Boston Startup Interview: John Barrows on Sales Innovation

In this edition of our Boston Startup Series, we had the privilege of sitting down with John Barrows, the CEO of JB Sales and a widely recognized leader in sales training. With over two decades of experience, John has worked with some of the biggest names in the business world, from Salesforce to LinkedIn, empowering sales professionals with the skills they need to thrive in today’s rapidly evolving landscape. John’s hands-on approach and sharp insights into the sales profession make him a trusted authority in the field. Join us as we explore his career path, the challenges he’s faced, and his thoughts on the future of sales in an AI-driven world.

Could you share a bit about your background and what initially drew you to the world of sales?

Long story short, I got a degree in marketing, but after graduating, I wasn’t sure what I really wanted to do. I didn’t like the jobs I was finding and kind of fell into sales like everyone else, especially since back then there weren’t any degrees in sales. My first job was with DeWalt Power Tools, where I drove around giving away free tools to construction workers. Eventually, I moved on to Home Depot. At Home Depot, my job was to turn a $10,000 order into a $50,000 order, which involved more of a sales role. From there, I transitioned to selling Xerox, which is where I really got my formal sales education. Xerox essentially defined solution-selling in the late '70s and early '80s. I even sold to the government, which, selling copiers to the government, was pretty brutal.

But that’s where I cut my teeth. Later, I started a company called Thrive Networks with some friends, where we outsourced IT services to the SMB market here in Boston. I took every training I could, including Sandler, Miller, Hyman, and TAS. During that time, I came across Basho Technologies, one of the first sales training programs I genuinely liked. I used their training to help grow Thrive, and we became the fastest-growing company in Massachusetts for a few years in a row. Eventually, we sold to Staples. I spent about a year going through that integration, but I didn’t really fit in with the corporate culture. So, they offered me another position, and I decided to go off on my own.

Then I joined Basho, the training organization. Not because I wanted to be a trainer—I actually didn’t like trainers up until that point because most of them were failed sales professionals or just professional presenters. But Basho had a unique model where you had to sell to train; you couldn’t just be a trainer, you had to use the techniques to sell. So, I joined them, took on some larger accounts, and eventually, to make a long story short, they screwed it up, and I took it over.

So, in 2010, I went off on my own with JB Sales, took my clients with me, and have been independent ever since. But I still sell every day too. I think the key to why my content and training resonate with sales reps is that I tell them, "I'm not a trainer; I’m a sales rep who happens to train." I still prospect every day, negotiate my own contracts, manage my own accounts, and handle all my social media and branding.

What I’ve noticed lately is that a lot of people have gotten lazy over the past few years when interest rates were low and money was free. They didn’t focus on the fundamentals. Now, we have a generation of sales reps who lack the fundamentals, and they're falling apart. We turned them into robots, and now AI is taking over their jobs because it’s doing it better than most reps can. So, I’m out there, trying to figure it out just like everyone else, but I’m actually out there doing it, instead of just telling people how to do it based on how I was successful five years ago.

You mentioned it a little earlier, but what motivated you to start your own company, and what were some of the challenges you faced in the early days?

I usually tell people that I’m more of an opportunist than anything. If I’ve been blessed with something, it’s the ability to look at a situation, and without over-analyzing, make a decision based on a couple of data points. That’s how it happened. When I went off on my own, it wasn’t a conscious choice like, “Oh, I want to start my own business.” I always felt I could, but I didn’t know how to do it.

When Basho fired all of us, I didn’t have much of an option. There were about 20 employees, and when the CEO walked in and said, “That’s it,” most people had the typical reaction of, “Oh my God, I don’t have a job. I don’t have healthcare. I need to find a new job and update my resume.” But I looked at it differently. The CEO had just walked away from what used to be a $4 million business with a product everybody loved and a revenue stream already in place. So I thought, “Who’s coming with me?” I brought everyone back to my house and said, “Guys, this is a huge opportunity. Nobody gets to start a business with a proven product, a client list everyone would kill for, and a revenue stream already in place. Let’s go.”

It ended up being me and two other trainers, although we eventually let one of them go. So it was just me and my business partner. The challenges were the usual—trying to build the business while riding the bike, so to speak. But at that point, it was more of a money grab, an opportunistic play rather than a fully formed business. We were just two guys under one umbrella doing our own thing.

I quickly realized that my business partner and I didn’t see eye-to-eye on a lot of things. My advice to anyone starting a business: never start one with someone who does your same job. Don’t have two sales reps start a company, or two operations people, or two finance people. No matter how good the relationship is, you’re always going to look at each other and think, “I can do your job better,” especially in sales. So, we butted heads quite a bit.

When I finally decided to go off on my own, I already had my operations sorted. The woman who handled operations and finance at Basho was doing my books in the background. She wasn’t just an admin; she was like a COO/CFO. I told her, “If you help me out now, one day, when I have enough money, you’ll be the first hire I make.” When I finally earned enough, I called her and said, “Megan, get over here.” It was probably the best decision I ever made. She took over operations, finance, invoicing, billing—all the stuff I could do but didn’t like. That freed me up to go out there and sell.

As a sales trainer, if you can’t sell your way through different economic conditions, you shouldn’t be training others. The struggles are the same as everyone else's: I have to find new business, and all that. Long story short, I grew the company to about 20 employees and $6 million in revenue. But then 2023 hit, and all our clients were in SaaS. It came to a screeching halt. We went from $6 million to zero within a couple of months.

I had to restructure everything. I couldn’t save everyone, and I had to let some people go. I ended up splitting the company in half, giving one part to my business partner, and offering the rest 1099 contracts. Eventually, it was just me and Megan again. I realized I had built a business because I could, not because I wanted to. Now I’m back on my own, doing my thing, and I’m happier for it. I’ll probably never hire another employee again.

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‍I’d really like your opinion as a fellow salesperson. How have you seen the sales profession evolve over your 25-year career? And what role do modern tools like AI play in today’s sales landscape?

Everything fundamentally shifted when AI showed up. Every industry is living in a legacy model right now, but we don’t know what the future model will look like. The future I envision for sales reps is that they have to be like Iron Man or Iron Woman. You need the foundational skills of a sales rep—business acumen, the ability to have meaningful conversations, and the fundamentals. But you also have to know how to use technology and AI. Think of Iron Man: Tony Stark is just a human who’d get killed by the aliens without the suit. The suit was good, but it was just a chunk of metal without J.A.R.V.I.S. He didn’t really become Iron Man until he combined all three elements.

Products themselves are commoditized. I don’t care what you sell or who you sell to—there are 50 other companies selling the same thing. Telling me your product is better or your people are better is a joke. What we need to do is solve problems and add value at every stage of the sales process. When it comes to AI, the trouble is obvious. All you have to do is go into ChatGPT and pretend to be a customer. For example, I could go in and say, “I’m the VP of Sales for a 50-person team with 20 SDRs and 30 AEs. We’re struggling with top-of-funnel and deal advancement. How does JB Sales compare to its top three competitors? What are the pros and cons?” In five minutes, I’d get better and more personalized information than I would from a sales rep stumbling through bad questions and an irrelevant demo.

In my view, this is Pareto’s Rule: 80/20. AI won’t replace sales reps, but sales reps who know how to use AI will replace those who don’t. Unfortunately, that’ll only be about 20% of the population, and the rest are going to get smoked. And it’s going to happen faster than most people realize.

Every other technical advancement has kind of evolved a little bit: the iPhones, high-speed Internet, that type of stuff. This is hockey-stick, so it's just learning on its own, and it's already better than we are.

Yeah, I'm seeing that in my field as well. Junior developers are really struggling to get a job because the most advanced ones, the ones who know how to use all the tools, are getting all the shots. So, the demand has decreased, and there are also guys with a lot more productivity due to AI than the ones that are just getting started.

I mean, you've got autonomous things right now. You can do fully automated SDR outbound and inbound campaigns that are truly personalized to prospects, respond faster, give better information, create more personalized emails—everything. It's pretty obvious to me where things are going, but there’s still, I’d say, 95% of the population that is not paying enough attention to it.

I believe fields like development are hitting a wall. Two or three years ago, developers were rockstars. They came to an interview wanting to earn a lot of money and not work a lot, and now they're really struggling to get a job. So, I believe they hit a huge wall.

Yeah. No, there's no question about it.

What key principle do you believe separates a successful sales team from those that struggle? And I’d like to add a personal one: Do you believe anyone can be a salesperson with the right training, or is it just for some people?

Successful sales teams work as a team. Sales is often known as a one-man solo show, like, “Hey, let me go out there, hunt, kill, and do my thing.” But the likelihood of that surviving moving forward, and the company or team surviving with that mentality, is not high. I personally think you've got to turn every sales org into a sales lab right now and just keep testing and trying new approaches. Because what worked six months ago isn’t working anymore. If we bring it into the developer world, it's kind of like how developers have hackathons, right?

I think sales reps should have hackathons too. On Fridays, teams should get together and pick one aspect of the sales process they’re struggling with, whether it's discovery, preparing for meetings, updating the CRM with information, creating personalized messaging, business cases—whatever. Then break into groups, and assign the task: whoever can find a solution or process that’s better than what we’re doing now, using AI or whatever, wins the day. Then whatever that thing is, you implement it the next week, test it, see if it works. If it plugs into the process and makes an improvement, keep it. If not, pick another thing.

So if you're not constantly iterating and becoming an agile sales org right now, you’re going to get replaced by robots, easily.

Your second question was: is anyone a sales rep? Yeah, everyone’s in sales. The problem is the perception of sales versus the reality of sales.

Sales isn't about convincing anybody of anything. It’s about helping people solve problems or achieve goals. That’s it. So I could take the most introverted engineer on the planet, who swears up and down they’re not in sales, and I promise you, they are. Somebody once told me earlier in my career that sales is the transfer of enthusiasm—and by the way, I think the number one thing you need to be successful in sales is belief in what you do. If you don't believe in what you do, go find something else to do. But when you believe in what you do, passion and all that other stuff follow, and it’s a transfer of enthusiasm.

So I can take the most introverted engineer, who swears they’re not in sales, and say, “Cool, no problem. Can you explain the last time you found something wrong in code and fixed it? Or tell me about the last thing you created that made an impact on the business?” And you will literally watch them light up like a Christmas tree. They’ll start talking like, “Oh, the other day I was deep in this code, and I found this thing, and I did this, and it was able to do that.”

And guess what? If I needed what you just said, I’d want it. That’s why everyone’s in sales.

Now, the perception is that sales is about being a slick-ass rep who’s got to convince you to do something, using all these techniques and tricks to get you to buy my sh*t. That’s 1985 all over again, Wolf of Wall Street. Fine, but that’s Glengarry Glen Ross. Unfortunately, those movies have created the perception of this profession. That’s why customer success and sales are far more closely aligned than people think. We’re both trying to help clients solve problems and achieve goals. Sales is about getting them to buy our stuff, and Customer Success is about getting them to use our product to solve those problems.

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What do you think are the key skills young professionals need to develop in order to successfully transition from junior to senior roles in sales?

Grit and business acumen.

Grit—I mean, most people don't have the work ethic to be successful in sales. This isn’t a nine-to-five job. This isn’t a “I’ll wake up whenever I feel like it” type of thing. Sales is one of the harder jobs out there, especially in B2B. You’ve got to be okay with 99% rejection.

The other thing is business acumen. You can learn all the techniques, skills, and read all the books. But the number one thing reps need to do to improve their results is to improve their business acumen—learn to have conversations and be a problem solver, not just a sales rep. Because if you can be a problem solver—and sometimes, frankly, the problem the client has isn’t one you can solve, and that’s okay—but if you can bring value to the table, when they do need your product, they’ll come back to you.

So that’s the shift, right? Again, techniques and all that stuff—anyone can learn that. ChatGPT can tell you every technique on the planet. It’s more about giving a sh*t and really caring about what you’re doing.

I tell reps all the time, “I can’t get you to give a sh*t, but if you do, I’ll give you everything you need.” But you have to care. And when I say giving a sh*t, I mean caring about the client you're talking to. Think of them as more than just a phone number or an email in a cadence—think of them as a person who’s going through the same challenges you are, who wakes up every morning and has their boss yelling at them. How can you help them solve problems? That’s what the best sales reps do, and how they graduate to becoming great reps.

What positive aspects or characteristics have you noticed about the Boston startup ecosystem as a founder?

I think Boston’s a great city in general. The ecosystem here, if you look for it, is there. There are people, there’s support, communities, everything. But I think the biggest thing about Boston is the no-bullsh*t approach, right? We’re not trying to screw around with people. If I don’t like you, I don’t like you, and I’m not gonna beat around the bush about it. You get hard answers, and sometimes they’re a little harsh, but they’re good learning lessons. I’d much rather get to the point and talk to somebody than spend an hour beating around the bush.

It depends on your industry. Biotech is huge here, finance is more New York, and there are a few industries that are strong in Boston. But when it comes to B2B, SaaS, and tech, it's not like San Francisco. SF is a lot more startup-friendly and supportive, and I think Boston is getting there. But Boston is one of those towns where you have to earn the right to get in.

Anybody can go to San Francisco, sit in a coffee shop, bump into somebody, and start a conversation. And then suddenly the funding happens because they fart money out there and throw it out the window for no reason. They waste a lot of it. But here, you don’t get into my circle until you earn it. It’s a lot harder to get into the circle here in Boston, but once you’re in, people will die for you.

The analogy I use for East Coast versus West Coast is: Bostonians are kind, but not nice. West Coasters are nice but not kind.

Here’s the difference. If you’re on the side of the road and your tire pops, and AAA isn’t coming, you have to fix your tire. Somebody in California will sit there and commiserate with you. “Oh man, that sucks, you have to change your tire, that’s horrible.” They’ll talk to you about it, but they won’t do sh*t about it. They’re nice, but they won’t help you.

Whereas here in Boston, if you’re changing your tire and I see you doing it wrong, I’m pulling over. “You f*cking idiot, get out of the f*cking way,” and I’ll berate you the entire time while fixing it for you. Because I’m not leaving you on the road to get hit because of the stupid sh*t you're doing. So we’re kind—meaning, we’ll help—but we’re not nice. I’m not going to sugarcoat it for you.

I believe you mentioned the challenge of getting into the circle in Boston, but are there any other challenges you’ve faced in the market, and how did your company overcome them?

I was born here, so you’re almost asking the wrong person. I fit right in. I know the mentality of the city and how to manage people here. You just have to put in the effort. Go to events, put yourself out there, help people out. You need to have that giver’s gain mentality. It’s not about always trying to get something from someone. You have to be honest and authentic. People here can sniff out inauthenticity in a heartbeat. If you’re not authentic, nobody’s going to engage with you in a meaningful way. If you're full of sh*t, this isn't the city for you.

You have a large and engaged following. How do you approach building that community, and what do you think resonates most with your audience?

Authenticity, period. It's about sharing what I've learned, not telling people how smart I am or dictating what they should do. I share my journey and what I’m learning along the way—end of story. I try to add value in every interaction, conversation, and post. If it’s a thinly veiled attempt to push you into buying my sh*t, no one’s going to connect with that. If I want to sell my sh*t, I’ll be direct: “I want you to buy this because of this reason.” But if I post for thought leadership and then push an ebook or a webinar, people won’t engage. You need to share your journey, be authentic, and share what you’re learning—not what others should do.

When my team posted, they’d say, “This is exactly what I’d do,” and I’d stop them: “Don’t tell people what to do.” What worked for you doesn’t necessarily work for them. Share what you learned, how you applied it, and how it worked for you. Don’t tell people this is the one way to success or toss around generic hooks like “the top five keys to success.” There's no perfect question or strategy—it’s about working hard, sharing information, being authentic, asking good questions, and giving a sh*t.

Finally, what advice would you offer early-stage startup founders in Boston?

Get out there as much as possible and learn how to sell your sh*t yourself. Don’t hire a sales rep thinking they’ll solve your problem if you can’t sell it yourself. The “Founder’s Dilemma,” especially with technical founders, is thinking their product is the best and that it will sell itself. It won’t. No matter how special your product is today, it won’t be tomorrow. It's not what you sell, but how you sell it that matters.

What often happens is that founders, especially technical ones, are the first sales reps. They usually pitch to audiences like friends, family, and fools, and because of their passion, they manage to sell a few products. Then they think, “This is easy!” and hire a VP of Sales. But that person doesn’t have the founder’s passion, knowledge, or network, and they fail because there’s no process or insight built in.

The founder then decides that sales is a joke and turns to marketing, which works up to a point. Eventually, they hit a wall and realize they need sales again. If you see sales as a secondary citizen in your company, you will fail—period. Most companies don’t fail because their product is bad; they fail because they can't sell their sh*t. If you view sales as second-class, you’re setting yourself up for failure. Sales is critical, and nothing happens in a company if someone isn’t selling the product.

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Whether you’re navigating the current economic challenges or trying to upskill your team with the latest sales strategies, John’s expertise can help. If you want to learn more about his approach or take a look at his content, don’t miss out on his newsletter and sales training for individuals and teams. 

Are you a CEO or founder in the Boston area? We’d love to hear your story. Reach out to be featured in our series and share your insights with the community.

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