Are you looking to sharpen your skillset–to gain an edge in the fast-paced world of enterprise sales? Do you want to drive efficient, repeatable success without getting worn down? If so, David Perrys new book, Game of Sales is for you. Its the candid conversation you always wanted to have with a top enterprise salesperson.

He takes you behind the scenes of what hes learned working for top companies like Adobe, Amazon, Google, and IBM. David shares the tools, strategies, and techniques you need to beat your number and create mega deals.

You will discover the mindset needed to perform at the highest level and maximize earning potential over the long term.

Drew Appelbaum: Hey listeners, my name is Drew Appelbaum and Im excited to be here today with David Perry, author of Game of Sales: Lessons Learned Working at Adobe, Amazon, Google, and IBM. David, thank you for joining, welcome to the Author Hour podcast.

David Perry: Thanks Drew, happy to be here.

Drew Appelbaum: Lets kick this off, can you give us a rundown of your professional background?

David Perry: Yes, I spent the past 10 years or so working with world-class brands while focusing on the technologies that theyre looking to adopt across marketing and advertising in particular. But also focused on helping them create digital experiences.

You know, over the years, its been a really amazing experience to get to know these companies across various industries and figure out what really makes them tick and how we can bring our two companies together, so whichever company Im representing and theirs, to drive change and help to adopt technology that will make a large impact on their bottom line and ours.

Drew Appelbaum: Now, why was now the time to write the book? Was there an inspiration lately, did you have an ahamoment or did you just find some more time on your hands due to the COVID situation?

David Perry: Well, the COVID situation actually didnt help me very much in terms of time. The timing was that I had a pretty good year and I started realizing, over the course of the various companies Ive worked at, that things started coming together and I wanted to make sure I could really share that perspective, and writing a book is something that Id always wanted to do.

Drew Appelbaum: Were there any learnings or breakthroughs during the writing of the book? Sometimes its by doing research or that introspective journey back to your past in some of these positions.

David Perry: I mean yes, there were some incredible learnings over the course of writing the book. One of the things that I thought was pretty interesting is that as I was writing it, I became aware that there were some things that I was able to translate very easily, like the basic mechanics of how to build a pipeline, or how to draw intelligence out of industry research, how to build credibility with executives, things of that nature. But there are other things like the softer side–how to deal with the ups and downs in enterprise technology sales, and I would imagine in probably just about any job that that stuff is a little bit more difficult to translate.

It was a really immense learning process and learning opportunity overall. Having to articulate in great detail, all these elements and themes that I thought are really important for salespeople to learn, and a lot of the things that Ive learned the hard way, which Im hoping to help people short cut.

Technology Sales

Drew Appelbaum: Now, who is this book for? Is it strictly for software salespeople or can you find useful tips in here for other roles?

David Perry: I wrote this book for a very specific person. Its an individual that, lets say theyve been out of school for three to five years, maybe theyre making a hundred grand doing some type of technology sales, and they want to really cement themselves in the three to 500K range.

That is really the specific individual that I wrote the book for. So, what are the themes that they need to really dive into and the conceptual architecture that will help them get to the next level?

What I found is that, while I do believe that that individual would benefit from the book, its been interesting that Ive had some early reviews of the book where undergraduates and some people who are just about to graduate from college or recently graduated or even MBAs or people that are still pretty early in their transition into sales, they really enjoyed it but also.

I also found that people that were much more experienced in sales also appreciate it, especially the back half of the book where I go into some of those more challenging topics that I mentioned a few moments ago.

Drew Appelbaum: Now, lets dig into yourself a little bit David. How did you find yourself in sales?

David Perry: It certainly was not a straight line for me. I started out as an analyst working for a startup and I did that for a few years, and then I went to business school. It was really at the startup that I learned that I wanted to make sure that I was a little bit closer to the revenue-generating side of the business. Once in business school, I thought that it would be really great to focus on strategy consulting because that has both a really fantastic business and revenue-generating element to it.

Because youre pitching different projects and then youre going in there and youre working with senior executives at various companies and you have to get ramped up on really quickly to deliver strategic projects.

Drew Appelbaum: A lot of people write books and they write them for their former selves, and usually there was some adversity along the way, and they want to talk people through it who might find themselves in similar situations. Can you tell us about a few of the issues you ran into early in your career and maybe some of the lessons that were learned?

David Perry: Yeah, its funny you say that because after the project was completely done, I mean, in a way, I did feel like that. It felt like I wrote the book for that specific individual but once I really got down to it, I realized that once it was complete and I had read the whole thing, I realized that was a book that I really wish I had myself.

It dawned on me that I used to really look up to all these sales leaders and account executives that it seemed like they had everything figured out and I was like, how in the heck are they doing that?

You know, theyre never going to tell. Granted they might try to help a little bit, but they werent really going to share, they have no incentive to share in a really deep or profound way what theyre doing. As a matter of fact, theyre just worried about hitting their numbers and getting things done for themselves. I think thats actually what makes this book unique is that it was a huge risk for me to write this book while doing my job.

I dont know if there are any other individual contributors out there that have written a book like this. Usually, its mostly consultants, but thats really what I wanted to capture. I wanted to capture that notion of being able to just ask a top salesperson, someone that had a great year, How did you do it, what did it really take to get there?” Its funny how when you look at it on the surface, I see these people that theyre perennially, year after year, theyre successful.

They make it look so easy, but its really not easy at all. Theyre doing a lot and they have had a lot of lessons. So, I wanted to make sure I really captured that, and when I got feedback from a couple of people that had read it, they felt like they were sitting down and having a beer with me, and we were just talking about sales. So, that was a really huge compliment I thought.

Drew Appelbaum: Can sales success be achieved with different approaches and by different personality types? I ask because Ive seen many people fail early in their careers with maybe their first sales job because they dont know what to expect or they feel like they dont have the right personality type for it.

David Perry: I strongly believe that there are many, many different paths to success, thats actually something that I do talk about in the book, and I talk about how to build a dream team, and I give several examples of sales leaders that Ive worked with in the past. There really is no one specific personality type or even way to get things done.

What I really try to do in this book then is give people the general themes and commonality, but I strongly believe that no matter what your personality type is if you have a strong desire to be successful in sales, that you can do that. Part of what that comes down to is I think theres this preconceived notion that salespeople are all extroverts or theyre all really gregarious and outgoing. While that may or may not come through, as were going through the sales process, really the salespeople that are really successful are the ones that they yes. They can be outgoing or they can be direct and help to manage challenging situations, but they also are incredibly empathetic and able to quickly assess situations. So, those characteristics seem to me to be more along the lines with what you might normally see from introverts.

It is a real balance and I think that people that are more introverted tend to flex their extroverted side and the people that are extroverted, do the opposite.

Consensus Driven Sales

Drew Appelbaum: Has the salesperson mentality changed throughout the last few years?

David Perry: I think its changed in a lot of ways. There have been changes in technology that you can do your outreach and have that supplemented with technology to help automate a lot of the outreach. The process of tracking and providing insight into your pipeline with your management team is getting a lot more streamlined, theres a lot more data that you have on your buyers and how theyre interacting with your companys website or even with other websites. Theres a whole industry thats spawning there.

Theres been quite a change there. In terms of the actual process of selling, there are all sorts of methodologies that I think would become more and more ingrained.

Then the final piece is that the buyers have changed dramatically in that its much more of a team process, a lot of people are involved, procurement is a lot more powerful within the process, legal is a lot more power within the process.

I think gone are the days where theres just a single person thats like, Yes, I want to buy this.” Its much more consensus-driven and so that means that as a salesperson you have to be a consultant and you have to be an industry expert in order to win in todays marketplace.

Drew Appelbaum: So no more steak and cigar dinners with the one salesman?

David Perry: I mean Im all for those, you know, that is something that obviously we havent had the opportunity to do with the advent of COVID, but you can still do that. Thats still fun, you can still do the entertaining. I am not saying not to do that. I just think that alone is not going to win you the deal.

Drew Appelbaum: Now, the last chapter of your book is about closing potentially career-defining mega deals but you ask readers not to skip right to that section. So, I will ask you, what is so important about the early sections that set up the foundation for that last section?

David Perry: By the time you get to that last section, there are so many things and themes that I discussed that if you dont have a grounding in those other themes, you will just never get to that career-defining deal. There are just so many traps and pitfalls along the way to creating a really large transaction like that, and so again, this book will help you to navigate some of those things.

For example, if you dont have the right balance of deals that you are pursuing maybe you wont even get the chance to pursue a really large deal, or maybe you arent focused enough on risk in the right way and also, through the lens of proper frameworks, to give you the opportunity to identify and progress that deal. Or maybe you see a large deal, but you arent able to build the right credibility with your executives internally and externally and figure out the value that you can deliver, and translate into customers terms in a way that will allow the transaction to happen, and make it so that it is more of an inevitability than something you are really selling through.

So that is why I think it is so important to really go through the book as a whole. When I first wrote the book, I designed it from the standpoint that I wanted it to be really easy to read. I wanted someone to be able to–I mean granted we are not flying around these days–but the initial vision was, take off from New York and by the time you land in LA, you are done with the book and you feel like you have some new focus and new ability to tackle these larger deals.

Drew Appelbaum: Id like to dig in a little deeper to something you just mentioned. There are a lot of sales books out there that talk about these hardball methods of winning sales, but you prefer the easier, friendly, and more productive method of capturing what you call hidden value. Can you talk about the definition of hidden value as you are using it and maybe where someone can find it in deals?

David Perry: The notion of hidden value is that I think, to your initial point, and this is something that salespeople and also the companies you are working with can get trapped by really easily especially if it feels like procurement is throwing their weight around, it becomes a zero-sum game, and they say, You know, give me this and well give you that,” and sometimes it is a horse trade, or procurement or someone might make a really unreasonable request that seems impossible to get around.

So, if you find yourself in that type of situation, it can be a symptom–every once in a while there really is a blocker or some type of issue that you might not be able to get around. You cant win them all, but it is more likely a symptom that either you arent working with executives at a senior enough level, or to your point, you are not uncovering or capturing hidden value. So, the way that I talk about it in the book to find these things or to find that value is by thinking more broadly or as broadly as possible about what the problem is that you can solve for your customer.

I have a whole list of things that you can do in the book to actually figure out what different sources of value there are that you can also then translate into your customers language, so they can then take that back and use that in the internal business cases, so you can actually get the deal done, right? And of course, you can create a business case for them on occasion. But what I find is that if you are not able to really translate that value into the customers terms, it becomes very, very difficult to get the deal done.

So, Ill give you a specific example. Lets say you are trying to close a marketing automation deal and they already have another solution in there, and there are all these other projects that are going on and they are incredibly worried about disrupting other projects while replacing the existing marketing automation solution.

First of all, that is something that you might not know if youre not digging far enough. I mean that sounds pretty commonsensical, but youd be surprised, sometimes its difficult to uncover some of these other things that are going on back in the background of the customers mind, but if you do discover that it might be a huge source of value that doesnt cost you and it doesnt cost you or your company anything to see that.

That could be the difference between you winning and losing a deal because you can then position and structure the implementation of the technology, of the market automation solution, such that it doesnt interrupt or disrupt any of those other projects, and potentially can even reinforce them. So, you can work with the other partners or systems integrators that are working on those projects and make sure that youre completely dovetailing and integrating really well with them.

That is one of many, many examples of capturing hidden value for the customer that can help you get the deal done.

The Dark Side of Sales

Drew Appelbaum: Now even the most successful salesman eventually will have horrible meetings and get some really tough nos and go through some dark times. Can you talk to us about maybe the dark side of sales and what you do to potentially lift yourself out of it?

David Perry: Yeah, certainly. I mean so I call it the dark side of sales and you know I am actually not sure how people are going to interpret that if they think it is something unsavory, but that is not at all what it means. It is really about the internal aspects. Really what it is to me, the dark side of sales is dealing with uncertainty and those things that you just might not have expected that kind of nudge you into a dark place.

You know, in one regard its just an inability to properly react and deal with external stimuli and so I talk about that in the book. Early in my career, I would get thrown off by say, if there was some type of merger happening or reorganization, Id get just way too thrown out a whack by things like that. It really comes down to, like I said, expectation.

For people that are coming up in sales, in enterprise technology sales, or maybe just in the technology companies in general, I wanted to give them a road map of what to expect–you have to expect that there are going to be difficult times, there are going to be reorganizations, there are going to be a lot of change that needs to be dealt with. I try to give the reader ways to deal with that and get around it, and I give examples of things that have worked for me really well even though it might sound very simple on the surface, theyve made a huge difference.

Drew Appelbaum: Now, you created a lot of systems that you really fleshed out in the book. Are you worried about giving away your secret sauce? Have you just really opened up the competition here?

David Perry: Oh man, I mean that is something that I definitely thought about and I just made the decision that I dont really care about that. Because I think that there are all of these things that I put forth in the book, I think they can help a lot of people and make the process more enjoyable. I think that if teams are able to take advantage of what I put together here, I think it will be a better experience for everyone, including myself. So, you know my hope is that its going to be a win for all and not really anything at my expense.

Drew Appelbaum: You have small sections throughout the book on game-changers. Can you talk about what these are and how you chose these game-changers?

David Perry: It is really important that I had kernels or ways to summarize the core learnings that each of the chapters are about because again, I wanted this book to be consumed in multiple ways. You could read it in the evening instead of binging on Netflix and hopefully, you get a lot out of it. That is one way to read the book.

Then you have the game changers that summarize the key concepts. And I have those listed throughout, and also in the back of the book so you can help yourself remember all of the experience and lessons that you learned as you read the book. That is a big reason why I have that and also, I wanted it to be a way for the reader to be able to go back and refer to certain sections so that they could potentially use the book as a reference if needed. That was something that a few folks had actually mentioned that they liked about the book.

Drew Appelbaum: Yeah, those parts were definitely very helpful and David, writing a book especially like this one, which will help so many business professionals is no small feat. So, I want to say congratulations on publishing your book.

David Perry: Well thank you so much. Its been a great process.

Drew Appelbaum: Now if readers could take away only one thing from the book, what would you want it to be?

David Perry: That is going to be an individual experience and choice, so what I wanted it to be is that for each person that reads the book, I want them to take away one thing from the book that they are going to take action on the next time they go to work. I havent considered that and if that has a positive impact on that particular individual, I consider that a huge one.

Drew Appelbaum: Yeah, absolutely. David, this has been a pleasure and I am excited for people to check out the book. Everyone, the book is called Game of Sales and you can find it on Amazon. David besides checking out the book, where can people connect with you?

David Perry: You can connect with me on LinkedIn and also, you know I have a website for the book of course, so either, or.

Drew Appelbaum: Awesome. Well David, thank you so much for coming on the show today, and best of luck with your new book.

David Perry: Thanks Drew, I appreciate it.