the story of a culture of the company that we can hand out to an employee. Yes. You know, it's something I can do that very effectively. And sometimes being creative does not mean you know, something incredibly exciting and flashy. You could have a set of issues as a CEO. You have to think in a creative manner to go and solve them. I give you one example, which is probably a very dry one. You know, if you're trying to improve collections from customers and you realize you are billing the customer before the customer gets a service from you, it's an issue because the customer is gonna be disappointed. So you have to think creatively about what can we give to the customer right now as a value with our software, and then the remaining will be delivered maybe in 1 week, 2 weeks. But that allows you to build a customer on the spot as to wait for 2 weeks to build a customer. It's a creative way of solving a very tactical kind of dry issue that CMOs come with a sort of background because they used to think about problems in a very creative manner. Hmm.
I love that. And, and speaking of the creative piece of it, You mentioned you guys are rolling something out for the culture of your team. Is that right? Next week?
Yes, we, um, I told my, uh, my team that, um, some of my marketing, how can I put, my marketing mojo was, you know, I want to test out my marketing mojo. It's still there. Can I still come up with something cool and exciting? And I went to the marketing team saying, listen, we have this dilemma where we have a lot of employees coming to this company because we're hiring a large number of employees as we go really fast. I say, frankly, getting an email with 10 links to Google Doc is just not that exciting. You know, what if we come up with a Pearl printing magazine? You know, an old school, 25, 30 pages printed magazine that's very well designed, incredibly attractive, very appealing in terms of aesthetics, that has a bunch of interviews with executives. That has a clear sense of what is our company values, what are the operating principles that we have, a clear guide that includes one article I wrote about the future of dentistry that I think is important for new employees to go and read. And then you can even attach a dental glossary if you're new to the dental industry. So we produce this magazine, it's gonna be shipped in about one week. And something that I think if you're a new employee coming to the new organization, you're gonna be much more excited to read than a bunch of blue links.
That's so cool. That, uh, actually reminds me of something that we did when we were scaling really quickly. We were like, how do we transfer all the things that are in our executive team? Sorry, my voice is going out today. How do we transfer the, the things that are in our heads to our team as quickly as possible without having to repeat ourselves? A million times and you're constantly repeating yourselves and reminding of core values and principles. However, if there was one common place for all of those to be listened to when someone forgets or we're like, hey, go watch that video and they can go watch it for 20 minutes instead of us having to share it again. We ended up building out a video kind of onboarding portal, which wasn't just about our company's core values, but it was about how we think about business. Because it wasn't, we always tried to teach our team members when they're onboarding new people, teach people how to think, not what to do. And that really allowed our team to develop kind of this common language and common mindset about how we think about problems and creativity and team culture. And what I did on my teams specifically for Just Buy Teams was I would have my new hires go through all those videos and they would actually come up with like a presentation for the team that they were working with where they would come back and share a presentation on what they learned and anything that was around a specific principle or a core value. And there was a few places where they could bring an example of a time already in their life that they displayed that principle or lived in that core value. And so it was a really great way for my team and them to learn about each other while also being constantly reminded. Every time a new hire came in, we were repeating those principles and those core values without them having to go re-listen to it again. And so when you start talking about creative culture things, I totally light up because I love culture. I would love to go a little bit deeper on that with you, actually. What are some of your guys' culture principles or ways of operating that might be unique to you?
Yeah, I wanna go back to a point that you made that I think is very important to me. One of the cardinal sins of being a CEO is you kind of have to repeat yourself regularly, remind, you know, employees of operating principle, where to go and find stuff. And I think what you did was very brilliant because you really forced employees to listen, you know, to these materials or read those materials and kind of like repeat back what they heard, right? I think one thing that we found to be equally effective is to do exactly that, plus have new employees comment on existing materials being available to them and make them stronger over time. So 2 companies ago, we had this marketing playbook, welcome to Gum Gum, here's what you know about the company. If you came in as a new hire, regardless of your role, whether you are a VP or an intern, your responsibility was to take this onboarding guide and making better for the next person. It's awesome because it's forcing this person to read the thing, number one, because you're never sure they do, and to make it better. And this sounds like on day number one, you know, day number ones can be intimidating for a lot of people. You don't exactly sure what you're gonna be working on. You have a task and it's an easy one. Read the onboarding guide and make it better. And all the employees will get really excited. Okay, I can do something right now, contribute right now and get a win on day number one. So I found this to be incredibly effective in terms of boosting morale. And getting us employees excited. To answer your question on values, it's funny, we, we move away from values, company values, and we adopted operating principles instead. We felt that value had a sort of like negative connotation. We're going to put 3 words on the wall that no one's going to read. And we said, no, I think it would be more suited for us as a framework where we have a bunch of operating principles. So some of them have to do with agility. How fast can we move as an organization? How could we, can we take some risk? How can we fail fast or scale even faster? One of them, what is new to this organization, probably new to, I would say many folks listening to this podcast is the rise of AI. We embedded the adoption of AI into the operating principles. And what it means is that if we're judging you through a quarterly check-in as an employee, or if we are assessing your performance during the annual review, we're gonna be looking at your adoption of AI. So not only we have done that in a way that is very obvious and apparent, but also we have constructed a number of workshops and group sessions that way any employee, whether you work in product or whether you work in sales, feel like we're gonna support you in your adoption of AI. We have seen some success across the team. One thing I like the most is going back to your point that you made earlier, is the second cardinal sin of a CEO is having folks coming to you or coming to me saying, I'm not able to find a document. That's absolutely horrendous and happens all the time. You kill yourself putting together I don't know, a T&E policy, travel and expenses policy. No one can find the thing and you're like, I can't believe it. I told you 16 times where to go and find it. We talk about this during every single company call. You see, I cannot find it because documents are all over the place, different formats. And what we did is we use an AI knowledge base that allows us to scan every single document in Slack, in HubSpot, which is a CRM system. And also in Google Drive to go and find document. So it was something that solved a lot of issues for us, and most employees are now able to find a travel policy or holiday policy or maybe bonus guidelines using this specific tool. So for us, AI is very important. It's even more important to me. I probably spend an hour, 2 hours a day on AI by myself, right? This is how effective that is going to be for a CEO, because if you think about this, If a CEO can collect the data that we need to go make decisions and feed the data into, let's say, ChatGPT or Claude, then you can expect a pretty thorough analysis to come back. And of course, you have to refine it over time because it's never perfect. But I found AI to be a really good friend to the CEO. It has become really my assistant.
What tool is that that you mentioned?
The one tool I'm using is Anthropic Claude, which I found really powerful because it's probably the most popular tool when it comes to enterprise AI. It has different connectors to HubSpot and it has connectors to emails and connectors to a variety of apps that we're using. But also I found the tool to be incredibly thoughtful when I talk to I'm not paid by Claude Battlewedge. I have no skin in the game here, but I was a heavy ChatGPT user and realized some of the limitations that came with it, and I switched about a month ago to this new Anthropic AI, and I found the AI to be much more human. I know it's a hard statement to make, but much more conversational in the way I interact with it. I found the AI to be much more thorough, but I also found the AI to be very honest. Ben, I don't have an answer to that question. I'm gonna dig again and let's hope I can find something. So when you have the sort of interaction with an AI, it almost become like, uh, an assistant that is sitting near you available 24/7 and never gets tired. So I found this to be very effective as a COO. I haven't really used it as a CMO, but I can tell you my new role, I find it incredibly effective and very productive.
I've been on kind of an extended sabbatical over the last few years healing from some health issues, and that's really been the time that I've started using ChatGPT is in the last few years. And now that I use it daily on so many things, I look back on what I built before and I mean, The amount of things that I did that I could have used AI for, I'm like, I could have done this in literally 10% of the time. It's so incredible that it's available to us. There's a motto that you had mentioned in your preform that you often say is, "Let them run." What does that mean?
Yeah, let me talk about that, and then I want to give you an example of AI because I think this would bring to life some of the points I made earlier. Let them run is a motto or a tagline we adopted for our customer success team about 6 months ago. 6 months ago, we were going incredibly fast as a company. And, um, when you go really fast, uh, sometimes, you know, uh, you're seeing higher churn. Higher churn means some of the customers leave faster than you like. So we had this instance where we're launching a new product that probably was not as fun as it should be, and we saw a number of customers leaving us. We decided to organize daily standups and weekly walk sessions with the customer success team, with the team responsible for customer success and happiness and retention. And I realized really quickly that the team had all the answers regardless of their level of seniority, whether they are a VP or sometimes even assistant. They knew what to do. And I said, my job as a CEO is to bring you together and organize the issues that we're seeing, quantify the issues that we're seeing, and have you come back with ideas. And of course, that was very successful because that team is talking to customers daily. They know exactly what customers need. That team is onboarding customers daily. They know exactly what the pain points are going to be. So the team came back to me with a lot of ideas, said, what is stopping you from implementing those ideas? It's nothing really. And I realize, okay, I'm sitting on a gold mine here. Whether I go to the customer success team or the accounting team, they have the answers. And for some reason they're not able to implement those solutions. So we came up with this timeline, let them run, and I explained to them, it's very simple. I'd rather have you think about solutions, implement new solutions, than, you know, be frozen by indecision. So why don't you run? And if you go too far or a little too fast, I'll catch you and bring you back. And that's okay. I will never blame you for going a little too fast and too far. But if you freeze by indecision, then I have a bigger issue here. So that became let them run. And our customer success has been running ever since. Now I'm using this tagline for other teams as well. Like, um, you know, we have a sales team as well. Like, I think the intention is there is no reason to have those very heavy layers of management because it's stopping our employees from making the right changes. I give you an example. If you're talking to an onborder who's onboarding a, you know, a doctor, as we do daily, they may have 6 to 8 onboarding calls a day. They know exactly what needs to be done. Why should I stop them? Or why should someone on my team stop them from executing on those ideas? Let them run. And if they make mistakes, because they will make mistakes along the way, that's okay. Because in many cases, if you can catch those mistakes very quickly, you can rectify it and produce a much better organization. So that's the tagline we'll be using overall. And then to come back to AI for a second, I just wanna illustrate a point I made about The use of AI to be very, very clear. Of course, we're not gonna let AI make strategic decisions for us, even though it may influence how we think about a particular market. Let's say, you know, Japan or particular expansion of our existing territories. What I will do though is use AI as an assistant, particularly when it comes to data analysis. And I want to give you a very clear example. I'm stepping more into the marketing organization right now because we need some assistance in driving more ROI, return on investment, from existing marketing campaigns. I asked my team, the revenue ops team, the marketing team, the sales team, and the event team to put together a massive database that has a list of every single event we attended to last year, which is more than a couple of hundreds. I asked the AI to— sorry, I asked the team to put together a very long list of details that relate to each event: attendance, number of leads being generated, cost, travel and expenses, type of events, city, location, timing. We have about 25 variables. Then I fed this model to Claude for a weekend. We went back and forth a couple of times. I had to make some refinements because the AI obviously got it wrong in the first place and then got it right. And I came back with a 16-page report that's telling me you are overrepresented in a number of states, you are underrepresented in a number of states. If you do those 5 things next year, you would drive ROI by 25%. This is something that would've taken a very big brain maybe a week or 2 to produce. The AI did this over the weekend and mostly was waiting time because the AI was running as I was waiting for the data to come back. It is amazing what the AI can do in terms of ingesting a large amount of data and spitting out some, not just correlation, but also causation and recommendations for the future.
Love that example that you just gave. Have you guys already rolled that out or what, what has shifted since then?
So that's a funny thing. I'm glad you're asking the question. When I had the AI report, I asked myself, do I pretend it's mine? Or do I not pretend it's mine? And this is what I did. I organized a 90-minute session with, um, our head of marketing, head of events, head of sales, head of ops, about 8 people. I said, we've got 90 minutes. You have this 60-page report to read. You've got 30 minutes. It was written by an AI, and I was very transparent. This is how I went about this. This is an AI-produced report. You're gonna read for 30 minutes. We turn off Zoom. You're gonna come back in 30 minutes and we're gonna discuss the report. They came back 30 minutes later. Okay, why is the data? And you know what, usually what people do in large organizations is question the data. And I made a very bold statement. Nope, we're not gonna do that today. What we are going to do is to assume that 70% of the data is enough to make a decision, which is an Amazon principle, by the way.
Anyway.
Stop blaming the data and stop freezing by indecision. This is way too easy. You have to assume the data is correct. You give me the data, by the way. If it's incorrect, it's on you. This is the data. You're gonna go make decisions. And then the conversation shifted to, okay, we're gonna assume the data is correct. Now we're gonna think about the recommendations being made. And the feedback came back, actually, Ben, this is pretty accurate. We may have issues here and here, but overall the trajectory is accurate. We have to underinvest in those states. We have to overinvest in those states. We have to find influencers who can help us get into those states. We have to increase the number of reps going to those events. We have to decrease the number of reps going to those events. And the team is now acting on 5 or 7 different follow-ups from the report. So not only they got bought into the AI, They had a chance to realize the data is never going to be perfect. You have to make decisions with 70% of the data, but they got to implement the change. And I'm hopeful, I'm really hopeful that maybe over the weekend one of them is going to start doing what I do with their own set of data. That would be a great outcome for us.
It sounds like you do a really good job of like with the let it run motto and just allowing your team to feel safe to make decisions because I think that is where people get stuck is it's not like they don't wanna try things, but often it's this feeling like they need permission to make a potential mistake or to try something new. And I think it's really cool that you're incentivizing and giving that reins to—
it's possible this stems from being a chief marketing officer, because if you think about a CMO, you experimenting all day and you make a lot of mistakes. We don't talk about mistakes on Adweek and AdAge, but those mistakes have been made as we know. Right? A performance marketer is gonna make 20 mistakes a day, you know, and maybe one will come up with one blockbuster every week in terms of marketing performance. So maybe it's something that I inherited from the CMO days that I brought back into the CEO organization. Because yes, if you hire an accountant into a CEO position, and there's nothing wrong with that, but the accountant will be looking at something very different, very detailed, very accurate, very precise. I don't have the luxury of doing that right now. We are doubling revenue, if not tripling revenue every year. I cannot go and pretend that everything has to be 100% accurate and precise because if I do this and I wait for the data to be correct before making a decision, I would never get the data and I would never make a decision. Mm.
So true.
Neither would my team.
Yeah, that's so true. Well, this has been amazing and there's, I have so many questions on here that I didn't even get to yet, but Just to be mindful of our time here, we'll go ahead and wrap up with what are you most excited about both personally and professionally in the next 6 months?
One thing I'm excited about is a transition that we're making at Pearl from being a, you know, Series B to maybe what we call a growth company. What that means is all of a sudden You know, Series A, a Series A company where I started, you have a product market fit, you have a bit of revenue coming in, you know, you raise money during your Series B to prove the model and you scaling. And that's what we're doing right now. This is known as when you have found product market fit, you move to sales market fit. And that's what a Series B company is going to do. You scaling your entire sales organization, your processes, your customer success team. What I'm excited about is we've done this successfully. I'm excited to take it to the next level where we become way more efficient with the resources that we have. We become way more strategic, right? So for example, when it comes to geographical coverage in the US, as I mentioned earlier, we're gonna make sure that every state is being attacked in a similar manner. Then that way we can maximize the number of customers we have across all those different states. It's shifting from experimentation to optimization, I like. You know, you start looking about a country mix. Should we go to Japan? Should we go to Singapore? And you start applying much more disciplined framework to go make those decisions. For example, and I'll stop here, a big change for us this year is we're implementing OKR, Objective Key Result methodology. This is incredibly time-consuming and very hard to do. And for the first time in history, I'm able to do this because I can partner with the new CTO, CPO, Chief Product Officer, with an exact same page. We need something that's very strategic at the very highest level with company North Star metrics that cascade down to company key performance indicators and go all the way down to individual bonus plans. Believe it or not, I'm actually excited to roll this out. It sounds very nerdy in some way, but I'm excited to roll this out because I feel like we're gonna do a big favor to every employee in this company. We're gonna tell you what is strategic and what is not. We're gonna provide some guidance where your time should be spent. And we're going to compensate you on you being able to focus on this area, are going to move the needle for us as a company. So the big shift for us next year is the implementation of OKRs, and you can, maybe we can talk again in one year and see how we did.
I love that. The book Scalable by Ryan Dyson, it's a little bit different than EOS, but I've gone through half of the book and it's very simple, However, it, it could be really supportive to you, uh, as you're starting to roll out the OKRs because he's got this like flowchart process using sticky notes and being able to pull out the absolute highest value things in the company and what actually should be prioritized and how to create like the SOPs and the systems in a more streamlined way without, without people having to go find them. So just throwing that out as a book recommendation potentially for you and anyone else that's listening. And it is my current read and I've been learning a big—
Well, the holidays are around the corner, so here we go.
Yeah, add it to your wishlist. Add it to your wishlist or yeah, your Christmas downtime on the couch book. Well, this has been amazing, Ben. Thank you so much for your time and best wishes with everything you guys are doing at Perla AI.
Thank you so much, Sabrina. I was so excited to be here.
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