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Alan Zhao: [00:00:00] All right, today we have here Dana Warren, who is a venture partner at Canaan Partners, which is an early stage venture capital firm. They've had early investments in Instacart, the RealReal and Match. com. Dana herself has had 15 years of experience building and running revenue, marketing and strategy at companies like American Express, PayPal, and Stripe.
Alan Zhao: And most recently at Stripe, she's helped build and grow global strategic partnerships with companies like Shopify, Salesforce, and Squarespace. Being a part of fast growing companies means leadership is often faced with hitting ambitious goals. So today we're going to talk about how to build an A plus team to hit those goals.
Alan Zhao: Dana, it's great to have you on today.
Dana Warren: Thanks for having me.
Alan Zhao: Awesome. So let's get started with, um, a quick background about yourself and we'll dive [00:01:00] into the topics.
Dana Warren: Sure. Happy to. Um, so I'm originally from New York and a fun fact about me is that I started riding the New York city subways alone when I was eight years old.
Dana Warren: So that usually takes people back. Um, so I'm originally from New York, lived all around the world and back in New York, three kids live in Westchester.
Alan Zhao: That's wonderful. I used to live in New York for four years. It's very hectic. It's a, but it's a great city. So how, what does amazing leadership look like?
Alan Zhao: You've worked at many amazing companies. You've had, I'm sure, uh, incredible bosses. What, if we could visualize it for the audience, what does that look like?
Dana Warren: Yep. I appreciate Allison that you talked about having great bosses because I think that's really important. I've seen great leadership in action and it was actually at American Express under Ken Chenault's leadership as CEO where I learned about this comment and theory around followership.
Dana Warren: It's not enough to be a leader and be told that you're the boss [00:02:00] and there are lines on an org chart that report to you. You actually have to create followership. You have to create a team. That believes in you, that sees that you are excellent at your craft, that you engender support and you focus people on delivering results and you actually enable them to do so.
Dana Warren: So for me, great leadership is all those things that I saw firsthand and was trained on at American express. And I've carried that throughout my career.
Alan Zhao: That's great. And how about an A plus team? What does an A plus team look like?
Dana Warren: I appreciate that question because often folks ask me what are the tricks of your trade when it comes to leading sales, revenue, marketing, or strategy teams.
Dana Warren: And I always start with A plus team is an A plus player only team, no exceptions. And what that really means when you define an A plus player, this is someone who is excellent at their craft. They are always [00:03:00] pursuing the answer. They dive into the details. They analyze deeply. And it doesn't necessarily mean that they all look the same.
Dana Warren: Quite the opposite. You want a really diverse team. You want rich experience. experiences, different backgrounds, different careers. In fact, I often tell the story of someone who was on my team at Stripe who was actually formerly a lawyer and he was a salesperson on the team. And what was incredible was that he could bring that analysis that he was trained on and frankly probably also had the intuition and really dive deeply into his prospects and customers.
Dana Warren: And I often would say we need to, as salespeople. Understand and analyze our prospects the same way or better than a Morgan Stanley analyst understands the company they're covering. It's as if we're on every earnings call. And so I think when I talk about A plus player, it's just that, that you want to pursue excellence in everything you do and [00:04:00] understand really what the possibilities are.
Alan Zhao: I love that. Some of our best engineers actually came from pretty non traditional backgrounds, including law, including investment banking. They have a very keen attention to detail, which does very well in a very, uh, structured role like engineering. So do you have a particular example that comes to mind of an A plus player that you've had on your team?
Dana Warren: Yes, I think the previous one's a great example, but I think another one, a different angle of, of what a plus means one of the trainings I took actually a dear friend of mine at PayPal introduced me to the notion of strengths based leadership. And this is really about by the time someone comes on to my team at this point in my career, they've been in the workforce for some time and they have a Demonstrated areas where they're strong, and we're going to lean into that, and then we're going to try to improve areas where they need development, but we're going to really exploit, take advantage, celebrate the things that they're best at.
Dana Warren: And you asked for [00:05:00] another example, and an A plus player who joined my team was a sales. He was a sales manager. And he came with incredible payments background and we were at a payments company and he understood the value chain and payments like nobody else at the company at the time, in my humble opinion.
Dana Warren: And so I leaned into those strengths. I brought him to team meetings. I had him shadow sellers. I had him share trainings, write documentation, really create playbooks to lift everybody up. But what I also asked him was, what was he there for? What was he playing for? What was his motivation? And he really wanted to become a sales leader.
Dana Warren: He wanted my job. And so we worked really hard on giving him those opportunities to step into, not leap into, but step into. Leadership and really coaching him on what it means to be a leader, what it means to actually be that sales leader. How do you create territories? How do you define forecasts? [00:06:00] How do you keep people accountable and how do you coach them?
Alan Zhao: I love that answer. And this segue is really nice to say into the next. topic, which is like when you're a leader and you have to manage A plus players who are incredible in their own right, then how do you coach them? What can you provide? And what's the perspective to think about this through it?
Dana Warren: In my career, I have run into many people who, when they have great teams, they truly believe that they can set it and forget it.
Dana Warren: That they can let the teams run themselves or sales leaders who sometimes think their job is the pipeline report and managing up. And respectfully, I think that's really missing the whole point of the job and minimizing the potential of a team. The way that I really see my role is to be the coach and, um, I know in sales, a lot of folks say ABC always be closing for the type of deals I've led in my career.
Dana Warren: That is [00:07:00] absolutely not the right thing to do. If you're doing a large strategic sale. You do not want to be closing on day one. You want to be questioning, understanding, analyzing, building a relationship. And ultimately, if you close too early, I have found you're likely leaving money on the table. So instead, I create a culture of always coaching on the team.
Dana Warren: That means we are prepping for every meeting. We're actually role playing myself included. We are going to meetings with others so that it's not just about recording. The meeting on gong. It's actually listening. They're live traveling to Canada with the team members so that you can see what were the cues in the room that they missed or that they leaned into really well and then immediately, you know, after every meeting, you're going to get feedback, whether that's from your peer, your direct report or me, and ultimately, you're You create this culture where everyone's each other's coach.
Dana Warren: Everyone [00:08:00] embraces the feedback and they grow because of it.
It's
Alan Zhao: amazing. It doesn't always start off that way. Do you have any advice on how to build that type of culture?
Dana Warren: Um, I really appreciate that question because I've worked on teams where I inherited greatness and I've also worked on teams where we either had to rebuild, which is really hard, or start from scratch.
Dana Warren: On the starting from scratch, the benefit is you get to leverage your network. You get to bring in people that you stand behind. And frankly, my perspective is if I hired you, I'm coaching you, and I'm believing in you and creating an environment of trust. The really hard one is when you inherit and you have to rebuild.
Dana Warren: And oftentimes that means you have to be very clear about your expectations. Oftentimes, when I started a company or start with a team, I share a memo about me and it's a learned behavior. This did not come naturally. What is it like to work with me? What are my norms? When can you expect [00:09:00] to get a slack from me?
Dana Warren: When am I going to? Ask you for pipeline reports. When am I going to get the group together? And what are examples of pitch decks that I love? What are memos that I think are outstanding? Do I expect you to share notes from every meeting? Just truly share who I am. And then frankly, folks can opt in and opt out.
Dana Warren: They can read that and say, Dana is going to Slack me. Often, and I don't want to be part of that culture or I am okay working seven days a week and the fact that she said she's not going to bother me on the weekend unless it's truly urgent. Like I'm here to work all the time. I use that example a bit tongue in cheek, but the point is.
Dana Warren: As a leader, you need to set the expectations really early and then be consistent, because if you don't deliver on the person that you've articulated you are as a leader, folks are just going to opt out anyway.
Alan Zhao: Do you have any particular examples of when [00:10:00] someone that you've seen or? Maybe even yourself earlier on where you weren't consistent and what was the cost of that?
Dana Warren: Oh, absolutely. So I feel as if we could do a whole bloopers reel of all the things I did wrong as a leader, and I'm happy to share that as well. I think part of being a great leader and a great human and a friend is recognizing that. You make mistakes every day, right? Um, I think of one that really stands out.
Dana Warren: A woman actually, who was on my team at American Express gave me direct feedback when I was a relatively early manager, but a large team, I think there were about 30 people. And I actually had just had my first daughter and I never spoke about her. And she came into my office at the time. It was a pretty traditional structure.
Dana Warren: You became a VP and you've got an office. And she walked in and she said, I'd like to give you some feedback if I may. I said, absolutely. She said, you never talk about your daughter and you're the only female with a child at your level in this [00:11:00] group. So how are we supposed to know that you can do both, that you can excel and have a child if we don't let us in to what you're doing?
Dana Warren: Fast forward. I told that story all the time. And then. When I joined Stripe, I recruited her and said, do you know this? You're part of my leadership stump speech. You have to be true to yourself. You have to bring your whole self to the field. Everybody is dealing with things at home. They're very different.
Dana Warren: They're really varied. People have times when they're dealing with stuff that takes them away from their concentration. If you don't share who you are and how you're balancing. I think it really makes you appear like Teflon and really difficult to connect with. And frankly, it's less motivating.
Alan Zhao: You gave a couple examples when we were talking before this about radical transparency within the team and to make sure that no stone is unturned.
Alan Zhao: Everyone's speaking their mind, surfacing their opinions to make sure all bases are covered. [00:12:00] Um, are there other examples in the company that, that you've seen where being transparent and covering all the bases, it's benefited you guys?
Dana Warren: Absolutely. I would say countless. Um, more often than not, it is rare to be a team that is full of trust and transparency.
Dana Warren: And more often than not. There are teams that miss important details because of it. And so what I mean by that is my finding is when you're building your team, if you don't create an environment, whether that's a seller, a customer success leader, a marketer that folks. They have to feel supported and they have to know that they're in an environment where psychological safety is number one, it's paramount.
Dana Warren: And when you do that, I've seen firsthand folks take calculated risks. They propose creative solutions and they accept that they're going to make mistakes and get feedback [00:13:00] and coaching, and then they'll deliver something even. Um, I think in a time when, uh, one example would be, we were preparing, we were putting our heart and souls as you do your work, um, in preparation for a huge deal that we were working on when I was at PayPal.
Dana Warren: And it was a really meaningful piece of the business. And I was let, I was letting the team. Just go through the motions because the stakes were so high, there was incredible pressure and we didn't take the time to go slow so that we go to go fast. And ultimately, our first pitch on this massive consequential deal, I hate to say cosal failure, but it was as close as it could get.
Dana Warren: It didn't resonate with the client folks didn't know their roles. They didn't feel comfortable. So my point in sharing that story is obviously back to my previous point, everybody makes [00:14:00] mistakes. You learn from them, but actually the results really show whether or not you have prepared, you've given people feedback.
Dana Warren: And I think it comes back to the comment I made earlier, which is this has to be a coaching environment. It has to be a plus players and you have to create, especially as a revenue leader and environment where it's not just about pipeline and prospecting, you're coming together as a team and you're tearing down the strategy and building it back up in a way that it's better than it would have been if you weren't all working on it together.
Alan Zhao: Yeah. 10 minds, two minds, all of which are better than one mind. Thinking about it in isolation. Um, so we talked a little bit about coaching and giving feedback that gets to a point where sometimes coaching is not enough and you might need to manage certain people into other roles or how do you manage underperformers?
Dana Warren: I think that's an important question. It's a delicate one, right? So my modus [00:15:00] operandus in life is always operate from a point of respect. I talk about in meetings, we will disagree. We should disagree. That's the purpose, or else we could do this all remotely, async, and alone. But It has to be from a perspective of respecting the other person and respecting their opinions and respecting the differences.
Dana Warren: Um, having underperformers is incredibly complicated. It's incredibly stressful for the performer, the team, the leader, and. It's very hard to get it perfectly correct. But if you start with this point of respect and articulating that this role isn't a fit for their skills. And I would also add, and I learned More recently in my career that you act with urgency around it.
Dana Warren: It's not good for anyone to have an underperformer. As I mentioned, it pulls the whole team down and [00:16:00] likely the individual. And my experience knows that they're underperforming and has that psychological weight of not delivering. I will tell you that there are really great stories. I have, I think, countless stories of having a performer on my team who is sitting in a strategy role.
Dana Warren: I have this. example from when I was in American Express, we were doing strategy. She was struggling. The results weren't there. And we talked about the elements where she was performing above and beyond. And I sat with leaders who are really respected. And I said, we need to find a place. For her to deliver the areas where she's strongest, which are clearly marketing.
Dana Warren: We moved her into marketing. She was one of the top performers. So I think that's the other piece. Um, companies are lots of different sizes, different phases. Sometimes there aren't those roles available, but you do need to find what the skills are and make sure you're leveraging them.
It's
Alan Zhao: amazing. One of the things that you also mentioned as being core to [00:17:00] strong leadership is knowing where to place your people.
Alan Zhao: How do you find the top players?
Dana Warren: This is really hard. I think that there have been so many books. I've read some, um, I've met with many people, but my experience, I was really lucky. Uh, when I joined Stripe, I got to be part of a rigorous process that I experienced as a candidate. And then I delivered as an employee where there was a structure There were prepared notes, prepared questions.
Dana Warren: Every interviewer was trained. And for me, that is really critical from, from a hiring perspective to your question around, where do you find them? How do you source great candidates? I think that's really important because we must, it is my responsibility as a leader to ensure that I don't hire people that just look and sound like me, right?
Dana Warren: And so our social networks tend to. [00:18:00] Lean into folks that have the same background. So yes, you're going to reach out to the top performers you work with before and you're going to tap your linkedin network and where you went to school, but you are really going to lose if you're only doing that. I worked with.
Dana Warren: Phenomenal recruiters, a great example at American express. They always had a diverse slate, diverse in background experience, culture. And we spent time and frankly, money ensuring that we were tapping into all of the networks that existed for underserved candidates for diverse experiences. And we showed up and we demonstrated that we actually really were going to be hiring, which is an important point.
Alan Zhao: That's great. Some of our best candidates have come from the extremely untraditional and it's not where they came from or what they've done in the past. Um, but what they can bring to the table. So definitely agree with that. Uh, we're gonna end with this question, which is, is there anybody in your [00:19:00] career that you'd like to give a shout out to?
Dana Warren: I love this question. I have been. Literally blessed with working for incredible leaders, um, two folks at Stripe who recruited me and I got to work with and work for, we're still there, Jean DeWitt Grosser and Christian DeCarlo and at PayPal, a woman, Kathleen Pierce Gilmore, who's now at Visa. She said something to me that stuck with me forever, which is when she hired me, she said, I hired you because I believe in you.
Dana Warren: I will have your back when you do well, and I will have your back when things get tough. And she did. And I've carried that with me. So thank you.
Alan Zhao: Amazing. How can people find out more about you?
Dana Warren: Well, I recommend going to the Canaan website, learn more about Canaan and my bio's there. And I am active on LinkedIn.
Dana Warren: So head over there and you'll see a bit about what I write about, what I do and my network.
Alan Zhao: All right. Thank you so much, Dana. Really appreciate having you on here.
Dana Warren: Thank [00:20:00] you.