🥷 Boosting a Deal in Transit
How I Deal Episode #01 - Spotify & Apple
Junior Lartey dives into a deal he won after showing up when the buyer was in VERY late stages with his biggest competitor.
From initial LinkedIn research to the signed PDF, he talks through how he won them over while providing tips you can try today!
Guest Feature
Junior Lartey is a Senior Account Executive @ Pickle. He cut his teeth in the sales game through the door-to-door route. Not a path for everyone; but if you can build instant rapport & identify pain by boldly knocking on their door…everything else tends to come easier.
Junior then climbed the ranks in an enterprise tech company & is now helping Pickle, a conversation intelligence solution, grow as sales hire #2.
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What problem does Pickle solve?
It sucks to waste hours listening back to recordings to find that deal-winning gold nugget.
Pickle enables full-cycle sales pros to capture, find, & share key moments in Zoom meetings instantly.
Deal Details
Company type
A mid-market recruiting agency that operates like a sales organization.
Buyer types
- Users: Recruiters who operate as full-cycle sellers.
- Champion: An end-user (also Junior’s brother-in-law)
- Decision Maker: VP of Recruiting
Episode Highlights
*Note: timestamps correlate with full conversation
Prospecting: Hyper-relevant timing, okay messaging
(5:54) Junior learns that the prospect is already mid-trial with his biggest competitor. He had to sprint to catch up!
He had to “boost” this deal in transit. Meaning the prospect had already done their solution research & are evaluating competitors, but they haven’t moved forward yet.
Junior’s messaging to the 3 different decision-makers (VP of Sales, Executive Recruiter, & the head of Enablement) was relevant & timely enough to give him a shot.
Here’s how it went down:
Discovery: Separate meetings for different buyers
(12:20) Want to hear a joke? Attempting to run proper discovery in 30 minutes with multiple buyers in the same room.
Junior covers how he avoided that train wreck. Running separate discovery conversations with each of the 3 buyers instead.
Which led to the ability to really dig into specific pains & what each buyer wants to achieve.
Enabling him to create a department-focused demo centered around their uncovered pains & goals.
Listen to how it unfolded:
Objections: Overcoming buyer burnout in a competitive deal
(23:48) Having entered the competitive deal so late in the game, Junior was pushing to get to the advanced stages of discovery & demo faster.
Normally this is a typical approach considering the situation. However, he failed to recognize in discovery how burnt out the buyers had become after juggling pitches from multiple competitors.
The prospect had gotten to the point of not even wanting to move forward with any conversation intelligence tool.
Luckily he developed a strong enough relationship with the deal champion, that he got the heads up.
Tactfully changing strategies, Junior decided to slow things down with the prospect & was rewarded with ultimately winning the deal over his massive competitor.
Hear it from him:
3 Tips to Fellow Account Executives
1. Identify Late-Stage Buyers
As Mark Wahlberg did in Italian Job, you gotta boost deals in transit.
Leverage every resource you can to identify prospects actively in buying cycles with your competition. LinkedIn, G2, Amplemarket, Slack communities, etc. are all great tools to help you achieve this.
Search Set up google alerts for keywords to trigger when someone asks questions like “how does (competitor) compare to (competitor)?”
You are instantly a part of the conversation.
2. Peer Prospecting
It’s imperative to build as many relationships as you can in a deal.
Often times the most influential people are the end-users, who don’t typically make the final decision. Most sellers overlook users & go straight for the top brass…DO NOT DO THIS.
Junior is constantly connecting with the end-users of his solution & learning what they value most. They can become internal champions at this point & do the selling for you if enough value is there.
Pickle coined this play Peer Prospecting and broke it down in detail here.
3. Leverage Texting with Decision Makers
Post-discovery, pre-demo ask you champion and/or buyer if it’s cool to reach out via text.
You’ve ideally built a relationship while prospecting & after discovery, so it shouldn’t be a huge request.
Texting helps the relationship progress further & creates an environment where the buyer speaks more candidly than they would over email, a Zoom meeting, or in a formal demo.
Watch the Full Conversation
Full transcript
Taylor Dahlem
Welcome to the first edition of How I Deal! Where essentially we discuss past closed one and lost deals, how they played out that way, and things that you can steal from us today and essentially level up your sales game. My name is Taylor Dahlem. I'm a former full cycle account executive, turned content guy, and I'm joined by my partner in crime, Junior, our superstar seller here at Pickle. Say, what's up, June?
Junior Lartey
What's up? Happy to be here. Provide some insight, steal some knowledge, but not all my stuff.
Taylor Dahlem
Absolutely. Since this is the first edition, it's just June and I chatting about some deals within Pickle. But obviously, the goal will be to go on and chat with other account executives, to get some perspective from outside our walls here. But how this is going to work each conversation, we just want to chat through a past deal. All names, places we'll try to fictionalize some of that stuff, of course, but we really want to dive deep here, go next level, just kind of scope in on a single deal from the first time you saw the prospect on LinkedIn, all the way to completing that DocuSign. So I guess let's just dive in. Junior, what deal are you walking us through today?
Junior Lartey
Okay. Yeah, I've got a deal from a recruiting agency, and I'm excited to talk about it. Perfect.
Taylor Dahlem
So recruiting agency, give me the scope. Right. Big, small, medium, SMB. And what are they typically targeting? Right. Like, how did you research this deal?
Junior Lartey
Yeah, this deal is a little bit different. Typically, we're selling directly from Ae to VP of sales in this scenario is a little bit different. The Use case was pretty similar, but ultimately, the recruiting people do something very similar to what account executives do. So we took that idea and kind of ran with it and really pitched your recruiters are doing something so similar to the AES that they'll be able to get the same value out of Pickle that traditional account executives get. They're a mid-market company, and they do anything from entry-level recruiting up to executive recruiting. So a big scope spectrum. They're really cool outside. They don't quite fit into the recruiting agency box. They're doing things differently, which I think really helped us get this one across the line.
Taylor Dahlem
Got you. And was there any particular things you Hone in on? Maybe a personal relationship, things like that that I don't know, caught your attention to pulling the trigger on starting this process.
Junior Lartey
Yeah. So the nice thing about this one is I have a brother-in-law who works there, okay. And we just talk about business. How's this, that or the other.
Taylor Dahlem
It's never gone past, right?
Junior Lartey
No, never gone past there. And he mentions to me that, hey, we're trialing our biggest competitor. The Pickle's biggest competitor. And I was like, dude, you're looking for this type of tool, you can insert my name. Still, it didn't go past there. He gave me that intel. I beat him up. And then I was like, I'm going to take it upon myself till I get in there and start prospecting. So the insider knowledge that I had was they're on a trial, they're looking at this type of tech. And that to me was like, hey, the door is open. It couldn't be more relevant. The timing couldn't be better. I guess it could be better, right? Like, they came to us first, but in all sense, it was hyper-relevant to that got you.
Taylor Dahlem
And that obviously leads into the next step, right? So you've got the research done. Luckily, you had an inside track. I'd love to kind of hear your perspective. If you didn't have that inside track, would you do anything differently and how that would look? But you mentioned targeted relevant. It made sense to have that conversation. Were there any prospecting, hacks or approaches that you had that maybe set you apart to get your foot in the door, at least? Obviously, outside of the connection, maybe speak to what would happen even if you didn't have that connection or how you'd go about it?
Junior Lartey
Yeah, there's a funny meme out there that we created here at Pickle. It's called Boost. It in Transit. Quite literally, when a prospect has done all the research, they've evaluated some of your competitors, they haven't quite moved forward. And then you just show up and you're like, hey, well, what about me? And then you're able to quite literally, like, you're boosting that deal as is going. So for me, it was just like, hyper-relevant, right? It wasn't my message. It wasn't anything special that I did for this deal specifically. It was the fact that they were completely envy market looking to move forward with the tool. So by the time the cool thing about this was it was one email. I did all this research, I mapped out. Okay, I clearly need to talk to the VP of sales here. I needed to talk to the executive recruiter, who is the executive recruiter. She manages all the recruiting teams, and then they have a trainer and enabled it. So I was like, hey, these three people I know I have to get in front of. And so it's the VP of sales that I started with, connected on LinkedIn, dropped him a message, and within minutes, actually, he just took my calendar link and booked. It was so hyper-relevant, right? Yeah, that's the thing. When the timing is perfect, the message just has to be decent.
Taylor Dahlem
Just a little on par. Like, just hit a pain at all. And the fact that everything else fell in line, it makes it that much easier to get across the goal line. What about, obviously that's the buyer side of things. Did you do anything on the user side of things or the end user, the person that's ultimately going to be needing this tool did you do any approach there. Obviously, you said you knew you had a connection with one of the sales reps already, but I'm interested to see that side of things as well.
Junior Lartey
Yeah. So my main source was my brother-in-law. And you can look at him as a parallel to any champion, quite literally, because ideally, what you're doing is you're connecting with the users on LinkedIn, either as you're reaching out or before you're reaching out. I have a lot of relationships with the AES of companies that I'm prospecting. It just so happened that this one was my brother-in-law, who, let's be honest, should have championed sooner, hence get you in the door. I did push for information. I was like, hey, is it a trial, as in, like, you're just trying it out, or is it a proof of concept? Those are two different things. Or are you, like, unsure about tell me what you know. I got that one. So I tried him for a bunch of information. He ultimately gave me the names of the executive. The one I wasn't sure about was the executive recruiter, because they had a few. But she was the one who drives all the teams. So he did provide that insight, which was very helpful. She was the ultimate decision maker in the end.
Taylor Dahlem
Yes. Kind of a direct line of the source. Which again, even brother-in-law or not, you can build a relationship with somebody that you might never even think to connect with because they're never the buyer. They're never going to be in that decision. And like you said, you'd be surprised. The power of the champion. And heck, we've built out entire peer-to-peer prospecting sequences. Our whole goal is to ultimately connect with the people that are going to be using a platform like Pickle or insert any platform. And from there, if you get their buying, you get their interest. You best believe they're going to at least help you out. Even if they're not going to be in the meeting room, they're going to help you out in any way that they can, especially if it adds value. Yes. Maybe your brother-in-law might have some bias. Honestly, that might be a tougher sell. If Pickle didn't do anything for him, right? It would make him look just as bad.
Junior Lartey
He'd be like, hey, you told me to intro you, but your tool sucks.
Taylor Dahlem
That's an awkward Thanksgiving conversation, right?
Junior Lartey
Yeah. I'm not going to Thanksgiving at that point. That's out. Okay. But really quickly. So the messaging to those users. Like I mentioned, I'm connecting with the account executives of every company that I prospect. So the messaging to them is especially after a meeting. But if a meeting has already been booked, I'm hitting them up and say, hey, I'm meeting with so and So, your VP of sales on X Date. I would love to either connect before then. I would love to get you in front of this resource. I would love. Here's my call to action, whatever it may be before then. I'm just trying to collect data. Like, hey, do you have a tool? Do you use that tool? If they respond and say, hey, we use your competitor, how much are you logging in? What value does it provide?
Taylor Dahlem
It doesn't end that. Hey, we use your competitor.
Junior Lartey
Yeah, we use your competitor. Great. Give me more. I'm asking for more. We're peers. We're the same level. So anyways, that's outside of the deal we're talking about. But I just wanted to throw that in really quickly about deals that you're currently in and how to use the users.
Taylor Dahlem
And if you're ever interested in this kind of. Yeah, if you're ever interested in that, that pure prospecting play. Junior is a great guy to connect with and have that conversation. But I guess getting back to the deal, right? Like, talk to me about. All right, you've got the prospecting done. You've got your internal Champions, you've connected with the buyer. They've booked on your calendar. It sounds like almost instantaneously, which a lot of people, it'll get them jealous out there that have played out that well because ninety-nine percent of the time it usually doesn't. But they booked a meeting.
Junior Lartey
Awesome.
Taylor Dahlem
You're in the first meeting. Now they've joined, they've entered the waiting room. You've got the butterflies that accept that they've even gotten there. But now you're letting them into the Zoom room, so to speak. What happens from there? Talk me through the discovery, quote, unquote part of that process and maybe how it helped guide the rest of the sale.
Junior Lartey
Okay, so I learned early on that there's these three decision-makers. Here's the hard part. You've got three people that are going to influence the decision. In my opinion, I don't want to meet with all three of them at the same time. Okay, so with this Landon, I guess I just dropped his name, but nobody knows him. Landon, right. He booked with me, and we had a great discovery. He was the one who initially was like, we got to get this tool, we got to get this tool. He was, like, driving the guy, which was really nice. So he gave me some great insight. We had a good conversation. And then I specifically asked him, I said, hey, can you help me book individual meetings with the executive assistant, one of the decision-makers and training and enablement. I made a very distinct point. I want to meet with them separately before we get everybody together. A lot of times what happens is you get three decision-makers, they decide on a date, you show up, and then it's like, how do I get discovery out of three different people in thirty minutes without showing products? It's so hard. It's so hard.
Taylor Dahlem
And to connect with them on that individual level.
Junior Lartey
Right.
Taylor Dahlem
Like, how do you build a relationship, which is really what it comes down to. Right. The relationship you build, especially in this first conversation, if it's split three ways, you've got a third of a relationship with three people.
Junior Lartey
And the thing is, too, is it's three separate people that are doing they're tied to totally separate responsibilities and what they need to accomplish internally. So the VP of sales, he is closing deals for the company. So he's using it to further those sales conversations. The executive recruiter, she's using it as a way to hand off information between us talking to a candidate and getting that information to the hiring manager and then the training and enablement. He's building out a whole LMS onboarding system because they're trying to hire one hundred people. So those are three totally different ways that I need to help them understand how Piccolo can provide value there. And it would be really hard for me in thirty minutes, all three of them together to pull those insights out. Yeah.
Taylor Dahlem
And make it feel again like a truly personalized conversation that's meant for them, like, hey, I don't care about anybody else in this moment. How can I help you? We don't help that. I'm glad I know that now. Or maybe let me take this to our product team and figure out how we can build a better solution in this way. But it's more of that consultative approach that you hear about all the time on LinkedIn and places like that, I guess. How long did it take?
Junior Lartey
Right.
Taylor Dahlem
The three conversations, it spans across obviously more than three days. What does that look like for you?
Junior Lartey
Okay, so we got to keep in mind they are trialing my biggest competitor.
Taylor Dahlem
Yeah.
Junior Lartey
They're in the software already. They have licenses.
Taylor Dahlem
So I'm like, you're late to the game, right?
Junior Lartey
Oh, yeah, I'm late to the game. Not only am I late to the game, but I came in Sprinting. I was like, closed before I get here. So we got to move so fast. So I meet with VP of sales Tuesday. Can you help me get these other two meetings before the end of the week? It ends up being Wednesday, ends up being Thursday. And then we have at the end of those calls, I'm scheduling a fifteen-minute Friday recap. So I get all three of those discoveries. I'm like, let's just talk for fifteen minutes. It's not a demo. It's just let's quickly connect and figure out what's going to happen from here. I now understand their pains in my fifteen minutes. We meet on Friday. This is all one week. And I say, hey, I very clearly see how Pickle can provide value to the sales team. I understand the hand-off situation that you're trying to accomplish, as well as they're like doing some one thousand and ninety-nine stuff. So that was a whole nother beast that Pickle can help tackle. And then the training and LMS, I can plug Pickle in and solve some major problems across the board. Do not sign before this demo. I'm like asking. I'm basically just asking, don't move before me. So then we all connect on Friday. It's a really positive experience. We schedule a demo for the following Tuesday, and at that point, I've got them on pause with the trial, and they're ready to look and take pickle very seriously.
Taylor Dahlem
Wow.
Junior Lartey
Yeah.
Taylor Dahlem
And again, not even a guarantee, right? You're asking. It kind of backs against the wall here. But maybe the relationship prior to helps with the internal champion, but maybe it didn't, right? Ultimately, it came down to very uncontrollable factors. But as some say, it's better to be lucky than good, right? But you're also very good at the same time, so that helps. All right, let's move through the next steps here. I think obviously the most important part of any sale speed to be is the discovery part. So what did you learn in that conversation? And maybe let's dive kind of right into the demo side of things. Like, obviously, it's a necessary evil, but how did you tailor that experience of the three different conversations that you had into that presentation of the product, the finally, the unveiling, so to speak, the guy behind the curtain? How did you do that? And how to keep them engaged?
Junior Lartey
Yeah. Demo stage can be so hard. It can be like you mentioned the necessary evil. Hey, we have to see the product before we do anything. And people can lose interest at this date. So we were fortunate enough. This is a Utah-based company, so we can get there in person. So Tuesday we have a demo, we show up, we do that B to B thing where you bring lunch. It's like, hey, if you let us in, we'll feed you, which plays really well. You can do this remotely, mind you, right? You can do that remotely. Hey, we're going to meet at twelve, go through this demo. Can I send you lunch? People will respond really well to that. So we show up myself and Cofounder Kamala, and our plan is to go one by one. We're like, hey, VP of sales, we're going to spend ten minutes outlining your problem. Executive recruiter, we're going to spend ten minutes on your problem. And then training and enablement will spend ten minutes on your problem. So we let them pay. While you're in here, feel free to check your email. Feel free to do the things you need to do, aside from when it's your ten minutes, when it's your ten minutes. Let's get you in front. And quite literally, when I say in front, we're sitting at the end of the conference table looking up at the TVs demoing together, and that stole the experience. It completely turned things around for us where when we were meeting with executive recruiter, the VP of sales who already had his turn, he was like, but wait, I want to see how you're going to help her as well. Yeah.
Taylor Dahlem
Okay. So there's, like, genuine interest at that point where across departmentally. Right. Where everybody's in the same room, you gave them the option out almost to just tune out. But the way you did it, it almost made it irresistible, though, to want to chime in.
Junior Lartey
Yeah. There are also a few things, like, within the platform that overlap a little bit. So as we're talking to enablement and training, and I'm talking about building some collections in some ways to get onboarding and ramp time and that kind of conversation executive recruiter is also like, oh, I didn't even think about that because my managers are for sure going to want to see members on their team tap into that. So a lot of crossover there that makes it hard for them to tune out. But being present and being like, hey, this ten minutes is specific to you. Really open the door.
Taylor Dahlem
That's super cool. And yes, we're in the B to B tech space. We're in this remote world. Most of our deals and conversations come from a platform like Zoom, right?
Junior Lartey
Yeah.
Taylor Dahlem
But sometimes it does make that difference. If you have the opportunity to go in and have this conversation, software can be an in-person conversation.
Junior Lartey
Yeah.
Taylor Dahlem
And it's kind of when you say a lost art, but definitely, something that over the past couple of years has become less and less normal. But it's really cool to see how you can use that to your advantage, as well as just a screen share over Zoom as well.
Junior Lartey
Okay, let me insert two things real quick. One is post-discovery, pre-demo, we tapped into texting, which really helps the relationship. Just texting the executive recruiter a couple of things, like over the weekend and before the meeting, just like getting familiar with each other. More familiar, like business to business, how it's going to work, and intentionally not answering questions. This is a strategy you can try, right? Intentionally not answering questions via email, but then knowing that, hey, I said I would text you or like, we broached that topic. So now I'm going to quickly text you like, hey, for the one thousand and ninety-nine idea, here's what I was thinking. So there's that. And then two is I can see how someone would think, well, why didn't you just do ten minutes with you in Discovery? In ten minutes with you in Discovery, in ten minutes with you in Discovery. Because I didn't know them at that point. And it would have been so awkward to be like, hey, VP of sales, I'm not talking to you, enablement, I'm not talking to you. I'm just, hey, don't talk. It would be so awkward to do that. But because we had built a relationship and the discoveries went so well and we broached texting, those were two things that just really helped that when we got to demo. It was more of we're at the front level providing value as compared to, like, the business level of providing value.
Taylor Dahlem
Yeah, I envision that approach. The ten and ten and ten here where it's almost like separate interrogation rooms. All right, I'm going to hop between each everybody knows this game is happening. You're pitting each other or against each other there. And it's just one of those things where nothing damages the relationship more than just that initial. Like, what's your angle? What's your play? I smell what's the terminology here, like, smelling the Commission breath on it. It's just one of those things that the more you're just open and honest about it, you have everybody have their time individually, but as well as feel heard when it's a group meeting, that's huge, let's walk through these last two pieces, and then we'll wrap up. But you've got the demo done. You tied it back. There's a ton of value. You're texting. Things are going really well. A lot of buying signals, but obviously nothing in sales is a certain thing until you get that DocuSign completed. Right. So what were the major barriers that came up? Maybe some objections? How did you walk through those or work through each one of those?
Junior Lartey
Yeah. Okay, so this is not a bait and switch. I've been talking about how they were trialing our big competitor. This is what I didn't uncover in discovery. This was my mistake big time. I had been approaching it as, like, Holy crap, we need to rush. Like, we can't let them sign before us. They are trialing my biggest competitor. If I can win this deal, it would be a heaven sun. They had been burnt, as in, like, exhausted then going through this for too long. So their barrier was they were actually not interested in my biggest competitor. They were not even interested in moving forward with the type of tech they got to that point where they were so exhausted because they had been pushed and pushed and pushed. And here I was also pushing because I'm like, fetch. They're going to close before I can get in here. So I'm, like, pushing these things fast. So the actual closing process post-demo happened slowly. It was another two to three weeks before it actually closed. And had I understood that if I had uncovered that in the beginning, that they're not trying my biggest competitor to move, but they're waiting for this trial to be done so that they can breathe totally different. So me pushing that hard actually stalled it out in the end got you.
Taylor Dahlem
So it was kind of that inflection point, right? It could have gone either way because you didn't uncover that which caps off to everybody doing well and discovering focusing on those types of objections or early warning signs in your first meeting, because you could easily lost this deal right at that moment, no matter how fun the texting relationship was or how deep you were? Any other barriers, objections, things like that? And if none, let's just move into like, how do you do the direct ask, right? Like How'd you beat around the Bush? How did you close this thing up?
Junior Lartey
Okay, so I think those are tied in this case where like, that barrier is delayed. It got to a point, maybe a week and a half after demo, where our sales process can be really quick. We can close things within a week. It's typically two weeks, a month if they're like, hey, we got to be more formal. So a week and a half after demo, I'm now texting VP of Sales and I'm getting very direct, hey, so and so what do I need to do to get this across the line at this point? Like the trialing is done and they're going to make a decision on it'll be pickle or nothing. And nothing is horrible. Not for them. It's horrible for me because that means I was not able to show them how we can solve the problems that they told me they have and that I was able to uncover and solve. So that was what I was up against in the end was pickle or nothing. The texting honestly drove it home for us. It really built that relationship, got it to a point where we found a few additional relationships within the deal that we didn't realize were quite there. Pickle CEO knowing some people over there. So he started texting as well. And that ultimately got us across the line.
Taylor Dahlem
Turned it into kind of that team deal. Right. Or the multi-threading aspect that you started, but made it even stronger with bringing in some other people in the organization, which I think ultimately sends us into the wrap-up here. Throughout this conversation, dropped a ton of knowledge, but maybe let's throw kind of a summary out here. Maybe what are three things that NEA listen to us today can do to inch closer to that closed one on some of the deals that got in the pipeline?
Junior Lartey
Yeah, we love to boost it in transit. If there's a way that you can find that your prospects are looking to buy your type of tech, you've got to find a way to find that out. Linkedin has been a great resource for me personally. I see people posting saying, hey, what do you think about this versus this? And one of those, this is not me. I'm in their DMs. I'm cold calling them. You have to find a way to figure out if they're looking to buy. The other is you got to find relationships within the deal. A lot of times for me, that is the users. I do a ton of peer prospecting. I'm constantly reaching out to AEs that I know internally will go to bat. Ford Pickle, those are huge. Maybe a third thing would be like at the decision-maker level. Try to get to that texting level. If you can text, that's a lot more personal. They're willing to expose because it's more off the record and they're willing to expose some things that they might not via Zoom or in a demo where their other peers' people at their organization are. So I top it with those three things.
Taylor Dahlem
Perfect. Excellent way to wrap up our first edition of How I deal. As we said at the top, I'm Taylor. I'm a retired Ae turn content guy. And Junior, thanks for gracing us with your presence and awesome story when it comes to how you're currently closing deals with Peel. Our goal is to keep kicking these things out week after week with other AE's in the future. But until then, in thanks, Junior, I appreciate it, man.
Junior Lartey
Yeah, happy to be here. Excited to see what comes next.
Taylor Dahlem
Cool. Thanks.
Junior Lartey
Yes. Bye.
