Ep. 123 – Liveintent Chief Operating Officer, Brett Pinegar

Email marketing is a tried and tested digital strategy to generate leads, and it will stay in the business scene for a long time. It is up to the marketers to come up with fresh ways to make it effective despite the changing trends. Cameron Herold sits down with Brett Pinegar of Liveintent to discuss how they work with this particular strategy for their clients, specifically through the SAAS business model. Brett also shares his experiences as one of the company’s leaders, detailing how he transitioned from being the CEO of three companies to becoming Liveintent’s COO. He goes deep on how he works closely with his CEO and what it takes for such a leader to step up, especially in the most challenging times.


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Brett Pinegar is the Chief Operating Officer and CFO at LiveIntent and has overall responsibility for key operational teams within the company and finance. Brett’s focus is on helping his team operate with excellence as they help their customers win using the power of email as a people-verified media channel. Brett brings over 25 years of executive leadership from serving as CEO to three separate technology companies, including Akopia, an open-source eCommerce platform that was acquired by Red Hat Software. Brett has also advised and coached hundreds of technology executives. He is a passionate trail runner and a student of leadership. Brett, welcome to the show.

It’s great to be here.

You’re living in a good place to do trail running, living in Utah.

It’s one of my great passions. It’s something I’ve fallen into relatively later in life. I used to do a lot of road running and I enjoyed that. To be able to combine my love for running with getting outside and truly being in the mountains on the trails, being away from cars, sometimes, frankly, being away from people, it’s a great thing.

It’s pretty awesome. I split my time between Vancouver, British Columbia, and then down in Scottsdale, Arizona. I used to do a lot of trail running up here in BC. Any of the hikes I was on, I would run the flat sections. Anybody I was hiking with was like, “What’s the rush?” I’m like, “There’s no rush. It’s flat, we might as well run this damn thing. Why am I going to walk along a flat trail?”

One of the great secrets of trail running is you walk up and you run down. If the trails get too steep, there’s no way you’re going to be able to run them. This notion of going on a trail run for me is a combination of walking and running. That variety also is a part of what’s a lot of fun about the experience.

You’re right about getting away from all the traffic and the cars, too. I did my only marathon years ago. Unfortunately, that’ll be my last run because I got my left hip replaced due to years of running and competitive ski racing. It did its toll and I ended up needing to get my left hip replaced. The recovery was good. I did my first hike and did an 11-kilometer mountain hike and it was awesome. At least I can keep hiking but I won’t be doing any pounding on it anymore.

Eleven K is not bad. No complaints.

It was good. It was great. It’s good to be out with my kid, too. Tell us about LiveIntent so we know the background of the business. I want to dive into your role there.

LiveIntent is the leader in real-time ads delivered in email. If you receive an email newsletter from the likes of New York Times or any other company, Groupon, for example, in that newsletter, you’ll likely receive an ad. That ad is delivered dynamically by LiveIntent. We connect publishers, advertisers, provide the technology and the infrastructure so that advertisers can deliver the right message at the right time to the publishing audience, to the likes of New York Times, and so forth. We also have taken that business and grow it into an identity business. A business where we’re able to help not just ourselves connect brands with people in email but also to help other companies do what we’re doing an email across the web.

You’re working on a consulting arm of some of these companies as well or as a SaaS model?

We provide SaaS-based data. We have a SaaS model where we deliver data solutions to other media companies, other ad tech companies that enable them to connect their advertisers and their publishers better together. As you may know, cookies are an important part of how you connect online. Cookies don’t work like they used to work. Our solution doesn’t require third party cookies and it enables people using first-party cookies, which are still valid and important in nowadays ecosystem, to be able to connect using that first-party data, using what we’ll call a hashed email address. These are some of the nuances of an ad tech experience.  We’re active in email and we see email everywhere, we don’t see the actual email address that’s considered personal information but we see a hashed version of that. That becomes a way in which we can connect the advertiser, the publisher, and the individual with the right ad at the right time, and the right environment.

Who do you sell through? Do you sell directly to these companies? Do you sell through channels, through ad agencies as well?

We sell direct. We’ve got direct relationships with all of our publishing partners. We also sell direct to advertisers and also use third-party DSPs where agencies and other advertising conglomerates tend to play.

It’s a cool model. Talk about the business itself and the size of the company, so we understand the scope of the operations.

The company is based in New York City. We have about 180 employees. Our office is in New York, along with offices in Chicago, Berlin, and Copenhagen. A lot of our development occurs in Europe where we’ve got a strong, technical talent base group of data scientists that are second to none. When we combine their expertise in using data effectively with the access, we have to the media market in the US, it’s been a great success.

SIC 123 | Email Marketing

Email Marketing: Offices play an essential role in running a business and will continue to be in the future.


Now that we’re in a COVID world, our New York office is certainly there but no one’s working in it. We’re all working remotely. We have people spreading across the United States as they’ve tried to find the place that makes it easiest for them to work. That’s been a fun part of our adaption to this COVID world is to be able to be a little more flexible in terms of how we work with our teams. The remarkable thing as we’ve gone through this horrific pandemic is to see the resilience of the team and to see the resilience of our offering in the marketplace. Thankfully, we’ve been able to see real success, real strength in our model, and our success.

You will continue to see it, too. It’s funny to think about the empty office spaces. I remember walking to school years ago and there was this old couple that lived down the street on the way to the school. They had this kid’s fort in their backyard, up in a tree, a little tree house and it had been empty for years because their kids have grown up and left. They didn’t ever take this tree fort down. I remember seeing this lonely, empty tree fort and I think of all the empty offices that are out there now that are sitting there.

It is. It’s going to be an interesting thing to see how the whole commercial real estate market plays out.

Do you think you’ll go back to a location-based business at all? Will you continue to be remote way more than you might have been before?

I certainly think we’ll be more remote than we were before. I don’t think we’re going to drop the office. Offices play an important role and will continue to play an important role in future business. We’ll use offices more relevantly. I’m not sure we’ll need an office as big as the office we’ve got. I’m not sure that we’ll have everyone come into the office as often as we did. Those are things we’re actively evaluating now. We’ve got a great team of people. They’re looking at all the issues. There are a series of important factors that we’ve been able to prove out that give us great hope that a hybrid model will be best for us and potentially many other organizations but certainly for us.

I’ve coached a couple of companies in the technology ad space and one is called Acceleration Partners, a CEO named Bob Glazer, and they’re completely remote but 150 employees. They’ve never had an office and they do all the affiliate marketing for brands like Uber and Apple and Target. They’ve been able to run this good business completely remote. No one’s ever had an office. Another one out in New York called Elite SEM, which is now called Tinuiti. They were digital, all in offices, and then had to split and go remote. They’re thinking the same thing, do they go hybrid? What are you looking at? How do you decide?

Let me give you a little more background. Prior to being at LiveIntent, I was the CEO of a company called WealthCounsel which is a software services-based business serving the needs of estate planning attorneys. At WealthCounsel, we were almost entirely virtual when I joined as CEO. Over a period of time, we went from a purely virtual model to a hybrid model where still about 70% of our workforce was remote. We brought key members of our development team and key members of our sales team into an office and we found that hybrid model worked well. There was a certain collaboration, especially in the throes of a development team where the team is working closely together. That worked well for us in an office environment.

The sales team as well, there’s a certain camaraderie, a certain talk back and forth that occurs that is almost a smack talk, if you will, of the room that keeps people going and gets people motivated to do their best work. That is an important part of a great sales culture. At LiveIntent, we have proven that a sales team can work effectively, entirely remote. That’s been an important improvement. Based on both of those experiences, there is a real need for a combination. For most businesses, having an office presence is important. Having an environment where people can come together and get connected is important. Also, the ability to then benefit from a much broader recruiting pool, from a much more diverse talent base, is also equally important.

One of the challenges with working remotely is you have to consider some of the issues related to what I call state tax nexus. When somebody works remotely, another state in which you need to be filing reports and things. There are real challenges that you need to consider when you’re going remote to understand that it’s not just, “Let’s do it. Let’s make it happen.” There are state filing requirements that you need to consider as well.

It’ll be interesting to see how the states try to clean that up or if they clear that up or if it is going to become a regulatory hurdle for us. Tell us about your transition into the company. You played a CEO role a few times before coming in as a COO at LiveIntent. Why did you make that transition into this second in command role? What was that transition like for you?

I’ve been CEO of three different organizations, the last one was WealthCounsel, the first one was Akopia, and the middle one was called Willowstick Technologies. They’re all different organizations. In between, when I would do that work as a CEO, I often would do consulting work, advisory work to companies. I had a lot of fun meeting organizations. One of the companies I met during that time was LiveIntent. Matt Kaiser, who’s our CEO, and I go back years when I first did some consulting for him at a company he was the prior head of. For me, it was much more about potentially working with Matt than it was about me taking on a particular role.

Having been the CEO of three organizations, what I’ve realized is, at some level, there’s something important about being CEO and something that’s also challenging about being a CEO. There’s a certain mantle that you wear as a CEO that is burdensome and heavy and lonely if you will. For me, to be able to help a friend, to be a part of a team, and not to carry that mantle was appealing to me. When I left WealthCounsel, I said, “I’m done being CEO. I’ve done it. I’ve done all that I wanted to do. I’m going to continue to do some consulting, some coaching and some other things.” The call came and the reality is it was something that I would love to do, which is to be able to support, help, encourage, foster, advice, but not have to be that CEO. For me, it’s a luxury to be able to serve in this capacity.

Tell us about what that mantle is that you’re wearing as a CEO or what that burden is. You’re right and a lot of the COOs know that it’s different but they haven’t necessarily experienced it firsthand. Can you walk us through some of the specific things that maybe are different or tough for the CEO so that as COOs, as second in commands, we know how to support them better?

Thank you. I love to be able to dig in. First of all, the most important part of the mantle is the sense that, “If it is to be, it is up to me.” It is on your shoulders. There is this notion that, there are other people supporting you. There are other people that are doing great work that are central to your success. There is something uniquely heavy about saying, “The company is on my shoulders. I report to the Board of Directors. They look to me as the one person who is solely and completely responsible. If there’s a problem in the organization, at some level, it’s my problem.” I can’t say, “That’s not my responsibility. That’s not my issue.” All issues, all responsibilities eventually flow to the CEO. As a COO, I can say that not every responsibility flows to me. That would be one major distinction.

When you think about the CEO, there is often an element of a founder in that CEO’s perspective. If you’re a founder CEO, you’ve created this company, you’ve grown it, it’s yours and you’re deeply passionate about it. If you’re a COO and you’re not with that founder, meaning you didn’t cofound the organization, you ought to bring a different perspective. You don’t bring quite the same passion, maybe, or that quite the same ownership that the founder or CEO feels. To me, those two things are critical differences between many CEOs and many COOs in organizations.

What ties in nicely with both of those as well, one on the mental state of the CEO is it’s a lonely position because they can’t tell the board everything. They can’t tell the board that they’re scared or worried or fearful. They need to tell most of the truth. Otherwise, the board’s going to be scared shitless. They can’t go down to the team and go, “I don’t know what I’m doing. This is the biggest thing I’ve ever done. I don’t fucking know this. I’m worried.” They need to tell you but they can’t tell everybody else. That’s why I love the CEOs to get involved with YPO and become a YPO member and get into mastermind groups for them because they need a place to talk to their peer group.

SIC 123 | Email Marketing

Email Marketing: If you’re a COO who did not work with the CEO from the start of the business, you could bring a different perspective on running things.


The second thing, especially with the entrepreneurial CEOs, this is the biggest thing they’ve ever done in their life. Every day, the company got bigger than it’s ever been and they don’t know what they’re doing. I remember meeting with the CEO of Sprint in his office, Marcelo, and he goes, “When are people not going to be the problem?” I’m like, “You’re the 82nd largest company in the US and you’re still trying to figure this out? It never gets easier for them.”

This is an art. How do you balance out when the CEO is doing something wrong or when you disagree with them? How do you bring your point across and tell them what you think? How do you show them their blind spots without getting their back up against the wall?

Having been in that seat, it’s easier to do now that I’m not in that seat. First of all, to acknowledge the fact that the world is on their shoulders, at least the company is on their shoulders and that you’re aware of the challenges that they’re facing. It depends on understanding the person. When it comes right down to it, we are people. Whether you’re the CEO, the COO, the CFO, a lead software developer, a junior level salesperson, we are all people. The sooner we can all come to terms with that, the better.

As a CEO, if I look at you as being somehow a form of deity, something special or different, I might act differently and/or not give the same level of feedback if I saw you as another human being and trying to do and be their best. For me, giving advice to Matt and to CEOs, in general, is all about understanding them and understanding what makes them tick. I believe deeply in the use of personality profiles and in trying to understand the human being. Using that information, you’re much better positioned to be able to guide the conversation then.

For example, I know that Matt is very visionary and has incredible ideas that are at the forefront of the industry and are critical to our success. Not every one of his ideas would be right. For me, it’s not about saying, “Matt, it’s not about every idea but there are some things we need to look at.” Those conversations occur in private. They occur at a time when I know he’s going to be open to listening, he’s not super busy, or we’ve at least created enough time where he can slow down and take a moment. It often comes with me being prepared with data to support my viewpoints. It’s super easy to say that we disagree. It’s much harder to say, “Here’s why we disagree, and here’s the data to support a different point of view.”

I often tend to not make it about me as a human being, too. It would be more about the idea. Matt has ideas. I have ideas. Let’s talk about the ideas versus let’s talk about us disagreeing. Those two things have gone a long way towards making a difference. I’m also aware that sometimes the different forms of communication make a bigger difference. Sometimes it needs to be written, in person, charts and graphs, a good story. Picking your analogies, picking your stories, picking the data is all about that process. To me, it is this notion of being able to hear and understand where they’re coming from. Make sure they understand that you understand where they’re coming from and then you can have a conversation. “People don’t care how much you know until they know how much you care.” That’s at the basis of this whole notion.

Were you and Matt friends before you joined this organization?

We were. Maybe not friends is the best way to describe it but we work together. When he was at a prior company, I came in and did some consulting work for him. We developed a deep, personal relationship in the sense that he trusted me and I trusted him. We kept talking and I became his coach over a period of time and began to give him some advice there. One of the things that’s interesting about our relationship is we’re different people, have different perspectives, have different upbringings. We’re not two peas in a pod if you will. We look at the world quite differently. A great key to our success is that we see the world differently and we’re able to respect it. We don’t see things in quite the same way.

It’s powerful and it’s also complicated at times, too. You mentioned personality profiles, which ones do you like and how do you use them?

We use the Predictive Index at LiveIntent. I’ve used Birkman prior. I’ve used Human Factors and the Acumen Profile. I’ve used a profile called Taze, which was originally used with the Navy SEALs. They’re all different. There’s Myers-Briggs and things like that, that are more mainstream. The most important thing to remember is one view of how the person sees themselves. Almost all personality profiles, you administer them it’s not like how other people see you. There could be a 360 component to it. Much of it is, “How do I see myself based on the questions that are asked?” If you look at it like that, then you can say, “This is how Matt sees himself. This is how I see myself.”

Using the Predictive Index is a great one because it gives you these common terms to describe a typical personality profile and none of them are necessarily good or bad. They’re all different. For me, I’m a maverick as it relates to the Predictive Index, which is a combination of playing by the rules and breaking the rules all at the same time, thinking outside the box, lots of innovation, at the same time, still using process procedures to make things happen. Knowing that about me and knowing that Matt is much a visionary is helpful for us as we work together.

I’m still trying to find the box. You keep talking about getting outside of the box. I’m like, “Where is the box?”

There’s a funny story here. There’s a group called The Arbinger Institute and they wrote a book about the box and about getting outside the box. The funny thing about their box is whenever you think you’re outside the box, you’re in the box. The notion of being able to truly be outside the boxes is probably a figment of our imagination. Whether we’re in the box or we’re in the matrix, we’re in something, for sure.

There’s something there, for sure. Have you ever come across the Kolbe Profile? Kolbe is interesting as well because it teaches you how you start projects, how you initiate things, and there’s something there. The weird one that I’ve come across that I’m using inside the business world, this is going to sound hilarious, I love personality profiles for lots of different reasons, understanding the people and how to work with them, is the 5 Love Languages. When you think about it, the five love languages are words of affirmation, quality time, physical touch, gifts. That’s all people need to be appreciated, a tap from the back or a hug in the morning or lots of praise and you realize like, “Maybe they need time. Do you want to go for coffee?” You bring the love languages into work with your team and it’s crazy, the impact that starts to have. We’ve introduced that now.

I love that. One of the things that is most interesting about the Love Languages and applying that to work is we often tend to think that it’s inappropriate at work. Why would you ever be talking about this notion of close, intimate connection with another person? At some level, we spend more time with the people at work than we spend with any other group of people.

The intimate connection is the connection of humanity. It’s not like we’re going to have sex with each other.

SIC 123 | Email Marketing

Email Marketing: The notion of getting outside the box is probably a figment of the imagination. Everyone would be in some kind of a box, one way or another.


That’s exactly right but this form of connection, intimacy, if you think about it in an erotic way, that’s certainly not what we’re talking about. Thinking about it in terms of humanity connecting with each other, it’s critical. Empathy is the currency of intimacy. If we’re able to be empathetic, then that goes a long way. That comes back to what we talked about in terms of giving feedback. If you’re empathetic in your feedback versus saying, “This guy flipped the bozo bit,” it’s a whole different perspective in terms of how you will work to provide feedback and to interact.

Talk about that as it relates to your team and your direct reports, coaching, and leading people. How do you lead your team? How do you coach them?

I’m very much a leader of people versus a leader of projects versus a leader of goals and objectives. All those things are important but it starts and ends with people. I’m a long time in coming to that conclusion. Early on in my career, it was all about delivering results, it was all about crossing things off the list, it was all about achieving. What I realized is that if you focus on achievement, you often don’t pay close enough attention to the things that matter a lot more which, to me, were relationships. Relationships are central because success is ephemeral. It comes and in it goes. The relationships you have with people stand the test of time. I’ve come to the belief that it’s one of the few things you can keep with you are these relationships.

For me, as I’ve evolved as a leader, I’ve worked much more diligently to be understanding of the team and to help them thrive, to grow and evolve. I would call myself a coach more than anything else. As a leader, I’m helping individuals to establish what they want to accomplish. I’m giving them feedback in ways that will help them grow and develop. I want them to, eventually, at some point, take my job or to be able to take their job to the next level certainly. By having that mentality, it changes how I approach leadership, which is to be people first, which is to ensure that I understand where they want to go.

If I can help them get where they want to go, they will be much happier and more fulfilled at work if we’re able to make that happen. Together, we can then accomplish great things. If where they want to go isn’t where we’re going, it’s better to know that and then to help them find where they want to go and make that happen as well. All in, it’s understanding that people’s passions are pretty much the strongest thing there is. If you’re able to connect somebody’s passion to the work that needs to be done, then you’ll see great success.

That’s pretty insightful as well. Understand that if somebody’s path isn’t necessarily staying in our company and it’s to go somewhere else, our job is to help them go do that. It’s no different than growing our kids. It would be nice to have our kids live at home with us forever but at some point, they got to move out.

There comes a point.

I’m like, “Trust me, you’re moving out soon. Come back and visit often.” It would be nice to be able to have them around. My job is to get them out of the house. My job is to grow them into these independent kids.

Think about how different that is at work. Often, we think, “I need to keep this person where they are so they can help us be successful.” When you flip that on its head, it changes the way you become. You need to backfill a fair amount. You need to help grow those lower ranks so that you can continue to have a pipeline of people growing and developing through an organization. You create this newness and yet this path of excellence where people can grow, develop, move on, or take the next step.

The employees see that you care about them. When you’re focused on them and their growth for their own purposes, they’re going to go through brick walls for you to build the company. Do you have one-on-one meetings with your team?

I do, and group meetings. We both meet one-on-one every week and then as a group every week.

I wrote a book called Meetings Suck to teach people how to run meetings and how to participate in them and what meetings you need to run. I’m curious, can you walk us through how you run your group meeting first and then how you run a one-on-one meeting?

Typically, a group meeting would start and end with something fun and humorous, a way to break the ice or an icebreaker. Maybe somebody will share a video. Maybe there’ll be a joke. Maybe what you did over the weekend or whatever. We’re doing more of that in our meetings because we don’t naturally do it around the water cooler because there is no water cooler. The actual substance of the meeting is to work back to what our OKRs are.

We’re an OKR-focused organization. We use objectives and key results to track both our goals and how we’re doing with respect to those goals. Each person has a set of OKRs that they’re then tracking to. They will talk about what they’re doing to achieve those goals over the past week. What are the roadblocks they’re facing? That’s where I step in and say, “What can I do to support that? What can others do? What do we need to do collectively to break down those barriers or obstacles?” We will end with a bigger, deeper discussion on 1 or 2 topics that’s relevant to the business. What’s the big issue we’re facing? What are some of the challenges that exist across the organization?

For example, during this moment of Black Lives Matter that we’ve been immersed in it. It’s been super powerful for us as an organization to be able to connect the dots better than we have had historically. We’ve talked a lot about that as a group. That’s been an example of one of these topics that formed the basis of important changes that we’ve taken on in the organization as it relates to diversity and inclusion and what we’re doing with respect to that. Start with something fun, OKRs in the middle, a big strategic topic at the end.

Does that run for an hour?

SIC 123 | Email Marketing

Email Marketing: You will find great success by learning to connect with somebody else’s passion.


At the most. If we can keep it to 45 minutes, great. There’s no need to take any more time than it certainly takes.

I always say it’s like a quickie. You can get it done in less time if you need to.

I love the Google thing where you can set your meeting stand at fifteen minutes to the hour so that you don’t have to then have everything go up to the final moment.

I finish everything five minutes early. If I schedule it for twenty minutes, we finish in fifteen. If I scheduled for two hours, we finished at 1:55. That way, I have time to go down the hall and talk to my assistant and get a cup of coffee, sit down and start on time. Everything finished is five minutes early. I got anal-retentive about that. You’ve got a direct report. Give us a traditional, normal one-on-one.

It’s because we talked about the OKRs and the group meeting, we tend not to do that. It will be focused on a specific set of issues that they’ve learned about that I need to be aware of. It would be in the mode of, “What do you need to communicate to me that’s going on in your organization?” Maybe there’s somebody who’s getting ready to quit. Maybe there’s a need to make a change in a particular reporting structure as an example, and other issues like that. We’ll use a software program called 15Five, which is a way to collaborate.

I’m an advisor and an investor. Potentially, I was the original seed idea for that business with David Hassell years ago. At a Warren Buffett event, I told him about a 15Five program I used that I learned from Starbucks and he built a whole company around our discussion in a bar.

It’s phenomenal. We use that. We’ll do our one-on-one meetings right to that. Throughout the course of the week, they will then add things to their one-on-one. Often in one-on-ones, it’s like, “What are we going to talk about? What happened yesterday? What happened this morning?” Instead of what needs to occur. By putting things into the one-on-one, when they occur, then it’s easier in the moment of the meeting to have a true conversation about the real issues versus the last issue on the table.

What I love about the software is the employees take fifteen minutes to fill it out and it takes us five minutes to read it. It’s amazing the stuff that they’ll put in writing that they normally would either forget or wouldn’t necessarily say. It’s like texting somebody, you often have more courage to throw it out there than you would in real life. They write stuff down, like, “I’m pissed at so and so in this other departments.” It’s like, “I guess we have to talk about that now. I’m struggling with this.” It’s insightful and it’s a great tool for both people.

That would be the aspect of 15Five. For those who don’t know, it’s focused on giving feedback. At the end of every week, you’re able to say, “How are you doing? What’s going well? What’s going poorly?” That’s sort of thing. Independently, you’re on the one-on-one meeting. You are also able to connect it to OKRs, which is another way and which we’re using it. Between OKRs, the weekly check-in, and then the one-on-ones, it’s been a great tool for us.

You reminded me of somebody else who I had on the show, it was Matt MacInnis from a company called Rippling. He created something called The Operating Manual for Matt. We’re talking about how do we learn about our employees and support our employees and get to know them through personality profiles. He wrote a three-page bio about himself, about his idiosyncrasies, and what he’s like as a jerk, or what he’s like as a leader, or how he might micromanage at the wrong time, or how he shows up if he’s stressed. He gives that to every employee so they can learn about their boss before they have to start working with him. I’m like, “That’s awesome.”

You create authenticity, disclosure, and vulnerability. All of those things are critical. We often underestimate how distant we can be perceived as being from people that report to us. Whether you’re a CEO or COO, you can feel a long way away from a rank-and-file employee. Anything you can do to bridge that gap is important.

It’s like my ex-wife could certainly tell my girlfriend a lot about me. It’s a whole learning curve. How about staying on the same page with your CEO? How do you stay on the same page with their vision and how do you get him to stay on the same page with your plans? How do you guys keep in sync?

That’s a challenge for everybody because vision doesn’t necessarily play by plans. Sometimes it can come into an odd moment. It can come in the middle of the night. It can come as you’re getting ready to start something else. What we try and do is to create an environment where ideas are never off-limits. We are always saying, “What’s new? What are the opportunities we’re facing?” In many cases, we’ll be folded into the current set of plans or we’ll put them on a parking lot and make sure that we don’t forget about them. In the future, we’re able to move forward then.

We use a little sheet that says, “Here are our top priorities.” It’s separate from the OKRs because they tend to be a little more visionary, a little further out. These are the things that we’re not quite ready to operationalize fully but we need to test, we need to prove out, we need to iterate around. That’s where Matt is. That’s what he’s doing. As COO, what I’m doing is taking the stuff that is closer to getting ready for primetime and making sure that we’re able to operationalize that. We have this notion of operating with excellence. For me, that’s critical.

What we try and do is ensure that we’re operating with excellence around things that there’s some consistency with, a sales process, a process for supporting customers, a process for approving legal documents. We tend not to over process eyes or systematize things that are in that nascent stage of being proven out. Trying to create space for ideas to be free-flowing and we’re able to test them out in an iterative, entrepreneurial way. When they’re ready, bring them into the more highly operational parts of the business.

How do you decide when an idea or when a project gets green-lighted versus when it’s yellow light? It’s like, “We’re going to do it but not yet.” Red is like, “We’re never going to touch it.” What’s your system for that?

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Email Marketing: Bridging the gap between the CEO and COO, or the employees and their superiors, must never be underestimated.


We have a strategy. Our strategy is something we go back to all the time. It’s a way in which we’re ensuring we’ve got good OKRs. For us, it’s like, “Is this aligned with our strategy or not?” To me, a strategy is nothing more than the cumulative sum of things that you say yes to and you say no to that will lead you to the success, or to the outcome you’re looking for. If we want to go out and climb this mountain, what’s the trail we’re going to take to get there? Your strategy is the trail you’re going to take. As long as it fits within the context of how we go to market or which customer segments we’re focused on or what products we’ve got, it’s a lot easier.

As you start saying, “It’s a different business model. It’s a different group of customers or a different product. It’s going to require different capabilities.” You start saying, “That’s going to be harder to say yes to because we’re going to have to do something that is going to break what we’ve currently got. If we’re able to stick within that framework of the right product, the right customers, the right go-to-market model, the right business model, then it’s a lot easier.” We tend to use those terms to describe and to make decisions around. If one of those things is different, it’s the same product, it’s the same business model but a different group of customers, that’s an easier yes. If I say, “It’s a different product. It’s a different business model. It’s a different group of customers. It’s a different go-to-market.” We then say, “No. Never. Not for us.”

It sounds like your CEO is probably past the whole entrepreneurial seizure and the entrepreneurial ADD stage where everything’s a great idea and let’s do it now.

It’s important that we never truly get beyond those stages. Sometimes if you get too locked and loaded, you’ll miss something new, you’ll miss an opportunity. Matt is good at being able to stay entrepreneurial. At the same time, what we do is we bring those conversations back to reality. To me, it’s a mistake to be too locked in and not consider things that would be outside the box if you will, meaning outside those six different constructs. I do think that you evolve and you get more mature over time. We try hard to stay innovative. As Clayton Christensen talked about in his book, The Innovator’s Dilemma, you can’t get there with what got you here. You’re going to have to continue to reinvent yourself. If you don’t, you’re going to be in trouble.

A curious question on the business itself and your unique abilities, what parts of your business do you outsource?

There are certainly key development capabilities that are easier to outsource than to hire internally. We have a technology partner that we work closely with and that is an important part of our overall development structure. We have certain operational components, especially on the add operation side that are manual, that are labor-intensive. It’s easier to work with partners in different parts of the world to help make that happen. We use classic services, whether it be outsourced experts around privacy, security. We’re also looking at legal talent and accounting talent and all those things where you’re using outside resources that are integrated with us. In general, other than the tech and some of the operations, we built an organization that handles it from soup to nuts.

It’s good though because you are outsourcing some parts that some companies wouldn’t even think of outsourcing. Even when you said, “We’re outsourcing some of the operations,” some would be like, “Why would we ever do that?” Sometimes it’s hard for people to let go of some areas that’ll never be their unique ability. The more cycle time they spend on stuff they’re never going to be great at, they’re taking away the time from the stuff they could be world-class at.

We’ve learned that. You’ve got to be good at something. The difference between having strength and super strength is about 10X from my perspective, whether that’s you as a human being or you as a company. If I said that I can play the piano, it doesn’t mean I can play the piano. Somebody who can play the piano is maybe ten or even 100 times better than somebody who can play the piano. If you look at it from that perspective and think about that from a company perspective too, a great software developer is often 10 or 20 times more productive than a run-of-the-mill software developer. Find people that bring tremendous expertise, that’s what we did in Copenhagen. We acquired a company called Mojn back in 2015. Mojn brought these great data scientists to LiveIntent. We had started in New York, hired a few people and done some things. It could have been good. The fact that we went out there, we found an organization that was the right organization for us to acquire. At some level, it was an insourcing of an outsource model.

It makes sense. I have a couple of questions related to you and your growth. In terms of 10X-ing our own growth or 10X-ing ourselves, where have you worked on yourself over the years in terms of your skillset? Have you had areas that you’ve focused on more than others?

For me, there are two different ways of thinking about that. One is I need to get better at me. To me, that’s better understanding me, that’s understanding the way my mind works, what makes me tick, understanding my mental models, and understanding the experiences I’ve had that influenced the way I respond to things. Often, when I get strongly emotional, maybe I’m getting angry or disappointed or whatever the case may be I’ll be like, “What’s going on there?” For me, that gives me an opportunity to be introspective and say, “My world is causing me to react strongly to that situation.” As I get better at understanding that, I’m able to evolve and become more flexible as a human being. That would be one aspect of my growth and development.

From a skills and capabilities perspective, I am a lifelong learner. I’ve been reading, studying and growing at every possible moment. I see that as an important part of my success, whether it’s learning how to code as I did years ago. It’s where I started out. The first company that I started as a teenager was a software development organization where we were developing programs for local school districts on the Apple II Computer. This was a long time ago. I love that learning experience. Learning about economics in college to being able to learn much more about the world at large by reading voraciously biographies of the world and taking all that information to say, “What can I do to be better?”

A couple of key skills that have been very important to me, number one, is the ability to tell a great story. It informs my effectiveness. The ability to be able to listen carefully and to hear carefully what people are saying is another important skill. You cannot underestimate your need to be analytically strong. In this world, we’re more data-driven than ever. I take a lot of time and effort to try and hone my skills analytically to ensure that I’m in a position where I can look at a chart, I can look at data, and I can make not just a flippant choice but a well thought through choice because the data is there. If you can take the data, you’re likely to be able to find the answer that will drive the right level of decision making.

It’s amazing. It reminds me of something I heard roughly from Google years ago which is was, “I don’t care what you think. What does the data say?” Let’s go back to your 22-year-old self. You’re graduating college, you’re getting ready to start in your career, what advice would you give yourself back then that you know to be true now?

When you’ve got an idea, run with it. Early on in my career, I would second guess myself and say, “Is that idea good enough? Is that idea strong enough?” In many cases, the answer would be no but that would lead me to the next idea, which would then lead to the idea. Running at ideas, not stopping and letting your fears fly out the window and be headlong into turning ideas into reality would be the advice I’d give. It took me 10, 15 years to figure that out. When I did, it was truly transformative for me.

That feels like The Hero’s Journey. We’re right back to running again.

It is one big circle. Joseph Campbell was right. In The Hero’s Journey, it is one big journey. Once you’ve gone back out and you have slain the dragon and you’ve come back to the village and shared what you’ve learned, it’s time to do it all over again. I love doing that.

I’m glad we’re back to running again. Brett Pinegar, the Chief Operating Officer from LiveIntent, thanks very much for sharing with us on show.

It’s been a pleasure.

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About Brett Pinegar

SIC 123 | Email MarketingBrett Pinegar is the Chief Operating Officer at LiveIntent and has overall responsibility for the revenue organization and key operational teams. Brett’s focus is on helping his team to help their customers win using the power of email as a people-verified, media channel. 

Brett brings over 25 years of executive leadership from serving as CEO to three separate technology companies including Akopia, an open-source e-commerce platform that was acquired by Red Hat Software. 

Brett has also advised and coached hundreds of technology executives. He is a passionate trail runner and student of leadership.


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