A Leadership Toolkit for Leading Revenue Teams with Jerry Brooner

Jerry: The most powerful tool any of us has as leaders – and everyone's a leader, even if you're an IC or if you're a hiring manager or if you're a CEO. Anybody who's a leader. I think the most powerful tool you have is to lead by example.

Trinity: Welcome to The First 100 Days, the show for revenue practitioners by revenue practitioners, giving you unscripted access and tips to help you navigate any new transition or initiative both in life and at work. What are the most important lessons you've learned as a revenue practitioner for our guests?

The answer comes down to three things, consistency, talent development, and leading by example. Jerry Brooner is the President of Global Field Operations at Enable, a cloud-native B2B rebate management solution. In this episode, he shares the leadership lessons he's learned building sales teams for both Fortune 100 companies and high growth startups and how they affect the way he shows up today.

He'll share the importance of knowing what you can and can't teach when developing talent and how sales leaders getting in the trenches can make a huge difference in building trust. 

Jerry: I've been very fortunate to be part of and building some truly phenomenal teams, both at large companies, Fortune 100, and small companies. Everyone out there in sales and marketing knows building teams is hard. Building teams is really hard, no matter what stage of the company it is, it is hard, and, I've definitely made a lot of mistakes and I've learned a lot of lessons. There's lots of them, but let me try to narrow them down to three. I think I'd go with consistency, talent development, and leading by example. I know every one of those sounds like a platitude that is, you know, some panacea that everyone talks about, but they're basics and they're critical to growth of any team.

But let me start with consistency. If you are going to scale or if you're going to teach anybody anything, you have to be clear, easy to follow and super simple. You need process and structure that is so simple that not only my two year daughter could follow, but it needs to be simple enough for my two-year-old daughter and all of her preschool classmates who are two to follow as well.

That's how simple it needs to be. And for you to have any chance to scale and by scaling, I mean, you want to hire 40 to 60 people a quarter, you need to have a process in place where you can talk to 40 people and say, here is what you need to do, here's when you need to do it, and here's the process exactly.

I realized this early on in my career. When I first start any job, first thing I do is I go around and I ask a bunch of questions. I just ask questions. I'm like, how do you forecast? How do you generate pipeline? You know, what's hiring like? What's your career development? You know, what's our 360 feedback? All these things.

And it'd be amazing to me, for simple things like pipeline – you've come from marketing, people in sales, all know pipeline. How do we identify pipeline? What's the difference in pipeline? And from five people I'd get like 60 answers, right? So I learned real early on, you have to be consistent. It has to be simple. It has to be something everybody can follow.

That's consistency, tip one. Tip two, developing talent. Now this is an age old thing. Do you go hire the best talent or do you go develop talent or both? When I go to a company, first thing I see is they have a product roadmap, then they have a customer expansion plan, and then they talk about how they're going to improve market share.

All those things are standard across almost every company. What they don't have and what shocked me is when I go into a company and I say, what's your ideal employee profile, ideal employee. Do you have an employee, a perfect employee – skills, traits, background, values? What, what's your ideal? Most people look at me like I'm crazy and they'll have no idea.

So it's really hard to hire and develop talent if you don't have a very specific idea of what you're looking for, what works best at your company. Now, I remember when I was hiring a revenue team and then I noticed one of our field marketing directors was phenomenal. He was so customer-focused. He was super hardworking.

He was committed to success and he can recite numbers and calculations and the real value of our company. He turned into my not only my number one sales rep, he turned into my best sales manager ever. That's developing talent, right? That's a whole lot faster and a whole lot better longterm for your company than hiring someone from the outside who's a rising star who you need to train all over. That makes 

Trinity: sense. I want to double click into that one before you move to the third point. So I love that. That's going to be my new thing, ideal employee profile, because we, like every company right now, going through the hiring. Do you think the ideal employee profile would change from company to company or stages? Do you see any kind of common thread? 

Jerry: I think it's both, I think your ideal profile from company – because every company is different and the stage of the company is different. What, I don't think a company will change and which is why you can go from stages, what are your values as a company? What are your goals?

What is your mission? Who embodies each of those values and traits and how do you hire for that? 

Trinity: Before, I guess, selfishly using this interview also to pick your brains here. So, companies, like startups, like us, where we're in an early stage and the values and the cultures and the principles are still being formed.

Things that we think are our top three right now could change. I don't think it would, but like companies evolve and grow up. So what advice would you give for companies like our size right now, looking to hire the ideal employee profile? 

Jerry: I think you really have to, while you might change, I think what certain things won't change – your market, like what do you do?

What is your vision? What is your mission statement? Your values might fluctuate a little bit, but I have a hard time believing you will scrap every value you have now and start with a brand new set of values in two years. So, all companies come with a mission and a vision and some values. And I think those might refine over a few years, but I don't think they'll change.

So I would hire people to match that. You can teach skills. I can teach someone a methodology. I can teach someone a product. I can teach someone, you know, how to build pipeline. Here's what we do. And what I can't teach someone is hustle. I can't teach passion. I can't teach vision of our company. Does that make 

Trinity: sense?

Jerry: Yeah, and grit, too. Grit, one of my favorite words. Grit. We call it hustle, internally, literally hustle. I can't teach you hustle, right? But I know it when I see it. 

Trinity: All right. So, like, consistency, develop talent, and your last, the third one? 

Jerry: Last one and probably the most critical. I feel the most powerful tool any of us has as leaders – and everyone's a leader, even if you're an IC or if you're a hiring manager or if you're a CEO. Anybody who's a leader. I think the most powerful tool you have is to lead by example. I know that as a leader, every action I do or don't do is not just watched by my team, by my company, but it's watched by everyone in the market.

How I act on your podcast. Things that I say or don't say, right? Everybody's watching what you do as a leader. I think that's the most powerful example you could have. I was just in Toronto, and we have a great, phenomenal BDR team. We do a monthly call blitz, and I thought it was a great idea to go and join them for the day. The whole team did it. Everyone in the company. CEO did it. I did it. Now, it was a little embarrassing because I didn't get any meetings, but I sat right in there making calls with them during their call blitz. And I wanted to show them that I'm willing to do anything to help them and I would never ask them to do something I wouldn't do myself. Yeah, you 

Trinity: were sitting in the trenches with them. That's awesome. That's incredible. More sales leaders need to do that because call blitzes are challenging. 

Jerry: I tell you, I don't know. I didn't get one meeting out of that.

So, a little embarrassing. Probably, I should have come up with a better story. Now everyone knows I went 0 for the day on my call blitz. I'll do better next time, team. I promise. If anything, 

Trinity: everyone's going to target your BDRs because apparently the BDR's are really good, so yeah, be on the lookout. 

Jerry: I have a great BDR team. I would target them.

I don't blame them. I have a phenomenal team. I would target them. That's 

Trinity: amazing. That's great. So I want to circle back on the consistency because I think it is not mentioned very often, but I guess everyone always get attracted to the shiny new projects. Right. But it's something that – is a consistent something that you have to keep repeating over and over and over until it get internalized.

Like, I guess in simple terms, even in a sales enablement side, talking about the target persona, you're talking to the pain points they're going through. Everyone thinks that they know, but I'm pretty sure if you go survey on the floor and everyone would describe your target persona differently. Did you have any like tips to ensure that consistency stays consistent?

Jerry: It's interesting, Trinity, that you bring up sales enablement. I think sales enablement and sales ops are often the secret weapons for a revenue org that are overlooked. I have a phenomenal team in sales enablement and sale ops – but let me give you sales enablement in terms of consistency.

When I joined Enable, I said, take me through life and normal eddy. Just take me through your onboarding, what happens? So I showed up my first day and I went and I met with someone who said, okay, we're here to train you on it. And they pulled up a Google sheet which had four lines on it. Like one of the lines was the company website.

And that was the onboarding and training. And it took maybe 40 minutes. And I was like, that doesn't seem like great to set someone up for success. So our sales enablement team is all about consistency and structure. And let me explain what I mean by that. The sales enablement team is – before you even get to our company, once you get hired, before you can get to company, you will get a screenshot of your first two weeks. The first two weeks, every day by hour, exactly what you're doing and what to expect. Literally, the first two weeks. Every single person that comes into our org goes through the first two weeks. They have a welcome message.

They have, you know, here's some prereading on the company and here's what's expected of you for the next two weeks. And then after that they get another one for two weeks. Their first month is scripted. Consistent, simple, easy to follow. Everybody does it. Once they come out of that, everyone understands what we do, how we do it, and the methodology we use.

So that's where consistency begins. Sales enablement. Onboarding. 

Trinity: Has that changed or how have you guys adapted it for the remote world now? 

Jerry: Everyone's had to change for the remote world. Everything about the remote world is changing. I often wonder when we all went into the pandemic, I'm sure everyone talked about how everything was better in person.

And I would say that's true for the most part. Many things are better when you're in person. Many things. But I also think there was a lot of advantages to the remote world that we've come in, especially when it comes to scaling and hiring. What I've noticed is there's definitely nothing better than coaching one-on-one in-person. There's definitely nothing better than being able to do the ad hoc coaching. When you're on the floor or you're walking and you hear someone speaking or at a meeting and you walk up to somebody and you say, you know, how about this?

Or why did you do it this way? You can't replace that in-person. But what I think the pandemic has taught me at least is that you can utilize both. What virtual has really done and really made an impact for us is we're able to do training more often. We're able to get out to everybody versus scheduling flying in.

So we are able to provide more training. We able to provide more as-you-go training, right – videos, coaching, training, as you go along, and then we're able to create more trainings as well, all because it's virtual. So while I think that certain things are better in person still, we've really benefited a lot from doing things virtually.

And I think we've got great tools to do it. 

Trinity: That's true. I actually didn't think about it because I keep thinking about like how the ad hoc, the, like you passing by someone's desk and, like, Hey, you could have said that line better, but it's true. I did not think that, yeah, virtually now you can do more training and people can learn at different times now. They don't have to basically put their life on pause to fly to the headquarters to do training. . Yeah, 

Jerry: exactly. And think how often more you can do it. I'll give you a perfect example. During that call blitz, if I was sitting at home, I would have done even worse than I did. I got lots of coaching from my BDRs team. Thank gosh, next time, I'll do better. But at home, I never would've been able to have gotten that. 

Trinity: Yeah, that's true. Honestly, interesting. So outside of performing more, like doing more training virtually, do you have any advice for – it could be sales leaders, or just managers in general – to provide coaching and enabling your team to do better, especially in the remote world we're in right now.

Jerry: You know, for me, when I talk to managers or leaders, I think of ways you can always be coaching, right. And for me, coaching is not do it once or do it twice, or do it structured. You have to have structured, right? We have structured training. We have a dedicated one-on-one for every manager.

We have dedicated career. We put a structure in place for all of these. What I will always say, I feel you can never have enough coaching, right? And you can never have enough coaching immediately. I'm guilty of this, too, at times. You know, I'll be on one customer call with a team and then I'll have like five other customer calls before I go back to that team three days later. I think you always have to provide feedback, good and bad. You always need to provide feedback and you need to ask for feedback. I asked people last night, I'm like, did I do well on that call? Did I accomplish what you need? Was there anything I missed?

Should I done something better? And then I try to do the same. But it has to be immediate. It has to be both ways. You have to ask for it and you have to provide it as well. 

Trinity: Do you document it somehow? So, the reason I'm asking is because I'm thinking whether I personally need to change structure. So, we started out with, have this Google doc where we capture every, like one-on-one on any kind of conversation.

So we have kind of like a trail of what we discuss, otherwise by next week, I'll forget everything. So I wonder if I should use that same method for like providing coaching and feedback and document it there. I don't know if you have any tips or like practical tips that you've done that you've seen 

Jerry: work.

Trinity, you've had a lot of success. I don't think you forget anything. What we do is we do a one-on-one document and so we both can input into it. And by the way, I do this with my team. I do this with my CEO. Every leader on my team does it. This is standardized. So we do a one-on-one that we go to.

I think it's impossible – I shouldn't say impossible – it would be really challenging to document every piece of coaching you did. If you called and said, I think we should do this on a proposal, I think you should say this, and then you send an email off. So, I think it would be hard. I think you have to do the structure, which is the career and the weekly one-on-ones. But doing the ad hoc coaching that you do, if you're doing a lot of it, which I think everyone should, it'd be pretty hard to document all that.

That's 

Trinity: true. Since you mentioned about the career, do you think – like in the old days, pre COVID, everyone does like a performance review maybe once a year, once every six months – do you think that changes now? Is it more frequently? Is it less frequently? 

Jerry: Pre-COVID, that's funny. Old days were pre-COVID, fully two years.

I've always believed in careers. I believe a company owes every single employee a career roadmap. I believe you owe it to that. Every person at our company has a career roadmap. Now, I believe it's the responsibility of the employee to execute on that and decide what they want to do and it can change.

We have always had, minimum, quarterly career one-on-ones. These are 45 minutes to an hour and 15, everyone on my team, set aside well in advance, it's for the whole year, it's planned out, and it's to talk about nothing but these. And we have a template that we follow – you know, skills, you know, areas for improvement, longterm, they want to do five years, short-term, they want to do one year. How they want to get there, what they might want to do. You can't possibly help anybody or supporting anyone, if you don't know them well enough to know what they want to do this year or next year or beyond. 

Trinity: Oh, my gosh, we just hired an HR manager and I cannot wait.

And, like, can we have that template that Jerry talks about? Can we have more 

Jerry: structure? Yeah, Trinity, you know, HR. We just hired a Head of People, a phenomenal leader that I've had the privilege of working for us. I'm so lucky that we got her. I often see that a lot of leaders will say, Hey, this is the responsibility of HR.

Hey HR, can you do this? Development of a team is the number one responsibility of every leader. How your team performs and their development. So, you know, even if it's a two-page document with a couple of bullets, Trinity, I would recommend you get started now. 

Trinity: Oh yeah, mine right now, it's just like words and words and words, like everywhere.

It just needs that something a little bit more presentable. 

Jerry: I'll send you mine. Just remind me, I'll send you mine. Happy to. 

Trinity: I will ask you for it. Thank you. So I want to be mindful of the time, so I'm going to ask you two last questions. I guess the first one would be what has been your all-time favorite sales play and why that's the case?

Jerry: Sales plays are so hard. I wish I had a panacea where I said, just do this sales play and everyone will be successful – the company, the sales cycle, the market, the ASP, the industry – there are so many different ones. I'll share one that I had recently that was shocking to me, surprising, recently. So everyone says – a lot of companies say they're customer-centered.

We're focused on the customer. We're customer-centric. So what I, one of my players was, I said, okay, for an entire week, a whole week, all of our communication, our outbound, our social media, everything will never mention our company or our products. Never mention it. Because what I noticed is every time I go into a company, any company I worked at, the first 10 slides of a 20 slide document is, you know, here's where we started, here's how many customers we have, here's how much funding we have, here's our great products. Right. And all of that's fine, except all customers really want is how are you going to solve my problem? How fast will it take you?

Can you actually solve the problem? So I was shocked how hard it was when I tried to go a week with doing no – and it was hard for me, really hard for me without naming our company or naming our products and doing nothing but focusing on the customer and a customer problem or challenges. What would I recommend to anyone? Try that sales play. Try it for a day and see how you do. If your whole team – try your marketing team, your BDR team probably, not mentioning your company or your product. Focus just on your customers and their problems. 

Trinity: So, my wheels are turning. Like, okay, I might want to do it next week. So, essentially, what you're saying from the marketing side, then all of our advertising will be about the pain points that the potential customers have.

And then for sales, then all these calls, you don't mention a product or our name. You discover, you basically talk about them. 

Jerry: Yeah, here's your customer. Here's your problem. Here's what will happen if we solve the problem? Interesting. See what result you'll get. I was shocked. It was really hard for me.

I'll 

Trinity: give that a try. We're small, you know, that we can actually try it next week. I might. 

Jerry: Let me know how it goes. You tell me how that goes and I'll send you my career development template. 

Trinity: All right. All right. So my last question and it's a fun one, easy one, hopefully. What is your number one DIY life hack? 

Jerry: I have kids and my wife really likes wine.

So do I. So, let me give you two, if that's okay. My two-year-old rolls around and jumps a lot in bed. So, if you take a pool noodle and put it under the sheets on either side of her, she doesn't flip out of the bed. So, that's my number one. If you have kids that roll around in bed a lot, that's number one. And if you like wine as much as I do, and you know, I'm from wine country in Northern California, and my wife, you'll often get in a situation where you're coming home and you've got wine, but it's not cold enough.

So, wet a towel, wrap the wine in it and it stick it in the freezer for seven to 10 minutes. Perfect temperature for you. So, I would recommend that probably both in the same night – pool noodle and the chilled wine. 

Trinity: That's a great one, especially now that I am in Miami and it's warm all the time and I love wine. I will definitely use the second 

Jerry: tip.

Trinity: Absolutely, Trinity. I hope it helps. This is great. Thank you so much. Just to wrap up the conversation. Do you have any words of encouragement for revenue partitioners out there that are listening? 

Jerry: Yes. The first thing I'd say, the first hundred days is critical, number one, and it's important, but also I think it can be very impactful. So what I'd say to all of these sales and marketing and revenue leaders out here, I would just keep it simple and I'd say believe in yourself, right?

I know that sounds simple and so it sounds crazy, but believe in what you've done, believe in how you've done it. Believe that you got hired for very specific reasons. There's going to be plenty of people out here who don't understand why you got hired, doubt your background, all that. Just believe in yourself and what you think will become.

Christian: I think that a lot of what he said felt super relevant to me right now. Like the fact that, ultimately, the consistency that you need as you're scaling your team. Like, as he mentioned, if you're hiring 20, 40 people a quarter, you need to have a process in place. You need to write down the things that in a sense matter to your organization and matter to the job and make sure that everyone has the same information.

You can't go in and teach everyone individually as these people join, as people leave. So I think as he said, the consistency starts with the onboarding. The first information that you present to them needs to be already written down and very defined. 

Trinity: Yeah, I was going to say the exact same thing. It seems, it sounds so relevant to us as we go into the hiring and scaling process.

Yeah, the consistency. Even as we start onboarding on User Gems, even though I think we do a pretty good job of documenting all of our processes in Notion, I think just reinforcing that, and that if any question, going to the onboarding doc in the Notion, it will have all the answers and processes. So 

Christian: I'm always cautious about having too many processes, too much information written down, being too structured. And I don't know if this comes from my Microsoft days where the more information you have, the more, the whole onboarding isn't just here are the documents, go study, and come back in two weeks. So, I feel like there must be this trade off between how much information is written down, how much information is collected and not overburdening the new employee.

Trinity: True. But I think you're comparing not having any processes and then everyone reinventing the wheel or creating chaos — because everyone just running in different directions versus a very, very, very well-established enterpise company. I don't think we need to worry about that part, but I think not reinventing the wheels, especially since as a startup, we need to move quickly. Having a single source of truth,

in terms of even processes, the simple things like when to create an opportunity? What does the handoff look like? These things, I think the sooner we establish, the faster that the person can run and be creative in other things. 

Christian: Yeah, but then there's this learning on the job and I, at least so far, I really like the way we did it, where it's like, okay, here's your onboarding document and now let's get started working on these opportunities and these 

Jerry: prospects. And then 

Christian: they learn through the process. They'll make some errors along the way. The question is how long that's scalable. 

Trinity: Another thing that he talks about, which I want to talk about is the ideal employee profile. I think it was so fascinating. My entire career, I just kept thinking about ideal customer profile and never thought about the ideal employee profile. It really got me thinking, especially as I start having more conversations with candidates, they ask me, well, if you think about the last two, three employees that you hired, what made them stand out, right? What is our ideal employee profile?

And I 

Christian: wonder how much does, and being, we even, we think we have an intuitive understanding of how this person should look like. 

Trinity: I wouldn't say that. I don't think we knew, but I think now that I think back, our gems who really thrive, there are common traits that we like. I think we really didn't know. We were just hoping to find the gems, right. But I think there are common traits. I think now I can kind of shape this idea of employee profile at User Gems. 

Christian: No, I think it was, I mean, at least that's the hope that we intuitively knew what we were looking for, but I mean, bringing this out, writing it down and making and thinking about this as to whole company, so that everyone knows what we should be looking for.

I think 

Trinity: it's right. Yeah, be more intentional as we talk to candidates and also be like transparent and sharing, like, this is what we're actually looking for. Frankly, it was because of the conversation with Jerry that, and then some other questions from candidates, that got me actually actively thinking about this profile and share that with other candidates and kind of use that as a framework as we evaluate 

Christian: candidates.

I like the sitting in the trenches. And I think, be the leader, once again, probably should be very intentional thinking about like, how can I sit in the trenches with like, in sales, with, let's say, my SDRs, but for me as the CEO, it's like, oh, can I sit in the trenches with marketing, with sales, with customer success. So making sure that you lead by example. 

Trinity: Marketing team will always welcome you to sit in our trenches and setting up campaigns and write blogs. Write the many, many blog posts that you owe us.

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