Innovation and the Digital Enterprise · 2025-05-08 · 17 min
Patrick Emmons curates perspectives from five technology leaders - Fred Lee (CTO at PartSource), Dan Kirsch (CTO at Chamberlain), Jory Sachs (head of United Airlines Innovation Lab), Steve Cottle (former CTO at Rand McNally), Christina Garcia (SVP of Engineering at AH Echo Logistics), and Dom Scandarino (CTO at Cameo) - on the fundamentals of team leadership. The common thread across these conversations centers on prioritizing talent acquisition and development as the North Star of any technology leader's strategy. Fred Lee articulates this directly: building a world-class team capable of repeatedly delivering world-class products matters more than specific product or technology vision.
The leaders discuss practical team-building principles including assembling diverse talent across age, background, and experience levels; fostering a culture of psychological safety and knowledge sharing; creating structure and metrics for innovation without stifling flexibility; and deliberately understanding individual team members' strengths, motivations, and communication styles. Christina Garcia emphasizes stretch opportunities and one-on-one relationships as growth mechanisms, while Jory Sachs highlights how cross-functional pairing of complementary personalities - balancers against innovators - creates magnetic teams. The compilation underscores that scaling teams requires intentional process evolution as headcount grows, and that leader visibility, accountability, and genuine interest in people's personal goals directly influences team performance and retention.
Fred Lee argues the primary goal should be building a world-class team capable of repeatedly delivering world-class products, not the product or technology vision itself, because a great team will overcome any challenge and adapt to any circumstance.
Christina Garcia's primary method is giving stretch opportunities - assignments slightly beyond current capability - paired with active support and one-on-one coaching tailored to the individual's current skill level, which accelerates career growth far more than formal training alone.
Dan Kirsch explains that processes effective for three engineers don't work for 100 engineers across ten teams, and leaders must intentionally reassess and adjust procedures for efficiency and to prevent siloed work, even when current metrics look good.
Fred Lee found that when engineers listen to customer service, they build empathy for end users, discover how their product helps and hinders, improve team morale through human connection, and return with greater energy aligned to company mission.
Jory Sachs argues you need both extremes - innovators thinking outside the box and operationalists focused on scalability - working together, not siloed, because neither alone can create sustainable innovation; structure and metrics are necessary but must allow flexibility.
Computed from the transcript - who did the talking, and the words that came up most.
In this compilation episode, we look back on wisdom from renowned tech executives about how to build and foster great teams. Featuring insights from Fred Lee, Dan Kirsche, Jorie Sax, Steve Caudill, Christina Garcia, and Dom Scandinaro, who share their perspectives on the importance of diverse and well-structured teams. Key topics include team composition, sharing knowledge, effective scaling, fostering interpersonal relationships, and creating rich organizational culture. These leaders emphasize the significance of nurturing talent and fostering diversity to build world-class teams capable of overcoming challenges and driving innovation.
Transcribed and scored by The B2B Podcast Index.
Speaker A: Foreign.
Speaker B: Patrick Emmons. Here in this episode, we're bringing you a special collection of insights from some of our past guests, all centered around a key theme, what it takes to lead great teams. Across these conversations, a common thread emerged. Successful leaders prioritize building strong, diverse and well structured teams. You'll hear from industry leaders like Fred Lee, Dan Kirsch, Jory Sachs, Steve Kuddle and Christina Garcia as they share their perspectives on what makes a great team and how to cultivate one. We'll kick things off with Fred Lee, CTO at PartSource, who emphasizes why team is the North Star. Build a great team and everything else will follow, he says. Next, we'll dive into team composition and diversity, featuring insights from Dan Kirsch, newly promoted CTO at Chamberlain, also Jory Sachs, head of United Airlines Innovation Lab, and Steve Cottle, former cto at Rand McNally. Later in this episode, we'll explore sharing knowledge and creating team structures with Christina Garcia. She's the SVP of Engineering at AH Echo Logistics, and Joy Sachs of United Airlines. We'll also hear from Dom Scandarino, CTO at Cameo, Dan Kirsch again and Jory Sachs on how to grow and scale teams effectively. Finally, we'll discuss the importance of knowing your people and fostering strong interpersonal relationships with insights from Christina, Fred and Dan. So let's dive in.
Speaker A: For me personally, who you know, I lead technology and product and engineering. You know, it is always about talent. It is not only hiring but also growing the great talent that I already have and just constantly trying to improve the team. A lot of times people will ask me like Fred, what is your vision? What is your mission while you're there? And people might be a little surprised to hear me say that my goal is to build a world class team that can build world class products over and over again. And that's maybe a little surprising to people because they expect to hear from me something like about the product or about the technology or whatever. But what I have learned is that the only thing that really matters is do you have a great team? And a great team will overcome any of those things and a great team will adapt to any of those challenges.
Speaker C: I m think you want to find people that kind of round you out, but also that you're going to enjoy working with. So huge, huge piece to it. I want somebody who's passionate, I want them to have an opinion right when I ask questions, to really have some sort of thoughtful position behind it. It doesn't have to be the same thing that the way I think about it, but I want them to be thoughtful and opinionated. I want them to be innovative.
Speaker D: No solid ideation comes from one individual. And that's where that inclusion comes into play and that diversity of thought background comes into play. So I would say that ultimately in innovation it is much more about the culture that you're creating, the fact that you're all united behind a shared passion and purpose. So there is a sense of sharing and you can't just hand something over. There does have to be communication and collaboration at certain point. It's just not a siloed handoff.
Speaker A: From my perspective, the best thing to do is get a lot of diversity, right? You want to young talent, you want non traditional educations, you want folks that came from different places, you want old school guys that been there and done that and bring all of those folks together gets you just um, a lot more interesting team. And so then when somebody comes in to interview, you know, assuming you can get them to at least take your call, the folks that they're talking to is a wide assortment of people with a bunch of different perspectives. And not just okay, everybody's got to be a cookie cutter. And you have to fit in a certain way foreign,
Speaker E: communicate out to all of your peers in EORG the lessons you learned so that someone else can avoid that in the future. Because things do fail. We're human, we're imperfect. But as long as we're able to change the way we work to mitigate that and learn from those mistakes and bring that forward across everything and share that those learnings, those lessons the better. So some of the hurdles is you know, trying to go too fast because you help it and not having spent, spent the time on the why silos of communication. When those failures happen, the team solves it, but they're not then taking the time to let the rest of uh, the org know to learn and share from those lessons because they're valuable. Even if that MQ failure was specific to that one incident, like the replications of it or like the pattern of why it failed could be very applicable to other things. So really take that to heart. And I think the other things is just also being clear and holding accountability. What you allow to manifest in your org is seen as okay, that's the bar as we, you know, we talked about earlier. And if your bar is no, we want quality and done means this and then holding people accountable at that like that becomes the de facto standard for great and good and done in your solutions.
Speaker D: You want enough structure and framework so that the way you're operating is consistent. You're able to assign value metrics or return metrics on, you know, the time spent by a team or the dollar spent. There are ways to create structure within innovation, and I think it's absolutely necessary and needed. It's just a matter of where do you add structure, being thoughtful about it, how do you create structure that still allows for flexibility, spontaneity. And I think as long as you have the right, I would say intake, funnel prioritization and kind of scope of where you are going to innovate and on what, and you have processes in place for those types of handoffs. If it's something that you're building within a team or you're conceiving in a team and is not going to scale within that same team, you're going to need some form of process for that. And then ultimately metrics to show that you're growing. Because if you can't compare year over year, whether it's based on number of ideas, number of scaled outcomes, number of new ways of working or processes or growth within a team, again, you're not going to be able to prove the worth and the value. And that's still something that at the end of the day, it doesn't matter what team you're in or what you're doing to better serve a company, you have to prove that
Speaker A: well.
Speaker C: I think one that you just have to learn firsthand, which seems really obvious in retrospect, is just that the same processes and procedures that you have for one team of engineers with a, uh, team of three engineers at the whole company don't work when you have 10 teams of engineers with a hundred engineers at the whole company. And it isn't immediately obvious when you're in the thick of it that if things are going super well and you're hiring and hiring and hiring and building more and more teams, that you actually need to change anything.
Speaker A: Right?
Speaker C: Because things are going well, people are deploying code, more customers are coming, revenue is increasing. You don't always just take a step back and think about what efficiencies are we missing out on by not adjusting our processes? Or, you know, kind of the opposite. Like, what problems are we causing by maybe moving too fast when we've got a growing team and need to just take a step and slow down and make sure that we've got work siloed off in a way that's causing people not to kind of step all over each other all the time. There's different ways that you coach folks depending on how much skill they have, right where they are in their development of a specific skill. And so you just have to identify that. And maybe it's ask them questions, maybe it's give them a project plan, right? Give them ideas on the steps along the way. Maybe it's give them steps and maybe talk through the specific implementation, whatever it is. Maybe it's give them a partner to work with, but it's work. It's a lot of work as a leader to give somebody else something that's a stretch. You have to be really engaged to make sure that they're successful. And ultimately, you know, that's what makes you successful, growing leaders. I think it really expedites your own career growth.
Speaker D: Well, m. I would say when it comes to cross functional or interdepartment relationships, and that's really what we're talking about is it's about understanding your colleagues, what their needs are, what their motivations are, what their styles are. And honestly, communication is so key and understanding the way you communicate and how they're going to receive it. Because if you can find common ground in a conversation, conversation can be so powerful because it can unlock questions or answers that can really start to guide you down a path that you'd never thought of. And that's when it gets really fun and really exciting and you see light bulbs go off and both parties are getting energy from it, and that's what's really exciting. So I definitely agree that when it comes to the pairings and the yin and yangs, I mean, there's always a happy medium, but you don't want the extremes. You need the extremes in order to build the right team. But you also need to understand how those extremes can come together and work well and augment and supplement and complement one another. And I've found that as much as I might love to pull on the one that's pushing the gas and the other one that's pushing the brakes, you know, sometimes you need a little bit of that opposite in your life, but you're never going to really succeed, at least from an innovation standpoint, unless you have all of those extremes. If you're thinking completely outside the box and then you're thinking about how can the scale and be operationalized, because nine times out of 10, it's not going to scale and be operationalized in the original ideation phase. And so you can't just have one extreme or the other. And that's when teams come together. It's a lot harder than it sounds. But when you can unlock it, it's really powerful and magnetic too. M
Speaker E: I think that the culture of the organization is first and foremost, if you have a great culture in an organization, then great people are just naturally there because they're driven to to being in a culture. And echoes culture is like we carry the load together. We do hard stuff, but we do it together. And I think that becomes part of the reason that this team is so great because they're always willing to lend a hand and to learn from each other and no one is shy to say I got your back or help you, which is absolutely incredible. And there's no of this, it's me and I was the reason and the superhero this got done. It was, hey, here's the team and kudos to this group over here who helped us and our partners over in DevOps. So. So it's absolutely incredible to see that. And that's the culture. I think the other thing is when I came into the org, I met with everyone. I think it's important as a leader to meet with everyone on the team and have a personal relationship. So even if it's a 15 minute coffee talk with them just to say, tell me your story. I want to know why you're here. I want to know what your goals are. And that connection allows me to reach out to them and say how are you doing? Even on Slack or see them on a teams call and say how's the this looking? This issue seemed hairy. What did you find? Right. And then when I send my week in review emails and I talk about things like accountability or our need to do better job of communicating or documentation and I, I do send emails every week just about what's going on in new. Org and what are the themes I saw about opportunities that we have. Like they'll read it because now they know that what I'm saying, it's succinct and it's there, but it's there for a reason because it's tied to our strategy and our technology goals. So a lot of it has to do with the leader putting in the effort to build a lot of the relationships and the communication channels so that they can feel like you got their back and therefore they'll go out and they'll tackle that next task. And when you say, I know this is hard but I believe you can do it and they trust you because you know them, you see them, you recognize that they're there and the hard work that they're doing.
Speaker A: I had heard from the product and engineering team that, that, you know, we just have like lots of production issues, right? And so I had the team sit with customer service and listen in. And I kind of thought the goal was to identify the problems, right? That's what I wanted out of that. What ended up happening was you certainly do some of that, but as I mentioned, you just get inspired by the work that's happening and the value you're creating. Because often as people who build product and do software, you're so disconnected to the end user. But the surprising thing, and this is what I would suggest everyone like, do, is it actually created an improvement in team morale because now you're sitting with this person that kind of sits in the customer service team. But you see them, you have coffee with them, you have lunch with them, you say hi to them, how was your weekend? And you realize that this is a person who's trying to do their job. And uh, you realize, oh, like I what I built, the software I built, in some ways like helps them, but in some ways like causes them problems and there's empathy that's built and the team comes back with like a lot of kind of connections and energy around the company and what we're doing to try to help each other.
Speaker B: Foreign.
Speaker C: It's important to get to know people. You can't get to know them in big groups. And I'm an introvert, so I prefer one on ones as opposed to large groups. But I also find that you just learn so much more about people and it allows you as you're kind of constructing the uh, org structure, making sort of tweaks where people fit in, right? Because we really, it's somewhat of an art of understanding. Everyone has their strengths that we want to make sure we're focusing on, right? We're giving them the opportunity to focus on their strengths. And so finding the right place for people is super important. And that's just listening, right? That's the conversations and that's listening. So I do a lot of that. But I'm also a big proponent of. You really have to understand the level that they're at in terms of their leadership capabilities and always give them a stretch opportunity. Right? That is the number one way that I grow folks is give them the stretch opportunity and then support them through it. Right? You don't want to give them too large of a stretch where they're struggling and you have to essentially do it for them, or if you don't, they're going to fail. You want to give them just enough so that they can come back to you and ask questions, and you can observe and see where you need to kind of catch them right. Before they start going in the wrong place. But it's the stretch opportunities that I think are so important. And then being there for your team to support them. Right. Ensuring that they're successful, give them the confidence. I have found that to be super successful. I've seen a lot of people have really strong career growths as I kind of give them more and more and more slowly give them larger teams, more complex projects, leadership. Not just direct people leadership, but influential. Right. When they're not directly reporting to you. One of the hardest things to do, right? To drive a project with a lot of people that aren't reporting directly into you. So trying to kind of slowly grow them and give them more stretch goals. Super effective. So I say that's probably my number one secret weapon.
Speaker E: Remembering that it is my choice for how I respond to situations. Right. And remembering why I'm here. And that is to be of service and the vehicle of service and success for all.
Speaker D: Ah.
Speaker E: Of my team.
Speaker B: Christina leaves us with a powerful reminder. A leader's primary role is to nurture and foster the success of their team. Throughout this episode, we've heard incredible insights on building strong teams, fostering diversity, sharing knowledge, and growing as a team and as individuals and as leaders. I loved revisiting these conversations. It's always so much fun, and I hope they've sparked some ideas for you as well. Thanks for listening, and we'll see you next time.