Ad Ops All Stars: Scott Messer, Leaf Group

by Kathleen Booth, on Jun 9, 2021 9:00:00 AM

Scott MesserScott Messer is SVP, Media at Leaf Group where he overseas revenue operations across Leaf Group's Media division and manages a portfolio of 40+ owned and operated, vertical-focused websites.

In his decade plus of work in advertising, Scott has been responsible for third party monetization, revenue and yield operations, vendor management, contract negotiations and advertising technology.

Prior to that, his early career included stints working on feature films, doing business development for National Lampoon, and in development at an investment bank.

In this episode, Scott talks about how his early work in film, comedy and investment banking led him to the world of advertising, why becoming a leader means developing industry relationships and having opinions, what his predictions are for the return to "normal" in the ad ops world post-COVID.

Listen to or watch the full episode, or read the transcript below, to hear Scott's insights.

Resources from this episode:

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Kathy: Welcome to Ad Ops All Stars Podcast. I am Kathy Knott, your host or your hostess. Today, we are lucky enough to have Scott Messer, who is SVP of Media at Leaf Media or Leaf Group. Sorry. Thank you so much for joining us today, Scott. I really appreciate you taking the time. I know you're busy.

Scott: Oh, you're welcome, Kathy. It's my pleasure. Don't you mind.

Kathy: You know what's also a little bit annoying is when the guest has better hair than the host. That's a little bit annoying. It is actually the hair.

Scott: It's why it's a podcast. Most of the time.

Kathy: Yeah. I will tell you, I cheated a little bit though, and I saw your podcast with What Happens in Ops. I got to tell you, your Zoom game with backdrops is very, very strong. I was super impressed.

Scott: Thank you. That was early pandemic days when the novelty hadn't worn off yet. It was a great way to welcome people into the world of Zoom and to make it a little bit more comfortable and to let some of my personality shine. Then, somewhere around May, I think it was last year. I just lost most of my desire to really go deep in the backgrounds.

Kathy: Yeah.

Scott: Still pull them out every now and then. There was something about time to get back to work.

Kathy: Yeah. Stop goofing around.

Scott: I just invested in flowers, instead.

Kathy: They're beautiful. It looks very nice, but I will tell you, I really, really liked the rainbow lion. I think that was my favorite.

Scott: That is certainly top of the list. Thank you. I will let the rainbow lion know your appreciation.

Kathy: Also, I love Erik. He's my favorite. I actually just had a happy hour with him last week. I'm a huge fan of Erik.

Scott: Erik's a fantastic individual.

Kathy: Yeah. Luckily. we're in Maryland. He's in DC, I get to see him now and then.

Scott: Nice.

Kathy: One of the... We're also, really big Howard Stern fans together. We have that in common. One of the things I typically start out with is like, how do you explain what your job is? Running revenue operations for Leaf Group? What does that mean? It means so many different things for so many different companies? What does it mean for you in particular?

Scott: Great question. Probably one, we should start with.

Kathy: Yeah.

Scott: Revenue operations, for me and Leaf Group is everything that has to do with how money gets into the company, on the media side, at least, that includes order management, working with sellers up to the point of direct sales. Direct sales is really the only thing that we don't have inside revenue operations, third-party vendors, open auction, programmatic, the ad server. I always say that revenue operations owns the ad server. That is a big distinction I think, and helps draw boundaries for people. We are a shared service that runs across all of our portfolio and we're there to help all brands make revenue in all different ways, as well as facilitate the technology, the pipes and the systems that enable that.

Kathy: Wow. That's a pretty big role and that's pretty impressive. Do you do pricing as well for everything? Or do you have someone else do Yield Ops or does that fall under revenue Ops as well?

Scott: Yield optimization and pricing are both inside of our group. Yep.

Kathy: That's fantastic. That makes it easy for you. You're setting the price, right?

Scott: We do. We take a stance that open auction, actually sets our floor pricing and then we build on top of that. Since we manage the open auction stack, we say what clearing prices and then sales, we give them numbers and targets of where they need to be and then they layer on, on top of that for what they need to accommodate commissions and other functions. One thing I like to say about our team is we are ruthlessly agnostic about Yield. Money is money and it's not so much where it comes from, but what it's doing to your stack. We ensure that that's happening fairly and consistently across our clients.

Kathy: Scott, question for you on that. You're agnostic. Okay. You're handling everything that's coming in that is programmatic, right? You're setting the floors basically based on what the market demands are. Then, you've got this whole group of sellers who are out doing direct deals with iOS. I've worked with sellers my whole life and I know they're not always going out with the price on the IO that you've set. There's always circumstances that we approve. What happens when an IO, which is guaranteed goes out and maybe it's lower than your set floors that are programmatic? I don't know what your supply looks like across all of your brands, but someone goes and sells a big video campaign. Do you have enough supply to fill that if the bids that are coming in programmatically are higher than what was in that IO? How do you handle that situation ?

Scott: Delicately? I like to think that our pricing guidelines are adhered to, and when exceptions need to be made, they're done for the right reasons. We have a lot of advertisers with different relationships where priority, preference and pricing are really important to that relationship. There's all caveats and nuances that can be agreed upon, but they're usually in trade or an exchange for something.

Kathy: Right.

Scott: I think to a larger Yield sense, you can't look at just your average. You have to look at the spread of your average and the number of standard deviations that you have away from it. Nobody clears all of their inventory at one single price to drive an average, you clear it $10 and you there $30 and you get a $20 average and then there's skew and kurtosis and whatever statistical terms you want to bring back. You can sell inventory under your clearing price, but you just know that you're moving a big block at that price and that may actually be better for your stack to sell it under your average.

Kathy: Right.

Scott: I know that it's a guaranteed, 100% fill, low discrepancy, good partner. There's something to be said for selling things reserved at a good price. It doesn't have to be the highest price always.

Kathy: I'll take that deal any day for sure.

Scott: Yeah.

Kathy: In terms of your supply, I got to be honest, I don't know a ton about it. I would love to hear from you. In terms of like, if you're going out and doing that huge agency deal, so you're going out and doing like an Omnicom deal or something like that, and you want to have like a global agency deal and it's video. You know that agency wants to be with you because you're owned a property. They're brand safe. They can trust you. They know it's not UGG and it's going to be safe for them. What do you do when they go out and are trying to do this big partnership? Do you have enough supply across the board to do those types of huge deals? Or how do you manage those as well?

Scott: It's not about the size of your inventory. It's about your ability to use it effectively. What's big for a video publisher is small for a regular publisher and what's big for a regular publisher, maybe insignificant. I don't like to think of like, "Whether we have enough supply to handle an agency deal or not." The question is, is like, "Is what we have important or meaningful to a buyer?" If it is, we can find a relationship to work in there. Nobody's going to bring you more scale than Roku or Hulu.

Kathy: Right.

Scott: Trying to be anything that gets near to that is just few tiles. You have to be very comfortable with what you are and what your inventory is and work with that. You might be too small for some people and you might be too big for others and you just got to keep looking for your partner.

Kathy: Yeah. It's funny you say that because it is really about looking for that sweet spot, because it's impossible to compete with the YouTube's of the world out there. People do want your content because they can trust it. You've got that seal of approval, which is very rare and unique. You're actually really lucky. You've got that little sweet spot. Definitely. I mean, not that the job is easy, but it makes it easier in a way. Don't you think?

Scott: Yeah. Sell what you got and stand behind it.

Kathy: Yeah.

Scott: You can think about farmers at a farmer's market, right? There's the organic section, there's the non-organic section and then there's a regular groceries and they got their food and then you go into Costco and that's like a whole different thing. There's always something for somebody. You have to understand realistically what you are and the value of it to your consumer. Maybe it has different values to different consumers and you have to understand that.

Kathy: I'm sorry, you're just making me laugh because when you say sell what you got, you must have the most amazing sellers who actually sell what you have, because I bought... It's really hard to get a seller to sell the apples that are in your apple carts sometimes. It sounds like you work with a really great team.

Scott: We do have a fantastic team and our sales people are amazing. They like to learn, they love the new shiny things, which is why we bring them new shiny things, even if it's just polishing some older things that we have. As revenue operations team and when you're talking about products and rich media, data, audience data, and different things, you have to continuously push these and market them internally, so that your team can market them externally.

Kathy: The question on that. I'm just super curious about all this stuff and how you do it? I'm always wondering how people are successful at their jobs and it sounds like you are successful at it. Are you then working with product really closely to figure out what is the next new audience tool or the next rich media creative that we can push out? Are you really pushing on them to develop something for you quarterly? Are they just really proactive in bringing you really great things? How does that relationship work?

Scott: More of that research and work on the product level is inside of our own team. We talked to the vendors, we do the testing, we do work with engineering and product to see if we can get things to fit, or if we need to add things to the sites. Everybody has a very balanced understanding of Yield and the importance of user experience across our properties. The ideas may come in from different places and it may come from a seller or an account manager or a Yield analyst and like, "Hey, this is a good product or an idea. Can we try these?" Then, they get into the right hands across the team to develop tests that figure out which vendor is better. Whatever the process may be, and then we go and release that product.

Kathy: Got it. You're lucky that you're able to just constantly work with vendors to bring in solutions as well, because the hardest thing is like you said, they want something shiny and when it gets stale, it's like, it's hard to get a seller motivated to sell the same little thing. They want something new and so you constantly have to be innovating. What's the big item now?

Scott: Oh, there's always big items. The thing that I'll say about those partnerships with our vendors, and I really do enjoy them and I appreciate all the work that they put into building their products. The one thing that they'll know if you've worked with us is that we are absolutely honest in our feedback. We will tell you where your product sits within our organization and we'll make a guess of where it sits in the marketplace. Some things are nice to have, and some things are great. Some things are like, "This is so awesome, but I just don't know how to use it." Or like, "My organization isn't at this level yet." I'll call you when I do start doing that thing, that currently we don't, and the Leaf for me, to implement it is just way too large.

Kathy: When you're planning your budget, your fiscal budgets, do you put in an amount, not just for the current vendors that you have, obviously that you'd like to use, but do you always have that little extra bucket for the next shiny thing that you're looking at?

Scott: Nope.

Kathy: How do you do that?

Scott: Well, the budget's set. It can always be offset by sales and become a cost of goods sold, but typically our budgets are fixed, which is why the majority, I think of vendors and their business models are more transactional. If you use it, you pay for it, if you don't use it, you don't pay for it. It's very hard for me to sign up for SaaS based services when I can't demonstrate the clear value for them. Declare immediate value or return on that investment, or what it's going to replace. I've told a few vendors several times that you do this product and you do this other thing, and if you can replace this other vendor that we have, you can have that budget.

Kathy: You can a business.

Scott: Absolutely. They go, and sometimes they're like, "You know what? That was actually a really good idea. We did it." And I go, "Thank you." Sometimes they go, "Well, that's just not where we want to be." I said, "Okay, we'll let you know when X, Y, or Z changes and we can make room."

Kathy: That's awesome that you have the ability to have that candid feedback because everybody wants to grow and learn and to be able to have a relationship, whether it's vendor or whatever it is, and just be able to give that candid feedback. I think is just good for everybody across the board.

Scott: If you're not learning, what are you doing?

Kathy: Exactly. Drinking, I guess. This is not Ops related, but to walk me through this, how do you get from being in film to being in media? Walk me through it? Where's the connection?

Scott: Sure. Film was my early days right out of college, went to work for a film production company, had a lot of fun there and straight to DVD movie called Urban Legends 3. Wasn't the beginning of my film career. You can dive deeper into my IMDb and go find me. Then, I went to business school thinking I wanted to be a producer and make films for a living. As I went through film school, I got further and further away from actually being a producer and wound up taking a job that valued three skills that I have, which is analytical, creative and production, because I knew a lot about production. That put me into the Laugh Factory recording standup comedy.

Kathy: Oh, wow.

Scott: It was early YouTube days. It was 2007, which was right when YouTube was really founded. Very early on the distributing standup comedy side. Then, that meandered into National Lampoon and business development and sales, and then started really finding a love for business development and ad tech and how this ecosystem works and was lucky enough to make my way into what was then Demand Media and is now Leaf Group in 2012 and just really fell in love with this business because you can build things and make things and see them go live within days or weeks or years, as I've also learned. I've really enjoyed the community that we're with and the people that we get and it's so much fun to teach your teams and the group of them and see everybody working together. Maybe it's just something that are... I think that's probably true for any industry, but I understand ad tech, I like business development. I like digital media. It's just easy to be here.

Kathy: That's a perfect answer. Are you still doing standup?

Scott: I'd never did stand up.

Kathy: Oh, none at all. Okay.

Scott: We were recording comedians.

Kathy: Got it. Are you still recording?

Scott: No, not with Laugh Factory. Laugh Factory does their own thing.

Kathy: Got it. That sounds like a fun time though, for sure. National Lampoon sounds like a good time as well.

Scott: It was an interesting experience. I really enjoy it. They gave me my start. They handed me a phone book and said, "Go sell some ads."

Kathy: Which led you to where you are.

Scott: It led into this. I have a deep respect for sales and the relationships they build. That's something that I've always carried with me and I think is very helpful. If you were going to be a general manager or run some of these businesses, you must have the empathy to lead and the understanding of what other people are going through, because everybody is a service organization to somebody else.

Kathy: Yep.

Scott: Through that, you must understand what their needs are, what they're going through, what their challenges are, because you're trying to solve problems. Essentially, the problem is how do we work together and how do we solve a problem together? That's what all of this boils down to. If you can put yourself in somebody else's shoes and understand what they're thinking and why they're having problems, it's much easier to teach them and build them and grow them into department that you want.

Kathy: I couldn't have said it better myself. I mentor a lot of people as well because I feel like it's a very young industry and I'm old. Specifically, in Ad Ops on my side, on the demand side of the house, we get a lot of young people just starting their careers that are coming in. I tell them, very similar to what you just said all the time. It's like, "Everybody has a different personality. Everybody has a different song." I always use the snake charmer analogy.

Scott: Okay.

Kathy: If you can figure out what their song is and get them to dance, you could do anything. Everybody has their own song. It's up to you to figure out what it is. It's not that hard. You just have to actually listen to them and understand what they're trying to do. There are people, by the way, who have amazing song books. They can play every song out there. It's beautiful to watch, but it really is about building relationships. I think that's important in this career and your personal life. It applies to anything, really.

Scott: It certainly does. Relationships are incredibly important. I think for the people starting their careers in ad tech and in any industry, you have to understand what your career path is and how much movement that you have in those roles. You can't always be just an Ad Ops for your whole life. There are career professionals that do it and that's important, but how are you going to make your jumps and how are you going to grow inside these organizations? Most jobs have two or three jumps in them before it's like a dead end inside that organization. When you start seeing that dead end, you can be senior Ad Ops associate and move up and then you realize, you look around and be like, "Why are there no senior vice presidents of Ad Ops?"

Kathy: Yeah.

Scott: Right? How far can I take this? You said that in business development, you see that in ad ops, you see in designers, there's all these things. That's just what an organization has capacity for, which is why you see a lot of people make lateral jumps into other organizations to push themselves up or upwardly jumps. The important part of what we talk to our employees about is, you have to define your career path and you have to tell me what you want to do. My job then is to help clear the path for you and put the obstacles in your way that you need to overcome and achieve to show your growth in that area.

Scott: If you're an Ad Ops person and you say like, "I do want to be SVP of Ad Ops." I go, "Great. Here's how long it's going to take. Here's what you have to do." This is what it means to be not just an expert in a master of your field, but you have to start having industry relationships and you have to start having an opinion and you have to stop taking orders and you have to start telling people what we should be doing.

Scott: Once you've put that power back into the hands of an employee, you see that they're unfounded reasons for needing a promotion, start to go down and that they start to understand the path that they're on and that they have things that they can achieve. They know that they need to be able to do this or that and they have an obstacle course. That obstacle course may take nine months, it may take a year and a half, because I say, "The time is not a reason to be promoted. It's your achievement and growth and responsibility."

Kathy: Definitely.

Scott: I tell people, what responsibilities are you going to take? If we don't have for you, my job is either to create them for you or to help you find them, which is where you find those great employees that invent new things. They're like, "Hey, we didn't have one of these before, but I turned this business, native, audience data, CTV, rich media." Something. They're like, "I figured this out and now it's big." I'm like, "Great. You own that now. What else are you going to go home?" Unless they start to realize that there're fond out of these careers. If you just keep doing the same thing and you don't change your attitude, you don't change your ownership and you don't change your responsibility, it's very difficult to come by a promotion and growth path.

Kathy: For sure. You sound like an amazing mentor.

Scott: You'd have to ask my mentees.

Kathy: I guess I do. I'll get to that in a second. I think you touched on something that we all know. It's got a short life span and you invest all this time into mentoring these people and you obviously become very fond of them and you've got this rock star team and they hit their glass ceiling, they want more, they're doing these lateral moves or these lateral raises and you're losing all your good people and you have to train again.

Scott: Yep.

Kathy: What's your take on that?

Scott: I take a much as difficult is. Losing great people happen and you should celebrate them on the way out, especially if they gave you good work and really... If they give an A, effort and gave you the time that is reflective of the amount of training that they got. Right? If you'd have to train them for one day, they can stay for a month. That's fine. If you have to train them for three months, I expect them to stay for two to three years. You want to see that commensurate reflection of effort from them, and then you should celebrate those people. Losing people is part of business.

Kathy: And life.

Scott: And life. Although, you can usually replace people in business that you lose. Losing people in life is a little more devastating.

Kathy: Yeah.

Scott: When I actually just said goodbye to an employee today, and we've had a couple others. Two employees went to pursue their lifelong passions, they were outside of Digital Media. One is having a baby soon and wanted to go have free time and take care of his life and put everything together. That happens.

Kathy: Yeah.

Scott: Probably, it's sad for me as a business leader, but it's incredibly powerful to see these employees do their great work and then move on, and it's okay. We go back and we find new people and we coach them.

Kathy: Yep.

Scott: A leader should ever chastise their people for leaving no matter what the terms are. You should have a conversation with your employee on the first day and ask them, "Why will you leave here?"

Kathy: Did you do that every time?

Scott: We're getting to. It takes awhile. It's hard. We actually ask it during the interviews. We said, "Everything is going well, why would you leave Leaf Group?" First of all, nobody ever expects that question. It's a good judgment point. Second, you learn a lot about the person and what they want and what they don't want and what motivates them. Usually, their answers are something like, "If I'm not being motivated in X, Y, or Z, or if I feel that I'm being threatened." Or if I feel some very normal workplace things, and then you go, "Okay. I know what this person needs. I know their growth. I know what they want. I know that they want access to leadership. I know that they want training. I know that they need friends."

Scott: Then, you can help give those to that person. Then, when the day comes for them to leave, they say something to you like, "This is why I'm leaving. Here's why I'm giving you six weeks notice." Right? "Sorry. Six weeks?" They're like, "Yeah. It's a tough job and you need time to change it." instead of, "Hey, thanks. Bye. Here's two weeks. By the way, my last day is on Wednesday so actually, it's seven."

Kathy: Great. Or by, "I'll giving you two weeks notice and I have two weeks vacation time left so today's my last day."

Scott: I have those uncomfortable conversations up front and talk to your employees about moving on. Because most people... I don't know, under 40, under 35, I've only changed jobs once or twice or eight times, which was totally fine, but they were all under... Shut downs and pandemics and closures and all weird things and people have shell shock from leaving jobs. You need to give them the open space to discuss their employment and their careers. You can always walk into my office and ask when you're getting your rates. The answer may not change. Then, you can always ask me, "What's going on? What's happening. What's going on with your situation?" I will tell you as much as I know, and you will not be penalized for it or chastised for it in any way.

Scott: You need to know that if you can have that conversation, employees don't act irrational and they come to you and they're like, "Hey, I made a huge decision and it's final." That's the worst thing that a manager can hear. Why didn't you tell me about this earlier? Why didn't you say you were unhappy? Why didn't you tell me you wanted more money?" Right? Sometimes they're like, "I did. You don't listen to me." Then, shame on the manager. Sometimes the employee is like, "Well, I didn't think I could talk to you about it." Or, "I didn't know how to do it, and so I just picked up and left."

Kathy: Did that crush you?

Scott: It isn't even really that good.

Kathy: That would just crash me if someone came to me and told me that I didn't feel approachable. I gave them that vibe. I have to check myself for sure.

Scott: You're rare in that instance. Most people would probably say that, but not a lot of people proactively go out of their way to make themselves available to not be that.

Kathy: Yeah. For sure. Well, thank you. That's all super insightful. One question I had was, our industry is constantly changing. The only constant is change.

Scott: Yeah.

Kathy: Where do you go to typically, to figure out what's new in the industry? What's going on? What's next? Are there blogs that you read? Are there back before pre COVID? Are there conferences that you would go to? Where do you go to figure out? Where's the pulse right now?

Scott: Yeah. First, start with your passion. You have to want to absorb all this material. Second, once you do that, it's pretty easy. Follow the trades, AdMonsters, AdExchanger, Adweek, AdAge, pick up all those, find out what you like and what you want to follow, ad tech. Twitter is a very unique and interesting place. There's a lot of very smart people talking about the leading edge of ad tech on there. Then, certainly, conferences, pick and choose wisely. Do you want to be publisher facing? We want to meet buy-side facing? Which aspect of the industry do you want to learn about? Then, what are you doing with these insights? One thing to become very smart and learn, but this is how you form opinions. Once you start having opinions, you should be telling people those, and then trying to move your organization in a direction, or at least having that meaningful conversation.

Kathy: When did you back to conferences?

Scott: Soon. I hope.

Kathy: You got your shots yet?

Scott: A little bit.

Kathy: Yeah.

Scott: I think people will get back to them. It'll be interesting to see which ones come back first.

Kathy: For sure.

Scott: Smaller and bigger and bigger. Who knows? The virtual things super interesting, but it's not what it was. I think mostly sellers got to sell.

Kathy: Yep.

Scott: We're trying to get our salespeople back into offices, but we need people to be in those offices. I'm sure that vendors want to go back to conferences. If there's demand for that, there's always ways to get people to New York and Florida and Colorado and wherever it may be. It's probably not too far away.

Kathy: I hope so. I hope you're right. I can get a cross my fingers on that note. What did the last questions I always ask is, who do you think is doing a really good job in the world of ad ops? Obviously, that would be our next guest or someone that we would want to talk to. Who would you recommend?

Scott: Hard for me to narrow down a few. I don't like to list my friends out, but there's a lot of good ones out there. They're usually the unsung heroes and that's one of the hard part about it.

Kathy: Yep.

Scott: That goes back to the career piece like, you need to own your destiny. I can list off people and you've probably heard of them. I can't list off people that you haven't heard of because I probably haven't heard of them, but they're probably some of the best employees out there.

Kathy: For sure.

Scott: Ad Ops is a hard game and they're unsung heroes in there. Managers have a responsibility to at least offer those employees, the opportunity to raise their profiles, because you get to keep that. If you're a manager investing in your employees profile and employee is going to stay for a long time and you will have an incredibly valuable person. Some of them will leave to go cash it in, but I bet you more stay.

Kathy: It doesn't even matter if they leave because that loyalty, that bond is never broken. It doesn't matter where they go. That connection will always be there. I mean, you know this, you work so hard, so many hours, that is your family. Away from your family and the relationships that you formed with these people. I love the job. I love the people. I love making those connections. I can say I still talk to a lot of the people I've mentored over the years and so I feel very blessed and privileged to have those relationships. Anyway, that's all I have. I just wanted to thank you so much for talking with me on a Friday, even though it's mid day for you, afternoon for me. I just wanted to thank everybody out there for joining Ad Ops All Stars Podcast. If anyone wants to look at this, you could go on Apple Podcasts or any platform of your choice and check us out Again, thank you, Scott, so much. It was really a pleasure getting talk to you.

Scott: Thank you, Kathy. I really appreciate the time. It was fun chatting with you.


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