Account Executive

May 12, 2022

Episode #04 Highlights: Greg Cammarata

🦈 From the jaws of acquisition

Greg Cammarata explains how he snatched a deal from the jaws of an acquisition.

Featuring hyper-personalized video prospecting, late-stage competitors, & a near deal-killer twist. Truly GOAT-level deal-making packed into this one.

Try Greg’s tips today to overcome major barriers & turn a huge risk into a closed-won!

Guest Feature

Greg has climbed the ladder fast at demandDrive. From Sales Development rep to Account Executive, & now Sales Manager. In a few short years, he’ll probably be CEO.

He is the true embodiment of the phrase “teach from experience”.

Greg Cammarata

What problem does demandDrive solve?

Every company needs to grow, but not every company knows how to grow.

Let alone have the right team in place to scale. DemandDrive provides that sales team.

From building your go-to-market strategy to setting tons of meetings. They bring growth to you.

Deal details

Where did the prospect come from?

  • Cold outbound into them. Over several personalized video messages.

Company type

  • Mid-market B2B software company.

Deal Length

  • ~5 months.

Barriers to Overcome

  • The company was acquired halfway through the deal & decided to explore options with DemandDrive competitors

Buyer types

  • Users: Sales leader & sales development team
  • Decision Maker: VP of Sales

Episode Highlights

*Note: timestamps correlate with full conversation

Prospecting: If a picture is worth 1,000 words…what’s a video worth?

(7:24) Prospecting has become synonymous with NOISE.

So many sales pro take the easy route & mass produce general, one-size-fits-all messaging.

While sales is certainly a numbers game, the inbox has never been harder to stand out in.

Fortunately, where one door closes, another opens. Due to the sheer volume of poor outreach, any truly unique, personalized tactics will resonate & produce a ton of meetings.

Greg did just that with video messaging. Listen to how he got his foot in the door here:

Demo: Difference of product vs service? The consultative approach.

(13:47) Most product demos can be, and typical are, a robotic process.

Point, click, feature dump, repeat. While far from ideal, it’s an effective way to see & feel your solution.

But when demo-ing services, no two prospects are the same & every solution has to be unique.

You must take a true consultative approach while weaving the in-depth analysis of their company.

Here’s how Greg does exactly that with his demos:

Objections: Proper discovery helps avoid late-stage deal minefields.

(17:25) Every question matters in the discovery process, especially the ones you don’t ask.

Crucial information can be missed if you stick to the script provided by sales enablement.

Greg found out well into the deal cycle that his prospect was gearing up to be acquired by a much larger company. Luckily his champion was continuing on & sticking with the project.

However, the new owners wanted to explore other options alongside the demandDrive conversation.

Essentially Greg brought his competition to the table because he was on the back foot after being caught off guard with the acuistion.

Hear how he handle this deal-killing adversity & turned things around:

3 Tips to Fellow Account Executives

1. Work smarter, not harder on buyer research.

Once a prospect is in your sights, do the homework & go the extra mile to prepare for your initial outreach as well as the discovery meeting to follow.

With a few strategic Google searches, Greg could’ve seen the acquisition signs a little more clearly & put himself in a better position to close before other competitors were at the door.

However, he was so well prepared in all other aspects of the deal, that they still decided to move forward with demandDrive.

2. Honesty & transparency above all in the sales process.

If trust closes sales, then honesty & transparency are the pillars you need to build on.

If you’re upfront about what you can do & more importantly what you can’t do.

Buyers are more likely to go with the option that’s aware of their limitations. Rather than who claims they have none.

The truth cuts both ways. Prospects will be honest about their reservations with an honest sales pro early on & work in tandem on a compromise. They won’t do the same with the snake-oil rep.

3. Constantly prospect to keep your pipeline full.

“Confidence is the food of the wise man & the liquor of the fool” - Vikram, Michael Scott Paper Co.

A full pipeline is the cure of all sales ailments & can project a ton of confidence to your prospects.

If you aren’t desperate to win a deal, the reps chances to close go up significantly. But prospects can smell commission breath from a mile away. They are much more likely to walk away from a sales rep who seems to just seem them as a job-saving number.

If you’re not engaged in revenue-generating activities (discovery, demos, follow ups, etc.) account executives should be prospecting and creating a large cushion to fall back on if one of your deals falls through.

Watch the full conversation

Full transcript

Taylor Dahlem

Welcome back to How I Deal! Where we discuss past, closed, won, and lost deals, how they played out that way, and want to provide you some solid sales tips to use in your deals today. My name is Taylor Dahlem. I'm a full cycle account executive, turned content guy, and I'm joined by my partner in crime. As always, Junior. How's it going, man? 

Junior Lartey

Great. We built this podcast with the purpose of exposing how The Ideal Deal is almost never a straight line. I think we're tracking pretty good. It's episode four, and I think today is going to be fun. 

Taylor Dahlem

Yeah. I mean, every episode we get better, right? We try to at least, but want to bring on different guests, different perspectives. And just to refresh everyone on how this works, each conversation we chat through a past deal, try to anonymize or at least fictionalize all names, places, things like that, just to keep things light. And I guess NDA nonspecific, right? But we want to dive deep. We want to go from the first time they saw that prospect either in the CRM or on LinkedIn, all the way to getting that DocuSign or whatever your signature tool is approved. 

Junior Lartey

Yes. Today we're chatting with Greg Cammarata. Who climbed from SDR to sales manager and spent a good time as an account executive. Greg, you the man. 

Greg Cammarata

Hey, guys, thank you so much for having me on. Super excited to chat with you both. 

Junior Lartey

Likewise, Greg, give us some insights into your role and what problems demandDrive solves. 

Greg Cammarata

Yeah, absolutely. So at demandDrive, I've worn a couple of different hats here. I started here as an SDR, making cold calls prospecting, doing all that, and shifted into a management role for a while, managed a team. After doing that, I pivoted became an account executive, and now I'm a sales manager for demandDrive sales team. So I've seen the company from a lot of different angles, have worn a lot of hats, and essentially what demandDrive does for its clients. And I have like a one-line answer, I usually say, or one-line response is that we build and manage sales development teams for tech companies and the teams that we build their primary goals, set up fully qualified meetings between your internal sales reps and better leads. But the biggest differentiator about demandDrive is that we truly operate as an extension of your own internal team. And typically, companies will turn to us if they are looking to build up their sales development team from scratch. But they still want the quality of an internal team. Or on the other end, if they have an existing sales development team in place. We can augment that existing team, focus on a new initiative, focus on a separate vertical. But the theme of what we do is that we do this as closely to an internal team as possible. 

Taylor Dahlem

Super Cool, super cool. And the demandDrive. Junior and I are pretty familiar with it, but we're excited to learn more about what you do and kind of how you navigate those processes when you're having real prospect conversations. But speaking of that, let's just dive right in. Greg, what are you walking us through today, deal-wise? Yeah. 

Greg Cammarata

So this is an exciting one at this point. I was an account executive. I was like six or seven months into the role. And the way we're structured is that we have demandDrive itself actually has our own SDRs who prospect on behalf. We have an awesome marketing team. Shout out a GI Alonzo and Alex Ellison. Alex, I didn't call him out as well. Both of those guys are great and they generate awesome leads for our sales team. But this is one of my outbound ones that I got earlier on, and it had a few twisted turns, which is exciting, but ended up being my biggest deal that year. So I was really proud of this one and excited to talk to you about it as well. 

Taylor Dahlem

Walk us through the beginning. Let's start at the start. What did you do to research this deal? 

Greg Cammarata

So the way I researched it is that this is an outbound deal of mine. So I used a few tools to map out some target accounts I want to get in contact with. And there's some criteria that we look for consistently when it comes to account mapping and targeting accounts, the company size, the revenue range, the amount of funding they have. The biggest thing for us is if they have SCRs or BDR. I also use that term interchangeably. So throughout this, I'll continue to probably go back and forth. But if they have strs in place, if they don't have stress in place. So a lot of the research is on the account itself. And when it comes to decision makers, we're looking typically for someone like BP of marketing, VP of sales, kind of nebulous sales development. Sometimes it rolls up under one Department, sometimes it rolls up another, or sometimes it's own separate thing. But those are the main points that I'm looking for beforehand for reaching out. 

Junior Lartey

Is this established SDR teams, or could it also be like we are in a position to start creating an SDR team? 

Greg Cammarata

Yeah, it's exactly that. So can we work with companies that have existing sales development teams in place and we can just augment that existing team? Or if it's someone who has no exposure to sales development or no existing sales moment, we can get in there and build that team from scratch for them? 

Junior Lartey

Awesome. That's a really good trigger to have and to know. Just like, as you're looking at different company profiles on LinkedIn and everything, you're looking at the job tabs and you just know based off of, hey, these signature events, either hiring an SDR or already have one you already know, like, okay, we're halfway there. There's a lot of different ways to prospect, quite frankly. What did your initial outreach look like and what was your messaging? 

Greg Cammarata

Yeah. So the thing that I did in this one is that a big part of our methodology is to do personalized outreach. So what I did to get in contact with this specific account is that I did actually video messaging. So I sent a video to this individual, the VP sales over at this company, and basically touched on a few different things. Like this scenario. They had an existing SDR team in place. I noticed, if I remember correctly, they were hiring for SDRs. And my point of contact posted on LinkedIn. So when I did this video, I think it's important to when you do these videos or any kind of outreach, it's great to be personalized, but also being relevant and explain like, hey, this is my reasoning for reaching out to you. You're not just one person in a thousand people. I'm going to email say, I really want to reach out to you for a specific reason. That's why I really try to drive I try to drive home when doing video prospecting. So that's how I do the conversation. Actually, what was interesting too, is I put all this work in that first touch. It wasn't my first touch that I got in contact with her. It was the second or third touch in the same email change with the video, reaching out with that initial video, reach out. And then when I finally did get in contact with her, she got back to me. She was like, hey, Greg, love the video relevant. I don't remember the exact phrase you hit on points that we're looking to explore. Let's talk something like that. And that's how the initial conversation started. 

Junior Lartey

I love that. Obviously the best is one email and a response. That's not always the case. Right. And in your case, you're saying this is the third touch. You're using video to reach out to this person. Maybe some of our listeners haven't used video in the past. One, what does the video look like or sound like? Coach us for like thirty seconds. How do you use video in your outreach and then tell us the tool. So if someone's listening, they're like, I want to dabble. They at least know where to look. 

Greg Cammarata

Yes, one hundred percent. So I think the theme of video, in my opinion, is to make sure, like, use it as a tool. Explain why you're reaching out to them specifically. Don't just use it as like a digital voicemail because that takes away some of the way. I personally use Loom. I'm a fan of Loom, but I know we have clients that use Bedyard. We use Vidyard as well. So the way it's structured is that when you make a video, it's a screen share. So you can see what I'm looking at, my screen and my face or whoever's using its face is in the bottom corner. So that itself, I think, is a tool because I like to lead off on their LinkedIn page showing like, hey, I'm reaching out to you for a specific reason. Or maybe they're kind of concerned, like, hey, why is this weirdo on my LinkedIn page? And why is he sending me a video of this? And then from there walk you through my example of why I'm reaching out. Like maybe a trigger event, maybe an article. Actually, in this scenario, there was an article that was posted along with the fact they're hiring for SDR. So I had her LinkedIn page, went to the article after, highlighted the part where they were expanding, blah, blah, blah, and then went to the job post being like, hey, I also know you're looking higher for Strs. And then from there, I did go to a quick slide on demandDrive really quick, not trying to bore them. The whole video itself is probably like sixty seconds. If that I try to keep them close, I keep them short. But then after I did that, I just had a call to action. Like, hey, looks fine, is this worth exploring? Get some time to connect next week. And then ended up ended up connecting on that third touch. 

Junior Lartey

Yeah, that's awesome. I love that you're using video. You're sharing your screen, you're showing the exact research and piece as to why you think you provide value. And obviously that's what it took for this person to respond. So without the video aspect, maybe we don't have this conversation about them today. 

Taylor Dahlem

And it goes back to just knowing the buying trigger, like knowing your ICP so well to utilize multi channel and just be like, hey, I saw this and this. Here's how I'm going to help and here's why I'm doing this. All that ties together. So video is great. But also know your ICP, know your target, know your buying triggers. That's the kind of stuff that's ultimately going to convert. Greg, obviously, we talk about the hardest stage of the sales process. It's not necessarily the prospecting aspect. Yes, it's difficult. But once you set that meeting, the work isn't done right, the discovery comes next. Understanding. All right, yeah, I saw some triggers, but I want to dive a little deeper and see if I can create that gap or create that. I really understand that need or that pain, because as you know, when if you can't uncover the pain, you're likely not going to move anywhere and you're not going to have a strong demo in the whole process. All that hard work prospecting falls apart. So how did you organize that initial meeting, that initial conversation, and what did you learn? 

Greg Cammarata

Good question. So I would say my initial discovery call isn't anything that's too ridiculous or anything that's too blue. Typically, what I like to start off with is learn as much as I can possibly about the company and about the individual from there. Going more of a deep dive from what I hear from them. I do deep dive on demandDrive, but I obviously will focus more on what I gathered as pain points during that quote-unquote pitch part, then just open it up for any questions and then just figure out what next steps look like. So I wouldn't say there was anything too unique in there. I'll look to see if they've worked with an outsourced SDR firm before, see if there's any certain attributes to a firm that's important to them. You learn about what their current sales development team is, and then kind of get an idea. I don't like to talk about this yet, get an idea on what expectations and how success looks like for them, because then when I get to that next step, I really want to dive deeper on that. That's typically how that first call is going to work. One thing, though, that was interesting about this deal, and I'm sure we'll get to it as well. But one of the biggest wrenches that was thrown, I didn't uncover during the Discovery call. I found that out later on and it made this whole thing take a right turn. But we ended up getting back on track, which is good. 

Taylor Dahlem

Yeah. Right. Well, I didn't find that one small, tiny piece of information. It snowballs after that. Luckily, we'll talk about how that got corrected, but a lot, probably. Ninety percent of deals fall apart because you don't find that small aspect or that one thing that might hold it up. 

Junior Lartey

Before we roll into this demo stage, just want to make one comment in Discovery. If you don't find that one thing that we will talk about later, the impact is it extends the time of the sales process. Maybe you typically close deals in one to two weeks. Well, you didn't uncover this one piece, and now you're extending that to four to six weeks as compared to the two to three or one to two. And then what does that mean? Well, now your deal has more risk, there's more opportunity to lose. So that's why it's like huge and the ability to uncover is big. But to not uncover and get back on track, I mean, that's why your sales manager. Right. Like, you obviously figured that out. I think it's super cool. So we'll get to that in just a second. But rolling into the demo stage, this can sometimes be a yawn. Right. Let me show you every feature that we have. It's hard to be succinct and show the exact impact or ROI of what this can do. So how was your experience different? What did you do to keep them engaged through that demo stage? 

Greg Cammarata

Yeah, that's a really good question. So typically the next step on demand drives and we don't do a demo per se. It's more for like a presentation deep dive on their company. Because the thing about us is that we can work with companies in a lot of different ways. Whether it is building a sales development team from scratch, whether it's augment the existing team, the case for this client, or this prospect. At this point, we were augmenting their existing team. So what's important during this stage for us is to be super consultative, learn about what's working, what's not, provide our feedback on what we can potentially do better. So typically, what this presentation looks like is that it consists of deep dive on the company, making sure they leave without any unanswered questions. On top of that, diving a little bit deeper on what I learned on that discovery call, and kind of the back and forth when it comes to being consultative. That's what we'll focus on as well. But then the biggest point, too, which is nice and keeps the conversation very conversational, is talking about expectations, goals, how they measure success. And that's for me because it also ties back into our company's business model. We operate as closely to an internal team as possible. So if we're not super conversational, and if there's not a lot of back and forth during that process, then it's going to most likely derail the actual engagement as well. So I guess if I had enough point to one thing specifically, being consultative throughout that follow up call is the most important thing for us. 

Junior Lartey

So post discovery, you're doing more of a deep dive, less of. We're jumping into the platform and demoing. And in that deep dive, discovery, you've said we found pain. We know it's a pain point. Let's talk more about that pain, and that's what the deep dive is. It's like understanding exactly how you solve that pain and tying it back to what you can do. Am I understanding that correctly? 

Greg Cammarata

Yes, exactly. I don't know if I thought I might have missed this when I was referenced discovery of the call. So the big pain for this client was the fact that they could not scale fast enough. They had ambitious sales development goals, and they needed to hit, like, X amount. They needed to hit X number in a certain amount of time. So what we are going to do is to bolster their sales development efforts, but also at the same time, make sure they don't lose that quality of what was working internally. So exactly right. I learned that during discovery call is the point they're paying. They were super concerned about like, hey, we really don't want to like what we're doing now works. We just need to do more of what works. So that was big at the time. That was most of the consultation. Part of that fault calls just be like to discuss how we'd fit in with what they're currently doing and to make sure and to highlight how we could hit those goals that we briefly touched on during that initial call, and then we dived a lot deeper on in that follow up. 

Taylor Dahlem

I guess, Greg, we've heard the saying no problem, no sale, right? Like a pretty famous phrase in a lot of ways, but this can also apply in your own sales cycle. If we don't run into problems along the way, that's not necessarily always a good thing. But for me, it's like, well, all right, this deal is moving along. We're checking all the boxes, everybody's happy. And then all of a sudden they're like, oh, we went with somebody else or we're just not going to move forward and you lose that sale. And then a lot of times you don't know why that's because you didn't run into those kind of those barriers or uncover those problems. So we've been alluding to it. But what was that major barrier objection that you had to eventually overcome? 

Greg Cammarata

Yes. And it's actually kind of funny in a way, too, because, well, I'll backtrack and just say what the issue was. So after our presentation, I recently found out this company was about to go through an acquisition. So that completely getting to that point where you have to resell individuals backtrack to take two steps to move one step forward. Or in this case, it was like take five steps back to move a step forward. It was a lot of chaos. And then the interesting part about that as well is because I guess the one nice part about it is that my point of contact did stay consistent throughout. There was a few other stakeholders as well. But even with the new structure, I'm still talking to the same person. But what happened is that now that there's other people involved, they also saw the need for a partner like demandDrive. But at the same time, they were like, hey, let's talk to some other people as well. It was kind of funny because I was the one who initially got this idea in their head. But now these other partners like, hey. So I basically accidentally brought in competitors had to compete against just because from doing what I did. And they liked the idea of let's talk. So after that, I had a couple of other calls with our post presentation, talked about different value ads and talked a little bit about how we position ourselves to get other competitors. But yeah, before you I don't know if you have any follow up questions after that, but yeah, that was the big thing that derailed it for a while. 

Taylor Dahlem

I mean, that's insane, right? Like, most barriers are all we don't have budget or we got different priorities, different goals. But to be acquired during the sales process is rare. And that's usually a death sentence, right. At that point. And like, even said, additional barriers came up after that of, hey, we still like this idea, but let's talk to some other people. Let's price shop you around. And that is a killer. I guess any other barriers come across or spur up after that, or was that kind of the main couple that presented themselves? Yeah. 

Greg Cammarata

So it was almost like a two part. So the acquisition was a barrier, but that itself, I found out, wasn't really an issue because they still wanted to pursue the same course that the company was going to do initially. Where the barrier came was the fact that they were like, okay, this is a good idea. Like, we like this concept. It makes sense. Now let's start. Maybe there's some other companies that we could talk to as well. But the thing is, I was initially the first one there, but then these other parties got in the mix as well. And essentially I try to do a few things to get over that. This is over. Basically. I had another follow up call talk about differentiators how we position ourselves. But the biggest thing that I just try to drive home at the end of the day was like, hey, I know you're talking a lot of companies at this point, but at the same time, the work that we do for our clients is essentially what I did to get in contact with you. And I think that's a major differentiator that's going to help lead us to when you're selling this to your other team members. Just remember, like, hey, what we're looking for this company to do, they did to us. So it might be a value add right there, and it ended up being enough to get it across the line. 

Taylor Dahlem

It's a city for unique position, too. We're big advocates of like, we want to be the best users of our product in your world and in your industry. What you sell. How well did I sell you? All that's a peek into what we can provide for you, and it's also probably your greatest weakness. So you didn't hit certain points. And they're like, well, we don't want that. 

Junior Lartey

Okay. Last week we put out a poll asking where most people are getting the actual yes or no. At some point, you have to ask for it, ask for the close. So in your case, where did the yes come from? Email, phone in person. And how did you ask? 

Greg Cammarata

That's a good question. So the ask for this was that's a really good question. It was over email, I believe, or the confirmation was over email, but we discussed it on that follow-up call I referenced before. Like, where I talked about like, hey, this how we differentiate. So I think you should move forward with us. It was discussed then, but the official like, it was solidified over email, if I remember correctly. 

Junior Lartey

So that's also what the poll eventually came out was most confirmations are happening over email, and I have absolutely no data set on whether that's good or bad. But I just want you to know, like, as AES that are selling. Right. Confirmation can happen over email. It can happen over the phone. It can happen in person. It's less about where you are and how you got the s and more about what you have uncovered and how much pain you can solve for them. And Greg, I'm hoping you'll agree with that statement. 

Greg Cammarata

Yeah, no, I totally agree with that. 

Taylor Dahlem

Greg, let's wrap this thing up. So after walking through this whole deal and obviously other deals, you've been a part of what are say three things any AE listening today can do to inch closer to that closed one on some of the deals they've gotten the pipe. 

Greg Cammarata

Yeah. I would say the first thing is to work smart. Once you have someone in your pipeline, do your research, do the proper preparation when it comes to Discovery presentation and when you do your homework and prepare, it's going to really pay out. So I would say that would be number one. Number two, I'd say throughout the process, from Discovery to presentation to if there is a follow-up call, for whatever reason, just being transparent and just being as honest as you can really pays and in my opinion, will make the whole engagement helps the engagement lead off the right way. And also throughout, it sets the tone for how this relationship should go. So I would say that would be number two. And number three isn't necessarily an account executive strategy per se or a closing strategy per se, but I think it's super important. It's just have a full pipeline. And what I mean by that is obviously marketing is channel you're going to get leads from. If you have an SDR who is working on your behalf or working on your team, you're going to get leads from that channel. But in my opinion, if I'm not working on if I'm not doing any revenue-generating activities at the moment, like working with Prospect, whether it's on Discovery call, presentation or back and forth, I think it's important just to prospect and be that own person because at the end of the day, when those deals that you're relying on that you're counting on falls through, if you have a full pipeline, you're able to like, all right, that fell through. I did everything I could to save it. But at the end of the day, I have three other people that I have called schedule scheduled this weekend. Just like that mentality. I feel so helps during the actual presentations and Discovery calls because then you don't have that feeling of being like make or break kind of allows. It just takes some of the weight off your back and you can be a little bit more relaxed. So I think that's important. And then by prospecting, it helps with the actual presentations and Discovery just because you don't have that added pressure. 

Junior Lartey

Awesome. I think. Yeah, those are great things to keep track of, to be on top of Greg. It was great to have you. If you tuned in today, go connect with Greg on LinkedIn do some video prospecting we wouldn't be here without it. And add acquisitions to your discovery dock because your pipeline will thank you later. 

Taylor Dahlem

And just like that, another episode of how ideals in the books. Thanks so much Greg for joining us and thanks everyone for tuning in. We will see you next time. 

Greg Cammarata

Thanks for having me guys. Much appreciate it. Bye.

You'll like these emails 🥒

Pickle writes to their friends every few weeks with spicy tips to make their wall-to-wall meetings suck less.
Thank you! Your submission has been received!
Oops! Something went wrong while submitting the form.