Scale Like a CEO

Fearless Growth: Rob Henderson on Innovation, Leadership, and Scaling Jump Crew

• Justin Reinert • Season 1 • Episode 23

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The landscape of B2B sales and marketing has fundamentally changed, yet many companies still rely on outdated approaches. Rob Henderson, founder of Jump Crew, is on a mission to revolutionize customer acquisition through fearless innovation and integrated strategies that actually deliver results.

Rob's journey began as co-founder of tech company LocalVox, where he developed a unique sales and marketing approach that led to a successful exit. Reflecting on what worked, he launched Jump Crew in 2016 to offer these specialized capabilities as a service. Today, the company serves major clients like Experian, Nextdoor, and Airbnb through an integrated model that combines data, content, lead generation, revenue operations, and sales under one roof.

What makes Jump Crew distinctive is their rejection of "mindless outreach" that dominates so many sales strategies. Rob explains that randomly calling or emailing hundreds of prospects simply doesn't work in today's nuanced B2B environment. Success requires a deep understanding of data, compelling content, and strategic alignment across all customer touchpoints - exactly what Jump Crew delivers through their five interconnected service lines.

Building the company wasn't without challenges. Rob candidly shares how they overcame initial market skepticism and spent years identifying their ideal customer segments. As the team grew to hundreds of employees, he developed a leadership philosophy centered on psychological safety, autonomy, and clear communication. He prioritizes hiring for three critical traits: commitment to psychological safety, collaborative spirit, and coachability - qualities that have fostered impressive organic growth within the organization.

Looking ahead, Rob remains committed to pushing boundaries and challenging status quo. While many successful companies become risk-averse and resistant to change, Jump Crew embraces a fearless approach to innovation - constantly testing new methodologies to drive customer success. Ready to transform your approach to revenue generation? Connect directly with Rob at Robert@JumpCrew.com.

Rob Henderson:

to push the boundaries of innovation on how we think about customer acquisition, and if there's a new thing, we're going to test it and we're going to develop it and we're going to integrate it, and we're going to do that fearlessly. I think a lot of companies, when they become successful, they sort of go like, oh gosh, what we're doing is working and we don't want to change anything because it might be risk or whatever. And that's how products become stagnated and stop working. And so the future of Jump Crew is really to be the innovator in our space, to challenge status quos, to be comfortable doing things differently than other people, because, ultimately, driving success for our customers drives success for our teammates.

Speaker 2:

Welcome to Scale Like a CEO the podcast where we dive into the strategies and insights of successful business leaders. We're excited to bring you today's conversation with Rob Henderson, an accomplished entrepreneur and the founder of Jump Crew, a company that's revolutionizing how businesses approach sales and marketing. Join us as we explore Rob's journey in building and scaling companies, his unique approach to leadership and the innovative solutions his team is bringing to the market.

Justin Reinert:

Rob, thanks so much for joining us on Scale Like a CEO. Just to get us started, give us a 90-second intro to you and your business.

Rob Henderson:

Sure, my name is Robert Henderson. My first job is being dad to two little ones, a 10-year-old named Benjamin and a four-year-old named Theodora, also, proud to say, a husband of 20 years, so that's been a fun journey. Originally from Peruvian New Yorker background, but I've lived in Nashville for seven or eight years, so that's pretty unique. I think that makes me a unicorn for sure. Started Jump Crew through another experience.

Rob Henderson:

I was a co-founder in a tech company called LocalVox and, pretty young at that time, had the opportunity to help grow that business and eventually exit that business. And when I had some time to think about what we did really well over the years, about what we did really well over the years, I reflected on the fact that we had a really unique sales and marketing customer acquisition process and so I wanted to offer that unique capability to other companies as a service. I had the opportunity to start Jump Crew in. I guess it was like the fall of 16. Been going ever since. We now serve some of the world's largest companies like Experian and Nextdoor and Airbnb and so on and so forth. So it's been a really gratifying journey and kind of glad to see it's being put to good use.

Justin Reinert:

That's great, rob. I'm curious what is the biggest problem that you see in your industry today and how are you solving that?

Rob Henderson:

Great question. I think the biggest problem in our industry today is that people try to solve the problem of revenue generation through making more mindless outreaches whether that be emails or phone calls or DMs and the reality is that the way that commerce works today, especially in the B2B space, is a lot more nuanced and requires a lot more than just dialing for dollars. There's always a component of dialing for dollars in every business, but having a strategy that encompasses a really good deep understanding of data and content and media and really kind of like understanding how to align that with your customer acquisition strategy altogether in an integrated process is really what works. And when I see people failing, it's usually because they think that calling 100 people randomly is going to get their product sold, when the reality is it is not.

Justin Reinert:

Yeah, I would have to say as a business owner myself, sales today is definitely challenging and continues to become more nuanced. And what works changes, I swear like monthly almost. So what makes you unique in the way that you're helping others?

Rob Henderson:

I really think that it is our integrated approach. So at Jump Crew we have five product lines data, content, lead generation, revenue, operations and sales. We're the only company that I know of in that space that does them all together. So I think, like agency meets RevOps, consultants meets sales outsourcing, we do that all under the same roof, which I think is pretty unique and drives the type of results that our customers are looking for.

Justin Reinert:

Yeah, I think that is unique. It seems that there's a lot of agencies that do one or two of those things, but not many that do all of that. So let's transition a little bit. Let's talk about how you've grown the business. So, if we rewind to 2016, 2017. And thinking about how you approached growth within the business, what were some of the challenges that you faced early on in kind of getting everything up and going?

Rob Henderson:

Man, there was a lot of challenges. The world was rife with challenges. I think anytime you're trying to do something a little bit new and different, there's always a lot of skepticism. Time you're trying to do something a little bit new and different, there's always a lot of skepticism. So overcoming that skepticism with data, facts and results was definitely a big challenge.

Rob Henderson:

It's sort of like if you're a young person and people are asking you for experience in your role and you're like you don't have any, but at the same time you haven't had enough time to have any and you just want to roll, you're in this conundrum where it's like you know you could be successful at something but you don't have a track record to prove it. And I think for early stage businesses, that's always a conundrum, especially if you haven't been around for a long time. That was a really big challenge in scaling. And then I would say the other really big challenge that we had is really just knowing who our customer was. And that took us several years and we tried across a lot of different verticals, a lot of different business sizes before we found a really sweet spot for our business. And so I think that trying to be all things to all people is often very difficult and doesn't lead to success. But the day that you find a business set where you're driving really positive results for that's when you become successful.

Justin Reinert:

Yeah, for sure, for sure. Getting that market kind of zeroing in and being specific about the market that you're selling to is definitely critical. I've talked to a lot of founders about that. I'm curious as you've grown, you've grown to your few hundred employees now. I think so, as you were in the early stages of starting to add people to the team. Some founders find it challenging to transition from being a small team to adding more people and making sure that we've got the right fit and then continuing to grow and build on that team. Tell me a little bit about that experience for you, as you were adding people to continue that growth.

Rob Henderson:

Yeah, it's always interesting. As a founder especially, you want to be able to influence the culture and have input and have insights while, at the same time, culture and have input and have insights while at the same time, not micromanaging the leadership team that you've brought on to lead. And it's very hard to lead if you have a founder CEO breathing down your throat, especially if you're going around them. So I was very of that fact and really focused on how I could be constructive and communicate some of the fundamental principles of the business at all times, but not get into the super tactical details that I wanted my leadership team to have the autonomy to do themselves. And so it's all about straddling this line of not totally going away as a founder and seeming aloof, but also not micromanaging people to the extent that you're doing their job. And so my strategy and I like to think that it's worked I don't know you'd have to ask my leadership team, but my strategy is really to create a safe space for people where they feel like they can come to you with questions or comments or concerns that they have and just share them with you and then create an environment where you ask good questions and help them come to the decisions that they want to, or they should come to themselves and then be a guardrail for them.

Rob Henderson:

They don't make really bad ones, or try to, because we always make really bad decisions sometimes but to try to be a guardrail to not make the bad ones, and so that three-step process, I think, served me pretty well. My team works with a lot of autonomy. I'm not like the dude that's going to be in there every five minutes trying to tell them what to do. I really sort of pride myself in just sitting here being available to help make good decisions.

Justin Reinert:

I love that you brought up the idea of safety. It's so critical and I had someone on the podcast a month or two ago. He was the former CEO of Pitney Bowes and had such a great conversation with him talking about the concept of psychological safety that you know he was doing it before the term had really been coined, psychological safety. So I love that that's something that that comes up for. You is giving that autonomy and making sure that people feel safe to fail, that, knowing we all make mistakes. I think that's so critical. So, as you continue to grow, what are some of the key traits that you look for as you're adding to the team?

Rob Henderson:

So somebody who will continue to perpetuate. Psychological safety is an important one. I find that an environment where people just feel free to be completely open is probably going to be a thriving environment, a successful one. When people start getting siloed and being worried about what the next person is thinking about them or what they're going to say or whatever, it really becomes very, very challenging, and so creating that psychological safety is something that I need our leaders to be on board with at all times. So that's one thing.

Rob Henderson:

Jump Crew is a very collaborative environment. We tend to be the place we always say Jump Crew is a team sport, so we tend to be the place where I described the five products to you earlier. It's like they all need to integrate seamlessly. That's complicated. Things need to talk to each other from a systems technology perspective, from a human's perspective, from a workflow and processes perspective, so it needs to be a team sport, and so the other thing that I really look for is collaborative spirit.

Rob Henderson:

Not everyone has to be that person.

Rob Henderson:

Some people prefer to work on their own and be lone wolf types, but at Jump Crew, you're going to be more successful if you're a collaborative person, and so that's one of the traits that I really look for.

Rob Henderson:

And then the third trait that I look for is just coachability. It's really hard to work with somebody who just doesn't take input, and coachability happens in a ton of ways, right. Sometimes your team, somebody that reports to you, can coach you from their position, and sometimes your manager needs to coach you from their position. But at the end of the day, I think there's personality types and there's people who are open to dialogue and discussion and will digest and take feedback in, and there's people who just won't, and the latter is just incredibly difficult to work with, even from above or below, just for anybody. It's just hard to work with somebody who's just not willing to listen to feedback, and so those are. That's another aspect that, just from almost like a lifestyle perspective, if you're going to work with somebody, you want to work with somebody who wants to have a two-way conversation and listen to feedback, as opposed to completely uncoachable and just going to do their own thing.

Justin Reinert:

Coachability, I think can be often underrated or not even considered in that initial hiring phase. It comes up later, right when somebody doesn't have that quality. But I've worked with so many leaders who want to hire for technical skills first and they don't probe around those other things and then they get someone on board and realize, oh wow, I guess I should have screened for something like coachability or someone's ability to take on feedback. So I think it's great that you are looking at those things straight away as key qualities that folks need. Now, getting to the size that you're at, I would assume that you've got to have some engine for organic growth. You can't kind of hire, continue hiring in your leadership externally. There's got to be some organic growth there. So I'm curious how you've made that pivot. It sounds like some of your first leaders were probably external and then, and then I would assume you've got some organic growth. Tell me about how you've approached that.

Rob Henderson:

Yeah, absolutely, I'm really proud of our organic growth. A lot of us started out here together just kind of trying to figure it out, and have become executives of a relatively good sized company through organic growth and through learning. So some of that comes back to just an eye out for the coachability and understanding that hey, I can talk about it in the first person It'd be really hard to be a good CEO of a company. That's completely different at 400 people than it is at 100 people, than it is at 300 people. You have to be coachable along the way. You have to, in my case, listen to your peers and listen to people who have done it before you and take that advice and take that coaching, seek that advice right.

Rob Henderson:

And so for us, along the way, it starts with, I think, what we did a good job of finding people that were coachable at the very beginning and then, along the way, we created an environment where they could be coached and got them some resources to coach them up along the way, some of that being me, some of that being outside parties and some of that being a learning growth culture and that really enabled us to grow together as a senior team, enabled us to grow together as a senior team and then, along the way, every time we got to a wall, every time we started hitting a wall and saying, hey, we just don't know how to solve this problem.

Rob Henderson:

We were more experienced or had a different capability than we did, and as those people joined the team, they up-leveled us every single time and helped us get better, and they coached us again, whether from a reporting capacity or a manager capacity. They coached us into all becoming better. And so I think it starts with the coachability, but then it also comes with humility, of being able to understand that when you can't solve a problem, you need to bring somebody from the outside that can help you look at it in a different way.

Justin Reinert:

And what structure do you have in place to support that growth? What systems are making sure that you're looking at your talent and kind of growing them internally.

Rob Henderson:

I think a lot of it pretty bespoke. Really, the best system for doing that is having managers that will advocate for their people, and that's a pretty organic way of doing it. No-transcript needs some helping and advancement opportunities based on the fact that they're successful in their role and if we keep investing in them they can be more successful either in that role or in more senior roles. So our case, you know, it's really been more of a kind of organic, bespoke strategy to get that done. And that doesn't mean that we don't have a people team that, you know, does nine box exercises and evaluates all of our opportunities and so on and so forth. But in actuality, really, it's been that organic, bespoke strategy that's really been the most successful for us.

Justin Reinert:

Yeah, that's great. So, as you look forward, what's your vision for the evolution of Jump Crew?

Rob Henderson:

My vision for the evolution of Jump Crew is always to deliver the best product known to our industry, and anything else is not enough. It's you know, if we have a data product, the data has to be the best data. If we have a contact product, the content has to be the best content. If we have a lead gen product, and so on and so forth. And being maniacal about quality of delivery and quality of product always leads to good things, it always leads to success, it always leads to workplace enjoyment and so on and so forth. And really, if you hire the people around you that share that value of driving success for your customers, I think that's a lot of fun and it leads to a lot of enjoyment in the workplace.

Rob Henderson:

And so the future of Jump Crew is really about continuing to push the boundaries of innovation on how we think about customer acquisition. And if there's a new thing, we're going to test it and we're going to develop it and we're going to integrate it and we're going to do that fearlessly. I think a lot of companies, when they become successful, they sort of go like, oh gosh, what we're doing is working and we don't want to change anything because it might be risk or whatever, and that's how products become stagnated and stop working. And so the future of Jump Crew is really to be the innovator in our space, to challenge status quos, to be comfortable doing things differently than other people, because, ultimately, driving success for our customers drive success for our teammates, and that's what we're here to do.

Justin Reinert:

Yeah, keeping with status quo is absolutely the enemy of moving forward and growing into the future, being future oriented. Well, rob, thank you so much for joining me today. If folks want to get in touch with you, what's the best way to do so?

Rob Henderson:

Robert at JumpCrewcom. That's easy. It's pretty easy, right? That's their superpower. You get to pick your email address.

Justin Reinert:

Great. Well, Rob, thank you so much for your time today All right.

Rob Henderson:

Thank you very much.