What The Unicorn Knows Conversation 1 of 2 @StudioA3R

Jennifer Sertl #a3r
9 min readOct 12, 2023

Matthew E. May is a distinguished six-time author, esteemed speaker, and currently holds the pivotal role of Senior Strategy Advisor at Insight Partners, a global venture capital and private equity firm renowned for investing in high-growth technology companies spearheading transformation in their respective industries.With a professional journey spanning over three decades, Matt has become a venerated figure in the realm of transformative strategy, innovation, and lean initiatives.His latest contribution co-authored with Pablo Dominguez , “What a Unicorn Knows: How Leading Entrepreneurs Use Lean Principles to Drive Sustainable Growth,” published in early 2023. He was gracious enough to speak to me on my podcast Studio A3R and I invited my Rochester Institute of Technology School of Individualized Studies’ students to both read the book and ask him questions. Here is the first of two installments of what we learned.

Jennifer Sertl: How did you meet Pablo Dominquez and how did What The Unicorn Knows come together?

Pablo and I have been working together since 2011, well over a decade. I first met him at a large organization called ADP. I had been brought in by someone else to do a one-and-a-half-day workshop with them. Initially, I didn’t even know Pablo was the boss; he was very quiet but clearly a leader in the room. It was only after the workshop that I realized he was in charge. He brought me in for a couple of other engagements, demonstrating a trust in my expertise.

Pablo later moved to a late-stage startup called AppNexus, an advertising tech company that competed with Google AdWords. It got bought while he was there, but not before we did some significant work together. Pablo has been the innovator behind taking lean thinking and applying it to the go-to-market world, especially sales and sales operations, a traditionally non-lean area. We made great headway together in this endeavor.

When AppNexus got bought, Pablo found his next opportunity at Insight Partners. He grew that organization from a two-person advisory group to over a hundred. Our partnership is akin to Bernie Taupin and Elton John — Bernie writes the words, and Elton writes the music. I consider myself to be the worst marketer and salesperson on the planet, so I needed an “Elton John” to my “Bernie Taupin.”

When I pitched the notion of a book and got a contract, I asked Pablo if he would be interested in partnering with me, with the understanding that he would handle the marketing end of things and keep me honest regarding the companies we covered. I did not want it to be an Insight Partners book — something Pablo agreed to after some consideration.

So, our partnership is a combination of “words and music.” I focus on the content, the “words,” if you will, and Pablo brings it to life, turning it into “music” that resonates with the audience. Our complementary skills have proven to be a powerful combination, contributing significantly to the success of our projects.

Student Question: Could you elaborate on what practical steps to establish espirit de corps in an organization?

It’s kind of funny; I just got back from three days in New York City with the company that I’m employed by, Insight Partners, and I’m in Los Angeles. Almost all the rest of the company is in the New York City area, although a lot of them are spread out. We very rarely get a chance to come together. One of the things that we did over the three days, because we have grown so fast, we needed to “eat our own cooking,” so to speak, when it comes to establishing some Esprit de Corps and teamwork, some comradery.We structured three days to do just that. It begins with values, personal values that then sort of come together in a group fashion, in a team fashion. The hardest part is making the connection between what you value as an individual and what the team values. If you don’t make that connection, for example, let’s say that you value balance, but you find yourself in a team or an organization or a job where you just can’t find that balance. You’re working 80-hour weeks and while you’re making lots of money and your career is advancing, you’re not sleeping all that well at night because something internally has you off balance. Sooner or later, you will deselect, meaning you’ll leave.The point where your values clash so much with what clearly the team values that you just can’t go on is a pivotal moment in one’s career and overall well-being. So, the best way that I know to build that kind of camaraderie and alignment in values is to ensure that at the individual level, you’re clear about what you truly value.

In the last chapter of What the Unicorn Knows (page 218) there is a very practical exercise called a “value sorter.” Spend some time with that. Take the 36 values that are kind of universal and figure out what you’re all about values-wise. If you even struggle with that exercise, take a look at your spending habits, your bank account, your credit cards, what you spend your money on, and then what you spend your time on. It’ll become very clear to you very quickly what you truly value, especially considering the time element.

Go through that value sorter and then do it as a team and make that connection. That’s a really practical way of aligning individual and team values. Back to that three-day meeting last week, that’s a good bit of what we did. Sharing stories that exhibit the values that we hold is another powerful exercise. It fosters understanding, connection, and ultimately, camaraderie amongst team members, propelling the organization towards success by ensuring everyone is aligned and moving in the same direction, fueled by shared values and objectives.

Student Question: when you’re trying to create a lean process, ensure you don’t make it too lean to the point it becomes detrimental?

The practical answer to this, and this is where I depart from traditional lean manufacturing or lean production as people have learned it in books or in school, is to do everything in a cross-functional way. Traditional lean, continuous improvement has you working in a natural team. You can simplify your processes, take the complexity and the complications out. But what it doesn’t do is inform you where the gaps in Process A meet Process B. What you’re talking about can actually happen quite frequently if you are not working cross-functionally.

In my work, which is all knowledge work — I work with technology companies, all B2B software — the unique aspect is that while we’re not working with a physical product, I always work with cross-functional teams. For instance, if it’s a sales team and we want to take 50% out of our sales cycle, I will still have in the room all the people that are involved in making a sale. That includes product people, engineering people, solutions engineers, marketers, lead generators, pre-sales people, salespeople, to post-sales people. In B2B software, there’s a thing called customer success, which comes into play during renewals and expansions of sales, onboarding, and implementation. I involve them in the lean process optimization effort.

This approach ensures that all various and assorted downstream or upstream touchpoints and potential breakage points are known in advance. Another crucial aspect is that when you do this, it’s always an experiment. It’s never about flipping the light switch and turning some new process on company-wide. Never. It’s always a very small, nested experiment that then gets iterated upon and potentially piloted as a broader solution or a standard. We constantly learn from those accelerating, escalating implementations. There’s always the after-action review, the validated learning part of it, so that we avoid potential break points and ensure the lean process is optimized without compromising the quality and effectiveness.

Student Question: Can you share which industry or company type is your favorite to work with when it comes to implementing lean processes, and why?

I don’t have the luxury of having a favorite; my preference tends to be whoever I’m working with at the moment and who is most engaged and experiencing the most success.

However, as a general category, I think the best way to answer that is not by naming a specific company but rather a sector. It has to be healthcare and health tech. For some reason, those that enter the healthcare, medical, med tech, health tech realms often come from the healthcare world and are now applying that knowledge in a technology delivery system. There is something unique about this sector; it’s not just about the money. There’s a humanitarian side to the work.

In healthcare and health tech, there is a more palpable feel whether we’re talking about strategy, process, or the customer experience — or in this context, the patient experience. The company I’m working with right now is all about clinical trials. They talk about people more than stuff. If you map out any process and look at it, stepping back, you may ask, “What’s missing?” In the white spaces of that map, there are actually people performing the steps you’ve mapped out.

In healthcare, there is a greater attention paid to those people, making the work in this sector more fulfilling. There’s a strong emphasis on the human element, not just the technical or procedural aspects. It’s about making real, tangible improvements in people’s lives, and that adds a layer of gratification and purpose to the work that I find particularly rewarding.

Student Question: In your experience, what, um, do you think there are any key strategies and mindsets businesses can adopt to foster a culture of continuous innovation?

The best way to answer this question is to give you an example from my career. I spent a good bit of time working with the Los Angeles Police Department when I was at Toyota and the University of Toyota. We wanted to decrease our costs to the overall organization because it was run as a cost center, and we aimed to develop an externally focused learning program.

One of the first organizations to come to Toyota to get better was the Los Angeles Police Department, which, at the time, was under a consent decree by the Justice Department. LAPD had a history of bad leadership and scandals, and like any military or paramilitary organization, it was resistant to change due to its clear chain of command.

Despite these challenges, we were able to effect change in LAPD by focusing on projects that were most important to the leaders and selecting those that wouldn’t turn the world upside down. We focused on incremental change, affected by people doing the work, aligning with the notion of lean process and continuous improvement.

I call it a clamshell approach — with air cover from leadership and ground troop effort. We didn’t begin with actual police officers but started where it would be least disruptive to LAPD’s overall operation. We worked with civilian workers running the jails in downtown Los Angeles.

The key is to pick projects that aren’t huge but focus on high leverage points where little changes can make a big difference. Start with one or two teams, work to improve a process with measurable results, and then organically spread to adjacent teams. In this way, in a few months, you have an organization continuously improving without some big program commanding, “let’s become continuous improvers.”

So, change, especially in resistant environments, is possible with a focused, incremental, and organic approach that is sensitive to the organizational culture and structure.

You can listen to the entire conversation on the StudioA3R Podcast. The second segment of this conversation will be released Thursday October 19th.

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Jennifer Sertl #a3r

Biz strategist fostering better decisions,systems thinking, scenario planning. Mind of chess player ♜ Heart of a poet ♫ Inviting depth ... @agility3r