In tech sales, every day is another chance to make a lasting impact. Your skillset and knowledge in an industry notorious for speed, makes you invaluable to customers, seeking an edge over their competition and challenges. You want that same edge but developing the dally practices to get you there can feel like a guessing game. 

In his new book, The Tech Sales Warrior, sales expert Chris Prangley reveals the methodology to crush quotas and achieve consistent results for the rest of your career. Chris’s process is a series of daily habits you can implement immediately to regain control, find clarity and feel empowered with your business.

In sales, it’s up to you to hold yourself accountable and the book will help you discover a new mindset and personal plan that will inspire you to abandon hope as a strategy and embark on a journey towards becoming a tech sales warrior.

Hey Listeners, my name is Drew Applebaum and I’m excited to be here today with Chris Prangley, author of The Tech Sales Warrior: Battle-Tested Strategies to Crush Quota. Chris, thank you for joining, welcome to The Author Hour Podcast.

Chris Prangley: Thanks, Drew, great to be here.

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

Chris Prangley: Yeah, totally. The past decade or so, I have actually been in the world of cybersecurity. I currently am a VP of Sales at a leading multibillion dollar cybersecurity company but my career didn’t always start that way. For about a decade before that, I devoted my life to acting and I have a lot of stories there, Drew. I know that’s not today’s topic but that’s where I started.

Really, before that, I always was intrigued by sales. As a youngster, I was often doing the lemonade stands or selling door-to-door or mowing lawns, always looking for a way to make money but it wasn’t until my adult life that I really began to love sales and really understand the power of it. 

The “ Will” and the “Why”

Drew Appelbaum: You’ve been in sales for over a decade. Why was now the time to write this book and share these stories? Is there a moment of inspiration out there for you? Did you just want a really large platform to let people know what you’ve discovered over this time?

Chris Prangley: It’s a great question. When I initially started out, my goal was never to sell a ton of books or to make a lot of money off of books, it was really to add value and give back. And I know that can sound like that could be a little cheesy or something like that, but it really is that. It all started when I morphed from being an enterprise rep into a manager. In some ways, I was kind of forced into that. 

I loved being an enterprise rep, I loved the money, I loved the cash, I loved the value, I loved the independence. But when I became a manager, it really shifted my sales career and the fact that I realize how much I could share what I’ve learned and also see the impact of sharing what I’ve learned, and putting and instilling habits in those that I coach and seeing their lives change. And that’s really what this book is all about, it was written mainly with one person in mind and that reps probably know who they are once they read it, and just witnessing their life change because of the habits that are shared in this book. 

It’s powerful, it was an amazing moment in my life and to this day, I still have these moments with dozens and dozens of new reps that I coach and work with.

Drew Appelbaum: Now, there’s a lot of experience, of your experiences, in the book itself but when you went to actually write the book itself, even though you’ve lived through these moments, did you have any learnings or come to some major breakthroughs just reflecting on the past or putting together processes and methods?

Chris Prangley: I think if I was going to have a major breakthrough, just how clear, simple the road to success is in terms of instilling these types of habits to lead you to where you want to go. But often times in sales because there’s a piece of it that’s, let’s say, out of our hands, there’s a small piece that’s outside of our hands, I think it’s natural to want to complicate things or not do certain things because you’re hoping that success may be found in an easier way.  

But really, when going through this, it’s all laid out there and in my work with many, many reps as well as my working with a lot of top sales leaders, just the simple path in following that day in, day out, really set you leagues above the rest of your competition as well as your peers. Because it is, at the end of the day, it is tough work, although the plan to do it is pretty simple.

Drew Appelbaum: You sort of mentioned it before but when you started writing the book, in your mind, who exactly were you writing this book for? Is this for people who are new in the sales world, is this for experienced sales folks? Is this for training managers?

Chris Prangley: Yeah, that’s a good point. Initially, the book was for newer enterprise sales reps, specifically within the tech industry. If we really want to get granular with the software, but it really applies to folks in hardware as well, but folks that are newer to the game and they want to become top leaders, top sales leaders. It also could appeal to folks that want to become enterprise field reps and currently, maybe they’re an inside rep or TDR, BDR and that’s their ultimate goal, this would help them as well. 

For the regional manager, this is going to help understand the habits or the path of successful sales leaders so they can do a measure on their own reps. Are they following in this track, these types of methods? Are my reps going to achieve this level of success? Then really, for myself and for many reps that I know that are consistent quota crushers or what I would call “tech sales warriors”, is the constant need or curiosity to get better in your game, day-in, day-out, regardless of how much success you’ve had, you can always be learning. This book would also appeal to them. You know, when I first set out, it was for that new rep, they want to be a leader and they want to know how they could do it themselves.

Drew Appelbaum: Well, speaking of the early days, help us set the stage and maybe talk to us a little bit about your early days in tech sales and how you’re doing and what those early lessons were?

Chris Prangley: Even before tech sales, there was a couple of sales roles that I had where number one, in prospecting, I absolutely hated it. I didn’t understand this concept of just cold calling, cold calling, cold calling, just dialing people. Why would they ever want to talk to me, why am I wasting my time, why am I wasting theirs? 

Then finally, when I got into the tech sales world, a similar type of mindset, because I didn’t quite understand the concept of finding a “why”, or the concept of value delivery and because of that, I struggled a little bit with the consistency of day-in, day-out, what I’m supposed to be doing. 

When I first started, my first year in the game, I missed quota by, I think it was about 3%. For some folks, that may seem like nothing. For me, it was devastating because I saw a lot of my peers on stage, a lot of my mentors, and of course, in the sales game sometimes you get nudged a little bit if you miss and that of course occurred.

It didn’t start out so great in the sense of, I didn’t hit quota. In sales, we know that really is everything. From there, that’s where I dove in and I got my mentors and I went out and I sought folks that could help me get to the top of my game.

Drew Appelbaum: What did they say? That you’re not really trying unless you failed a few times?

Chris Prangley: Definitely. Failure’s definitely the key to understanding what works, what didn’t and where to go next. Sara Blakely, I think she says something like when she was growing up, her dad used to say at the dinner table, “What did you fail at today?” I just love that. You’re putting yourself out there, you’re trying to learn, trying to grow.

Drew Appelbaum: Now, digging into tech sales, how much of it really is strategy and method versus really the headspace and determination that you have inside of you to really lead you to hit those sales goals?

Chris Prangley: Well, I think it’s a bit of both. The title of the book, The Tech Sales Warrior, you definitely have to have that mentality day-in and out and I talk a little bit in the book about, hey, if you start in the game, initially, you start talking about, “Hey, I want to just make a lot of money.” That may help you initially but you’re going to eventually burn out.

It’s not just about that and we can talk way more about that topic on another call but you definitely have to have your mind right. You have to understand your “why” as to why you’re battling every single day. When you’re going to get involved with enterprise, accounts, leading global firms, there’s a lot of strategy that is involved in understanding that business’s needs, that business’s challenges and pains and how your solution aligns to them, right?

Whether it’s today, tomorrow, in the future and so on. I believe both are extremely important, I don’t think you can have one without the other, I don’t think you’re going to be successful for the long haul if you just will yourself through. That definitely will not be met with success but a combination of those are very important. 

Drew Appelbaum: You mentioned that the book is going to bust some of the myths surrounding sales. Do you want to mention a few of those myths and what inside the book really bust them, if you will?

Chris Prangley: Yes. The first one really, around sales being all about money. We talk about the book when we’re highlighting it. Usually, new reps, when they come at the game — I don’t want to generalize because it’s not everyone, but many new reps when they come in the game, it’s all about the money, the flash and the cash. We, in this day, we got it, social media and instant gratification.

That’s fine and I understand it, especially when you’re coming out of student loans. I had quite a few of those that I had to tackle as well but this myth of sales is all about money, you’ll realize with the metrics that you need to achieve, the stress that’s involved and the day-in, day-out kind of challenges that you’re going to face, it’s really not a process or a mentality of success.

Although you may enjoy money and enjoy what money may bring you, if that is what’s driving you today, it likely will not lead to long-term success. From the folks that I’ve worked with and seen, I’ve worked with dozens and dozens of folks. That would be the first one and what I would recommend to someone for that is finding your “why.”

There’s is a lot of books out there that talk about finding your “why”. When I first heard the concept it was with Tony Robbins, and I know Simon Sinek has talked a little bit about it as well. When you can align that “why”, why you’re doing things with your day-to-day, it’s so much stronger, you really stand out. 

The other myth that we could talk about today is really just this myth of sales being the old school used car salesman, trying to trick people to get a deal done. That’s the furthest thing from what I see and what I see out of sales leaders that are successful. It really is about understanding your client’s pain, their business challenge, something that’s keeping them up at night and figuring out a solution for them, solving a massive problem. And as a natural result of that, you can make a lot of money, of course. 

It really is cool, you know? I’ve grown to love sales. If you asked me this maybe a decade ago or 15 years ago, I’d say, “Oh gosh, sales? No way, not interested at all.” In seeing the impact of what you can do in your day-to-day, it’s so cool, it’s awesome.

Re-integrating Humanness Into Sales

Drew Appelbaum: I like that in the book you actually speak about being your own brand and that’s your personal brand within your company brand. I’d love for you to dig into that a little bit more. What exactly does that mean?

Chris Prangley: Yeah, it’s one of the things too that you have complete control over. There’s a lot to kind of review in that concept of being your own brand but some of the basics like, let’s just take the face value. How you dress, how you show up on time, how you communicate with your peers both in the company and outside of the company, the work that you deliver, how you prepare for meetings. 

Let’s just talk about a very basic thing. When you show up to your first meeting with your clients, do you know anything about them? Do you study up on the actual person that you’re meeting with, about what their firm is going through? Or, do you just kind of run through it like it’s any other meeting and you know, go on with your life?

A lot of what I talk about is holding yourself to a higher standard and in doing so, you’ve really stand out from the crowd of other sellers. It kind of reminds me a little bit of what’s going on, I don’t know if you’ve seen this on LinkedIn but it seems like there’s quite a lot of sales-bashing lately. I see a lot of executives talk about, “Hey, these sales reps are terrible” or “I can’t stand these sales reps, always calling me or doing these tactics.”

Well, a lot of what happens with these types of sellers is they’re treating these targets or prospects like any other person. There’s no humanness to it, there’s no — you haven’t done any research, you haven’t understood what this person needs and so you’re just assuming like the human on the other end is a robot. And as a result, you’re going to get a robot response, or someone’s going to put you on blast on LinkedIn.

It’s not falling into this category of generalization, stepping up and saying, “Hey, I can make a difference in this world and this is how.” And then, if we bring it back — I know I’m a little all over the place here but — if we bring it back to the basics of how you dress and whatnot, you don’t always have to wear a suit. I usually always wear suits when I’m out and about, it’s just my thing.

I know many successful sellers who wear more casual gear and that is their brand. That’s who they are, take it or leave it, this is who they are, but they’re all about solving their customer problems and that’s what they care about. And their customers don’t care. So you can create what’s unique for you. 

I think you also have to be cognizant of the firm that you work for and the firms that you are selling to, right? If you’re going into a law firm or a think tank, you’re probably going to be a little more conservative in the dress but there’s so many different options to make you as an individual stand out and you were completely in control of this. I hope that helps cover a couple of the points, Drew.

Drew Appelbaum: Yeah, for sure. Actually, I want to just add on to that a little bit and ask, what has changed with working from home now? I think a lot of bigger firms always did online meetings, always did calls via phone so there wasn’t — it wasn’t an exclusively face-to-face but now that most sales or a lot of sales are done virtually, are there any — have strategies changed? Have any of your methods changed at all in the last few years?

Chris Prangley: Yeah, while the world did change — and I can’t believe, two, going on to three years, that’s just a lot to think about it — the good news is, for tech sales, for many folks probably using webinars, whether at Zoom or Cisco’s product or whoever’s product, there’s always been that element to be able to use technology to connect. But I think, over the past couple of years, we’ve seen that come to the forefront, you definitely lose a bit there, right? 

Some firms, they’ve always sold through the phone or online but many enterprise sellers have had in-field selling as a part of their day-to-day, whether it’s lunches, dinners, events, et cetera.  So it has changed. I think we’re rounding the bend here and we’re going to have a bit more in-person. I’ve actually been traveling a bit more but we’ll see, you know. You never know, it could be another variant out there.

I think if I’m going to recommend anything — you know, it’s tough. I’ll just call out like for instance, Zoom, right? If you’re using Zoom, you can be worn down if you’re on it all the time, all day long on the video. Number one, I would check in with yourself. Are you feeling a little sluggish, are you feeling a little slow, do you not feel the video? It’s kind of what we talk about in the book with this idea of checking in on how you’re feeling so that you’re prepared for your meetings.

I would say, the majority of the time, try to use the video, try to connect with that other person and they’re going to — your customer or your target will likely look to you if you’re not using video. They may not want to do it or in some cases I’ve seen, where they start with it and the sales rep doesn’t and they feel a bit offended. “Hey, I got my video on. Why don’t you have yours on?” 

What I’m getting at is number one, check-in with yourself, how you feel. Because, it can be exhausting to have a video on all day and maybe you don’t need it for all your meetings, so save it for the very valuable ones if you’re running into that challenge. Make sure that when you do turn on your video that you’re prepared. I would recommend dressing, once again, to your brand and what works for your customers and your firm. 

Be aware of your surroundings, sometimes folks may dress up like they’re wearing pajamas or the background, there’s stuff going on back there, right? You got to be aware of these things, especially when you’re trying to be a professional in this scenario.

For all the parents out there, oh my gosh, you’re all angels. What I’ve seen over the past couple of years is just remarkable with how folks have had to manage time — and I don’t have a lot more to share on it, other than even though a lot of my teams, we’ve switched to work in a digital world for certain periods of COVID, we’ve still seen a lot of success.

I think what rings true through all of this is that human approach, trying to connect on a human level, whether it’s through the video or through the phone, you don’t always have to dress up or things like that but also, I would just caution against saying, “Okay, the fact that I don’t have to dress up, I’m also not going to show up in pajamas, right?” Yeah, I’m trying to think of anything else, Drew.

Drew Appelbaum: You could still rock the pajamas in the bottom, you know?

Chris Prangley: Yeah, that’s true, you know there’s been a lot of people that rocked the shorts, jeans, whatever. I may be one of those folks. Yeah, of course.

Drew Appelbaum: All right. Chris, for everyone who has been listening this time and they’re saying, “Get to the good stuff.” When I have a sale on the hook, tell me, first of all, what are some common ways that sales folks do struggle and how would you suggest that they, one, get through it to make sure the sale is there and that the sale is priced right for everyone?

Chris Prangley: That’s good. There’s a lot of sales methodologies out there, right? You could have a hat and pull out 20 different sales methodologies and there’s great things to learn from all of them. But I think if you’re to boil it down, this concept of understanding, number one, what year customer or your prospect’s pain is. It’s very important. If you don’t understand that, we don’t really have a deal yet, you’re just kind of hoping for a deal. 

Two, who the power is, meaning, who actually has to sign the PO and be involved in this actual deal. Three, the timing of it, when are they planning to move forward and why is there an upcoming event, why is this date different, is there some sort of regulation or is there a board mandate, something like that. Four, just the budget range as you mentioned, understanding that we’re on the same page. Is this thing between $100,000, $300,000 per year? What is the actual cost that we’re tracking for? 

I think understanding these four basic things, and it almost sounds like BANT if you ask me, but if you look for these four basic things, it can really help you in understanding the gaps in your deal and what you need to find out, right? That’s where I would start and then from there, we can dive into the details. 

We can get very granular as to what has occurred, what hasn’t occurred and where are the gaps and all the stuff. But those four things, which surprisingly, these can be a struggle for many folks to get to. The earlier you get to these answers in the deal, the quicker you and your sales engineer can work devising a plan to achieve them and ask for the PO.

Drew Appelbaum: Well, Chris, you know, we just touched on the surface of the book here, you offer so many resources in it in the book and so many strategies in there as well but I just want to say that writing this book, just to help folks understand how to become more successful in their craft is no small feat. So, congratulations on having your book published.

Chris Prangley: Thank you, Drew, I’m so pumped. Let me know, you know, for anyone out there if you read it, if you love it, if you don’t like it, if parts helped you, let me know. You can either find me on LinkedIn or if you go to techsaleswarrior.com or chrisprangley.com, you’ll be able to find me there but I’m pumped. You know, I really believe everyone can crush quota, and do it not just once but every single year. And I hope this book helps you like it’s helped many people.

Drew Appelbaum: Well, Chris, this has been a pleasure and I’m really excited for people to check out the book. Everyone, the book is called, The Tech Sales Warrior, and you could find it on Amazon. Chris, you just gave out a few ways of how people can contact you, what is your number one preferred method if someone wants to reach you right now?

Chris Prangley: LinkedIn’s probably the best way. If you find me on LinkedIn, I’ll be there.

Drew Appelbaum: Awesome. Chris, thank you so much for giving us some of your time today and best of luck with hour new book.

Chris Prangley: Thanks, Drew.