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The Power of Transparency

The Strategy and Leadership Podcast with Anthony Taylor


Welcome to the Strategy and Leadership Podcast, the podcast that brings you practical advice, lessons, and stories from senior leaders and thought leaders from around the world. The Strategy and Leadership Podcast is brought to you by SME Strategy, working with organizations around the world to create and implement their strategic plans.

To learn more, visit And  now your host, Anthony Taylor.

Anthony: Hey there, folks. Welcome to today's episode of the Strategy and Leadership Podcast. My guest today is Claire Milligan, who is the CEO at Aimably. Claire, how's it going today?

Claire: It's going great. How about you?

Anthony: I am fantastic. I was telling you I had a hard time with my buttons today. For now, I only really have to press one or two buttons because I get to chat with you for a while.

I'm excited to have you on the show. You talked a little bit to me earlier about your product experience evolving and growing in that space. I know that you speak on neurodivergence from time to time, and,  you are  in the middle of a very cool, CEO-ship journey, with a product that is needed in the marketplace.

But that's all I'll give for your introduction. Why don't you fill in the blanks for our audience and then we'll get into the chat.  

Claire: Great. My name is Claire Milligan. I'm the CEO of Aimably. And we help companies understand and control the money they spend on cloud hosting. That's AWS, Google, and Microsoft.

I got to where I am because I had worked for a business named Emburse. I had been Chief Product Officer and also General Manager of a line of business. That business line had to be transitioned.  I was brought in to take formerly a growth engine and to turn it into cash cow so we could invest in other lines of business.

And so together with I like to call my sidekick. Sometimes I'm Batman and he's Robin and the other way around some other times, Mark and I started looking at a lot of our cloud hosting costs in order to be able to reduce them and to turn that line of business around.  Well, I'm really proud to say we did.

I did a lot of transformation in that line of business. It required becoming masters of something that I previously had no experience in. And once we accomplished that, we really realized there was an opportunity to go out and create our own business. So here we are today.

Anthony: So how does the mind of a successful product owner think like, do you walk around all day looking at stuff and being like, well, that's wrong, or I would do this better or internally your gears are just always on like sticky notes and whiteboards tell me how you think and how that's led you to success from where you're at right now.

Claire: You know, as a leader, I very much try not to prescribe a certain set of behaviors of what's good and what's not.

I like to let people find their own way in terms of operating their own. But for me, yes, I do evaluate everything as I go. I actually like to tell people that when I was a kid, my, my dream job was to be, a car designer, because I felt like there was a right and a wrong way to understand how you were moving in the space of a car and how it will work and that it should just be so brain dead that it should function. And so a lot of people think about the outside of a car and I was thinking about the inside and how you use it.  So yes, absolutely. All of those things, thinking about how it can be tweaked and refined is kind of what I spend a lot of my time on.

And you mentioned neurodiversity, but that's actually sometimes what I can spend too much of my time on because I can try to really focus  on solving those problems. But when you're a founder, I suppose over focusing and solving problems helps.

Anthony: Well, I mean, you're supposed to get into a necessary amount of trouble as a founder.

So let's take your journey, right? You've gone from looking at products, solving problems. You're obviously are in the middle of this now, but let's focus on the product manager lens. You know, you talked about the inside of the car. A lot of our listeners, our CEOs, they could be product owners, if not in technology, some other thing.

What are some of the kind of questions that you ask yourself as you begin the either product improvement process or problem solving process? What are the steps you follow just to try to figure out how you think? Not that anybody needs to think that way.

Claire: Sure. I think it really depends on the stage of business you're in.

I've been a product leader in a variety of business stages. If you're thinking about growth, it's all about finding avenues for the way people behave to try to get work done that they infuse with process which they cannot solve any other way. The novel opportunity for real growth and real product-led growth is to find things that take the most amount of people's time and just condense them and solve them for those people. Don't just show them how it is. Do it.

For me, I'm a huge believer in financial analysis. And whereas there are plenty of product people out there who will say, You know, we have no idea how much this money we can make off of this.

I believe it's fully quantifiable.  You can look into customer support cases. You can tie systems into Salesforce and understand what your sales demand is. And you can multiply out by the value of customers and how many are talking to you about an issue that they encounter or a feature that they'd like.

You can compare that to how long it'll take you to build. And you'll know in how many months you'll pay back the effort you've done. It's incredible how much your customers love it when you deliver for them what they're asking of you.

But one final note, don't build it exactly how they ask of you. You go back to that growth mindset and you say: "How can we really solve this in a way that's on brand and actually really resolves the issue rather than just, hey, put this button here."

Anthony: Absolutely. Well, I think one of those questions that CEOs, if they don't know whether they face it is the, the build versus buy dilemma or don't build or don't buy.

But what I really hear in the root of your thinking is the business case, like making sure that there's a business case. That's likely or almost certainly the thing that led to this new problem because they have a pain. Well, the only reason people will buy a product is that there's a business case for them and there has to be a business case for us.

And then there's how you think. So, how would you invite our, leaders to encourage strategic thinking, a la product manager, within their organization? Because as a CEO, and I talk to other CEOs, They own the problem wholly and completely. Some of their team members might not wholly own that problem.

They don't wholly own the solution or they don't think they own the solution. So if you were in a seat and you wanted people to think more like business cases and, and challenge them to do the quantifiable things, how would they do that?

Claire: We as CEOs own the problem because we have our incentives  directly in line with the outcome to the consumer.

If the consumer doesn't like what's going on, we don't make the revenue and we're not compensated in the appropriate way . The incentives have to cascade down from there.

We talk a lot about cascading goals and OKRs, but we don't ever cascade those incentives in the same way.

One of the things that we do actually is we do consulting with companies on trying to make sure that they reduce their cloud costs. And sometimes it requires engineers to do the work. So we say, "Hey, set aside this chunk of money on money you're going to be saving. Give it directly to the people who do the work," and all of a sudden, lights go off and everyone's owning the problem.

Anthony: I don't know why that was such an aha,  the money, I mean, I think maybe potentially it's hard because you don't know what you're going to get out of it.

An example that's kind of relatively close to my heart:  stocks were super cheap a year ago. And I'm like, well, if I have put this money earmarked for it and I have like strong confidence, it'll get to like 70 percent cause it's on sale. Why not put that 70 percent towards here?

And so what I hear you say is, if this solution, and I guess it means that you have to try to figure out the ROI of the solution, is going to save you a quarter million dollars, well, why not carve off some of that, as long as your estimates are accurate, into solving the problem? Is it just me, or is that too stupidly obviously clear? And then I don't mean it in a personal way, but it's like, well, duh, but I guess some people don't think like that if people don't think of like the ROI of a thing and then like the cost cost benefit analysis, because. I guess I guess my question is, why did they do that? Are they too busy? Do they not have the problem?

Do they not want to be specific? Do they just want it solved?

What do you see? Because I imagine and I'm sorry, I'm talking a lot. You've probably been on the flip side of things, where you're trying to convince somebody to invest in a solution. You're like, grr, why don't you see this?

Claire: Well, yes.

Certainly in thinking about what we should invest and spend. If I show how the incentives are aligned, I've always gotten a lot farther. But  the, the hardest part of our contract to negotiate is to set aside savings for the engineers  doing the work. You would think it's brain dead because, we have calculated how much it's going to go.

There's this reaction of, "Oh, people shouldn't be compensated like that. Why should we send that much money aside for compensation?" And my response is:  we do it for sales: compensation for commission . It's always out there. Always on the growth side. There's even some marketing teams are compensated that way.

It's no surprise that salespeople work in direct alignment with the goals of the company. Shouldn't we be thinking about that on the cost side too? Not many people are.  

Anthony: How would you say that compares to other technology companies? Because I know a full stack developer could cost you like, well, a quarter million is cheap.

Some of those folks that are really core to the product and product engineering in tech specifically are getting compensated. Would you say that's consistent in tech and should be done across all other functions?

Claire: It's a supply and demand question. I think that what's interesting is that people always go the next step and they say, "Gee, they're compensated so much. Wouldn't it be greedy to compensate them more?" I just say it's like On Target Earnings for salespeople.

If you make the On Target Earnings totally achievable, in line with the goals of the company, it makes sense.

However, this is actually entering the next point that I like to talk about , which is: I think the reason why we spend so much on engineers in the tech world is because we haven't gotten to the point of industrialization yet in the development of technology.

What we have is these couturiers who are constantly building their own code, which is like sewing this beautiful dress in Paris for the runway every single time. But this is for every single technology business. And yet, at the same time, you can buy these kind of looks from H&M or Zara or whatever low budget brand, but nobody knows how to develop code in these models where the focus is a bit of design, but  a whole lot of value engineering into how we run this at scale.

And I think that's really the next step for technology, but we're nowhere near that yet.

Anthony: Well, that's what I'm hearing. I try to stay on top of some technology stuff and where folks are moving away from these vertically integrated software solutions to spin up their own things in house because the ability to get into that market is becoming easier.

It'll be interesting to see how that  decrease of barrier to entry for having high value. Technology infrastructure will support folks like small and  medium enterprises, which will then kind of disrupt the industry. Which is great for you, especially if people are using more cloud computing solutions.

The person I just talked to  before this talked about technology and Bitcoin and tokens and all of that stuff. How do you feel about the integration of technological infrastructure across all of these kinds of industries, businesses? And I could ask it from a product lens, but I'm actually more curious from a CEO lens.

How do you see that moving?

Claire: Well, I think it comes down to: Does the technology advance your business meaningfully? There's an environmental impact to it. There's the conversation in the stock market about what is it? What are the true asset value? Is there kind of some kind of gold standard on Bitcoin?

There's a whole lot of ways that you can kind of come at this problem where it's somewhat problematic, but at the same time, even despite this weird bust that we had, it continues to grow in value. So it's hard to give you  a clear yay or nay on it.  

I think the take home question is: Is it worth it to us from a financial perspective to go about doing this technology this way? It comes back to your build or buy question.

We talk a lot to banks and they have historically cobbled together purchases into an operating system, and then they have to deal with all the data processes behind the scenes. The most advanced banks are now actually going out and writing their own code, just like you're talking about, but they do have to think about the cost over time to maintain and for all these engineers to continue to work and improve, which, if you're just paying the subscription fee, that's taken care of beyond your doors.

You'll have to think about how you evolve as a technology business when you weren't a technology business before this, and whether or not you can keep up with the evolution of the cost side, because then the other point is you don't ever have growth when your own client is yourselves.

It's just interesting to go down to thinking what is your company as a product? As all these entrants come in, the competition for all businesses becomes more fierce. Then the layer of integration between technology or not technology, is ultimately what differentiates businesses when it gets harder and harder to differentiate.

Anthony: Well, that's not how I thought our conversation was going to go, but it's super fun.

Open ended question: I guess I could ask around, leadership, people, what are your driving principles as you think about growing a business or building a team?

Claire: I think it's all about transparency. I think the word's overused though. Transparency and education work hand in hand. If you're trying to go somewhere and if you have a goal of the business, a lot of times leaders will say, "Gee, I really don't want the people to know."

If somebody is leaving the company, you say, " Make sure nobody knows until we have the right communication structure or, "We're planning a restructuring and make sure nobody knows."

I think that, actually, you have to start from the fundamentals of: people do what you want them to do when they understand the full picture. So if the company is staring down a restructuring process, you start with making sure you explain what the financial realities are, looking for help in adjusting that.

There's a particular example that, that we had, we did a major restructuring on this line of business I was talking to you about in the beginning. When you have a growth business, you have a whole bunch of really well paid engineers doing the growth business, and we didn't have that capability to move forward.

And these are people I'd worked with for like six or seven years. And I was being asked to be essentially the executioner, right? Go in and look at the problem, solve it as many ways as I could and find the right way. I just kind of laid it out to the, to the team. These were our finances.

We looked at the P&L together, every single one of us. And we're like, " How can we arrange this? How can we work with this?" Knowing the constraints of how the business operated. And then when it became very clear we were going to have to do layoffs, I asked people  whether or not they wanted to stay, knowing fully, you know, what it was going to look like once it was.

You can't do that all the time, you can't be transparent all the time, but you certainly can provide education as to where you are all the time and let people put together the dots and start working in the same direction. And, hopefully, people respect you for it.

It's all about everybody rowing in the same direction and then building those incentives behind it, you know?

Anthony: Yeah, and I can imagine that was a challenging thing to do, but you talk about everybody rowing in the same direction. I think that that was a great demonstration of where we're in the same boat, first and foremost, and this is the condition of our boat. So how do we fix it?  Do you want to keep going?

Are you going to jump out of the boat? And,  I believe, which doesn't mean everybody else needs to believe it, that folks,  you're so concerned about looking good. And I know that there's morale, but if you're in a tough place, even if you're in a great place, the specifics help others understand the decisions .

You got to understand the drivers. You got to move it forward. So a great invitation to our listeners to increase their transparency. If that's your leadership style, to support people just having aligned outcomes and  activities.

Claire, as we wrap up our conversation today, anything else you want to share with folks about what's on your mind?

What you're interested in? What's challenging you right now? Anything else you want to share?

Claire: Oh gosh, what's on my mind? The economy is so confusing! Industries are all working in very different ways. Technology stocks are doing great. People are getting fired. It doesn't make sense. And, you know, technology is my specialty. Trying to make sense of that is really where I'm focused now.

But if I want to leave anyone with any kind of perspective, it's that you gotta think outside of the box if you're going to change the way your business is headed.

A lot of times, we run across people who just say certain things are immutable. Every line in the P&L is hard to adjust.  There's businesses out there that can help you solve each of those specific challenges. We focus on cloud hosting. There's others out there focusing on others.

All of these problems are solvable. Nothing is just something you're stuck with.

Anthony: Sweet. I love that. I think the world has a lot of problems. So I take solace, hopefully, that it's solvable. It's just, can we solve them before the money runs out or anything else runs out?

Claire, it's been a pleasure. Thanks for the fun chat a bit of everywhere, but we got it, you know, grounded in the middle, but thank you for your time today.

It's been really, really fun.

Claire: Likewise, take care.

Anthony: Folks. One of the things I'm taking away from today's chat is, I mean, transparency, if it makes sense, helping align incentives, decision making, and make sure that your team can think about those build or buy decisions long term so that they can make the best decision and reinvest the business.

The other thing to consider is like what stage of your business. Are you in, are you in the growth? Are you in the kind of wrapping up? Are you in the cash cycle and then continuously looking at ways to innovate from a product? You can always do something that will solve a new or different problem. And I think that that really speaks to the need for innovation.

So balancing long term thinking and short term thinking. But thanks for being here. Thanks for watching. Claire, thank you again. It was super fun. I had a blast. Uh, folks share this podcast with somebody, you know, share it with somebody you don't know. That'll be even funner. Uh, but I hope you enjoyed today and I appreciate you listening.

See you next time.

Thanks for listening to today's episode of the Strategy and Leadership Podcast. Be sure to subscribe so you don't miss a single episode.  And if you enjoyed today's episode, please consider giving us a review. We appreciate you listening and following along, and we hope you have a wonderful rest of the day.

And as Anthony says, until next time.

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