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A
Two years ago, when I got a text message from Ophi, who's now my CEO and asked me to jump Pearl 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's book and I read it, probably memorize, you know, some of the key takeaways of the book. For example, this Idea that the CEO is going to 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 go and figure the financial reporting or go and figure out the company culture and you have to go and take those balls and just come up with something that is beneficial for the CEO and the company.
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Welcome to the Second in Command podcast produced by the COO alliance and brought to you by its founder, Cameron Herold. In the second in command podcast, we talk to top COOs who share the insights, strategies and tactics that made them the chief behind the chief. And now here's your co host, former COO of a multi eight figure remote company and alumni member of the COO Alliance, Savannah brewer. Ben is the Chief Operating Officer at Pro 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 CEO or an aspiring second in command, this episode is for you. Let's dive in. We are live with Ben. Welcome to the show.
A
Thank you, Sibana. Thank you for having me. I'm excited to be here.
B
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?
A
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 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 algorithm and we can scan dental X rays at scale, find pathologies, let's say carry 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 two years ago as Chief Operating Officer. All 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.
B
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.
A
So the founder of Perl is also the founder of the company I mentioned previously called Gumgum or I was at Gum Gum, which is a large adtech 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 Ofer Tanz, 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 as Chief Marketing Officer, Chief Growth Officer and now Chief Operating Officer. So I like to go around through different executive positions.
B
Did you get hired originally for the CEO position or cmo?
A
I was hired for the CEO position back then. That was two years ago. The company had found product market fit. The company had traction with dentists in the US and beyond. And I got this, not even a phone call, I got a text message from Ophir saying hey, we need 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 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 CEO before, I would be able to transfer some of the skills I had the 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 in our 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 going to be my dumpster. I'm going to dump everything I can into that bucket. You're going to 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 jumped in.
B
What were the skills that transferred easily versus the ones that were really difficult?
A
I start with the easy ones in general. I think if you're a leader, if you are putting at a C level in a mid sized to large company, you have a very large team. Typically I had 1 in 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 cost 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 a talent that Athea had, was very easy to apply to the new coo. Now CEO takes you to one or two levels deeper because not only you have to understand your teams, we 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 collections in terms of, you know, collecting money from customers, let's say in terms of HR principles, you want to 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 one to two level 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 dot across the organization.
B
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?
A
Yeah, I was lucky that I knew I'd say a third of the business. So a third of the company will 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 still learning in terms of the third element of the company I still have to learn will be what we call gna, 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 how to 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 CBSB's organization. Consider companies that have product market feed that scaling but not quite profitable yet you learn that the financial 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 ahead of finance. For example, you learn to understand the differences 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 space and now able to sit down with the CFO and have a conversation about, let's say 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, we represent companies when it comes to equity investor relations. And then you got commercial lawyers, commercial lawyers as dedicated to special deals and contract here 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 would have a potential impact on department B. That is really the role of the CEO. I'll give you an example. If you decide to work with a customer success team and change their goal from, let's say NPS NET promoter score to let's say a goal that is more focused on retention, then when you make that change, you also have to understand the change is going to 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 going to deliver to the customer. So you learn to connect the dots.
B
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 want to make big mistakes. How do you ensure that you are able to connect all the dots without getting sucked in?
A
It depends on the stage of the company, I guess. When, when I was hiring to Perl, 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 that has, let's say I think we had 40 employees back then, four, zero. You are the GNA 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 six months at Pearl. I was by myself. And a joke I like to tell the board, I'm gna. I'm the only cost you're ever going to pay, at least this year for gna and you learn to do things by yourself. You learn to produce financial reports. You learn to develop a 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 consult because you're very cost centered then. So you learn to do several things, but quickly you realize I'm not that great at going that deep in terms of finance or accounting for all questions. And then you start bringing some experts. So I'll hire ahead of finance. Hired a head of hr. It was actually here, but we positioned someone as a head of operations. So I think the answer to your question, when you invest more 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 now 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 going to 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 sometime, you know, outside agencies and partners that we have.
B
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's book and we were talking about how there's very few resources for COOs and sometimes 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 Perl AI, that would feel very overwhelming to me because I don't consider myself to be great with financials. What was your process for getting outside information or was it just asking those questions or what was that process like?
A
Two years ago when I got a text message from Ophi who's now my CEO and asked me to jumper 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's book and I read it, probably memorized some of the key takeaways of the book. For example, this Idea that the CEO is going to 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 go and figure the financial reporting or go and figure out the company culture and you have to go and take those balls and just come up with something that is beneficial for the CEO and the company. The other thing I read and studied is a have a business review article called CEO the second in command and that may have been the inspiration of Cameron or vice versa. Maybe the article is inspired by Cameron. Who knows who comes first? This article, if you go to Google and look for HBR SEO Second of Command is I think six or seven pages very dense and detailed article that really trying to figure out what a different type of CEOs and I think the challenge was CEO. All the different types of you have the go to market CEO, someone like me who initially comes from marketing and sales background and whose primary skill is going to be either 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 six or seven different archetypes of CEOs. The first thing I did was to write the article understand where do I fall under 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 is amazing with investor relations, amazing with business development. But there's a number of things like running bonus plans, running a customer success team, understanding the company culture and coming up with operating principle 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 a 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 bounce plans in this company. I had to build them all. But then I realized two 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, upsell and cross sell our customers. So I'm moving back into the sort of a CMO mindset. 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 GNA 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 going to add some value and try to specialize in this area.
B
What would you say are the key things from being a CMO that you think every CEO, 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 team or like leading team like you were doing?
A
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 going to have to work with your media relations team, you're going to work with your media relations agency, you're going to have to work with your marketing automation team, you're going to have to work with your creative team, you're going to 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 is doing that on steroids. If you launch a new, let's say company playbook, 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 work with the product team and engineering team. I think that's a big transferable skill 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 up 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, as something I can do that very effectively. And sometime being creative does not mean, you know, something incredibly exciting and flashy. You could have a set of issue. 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 collection some customers and you realize you are building the customer before the customer get 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 one week, two weeks. But that allows you to build a customer on the spot. Has to wait for two weeks to build a. 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 but 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 their people out. This is practical operator level work, not theory. Check them out. Proactive always wins over reactive. Details are@coo alliance.com forward/partners that COO alliance.com forward slash partners and go check out Next Level Growth foreign. 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.
B
I love that. 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?
A
Yes. I told my team that some of my marketing mojo was, you know, I want to test out. My marketing mojo is 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 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 interview with executive, 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 going to be shipped in about one week. And something that I think if you're a new employee coming to the new organization, you're going to be much more excited to read than a bunch of blue links.
B
That's so cool. That actually reminds me of something that we did when we were scaling really quickly. We were like, how do we transfer 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 my 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?
A
Yeah, I want to go back to a point that you made, I think is very important to me. One of the cardinal scenes of being a CEO is you kind of have to repeat yourself. Regularly remind 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 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 the existing materials being available to them and make them stronger over time. So two companies ago, we had this marketing playbook. Welcome to Gumgum. 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, denim ones can be intimidating for a lot of people. You don't show what you're going to 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 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 three words on the wall that no one's going to read. And we said no, I think will 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 quickly 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 I mean is that if we're judging you through a quarterly check in as an employee or if you're assessing your performance during the annual review, we're going to 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 going to 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 seed 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 and 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 still cannot find it because documents are all over the place, different formats. And what we did is we use a 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 not 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, two 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, 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.
B
What tool is that that you mentioned?
A
The one tool I'm using is Anthropic Cloud, 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 cloud, by the way. I have no skin and 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 also found the AI to be very honest. Ben, I don't have an answer to that question. I'm going to 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 an assistant that is sitting near you, available 247 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 found it incredibly effective and very productive.
B
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?
A
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 motor, a tagline we adopted for our customer success team about six months ago. Six months ago we were going incredibly fast as a company and when you go really fast, sometimes you see how it churned, how it turned means some of the customers live faster than you like. So we had this instance where we're launching a new product that probably was not as funnel as it should be. And we saw a number of customers leaving us. We decided to organize daily standups and weekly work session with the customer success team. Was 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 sometime 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, from implementing those ideas? He said, nothing really. And I realized, 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 be frozen by indecision. So why don't you wrong. And if you go a little too far or a little too fast, I'll catch you and bring you back. And that's okay. I will never blame you from 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 have been running ever since. Now, I'm using this tagline for other teams as well. Like, 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 onboarder who's onboarding a doctor, as we do daily, they may have six to eight 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 go back to AI for a second, I just want to illustrate a point I made about the use of AI. To be very, very clear, of course we're not going to 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 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 team to put together a very long list of details that relate to each 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 cloud for a weekend. We went back and forth a couple of times. I had to make some refinements because I obviously got it wrong in the first place and then got it right. And I came up with a 16 page reports that's telling me you are overrepresented in number of states, you are underrepresented number of states. If you do those five things next year you would drive ROI by 25%. This is something that would have taken a very big brain maybe a week or two to produce. The AI did this over the weekend and mostly it 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.
B
Love that example that you just gave. Have you guys already rolled that out or what has shifted since then?
A
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 a head of marketing, head of events, head of sales, head of ops, about eight people. I said, we've got 90 minutes. You have a 60 page report to read, you've got 30 minutes it was written by the AI and I was very transparent. This is how I went about this. This is an AI produced report. You're going to read for 30 minutes. We turn off zoom, you're going to come back in 30 minutes and we're going to discuss the report. They came back 30 minutes later. Okay, where's the data? And you know, usually what people do in large organization is question the data. And I made a variable statement, Nope, we're not going to do that today. What we're 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. Stop naming 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 going to go make decisions. And then the conversation shifted to okay, we're going to assume the data is correct. Now we're going to think about the recommendations being made. And the feedback came back actually ban. 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 over invest in those states, we have to find influencers who can help us get into the 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 five or seven different follow up 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 decision with 70% of 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.
B
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 want to 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 your.
A
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. We can add it, but those mistakes have been made, as we know. Right. A performance marketer is going to 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 inhibited from the CMO days that I brought back into the CEO organization. Because, yes, if you hire a 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 tripping 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 quiet before making a decision, I will never get the data and I would never make a decision.
B
So true.
A
Will my team.
B
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 six months?
A
One thing I'm excited about is a transition that we're making at Perth from being a, you know, series B to maybe what we call a growth company. What I mean is all of a sudden a series A company, where I started, you have a product market fit. You have been around, you coming in, you raise money, doing a series B to prove the model and you're 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 CSV company is going to do. You're 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 more strategic. Right. So, for example, when it comes to geographical coverage in the US as I mentioned earlier, we're going to 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 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 this year 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 a 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. But even now I'm actually excited they release it. Sounds very nerdy in some way, but I'm excited to roll this out because I feel like we're going to do a big favor to every employer in this company. We're going to tell you what is strategic and what is not. We're going to provide for your time should be spent and we're going to compensate you on you being able to focus on this area. Going to move the needle force of the company. So the big shift for us next year is the implementation of okls and you can maybe we can talk it in one year and see how we did.
B
I love that the book Scalable by Ryan Deiss. It's a little bit different than eos, but I've gone through half of the book and it's very simple. However, it could be really supportive to you as you're starting to roll out the okrs because he's got this 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 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 is my current
A
read and I've been learning the holidays around the corner. So here we go.
B
Yeah. Add it to your wish list. Add it to your wish list 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 Pearl AI.
A
Thank you so much Sivana. I was so excited to be here.
B
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Podcast Summary:
Second in Command: The Chief Behind the Chief with Cameron Herold
Ep. 569 – Pearl COO Ben Plomion – How Top COOs Crush Chaos and Build Pro Teams
Date: April 9, 2026
Episode Overview
This episode features Ben Plomion, COO of Pearl AI, in conversation with host Savannah Brewer. The discussion centers on the unique challenges—and crucial strategies—of transitioning into the COO seat, developing cross-functional skills, scaling teams with operating principles instead of values, and leveraging AI to drive operational and cultural excellence. Ben shares actionable insights and real-life stories from rapidly scaling Pearl AI, including his principles of empowering teams and his “Let them run” operating motto.
Quote:
“I got this text message from Ofer saying hey, we need to scale… I need someone who can organize the company. For me, it was a no brainer.”
—Ben Plomion (04:40)
Quote:
“The COO by definition is the ultimate cross-functional role… you have to understand enough to ask the right question across every single team.”
—Ben Plomion (07:32)
Quote:
“It is very easy as a COO to get lost in the details… but your perspective is to understand how [departments] interact and make decisions, connecting the dots.”
—Ben Plomion (10:46)
Quote:
“My advice for any COO… there’s different flavors of COO. Try to find where you’re going to add value and specialize.”
—Ben Plomion (19:34)
Quote:
“We moved away from values and adopted operating principles… values had a negative connotation. Three words on the wall no one reads.”
—Ben Plomion (28:05)
Notable Culture Insights:
Quote:
“Let them run is a motto we adopted… I’d rather have you think about solutions, implement them, than be frozen by indecision.”
—Ben Plomion (33:38)
Quote:
“If you freeze by indecision, then I have a bigger issue here. Let them run, and if they make mistakes… that’s okay.”
—Ben Plomion (35:20)
Quote:
“I’m excited to roll this out because we’re going to do a big favor to every employee… tell you what’s strategic and compensate you for moving the needle.”
—Ben Plomion (44:16)
| Timestamp | Speaker | Quote | |-----------|---------|-------| | 04:40 | Ben | “I got this text message from Ofer saying hey, we need to scale… I need someone who can organize the company. For me, it was a no brainer.” | | 07:32 | Ben | “The COO by definition is the ultimate cross-functional role… you have to understand enough to ask the right question…” | | 10:46 | Ben | “It is very easy as a COO to get lost in the details… but your perspective is to understand how [departments] interact and make decisions, connecting the dots.” | | 19:34 | Ben | “My advice for any COO… there’s different flavors of COO. Try to find where you’re going to add value and specialize.” | | 28:05 | Ben | “We moved away from values and adopted operating principles… values had a negative connotation. Three words on the wall no one reads.” | | 33:38 | Ben | “Let them run is a motto we adopted… I’d rather have you think about solutions, implement them, than be frozen by indecision.” | | 35:20 | Ben | “If you freeze by indecision, then I have a bigger issue here. Let them run, and if they make mistakes… that’s okay.” | | 44:16 | Ben | “I’m excited to roll this out because we’re going to do a big favor to every employee… tell you what’s strategic and compensate you for moving the needle.” |
For more insights from leading COOs and to explore professional resources, visit COOAlliance.com.