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The Power of Transparency and Neurodiversity with Aimably CEO Claire Milligan

By Anthony Taylor - April 08, 2024

Nothing is immutable. Every line in the P&L is adaptable, and every challenge is surmountable.

In this episode, we have CEO of Aimably, Claire Miligan to discuss the strengths of neurodiversity and transparency in business. She shares her perspective on a culture of openness and the power of transparency in decision-making and empowering teams. She touches on the challenges of product management, shedding light on the process of balancing short-term goals with long-term innovation. Later on, Claire starts to reveal her secrets to quantifying the ROI of product improvements and the build versus buy dilemma. Tune in now!

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The Power of Transparency and Neurodiversity with Aimably CEO Claire Milligan

My guest in this episode is Claire Milligan, who is the CEO at Aimably. Claire, how is it going?

It's going great. How about you?

I am fantastic. I'm excited to have you on the show. You talked a little bit to me 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.

My name's 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 the Chief Product Officer and also, the 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 turn it into a cash cow so they could invest in other lines of business.

Together with what 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 to be able to reduce them and to turn that line of business around. I'm proud to say we did. I get 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 realized there was an opportunity to go out and create our own business so here we are now.


Graphics - EB - SALP Claire Milligan


The Leader’s Path To Success

How does the mind of a successful product owner think? Do you walk around all day looking at stuff and being, “That's wrong,” or, “I would do this better,” or internally, your gears are 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.

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. However for me, yes, I do evaluate everything as I go. I like to tell people that when I was a kid 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. Also, it should be so brain-numb that it should function.

A lot of people think about the outside of a car and I was thinking about the inside and how you use it. Yes, absolutely it’s all of those things. Thinking about how it can be tweaked and refined is what I spend a lot of my time on. You mentioned neurodiversity, but that's sometimes what I can spend too much of my time on because I can try to focus on solving those problems. However, when you're a founder, I suppose over-focusing and solving problems helps.

It is. You're supposed to get into a necessary amount of trouble as a founder. Looking at that, let's take your journey. You've gone from looking at products and solving problems. You are in the middle of this now, but let's focus on the product manager lens. You talked about the inside of the car. A lot of our readers, our CEOs could be product owners, if not in technology, some other thing. What are some of the questions that you ask yourself as you begin the product improvement process or problem-solving process? What are the steps you follow to try to figure out how you think, not that anybody needs to think that way?

I think it depends on the stage of business you're in. I've been in 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 and trying to get work done that they infuse with processes that they cannot solve any other way. When we're talking about software, it's like there have been umpteen solutions intended to create inbox zero, but people try to go after this vision that other people are trying to accomplish in their daily lives with clicks and buttons and all kinds of things.


Growth is all about finding avenues for the way people behave and try to get work done.


The novel opportunity for real growth and real product-led growth is to find things that take the most amount of people's time, condense them, and solve them for those people. Don't show them how it is. Solve that job. When it comes to a business that is much farther along, we're talking about making that product better. For me, I'm a huge believer in financial analysis. Whereas, there are plenty of product people out there who will say, “We have no idea how much 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. Also, 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.

I have these massive spreadsheets that I've lived and died by for companies and it's incredible how much your customers love it when you deliver for them what they're asking of you. However, 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 solve this in a way that's on brand and resolves the issue rather than just, ‘Put this button here?’”


Graphics - QuoteStyle - SALP Claire Milligan - Guest Square

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I think one of those questions that CEOs if they don't know whether they face it, is the build versus buy dilemma or don't build or don't buy. However, what I hear at the root of your thinking is the business case. It’s making sure that there's a business case and that's likely or almost certainly the thing that led to this new problem because they have a pain. 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.

Also, there's how you think and then how would you invite our leaders to encourage strategic thinking à la product manager within their organization? It’s 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 so they don't wholly own the solution or they don't think they own the solution. If you were in a seat and you wanted people to think more like business cases and challenge them to do the quantifiable things, how would they do that?


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


I think we as CEOs own the problem because we have our incentives and are 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 or whatever your compensation package is oriented towards. Ideally, your compensation package is aligned with what the company is trying to achieve next. 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. Whether or not it's stock options, whether or not it's extra compensation based on improvement, one of the things that we do is we consult with companies on trying to make sure that they reduce their cloud costs and sometimes it requires engineers to do the work. We say, “Set aside this chunk of money on money you're going to be saving. Give it directly to the people who do the work.” All of a sudden, lights go off and everyone's owning the problem.

I don't know why that was such an a-ha, but yes. I'm like, “But the money.” I think maybe potentially it's hard because you don't know what you're going to get out of it, but an example is stocks. We were super cheap a year ago and I'm like, “If I have put this money, earmarked for it, and I have strong confidence it'll get to 70% because it's on sale, why not put that 70% towards here?” 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 $250,000, why not carve off some of that into solving the problem?

Is it just me that's too stupidly clear? I don't mean it in a personal way, but it's like, “Duh,” but I guess some people don't think like that. People don't think of the ROI of a thing and the cost-benefit analysis. 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? It’s because I imagine 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, “Why don't you see this?”

Yes, on that side, certainly in thinking about what we should invest and spend in. If I show how the incentives are aligned, I've always gotten a lot farther, but I'm going to say the hardest part of our contract to negotiate is the set-aside savings for the engineers doing the work. You would think it's braindead because we have calculated how much it's going to go and there's this reaction of, “People shouldn't be compensated like that. Why should we set that much money aside for compensation?”

My response essentially is, “We do it for sales.” Compensation for commission-based is always out there. It’s always on the growth side. Even some marketing teams are compensated that way and 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.

How would you say that compares to other technology companies? It’s because I know a full stack developer could cost you. $250,000 is cheap, but some of those folks who are core to the product and product engineering in tech specifically are getting compensated well. Would you say that either that's consistent in tech and should be done across all other functions?

It's a challenge. It’s a supply and demand question. What's interesting is that people always go to the next step and they say, “They're compensated so much. Wouldn't it be greedy to compensate them more?” I say, “It's like on-target earnings for salespeople.” If you make the on-target earnings, it’s totally achievable, but in line with the goals of the company, it makes sense to do that. However, this is the next point I like to talk about right now, 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.


It could be that 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 are these couturiers who are constantly building their own code like sewing this beautiful dress in Paris for the runway every single time, but this is for every single technology business. Yet at the same time, you can buy these looks from H&M, Zara, or whatever low-budget brand, but nobody knows how to develop code in these models where the focus is there's a bit of design, but then there's a whole lot of value engineering into how do we run this at scale? I think that's the next step for technology but we're nowhere near that yet.

The Next Step Forward

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 in barrier to entry for having high-value technology infrastructure will support folks like small to medium enterprises, which will then disrupt the industry which is great for you, especially if people are using more cloud computing solutions.

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

I think it comes down to, “Does the technology advance your business meaningfully?” The bitcoin mining, there's an environmental impact to it. There's a conversation in the stock market about what is the true asset value. Is there some kind of gold standard on Bitcoin? There are a whole lot of ways that you can 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.

It's hard to give you a clear yay or nay on it but at the same time, I think the take-home question is, “Is it worth it to us from a financial perspective to go about doing this technology piece 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 going out and writing their own code as you were 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 is if you're just paying the subscription fee that's taking care of beyond your doors. You'll have to think about how you evolved 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. It’s because the other point is you don't ever have growth when your own client is yourself.

It’s interesting to go down to thinking like, “What is your company as a product?” All these entrants come in. The competition for all businesses becomes more fierce and the layer of integration between technology or not technology is ultimately what differentiates businesses when it gets harder and harder to differentiate. That's not how I thought our conversation was going to go but it's super fun. An open-ended question I guess I could ask around leadership people is what are your driving principles as you think about growing a business or building a team?

I think it's all about transparency. I think the word is overused though. Transparency and education work hand in hand. If you're trying to go somewhere and if you have a goal for the business, a lot of times leaders will say, “I don't want 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. Make sure nobody knows.”

You have to start from the fundamentals of people doing what you want them to do when they understand the full picture. If the company is starting down a restructuring process, you start with making sure you explain what the financial realities are and looking for help and adjusting that. There's a particular example 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 well-paid engineers doing the growth business and we didn't have that capability to move forward.

These were people I'd worked with for years and I was being asked to be essentially the executioner. “Go in and look at the problem. Solve it as many ways as I could and find the right way.” I laid it out to the team. We were like, “These were our finances. We looked at the P&L together, every single one of us, and we were like, “How can we arrange this? How can we work with this,” knowing the constraints of how the business operated.

When it then became very clear that we were going to have to do layoffs, I asked people whether or not they wanted to stay knowing fully 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. Hopefully, people respect you for it and they move on and find growth elsewhere if it's that kind of scenario I was talking about. However, it's all about everybody rowing in the same direction and then building those incentives behind it.

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I can imagine that was a challenging thing to do, but I think you talked about everybody rowing in the same direction. I think that was a great demonstration of, “We're in the same boat, first and foremost, and this is the condition of our boat. How do we fix it? Do you want to keep going? Are you going to jump out of the boat?” The folks are so concerned about looking good and I know that there's morale, but if you're in a tough place or even if you're in a great place, the specifics help others understand the decisions and you talked everything about that aligned decision making.

You got to understand the drivers. You have to move it forward. It’s a great invitation to our readers to increase their transparency, if that's your leadership style and to support people having aligned outcomes and loan activities. Claire, as we wrap up our conversation, is there anything else you want to share with folks about what's on your mind, what you're interested in, and what's challenging you right now?

What's on my mind? The economy is so confusing. You think about where we need to go and these industries are all working in very different ways. Technology stocks are doing great. People are getting fired. It doesn't make sense and technology is my specialty, but I think that trying to make sense of that is where I'm focused now. However, if I want to leave anyone with any kind of perspective, it's that you have to think outside of the box if you're going to change the way your business is headed.

A lot of times at least, we run across people who say certain things are immutable. Every line in the P&L is hard to adjust and there are businesses out there that can help you solve each of those specific challenges. We focus on cloud hosting. There are others out there focusing on others and all of these problems are solvable. Nothing is something you're stuck with.

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, where can people learn more about Aimably? Where can they connect with you and chat if they want?

We're at Aimably.com, and I'm on most social networks with the handle @Claire_Designs.

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

Likewise. Take care.


Strategy and Leadership Podcast | Claire Milligan |  Neurodiversity


Folks, one of the things I'm taking away from this episode is transparency. If it makes sense, help align incentives and decision-making. Also, make sure that your team can think about those builds or buy decisions long-term so that they can make the best decision and reinvest in the business. The other thing to consider is what stage of your business are you in. Are you in the growth? Are you in the wrapping up? Are you in the cash cycle? Also, 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 it speaks to the need for innovation. It’s balancing long-term thinking and short-term thinking. Thanks for being here. Thanks for watching. Claire, thank you again. It was super fun. I had a blast. Folks, share this podcast with somebody you know. Share it with somebody you don't know. That'll be even more fun but I hope you enjoyed this and I appreciate you reading. See you next time.


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About Claire Milligan

Graphics - Claire Milligan Headshot - SALP Claire MilliganWhether she’s helping businesses transform their cloud spending or hitting the slopes as a ski patroller, Claire thrives on distilling complex problems down to their core issues — and turning these pragmatic findings into groundbreaking solutions. Through a journey spanning marketing, UX, and leadership roles at tech companies like Tallie and SpringAhead, she’s meticulously constructed a diverse skill set built upon hands-on expertise and an unrelenting thirst for knowledge. Now, as the CEO of startup Aimably, she’s applying her unique superpowers to help businesses grow by spending smarter and dramatically reducing their cloud costs.

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