Build Your Superpower Team That Actually Wins (Retention) with Tiffany Gonzalez

What's your superpower? Like, what are you great at? And instead of trying to give you performance coaching on things that you're not great at, how about we have a conversation and double down on your superpower.

Most companies, they don't train their leaders. Like, "Hey, you're the number one rep. Go be a leader." Wildly different skill set. As a leader, while you're unintentionally conveying is that you don't care enough to be completely honest with the person that you're talking to.

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Welcome back to another episode of the Bridge the Gap podcast powered by Revenue Reimagined. Today's guest is Tiffany Gonzalez, a GTM leader, startup adviser, and founder of Bombul who's led revenue at giants like Microsoft and Amazon. She's helped take startups public and rebuilt her own life and leadership style after a medical crisis that forced everything to legit stop. This episode's going to be about moving from activity to impact, from revenue theater to real retention, and from GTM as usual to something that actually lasts. We're going to get a little bit personal, a little bit different. We're not going to talk about what AI agent to build. We're not going to talk about the state of cold outbound. This is going to be real. This is going to be raw. This is going to be fun. Tiffany Gonzalez, welcome to the show.

Thank you very much. I'm glad to be here. I'm a little nervous because this is the first time I've shared this story, but I think in the context of how I lead and the business that I'm building and what I do and how I advise my clients, it's incredibly important to share because I know how many other people have gone through similar types of experiences without having the support, the network, and whatnot. So I'm excited to dig into it.

Likewise. Awesome. Welcome, Tiffany, and we appreciate that. So before we go into dashboards, before we go into sales process and all sorts of other things, you went through a life-altering experience and came back leading differently. What happened?

Yeah. The shortest version, and I'm going to make an assumption that many of the people listening to this podcast have children, right? Many years ago now, my son decided to join us in this world, and on day one of life he had a medical crisis that in most situations would be life-ending. He was born with a rare disease that we did not know he had. And as soon as he was disconnected from my body—so to speak, right after the umbilical cord was cut—he started to go into medical crisis. This meant a very, very, very long NICU stay. In fact, I didn't effectively hold my son until almost a month after he was born.

Yeah.

And as he went through that crisis, and this is actually when I was in South Korea—when he was born in South Korea.

Oh, wow.

Yeah. It was pretty. I mean, an amazing health care system. So I'm so grateful to the health care system and the physicians that saved his life because that really is a miracle. We did have to medically evacuate to the United States because the treatment that he needed was not available to him there. And so as I was running this GTM team of many hundred people—marketing, sales, analytics, sales ops, all of the things that we all do day in and day out—me as the leader, I had to go.

Yeah.

I left, and there was no—I was not thinking of work. I left and I was with my family and my son with full support of not only my entire team but of the company to go figure this out, right? To whatever it is that happens, go get better, right? In whatever sense that could be true. And so we were in the United States, and about four or five months after my son was born, he was stable enough to receive a transplant, which was curative of the disease that he was born with.

That's awesome. It was. So he just had his eighth birthday a few days ago.

Yeah, pain in my neck and my back and all the things.

Yeah, they all are.

Um, but he is a happy, healthy kid. He is doing amazing. That disease, while the transplant was curative, the disease before he received the transplant was so impactful on his body that he is permanently disabled. So he's the joy of my life. He is cute and happy. I mean, this kid—his worst day is when he has a booger that he can't get out of his nose, so to speak. But he is just a joy. That does mean though that through that leadership challenge and caregiving sense, managing his disabilities, managing his very complex care, being a caregiver and a present parent not only to my other children but to my son, and then my relationships with my family, and then how do I show up at work—it fundamentally changed everything that I do, and that's been a challenging journey.

So first and foremost, thank you for sharing. Thank you for being vulnerable and being open. That's not an easy thing for people to do, especially when it comes to our children. I think it's a lot more easy to be vulnerable about ourselves, but when it comes to talking about our children, that's really difficult. So kudos to you and thank you for sharing. I would love to know the balance is hard, right? Like all three of us are parents. It's hard enough to balance stakeholders. You know, I have my kid who comes into my office and wants something and my wife needs something and I need to spend time with my family, but we have this deadline that we have to get done for a client. That balance is hard enough without adding injury, without adding disabilities, without adding life-altering experiences. How has this changed your view when it comes to both leadership and just overall how you approach work versus family?

Yeah. I'm going to start with the last question and work backwards because that's kind of how my brain works. But when I think of work and how I balance work, that has been one of the most difficult challenges, right? And this is where I am. I still struggle, right? I think everybody does. I had to move into a place where I could truly balance not only the type of work that I do, but the who that I work with and how much so that I could be present with my children, with my family, and give all of what I can do to my clients, right? And while I'm extraordinarily grateful for the experience that I've had at companies like AWS and Amazon and Microsoft, I mean, they're small little companies.

Small little companies, Tiffany.

Not exactly known to be low pressure or dial it in environments, right?

Yeah. Not exactly known to be the super "no problem, take the time you need" type places.

Yeah. No, I mean, they're great companies and there's incredibly brilliant people there, but I realized that that culture was not one—just in general, that type of culture wasn't one that I could show up in with 100% of my energy and authenticity, right? And I knew that if I wanted to continue to do my best work, I needed to change that structure. And for me, that's been one of the hardest things because I can think 20 years ago and I'm like, "Okay, I'm going to be a VP and a CEO, and, you know, etc., etc." We all get on our own.

Not always cracked up to be, everyone.

Yeah, exactly. We all get those—I'm going to get my MBA and then I'm going to do the thing and conquer the world. I really had to sit back and, you know, even as we get older, we still hold those notions in our head, right? And that personal rediscovery was really, really challenging. And so that's changed my balance of work, right? And that's changed and informed what I do. Stepping backwards from that though, as a leader inside of these organizations and in how I manage people, I stepped away from a lot of the kind of more traditional big tech norms. And the most important thing to me was fully understanding the capabilities of the people on my team.

And this sounds natural or maybe this sounds intuitive, but I often find that people are like, "We need you to do the thing," and I don't care if you're good at it or not, but figure out how to do it, right? And I'm being a little brash in how I'm saying it, but that message is often conveyed in one way or another, right?

Sure.

And for the teams that I had built, I really shifted away from that to say, "Who's your superpower? Like, what are you great at? And instead of trying to give you performance coaching on things that you're not great at, how about we have a conversation and double down on your superpower and amplify that because you're going to have exponentially more impact." Yeah, there's always your lane of genius, and we run into this a lot with our companies that we work with, and as you go into your—

Your next evolution of your journey when you're working with smaller companies versus like the big companies where some people can hide. Not the leaders, but there's people that fall through and it's very difficult to hire. One of the things that we've been doing a lot around is jobs to be done. Like, what are the jobs to be done? And then not boxing people into "are you the right person in the right seat at the right time?" And you kind of have to look at it that way when you're in a smaller organization because every day sometimes matters. Every week sometimes matters depending on where you are in your evolution and growth. And it's unfair to people to put them in a place where it's not their lane of genius.

So I find when I speak with leaders or I talk with other people, they have a hard time asking the question, "What do you really want to do?" And then if it's not what you are doing, do you try to find another position within that organization? Do you have to have a hard conversation? And I'm with the clients this week and we've talked a lot about having the hard conversations about, "Let me help you transition to a place where you can be in your lane of genius." And I think that's a really hard place for leaders to be, especially in larger organizations. With your new organization, the thing that you're building today, I'm curious how you will transition that lane of genius thinking to them.

This has been one of the areas of the process that I've really tried to slow down on and really think about how do I purposely create an environment where everybody feels open enough to say, "That's not the thing that I love to do, or like, that's not the thing that I'm great at. I'm good, but I'm not great," and everybody to show up in an incredibly present way.

For me, a couple of the things is that every business we have to get in challenging conversations, right? One of the things that I've really tried to embrace is an openness to disagreement. And that disagreement is not built on "you're wrong, I'm right" or any of that type of stuff, but it's really around, "Hey, something happened, and what is it that occurred that we can learn from together, right?" And then, for example, Dale, if I'm challenging you and I say, "Hey, I'm imagining that this is what caused that to happen. Help me understand." Right? So I'm disagreeing, but I'm doing so in a way that's incredibly constructive.

And those are not muscles that a lot of the industry has built at scale. And that's really, really tough. I'm finding a lot of people are craving that type of thing but don't have the language for it. And so that's been part of my journey—trying to find that language.

Yeah, and I want to just a quick little followup on this. We're at a leadership offsite with a client of ours this week, and I have to say the CEO, because there are challenging things that are happening in the business and lots of evolution, but one of the things the CEO did that I thought was very prevalent to what you just talked about was basically say, "I'm going to leave an open space and an open mic for everybody, but I'm going to be the first one on the stake and I'm going to identify the things that I think I'm good at and the things that I think I have a challenge at." And then he opened it up to the whole leadership team and he said, "This is a safe space at this moment. Like, whatever you say—arrows, not arrows—like, what is it?" And I think having that vulnerability in that space enabled other people to have vulnerability in that space.

Now the interesting thing that I found in that conversation was even when people were asked to open up and give challenging feedback—the goods and the challenges—the goods were very easy for people to say. The challenges always came with a caveat. "I know your challenge was X, but..." And so they diffuse the conversation. I think you need to be able to give tough feedback and move on. It's not emotional. It's not good or bad. It's just a fact. And if we can figure out the facts versus the emotion, then we can just push through it. Can we resolve it or can we not resolve it?

Well, this is where I'm going to challenge you on it. Right?

People are inextricably emotional. Like, we all are emotional beings, right? And there's no way to decouple those things. If we are not emotional, just to throw in a buzz word, if we're not emotional, we're AI, right? But we fundamentally are emotional.

And so the question is, how do you build a place of organizational agility so that if you're challenged, where someone imagines an output like, one, everybody needs to start from a place of good intent, but two, if you're challenged on something, one of the things that I would love for that leader to have done is say, "If you're emotionally responsive to this, we are holding space for you to go take a walk around the office, walk around the building, and get into a frame of mind where you can not be controlled by your emotions, but understand them and be ready to buddy them with you into the further conversation, right?" And that's the same.

I think what you just said is key. You don't be controlled by your emotions. Emotions are okay. Like, everyone's going to have them, but at the end of the day, you can't be controlled by them and you have to understand them. It's the same as when you're having a bad day, whether you're an adult or a kid. If I am having a conversation with Dale, which typically is—no, I'm kidding. But if I'm having a conversation with Dale and for whatever reason it's a crap conversation, I don't get to go take that out on my family. Like, I could have the emotion of, "Man, I'm pissed and that wasn't great," and then I have to walk out with a smile on my face. It's the same thing. It's okay to be emotional. I think where I see people really struggle is—and I'm super curious your take on this, Tiffany—it's not the emotion. It's taking everything so deeply personal. Just because you're not doing something the proper way, or we think it should be done a different way, or there's a different approach, it doesn't mean that it's you that's being criticized. It doesn't mean that you suck. But people take any type of negative feedback as a deeply personal criticism.

Yeah, I think we're not getting—

Dale cries all the time.

I know. Exactly.

Like, "You're hurting my feelings."

No, I make Adam cry all the time. That is what you—

I mean, I do. I walk away and I pout because Dale hurts my feelings.

And I want to make one clarification real quick. It's not the person getting the feedback. It was the person giving the feedback, negative or positive. So it's a weird thing internally when you're giving feedback to somebody that you're caving on any of the challenges. And to me, the way you deal with that is with empathy. So it's not that you need to walk around the office. It's the uncomfortable conversation of someone giving challenging feedback. So if I'm giving challenging feedback to Adam, I'm giving challenging feedback to our other partner Jake. Like, it's hard to give that feedback without putting a caveat on it.

And so we need an empathetic space and a transparent space where people cannot feel attacked.

But I've always learned that it's how you take the information. But it's also how you say it. Like, I used to be incredibly guilty, Tiffany, of starting a sentence with, "Tiffany, listen," or "I don't want to sound like an—" Even just saying that is like, "I know I'm about to sound like an—" Just say what you need to say. Don't put that caveat on it because it makes people defensive. The other one is—and I'm wildly different, but I hate when people are like, "Well, do you want me to be honest with you?" No, I want you to lie to me. Like, of course I want you to be honest. Come on now.

Well, and that's the biggest thing. One of the hardest things as a leader is to learn how to sit with discomfort and to embrace the discomfort, right? Because I understand—and I've done it a million times as well—I understand the tendency to kind of put a caveat in there to soften the message or things like that. But what, as a leader, what you're unintentionally conveying is that you don't care enough to be completely honest with the person that you're talking to. You don't care enough to trust them.

That they have the emotional capacity to receive and then have a difficult conversation, right? As a leader, that's foundational, right? You have to be able to communicate those things in a way that you're not caving, but you're also not blaming and you're also very, very clear about, "I don't know the answer to this because I'm perceiving something. I'm imagining something is occurring. Please help me understand," right? So you go with them and not at them. And that's a very different space than a lot of the systems of our large tech organizations just across the industry. They don't operate in that same way. And it's understandable. It's hard to drive.

How do people learn how to do that? Because that's hard, right? That's learned behavior. To your points, whether it's Amazon or Microsoft or Google or a startup like this, it isn't taught. And we often talk about it. My dream job, if you will, other than winning the lottery—if it paid—would be like leadership coaching. It doesn't overall pay. I think the disconnect, tying back to my question, is most companies don't train their leaders. Like, you were the number one rep, go be a leader. That's a wildly different skill set. How do we train leaders to be able to do this and be great leaders and build that empathy?

Yeah, that's one of the biggest gaps. I certainly don't have every answer. I'm not an organizational psychologist, although if I win the lottery, then I'll probably go back and get my PhD in that because that sounds fun. I don't know why. It just sounds great. But I think this is one of the biggest challenges in tech across all companies that we're going to face, right? Because when we look at AI—sorry, I was joking. We were going to talk about AI, but I bring it up—

Listen, you can't not talk about it.

Exactly. But as we talk about AI, right, AI isn't a tool. AI is work, right? This is the first time we've had a technology that can really do the work. And whether you're in rev ops or you're a sales leader or in sales enablement or whatever in finance, who knows? This is one of the first times that you're going to have AI tools that are doing the work and you're going to be the boss of those AI tools, right? And you're going to have to build your business with a human and tool structure so that you're able to guide and drive all of those in a very meaningful way. And from a human perspective, how you get the most out of AI is being blunt and being direct—you're wrong, you didn't think of this, include this in the variable, right? It's very, very direct. That same messaging to a human is going to land in a very different way. So this is going to be a challenge for leaders and managers everywhere to figure out how to balance both of these things so that you're really running your entire team, which is inclusive of people and AI agents, in a way that is authentic.

Yeah, I couldn't agree more. Tiffany, when you look at your experiences and everything that's happened, what's something that you used to chase that now is just so meaningless that you just don't give a damn about?

Oh my god, a million things, right? You know, I have to say, and this is—I started as a salesperson, right? I was in B2B sales for a long time before I moved into strategy and transformation and all those things, right? What I would say is I used to chase a number, right? Whatever that number was, right? I used to chase a number. And now I look at that number and I am able to break it down and say this is fluff. This is aspirational. This is realistic. This requires whole lots of investment. And is the organization willing to make those investments? And I really move it from a point of kind of abstract goals to how do you break it down into real meaningful frameworks, steps, and approaches so that the team isn't buried under a number that isn't achievable, right? And that's probably the biggest one for me. I don't know. I'd have to think more about it.

No, so that's a great answer. I want to piggyback on that. So with that, what are the must-have metrics that teams need to obsess over? The leading indicators that will drag you to what you need to look at? Like, what are the top three or four things that when you're working with someone, you're like, "This is where you need to obsess, not this BS that you're obsessing over"?

The biggest thing that I think of from a broader framework perspective is stopping the manual work tax. Understanding across your business where that manual work task exists, that manual tax exists, and how much it's costing you, right? And then either stop doing it or make it valuable enough to be worthwhile doing or automate it, right? Those three things. It is shocking how much time and space and energy across engineering and product and so many other teams are like, "Oh, just make me this quick report. Oh, just make me this quick report."

Yeah. Oh, that quick report that, by the way, you have to build a data pipeline in order to get? No cheap or fast or quick, right?

Yeah.

So I think that's why we're doing a lot of jobs to be done. And when you identify elite jobs to be done, now you can really figure out where AI can help you a lot.

I love that. Let's wrap up with some rapid fire. Really quick little answers. And I think since we just talked about metrics you should be tracking, what's the most overrated go-to-market metric?

ARR.

Oh man, do I wish we had time to unpack that. That might have to be a version two. That's a very interesting answer. Tiffany, what's your go-to fix it fast move when a team is stuck?

Go talk to six customers.

Love that. Absolutely love that. I saw a post from someone who shall not be named, who I disagree with a good amount of what they post on LinkedIn. But this was a great one. Whether it's a CRO, VP of sales, any leader—if you are not talking to customers in your first week, you are the wrong person and you need to immediately have a listen. Tiffany, sorry, we made a mish-hire. Done.

Because you're never going to do it.

Yep.

What's more dangerous? Bad culture or bad process?

Bad culture.

Bad process is more expensive. Well, they're both really expensive.

All right, we're going to throw someone under the bus here. What's the one GTM tool you'll never recommend again?

I'm going to cop out on this one a tiny bit, but what I'm going to say is any tool that you're adding on to your tech stack to fix a problem, to bandaid or duct tape a problem, because you're not solving it. You're just duct taping it, right?

Yeah. I think that's a great answer without burning a brand. I love it.

Yeah.

Last one. Dream vacation destination.

Thailand.

Thailand. I'm a scuba diver. I love getting in the water. It's scuba diving. If you have never done it, it's like underwater zen. You can't do anything but just be. And it's so gorgeous.

Let me know when you go. We spent a month there a couple years ago. All sorts of places to give you.

Tiffany, seriously, from the bottom of my heart, thank you for being vulnerable. Thank you for being open. Most of our episodes are deep GTM strategy. I think this hits home for me. It certainly will hit home with a lot of other people about leadership and life, about what's important and what's not. It was a pleasure having you on the show.

Glad to. Thank you so much.