This week on the Full Stack Leader we’re talking to Ryan Lee of Nautical Commerce!

Ryan Lee is the Founder & CEO of Nautical Commerce, the multi-vendor marketplace platform. Ryan has an extensive background in payments, logistics, and commerce. He launched Apple Pay internationally, was an exec at Visa, and lead product at a fintech before founding Nautical. Ryan is skilled at developing and driving a full-stack cloud technology vision and strategy to increase revenues, grow the client base, and achieve efficiencies in a collaborative results-oriented way. His company, Nautical, enables companies to do just that using its multi-vendor marketplace technology.

Ryan’s Top Leadership Tips:

Below is a summary of the Top 5 Leadership tips shared during the interview this week. Take a listen to the episode to learn more about the thoughts behind these tips.

  1. Teach Yourself To Be A Great Boss
  2. Know Your Guardrail
  3. Become A Great Interviewer
  4. Be A Life Long Learner
  5. Be Absolutely Passionate

We hope you enjoy the episode. You can find even more Full Stack Leader episodes here:


Show Transcript

Ryan Williams: Hello everyone. And welcome to this week’s episode of the full stack leader podcast. This week. I’m excited to be here with Ryan Lee. He’s the founder and CEO at nautical commerce. Ryan. It’s great to have you here. It’s pleasure. 

Ryan Lee: Absolute pleasure as well, Ryan, thank you for having me. 

Ryan Williams: Awesome. So maybe we can start out with you giving us a little perspective of how you got to this moment in time, where where’d you start in your career and what have you built up through?

Ryan Lee: Yeah. I mean, technically I started, as most what I would say technologists do is they jump in to an organization as a software engineer. So, started with ADT. In a professional sense, but you know, I’d say. My love for computers really kind of started early, early days.

Right? Second grade I knew immediately it was something I wanted to do when my teacher showed us the first Macintosh too. And there was a little game that had this dragon on the screen. And back then, if you remember all screens were green. So it was a green dragon. And I asked for how’d, they get the dragon into the computer and she said, they wrote it.

 and I could write software. My entire family were hands on like construction workers or mechanics, or, pipe fitters. And I was horrible at hardware. So the minute she said, all you had to do is write, I was sold. 

Ryan Williams: I’m in on that one. Yeah, absolutely. 

Ryan Lee: Exactly. 

Ryan Williams: Do you remember the Mac?

I assume the first one you’re talking about is that kind of tower Mac with that green screen at the top of the tower. And really, it was one of the first introductions to the mouse as well. I believe. 

Ryan Lee: It was precisely that. And yeah, like I said I fell in love after that. The minute I knew I could do something, I was like, wow, I can do that.

Ryan Williams: Did you start playing with it as a child and practicing with it. 

Ryan Lee: I did. And my obsession followed me obviously into my teenage years where there were circumstances where I had to work full time during high school. And so, I had secured a job with Avis rent car working midnight shift cleaning buses for them.

And the manager, the night shift manager, more or less said, Hey, look, I know you’re in high school. I’m gonna give you, three hours of homework, time and night to keep up with your schoolwork. So you don’t, lose traction there. And I was fortunate enough that I did not have a lot of homework.

So I went out and I bought a brick of a compact laptop back in the early nineties and that’s, and I taught myself how to code I bought probably $10,000 a year in books from a Barnes and noble To teach myself how to develop software. And that was really where I cut my teeth in learning the profession.

Ryan Williams: Wasn’t it such a different day when you really had to go through those software books and really translate like practice code directly from the page into some kind of an editor. And versus now you can, jump onto stack overflow and engage with things and learn so much faster that way.

But that, that must have been quite an experience taking it from those books into the computer. 

Ryan Lee: Oh, it was and building solutions without, I mean, yeah, the internet existed, but right there just wasn’t documentation. Like there is now, right. You run into a problem, you type the error into Google now and it solves problem for you back then, you spent hours trying to figure out how to resolve small errors.

Ryan Williams: Yeah. And I guess that kind of is in some ways helpful later on in your career, probably really annoying at the time compared to what you can do now, but you have to solve things. You’re not left with a like, oh, I can get these answers so fast. You never really learn it. It’s an interesting part of the, I think the past generation of computer science.


Ryan Lee: absolutely. And to that point, it was interesting because I met a lot of professionals while I was at Avis rental car. And that’s ultimately how I got my job at ADT security was, I met a professional that, worked there. I think he was a SVP or a director or something.

And he ended up recruiting me to ADT almost site unseen, which is like, oh, you write code? Yeah, we need you. Why don’t you come work to me? And so the next day I interviewed and they offered the job on the spot. And so, yeah that’s kind of how it all began, what 

Ryan Williams: a great start to the career.

So, so you worked at ADT for a while. Did you move up the ranks there or did you shift after that? 

Ryan Lee: No, I did. I think one of the first jobs that I had outside of automation was I worked for a very large contact center. Call center in, in other terms. Right. And we had a thousand employees we were doing a mass consolidation of I think, 15 different sites and we could not figure out how to get payroll to work.

 I think every two weeks we had a mass amount of call outs and it wasn’t from associates. It was from managers who didn’t wanna deal with paycheck issues. And so, I was tasked. Building a payroll system is one of my first first assignments, which, in, in software development, that’s pretty Herculean task.

Luckily, yeah, that’s pretty good. Yeah. We’re able to get it over the line. And there, there were many evolutions of that. We built the first one, which obviously solved paycheck problem. And the absenteeism of management went away pretty quickly once we implemented that.

But but subsequently we web enabled. And it’s funny because just last year I was told that, cause of the ultimate pro hack just to be ultra conservative, I believe ADT went back to my old 1998 payroll system, are you serious mitigate risk? And it still works. And so it’s powering thousands of employees, payroll still to this day.

And so it’s quite flattering to hear that it was still there as a contingency plan. 

Ryan Williams: Well, it’s interesting too, in today’s world. So many of those kind of classic business issues are solved by a ton of different third parties. So you have lots of competition for those various things, and still to know that you built something that powerful, that a major company like that would return back to it is pretty impressive.

Ryan Lee: Yeah. What never made sense to me Ryan was and maybe this was the innovator inside me. The rebel is at the time I kept on asking all of my leadership. It. Guys, we have something pretty amazing here. We should like sell this, 

Ryan Williams: On its own. 

Ryan Lee: And it was funny. It was almost like the railroad, the railroad never realized they were in the transportation business, otherwise we’d all be flying, , union Pacific airlines.

We would get delivery from union Pacific packages. ADT didn’t realize that they were in the information trafficking business, they thought, that they were in just the security business. And so, when I offered that up, I always was told we don’t do that.

We protect people we’re in the security business. 

Ryan Williams: And what a shift in just what 20 years in terms of how we view security and kind of really the threats of security, like they’re, the threats have shifted. I mean, in person threats are very real still, but like you like I think most people are concentrated on digital threats now and what’s happening with that.

So it is just security as a notion has shifted and you’re. Could be flying union Pacific versus just writing it. Yeah, it’s interesting. 

Ryan Lee: Exactly. Exactly. And I would say this, I’d be remiss if I didn’t call it out. ADTs actually become, the, one of the preeminent connected home providers and that makes me very proud that, they’re partnering with organizations like Google and all of these manufacturers that produce, this connected home because you. I worked there for 12 years, I believed in everything we did, we saved lives and we improved the human condition and I still believe they do that.

Ryan Williams: That’s amazing. That’s great. , so after ADT what was your next step? Where did you go? I know you’ve worked for some other amazing companies. Maybe tell us what was up. 

Ryan Lee: Yeah. After ADT I did a lot of digital transformations for them and I think that got me a lot of, no variety into the industry.

And so, the same gentleman who recruited to ADT called me to come work for him at visa. He was building a startup down in Miami for visa. It was a consolidation as well, and asked me to run. Three units for them. And there, I became a director and very much a technical focus.

So we were doing analytics insights. We were doing service support kind of think service desk, critical tier one support for network monitoring and stuff like that. And then strategic planning, really like where are our footprints gonna be? How do we staff the organization, who should do what, those kinds of decisions.

Ryan Williams: Yeah. Wow. Even just those two companies alone, like being with them during these periods where they’re transitioning into like really a new world of data and digital, like you just had such a great seat at the table at 

Ryan Lee: absolutely. And Ryan I would say that’s really, my unfair advantage is pre preparing myself at such a young age with technical skills and, beyond just what you learn in school, I think was a key ingredient to give me that seat at the table.

 You don’t just get a, see the table, you gotta earn it. You’ve gotta add value. And I would argue my unfair access. To those executives and more importantly, executive decision making. I think that’s the key thing that people just don’t get to see is the decisions and problems that get sat in front of these executives, these leaders, and then how they wrestle with them and how they make decisions.

And, achieving what I call that kind of decision efficiency. You don’t generally get that until later in your career. And I just had unfair access. 

Ryan Williams: I love that term DEC decision efficiency. It’s a really good term. And I think it is something that’s developed by leaders over the course of time.

 Because shining a light on that process of how people get to decisions is it’s something that’s really opaque in general. 

Ryan Lee: It is Ryan and it’s one of the hardest things to do because there’s no book, there’s no teaching that can prepare you for decision making.

 The decisions, the most critical decisions you make will hit you on a Tuesday afternoon, or And you have to rely on your past your experience, your intuition and and to an extent your. To make a decision and, you wanna make sure that, decision efficiency is not getting it right.

Every time it’s about making a decision that gives everybody a path forward in the absent of perfect information. 

Ryan Williams: What was one area that you had to use decision efficiency in your career during that period of time when you’re at visa or at ADT? Like where were you like really having to dig into those.

Ryan Lee: It’s interesting because and I’ll use visa as an example, we monitored the core network of visa, and so whenever there’s kind of outages or blips or something that’s impacting a client, you have to decide how far up the chain do you notify, right.

Who needs visibility to this? And, we had something that, that seemingly. Looked innocuous. Something that didn’t seem very important, but just by the way they described it, I felt like it needed to go as high as it could. And so, I made a decision on the fly of course, to, to notify the highest I guess, ranks of leadership there.

And immediately afterwards, I was questioned, I think by the leader saying, why’d you feel compelled to go all the way to the top? And it turns out a couple hours later, that was important because our largest client, which obviously was an issuer, raised the issue directly with the CEO and had he not have had visibility to it, would’ve literally just been like, I don’t know what you’re talking about.

And that’s not the way you want your CEO to be right. Working with your biggest client. And so, at one moment I’m. Chatted for it because it was like, that was unnecessary. But I stood by the decision and even if it wouldn’t have come out that, that way I still would’ve stood by that decision.

Because my gut told me that this was something that was eventually going to hit our key clients and, Someone needed to know. And then later lauded for how, oh you made a tough call and it kind of went that way. And so, it’s interesting you’ll find a variety of those types of decisions you’re gonna run across and you’ve gotta make those decisions.

I mean, I also, and I’ll give you another not so great story around this is. I was early, early in my career when ADT was owned by Tyco international and, mm-hmm, infamy of Tyco, in the Dennis Kowski days was that, there were obviously a lot of accounting irregularities.

And I remember specifically, this was obviously before any kinda investigation one of the senior vice presidents from that organization called. Because my organization controlled lot the reporting and asked me to change numbers. He didn’t like the revenue that was coming out and he explicitly said, Hey, I understand you controlled this report.

You need to change it, make it look like this. And it was funny because, as a technologist. My system just collects information. We don’t modify it, we don’t change it. And so I informed him that, Hey, you wanna change the information? You gotta go to the source system. We just, we compile.

And and it was funny because of course the threats came, this is a career limit move for you. You won’t move, you won’t go anywhere if you don’t do this for me. Of course I told him, he’s barking up the wrong tree and effectively in the most polite way possible told him to go fly a kite.

Then immediately called my boss and I told him what I had just done. And my boss was a speechless. He was actually quite concerned. He goes, you do understand who that is. I said, I do. I said, I don’t know it I’ll be here tomorrow. Good news is about a month later. All those issues with TA kind of blew open and it became quite public.

And so maybe that was, maybe I Dodge a bullet by uh, timing. But that sounds like it, that was a decision. That I stood by because of, ethics. It was the decision I stood by because it was the wrong thing to do. And as a young 20 something, I think I was 22 or 23 when the gentleman asked me to do that this guy that I knew had made millions and millions of dollars paid by the company was literally telling me to, to change numbers.

I just realized, I said, look, this is not something you do. And he needs to go ask someone else to do that. So, I think managerial courage is absolutely something you need to develop early in your career. 

Ryan Williams: Yeah. And I think especially ,, especially in the world that you tend to work in, which is payment systems and financial management and stuff like that.

It’s great to hear ethics is that the first and foremost of your values and what’s important to you. So it’s, it’s great to hear that. And I think very important for everyone in our industry, but especially in these pieces, 

Ryan Lee: yeah it’s gotta be a core part of your guardrail.

Ryan Williams: And on that front, you moved later to apple pay. And I know you developed there in, in the mid 2010s. I was actually there around that same time period. And so I see that you moved to Cupertino and made a jump to the west coast at that point, right? 

Ryan Lee: Yeah. Yeah, it was interesting because on the heels of becoming a chief of staff at visa I guess there was a fork in the road because apple called and said, Hey we’re launching this payment product.

And we heard that, you’re kind of the guy and we really want to have you come in and help us launch this. And uh, I think. I got that unique opportunity because as a side project, while I was at visa I had built a mobile app across all three platforms. Believe it or not a game for my kids to play.

That’s amazing. Exactly. But as a. I guess side effect, a pleasant side effect is it ended up getting half a million downloads and it started making some crazy money. And and so, it was interesting because at the time apple was recruiting a bunch of the payment professionals from the various networks, whether it was American express or, visa, MasterCard and discover.

But. Nobody at these organizations really knew anything about mobile. And so the way they got my name of course, was in recruiting. Some of these professionals from the payment networks, they said, Hey, did, is there anybody at your former organization knows anything about mobile? And uh, my name kept on coming up.

Every time saying, oh yeah, we know this guy that built this app. He built it on iOS. He built it on Android. He built it on windows phone. You should call this guy and talk to him. And it was funny. I had never applied there. They just called me outta the blue and said, Hey, we heard you.

No payments, mobile. And so we need to talk to you. And that’s how I got unique opportunity. We 

Ryan Williams: heard about you, like you were like, whoa. Okay. Exactly. 

Ryan Lee: It was little weird at first I was like, wait, are they listening on my phone? 

Ryan Williams: It kind of reminds me of the experience of working there actually.

Yeah. You you, yeah, they just kind of know. Yeah. It’s pretty, pretty wild. Yeah. Great. So, and then it looks like you shifted more after that into a little bit of a product role at a couple different companies over the next little 

Ryan Lee: bit. Yeah. Again, another fork in the road in my career is, you know, Ryan, you could have retired at apple, I mean, just staying there for us, your life.

Right. And Many people do. Yeah, absolutely. And there’s great people there. I would say only you’d have to be half crazy to leave the company. And so that was kind of the fork in the road was I kind of was like, look, do I stay at apple and have a, amazing career here or. Am I not necessarily done really bringing big change to the world.

Like I said, when I was in second grade, I had this vision of myself that I was gonna be one of the great computer pioneers and I was gonna bring software to the world and so. There was a part of me internally that was fighting, saying, you can’t retire, here at apple, you’ve gotta go out, go get into a startup, do what you said, you were gonna do build something.

Right. And and so it was a contract I made with myself. And the in, inside Ryan was yelling at me saying Nope, this is not your destination. so I decided to take a massive pay. And I jumped into a startup and so I jumped into a startup called turbo where I became the general manager and head of all payment and FinTech products.

And it was interesting because turbo was an amazing company for me to join because I think I was employee number. Yeah. I was employee number 10. they were on the heels of getting a series a and and really needed a lot of leadership and structure.

They had product down product was pretty buttoned up there. The CEO was. Former Microsoft had built some pretty amazing products. And so, uh, you know, for me, it was interesting because the skillset I could bring was, the discipline around, building the customer success organization really putting some structure around payments and the compliance and all that stuff.

And so I spent two and a half years there really kind of building. Private B2B marketplaces and embedding financial products inside our software, which was transportation management. Really? It was all about building private marketplaces for these logistics companies 

Ryan Williams: which is I’m sure very helpful to learn at that point.

Ryan Lee: Absolutely. Absolutely. And at the time, being such early days, I took it upon myself to mentor all of the young professionals there. Right. So anybody who joined that, was either straight outta college or, on the heels of becoming management, know, I kind of took under my w and gave them a regimen of reading and preparing themselves for leadership because, I saw these folks as high potential.

And as a matter of fact, Two of those gentlemen joined me at nautical as my co-founders. So, so those those investments paid great dividends in my mind.

Ryan Williams: That sounds absolutely amazing. But as you shifted into that kind of ultimate. Area of nautical where you ended up and still continuing to work in the marketplaces, it looks like you made one more stop on your way there. And at Moto, correct? 

Ryan Lee: Yeah. So, so Moto was a really awesome step because it was more in line with.

My career, right. I’ve obviously been a payment geek my entire life and Moto really embodied that. And so I got this really awesome opportunity to be the chief product officer over there which there, there were two really good side effects of that particular company is one. I got, board.

Access where, I got to sit in on all board meetings. So that was pretty amazing. And so, I would say that’s where I kind of cut my teeth in managing boards and working with board members. Two is they really needed assistance on sales side. , I kind of became probably a defacto solution engineer beyond just the product leader, the chief product officer over there.

And So it was interesting because I got to talk to 35 different fortune five hundreds. And at Moto, we were building what was called a payment orchestration layer which effectively let the, Mo the biggest of the big power, their complicated payment stacks. But what I found is that, Our offering also did a great job at powering marketplaces.

And so of these 35 fortune five hundreds, 30 of them all told me the same thing and they said, well, we need your payment And it was interesting because I’m sitting across the table from all these CSU folks, chief technology officer CIO, CFOs a lot of them.

And on occasion, the CEO and, I’m tech curious. So I kind of wanna understand why, what are you using us with and all that other good stuff. And this is kind of where I stumbled on the idea of nautical because, they kept on telling me there’s no platform out there to power turnkey marketplaces.

You have to build. And you have to take a commerce system and you have to highly modify it. And, I just thought that was unfathomable, that we’re in the 2020s and you’re still having to build stuff from the ground. It should have been a commodity. And once I did my own diligence, I realized they were right.

Even the incumbents were a two to three year build. And uh, so I I called those two gentlemen that I had mentored back in the turbo days and asked them and a couple others to, come to what I’d call a founder summit in early January of 2020. And uh, we just more or less sat down and said, Hey, is this something we wanna pursue?

And. And it was funny because I heard the description was, this is crazy. This is too big. It’s not possible. And all those things excited me on the challenge ahead and low and behold, this is where we’re at series a 30 million. And it turns out that a lot of people need the problem we thought existed.

Ryan Williams: so this is an excellent example to me of. The generation or the birth of leadership in its like kind of purest form, which is you had a history of a variety of different pieces of knowledge that came together, working at a combination of large companies and startups and all kinds of different facets even a game that you built on your own, right?

For your family and all these things, they come together and there is a synthesis within there that. I can feel like how driven you are towards that specific synthesis and like how it naturally leads to the foundation of something big. So I, I wanted to point that out. It’s an important thing for our listeners to note that this felt like a very natural arising experience versus something that’s kind of 

Ryan Lee: forced.

A absolutely. And I wouldn’t characterize, my career or path as particularly architected as much as its. Purposefully guided, right? Yes, that’s correct. That’s a great, yeah. Great description because architecting, I think is forced, whereas guided is you’re gonna go, you’re gonna go in a variety of different places.

But you kind of have to stay true to, where your end game is. There were plenty of jobs that could’ve taken that would’ve paid me a lot more money. If I would’ve in my mind short cut. And attempted to, pursue that instead of, what I characterized as my dream, which was really kind of to run a startup organization and software company that could bring, wonderful software to the world.

But I would also say that this is the culmination of, three different facets of my career, that in the beginning, , I didn’t intentionally go down that path. Right. We like to say nautical operates at the intersection of commerce, FinTech, and logistics and, if you kind of think about it, that was my career right.

In the early days of 18. I was cutting my teeth in a lot of FinTech stuff and then eventually got into the commerce aspects of ADT, helping them with account management, billing, and all that other good stuff. I probably built one of the first tele telephonic credit card machines because we had a lot of telephone orders and bill pay options.

And. Ultimately got into FinTech of course, got very deep there with visa and apple and the Moto and my time at turtle really deeply seated the the logistics part hard place. Yeah, exactly. And and so it was very fascinating that, this is really culmination of those three career facets.

That came together in, in. Serendipitous way, if you will. 

Ryan Williams: Yeah. And I’m actually really passionately driven by this subject myself, because I have also gone through a variety of different experiences throughout my career that have led me into positions of leadership now and where I synthesize these things and bring them together.

So there is a there is kind of a deeper knowing in having experienced those things and having built those things. To where, when you actually are leading people it kind of goes back to that point you made earlier about the efficiency of the whole thing, it allows for really pure efficiency.

So people can move quickly with you. 

Ryan Lee: Exactly. Yeah. 

Ryan Williams: What is a moment while you’ve been building nautical and gotten up to this point? What are one or two moments that were really impactful for you in some of your decision making to get where you’re at now?

Ryan Lee: I think what’s made me successful as a technology professional is I’ve almost always felt in my element when I embed myself into my customer’s environment and this isn’t, this isn’t me going and talking to a CSU person. I actually wanna sit. On the ground floor and watch, the person who’s gonna be using my software, understand their pain points because the key is if you can solve their pain points, right, you can elevate to that 20,000 foot view and explain to the, their boss, the C-suite person, whether it’s a CFO or CEO or CTO, why you’re saving them a ton of money because you’ve effectively allowed them to scale their.

Without linearly having to add headcount, because the problem is when tech fails, there’s a propensity in business to just throw bodies at it. And bodies are fixed expenses that right wrong or different are very hard to offload. I mean, nobody likes to fire anybody. I mean, if you’re a leader, that’s the worst thing you can do.

And it’s not only an indictment on you cause I mean, technically you hired them. but it’s also you. To an extent it’s something that, it’s a challenge or an opportunity missed, because I love coaching professionals and helping them, get to new levels of of capability.

 It was interesting because we spent probably a year and a half building the system somewhat blind, right.

Just based on intuition and our experience across commerce, spin tech and logistics. And so when we first went to market and started talking to these customers we expected. That we would get to, maybe 12 customers and a very specific revenue target within a year of going to market.

It turns out that, our story and our obsession with that user experience resonated so well that we ended up hitting that within the first quarter. And that moment was so seminal for me because it meant that we did the right thing, that we were so customer obsessed. And that, the economic value that we created for the customer was real and we solved a real problem.

And you kind of wanna know that sooner rather than later. And there was always this doubt internally and potentially externally whether it’s with investors or other people that are kind of giving you advice on the sidelines, Did you build the right thing?

Did you build too much, does it really solve the problem? and that moment when we just started making real traction and having customers just come outta the woodwork and prospects telling. Wow. You speak my language, you solve. My exact problem, was such a seminal moment for us that, we were just like, great.

We, we did the right thing. Let’s not rest our laurels of course, but yeah, that was so gratifying. 

Ryan Williams: That’s amazing. Do you think that when you had that realization and you started to see the data, come back that saying, Hey, this thing is right, that it allowed you to reset your expectations for everybody involved in building the project and kind of allow you to set everyone’s sites a little bit higher.

Ryan Lee: I, yeah, absolutely. I would argue that the shift went from, well, if we screwed it up we can always build our own marketplace with the tech we used, right. To, whoa, wait a minute. This is gonna become a platform. And that was not just internally, right? That was that was an investors and everybody else.

And one of the reasons why in this environment, I think we were able to secure such a large series a was because of the conviction Not just internally but by the customers, the, how it was resonating with the market really struck a chord, I think with a variety of investors out there that we were talking to.

Ryan Williams: How does that translate into the people that have been helping you build it? Do they feel excited and really refresh and engaged? Is that a is it give them that like kind of second win to power through the next phase? 

Ryan Lee: Yeah, we uh, we do have a culture of celebration, right. Internally.

Awesome. Uh, Yeah, that’s great. We we definitely realize that, software is, is built by people it’s used by people uh, and it’s powered by people. And so, one thing that, that is critically important in software for me, Is, you have to take a people first approach in order to get the technology.

Right. And what we did was, along the way we continued to communicate and we over indexed for communication probably In a very transparent way, more so than I think any company has really kind of done. So with even startups with their employees so that they can understand the journey and the value of what they were creating.

Whether it was product. Team marketing or engineering didn’t really matter. We wanted to make sure everybody in the team could say the same thing about what we were doing at nautical and what our mission was. Right. And I think having that unilateral alignment and having everybody fundamentally believe what we were doing was the right thing really shows in the quality of the product that, that we put out there.

Ryan Williams: All right. That’s amazing. I think that’s a, great wrap up and look at like how everything culminated into a very powerful building experience that you’re just about to jettison into the next big phase of, of the platform. And congratulations. We’re really excited to see what happens.

Ryan Lee: Absolutely. Thank you, Ryan. 

Break One 

Ryan Williams: Ryan reminds us that when we embed ourselves in the customer environment, we draw on inspiration that leads to usable innovation. He comes from a strong background in team building product and program management, business development, and innovation.

More importantly, this background helped him spot key holes in the market and a huge opportunity to fill. One of the keys to building a great marketplace is making sure the dynamics of all sides are thoughtful and supportive and to build a platform that supports many marketplaces is a Testament to the passion of connection that drives his leadership.


All right. Welcome back everyone. I am here with Ryan Lee and we’re excited to run through his top five leadership tips today. All right, Ryan, let’s start with number one. What do you got? 

Tip One (Teach Yourself How To Be A Great Boss)

Ryan Lee: It’s interesting. When I became a first time manager in tech I’ve been a manager before but in tech specifically, , I felt like I didn’t know what I was doing.

And I think everybody kind of goes through that metamorphosis. When you’re a great individual contributor, you have to kind of change your paradigm. Not everybody’s gonna do everything you do. And they’re not gonna do it, how you do it. Right. I like to say in product. The product team generally focuses on the, what the engineering is, the how, when you’re a manager, it’s pretty much the same thing.

Right? You focus on the, what your team really ought to do the how. And so, what I generally do my, my first tip is teach yourself how to be a great boss. And that’s a hard thing to do. I hate saying the word boss, but there’s a great book out there called how to be a great boss by Jeffrey J.

Fox that I read early on. And I’m telling you the guy wrote it in a genius way. Someone like me can read it very easily. He makes a single statement, defends it with a paragraph and NES tips for how to be a great boss. And I’ll tell you. That’s gonna pay massive dividends because, if you can engender employee engagement and empowerment people will just output the highest quality work of their lives.

They’ll do their lives best work with you as their leader. And and so, that’s tip number one is become a great boss, 

Ryan Williams: the foundational tip and really appreciate it. And I really like the simplicity of it. Cause I think it captures. The underlying quality of like how you harness the power of the people that are with you.

Not even just working for you because I think that’s sometimes what boss connotates, but that are actually with you on the journey. It’s really powerful. Exactly. Exactly. 

Ryan Lee: Yeah. Yep. 

Ryan Williams: All right. All right. How about tip number two? Tip 

Tip Two (Know Your Guardrail) 

Ryan Lee: number two is know your guardrails. Again, another book by Jeffrey J.

Fox love that guy. You’re a fan. Yeah, that’s good. How to be a C and it’s like 80 different or 85 different tips that he gives you on guardrails and unspoken rules that will keep you on the straight narrow, things like. Always understand the expense policy of the organization you work in.

Right. You wouldn’t think that was very important, but when you become a manager and you start approving people’s expenses, the fastest way to lose your job is to mess with finances and to approve something that you did have the delegation authority to approve. And so in my mind, it’s incumbent on every new leader to understand their guardrail.

I recommend how to be a CEO as a book to start because that, that in my mind helps prepare you for for the potential landmines. You could step on your journey to a Csuite leader. 

Ryan Williams: Great tip. Yeah the concept of guardrails is a really valuable one because we have guardrails not only internally, but externally with customers or with the way that we present the organizations, things like that.

It’s really a great 

Tip Three(Become A Great Interviewer)

Ryan Lee: concept. Absolutely. And tip number three in my mind become a great interview. I think everybody in believes that because they’ve been through an interview. They know how to interview. And in fact, I found that most people are terrible interviewers.

They actually interview for people they like, and what they’re biased towards, not for, what what engenders the right culture or the right role fit and things like that. Right. And I think the first time I kind of went through this challenge was when I went to visa and I had to hire 25 professionals across eight different roles.

I leaned into a technique called top grad. I modified it quite a bit from from what was there, but what I did was I looked for very specific traits across I think, eight or nine different dimensions from passion innovation grit. Polish in terms of how you speak leadership decision making and accountability and then ultimately their competency.

Right. I wanna understand how competent they were around their discipline. And so, when you can build a system. Around how you interview, you can weed out those natural inclinations for bias. And what that allowed me to do was to curate the most diverse team that visa had seen across that, that large of a team.

It was 20 odd professionals. And in addition, we hit a 92% employee engagement when the rest of the organization was in the mid like fifties. Wow. And so it was quite a feat. To to do that. And I would argue that was because I taught myself how to interview. And then I, of course taught all my leaders how to make sure that they used that technique to improve the way they interviewed.

We also consequently Ryan became a theater team for the rest of the organization for director roles. So I took people who started. Level one employees. And, uh, now there’s a gentleman in the product organization who’s, on the cusp of becoming a VP in less than 10 years. And so, for me that’s quite that speaks well to the technique.

Ryan Williams: And the recruitment team tried to hire you away. And you’re like, exactly. That’s amazing. It is like a very basic thing where you’re like, oh, I just need to get this person. But it is one of the most common subjects I hear is like, you really have to learn how to understand and read people and figure out the proficiencies and also their fit, the cultural fit.

It’s really 

Ryan Lee: Vital. It is exactly uh, I think Reed Hasting says nobody wants to work with a brilliant jerk. Right? You have to weed out folks that just aren’t gonna be a good culture fit, but might be just absolute rock stars at their profession. Unfortunately, sometimes you have to pass on those.

Ryan Williams: Yeah. And he also, he also talks about one of my most important things too, is hiring learners, people who are there to learn and grow. Yeah. Great. Alright. How about tip number four? 

Tip Four (Be A Life Long Learner)

Ryan Lee: Tip number four. Goes with what you just said. Is you’ve gotta be a lifelong learner. Ryan, I mean, in my mind what’s made me successful is I’ve been very passionate about what I do and I’ve made sure that I’ve learned as much as I can.

And so I always had this rubric, this rule that I always wanted to be two levels ahead. Of my current competency or role. And so, whether it was establishing executive presence or, learning something about, something very nuanced about the job that I was in, like at apple pay, obviously learning all about tokenization and, MB track records and stuff like that.

That would that would help make me invaluable in the organization. I would credit that. My passion for learning new things. And I hope that I never lose that because, I think that’s ultimately what keeps you young at heart. 

Ryan Williams: I think that’s a great take on it.

Learning, it does keep you really tied into the kind of heartbeat of what you’re doing. It’s it. And if you just tap into that, you have lots and lots of fuel for the future.

All right. Final tip number five. What do you got? 

Tip Five (Be Absolutely Passionate)

Ryan Lee: This one’s really important to me is you should.

Be absolutely passionate about what you do. Because at the end of the day, you won’t work a day in your life. I’m not gonna say it’s gonna be easy, but but you know, you really ought to strive to do something that you’re passionate about because, oh, if you are, you, aren’t gonna realize you’re working.

Which may not bode well in your domestic situation in some circumstances but I will say that, I’ve always been super passionate about my tech anybody who knows me, I always had some kind of side project where I was building some kind of widget or something in tech, partly because not only I wanted to learn, but because I absolutely loved how tech can change people’s lives.

And uh, and so, what I would say to anybody is. Follow your passion, not the money, because if you’re passionate about and you love it, you can be the absolute best and the money will follow. So, that is my final tip for all professionals. 

Ryan Williams: And I think we can all hear how passionate you are, and we’re really excited to see what you have coming here in the not too distant future with nautical commerce and how you’re gonna bring that passion to the next phase of growth for that.

It’s been a real pleasure to have you here today. We’re excited to see everything that’s coming up. And Ryan, thanks for being here. 

Ryan Lee: Thank you, Ryan. Really appreciate it.

Ryan Williams: Ryan gives us a solid perspective on what it means to be a great boss in his top five tips. He offers some depth around the most important. Finding the right fit. He suggests that being a knowledgeable interviewer and having a clear understanding of who to hire can make a huge difference in the lifetime management process of that team member.

More importantly, he offers the amazing perspective that knowing where to focus your energy will guide you ultimately to empowering your entire team the right way.