Episode Summary
In this episode of Leap to Scale, Justin Davis and Greg Ross-Munro are joined by Aaron White, CEO and co-founder of outbound.com, for a conversation about one of the core themes of the show: transforming services into scalable software products. Aaron shares the journey from founding Script, an education workflow automation company later acquired, to launching outbound.com, an AI-powered advertising platform built on top of a real marketing agency. Instead of starting with software and searching for customers later, Aaron took the opposite approach by acquiring an agency first and then building technology around proven workflows, operational knowledge, and customer demand.
The discussion explores how agencies can identify automation opportunities, the economics of turning service margins into software margins, and why understanding human behavior matters as much as understanding technology. Aaron also explains how AI is dramatically accelerating product development, why the “human layer” may become the premium tier of future businesses, and how founders should think about scaling teams, culture, and systems in an increasingly AI-driven world. It’s a practical conversation for agency owners, operators, and founders trying to figure out how to survive and thrive during the next wave of technological change.
Episode notes
- Aaron White explains why he acquired an advertising agency before building Outbound.com, instead of starting with software first.
- Buying the agency gave Aaron and his team immediate access to industry expertise, real customers, active revenue, and firsthand knowledge of the problems they wanted to solve.
- Aaron contrasts this approach with his previous startup, Script, where the team built the technology first and then developed the business around it.
- The team identified opportunities for automation by measuring where employees spent the most time and comparing those tasks against their impact on revenue and retention.
- Aaron shares why productizing services is not just a technical exercise. Employees need to understand whether technology is meant to assist them or replace parts of their work.
- Outbound.com uses AI to analyze a company’s website, understand its brand and services, identify customer profiles, and generate advertising campaigns across multiple channels.
- The agency became the testing ground for the software, with internal teams using early versions of the product on real client campaigns before it was broadly sold.
- Aaron explains why smaller customers may prefer self-service software while larger clients often still pay for greater access to human expertise and support.
- AI is dramatically increasing engineering and product-development productivity, making this an especially strong time for service businesses to experiment with productization.
- When companies begin to scale, Aaron sees people and culture as the hardest problems. He describes policies, procedures, and culture as a slider, with strong culture reducing the need for rigid process.
Episode Transcript
Why Aaron White Bought an Agency Before Building the Product
Greg Ross-Munro: Today we are joined by my friend, Mr. Aaron White. He’s the CEO and co-founder of Outbound.com.
Aaron has spent, as long as I’ve known him, building products and companies. He founded Script, which was later acquired. We’re going to ask him about that a little bit later.
But what makes Aaron especially interesting to our audience, Justin, is that he is on the exact path that we talk about right now. He runs a professional services marketing and advertising agency, and at the same time, he’s actively turning the systems behind that agency into a scalable software platform with Outbound.com.
It’s the journey that we talk about all the time, from services to systems to product. It’s something that a lot of founders talk about, but very few people actually do.
Aaron is one of the most creative hustlers I have ever met in my entire life. The man has won Emmys. He’s taken me to the award shows. He has always got a plan.
So we’re really excited to have you here with us today. Mr. White, how are you doing? Thank you for joining us.
Aaron White: Thank you for having me. I appreciate that. I’m doing good.
Greg: Awesome. Tell us a little bit about your origin story. You don’t have to tell us the entire thing, but how did you go from starting Script, or even before Script, to getting where you are today?
Aaron: I started Script when I was 23. I had just gotten married, and I was like, “You know what? I’m going to do a startup,” because that’s the sane thing to do.
Justin Davis: Great plan. Great plan.
Aaron: I ended up getting hooked on the idea of starting and building something from watching the movie Jobs with Ashton Kutcher. I watched it 50 times on Netflix, or at least I think it was Netflix.
I was like, “I’ve got to build something.” At the same time, Netflix had Breaking Bad, and he was building this empire. So I thought, “Okay, I’m not going to build a meth empire. I’m going to try to build a startup that I could change the world with.”
I became obsessed with finding problems. I had a bunch of really bad ideas. Then we eventually landed on Script.
I think how I got into it was just exhaustively trying to solve every problem, no matter how silly that problem was. That eventually led into the first real problem, which was Script in the edtech space.
Greg: What did Script do?
Aaron: We helped digitize the back office for K through 12 schools and school districts.
There are all these paper processes riddled throughout schools, hundreds and hundreds of processes. We took those, digitized them, and made them super simple.
It was kind of like a workflow automation platform built for K through 12. Think DocuSign meets Zapier meets Google Forms, specifically for education.
Justin: That’s interesting because something we talk so much about on this show, and what we’re going to talk about here, is exactly that.
You take these manual processes that become bottlenecks in a people-constrained environment, and then use technology to automate them, productize them in some ways, or simply make them more efficient.
That definitely laid the groundwork for what you moved on to do at Outbound.
Aaron: Absolutely.
Now we’re taking advertising and making it as simple as possible for brands to get their brand out there to the right people, catch the attention of the right buyers at the right time, and make AI advertising as simple as possible for everyone.
Greg: Why would anyone need that? If I want to advertise, I know what I want to advertise. I’m a business owner. I know what I’m doing. Why would I need AI to advertise for me? How does it work?
I mean, I know how it works. This is a leading question.
Aaron: Before I even got into advertising, I was like, “I know how this works.”
Going in, it is unbelievably complicated.
You have to make sure you have the right message on the right platform with the right settings, then find the right people, follow that up, do the tracking. It is a lot of work. It is a lot of ongoing work that needs to happen.
I used to think, “Let me just go into advertising and totally change that market. That sounds super simple.”
It is crazy complicated.
Greg: I’ve been in technology my entire career. I’ve been on the web since basically the beginning of the web. I feel like I know a little bit about online advertising and web advertising.
But if I wanted to do a campaign, and when I have done this, I’ve hired an agency. I didn’t set it up myself. I feel like maybe I could do a little bit, but these people are experts.
You had a strange origin with Outbound. You knew that was the space you wanted to be in, so you went and invested in an actual professional services agency, right?
Aaron: Yes.
I knew I could figure it out, but it would take me three years of putting my head against a brick wall. I’d get there, but I don’t have the time. I need to move as fast as possible.
Our approach has been different.
With Script, we had the idea, built the tech, and then built the business outward from the technology.
Here, we actually acquired an agency and built the technology around that agency. We built it the opposite way. So it’s totally flipped.
We’re taking all the institutional knowledge from the advertisers and marketing specialists and injecting that into the technology. It was much, much quicker.
Greg: That sounds like the model you sometimes see with big private-equity-backed companies or venture capital.
Where did you come up with that idea to do it that way at your scale, while you were still starting up? That’s a pretty bold move.
Aaron: We were coming into an industry that we didn’t know. I had been in edtech for the previous 10 years, so I knew edtech really well.
Going into small-business marketing, I was at a little bit of a disadvantage.
In some ways, I could look at it through fresh eyes and ask, “Why are we doing it this way?” There are a lot of benefits to that.
But I knew I needed people who had been in the industry, and I wanted to leverage that as much as possible.
Greg: So you needed the expertise, the systems, and the processes before you could really build the technology. You and your partner could handle the tech, but you needed to understand the business.
That’s why you went and bought it. Then you also got to work inside it.
Aaron: Exactly. You get to see it firsthand.
There’s another thing that isn’t super glamorous, but from a realistic standpoint, it makes you much harder to kill.
You already have a product from day one that you’re selling. You’re servicing customers, understanding their problems really deeply, and talking to those customers.
You can grow this side of the business while you’re growing the other side of the business.
The name of the game when you’re a startup is just to be a cockroach. Be hard to kill.
The one that stays around the longest is usually the one that wins.
I wanted to take a different approach, and I do think it’s the right approach for this instance.
Justin: So you acquired the agency and started to build an exoskeleton onto it, if you will, that automated or systematized some of the internal things the agency was doing.
You write ad campaigns. You go set them up. You click through all these settings. Then you start writing workflow software that can do those things.
Walk us through how you went into an agency doing all this manual work and started cherry-picking the pieces that you could build into a product around it.
Greg: That’s what cockroaches have, man. Exoskeletons.
Aaron: We started by looking at the fact that agencies are selling hours. You’re selling people’s time.
We wanted to maximize that.
I looked at the numbers for the market as a whole. Agencies typically operate at around 14 percent pre-tax margins, somewhere around there.
The question was: How do we get software margins out of this?
For us, it was super boring. We calculated what everyone’s time was every single minute of the day and looked at where the biggest time sucks were.
Then we asked what value each task provided to the company from a revenue standpoint. What type of revenue is it? Is it new revenue? Is it retention revenue?
From there, we built giant Miro boards showing all the processes and looked for the easiest thing we could tackle at the right time that would give us the best bang for our buck.
That’s the way we approached it.
Greg: That’s genius.
You say it’s boring, but that’s the genius way to do it. That’s what Justin and I talk about all the time.
You work out the process, determine where the lowest-hanging fruit is with the highest ROI, and you start there.
Justin: It’s so easy to overcomplicate it.
It’s so easy to try to come up with a strategy when sometimes it’s just: Count the number of minutes you spend doing the thing. Sort by the most minutes. Then qualify it by biggest impact.
It can be very simple and very boring, but very effective.
Aaron: It can also be super tricky.
From a startup perspective, it sounds like you can just go in and do that. But now we have this new entity that we acquired with real people, real humans, and real emotions.
Now we’re analyzing everything.
So you have to think about the way you go about it and how you bring the team along.
You have to explain: “Here’s why we’re doing this. This is what we’re doing.”
That’s the other side. You need to make sure we’re all on the same team, everyone knows that, and we’re all headed toward the same goal.
You can have a software company you’re trying to grow out of an agency, with one growing one direction and the other growing another. You have to make sure everything is growing together.
That’s one of the tricky things to do.
Greg: Do those people become subject matter experts inside the product side of the company?
How many people on the professional services side become SMEs for the product? Or are you mainly talking to them, learning as much as you can, and then translating that to the product team?
Aaron: Right now, we’re trying to learn as much as we can and transfer that to the product team.
Some of them work very closely with product and have consistent meetings, but that’s where we are right now.
Greg: Can you quickly describe what the product does today?
Aaron: Yes.
We’re trying to make it as simple as possible to get your brand out there.
You make an account, then type in your website. From there, we’ll scan everything on your website.
We’ll learn everything about you and pass that into AI. We turn that into what we call business context.
That includes your brand, your colors, your tone of voice, your logos, large logos, grayscale logos, all that stuff. We categorize everything.
Then we look at your services and sub-services. We look at your customers and make customer profiles based on who we think you’re selling to, based on the data.
We also look at your service areas and locations.
We’re categorizing everything about your business.
From there, we ask you just a couple of questions whenever you want to launch a campaign. Basically: who, what, and where.
What customer profile do you want to advertise to? What service are you advertising? Where do you want to advertise it?
From there, we’ll reach out to the ad channel, look at the best keywords for that area and audience, and generate the campaigns, ad groups, and everything else.
Greg: So you’re talking about Bing, Google, search, LinkedIn, that kind of stuff?
Aaron: Exactly.
Then we’ll handle all of that. We make the creative, make the landing pages, spin them up, host them, handle the scripts and tagging, all of that.
Then the leads go right to a lead board for you.
Within about five minutes, you can have a campaign up and running and leads ready to come in.
Greg: That’s amazing.
When you started building the product, did you use it internally first? Did you eat your own dog food?
Or did you try to start selling it to people first?
Aaron: What do you mean?
Greg: When you started building the tools that have now been integrated into Outbound.com, were the people on the agency side using the early versions to improve and automate their jobs?
Or did you go to market before really using it yourselves?
Aaron: We gave it to them to run the clients through.
We’d scan the client, make a campaign, and say, “You also make a campaign. Let’s learn and see the difference.”
We’ve been having them use those campaigns when it makes sense.
Greg: Right now, where do you see the benefit and distinction between your two types of customers?
On the professional services side, you’ve got clients, and that’s probably much more hands-on versus the self-service customers.
What’s the big difference in what they’re looking for?
Is it a technology adoption thing? Is it a white-glove thing? Where do you think that breaks in the future?
Aaron: Right now, it’s really a function of budget.
Someone with a smaller budget can go on the platform, and we can optimize that smaller budget really well, at least based on some of the tests and things we’ve done.
Some of the higher-end clients want more communication with us.
They want to talk. They want to ask, “Hey, what’s going on?” They want a human to talk to.
Those are more of the enterprise clients.
Greg: Do you think that’s where everything goes one day? You’re going to pay extra for the human?
Aaron: I think so.
Justin: The human layer is always the gold tier.
Aaron: I 100 percent think so.
Especially when you consider what level of human access you want.
How much access do you want?
We’ve noticed this over the last 10 or 15 years. Customer service used to mean sending an email and waiting 24 hours for a response. That was the gold standard.
Now we have some clients who are like, “We need to talk to you within 30 minutes.”
So we bring them into a Slack channel.
The expected level of support has risen, even in just the last five years.
Greg: Do you think that’s because of automation, or because people’s expectations have changed? What’s driving that?
Aaron: I think it’s competition. Everything is rising.
Fifteen years ago, you could start with an MVP and get away with only having a certain number of features.
Now, if it doesn’t have full identity and access management and all this other stuff, people are like, “No.”
The bar has been raised, whether it’s customer service, product, or anything else. It’s unbelievably competitive.
Justin: As it gets less expensive to build that stuff, it becomes table stakes.
Then people start to expect it.
People go from one product to another product and expect a similar level of service.
Competitively, if it’s possible to give service within minutes, then the market will move toward that because some competitor somewhere is going to give the customer that experience.
Then they’re going to look at you and ask, “Why am I not getting that experience with you?”
Aaron: Look at Facebook 20 years ago and the amount of features it had compared with all the things Facebook does now.
It’s a marketplace. It has games. It has all these things.
We use Facebook and Instagram every day, and we’re desensitized to the amount of technology that’s in these products and even in our iPhones.
So when we see new software come out, we’re like, “Why can’t you guys do that?”
Greg: We feel that.
It’s like, “Why doesn’t this have an audit trail system built in?”
Is that needed on day one? Why do you build it on day one?
I guess that leads me to another question.
How long have you been building this thing? And has the speed of development gotten faster with new technologies?
Aaron: We’ve been building for a couple of years now.
The crazy thing is that just in the last six months, and especially in the last few months, the amount of productivity you can get from an engineering and product side using different AI tools is scary.
It’s crazy how much work you can do.
You’re seeing this throughout the technology industry. Some companies are letting large portions of their engineering organizations go because one engineer can do dramatically more work.
It is unbelievable now.
We’ve been cranking out more stuff lately than we’ve ever done in the past.
Greg: Let me ask you this a different way.
If you were starting today and you owned an agency doing something other than what you do now, is this the best time ever to build something?
Or is it already too late? Is whatever you’re working on already being done by somebody else?
Aaron: No. I think you have to lean into this stuff just to compete.
I don’t think it’s too late by any means.
Now is the time when you have more resources than ever to do almost anything you can think of.
So yes, I would say now is the time. Definitely not too late.
Justin: We’re probably still at the very early part of that curve.
The people who listen to this show include agencies, but also more traditional service companies with a lot of headcount. They have a lot of people doing a lot of manual work to fulfill services.
What advice would you give those people about how to take advantage of the moment we’re in right now?
How can they use some of what you’ve learned to find things in their own businesses they can start experimenting with?
Aaron: It goes back to my answer from before.
Understand what the best thing is to experiment with and automate.
We can pick a bunch of different things. But you need to identify, inside your organization, what’s going to give you the best bang for your buck.
A couple of years ago, especially with people like my parents, you’d see them doing little AI things. It’s like, “That’s cool, but what is it really doing?”
Sometimes it’s almost more of a hindrance to set it up and use it.
My advice would be to identify the thing that can really move the needle for you at the lowest lift.
That exercise alone, before you even start automating the service work, is probably the biggest bang for your buck.
Focus on that.
Justin: Earlier, you mentioned that it’s not always as simple as sorting by how many minutes you’re spending on something and automating the biggest one, because there are people and emotions involved.
These are businesses full of people who have feelings, thoughts, and perspectives.
What do you have to watch out for on that side as you do this?
Aaron: We use this example: Are you building full self-driving, or are you building assisted driving?
What are you building? And what are you selling to somebody, especially when you need buy-in from those people?
Understanding the human emotion behind that is really interesting.
For instance, are we building a service, or are we building a tool?
Are we building a service to replace the person because it does everything from A to Z? You can say, “Now you don’t need to spend money here. You can just do this.”
That is scary to people. It’s scary to anybody.
Or are you building a tool that helps assist them in doing their job better?
Identifying which one you’re doing matters because they mean vastly different things to people.
Greg: How does somebody decide which one they want to do?
Aaron: Sometimes that’s a marketing problem.
Justin: These are all marketing problems, aren’t they?
Greg: For you, everything is a marketing problem. That’s your lens on the world.
Aaron: It’s about how we’re presenting it.
If you’re presenting it as, “Hey, this is going to eliminate your job. Now you have time to do other things,” that can be a scary thing to hear.
You see that in other industries when new technology gets introduced.
Or are you coming alongside them and making them the hero?
“Hey, this makes what you do more significant and better.”
That’s a very different message.
Greg: You probably went through this more with Script than where you currently are with Outbound, but what happens when something starts to scale?
How do you move quickly enough when something catches fire and you’ve found product-market fit?
Suddenly people are knocking on the door. You can’t hire fast enough. Your servers are melting down.
What are the real-world problems that you’ve found in scaling?
Or to flip the question, what things did you scale prematurely that you didn’t actually need to?
Aaron: For me, the hardest thing as we scaled was the people side.
Finding the right people is really, really hard.
It sounds simple. You’re scaling, your product’s taking off, you’re having success, getting articles written about you, and there’s all this attention.
But finding the right people is incredibly difficult.
I’ve tried everything you can think of to find the right people.
Then, once you find those people, how do you make sure the ship is heading in the right direction when you’re not in the room for every department?
You can do that through policies and procedures, or you can do it through culture.
You have to be really intentional about which one of those you use and how much you lean into each side.
We have more policies and procedures in some departments than in others because there’s more culture in some places.
You have to be intentional about the culture you’re building, and then intentional about how many policies and procedures you have in place.
I don’t love policies and procedures, but my partner loves them. He’ll go super hard on them, and I have to pull him back and say, “Okay, we’re going to step back from that.”
It’s a giant slider.
Greg: I really love that idea that policies and procedures and culture are somewhat interchangeable, almost like a slider.
If the culture of a team already handles something well, you don’t necessarily need to burden them with policies and procedures.
That could almost feel like you’re speaking down to them.
If you come in and say, “The way you guys do your work is great, so now we’re going to take what you’ve got, bottle it, and put it into a formal process,” that might actually be condescending.
Whereas for a newer team, or one that doesn’t yet have that culture, giving them that scaffolding can help build it.
I need some time to marinate on that. I love that idea.
Justin: Policies and procedures are rule sets that fill the gap where those norms haven’t naturally formed.
They can be training wheels.
They might even be something that progressively goes away as the culture replaces them, or replaces them with its own versions that are acceptable to that group.
That’s fascinating, man.
I hope people are listening to the end of this show because we just dropped the best part in the last few minutes.
Greg: Stay till the end!
We’ll go back and record an intro and say, “Don’t forget to stay to the end, because that’s where the most insight will be.”
Aaron: Clip it.
Justin: It happens somewhere between minute five and minute 30.
Greg: Aaron, I really appreciate you spending the time with us today.
I’m constantly impressed by the stuff you’ve built, the hustle and creativity you put into things, and the way you’ve tackled building Outbound.com.
I remember you going through a million ideas before you arrived on this. I remember you showing me early designs of 10 different business ideas after you exited Script.
It’s super cool to see what you’ve built and how impressive the product is.
I would highly recommend that anybody listening to this goes to Outbound.com and signs up for a demo.
It is really impressive as a piece of technology. I think it’s solving a huge problem.
And I think it’s both a tool and, if you need it to be, something that can replace some of the work your people are doing internally.
Aaron: Thank you. I really appreciate that.
Greg: All right, buddy. Have a great weekend. It was nice to see you.
Justin: Thank you.
Aaron: Good seeing you guys. See you.