❤️ People buy from people
Bradley talks through an inbound lead that turned into the largest transaction in company history.
Featuring Bradley reverting to a closing role as a Sales VP, a death in the family mid-deal & his team rallying together to bring it across the finish line as a result.
Balancing sales performance & mental health is at the forefront of this conversation.
We need to talk about it as revenue professionals more, but this is a start.
Bradley Paster started his sales journey as a Regional Sales Engineer.
Made the jump to an AE role at Dell for 5 years, then promoted to a Director role.
Since then, He’s gone on to various VP & SVP titles and is currently the CRO at Guardsquare.
What are you selling?
- Governance compliance software
Where did the prospect come from?
- An inbound lead that came in
- An enterprise insurance company in New England area
- Efforts were focused on research since the inbound didn't contain much information.
Barriers to Overcome
- A death in the mid-deal changed Bradley’s entire focus & had to rely on his team.
- End of the quarter deadline provided a challenge to close on time.
- Decision Maker: CEO
- Users: Government liaison office
- 9 month sales cycle
Note: timestamps correlate with the full conversation
Sales leadership: More pressure to close a deal as a sales leader? (4:01)
Team selling: Lean on your team where times are toughest (18:40)
Barriers: Sales & mental health. People buy from people. (23:28)
3 Tips for Account Executives
1. Build a process each step of the way & stick to it.
It’s the best way to stay on track & consistently perform.
2. Engage your internal teams early & often. Both your team & the prospects.
It’s way to hard to sell alone.
3. Don't be an ass. Empathy over everything in sales.
Doesn’t cost you anything to be understanding. You might need the same treatment someday
Watch the full conversation
Welcome back to How I Deal, where we discuss past closed won and lost deals, how they played out that way, and provide sales tips that account executives and really any sales pro can use in their deals today. My name is Taylor Dahlem, full cycle account executive, turned content guy, and I'm joined, as always, by my co-host, Junior Latte, the sales guy here at Pickle. June, how are we doing, man?
It's episode sixteen. I've got something a little bit unique today. So for our listeners, we've had deal cycles where we've talked about Mailshake, Adobe, Quota, Path, Market Two, and others. If there's a specific company or product vertical that you would like to hear a deal from, reach out and let me know. Then I will in turn do some research, reach out to some AES from said companies and products, and we'll get them on the podcast. So essentially we're putting the power in your hands, use it responsibly. But I think it should be pretty fun.
Yeah, I think that's a fantastic idea. In a way, we can get a lot of interesting folks to talk about their life and sales and deals they've worked in the past. So excited to see where that goes. But while we're here, a quick refresher. If you haven't listened to us before, or maybe you haven't listened in a while, each conversation we want to chat through a single pass deal. We want to keep all names and places fictionalized. Of course, that allows us to really dive deep from the first time a prospect was either spotted in the CRM or on a list, or in this case, coming in inbound, and then all the way to getting that dotted line signed, that DocuSign completed. Really, wherever your deals close and implementation starts.
Our guest today is Bradley Pastor. He started his sales journey as a regional sales engineer, made the jump to account executive for five years, became a director for four years, has spent the past nine years in various VP and SVP roles, and is currently the CRO at Guardsquare. More than anything, this is a reflection of what five years as an account executive can do for you. So Bradley, it's really great to have you tell us about your role today and what problems Guard Square solves.
Sure. Thank you both. Great to be on the podcast. Enjoy listening to it as well. So, as indicated, I'm the Chief Revenue Officer at Square. We focus on mobile app security. So we primarily do three things we help organizations test, protect and monitor their mobile apps, whether they are on the Android or iOS platform.
Bradley, what deal are you walking us through today?
Sure. For me, it's a little bit of a trick down memory lane. There is a deal that goes back almost four years ago and I was VP of Sales at a company by the name of RSAM that was acquired by ACL and then Galvanized and then became diligent, and they focused in the governance risk compliance space. And we're working at the time, I had an open territory, and we're looking to hire some folks into that and constantly interviewing, yet the deal still needed to be worked inside that territory. And we had an inbound lead that came in, and I took a lot of the inbound leads because I wanted to see, hey, is there something here? Is it real? Is it not? And we had an inbound lead for a large insurance company in sort of what I would call upstate or northeast part of New England area.
So I got a question, Bradley. As a VP of sales, if you're working a territory yourself, is there like, more pressure to perform? I guess maybe better is not the right term, but produced because you are working a territory yourself.
There is and there's pressure, multiple areas, right. So there's the existing reps who feel like you're taking a deal away from them. Right. There is the potential for reps coming in. So if I hired someone in that territory at the time, the idea and the intent was to transition that over to them. And then there's also, as you indicated, I mean, you're the DPS sales. In theory, you should be able to go and do everything or the perception right, is that you should be able to do everything better than someone else. So if you take the deal and you lose it, you have the risk of everyone else saying, gosh, you should have handed off to sue or to Tom or whoever because they could have closed the deal, right. You're an operations person. You're the sales people. So certainly a lot of pressure. But at the end of the day, regardless of what role you are, if you're a seller, the obligation is that you have to close the deals for the company. And this was an opportunity to step in, help cover a patch that was open. I believe, at the time, the intent was there, right. By everyone in terms of balancing roles, territory, potentially people coming in and helping focus on revenue generation for the company.
I think that's awesome. Able to just step in and sell as a VP of sales, although you're like, hey, I'm not taking this from anyone. I'm not stepping on toes here. Open territory, you're working it as best you can, which is really cool. So this deal is kind of wild because at this point, you've got a lot of years of selling experience. You're no longer an account executive. You're past the director stages even. And so a company comes inbound, right. That's how you became aware about them. Tell us a little bit about that between yourself, marketing and the research that you conducted before this meeting actually took place.
Sure, absolutely. So there's a perception often that you get an inbound lead, and the inbound lead has all this great information associated and you just sit back and crack open salesforce wherever you get a problem. And you're like, wow, everything's here. The reality is, a lot of times inbounds have a name, maybe a title, email address, hopefully work email address, hopefully telephone number. And when I go back in sort of time here, four years or so ago, this was pre-covid. So people were in offices, and even if you didn't have a phone number, you could probably call the main number and get to the phone number. I know now that's more challenging. So you get an inbound lead. And this particular account, while the use case in theory was inside of our ideal sort of customer profile, the actual account in terms of as an insurance company wasn't inside of our ICP. So really, when it came in, it didn't register to anyone myself, for marketing that this deal would eventually be the largest single transaction deal in the history of the company. So I had to go and start doing discovery and call them up and say, hey, you reached out. Why?
I'd say rather, that kind of leads us into that next step too. And we were talking about this a little bit. As he mentioned, most inbound leads don't come with a ton of clear context in the sense that, like you said, it's very loose information. As a marketing guy, I'm always excited for inbounds, but as a salesperson too, on my other hat, there's always a grain of salt to be had. But a lot of deals can be lost in that discovery process like you were just talking about, because if you sat back, relaxed, thought they were just ready to buy, you were just an order taker at that point, or they had no idea what this technology was or what this product or service was at all, they could be on either end of the spectrum. And now it's your job to figure that out and discovery. So you may be dive in a little bit more on what that looked like for that, digging for pain and really understanding where they were coming from and where they were at. What did that look like for you and what did you learn? Absolutely.
So I'm a huge believer that deals die in discovery. And to expand upon that a little bit more, I believe discovery continues all the way through when you close the deal. And then actually, if you're in a product-like growth company or a landing expand model, discovery continues beyond closing. When you have enablement, you think about growth in it. But that's a conversation for another podcast, potentially, you can't sleep on inbound. You don't know when the inbound comes in, how valuable it is, how not valuable it is. And the notion that reps will look at an inbound and immediately pass judgment without engaging is just egregious. And the top performing reps in the company I've worked for and certainly when I was a top performing rep, I've been on Presidents Club and One Rolexes and done all that stuff. So I certainly have a good pedigree in the background there as well. You got to call everyone that comes in, and again, you don't know. And there's a multitude of different formulas and processes and frameworks. I like Medic, so there's bunch of different variations of that. Force Management is a newer iteration of Medic from the people that develop Medic. There's MEDPIC, there's MEDDIC, which replaces metric with value for your listeners who are not familiar with MEDDIC. It's basically a mnemonic for metric, meaning, how does your prospect measure the value that you're bringing? That could be time, it could be money, it could be people, it could be meeting a regulatory requirement. The easy economic buyer should be pretty obvious, but a lot of times folks make the mistake of thinking the person they're talking to is the economic buyer. What's the decision criteria, what's the decision process, what's the pain? And then who's the champion? And inside all those stages, there's lots of books written about how to flush out all these things. Predominantly in my mind, in discovery, you want to focus on what's the metric, what's the pain they're looking for, which is different than pain. Pain is we need to solve this. The metric is how would you measure solving that? So I want to understand what's the metric, what's the criteria, and what's the process? So a different way of thinking about it is the who, what wine when I think if you cover, who cares about this, what are you trying to solve? When do you want to solve it, and why do you want to solve it? You really covered eighty percent more discovery than most reps will ever do.
I loved all of that. I specifically wrote down one piece that you said where you said, how would you measure solving that? Pretty powerful statement as you're going through most of that process and trying to really figure out what the pain is, what problems they are, but figuring out, like, towards the end of things, okay, maybe this is the problem. How are you going to measure solving that problem? Man great input. Thanks for wrapping up. Like what? MEDDIC is MEDPIC? There's all these things, you can Google them, there's courses, all sorts of stuff. But at this point, you've unearthed some pain. You've verified your hypothesis about what this is. You didn't sleep on the inbound aspect, so you've put cards on the table. It's time to demo something, right? Time to take it past discovery. So what was the demo process like? How did you personalize it and keep it focused?
Sure. So a little bit of greater context here. This was, I think I said four and a half years ago, and to give people some frame of reference back then, it sounds like it was a long time ago. People would actually get on planes and go visit customers or drive and visit customers and prospects. And now the notion is just hop on a zoom or whatever. So we said, we'll come out and visit you. And they go, wow, okay, you'll come to the middle of nowhere and visit us, which we did. And we met with the champion, got a better understanding of what they're looking for, provided what I call a functional demo. Not necessarily this is what we would do for you, but this is what the platform will do. So we really try to focus on two ways of doing the demo. The first demo is, I don't know your business, but I know what we can do. Let me give you a sense of what we can do. Then you hope, and if you execute well, that the demo touches enough high-level points that you're, championing will say, oh, okay, now we can sign an NDA. We can give you content, we can give you schema, we can give you processes, whatever it is that's important to you that you can integrate into the demo. Now, in this instance, we had to give our champion another demo to demonstrate, yes, we understand the marketplace and the technology. Okay. We understand a little bit more with you. And then if you, the Champion, feel comfortable with what we're able to demonstrate, will you then give us access to everyone else? So while we were going through the them, part of what we're also doing is we're trying to understand who else is part of the process. Why is this important? Who are the other people that are involved? And I believe having a demonstration that pulls in their content, their data, their metrics, their information, and then understanding why that is important to people is a great way to progress the deal. There's a lot of different ways to do it. But you can imagine if you're working with Tom and Sue's boss and he said, this is important to sue, and you say, Great, can we get her feedback as part of that? It helps move those things along. I'm obviously oversimplifying it, but that's basically what we did. We went out with them, demonstrated our capability, demonstrate our willingness to listen. And then at that point, we said, how do we progress from these two sets of demos to move forward? Right.
And I love the personalized one-on-one demo with the champion, because the champion can really help you expose areas of your services, areas of your platform, where they know could have high impact. And it's just like building that relationship even stronger with somebody on their inside that can help you navigate everybody else, which is really great. And after that demo, now you've got broader buy in to do a bigger demo, which you're trying to do in person at this point. Right?
Right. So the overall sales cycle was about nine months. So the way, given our conversation, it sounds like this was over a couple of weeks. It was pretty long. We just flew out there, had lunch. It was great. Roughly nine months sales cycle. Initially, I was talking with our Champion once or twice every other week, and then as the months progressed, we were engaging to ultimately, we're doing three or four calls a week. He and I, making sure we're aligned, wound up. That part of it was a competitive displacement, and there was time pressure that one of the platforms they were using had a renewal date so they could continue going with the other vendor. They could use some of that budget to cover what we were doing and all these things. We had no idea initially what we engaged, but this comes through really empathetic listening, understanding what the needs are, understanding why they're important for people. And I really think you only get there by demonstrating trust and competency through the process. Right. Ultimately, people buy from people. So you want to establish trust early on with your Champion. And look, the reality is you may leave your Champion and find another Champion, but you want to be able to maintain those relationships in the process. And ultimately, what we found out was there was this completely wacky edge use case that had to do with members of their board and conflict tracking. Meaning you're a board member, but you're also on the board of another company, and you need to do disclosure to make sure those boards don't compete. And it was something that we, the company, had nothing to do with. Yet our framework was flexible enough that during the course of the conversation, our Champion said, hey, could you do this? I don't know. Right. But the answer is always, sure, let me find out more. And my se is rolling his eyes. But again, I was a former se. I'm like, don't roll your eyes to me. I know how to do this. We went and we built it out, and it was completely random. It was the edge use case that sold it. Because if you think back to Medic and this is why I like frameworks, if you go through a checklist, it was, who is the economic buyer and then who is part of the decision process? So ultimately, the people at the senior finance level and the people the senior executive level felt comfortable signing off on it. Not because, ironically enough, not because we solved the core use case they were looking for, but we solved this esoteric edge use case that benefited those senior executives. Right.
I think the edge use case in general we talked about this last week, Junior, but it's this concept of not always are you hitting a home run out of the park or solving a huge, massive problem. A lot of times, what closes deals is either risk aversion, like, hey, are you just keeping me safer, or are you addressing a very specific need or a very specific small niche that maybe nobody else is thinking about answering or filling in? A lot of that can be a lot more powerful than just trying to solve every one of their problems or shoot for the moon, so to speak. But I think this is a great example. In that case, I guess we could move to this next concept. But the thought is you've had the discovery, you've now had the personalized demo, and obviously this concept of the edge use case came up. You're solving that probably better than anybody else, but as any deal progresses, there's always going to be barriers that you have to overcome, whether they're on the company side or on your side internally. Walk us through maybe a couple of those major barriers and maybe how you overcame them.
I think maybe three things that all happened roughly around the same time. Which was we finally got to the point where we had done the individual meetings with stakeholders and I pushed them for what I call like a demo day or lunch and learn however you want to describe it. But basically a workshop where we're going to go through all the use cases. Bring in the various stakeholders. Show up at tons of collateral and socks and pens and all that fun stuff. And really just do that whole workshop day. It's really hard on the vendor ourselves, a little bit easier on the prospect because they just roll in for an hour. So that was scheduled, that was set up. That was our final sort of competitive walk through the night before I wind up at Mass General Hospital in Boston, because my mother-in-law's husband at the time had a heart attack and medical complications, and he died the night before we were supposed to fly out. So I called my CRO who lived in Tampa and said, I need you to go to this thing. And he's like, all right, I don't know how I'll get there. We'll figure it out. I called, I texted our champion at nine o'clock at night or so and said, hey, here's what's going on. And he's like, hey, if you need to cancel and reschedule, it's totally fine. I said I don't know. But I'm gone. I'm unavailable. I'm just letting you know. I'll connect with our CRO, we'll see what we can do. And we didn't really touch on this as part of the conversation here. I did a little bit with trust with the prospect, but I felt comfortable sharing and being vulnerable with the prospect because at this point, I think we're maybe eight months, seven and a half months into the process. I know him pretty well, knew where he went on Hymen. I wouldn't say we were work friends, but we transcended just sort of that general initial level. And I'd also kept my team completely up to date through the entire process. So look, I'm the VP of Sales. It would have been really easy for me not to keep salesforce up to date and not keep the sales engine team up to date, not to keep my CRM updated. But everything was locked in salesforce. Everyone was currently up to date. I informed all the stakeholders inside my company. So when these events happened, I wouldn't say it was easy. And I'm not saying the balance between work and personal, and certainly someone dies. For me, allowing me to hand off work allowed me to focus on the personal aspects of it. And everyone needs to manage those things differently for who they are. But for me, I was able to hand it off to my team and say, just go and do. Because I had kept them current, because I kept my information accurate, because I kept them engaged. Because you could go through and look through salesforce and see weekly notes to my champion, to the stakeholders saying, hey, thank you for the time. This is what we covered. Here's the next steps, here's what we're looking to do. So things happen all the time. Sometimes good, sometimes bad. And hopefully when the good things happen, you can celebrate when the bad things happen, which is more often than not if you're working in a team-based motion and you have everyone involved and you're working with your boss, in this case, my boss is the CRO, and you're keeping people involved in current and up to date. When these things happen, you can either get coaching, right? So if you're a junior rep or anyone, look, we all need coaching. You can get the coaching. If your company uses Pickle or something, do your calls in Pickle so that information is there. All the information is in salesforce. So I didn't have to say to my CRO, oh, let me write this all up while my wife and mother-in-law are morning. I was just like, I'll talk to you later, right? Here's the guy's contact information, which quite frankly didn't, because all that was in there. He could just look inside salesforce and all that information was there. Handoff was seamless. And look, our customer, hate to be unkind, they didn't really care that my mother-in-law's husband passed away, right? They had twelve people scheduled per day coming in and out, but they were able to keep their emotion going and keep it rolling. And aside from my champion, I didn't tell anyone over on that business side what happened. They found out later on, but we were able to keep rolling because of that.
Sounds like you did a fantastic job, like documenting everything along the way, keeping people in the loop, as you mentioned. And the people coming to this meeting, it's no longer like base level, it's like these are high level, high impact decision making people coming to this meeting. So it certainly seemed like, hey, the meeting must go on. Bradley, you've managed a lot of people over the past twenty years. Maybe let's step away from the deal aspect and talk on the personal side because I'm sure people on your teams have gone through things. You've helped people walk through that. How do you mentally go through something like that and then knowing you have to come back to the sales game at some point, you got to come back and start selling and do your job again? How do you go through that process? I know we're not therapists, but just from your perspective, maybe give us some insights there.
I sort of say I learned the hard way. My wife and I had some challenges a long time ago with pregnancy and babies and stuff like that. And I came into work and my boss at the time, Lincoln, who's the chief marketing officer at Aqua, said to me, she pulled me into the office and she was like, what's with you? Right? Like, you're not engaged, you're not doing everything. And I remember sort of opening up and crying and explaining to what's going on. And she said to me, you need to share, you need to engage people. And if you don't do that, then it's really challenging. But if you share, you'll find that people will support you and be engaged and even going way back. My mother passed away about twenty-six years ago, and I had the opposite at the company I was working for where my boss at the time could care less, that my mother died when I was twenty-five years old and there were some empathetic people inside the company. So what I've learned, both the good and the bad over time, is that the people you are selling to are human beings. The people you're working with are human beings, and everyone goes through struggles and challenges. And yes, we have an obligation and responsibility for the company, and I have a responsibility for the company I have here, but we also have responsibility for each other. And if you work and operate in an open and ethical and honest way and you have people engaged and you meet and hopefully exceed the expectations of you, then it becomes very easy, I believe, to have that support and have that openness. Right. Where I think people go off the rails is you hear this from Salespeople. Marketing is not giving the leads, or my boss is riding me on filling out Salesforce, or I don't want to use Pickle because it's Big Brother. And what they realize is there's so many aspects of that. I mean, we're in sales, we have to be measured. You are measured in terms of metrics, but there's also other aspect of if you take a pause and step back. I'm going to use Pickle so I can get better coaching. I'm going to get Sales to use Salesforce so I have better visibility with my team. I'm going to share what's going on so that when I have a bad day, people understand the context of what's the bad day. Not that I'm just being a jerk to other people. And if you do that, I believe what you find out is you have that balance I expect and hold and try to hold my team accountable. They should hold me accountable. The executive team and the board should hold me accountable as well. But I'll be very frank with them, or I'll say, hey, I have this thing coming up, whatever it is, but here's what I'm doing to prepare around it, right? So in the instance of my mother-in-law's husband passing away, I didn't have this great package around here's, everything, and let me take an hour and let's put everyone together on the team. But I was able to say, here it all is, because everything else was taken care of. And then I didn't have to worry about work, right, and making commissions and paying bills. Am I going to lose my job because my shit was together? So my takeaway for people would be, if you think about it in terms of three sort of primary things, you should have a process and stick to it. Make sure everyone's aligned with that. I would engage your internal team and internal team is both your company and the internal team you're selling to early and often. And also, don't be single-threaded, so don't be single-threaded just with the people inside your company. If you're working presales, you're working with SDRs, you're working with marketing, make sure to the extent possible, right, that people are engaged. So an example that is, you reviewed the Pickle call with your SDR prior to doing discovery. You review those calls and notes with your sales engineer before you get on with them. So you get access to all those people. And then the two final takeaways I would put in there is like, don't be an ass. Right? I think you'll get really far professionally just if you take that to heart, not being asked, not be jerk to everyone. And the other aspect of it is be empathetic and understand that both your prospects and the people you work with and yourself, you're going through a lot of things. So if you manage to pull basically those top three and those two other elements together, I think you'll build a pretty satisfying and successful career and you wind up surrounding yourself with people that want to be working with you as well.
Bradley, I don't think we could have wrapped this up any better than you just did for us now. It was really great chatting with you. A VP of Sales who is actively selling now, a CRO who is not afraid to jump in and help. Thanks for joining the How Ideal podcast.
Thank you. Thank you both. I really enjoy it.
Yes, thanks, Bradley. Super, super insightful episode. I always love talking with somebody that started at the humble beginnings, like we're at as, account executives and junior sellers all the way to where you've grown in your career. So great insight and as always, appreciate the conversation. And just like that, another episode of How I Deal is in the books. We appreciate all our listeners tuning in. Please, if you enjoy our content, give us a follow on Spotify and Apple wherever you listen to your podcast and throw us a couple stars if you really enjoy it. But until next time, we will see you then.