Brian Signorelli

Author of "Inbound Selling: How to Change the Way You Sell to Match How People Buy", Brian Signorelli offers actionable advice on how to be a better salesperson and falling into the trap of doing sales the way it's always been done.


Sahil Mansuri: Hello again and welcome to another episode of The Future of Sales show. I’m your host Sahil Mansuri, founder and CEO of Bravado. And with me today is a guest that I’m so excited to have on, someone who’s readily and quickly become one of my dear friends and someone who is now a published author as well, Brian Signorelli. I’m sure that takes some getting used to, Brian, to have that attached to your name.


Brian Signorelli: Yeah. What I really want is for my brothers to start referring to me as this is my published author, brother, Brian. You know, that’s really -- that’s like where it, you know, becomes real and where I really relish in that. But no, I mean, yeah, I don’t know how many people have referred to me as a published author but --


Sahil: But, surely, yeah, I have the book. I was going to bring it for the purpose of the show so I can hold it up and demo it. But I have even better news, I read it and I liked it so much that I shared it with another Bravado member who is actually asking me some questions about, you know, in a world, and we’ll get into why and how. But quickly, so Brian Signorelli is the head of the sales partner program at HubSpot and the author of Inbound Marketing: How to Change the Way You Sell to Match How People Buy, which is a fantastic book.

If you haven’t had a chance to check it out, I think by the end of this episode you’ll certainly going to want to because Brian is the man and talks about a lot of stuff that I think we hold very near and dear to our hearts hear at Bravado and themes that you’ve seen across a number of other, you know, episodes here as well. But Brian, welcome to The Future of Sales show and I’m so excited to have you here, man.


Brian: I’m pumped to be on with you. This is great. You know, things have just developed so rapidly in our relationship. You know, I feel like it was only a couple of, I don’t know, months ago that Derek Wyszynski who wrote the concluding chapter which is actually called The Future of Sales, I believe. He introduced me to you and here we are, and it’s great to have synced up with you despite the fact that we’re separated by, I don’t know, a few thousand miles from coast to coast, no big deal.


Sahil: Or one tiny line on the screen depending --


Brian: Yeah, by -- yeah, one tiny line, that’s what 3,000 miles’ now, it’s nothing. So, yeah, it’s been great to get to know you a bit and I’ve been, yeah, psyched to learn all about Bravado and what you guys been up to and to be a guest to chat with you today.


Sahil: Cool. So, first maybe just for some context for our audience, what the heck is Global Sales Partner Program and what does that mean that you exactly do?


Brian: Yeah. So what we should have probably named it, the reason we call it the Sales Partner Program is that we have three different major product lines at HubSpot. We have a marketing hub, which is a set of marketing automation tools. We have a sales hub which is sort of -- it’s a CRM and it’s a kind of sales engagement or sales acceleration tools, however you kind of think about that. And then, we also have a service hub which is basically for customer success and customer service.

And so, anyway, when we started building out what is the sales partner program, that was designed to be a partner program for businesses who would layer services on top of our sales products. So, really it should be called kind of like a CRM integrator or like CRM partner program, kind of similar to, you know, like the way a Salesforce partner might work or a Dynamics partner, things like that. That’s the kind of, you know, ilk from which the program was -- or the cloth from which the program was cut rather.


Sahil: Got it. Awesome. So, you know, one of the things that I learned very early on in our conversations is that your perception and perspective of the profession of sales is very unique, and I think you have a unique story into how you got into sales which you talk about in the book. I’d love if you could share a little bit of that because one of the things that we’ve found is that, you know, 4000 universities in the United States, less than 100, I think 70 on have a major in sales. And the reason why I find that particularly alarming is that sales is the number three most common job out of undergraduate for, you know, someone starting out their career.

It’s the third most common profession for someone fresh out of school, yet, yet, there’s no major around it, there’s no training around it, right. Every person I’ve ever met, myself included, accidentally fell into sales, right. And sales has this weird negative stigma around it and there’s this whole thing of, you know, you’ve obviously addressed this a lot in the book as well. But, you know, maybe you can start by sharing a little bit of your background in sales and then, also kind of how you think about the profession as a whole.


Brian: Yeah, I’m happy too, so I try to keep this tight. So, when I graduated from school I, like most people, had no idea what it was that I wanted to do. And I had a friend who was a couple of years ahead of me had, you know, graduate -- I mean I was a senior and he had graduated I think two years ahead of me. And he was working at this company in Washington DC called the Corporate Executive Board which is now Gartner, actually, reacquired by Gartner I think about a year ago. And he said, “Yeah, like you get to work with Fortune 500 executives and do research and write like White Papers and case studies and, you know, you get to learn about like the best practices and best solutions to the world’s biggest management challenges, and you should come work us.”

Like, “That sounds cool, what would I do for them?” He’s like, “Well, you know, like we’ll train you.  You’ll write white papers and case studies and you’ll take like research calls and blah, blah, blah, blah.” And I was like, “Alright, whatever, like, sounds good.” And then, I ended up basically doing like advisory work for like Chief Technology Officers and heads of R&D, which like I didn’t have an engineering degree, so I had no business this whatsoever. I could listen usually, I could write okay at best. And, you know, I guess, I had enough kind of like natural curiosity that that just, you know, and I was open enough to being trained, you know, they say that like the main purpose of a liberal arts degree is like not to learn new thing but to learn how to learn or something like that.


Sahil: Yeah.


Brian: Yeah. So I felt like, I guess, I was somewhat set up well to do that. And you know, fast forwarding through this, like as a research analyst I got exposed to the sales team there because what would happen is like the research analyst, like in a -- Gartner is a professional services firm, right. And in a professional services firm, the equivalent of a sales engineer is an analyst, basically. And so, the sale reps would bring me on to calls and they say, “Well, we have our --” yeah, they give me some ridiculous title, “We have the managing director of our research, blah, blah, blah, you know, that could talk to you about, you know, setting up a global or managing global R&D teams.”

You know, and here I am 23 years old. And I knew what I was talking about, but I only knew about it because I talked to tons of other, you know, Chief Technology Officers at huge companies who had done this and I was just kind of playing back those sound bites as, you know, like a monkey or whatnot. And I don’t know, like I just observed the way these sales people were selling and I was just -- like my jaw was on the floor and like this is awful. I can’t believe that this works.

And then, I got mad because I was thinking like, I knew that they got paid like three times or more as much as what I was getting paid, oftentimes way more that even. And I’m like, “This is bullshit. Like I’m doing all the work, I’m creating all the value, you’re just -- and on top of that, like I’m kind of selling for you because, you know, you’re just getting people on the phone, but I’m the one doing all the talking and sharing all the insight and all that stuff.”


Sahil: Right.


Brian: It’s hard work, right. Probably the same, you know, dichotomy or relationship that exist between -- frankly, between, you know, at a software company between engineers and sales reps today --


Sahil: True.


Brian: -- in a way, right. So anyway, kind of fast forward, fast forward, I didn’t like sales then. I then want to go work at a startup. I hated sales even more being a buyer and observing more and more sales processes. And then, eventually, someone said, you should talk too, because I was supposed to be running all of sales and marketing for the startup and I had no business doing that, no idea what I was doing. But I thought -- I’m like, “Oh,” you know, my arrogant 25-year-old self thought, “Oh, those sales people, like that’s such an easy job. I could easily do that in marketing like whatever, like how hard can marketing possibly be.” Of course, I was dead wrong in so many different ways and it’s incredibly difficult, both of those job -- or both of those disciplines and functions are incredibly difficult, but I didn’t know any better.

And so our sales and marketing was going horribly and someone said, “Why don’t you talk to HubSpot? They have a kind of different take on sales, different take on marketing.” And for the first time I was kind of exposed to an entirely different sales process. I’m happy to elaborate on that, but like that’s when my mind started to change about sales so much so that I can of fell in love with the company and I’ve sort of had this kind of like, I guess, seven-year love affair ever since then. I was a customer for a year and then, I went to go work for HubSpot and I became a sales rep in the process. So, I kind of went from, you know, hater to lover overnight or something.


Sahil: It’s so interesting. There’s so many parts of that story that I want to dig into. You know, there’s so much there that’s really interesting. But I think if I were to segment out what you said into a couple of different components, I would say that the first part is the realization that the profession of sales can be done well and it can be done poorly. And most of the time, it’s done really poorly and it ruins it for everyone else. And then, when you do it well, it’s such an exceptional experience that those companies and those people just win. That’s been my experience as well. you know, I have the exact opposite track as you where I started out in sales, I spent the entire career both as individual contributor, as a sales manager, as a Director of Sales, a VP of Sales, a CRO, eventually, VP of Sales and Marketing, and I kind of -- the same sort of tipping point, and then, I actually ended up on the product side, and I became a buyer and completely remove from the world of sales.

And that was my big awakening of like, holy shit, like most sales people suck, you know, because as a sales rep, you know, as a sales rep you don’t interact that much with other sales people in a professional context. In a personal context, I mean, salespeople will run like any other team does, right, you run with your pack and that’s just the way it goes and so, most of my friends are sales reps. But I had never had the experience of having to go through multiple qualification calls. I had never had the experience of having had five or six different account executives from competitive technologies pitching me to try and get me to buy their software. And once you go through that experience, you realize just how fucking annoying it can be. And I say that not as somebody who doesn’t love sales people, in fact, I mean, it would be asinine for me to be building Bravado if I didn’t love sales and sales people, you know.


Brian: Yeah.


Sahil: It’s the fact that I hate sales done poorly. And a friend of mine Kevin Walkup who is a sales rep at a company called SalesLoft likes to say, you know, “If you take a shortcut you’ll always end up cut short.” And I feel like sales is very much like that where there’s just a lot of shortcuts taken. You know, someone says, “Oh, I’ve been doing research on your business.” “Oh, really, what did you find?” Like, “Oh, it looks you’re hiring for a lot of positions.” “That’s interesting, we don’t have a hiring page, you know, like we don’t have an open an job, so where did you do this research, you know.” And, it’s just so glib for people to lie. And I think that one of the things that struck you early on in your career was the relative lack of integrity and just the general sense of dishonesty that’s around the profession of sales. Where does that come from, you know, it seems very asymptomatic specifically to sales? Where does that come from and, you know, why haven’t we gotten rid of it yet?


Brian: Wow, I mean --


Sahil: And you can use the easy questions first.


Brian: Yes, I mean, easy, the softballs.


Sahil: Yeah, yeah, yeah.


Brian: No, no, I mean, I love -- this is the stuff I love. Yeah, you know, I think it was driven by a few things, you know, like what’s really interesting -- I’ll keep it simple. I get trapped into making things way too complex sometimes. Like, I genuinely think that the sales profession is living -- it’s still living through this like 20-year hangover of how sales used to work before buyers were empowered with information. What do I mean by that? The year, let’s just call it 2000 just for sake of simplicity.


Sahil: Sure.


Brian: This is when the internet started to really take hold and become mainstream in many homes, many businesses and there’s just like amazing Katie Couric clip that I -- I think this is form like late ‘90s that -- have you ever seen this where she’s on and it’s like on a Today’s Show and she’s like, “Hey can we have someone come on and tell us what internet is?” Right? Tell us today, like, okay, it’s hilarious, and of course, it’s the internet, right, or just call it Google, however you want to think about it. Anyway, this company that you might be familiar with being in, you know, San Francisco, this company called Google came along and really -- with a variety of others in fairness and really democratized access to information. That’s a big deal, like, you know, we forget like especially anybody who is younger than we are.

And I think that like you and I are probably right on the cusp of this, but we’re just old enough to remember what life was like before the internet was really mainstream. Like if you wanted to find information you had to like get it from the television, get it from the newspaper, you actually opened your doors when someone knocked on the door, right. Like, people just going door-to-door. You’d, like, usually picked up like getting a phone call at home was actually a big deal. That’s just like before cell phones, like the phone would ring --


Sahil: Right, right.


Brian: -- like getting them during dinner, like your parents maybe, you know, if you did that thing like when you had family dinner, like parents can play like, “Oh, like, damn it, those phone calls during dinner.”


Sahil: Yeah.


Brian: Right? That was a thing like that’s -- and then, if you wanted to like write a research a paper, you know, or had to do a like a term paper for school or something or a research project, damn it, you went to the library.


Sahil: Yeah, what a concept.


Brian: What a concept, right?


Sahil: Yeah.


Brian: Today, it’s all right here, all of that. Anything you need is right here and I think that’s the long and short is that, you know, pre-2000, buyers in general do not have extra information. The sellers had all the control. Fast forward, you know, what is happening and happened over the last, say, 18 years is that buyers are taking control back and I think they’ve actually already taken a lot of that control back. And I think that frankly the kind of crap behavior that you see still happening today is a result of the fact that there were a bunch of people, there are a bunch of people now who are probably in their 40s, 50s, and 60s who were trained in sales before the information revolution, so to speak, before the democratization.

They are unfortunately just training, and it’s -- I don’t blame them, they’re training today’s sales force the way that they were trained before the internet happened, so to speak, you know. And so I kind of personally think that the sales profession is living this hangover of yesteryears’ sales process and sales training. And I think in another 10 years is going to look extremely different, maybe in the next 5, I think it’s already starting to look a lot different. People are just now kind of catching on to the concept of -- concept of like inbound selling, social selling, even a challenger sales kind of a new framework and all about taking control of a conversation, delivering insight realizing that the buyer has so much control in where and how they access and when they access information. That’s the long and the short of it like in my opinion.


Sahil: Okay. One -- I’ll challenge you on that a little bit, because generally what you said is obviously true, right, which is that buyers have control, have all the information, you know, whether you use third party sites on a professional scale of the Gartner’s and the Sirius Decisions in the Forester. You use the open comers, like the Trust Radius and G2 Crowd and what not type, crowd source reviews whether you go and download case studies off of websites and download contents there, whether you are able to easily use LinkedIn to reach out to your network in order to build, you know, build a framework or a, you know, kind of like wisdom from your friends of like what have you used, how does it work, right, across the board, right, across all of those boards, you have access to more information than you ever did. Great, I believe you.

But, but over the course of the last five years, seven years, we’ve had the rise of the SDR and in some way that seems to be very counter to what you just said, right? So, if we’ve had the rise of a class of an entirely new profession in sales because it’s never was -- this was never a thing that existed specifically in software sales, at least not in this way, definitely not with this level of prevalence, except for the last five to seven years. You have technologies like SalesLoft and Outreach and whatnot that are powering this world. You now have an army of 22 to 27-year-olds who are sitting there all day sending emails, making calls and basically firing out, you know, thousands and thousands of messages in order to get the first, you know, few hundred, few thousand customers for a visit, sometimes beyond that even, you know. So how do you -- how does that work, how do you at once have far more informed buyers and at the same time an army of junior sellers who are out there like firing outbound cold messaging, how does that work?


Brian: Yeah, so I mean, what’s really interesting about that and I think it’s a fair point is I would actually use that data point as a piece of evidence to supplant the notion that sales is getting harder. If sales are getting easier, I don’t think you’d see all these companies hiring armies of SDRs. If sales were getting easier, I don’t think that you would have seen-- literally, in the last two or three years, we’ve been an explosion in the sales technology space.


Sahil: Uh-hmm.


Brian: The landscape has gone from like, I don’t know, maybe a hundred or so software tools, almost a thousand.


Sahil: Yeah, sure.


Brian: This is backed by 10 billion dollars of venture capital, you know, that space is ballooning much in the same way that the marketing space ballooned from, say, 2000- I don’t know, 2009 to 2015, like there is this kind of marketing renaissance. I think we’re going through a little bit of a sales renaissance too in a way in terms of all these explosion. So I think that those things just support the fact that like sales -- that sales is getting harder, you know, and I think, you know, tying it back to the idea of like why do bad sales reps still exists, which I think was, you know, one of the original points we touched on.

You know, I think it’s -- personally, I think it’s tied, you know, in addition to the fact in my opinion that, you know, the dynamic between buyer and seller changes. Like kind of pre-2000 seller has all the control, post-2000 buyer has not all the control, but like a lot of the control or at least way more control than it ever had before. So, that’s a good dynamic that’s kind of the paradigm shift, so to speak. But I think it’s also driven by, you know, and I think -- and then, as the buyer gets more control sales as a function is fundamentally getting harder, you know, so you see the rise in hiring these armies of SDRs mostly inside sales, the shift away from outsides sales, it’s an explosion of sales technology. And then, I think, you know, the other things that are driving this kind of bad sales behavior is, yeah, I might be blasphemous but I’ll say it.


Sahil: Say it.


Brian: I think quotas are one of the primary reasons that you have bad sales behavior. I mean I could touch on things like, hey, you know, like we don’t have professional standards, right. We don’t have like a sales certification that every single sales person has to go through. We don’t have like a code of ethics that like every salesperson needs to adhere to, the same way that people on financial services, God bless them, my whole family is in financial services. Financial services are supposed to go through, our lawyers, our doctors, et cetera, like we just don’t treat the profession the same way. You could argue that. You could argue like -- and I love that point too about, hey, you know what, sales is not being taught in undergrad institutions, yet, it’s the third most common jobs someone is going to have. I think that’s absolutely part of it too. But I think at the end of the day, just my opinion, I actually think quotas are a huge part of the problem, if not the entire problem.


Sahil: Okay. So, you know, I was -- one of the things I love about talking to you is that we could literally talk about any topic and get so nerdy and deep with it. I haven’t had this conversation yet and I’ve been dying to have it. So, you inadvertently touched the third rail on this one, because this is something that fascinates me, which is to say that -- yesterday, I was at -- a VC here in San Francisco hosted a sales summit that I attended and they had a panel of this like extraordinary sales leaders who came and spoke, you know, sales leaders from companies like Glassdoor and Marketo and SAP and Salesforce and, you know, whatnot, App Dynamics. And they’re sitting there and they’re talking about how to build a winning sales culture and all these things and they’re sharing their insights.

And one of the things that they asked was that we not publicly share the things that they said because they wanted it to be kind of confidential conversation in the room for sales leaders. And so, I’ll adhere to that and we’ll get into that minutia of what they said. But one of the things that came up was compensation and I asked the question of it’s like, hey, you know, they were talking about how you want to build a comp plan that’s extremely aggressive and that rewards your top performers and that you want no more than 45 to 50% of your reps hitting plan and, you know, if you hit above plan, we want to pay you like 200% of your OTE or 300% of your OTB and take millions of dollars, but you gotta be above the line and if you’re not above the line, you’re out, right, feast or famine, you know, kill or be killed, sort of a rah, rah sales culture.

And I’m just listening to this and I’m thinking to myself, imagine if instead of this audience being a roomful of sales leaders, this was a roomful of your customers, like just imagine that, right. Imagine for one second if I had recorded that conversation and if I played it to your customers and I was like this is how this company thinks about the -- thinks about their -- the way that their salespeople should be compensated because these are the values and these are the behaviors that they want to incent, which is to say we want to incentivize sales people to like blow out their number. What does it mean to blow out your number, right? What does that actually mean? So let’s talk about what that means.

There’s one of the couple of ways you can blow out your number as a sales person. One of the things you can do is you can either sale a lot more deals, right, you can increase the quantity of deal. But that means -- but now, either that means that you’re like a magical unicorn salesperson who is able to find every single qualified prospect in your territory and sell to them, if that’s who you are, then great. But the majority of what that means is that you’re really good at selling deals to people who otherwise shouldn’t be buying your product or otherwise isn’t a great fit, but you’re really, really good at convincing the person that they should buy it.

And so what that means is you have worst fitting customers that are in your -- that are joining your cohort of clients and then, you know that a certain percentage of those people are going to churn, but you’re willing to do that anyway because you want to increase topline revenue. So, that’s the potential with that. The other thing that could mean is that this person is really good at selling either SKUs that the customer doesn’t need or is good at getting the customer to pay a higher price than they actually should be paying, right, that’s the other thing that that means. There’s only two ways you can blow up your number, right, more deals are bigger deals, right.


Brian: Right.


Sahil: If it’s bigger deals, then, yes, the person could be a fantastic solution consultant who’s able to get deep within each company and be able to create value across the multiple organizations of the multiple teams of the same product and different use cases. And again if you’re that sales person, I commend you, right, and I truly mean that. But for the majority of top performers, what it means is that you’re really good at negotiating and you’re really good at obfuscating the price and inflating it and putting bells and whistles in there that the customer doesn’t really need but that charges them a little bit more money.

And I think that, you know, this entire concept of commission-based sales people and quotas is -- I just cannot believe that there has not been companies out there that have been like, we are not going to commission our sales people, we’re not going to offer quotas, we’re not going to reward you based on the percentage of deals that you -- percentage of goal that you hit. But then, it’s almost like -- and so I ask the question, I was like, so you know, is there ever a world in which you can imagine the sales team not having a quota. And universally, all three of them are like not between zero and a hundred million, right. Between zero and a hundred million, you have to have that. You need people to do, you know, things to get the business and you need to create that culture, do you think that’s true? I don’t know. I am skeptical. I’m skeptical whether that’s true or not.


Brian: You know, I don’t know. I don’t know. I really don’t know the right answer to that. There are very, very, very few examples that I’m able to find and I can assure you it’s not from a lack of trying to find them. Atlassian is one of the only companies I have ever found that I’ve -- that I can see who have done this, who have said there is no quota there aren’t even sales people. There are -- I think they call them like customer success engineers or something along those lines and any of those things or really any time that I would even share the Atlassian example, like all sales doers come out and they’re like, yeah, but that’s just tech, and yeah, that’s a different buyer and yeah, it’s like a lightweight product and they just -- they come out with every objection.


Sahil: Of course.


Brian: Right. But if you watch -- it’s a really interesting video, I mean, for anyone who hasn’t seen it, watch -- I always get his name mixed up, it’s Jay Simon, singular, not Simons, I think it’s Jay Simon, the president of Atlassian, watch I think thru YouTube, you can find it. Watch Jay Simon Startup Grind 2014 and he shows his video of exactly the story of how this came to be and what type of impact that it’s had on their business. And frankly, I think a lot of it, I mean, a lot of behavior is rooted in fear or in greed, in my opinion. I think those are some of the best human motivators that exist. So like however, you know, evolution kind of figure that one out, it’s great because like they work, they drive action.

I think what’s holding you back from doing that is fear or it’s just that people are saying, “No, I’m not afraid of it, like it’s just --” like I know that we’re creating a bunch of shitty customer experience along the way, I’m okay with that. I’m okay with that level of bad karma, I guess, that’s out there in the world. I’m okay with creating that waste; maybe the rest of the world is too, I don’t know. But what’s interesting of Atlassian is like -- and what I find interesting because you’ve seen, Sahil, you know, working at, you know, different software companies, usually if you look at the trajectory of revenue throughout a month, it goes like this. It’s like dot-dot-dot-dot-da-da-da-da.


Sahil: Yeah.


Brian: Like, you know, 50% of the revenue comes in like the last 10% of the month, sometimes like in the last day of the month.


Sahil: Sure, always. Of course.


Brian: And I’ve never like analyzed those customers and said, “Hmm, like I wonder, I wonder if the customers that are so -- I wonder if there’s any meaningful different between the customers that are sold on the last day of the month and the customers that are sold on, say, the 15th of the month.


Sahil: Okay. So what’s amazing about that and I -- and for those of you who are watching this, you probably are like, wow, these two have really done a lot of prep for this. I assure you we did zero prep for this session. I read an article on this very topic yesterday. So, I was sitting there and I was trying to like think about this topic and something that struck me was the fact that, you know, you pushed deals in at the end of a quarter, right, I was looking at it from a quarterly perspective of the time, the monthly, it applies the same. And I was like I wonder if those deals are worst deals or not.

So Ken Krogue who is the president of the Inside Sales wrote an article on HBR, Harvard Business Review, that specifically talks about this, that says that like there’s an 11 times greater probability that the deal that you close at the end of the month is more likely to churn than a deal that you close at the beginning. And you, basically, what you’re doing is you’re pushing in customers that are (a) not ready to buy or (b) are bad fits and you’re using the leverage of discounting and you’re using the leverage of, you know, fear and pressuring and this and that in order to cajole people who don’t actually are not really ready to buy but you get them to buy and then, the whole sales -- and then, you hit the gong and the whole sales team celebrates.

But the problem with that is that today, in today’s world, and this is what I see things changing is that in today’s world, we care so much more about retention, we care so much more about turn, we care about payback period, especially in Saas. And so, getting a customer to sign up on a discount today and then turning out that customer in 12 months actually losses the company money, you don’t even make -- it’s not even break-even that you could be like, “Yeah, well, you know, the booking is number one now,” but you lose money on those deals.


Brian: Yeah.


Sahil: And forget about the payout to the sales person, although that’s certainly a part of it, but we’re just talking about the amount of effort and time and energy it takes your customer’s support people to have to deal with all the issues they’re going to have and the sales engineers and then, your product roadmap gets influenced because they want features that they were promised that they actually can’t do and maybe it just -- it screws everything up. And it’s just incredibly vicious cycle that we hit, which is that, you know, we’re addicted to the number, we’re addicted to the hyper growth, everyone wants to be a hyper growth startup, right?


Brian: Everyone wants to be a unicorn, right?


Sahil: Everyone wants to be a unicorn and yet, you know, the reality is a lot of companies aren’t ready for that yet. What they’re ready for is to get a handful of customers to teach them what’s wrong their products and then, they’re ready for their engineering team to make some changes and then, maybe get a few more and then, maybe get a few more, but no one wants to do that. What everyone wants to do is just, you know, hit a million in MRR, hit this and hit that and get VC funding. And so I think it’s just incredibly, you know, deleterious cycle that we’re in. And to break free of it seems to require a whole scale systemic change in the way we think about building a successful technology.


Brian: Yeah, I mean, you know, I’ll probably be blacklisted from the entire VC community for saying this, but I think the cause behind the cause on quotas is VC money and I’m not saying all VCs are bad, they’re not. And I’m not saying the VCs are bad in general, like it’s not even that, it’s just like look, if I were a VC I’d probably think the same way. But the reality is the way VC manages money is they make a certain number of investments, they kind of spread that money around and they know that 9 out of 10 those, maybe more are not going to make it.

And so the day that they sign to a check to anyone of those companies that takes that VC money is the same day and I remember, this guy who created a very, very successful -- I mean, and granted this is like back in the ‘80s, he created a very successful basically -- I’m trying to think of the name of the business he was in. They basically provided like clothing to like the profession -- to the hospitality industry, right. So, like think of like all the uniforms you need to do, you know, in the restaurants and all that stuff, right.


Sahil: No, yeah, yeah, yeah.


Brian: Yes, the name of the company was called WearGuard. They’re acquired by -- I blanked on the name of company, but I’ll follow up with you on it. They’re acquired for some company for like, you know, half a billion dollar or something like that and they became successful through mail order catalogs which was like the equivalent of inbound marketing in the ‘80s.


Sahil: Right.


Brian: It was innovative back then, I know it sounds crazy now but that was like a big deal. Anyway, one of the things he said to me because I was going through this process of unsuccessfully trying to raise VC money before I went to HubSpot, he said, “Brian, be really careful because, you know, if you are lucky enough to have a venture capital firm invest in this business.” He said, “The same day they right you that check is the same day that a shotgun goes to the back of your head and they are just waiting to pull the trigger and be very careful in that.”

And then, that feeds down into the board, that feeds down to sales management, that feeds down to sales reps, and it doesn’t end there because once you go public then it’s Wall Street, right, which I’ll get even more, you know, more hate mail for it probably, but, you know, just bringing these things to life because this is how -- these are just my thoughts, these are just my opinions, it doesn’t mean that I’m right or wrong, it’s just what -- it’s what kind of goes through my head on these things.


Sahil: Yeah, I mean, so, you know, there’s an article that I published on the Bravado blog that actually talks specifically about this topic. Again, I swear we didn’t do a prep call for this. All right, very interesting how we seemed to be -- we seemed to be interested in the same things and what we’re referencing is the power law of VCs and how that works and, you know, I think we’ve had a number of pieces of content that we’ve referenced throughout this and what I’ll do is actually grab all of those lengths and post them at the bottom of the -- in the comment section so that you can actually read through and reference, you know, the things we mentioned.

But, you know, I think I agree with that as well, which is to say that, you know, there’s an expectation of hyper growth when you accept venture capital. And then, if you, you know, you’re not able to manage those expectations properly and not set those expectations upfront and not be transparent in your communication material VC, you know, then, you’re setting yourself up for failure. You know, we are VC backed company and I will say that I have been incredibly lucky to work with a VC, you know, who actually herself was a two time founder and has sat in my shoes, at my stage, in my seat and has like felt this pain herself, you know.

And so, you know, when we have conversations about this, she’s very like, “Look, I know these are the expectations, but I understand the way you want to build the business and like I want to be respectful to that and like --” and we are very candid with one another and I have just so much appreciated, you know, working with her. Now, that being said, that is, you know, not the rule that is the exception, and I think that the majority of times in which I’ve worked as a sales leader at VC backed companies, which I’ve done a few times down in my career, there has always been that expectation and that like dread of the board meeting and that’s pushing this behavior. And I can’t even tell you how many times I was asked by the CEO of the company that will go unnamed to, you know, either pull in a deal that should count for next month and like do some weird thing on the contract so it looks like accounted for this month. And you know, in the first time, you get asked to request like that --


Brian: That was pervasive, so many companies, I mean, like, you know, without naming any companies, you know, I have countless stories of how many times, you know, a sales manager would say something like, “Hey, you got anything for next month, you can pull forward. You pull -- yeah, yeah, yeah, like I know, I know it’s like post-dated for next month, but you like pull it into this month, like we need it, team needs it.”


Sahil: Yeah, team needs it, right. We need it, right. And so, you know, the level of dishonesty isn’t just between the buyer and the seller and I very much agree with that. I think we are internally dishonest with ourselves and I think we are dishonest with our boss, which is often our board and then, within that communication channel as well. Look, at the end of the day, we are in a world in which people try to fake it until they make it, that’s like a very, that is like the strategy that most startups, use, right. It’s like just create enough of an aura around yourself so that your -- so that people believe that you’re more successful and bigger and better than you are and then, hopefully you’ll live up to those expectations one day, but most of the time, you don’t and you fail. And then, that’s like that’s like accepted too, right, in what you said, right, in your whole concept of 9 of 10 bets don’t go well anyway. So knowing all of that, let’s bring it back down to the individual salesperson.


Brian: Sure.


Sahil: Which is to say, I’m a sales rep, I’m living in this new modern world where (a) VC money is everywhere, hyper growth is the table stakes to getting funded, I’m getting pressure from my leadership team to hit numbers, I’ve got a comp plan and quota that incentivizes me to blow it out of the water, whatever that means. So, then let’s bring it back down to reality, I’m a salesperson talking to a customer, right, the customers are far more informed, the customer knows what other people have paid for this software, they have a much better understanding of just what your technical capabilities are. How do I balance that because at that point, I’m kind of serving two masters, right?


Brian: Yeah, yeah, I mean, like the quota thing, it’s -- look, there are things in your control, there are things that are out of your control. I’m not saying that the oppressed salespeople of the world to rise up against, you know, the quota setters, you know. I’m not saying that, it’d be interesting if that happens someday, but I don’t think it’s going to happen any time soon. I’m not advocating for that. So kind of realize that’s probably out of your control, like you got to have a number, then you’ve got to manage it, okay. My opinion, the time that as a buyer, actually, when things clicked for me and I said, “Ah, like, not all salespeople are shit.”

And I actually feel okay cutting a check for like maybe not anything but like kind of whatever was the first time that I dealt with HubSpot. I’m not saying that everyone at HubSpot does this necessarily, I’m just giving you an example because that’s on a context reference point, well, one that changed for me. It doesn’t matter if it’s HubSpot or other companies, but what HubSpot did was so different that I noticed it, okay. And so my message for any sales rep today is if you are following the playbook that a bunch of other sales reps before you have followed, you’re probably not doing it the right way. And I think if you couple that with, you know, picking your head up, looking around, asking yourself like how do I buy in my personal life, what expectations do I have of other companies, okay. So like I’ll give you a couple of quick examples, like when you buy from Amazon, would you say it’s a hard or easy experience? You’re going to say it’s the easiest. You’re going to say, “I am addicted to Amazon, it’s so easy,” right?


Sahil: Yeah.


Brian: Okay. So think about that for your buyer. Figure out how do you make it as easy for them as possible, think about like unexpected moments of delight. I’ll give you another example, Uber. All right, I know Uber is a little bit in the dog house recently, but whatever. One of the very first customer experiences I had with Uber was that they rounded my bill down to the next closest dollar. I said, “Huh, I’ve never seen that before. It was like my bill is $15.16 or like just call it $15.” Like that’s great. That’s amazing. I don’t give a shit about the 16 cents and the reality is they don’t either. But what they created was someone who is now an Uber loyalist, I mean, granted, you know, I’m one of --I don’t know, millions or billions, whoever -- whatever using Uber now, but kind of unexpected moment of value or delight, the list goes on.

I mean think of Zappos free shipping, Amazon free shipping, both ways, all these things, right. So look in your own personal life, think of how we’re living, if I could sum it up, you know, people say they were living in the age of or they’d say we’re living in the information age where like, you know, buyers have access to all this information, all this information, all this information. I think we’ve actually transitioned out of the information age and we’re currently in the age of convenience where we expect that everything is personalized, that it is easy, that it is fast and that I can try a bunch of stuff before I buy it, okay. And if you take some of those principles into your selling, I guarantee you, you are going to be -- you are going to stand out significantly to any buyer.

And I think you’re going to build a bigger pipeline than any sales manager could ever ask you to build and you will blow out your number, maybe not right away but it will take time. But, you know, over time I promise you that if you start to behave and keep those kind of, you know, grounding principles in your mind, I assure you, you are going to win because what you have effectively done is you’ve changed or adjusted the way you sell to match how people want to buy.


Sahil: Right. And I think that the -- using B2C as a way as a way to contextualize B2B is a really helpful exercise and I think it’s one that we don’t do nearly enough when we’re looking at ourselves in the mirror. You know, you mentioned some good examples. I’ll give you another one, Netflix, right. I hear about Netflix and like, “Oh, cool, I want to go check it out, maybe I’ll use it, right, and I show up on their website. What do they advertise? One month free, no credit card required, click here to start your trial, right? Like, click a button, boom, I’m in. Now, can you do that with enterprise software? No, of course, you can’t, right, because you’re not going to be able to deploy some crazy BI tool that’s going to look at like billions of records in your database and be able to like give you any sort of sense of value, of course not, right.

So, I’m not saying that like, “Oh, yeah, you know, this is great for companies like Zoom and Slack and whatever where like you can really just like click and buy.” But, you know, you’re not going to be able to do that with something that’s complex. So what can you do? What I think you can do is to, you know, Jill Rowley who is one of my favorite people, she talks about this and she talks about the system of deposits and withdrawals and she says, “Before you go to the bank to make a withdrawal you got to make a deposit because, you know, it doesn’t work the other way.”

And I think sales is much the same, which is that, you know, you get on the phone, “Hey, can I give you a 15 -- can I take 15 minutes of your time to learn about your business?” No, you may not, right. You can’t get 15 minutes of my time to learn about my business, to hear about my hiring needs, to discuss how we can help you, you may not do that. But if you find that I, you know, I think you gave me this example previously about something that HubSpot does, and I have to admit that I’m a big fan of HubSpot’s approach, you know, I know and I’m friends with Mark Roberge, you know, I know Vulpi and Joe Chernov and I know a lot of the gang from HubSpot. You know, great, great group of people, you know, David Cancel and kind of the entire kind of HubSpot mafia is of doing some really amazing things.

And one of the things that I think HubSpot delights in is the fact that they come at you not with a “Hey, do you want to take a demo of our product,” but they come at you with you actually creating value for your business and then, inadvertently or as a secondary ask they will then try to pitch you a product and we don’t need to be just ingenious here, right. I’m not saying like lie and don’t be open about the fact that you’re a salesperson, I’m just saying make a deposit first in the account before you make a withdrawal. And I’ll give you an example of something that we did at a company that I worked at which was -- which I thought was really great, you know, it was a very effective strategy for us.

You know, I used to work for a video advertising company and we used to basically help you get more views on a video that you created, right. So, that was the general concept. And so, how would we approach people? Well, we built this diagnostic tool that would look at your video that you had posted on YouTube or whatever and we’d look at how many views it has, what is the average view time, how many social shares it has, how many people posted on Twitter, and we would just basically look at the health score of your video and we would email prospects not to say, “Hey, set up a meeting with us.”

We would say, “Hey, we run a quick diagnostic of this video for you. We’ve figured out that given the number of views that the video has in your average view time, here’s what industry expectations would be in terms of social sharing. But as it turns out, you’re a little bit behind and it looks like you’re doing really well on Facebook, but Twitter and these other channels are going less well for you and blah, blah, blah. We compared it to this other video you ran a few months ago and it looked like that went a little bit better. You know, maybe -- here’s a couple of reasons why we think it might be this way. We want to shoot this over to you and see if, you know, it would be helpful. Would love to chat if you’re interested in video marketing solutions.” And the response rate that we would get to that, I mean, what is -- I think 600% to 700% better than any cold email I’ve ever written in my life ever and --


Brian: Yeah, you made a fat deposit in the bank, right. You’re saying, “Hey, like, here’s the thing that might help you.”


Sahil: Yes.


Brian: I’ve done some research on you, I already know about you, I’ve actually taken a step further and found something that you care about and I’ve analyzed it for you and here are the results. If this is a priority or something you want to chat about further figure out, you know, how you can improve this or whatever that is, whatever that call to action is, it’s adding real value. I think that’s one of the things that I hear so much about and I think I’ve ranted about at different points. I try not to rant but it’s just -- I don’t know, I think it’s just the way that I write tends to be ranty which I’m not.


Sahil: You and James Joyce.


Brian: I guess, yeah. So I just hear a lot of people saying stuff like you got to add value, you got add value or like sales reps are saying, like I add value, and I asked myself, I’m like, “What is value?” And I know we’ll get into really like ethereal philosophical --


Sahil: Sure.


Brian: -- you know, space here.


Sahil: Let’s be there


Brian: We could be there. Without, you know, getting too into it, I think, you know, obviously, what you -- like I think it’s awesome like what you just gave is an example of real tangible value, that’s it. Okay. My advice to anyone, unsolicited advice to anybody who’s listening to this and saying, “Well shit, like I don’t have a diagnostic, I don’t have an engineer that can build this thing for me, you know, HubSpot, you guys have website grader, Sahil, this company had its video diagnostic, that’s awesome, but guess what, I don’t have that,” right. I say okay, fine. What do you have?

Well, one of the things that every single salesperson has is extremely unique point of view, if you are listening. Because if you’ve been doing your job, even if you’ve been doing it poorly, okay, for a year, two years, whatever amount of time you want to take, you are talking to tens, maybe hundreds, maybe even more people who your company should be serving, right, or could be customers, already are customers, whatever, and so you sit at this really unique intersection of all these peers, right. So, let’s say you sell the heads of sales or heads of marketing, right, maybe heads of marketing; you have tons and tons of conversations with heads of marketing every single day.

And so if you’re listening, you should actually have a pretty good sense unless you are just saying, “Hey, you want a demo, do you want a demo,” right? Instead if you’ve actually asked the question and said like, “Yeah, you know, like most companies I talked to are struggling with thing one, two, three, you know, to what extent of you -- has that come up within your organization,” right. If you’re listening, you’re going to hear a bunch of unique perspectives about what other people are struggling with and that in itself is the inherent value you can bring.

It’s the actual insight of -- and that synthesis of those tens or hundreds of conversations you’ve had and to say, “Hey, look, like I know you’re thinking about it that way, but over the last year, I talked about 150 different CMOs and frankly, what keeps them at night is thing one, two, and three. You said something that’s more like 9 or 10 on most people’s lists, you know, do you want me to share a little bit about what I’ve learned about how they’re addressing thing one, two, and three when kind of figure out if, you know, that’s even a priority for you all right now.”


Sahil: Yeah. I love it. Or even if it’s not that bold and all you do is just write down the things that people said and you’re like, you know what, you don’t even need to synthesize it. You can just present the materials, right. You can literally be like, “Hey, I’ve had conversations with the 150 CMOs over the course of the last year, everyone that I talked to I take out their name and their company because, you know, it’s confidential information, so anonymize it. But here are their top three biggest challenges that they face and here’s a couple of solutions and things that they’re doing to fix it. Do you want me to just send you the document I have?”


Brian: Yeah.


Sahil: And you just ship it over to them. I mean that is something that Forrester will charge you like $100,000 for, right, but it’s the same shit and you don’t --


Brian: That’s value, yeah.


Sahil: That is real value, right. You can quantify how much value that is.


Brian: Absolutely.


Sahil: And I think that is such -- so okay, so I’m so glad you brought that up because it reminded me of something you said earlier, which was that your role as the analyst when you were first working at the corporate executive board versus the sales person. I think we are in for another revolution in sales, which is already happening, but it’s the rise of the sales engineer, the solutions engineer. And what I mean by that isn’t so much that it -- well, on the one hand, yes, they should be more highly compensated and that there should be more parity in the way that they’re paid and like I believe in a lot of these things.

But to the core of it, as a sales person, you have to be a sales engineer now. It is not okay for you to be the quarterback of the deal and then, hand the ball off to the solution’s engineer and have them to run through the whole every time, right, that is no longer -- the job of the salesperson is no longer to call to play and to huddle, right, and to motion people around, like you got to be able to run with the ball, right. And if you’re -- and what that means is you need to have deep knowledge of your product, to have deep knowledge of your competitors, you need to actually use the product in production, not in a demo environment, in production. You need to have been responsible for the outcome that the product is driving.

So, yes, that means that if you are selling cyber security that it definitely means that you need to go hang out, you may not be able to hang out with every single head of engineering, but I bet you have one at your own company and I bet you could sit next to that person and, say, hey, do you use our own product? You do. Cool. Can you show me how it works? Can we try to -- can we try to hack our own system together? Can you even show me what it means to hack something? Can you, can we, can I learn, can I practice hacking things in our system and be like -- because then when you talk to the next head of engineering, you’re not going to sound like a schmuck that’s doesn’t know cyber security, right. You’re going to sell --


Brian: You have to walk a mile. You have to walk a mile in the customer’s shoes. I mean, I love that idea. I mean like the closer, the closer you can get and I know there’s like multiple schools of thought on like selling style, like I’m of the pain school. But the closer you can get to your customer’s pain, the better you are fundamentally going to be at relating, expressing empathy, understanding what someone’s day is like, and that, I mean, that’s a whole different layer of trust, of getting someone’s attention, of earning their respect. I totally love that idea, I mean, that walking of a mile is so much -- I’m sorry to interject there to --


Sahil: No, that’s exactly right. I mean, and I’ll tell you that I had the experience myself of having been a customer, and I think this is very similar to your experience at HubSpot where I was a customer of a company called SalesPredict and I’d used a bunch of other lead scoring platforms before back to our rise of sales automation in the sales tech world. And then, I became a customer of SalesPredict, I used the product for three of four months. I knew it wasn’t perfect. But I knew what it did really well and I knew it was better than what a lot of competitors offered.

And then, when they offered me a chance to come work at the company, even though I was running product marketing, I was still the person that they would call in right when the deal got really thorny, because they’d be like, all right, well, why don’t you talk to, Sahil, who’s our product marketing person, but he also used to be a customer of our product and he can actually show you how to really use it. And so, I would come in and I would open up their Salesforce and we would go in there and we’d start looking at leads and whatever.

And by the end of it, the customer, you know, if it was a good fit would be like, “Yeah, this is awesome.” If it wasn’t a good fit, I’d be like, “Yeah, dude, I wouldn’t use this product for this either,” right, like, I mean, and it was like very easy and natural. Now, that is the job of every sales person to me. And I think in order to be an exceptional sales person you have to be able to do that. And I think the fact that you are a customer of HubSpot before you were an employee of HubSpot gives you the credibility and authority to say that. If you’re a sales rep that’s starting on your career and you haven’t had the opportunity to be a customer of the product that you’re buying or you’re not the target customer, that’s okay, that’s okay too. But then, as much as you can simulate that world and until you can truly feel confident that whatever it is that you are selling is something that you deeply understand, you’re always going to sound extremely fake and untrustworthy.


Brian: That totally -- I mean, I totally, totally agree with that. Just replicating that experience understanding what, you know, keeps that buyer up at night, you know, how difficult it is to be them. I know it’s a really tough thing to wrap your mind around, but like I think you’re absolutely right and I could not agree with you more than in terms of where I think sales is going, I think it’s going a lot of places. I don’t think it’s a dying a profession, I don’t think it’s, you know, as cool as -- believe me, like I thought that Google Duplex demo was just, wow, I loved it. I really did.


Sahil: Yeah.


Brian: We got our ways to go. We got our ways like, you know, I think we’re alright for at least a few more years. We’ll see. But --


Sahil: You made a table -- to be clear, and I don’t mean to interrupt you, but I have to just throw this in. The Google Duplex thing was awesome, but what it replicated is what you can do with two clicks on OpenTable and I think we’re a long ways away from being able to even do what you can do on OpenTable with the piece of enterprise software. So, I don’t -- I’m not so worried about it either.


Brian: I mean, you know, probably afterward we’re long gone. I hope. You know, but every generation before us has probably said that. There’s got to be one that’s like stuck in the middle and it’s like, crap, “we’re the ones that didn’t die!” like, right now, you know. I hope that’s not the case. But I should totally subscribe to your school of thought on this, Sahil. I mean, it’s one of the things I tried, I guess, just because I’m nerdy, but I love the product, I was a customer, I love HubSpot’s product, I genuinely loved it and one of the things I taught my sales team members when I came in, I said, “Nothing will replace superior product knowledge, nothing.”

And some of them took it seriously and some didn’t, you know, and I agree that, you know, there’s -- I don’t if you ever come across -- so Pete Caputa was my old boss and he’s got the saying that goes something this, it’s like, it might only be relevant for tech companies but maybe not, maybe the whole world is becoming a tech company, I don’t know. He says that in the future engineers/product people are the new marketers. Marketers are the new salespeople and salespeople are the new customer success engineers, so to speak. And I actually -- I think there’s a lot of truth to that and I think it also ties back into this notion of, you know, intimately understanding your customer’s pain, helping them be successful with whatever it is that they’re trying to solve; frankly, whether or not your solution helps them with that or not.


Sahil: I love it. This has been such a great conversation. Sig, we got -- we just got to do a weekly show with you and if we could just -- yeah, we should just rename this thing into the Brian Signorelli Show.


Brian: Oh, no, no.


Sahil: And we just have you come in. No. And I mean that very sincerely in the sense that I just think that, you know, anybody who’s listening to this is going to look back and be like, man, you know, there’s a lot happening with our profession. It’s not that you have all the answers, it’s that you’re asking the right questions, and I think that, you know, where it really comes down to is that if you have never bought something, it is really hard to understand what goes through the mind of the buyer when you’re a sales person and you can think that you know but you don’t know. And it is only when you really know what goes through the mind of a buyer and what they’re feeling and what they’re truly thinking when they listen to your pitch and what they want out of a sales conversation that you can rise above the noise and become the type of salesperson that I think that we all want to be. So, Brian --


Brian: Good concluding thought, I like that.


Sahil: thank you so much for taking the time I’ve really enjoyed it. And Brian, if people want to reach out to you or have further questions, what’s the best way for them to get a hold of you?


Brian: LinkedIn is great or if you, you know, love Twitter, I weirdly, have two Twitter handles, so just @briansignorelli or @inboundseller, either one of those is fine.


Sahil: Okay.


Brian: Probably the preferred medium. So, yeah, feel free to reach out.


Sahil: Amazing. And again, the book is called Inbound Marketing.


Brian: Yeah, Inbound Selling.


Sahil: Yeah, yeah, yeah, I was going to say Inbound Marketing in the Modern Context, right?


Brian: Right, yes, exactly, exactly.


Sahil: Yeah, Inbound Selling.


Brian: It’s the successor or sister or companion to the book Inbound Marketing that our co-founders Dharmesh Shah and Brian Halligan wrote about 10 years ago. I mean, that’s the way I’ve always kind of aspired or hope it would kind of turn out. We’ll see, we’ll see if it does, but, yeah, it’s Inbound Selling.


Sahil: Inbound Selling, yeah, Changing the Way You Sell to Match How Buyers Buy. So, I love it. Thank you so much for your time. You’re so amazing and I’m thrilled to count you as a friend. Cheers. Have a good night, man.


Brian: Thanks, Sahil.


Sahil: Bye.


Brian: Yeah.

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