Founders: YOU are the First VP of Sales


Today, on the Early-Stage Founder Show, I’m talking with Jim Brown, the host of the SalesTuners Podcast where Jim talks with world-class sales performers to help listeners close more deals and make more money.

For many founders, sales skills don’t come naturally, but Jim argues despite any objection a founder can make, they need the be the first VP of Sales for their company. And no, you can’t just bring in a sales person to handle this for you.

Luckily, Jim also lays out a process you can follow to develop sales skills and demystifies what it actually means to sell.

If getting on the phone and trying to convince somebody to buy your software is your idea of a personal hell, then this is the episode for you because you’ll find out why when you sell the right way, selling doesn’t have to be so bad.

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Topics covered:

  • Background leading up to today
    • What is SalesTuners and how did you get started?
    • What does your business look like today?
  • Entrepreneurs are the VP of Sales
    • Why do founders need to sell?
      • Why can’t they just hire a “sales guy” to sell their product?
    • Can these skills be learned?
  • Developing a sales process for early-stage founders flywheel
    • What is the first step of building out a sales process?
      • Can you walk me through the other steps?
    • What do most founders think will be the hardest part of this?
      • What actually is?
    • At what point is it time to build a sales team?
  • Parting advice for founders
    • What advice do you wish somebody gave you when you started your first company?
  • Where can listeners go to learn more?

Related Episodes:

Resources mentioned:

Where to learn more:

If you do want to follow me on Twitter (where he says he spends too much time), you can find him @Jim_Brown.

But for listeners who are looking for a step-by-step plan to build out their sales process, you’ll love what Jim put together. If you head over to, you’ll find a roadmap workbook which you can use to break down the exact daily activities you need to do to reach your sales goals.


Andy Baldacci:    Jim, thanks for coming on the show.

Jim Brown:    Andy, glad to be here, really appreciate the opportunity.

Andy Baldacci:    Just to kick things off, what exactly is SalesTuners? And how did you get started with that?

Jim Brown:    Yeah. SalesTuners is a sales training, coaching, and consulting firm, and the reason why I got started is I’ve had a couple of successes in my career. I was the top sales account executive for a company that the 58th fastest growing private company in the country. I was then recruited to another company to run their sales team. Well, to build and then run their sales team, and I was very fortunate. We were able to sell that business to Oracle. So I had a couple of great successes. Then I got this really big head and ego that said, “You know what? You should go raise money. You’d be good at this.” So I did.

I raised over a million dollars in venture capital in less than two months on nothing more than a PowerPoint deck. So again, but all it did was feed my ego. I then ran that company into the ground over the next two years, so 100% failure, complete bankruptcy for the company, and so, I’ve seen both sides of the equation here, of both success and failure when it comes to tech start-ups and SaaS.

And so, as I was kind of picking up the pieces, and figuring out what I was going to do next, Andy, I started talking to pretty much any tech founder that would have a conversation with me, and I kept hearing the same thing over, and over, and over, and over. And that was simply, “Jim, we need to hire a VP of sales, who’s just going to come in, and absolutely kill this for us.” And I was that type of person. I could do that for somebody, but I said, “Guys, you’re missing the point here. You can get that, but in order to do it, you’re going to pay me a lot of money, or cut off a really big chunk of equity, because, especially in the early-stage, revenue and sales is all you have, right? So if I’m the one driving that, I’m gonna get a big piece of it.” And they’re like, “No, no, no, Jim, you don’t understand. We’re going to raise money, and then that’s going to allow us to hire VP of sales.”

And I just kind of looked at him cross-eyed, I’m like, “No, you’re not,” right? Unless you have some kind of flywheel going on here that you can prove that you can sell this yourself, no VC is going to give you money on this. And so after hearing it enough, I knew that these tech founders, who really didn’t have sales backgrounds, they just needed some kind of basic level set to what that was. And so, I created SalesTuners, and been doing it for over a year now, and having a lot of fun.

Andy Baldacci:    And so, what does a business look like today? What sort of work are you doing with founders?

Jim Brown:    So I typically, at this point now, am working with companies who have between two and 10 sales reps. So they’ve gotten just past the founder stage, but again, that’s just my target audience. I still do have a lot of founders that I work with and call on. One of the things I was talking with you about is, I was just with an accelerator, and venture capital company today, and they expressed to me, everything that I just said is still true for their companies. And so, when they call, they’re saying, “Okay, how do we sell this? What’s the process of going through this?” And we’ll start talking about that. And then they might start to say, “Okay, how do I actually put together the right profile of person to go hire to fill that once I have created that flyaway you’re talking about, right?”

And then the last part of it from a coaching aspect is, I actually work one-on-one with the … whether it be the founder, or a sales rep to say, “Okay, right before you go into a call, how are we going to set up the conversation? What are the things that we’re going to say? What do we expect the prospect to say? What is our goal to get to at the end?” And then, they’ll also call me right back after call is over, and say, “Okay. Here’s what happened. The prospect went here. I think I should’ve gone there. What did you see? What do you think we should do differently.” So, again, I know it’s wide-range, but we do quite a lot of different stuff in the sales arena.

Andy Baldacci:    That’s interesting. And we’ll dive into a lot of that a little bit, especially on how early stage start-ups can start building out that first flywheel. But just to back up a little bit, it’s something that I think I take for granted, because like I was telling you before, I sort of geek out on sales myself, even though I am not a salesman at all. But for listeners who might be on the other side of things, where they don’t want to do sales, why is it so important for founders to learn to sell?

Jim Brown:    Well, I mean, without sales you have no company, right? And so, I can’t stress that enough. A lot of people, a lot of founders, specifically, of tech companies, they believe, if we just build a great product, and if we just show everybody our products, and features, and benefits, they’re just going to buy, and that’s just not the case, right? I mean, I’ve worked for some amazing companies with some amazing products and services, and unless someone goes out there, and actually has a conversation, and sell something to someone, there’s no revenues. And especially, if you don’t have any venture capital, there’s literally no money to run the operation. So sales is the life blood of an organization. I used to have a mentor tell me, Andy, “That nothing happens in business, until someone sells something to someone else.”

Andy Baldacci:    Yeah. It’s very simple, but it couldn’t be more true, and it’s something where it … I’m not going to say that there’s some point in time, where you really could just build something and organically takeoff, but especially now, with how competitive things are really in the SaaS market, when you have dozens of competitors for nearly any niche, it’s even more true, that you can’t just expect a good product to sell itself. But if someone’s saying, “Okay. Yeah. Sales are important, but why does it have to be me? Why can’t I just hire that sales guy, or sales gal to sell my product for me?”

Jim Brown:    Yeah. I mean, first off, no one’s going to tell the founder story better than the founder, right? And so, when you are truly starting a company, there’s a reason why you started the company. You have a big vision. You have a big idea of what should be different in the world. And that energy, and that motivation, and that vision is what you have to share with potential prospects to get them excited about it, especially, if you’re doing something truly unique, and truly cutting edge. And no one’s ever going to be able to tell that story better than you. Now, once you get your first couple of customers, and get real customer feedback, and whatnot. Now, you can start to consider bringing on a salesperson, whether it be VP of sales, or just a sales rep. But you cannot transfer your enthusiasm into them.

They have to figure it out on their own, and all that is, is having them understand what the buyer’s true pain point is, or gain what they want to gain, and being able to talk through that, not just come in and throw up all over them what your product does.

Andy Baldacci:    And this is something that, again, we’ll get into some of the details in a little bit, but just having so many of these conversations myself with founders, who seem to do anything they can to avoid getting on the phone, having some of these conversations, and a lot of times what I’ll hear is that, “Well, I’m just not an extroverted person. I’m not a natural social butterfly. I’m not someone who can easily do sales. It doesn’t come to me, so what do you say to that attitude? ‘Cause I’m sure you’ve run into that yourself.

Jim Brown:    Oh. For sure. Yeah. In all honestly, as much as it may sound like I’m an extroverted person, yeah, I’ve been pretty good in sales, but I’m not. I get my energy by being alone, and that’s how I recharge, so I’m very much an introverted person. What I believe, Andy, is this next generation of great salespeople. They’re going to be subject-matter experts, right? They’re going to be subject-matter experts, who’ve been taught how to sell, as opposed to people who are naturally quote, unquote gifted salespeople, which I don’t believe by the way, who are taught products. I strongly believe that. I’ll give you a quick anecdote. So my wife does sales force implementation, so sales force proper, they sell the software, and they hand it over to an implementation partner. She’s the one who actually goes in and does the work. She doesn’t sell it, but she does the work.

And all of these salespeople are bringing her in on deals, because they know when they bring Kathy Brown in, the deals gonna get done, and it’s going to be huge, because she actually has the empathy of the buyer. She understands, because she’s the one who has to deliver it. So she knows the real questions to ask. She knows the real pains that they’re actually having. She knows the real solutions they want to achieve, and when she’s able to have that fluid conversation, they just start eating out of her hand like, “Yeah, we want this. You’re amazing. When can we start?” As opposed to just a salesperson trying to get a contract signed. And for the tech founders out there listening to this, you are the best person to sell your product in the beginning.

Andy Baldacci:    ‘Cause you already have that. You already are there. You’re the one, like you said, with the vision, that understands a problem, you understand the pains, and that’s ultimately, what a lot of sales comes down to.

Jim Brown:    100% that’s what sales is. It’s truly DISCovering the pain, or gain that your prospect has, and then using your solution to fulfill that need, and transferring your enthusiasm to them to get the deal done.

Andy Baldacci:    Alright. I’m gonna put myself in the devil’s advocate again of that hesitant founder, and I don’t many of my listeners are fully on this side of things, but I do know a lot of people have still doubts about things. What if someone says, “Well, why don’t I just do some marketing? Why don’t I just write a bunch of blog posts, and really go all in on content marketing. Isn’t that enough?”

Jim Brown:    I mean, listen, there are so many ways to accomplish the things that you have, and if you have all the time in the world, if you’re a great writer, if you have a big budget to do all that marketing, and advertising, and anything along those lines, that’s one way to do it. And so, now … but here’s the thing, all those are going to do is generate leads, right? So someone still has to talk to those leads, unless you’re Atlassian, or Slack, or something along those lines, where truly, they got luck, and they built something amazing, but they got lucky. That’s not going to be you.

You’re still going to have to talk to a customer, and so, like I said, I mean, I talked about a couple successes that I had, and I talked about the failure that I had, and I’ll be very clear. The failure that I had as a founder was because I didn’t talk to enough customers. I didn’t do enough true DISCovery, and understand the real pain, and get into the empathy of my buyers. And so, as a founder, you can choose to do all those, but customer development has got to be one of the core drivers of your business.

Andy Baldacci:    Yeah. Absolutely. And it’s something where … obviously, we’re going to be talking about sales, specifically. But I think you hit it on the head right there. We talk about customer development, because if you want to focus on content marketing, or some more hands-off lead generation channels, you still have to talk to your customers, who understand what they really care about, and I think that is where I get a lot of hang up from founders is that, they just ultimately are nervous about getting on the phone, and talking to customers, or potential customers, especially.

But no matter what path, or what channel you’re going after, you need to kind of lay that foundation with strong customer development, or you’re not going to get the results your business really needs to survive.

Jim Brown:    Yeah. Let me give you a practical example here. So one of the companies I was talking about that we sold to Oracle was called Compendium. So Compendium was started by Chris Baggott, who was one of the co-founders of Exact Target. So Chris left ExactTarget, I think six years in. He had taken some chips off the table, and was starting a new company. He thought that he could just take the playbook from ExactTarget, and just run it, and it was going to be great. Unfortunately, that wasn’t the case.

So what Compendium was in the very early days was essentially … it was a blogging platform, right? It did some compending type things to kind of trick the Google algorithm, but at the end of the day, it was a blogging platform, therefore it was competing against WordPress, which as you know is free. Very hard to compete against free. And so, when I came in, I said, “Heres the first thing that I want to do. I’m going to go out, and I’m going to interview some potential customers, and just understand what their pains are around content.” And so I did, and fortunately, I have sold to some big companies in the past.

So I called on some really big companies. I said, “Hey, I want to bring in my VIP of product, and I just want to have a conversation. I’m not here to try to sell you anything, because frankly, I think what we have is something you’re not going to be interested in buying.” They’re like, “Okay, we’ll be willing to take this conversation.” So we have about a 30, 45 minute conversation, and I’m just truly uncovering the issues they have surrounding content, and as I did this, my VP of product was like taking furious notes to truly understand what needed to be done. And I kid you not, Andy, we took all this information from probably about 10 different prospects.

And we came back, and we brainstormed, its like, “Okay, here’s the themes and patterns of what we heard them say.” And James, my VP of product, he literally built me clickable prototypes that I could then go take and put in front of the customers. And I’m talking … these were like PDFs that if I clicked in the wrong spot, it would break the whole thing, right? But I said, “Guys, here’s what I heard you say you wanted,” and I would walk them through it. “Is this is? If this solves the pain, would you buy this?” They’re like, “Yes. This is amazing. This is exactly what we needed.” I said, “Okay. I mean, this is $60,000. I didn’t know that, that was the kind of budget you had.”

“If you can solve our problem, we’ll absolutely spend that.” And so, I said, “Help me better understand. What exactly was it that you were wanting,” and what I was getting at, ’cause again, these are clickable prototypes. I wanted to understand what they were buying as their first main priority. “Okay, great, so here’s the thing. Let’s do a deal. We’re going to sign the contract. Obviously, this is going to take 30 days to implement you on. So I’m gonna connect you with a client success manager, and he’s going to walk you through setup, and within 30 days you’ll be able to use this. But he’s going to get everything mapped, and matched, and all those kinds of stuff for you.” And reality was we have 30 days to go build the product, right?

We had 30 days to build exactly what it was they bought. But we did that enough times that eventually we had the feature set that we needed, and again, all I was doing is going, and talking about the specific pains that I had seen similar customers need, or want to have improved, and sell to those pains. That’s all I was doing.

Andy Baldacci:    And so, I want to dig into that a bit more, and talk about what it actually looks like to build out the sale process, and especially, for those early stage founders, who say that they have [inaudible 00:13:23] in customer development, and they already do have a hand full of customers, but probably most of those have come through word of mouth, through more hands-off approaches. So for an early stage founder, who is willing to put in the time, to really build out the sales process, because they see the value of that. What is the first step?

Jim Brown:    Well, let me tell you what the first step should not be first. Okay? So heres what I see too often times with start-up founders. They kind of have a three step process, one is generate interest. In some capacity generate interest, like you said, that could come from a referral, maybe it is a cold outreach, maybe it’s inbound lead [inaudible 00:13:57]. So it’s generate interest. The second one is throw up all the information you have on the buyer about your features and benefits. And the last one is, hope they buy. So that doesn’t work, right? And it’s not going to ever work for you. So the first thing you have to do is get yourself out of that mindset.

After that, what I want to look at is we’re going to have to prospect in some capacity, right? So whatever prospecting looks like for you, you have to do that. The first thing that we’re going to do, and I’m going to get kind of technical here. So the first thing we’re going to do is have to build a relationship, okay? And I do not mean make friends with a prospect, okay? I don’t need anymore beer drinking buddies. I’ve got to force them every Friday to play golf, I don’t need that, right? But what I do want to know is I want to understand how to convey information to you in a way that’s going to allow you to trust me, so that you will end up buying from me. And we could go as deep as you want at that.

I’m talking about like DISC profiles, I’m talking about primary sensory dominance. There’s a lot of things in there that are truly important, that when you understand how that buyer needs to receive information, I don’t want to say you can control them, but you can kind of lead them where you want them to go when you start to truly understand that.

Andy Baldacci:    Yeah. So what does that process look like of truly understanding the buyer? Where do you begin on kind of getting into their mindset.

Jim Brown:    So I’ll start with DISC, right? Are you familiar with the DISC profile?

Andy Baldacci:    Yeah. [Casey Cobb 00:15:20], who is advisor to a lot start-ups out of San Francisco. She turned me onto it about almost a year ago probably on this podcast, but please dive into that for listeners who aren’t as familiar.

Jim Brown:    Sure. So I’m a big fan of it. There’s essentially four types of people. There’s the D, which is dominant, and I, which is an influencer, and S, is what’s called a steady relater, and a C, is just compliant, right? So I am a D. I’m a driven, aggressive, hard charging, goal-oriented, whatever. So my natural style is to take no prisoners, and just go run over everybody, right? So I need to know what my profile is, but more importantly, I need to try to figure out what my buyer’s profile is. So if I’m a D, and I’m selling to another D, I got to be a bigger D than they are. I kind of got to punch them in the nose a little bit to get them to pay attention to me.

But if I’m selling to an I, I better ask them how their weekends going. And I better talk about how fun it’s going to be to use our product. If I’m talking to an S, an S doesn’t want to change anything, ever. So I have to be able to get them comfortable with the idea of change, that actually it becomes their idea instead of mine. And a C, a compliant person, they’re just going to do whatever you tell them to do, and they’re going to want so much data. These are the types of people be like, “Hey, Andy, can you get me a datasheet on this, and help me understand A, B, and C?” You bring them that datasheet, they’re like, “This is amazing. Can you get me data on where you got this data?”

It’s crazy, but I want to know what my buyer’s profile is again, so that I can match their tone, not mine, right? So then I move over to what I call primary sensory dominant, so really there are three ways people learn, visual, auditory, and kinesthetic. So they sound just exactly like they are. So a visual person learns by seeing. They talk about the big picture. They talk about all kinds of different things there. An auditory, they have to hear what you’re saying, and so an auditory, they may actually slow you down, while you’re talking. They may repeat what you’re saying back to you. That’s just how they process the world, and so, you have to be able to give them that space.

A kinesthetic has to feel, and touch, and be a part of what you’re doing. So when you start doing a demo with a kinesthetic, you need to give them the mouse. You need to let them drive, because they have to do that in order for them to learn. So these are just a couple of things that we can look at there, but again, I want to figure out their tone. I want to figure out how they need to receive this, so that I can match my style to theirs.

Andy Baldacci:    And, obviously, those are things that we can go super deep on, they’ll take up dozens of episodes to really flash it off. But are there any resources, or things that you could point listeners to, to help give them a better idea of how they can kind of suss out the kind of personality that their prospect has.

Jim Brown:    Yeah. I could totally send you a couple of links that maybe you can include in the show notes, for sure.

Andy Baldacci:    Awesome. I’ll circle back to you about that afterwards, and get that linked up in the show notes. And one thing I wanted to kind of go a little off topic with, is that if say you don’t see the product that you’re making right now as being a purely enterprise driven sales thing. It’s maybe the lifetime value of a customer is in the thousands, but not the tens of thousands. In my mind, this is something that you could kind of generalize. Like you would do a lot of customer development interviews. You would try to figure out, okay, I have these different personas and this is roughly what their personality is. So this is how it can kinda create more marketing materials to address that. Is that off base, or is that a reasonable approach of how you could kind of apply this in a lower touch, more marketing way?

Jim Brown:    So I totally agree with you. You still need to do the customer development, and here’s what you need, here’s the critical part of that. You need to have what I called tactical empathy, right? Tactical empathy simply means you truly understand why the customer is saying the things that they’re saying. Until you get to their why, all the marketing collateral that you’re going to create is just for you. It’s not for them. So if you can truly understand that tactical empathy, how to be relevant to them, the reason why they need it, as opposed to just because here’s what our product does. That’s when you’re going to have true success, even at that lower lifetime value.

Andy Baldacci:    I see. Okay. Getting to that why, it’s something where it seems … when you’re talking about it in theory, when you’re writing blog posts, or reading blog post, or whatever. It seems like a straightforward thing to do, but it’s kind of hard to actually get that out when you’re doing this customer development.

Jim Brown:    It is really hard.

Andy Baldacci:    Do you have any tips on the best way to do that? Because usually when you ask a prospect, “What’s going on in their business? What are they trying to solve?” That sort of thing. You’re going to get more superficial answers. There’s something that isn’t actually the core of the issue. How do you get them to go deeper into that?

Jim Brown:    It’s all through questions man. So you have to be willing to have the patience, right? To actually take them down that path. I call it the three Ps, right? So first off, you have to have permission to put them in pain, because you’re going to have to ask a lot of questions, so make sure you have permission. The second is, you have to have a process, right? I will let you lead me somewhere, if I actually know that you know where you’re going. So show me the process of how you’re going to get me there, and then you got to have patience, ’cause again, you are putting someone through a painful situation, essentially. And so, to uncover the root cause of their issues, it might take a little bit of time, right? And you got to get below the surface, right?

If you and I were in front of each other right now, I’d show you a whiteboard, I would start drawing what I call the pain iceberg, but essentially, most people, especially non-salespeople, they will try to sell the top of the iceberg, the tip of the iceberg, which is only 10, 11% above the water. So a prospect comes in, and they tell you the first pain that they have, and all that is, is an indicator of the real pain. But most salespeople, and especially, like I said, most tech founders, they’ll be like, “Oh my gosh, that’s it. I’m going to solve for that problem.” When, if you just ask them to say, “Hey, tell me more about that.” All of a sudden, you’re going to start to dip them a little bit below the water, right?

Andy Baldacci:    Can you give an example of what kind of a tip of the iceberg problem may be?

Jim Brown:    So let’s do this real quick. You mind doing a real quick role play?

Andy Baldacci:    Sure.

Jim Brown:    Alright. So this is not a stage, I don’t know what you’re going to say to me, right, at all? So you tell me about a product that you sell, or that you buy, or something on the lines. You just give me a pain indicator, I don’t care what it is, give me a pain indicator of something that you either buy or sell yourself personally.

Andy Baldacci:    So I guess, right now I’m working with Groove, which they make help desk offer for small business, and one of the big things we’ll look at is just when people … when they say they’ve outgrown email, when their inbox is a mess, that sort of thing. When they lost track of what’s going on when customers are writing in.

Jim Brown:    Okay. So I just want to restate what your pain indicator is. So you said that small business help desk software, they start to lose track of all the emails that are coming in, and they’ve outgrown their previous thing, correct?

Andy Baldacci:    Mm-hmm (affirmative)

Jim Brown:    So Andy, gosh, I heard you. Tell me more about that. What do you mean?

Andy Baldacci:    Well, so with this, it’s a lot of times, you’ll have people who … when they’re just starting out, they’re using Gmail, they’re using whatever email platform they’re using for customers. They don’t actually have a tool, and when they just have a few customer emails a week, it’s not that big of a deal, but as they grow, and especially, when they bring in another person to help with support, they’re going to have duplicates of efforts. So they’re sometimes going to respond to the same customer twice, sometimes customers don’t get responses at all, and ultimately, it leads to bad customer support, and typically, bad customer support doesn’t help you keep customers in the long run.

Jim Brown:    Okay. So now, get out of the role of Groove, and get into the role of the customer that’s saying that. But everything you just said there is something the customer would say, okay? So let’s just continue. Wow. I can definitely see how that’s the case, Andy. How long has something like this been a problem for you?

Andy Baldacci:    We’ve probably been dealing with this for about a year or two, but it’s never been bad enough to actually change. We’ve looked at other solutions, but we always just stick with email.

Jim Brown:    Sure, ’cause it’s probably just the easiest thing to do at this point. So what are some of the other things that you’ve done to try to fix this problem?

Andy Baldacci:    So we’ve worked with trying to get better training with the customer support people to see if there are things that we can do to just kind of prevent some of these fires from coming off to begin with. We’ve looked into other support options, but a lot of the software just seems super complicated.

Jim Brown:    Gotcha. So I mean, did it work?

Andy Baldacci:    No. Not really.

Jim Brown:    Okay. What has this cost you, Andy?

Andy Baldacci:    It’s hard to say. Yeah. It’s really hard to try to put a number on that.

Jim Brown:    Okay. Tell me … I mean, I don’t even know. What happens if you don’t fix this?

Andy Baldacci:    Yeah. If we don’t fix it, I mean, we have a lot of burnout on the support team, just because customers aren’t happy, and it’s not easy to handle that, and it’s not easy to just do their jobs. So I think we could see some turnover on the team, but also the bigger issue is just customers aren’t sticking around.

Jim Brown:    Okay. Okay. Now, this might sound like a crazy question. I apologize if it offends you, but are you okay with that?

Andy Baldacci:    No.

Jim Brown:    Okay. Andy, how are you hoping I could help? Right?

Andy Baldacci:    I mean, I’m hoping … Yeah. Okay.

Jim Brown:    But you see where … I took you down, and to be clear, I don’t sell Groove, I have no idea of what it is that you do, how you do it, how you sell it, right? But you gave me a pain indicator, I asked you a series of questions, and I took you … it didn’t matter what you were selling, right? Or it didn’t matter what I was … I just took you right through that, and so, now I’m able to develop … and as long I have that tactical empathy, I’m truly listening, and I’m understanding. I can take you wherever I want you to go with that. The way I ask the questions are also very important. Again, the tone, I want to match your tone. I don’t want to be an aggressive bully like my DISC profile says I should be.

Andy Baldacci:    That’s interesting. And so, where would you follow-up with that? Do you go into a pitch? How do you know where to go from there?

Jim Brown:    Yeah. So when I ask that question, the end how are you hoping I could help, right? Couple of different things you could have said, you could have said, the best answer you could possibly give me is, “Jim, I don’t know. That’s why I was hoping you could tell me, right?” And so at that point, I could do whatever I want, and I will go deeper right? But you could have also said, “Gosh, I was hoping you could do X, Y, and Z for me.” Which is also good, because I’m not going to go there. I’m still going to tell you the exact same thing, but I’m going to say something on the lines of, “Well, Andy, let me tell you. I don’t know that we can help you. What I can do is tell you is how we’ve helped other people who’ve had similar situations to you.” Okay? Because if all of a sudden I do a pitch, and I tell you that I know that I can fix your problem, and here’s exactly how I’m going to do it.

As a buyer, the first thing you would want to do is tell me that I’m wrong. Right? And so I’m just not going to give you that chance. I’ll be like, “Hey, here’s what I’ve done for other people that are similar to you,” ’cause now if you say, “Well, that won’t work for me.” That’s great. “Hey, no reason, I didn’t think it would, I was just letting you know that’s what I’ve done for someone else,” right? Something that could work for you might be something completely different, right? So I can take that to wherever I want to go. So whatever the pitch is that I want to give them, I tell it to them as a third party story. I tell them how I’ve done it for other people.

Andy Baldacci:    It seems like that sort of disarms them, and it makes so … you’re right, you don’t give them the opportunity to say, “Oh, no, no, that’s not what we need.” Okay. That’s interesting. And how … ’cause I know a lot of the companies you work are probably selling different levels of engagement. So they’re having different price tiers. Some are going to be on the enterprise level, where it’s six figure deals. Some are going to be in the smaller side. How do you adjust the role of a sales team, a salesperson, just the sales process based on the deal size?

Jim Brown:    To me, that really is just about the length or duration of the sales cycle, right? So if I’m under five grand really, you’ve got maybe two calls with me. After that I have to either disqualify you, or just tell you it’s not going to be a fit, because I don’t the time … Well, not the time, I don’t have the money to continue investing with you on the phone. It’s just not worth it to me at that point. But I’ve had sales cycles as long as nine to 12 months, right? In some of the stuff that I work on. The average deal cycle that I work on is typically somewhere 45 and 90 days. And so, it’s really just duration as opposed to the price.

Andy Baldacci:    That makes sense. And obviously, it’s going to be some factor of price to duration of … and to figure out the … I guess, value of the time, and all of that. So for a typical SaaS company, a lot of the B-to-B companies that I talk to, they’re monthly price is probably going to be average around $100 a month or at least that’s what they’re shooting for in hoping that the customers are going to be at. And so, lifetime value will probably be 3000ish, for higher-end clients, it will be a bit higher. Is that something where it’s like want to be hands-off primarily, and then during the trial, or during a demo, that’s where you can do some of this? Or how would you even approach that when those values aren’t above $5000?

Jim Brown:    So I would say the only difference in what we’re talking about right now is if we’re truly early stage, right? This early stage customer development is huge. The amount of time that I’m spending with the customer at that point, it’s kind of an investment in my own product. I want to hear on the frontline what the problems are that you have, because you could be giving me new ideas for additional features, right? You could be giving me … I want to hear the words that you say, so the next time that I talk to someone like you, I’d be like, “Hey, gosh, my product has this, but I’ve heard some customers are using it this way, because they had this problem. I can’t imagine that’s the case with you.” “No, that’s exactly what I’m having a problem with,” right?

So I want to use my customers words back to them, and it’s really, really valuable. So even at that price point, I would still be spending a lot of time on the phone, if I’m truly in the early stage.

Andy Baldacci:    Yeah. And that actually makes a ton of sense. It’s doing the things that don’t necessarily scale, or don’t scale in the way you’re doing them right now. It’s because you’re not looking to necessarily get that immediate ROI on every sale you make in the early days. You’re trying to learn as much as you can to improve the product, so you can build out the process that does scale.

Jim Brown:    That’s right. Paul Graham wrote an excellent article on that about doing things that don’t scale, but one of the things, Andy, that I’ve had a few of my customers do that have call reluctance, right? They just don’t want to get on the phone, and have a cold call. What I’m talking about truly is just the idea of interviewing people. And so, I’ve had them say, “Hey, change your names.” So instead of Andy, you’re going to be Bill, and instead of talking about Groove, you’re going to say, “Hey, I’m with ABC Company,” and whatever it is, you’re going to call on your target audience, and say, “Hey, this is Bill with the ABC Company. I’m actually a freelance journalist, and I’m writing articles about people who have challenges with their help desk. Could I actually interview you for a 20 minutes for an article that I’m doing? And if I publish it, I’ll send you the results.”

Most people are going to be like, “Yeah, I’d love to be published in an article,” right? So you basically go in and have an interview with them, and you ask all the same questions you would ask in a sales process, and you get all this amazing information from them that you could truly use for an article, and write the article, right? Or you can wait two to three weeks, change your name back to Andy, and now call on them, and say, “Hey, it’s Andy from Groove, I typically work with companies who have X, Y, Z problem. I have no idea if you have any of those problems.” But it’s the exact same problems they gave you, right?

So now you’re able to have a non-cold call if you will, because you know the problems are happening. “Wow, I get so many cold emails, and so many cold calls with people who just have no relevancy to me, but you know exactly what I’m dealing with. Yeah. I’d love to have a conversation with you.”

Andy Baldacci:    And even if you’re not doing it to the same exact person you spoke with before, a lot of those problems are going to be trends. When you do more of these interviews, these customer development calls, your goal is to identify the common problem. So that if you are going to do cold email for prospecting, or whatever it is that you’re doing to first get in front of the prospects, you will stand out, because they’ll say, “Oh, wow. All these cold emails that I get are almost always generic, and have nothing to do with me, but this one seems like you know exactly what I’m going through,” and it’s because you in the work upfront, you kind of do.

Jim Brown:    That’s right. Now, I don’t have to be worried about being eaten by a bear again, do I need to send police to … I hate that crap that’s coming out, but, yeah, no, you actually are relevant to the person who could handle the problem that they have.

Andy Baldacci:    And so, say these early stage founders have done some of this work, and they’ve made it a real part of what they’ve prioritized, and they have gotten some of those customers, and they start to prove out, okay, I know what the pains are, or at least have a very good idea of what the pains, and how we can solve them, and truly provide a solution to this market. Is that when it’s time to start building out a sales team? Or at what point really should they look to offload some of the sales work to someone other than themselves?

Jim Brown:    As soon as you have something that can be truly repeatable. Yes. I believe that’s when it’s time to start the sales process. Now, that doesn’t mean you have to hire a VP of sales. I want to be very clear. Sometimes it might still be … now, you hire an entry level of salesperson, who maybe has a little bit of training potentially, and all they’re doing is setting up appointments for you to close, right? So now all you’re doing is coming in for the close. So there’s a lot of different things there. But yes, once you’ve created something that is repeatable, and you’ve sold it a couple of time at a certain price point, and you solved the same pain problems a couple times, that’s when it’s time to start building out a sales team.

Andy Baldacci:    I mean, that makes perfect sense, and it goes back to one of the other guests I spoke with a few weeks back, Lars Lofgren, he was at KISSMetrics, and now he’s at I’ll Teach You To Be Rich, and one of his things is that, it’s very, very hard to hire people to build out systems for you.

Jim Brown:    100%.

Andy Baldacci:    You can hire people to implement them, and make some tweaks in this and that, but it’s very difficult, and if possible at all, super expensive to actually get someone to come in, and figure it out from scratch. And that really is the founder’s job at least for a couple of the channels in the early days until you can bring in more senior level people, but even then, it’s not an easy task. And especially, for sales, I think you’ve driven the point home. This is something that the founder really needs to own, and I like how you said, those first hires don’t need to be VPs of sales. It can be someone to set the appointments, and that can just help you be more efficient, and that’s what you’re really looking to do in the end of it.

Jim Brown:    Absolutely. I mean, you’re trying to scale something, right? And so, all you need to do is just magnify yourself, and that doesn’t … because again, if you go out and try to truly get a real, like real VP of sales, you’re just going to pay them too much money, and you don’t need that at that point, because you’re still learning.

Andy Baldacci:    And yeah, when you say real, is it someone who didn’t just take a sales class in college, and is a fresh grad, but because you only have three people on your team, you’re going to give them the VP of sales title.

Jim Brown:    That’s right.

Andy Baldacci:    You mean someone who legitimately has earned that title, and that’s … if you were going to hire, that’s kind of what you would need, but it is not really the time to be thinking about that. But, Jim, to sort of tie it all together, I’m curious, looking back on your own experience, and knowing what you do know now, what advice would you wish someone gave you when you started your first company? You already had a lot of the sales knowledge, but what advice do you really wish you had back then?

Jim Brown:    I might go back to that why, right? I didn’t understand the why behind the customer empathy. I truly didn’t. I tactically understood it, and I tactically could use it to my advantage, but once I had the couple of successes that I had, and I started my own company, and raised, like I said a million dollars in venture capital for it, I thought I’m good now. I’m the smartest person in the room. I’m just going to build exactly what they want from the get go, and as soon as we launch, we’re going to have balloons, and confetti, and all that, and everyone’s just going to start using it.

And it couldn’t have been farther from the truth, and if I would’ve just actually built an iterative process in front of my customers, and show them, and heard from them what they truly were experiencing, the outcome would’ve been completely different. I tell you, Andy, one of the things I talk about quite a bit is the difference between context and content. So my last company, I had previously read The Lean Startup, okay?

And I dismissed it. I completely dismissed it. I said, “If this guy was any smart, or any good at his job, he would just build what his customers wanted. And he obviously has no idea what he’s talking about.” And during, literally, the July that I’m month away from closing the doors to my business, and filing for bankruptcy, I reread that book, and I was pouring over the pages, and I was just kicking myself. And the content hadn’t changed at all, but my context was a world away from where I was, and I understood now. So it truly is that why, and it’s hard to get to that why.

Andy Baldacci:    No. I love that. I love the, get to the why, and understand the why, because, ultimately, that is what it’s all about in terms of building a successful business, because without understanding the why, you’re really just depending on luck, and if you look at the success rates of start-ups, or any business really, most start-ups don’t get luck. So don’t rely on that, but before we wrap up, Jim, I like to ask all my guests a few rapid fire questions. So I’ll go through them pretty quickly, but your answers don’t need to be too short. And the first one is just, what do you currently spend too much time doing?

Jim Brown:    Okay. I got these, but this might be one where you have to add a little bit. Let’s see.

Andy Baldacci:    Yeah. No problem. And it doesn’t need to be something specific to sales, or some deep insight. Some people just say, “I spend too much time on my phone,” or just whatever it is.

Jim Brown:    Okay. I’m going to be completely honest, I really do spend too much time on Twitter. I have gotten customers from Twitter, but I know that at the end of the day that’s not where my clientele’s going to come from. And I have kind of just used it as a filler of any kind of downtime whatsoever. And there’s the brain energy that gives that ping of energy when I see something cool come up. But, yeah, definitely spend too much time there.

Andy Baldacci:    And then where do you wish you could spend more time? If there was one area that you could really double down on, what would that be?

Jim Brown:    This may sound crazy, but actually, with my today’s customer, right? So I’m focused so much on growing my business, and I deliver on everything that I sell to my customers, but I wish I could spend some more proactive time with them, going deeper both in the relationship personally, as well as the business engagement that we have. I think there could be a lot more there, if I just had the time, and, or made the time to do that.

Andy Baldacci:    And then for SalesTuners, what are you hoping to accomplish in the next quarter?

Jim Brown:    The next quarter, I’m still building out the podcast myself, so one of the reasons why I started that podcast, is because I’m always trying to master my craft, and get better at it, so I thought why don’t I call on great sales leaders, high performing individual sales reps, and have a conversation with them about the things that have made them better. And so, I’ve been at it a year now on the podcast side, and I’ve met some amazing people, and so, I’m hope to continue to grow that. I’ve really started to edit the show now a lot more, as opposed to just doing a raw format interview that I used to do. So just kind of double down efforts on that.

Andy Baldacci:    Do you do the editing yourself?

Jim Brown:    Not anymore. So I did, because-

Andy Baldacci:    Okay. Good.

Jim Brown:    Yeah. I believe that you have to do things in the beginning, just so that you understand the process, but then once I develop something that could scale, and be repeatable, that’s when I started outsourcing it.

Andy Baldacci:    Perfect. And then the last one is just, what do you see as the biggest obstacle to really getting to success, to getting your podcast where you want it to be?

Jim Brown:    It’s funny. I just got an email before we started our conversation today from Libson, saying, or talking about the podcast analytics, that they were going to do an upgrade on. So it obviously has a lot to do with IOS 11’s release of iTunes, and whatnot. But I’m really, really excited, because that has been the biggest hurdle to growth is truly having real analytics behind a podcast.

Andy Baldacci:    It’s crazy, and for listeners aren’t aware of this, when you live in the start-up world, and you have access to all the amounts of data about anything you can want, you look at podcasts, and it’s like we get numbers of downloads, not even a true listen, or how much they listen, just number of downloads. You can get like some geographic data, but that’s about it. And iTunes has recently said that they’re going to be overhauling that, and so, I’m very excited for that too, because right now, the level of insight is almost nonexistent.

Jim Brown:    I love the way you said that, because basically, it’s like we’re living in the stone age, but let’s just be honest, I mean, we’re still making a living working on the internet, so things are great.

Andy Baldacci:    Oh. For sure. It could be a lot worse. It could be a lot worse. But honestly, Jim, this has been a great chat, and if listeners want to hear more from you, just learn more about how SalesTuners can help them learn to sell, what are the best things for them to do? Where should they go?

Jim Brown:    Yeah. A couple of different ways. One is if you do want to follow me on Twitter, where I spend too much time, you can get me there. I’m @Jim_Brown, and I talk a lot about the stuff that I do, and I also engage in a lot of conversations there. But also, one of the things that I did for your listeners, Andy, is I’ve got a roadmap workbook that they could go to, and it’s at salestuners/roadmap, and I’ll be very clear, I want to emphasize that word work. But here’s the thing that I see a lot of both founders, and salespeople deal with, they’ll setup a goal for themselves. Let’s say I want to do $100,000 in revenue, or a million dollars in revenue, whatever it is, they’ve got a really big number, and they’re at zero. And they have no idea about the incremental steps it’s going to take to get from A to B.

And so, this workbook will have you plug in some numbers, and then break down exactly the daily activities that you need to do …

Andy Baldacci:    Awesome.

Jim Brown:    … in order to be able to hit your goal. So, again, that’s just

Andy Baldacci:    No. And that’s the perfect type of resource for this audience, because listeners of this show, they’re not afraid of the work, but there’s so many times, especially in those early days, where that first step can seem so insurmountable, because you just don’t know how to get started, and so, I’ll definitely get all of that linked up in the show notes, and recommend to you listeners. Please check that out. And Jim, thank you so much for your time today. It was a lot of fun chatting.

Jim Brown:    I had a blast, Andy. Thanks so much for having me.