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The #1 Mistake Startup Founders Make When it Comes to Sales [Interview with Rex Biberston]

Forster Perelsztejn author on Overloop the sales engagement, cold email, and LinkedIn automation software blog
Forster Perelsztejn Dec 5, 201710 min read

My guest this week is Rex Biberston, founder and startup sales professor at!

One of the most -if not THE most- crucial part of launching a startup is to sell your product. The thing is, lots of founders have no idea how to approach that specific aspect of their job.

That's where Rex comes in!

Could you maybe start by introducing yourself a bit

Sure! I’m Rex Biberston. I have been doing business-to-business sales for a number of years now. I started actually in education sales B2C. While I was an English major in college, I sold educational programs to my fellow classmates. I helped them to get access to graduate entrance exam test preparation courses, and so I learned there that it was really fun to grow a company. We had a $300,000 little program, and we grew it to $800,000 in the first year. After that, I was hooked on sales and business. I was an English major, so it didn’t really make sense. Now I see where all that training came into play throughout my career, so writing, speaking, that sort of thing, it’s been really great to have that background.

Since then, I moved into B2B sales. is probably my most notable company that I worked with; we offered prospecting tools to companies that were using Now they integrated with Microsoft Dynamics, but back then, it was just pretty much a Salesforce shop. I learned how to do cold calling, cold emailing, all the basics of really B2B prospecting back then. From there I went and started my own prospecting company where we did outsourced sales. From there I went into consulting, so that’s where I am today. I love it. I work with startups all the time, and whether they’re tech or they’re professional services, basically, any company that’s trying to scale their sales, that’s where I like to help.

All right, it’s a good summary! I checked out your website a bit, and I like that you define yourself as VP of Sales-As-A-Service. How do you outsource a VP of Sales job?

You know what? There’s usually this gap. When you’re a startup founder, you have to sell your own product or service for a while. I mean, the founder of Yesware recommends that you sell up until you get a million dollars ARR, which is a great idea. I don’t think most people do that. They usually hire a sales rep too soon, or they hire a VP of Sales too soon. I bridge the gap between the solo founder or the co-founder team and actually needing to hire head of sales. I’m that guy right in the middle that helps you transition from where you’re selling it yourself to where you’ve got a scalable process.

You don’t really think about it like outsourcing because that doesn’t really work that well, if you were just expecting somebody to come in and do it for you. It’s really being part of that team but only temporarily. You’re coming in to get the processes built, to scale the messaging to make sure that everything works well so that it resonates with your target market, and then someone else can really come in. Usually, I’ll help someone hire new sales reps. I’ll help put a management style in place. Okay. They’re going to have regular weekly calls, or they’re going to have regular this or that depending on whether they’re remote or in-house – or on-site I mean. It’s not traditional outsourcing like, all right, well, we need this thing to sell, so let’s hand it off to that guy. It’s definitely more like a part of the team for a temporary point in time.

You work with startups. What’s the most common challenge and the most common mistake that startup founders make when they start and it comes to sales?

Oh, hiring sales people way too early, having nothing for them to do, really, and just expecting that – I call it the MacGyver sales rep. I’m not sure if you’re familiar with the TV show MacGyverHe was a guy who could build an airplane out of spare parts in a garage. I mean, they expect that out of a sales rep, and they only want to pay him 12 bucks an hour. It’s that idea that somebody can come and do this. If they know how to sell things, they should know how to build a process. They should know how to really nail our messaging. They should know how to buy the right tools. It’s underpaying the wrong person at the wrong time who eventually could’ve been a great sales rep for the company.

What’s the one piece of advice you would give startup founders who need sales to be up and running ASAP? They have their product, the market fits, and they need to go at it. What’s the first thing you would tell them to do?

If they’re someone who’s comfortable selling it themselves at any level, I would definitely recommend that they work with a tool called ConnectAndSell where they literally just get dropped into sales conversations with their target market all the time. They don’t have to do the tedious work of calling. They just get on the phone with target buyers all the time, so they’re able to have more of those conversations more quickly. It gets them to market really quickly, and then it gets them to understand what the market’s actually saying about their product so that then they can say, okay, well, we learned what works. Now, let’s hire somebody. It’s doing it quickly using the right tools. If you use another tool, if you try and go email only, well, you’re not getting enough responses. You’re not getting enough live people actually talking to you about, so I recommend that they use something like that. They can hear the words of their actual prospects over a live conversation.

Talking about sales processes: you that say you have a uniquely rapid approach when it comes to building sales processes. How does it work? What’s the frame?

I generally start with what I call The 10-Point Sales Success Checklist. It’s like if you take your car in for an oil change, and they’ve got all these different checkpoints they’re looking for. Okay. Is your windshield wiper fluid low? How’s your tire pressure, all these different things? There’s the basic fundamentals that most people think they have down. You would be incredibly surprised to see how few of them have all ten out of ten. Most of them got six out of ten, seven out of ten. I’ve seen as many as nine out of ten but never ten out of ten, never fully documented anywhere.

I’m a big process guy. I like to document everything, so you tell me you know what your value proposition is, great. Does everybody in your company use the same verbiage for on your value proposition? Do they truly understand what it is you do for your customers, and can they explain it in the same way that you do (very rare)? Can they do it in ten words so that if they were on a cold call they would introduce themselves? Can they do it in 30 words so if somebody says tell me more? Those are just two of the ten checkpoints, and most people don’t even have that down.

Are these ten checkpoints mostly built around value proposition?

No. No. That’s two of them. One of them is what kind of lists do you currently have? What access do you have to other databases? It’s all kinds of information about the sale and the sales process.

You wrote an article about the importance of bringing undeniable value before trying to have clients sign. How do we implement that on a day-to-day basis, and is that always a well understood concept by startup founders?

One of the challenges is especially with funded founders, all right, where they’ve got some money from somebody who agreed to give them a half a million dollars or something for their Series A, maybe a million dollars. They think that that means product/market fit. They think that means, well, obviously, I’m providing value because somebody saw enough value. Somebody saw an opportunity, and that’s a big, big difference. VC funds, angel investors, those people are built to capitalize on opportunity, and they know that most of their opportunities are going to fail. That’s a very different thing from a buyer who if they purchase the wrong thing they’re going to get fired. It could definitely damage their reputation. They’re not expected to fail. They’re expected to succeed, so it’s very different.

How do you make sure that you’re providing absolute value? I’d say, if you’re an early founder, like you’re talking about very early startups, you’ve got to make sure that you take such incredible care of your clients, those first clients, that you truly understand what are the problems you were solving for them. If you weren’t solving them as well as you could, build the product around that. You have to make sure that you’re solving their problem. Not just building cool features. Not just using terms like AI or whatever other cool catchphrase you think is really going to get a lot of attention in the media. You have to do what’s best for the customer.

I read that you consider that hiring salespeople based on experience was a mistake. Can you elaborate on that?

Rex: Yeah. It can be, and it can’t be, right? It depends on what you’re trying to get them to sell. Since I work mostly with startups, experienced sales people are rarely – well, I can’t say rarely… I’d say a lot of experienced sales people expect a typical sales process, typical sales training and support, so a startup is not a great place for that. A startup is the Wild West. You have to make things up as you go along. You have to test things constantly, and so someone who’s got a lot of experience is not generally open to that kind of opportunity.

If the price is right, maybe they will be, but again, most startups can’t afford that. In general, if you’re hiring somebody just based on the number of years they’ve done a job, what on earth does that number have to do with how well they’ve done it? Would you like to have a B player who’s been around ten years or an A player who’s been around a year? You know what I mean?

Yeah, of course, makes sense. What are looking for in a good sales hire for a startup? What’s the checklist? What should that person have?

Yeah. Good question. A lot of the times, it’s just general intelligence. Are they pretty smart people? Number two is are they driven? Do they really actually want to make money, do a good job? Do they have personal goals behind that drive that are going to keep them going when it’s really tough, when there’s people who aren’t calling them back, when they’re facing rejection constantly? It’s that drive that’s going to keep them going.

Then, are they good at communicating? If they can’t have a good conversation over the phone, I don’t care how great they are at writing an email. They have to eventually talk to the prospect over the phone or even face-to-face depending on the business type but most of the time it’s over the phone, over the internet like this. If they can’t have a good conversation, there’s nothing they can do for you in the long run.

Let’s talk about tools! Startups use tools. I mean, we develop a tool, and we use a lot of those. I saw that you have a pretty strong opinion about teams who rely too much in technology, right?

The idea is if your product is not strong, if you’re really not benefiting your market, you can have the coolest prospecting tools in the world, and you can automate everything to the tee, and who cares? You’re shooting a blunt arrow at a target. It’s not going to hit the target. It’s going to hit it and fall off. You’ve got to worry first about product/market fit, and then worry about the tools that you use around it.

Again, if you have the wrong processes built – great, you’re using email. I was working as the chief revenue officer of a company called BizAssure, and they sell professional services to insurance agency owners. Those guys suck at opening their emails. Great, I’ve got this really cool tool that helps them with email prospecting. I can get all the emails I want. I’ve got my whole list and my total addressable market and my email list, fantastic. Nobody’s opening my emails, so these tools that we rely on so heavily can become totally worthless.

All right, on the other hand, if you have a good sales process, what’s your sales stack, and what tools do you use or recommend?

It’s interesting. It really depends on the market. I think that’s a critical thing to know is that you have to go through the channels that your target buyer likes to go through. Now, most people are going to argue that nobody likes to be cold called. Okay. I totally understand, but you have to understand too that the pain of getting somebody to call you out of the blue is not going to be as strong as the pain you’re solving if you have a great product.

Generally, my sales stack involves – I don’t use Salesforce. I know that that’s the big 500 pound gorilla in the room. I just hate it. It’s too big. It’s too clunky. I use something like I use HubSpot CRM all the time. Those are my two go-tos for startups because they’re very simple to set up. They’ve got some really great integrated tools, but if I had to for a larger organization, probably Salesforce.

For example, HubSpot has built-in email cadence tool as well as a calling tool. I generally stick with that unless we’re in a situation where we’ve got a large total addressable market. We know who that market is, and we have a large list. Then we can use something like ConnectAndSell where we can have 50 conversations a day with our target market. Beyond that, there’s a few tools here and there depending on the process., they have integrated email and calling and text messaging even, but they didn’t have any really good drip sequences or any way to manage a cadence of events, so I would use on top of them. I try and keep the stack pretty light at first, so we can test messaging, test product/market fit before we really dive deep and build a whole stack on top of it.

You’ve already given awesome advice, but what is the best piece of advice you ever received?

Best piece of advice I ever received? It’s better to be kind than to be right.

Things seems to be moving pretty fast for you. Do you have anything coming up we should be on the lookout for?

Yeah. Actually, I do. My friend Ryan Reisert and I just – well, we’re about to publish a book that for right now we have a working title. It’s going to called Outbound Sales, No Fluff. It’s literally just the process of building a modern sales process. If you’re learning how to sell to prospects who didn’t come to you, from the ground up we teach you how to do that in the book. It’s very, very strong in terms of actionable advice instead of just fluff and stories. Yeah. Outbound Sales, No Fluff, that book should be out soon. I’ve bragged about it on LinkedIn the last day or so. Yeah. We’re going to put it up on Kindle, and then we’re going to do an actual physical copy so people can hold it in their hands.

All right, can’t wait to see that!

Very cool,  thanks!