Sales trainer John Barrows on selling in the world of SaaS

You may not know John Barrows by name, but if you've chatted with sales at some of today's fastest growing startup companies, you're familiar with his work.

John is a sales trainer and consultant whose client list includes the likes of Dropbox, LinkedIn, Twilio, Salesforce, Bitly, New Relic and my team at Intercom. His mission: Show companies how to buck the sleazy sales stereotype and make the sales experience, like any other customer interaction, personal at scale.

I hosted John on our podcast to chat about when a startup is ready for a dedicated sales team, how to better align sales and marketing, the traits that make for a promising sales hire, and much more. If you enjoy the conversation check out more episodes of our podcast. You can subscribe on iTunes or grab the RSS feed in your player of choice. Below is a lightly edited transcript of our conversation.

LB Harvey: John, welcome to the show. To get started, can you tell us how you got into sales, software and ultimately found your way into the training role you’re in today?

John Barrows: It’s a similar story to most sales professionals. Sales is the most undereducated profession on the planet. By that, I mean there’s about 4,000 colleges in the United States, and you can get your degree at less than 30 of them in sales. I fell into it, just like everybody else. I started with marketing and then I realized that I didn’t really want to do that, so I got into sales by selling power tools with DeWalt. DeWalt was my first job out of college. It was positioned as sales but it was really more event marketing. I drove around a Dodge Ram pickup truck, giving away free tools to construction workers. Then they promoted me to (the Home Depot account).

Home Depot had to buy DeWalt but my job was to upsell them, to take them from a $10,000 order that they had to spend to a $50,000-100,000 order. Then I got into Xerox and that’s really where I got my full sales training and education. Selling copiers is about as brutal as it gets, and Xerox had a really good training program as well.

After that I started an outsourced IT services company with a few buddies of mine from high school. I did outsourced IT support for the SMB market and, not knowing what I was doing, I took every training there was – Sailor, Miller Heiman, all of the main sales methodologies. I came across one called Basho, which I really liked because it was tactical and it wasn’t just theory or anything like that. I used it, grew the company and sold it off to Staples, then went and joined Basho. Not because I wanted to be a trainer, but because I really loved the training and I knew it made a difference.

To make a very long story short, I went off on my own and am now working with companies like Salesforce, LinkedIn, Dropbox, and Intercom, and teaching techniques, skills and process around how to do sales right and how to buck the trend of the sleazy sales rep who is just trying to sell anything to anybody. I’m a big believer that sales, when done right, is one of the best professions on the planet. When done wrong, it’s one of the worst.

LB: We at Intercom have hugely benefited from your training and have loved the way that you approach sales in a really personal way. You’ve worked with a number of really interesting companies, and I’m curious, whether it’s Dropbox or or New Relic, each of these companies have their own culture and unique ways of working. What have you learned from observing the way these sales teams work that’s really pushed your own thinking?

There has
to be that engagement factor that guides the customer.

John: That’s one of the reasons I love working in the SaaS world. Most of the companies I work with are in SaaS, not that this is SaaS-based training, but I enjoy it because typically SaaS tends to push the envelope not just when it comes to technology obviously, but also when it comes to sales. As an example, if I’m training Salesforce on the same stuff I was training them on two years ago, they’re not renewing my contract. I have to stay up to date on what’s happening, because these companies push so hard and so fast to grow.

I’ve learned a lot in this world and by being around sales professionals, sales leadership, and organizations who are trying to figure out sales.

I think a lot of what’s lacking right now is the fundamentals. A lot of people are looking for too many quick fixes through technology to solve the sales problem. I’m also seeing people trying to avoid sales altogether, because they think marketing automation can do it with customer success on the other end. To a certain degree some of these companies can do that, depending on what the product is, but at a certain point, you have to involve sales. There has to be that engagement factor that guides the customer through the right process and asks the right questions and helps them make decisions.

That’s why I say, “When sales is done right, it’s the best profession on the planet. When done wrong, it’s the worst.” When you see companies who are just volume-oriented, trying to cram stuff down people’s throats, it only works to a certain point. When you have a true sales professional that has the customer’s best interests in mind, that’s where the whole thing really works well.

Software sales in a self-serve marketplace

LB: Since you’ve had such a broad purview, how has the role of sales and the skillset that’s needed changed in a business that is increasingly more self-serve? And where do you think sales should and should not play in that world?

John: It goes back to what we’re selling. If you’re selling something that has a super low Average Contract Value (ACV), $1,000 for the year, it’s hard to justify having sales in that equation whatsoever. But, if you’re in somewhat of a complex sale that involves a sales cycle that’s more than 20-30 days, and at least two or three calls with multiple people, sales is a critical part of that to make sure it goes right.

You can only automate and educate people so much before they want to talk to somebody. Maybe $5,000-10,000 is when people get more uncomfortable putting their credit card online and buying without talking to people, but there’s still a threshold there where somebody’s like, “Yeah, I need to talk to somebody.” The question is, is that a customer support person or is that a salesperson?

A while back there was a LinkedIn post by a CEO, titled (along the lines of) “I’m never going to hire another sales professional as long as I’m in business”. His point was that sales reps are incentivized for all the wrong reasons. It’s monthly quotas and all these things, which really forces it to be about the company and the sales rep, not about the client. What he’s saying he’ll do is marketing automation. Educate the market as much as possible, and then when that person raises their hand, have them talk to customer service instead of sales.

It exploded with people’s opinions. One half of people were saying, “Yeah, right on, I totally get you,” and the other half were sales reps saying, “Screw you. You’re pissing on our profession.” I commented, and said, “Everything that you just described about sales reps, is what a bad sales rep does. The bad sales rep pushes to get their commission check and hit the end-of-the-month quota, and convinces clients to do things that they’re not interested in doing.” Everything that he described about customer service is actually what good sales professionals should do. My point to him was, “It’s not that sales is the problem, you’ve just hired crappy sales reps. I’d put it more on you that you haven’t hired right.”

Removing the barriers between marketing and sales

LB: I think it’s still a common belief that salespeople should just sell and marketers should just market. What’s your advice when it comes to how a sales org should work or align with marketing?

John: It’s funny you bring this up. ZoomInfo just had a conference in Boston. I just gave one of the keynotes, and we talked about the alignment or misalignment between sales and marketing. I got into sales 20 years ago and I’ve been hearing about misalignment in sales and marketing since. Everybody’s trying to come up with a technical solution, and I talked about some very tactical things that we can do to work together as a team, because without the team approach it ends up doing more harm than good.

Right now we’re hearing a huge trend – account-based marketing or account-based selling or account-based revenue or whatever people want to call it. From what I can tell, that’s just a realization that we have to stop spamming people, both on the sales and the marketing side. If you’re selling to mid-market and above, the account-based approach where sales and marketing work together to come up with a strategy around very specific accounts, is a very valid approach. Marketing might create a little bit of a broader message to get mindshare, whereas sales is a little bit more of direct message. They tie together.

Marketing is content, while sales is context.

The challenge right now is that I see a lot of marketing pretending to be sales and sales reps doing nothing more than marketing. I’ll give you an example. Marketing sends out blast emails with a sales rep’s name on it, and they say stuff like, “Hey, I was researching your company and I noticed you’d be a really good fit for our services, and here’s all the wonderful things that we do.” When you read the email it’s obviously not a sales rep, because if they did look on your website, they’d realize you probably weren’t a good fit.

Then you have sales reps cranking out template emails as if they’re marketing, and that’s even worse. You have all these sales efficiency tools like SalesLoft,, ToutApp, Yesware, and sales reps are instead using them as sales automation tools. They’re legitimately just taking template emails and cranking them out. I fundamentally do not understand the difference between that and a marketing automation tool like Marketo or Eloqua. I can actually do that better as a marketer, because I’m going to come up with that message and I’m going to split test it and measure the results. A sales rep never will.

I start off most of my trainings and presentations with this “death of the average sales rep” routine. I say “average” for a reason. The reps who are blasting out templated emails, making generic cold calls, asking generic qualification questions and pressing play on their demos, there’s no difference between that and marketing.

Just one final point to make: Gary Vaynerchuk, he’s on top of his game when it comes to branding and social media. One of the things he says is, “Everybody talks about content, right? Content is king. Fine, if content is king, then context is god.” That really resonated with me, because that got me thinking about sales and marketing. Marketing is content, while sales is context. If we as sales professionals are not putting any context around our content, then we’re no different than marketing, and I have no idea why we’re getting paid to do what we do. That is how I believe that sales and marketing should work together. Marketing should come up with relevant, good content that sales then uses to engage with the client. Sales puts their context around it to show why it’s valuable to that account or why they’re reaching out to that account and for what reason.

When to bring sales into your startup

LB: A lot of our listeners are earlier stage startups who might have been able to get by on word of mouth very early in their revenue trajectory. What’s your view on when a startup needs to bring in a dedicated salesperson or team, and why?

John: That’s a great question. I was a startup founder, and we had no money and no funding. It’s not like I could go out there and blow a bunch of cash to try a few things. Every dollar we spent was important.

It’s funny because everybody says, “Oh, I’m not in sales,” when everybody’s in sales. I could take the most technical person on the planet, who doesn’t have any customer interaction at all, who you would never think was a salesperson, but then put them in a scenario where they start talking about something that they did or developed. Have you ever talked to an engineer about something they created? They literally light up like a Christmas tree. Right there, they’re selling, whether they look at it that way or not. Somebody told me a long time ago that sales is the transfer of enthusiasm. I believe that strongly, and that’s what engineers tend to do.

When founders develop their product or their service, the first thing they do is go out and talk to friends, family and fools, people in their circle. They’re explaining what they’re developing to a rather friendly audience, and they’re inherently going to get positive feedback. Their first few customers are like, “This is great.”

There’s then this perception that well, sales is kind of easy, because this product’s great and people give me good feedback on it. Now let’s hire a sales rep and just go sell it. Inherently they bring in a sales rep who doesn’t believe in the company as much as the founder does, someone who is really just trying to sell, and can’t transfer the enthusiasm. There’s no process around it, and so they inherently fail. Then founders say, “Sales reps are such a pain in the ass. I hate sales, I can’t figure out sales.” They’ll dump a bunch of money into inbound marketing and then realize they need sales anyways. It’s just this mess as it tries to grow.

You cannot look at sales as a necessary evil.

As far as when should you bring in sales, I think it’s after the founder goes out and takes a very thoughtful approach to (understanding) who their target audience is. Get a good understanding of what that ideal customer profile looks like. What’s the ideal customer profile look like? Who’s the persona within this that buys what we do? Is it a CIO, is it a CFO, is it a director of whatever? Is this a bottom-up sale or a top-down sale? How long would a sale take? How many meetings do you have to have with these people? What are their common objections? Who’s the competition?

You don’t have to be all that detailed with that stuff, but you have to have some type of an understanding of that before you can put somebody in a position to be successful in doing it. Then, when you bring somebody on board, the question is whether or not you bring in a senior sales rep who’s been there and done that. I’ll tell you right now, it’s rare for a startup to find that perfect senior executive sales rep that they can A) afford, and B) is going to be able to come in and execute.

If you would ask me to go back to my startup days and ask, “What’s the profile of the sales rep that I want to bring on board?” Without a ton of money, it’s usually that 24-29-year-old who’s already gone through sales training at a bigger company, maybe Salesforce or something like that, but wants to move a little bit faster and has that entrepreneurial spirit. You can give them a little bit of structure and you can bring them along to the meetings where the CEO or whoever is selling and the sales rep is there learning. Eventually that sales rep is going to make cold calls, set the CEO up with meetings, learn a little bit more and then grow into somebody who could take over those meetings. Then ideally they grow into a director or manager as the company scales.

That’s the best case scenario, but again, that’s coming from a company that didn’t have multi-millions in funding. If you have tons of funding, then go get that senior, more experienced sales executive who’s been there and done that, and has a process to implement. Have them run the show and tell you what to do. But, the one thing I will beg of any organization, and I say this not because it’s my profession, but you have to have a sales culture. You cannot look at sales as a necessary evil. It will not be successful.

I know too many companies that think their product is so awesome. Ask founder after founder or VC after VC – companies do not fail because their product sucks. They fail because they can’t sell it. The majority of companies I come across have good products, they have a good market fit, they have good people on their team, but they can’t sell it. That is what fails. If you don’t have a top-down culture as it relates to sales, one of, “Look, we respect sales. We know that sales is what drives us as a business,” and instead you look at it as this, “Oh god, we have to have sales. Let’s put them in that other room while we do our cool, fun stuff over here on the engineering side,” you’ll fail miserably.

My biggest recommendation is to have a culture that respects sales and everybody supports it. Obviously sales has to support everybody else too, but if sales isn’t supported from the top down, it doesn’t tend to work very well.

The intangibles every sales hire needs

LB: You mentioned hiring those first couple of sales folks. What are some of the most important intangible elements or characteristics that you look for or find in top sales folks?

John: Passion and work ethic. Those are two things you cannot train. I worked with Jack Welch of GE for a couple of months to get his online MBA program off the ground, and when I started my first company way back in the day, Jack came to Boston to do one of his conferences. There’s a thousand people in this seminar that he was doing, and it was just Q&A. At that time, my company was 50 employees.

I stood up and I said, “Jack, look. You talk a lot about passion and all this other stuff. When we were five people starting this company, we were all super passionate. Everybody’s on the same page. Get to 20 people and everybody’s still super passionate. Now at around the 51st person that we’re bringing in, it just doesn’t seem that they have the same passion that we do for the business. How do you instill your passion on somebody else?” In front of a thousand people he basically told me I was an idiot. He says, “You’re looking at it all wrong. You can’t instill your passion on somebody else. You have to hire passion.”

Passion and work ethic. Those are two things you cannot train.

That flipped my hiring persona upside down. I can teach skill, I can teach technique, I can teach product knowledge, I can teach all that stuff to somebody who’s willing to learn, but I can’t teach drive. I can’t teach passion. I can’t teach grit. Sales is a brutal profession. You literally get told “no” 99 times and you have to keep coming back asking for more so you can get that one “yes” in 100. That’s why one of my favorite interview questions is, “What are you passionate about?” I don’t care what you’re passionate about; I care how you describe what you’re passionate about.

For instance, if I asked you that question, you could say, “I really like customers and I really want to do right by them and make sure our product’s a good fit.” Or you could say, “Holy crap. Did you see what happened on Thursday night with the Patriots? They got absolutely smoked. I’m rip roaring pissed off, but I think it’s a good thing, because you know what? They needed to get knocked down a notch here. I still think they’re going 17-1 this year!” I don’t care if football had nothing to do with what you and I were talking about, if you describe it in a passionate way, that means you have some sort of fire in you. My job as a leader is to take that passion and connect it to my business so that you can bring a fraction of that to the table when you come work for me.

The last one is coachability. You need somebody who is coachable. A leader should still be coachable, but if you’re hiring somebody who’s a little bit lower on the totem pole, you need somebody who’s open and willing and wants feedback. You need somebody with a thick skin and who wants feedback so that they can get better.

LB: Thank you, John. You hit on some of the most important intangibles for sales reps. Where can our listeners go out to find more about your work and thinking generally on software sales?

John: My website has almost everything – a resource library that has a ton of free stuff, videos, blogs. I try to focus not just on sales. This is business, and I take a much more structured approach than most to sales in the sense that I focus on the science more than the art. Even engineers tend to resonate with a lot of stuff that I put out there. You can hit me up on any of the social channels like LinkedIn, Twitter, Snapchat and Instagram. I tend to answer whatever questions people have through any of those channels.