🙏 Hitting full send via text
Nick Smith, who's sold services his whole career, chats through his first product closed deal.
While the transition seems small, there's tons of nuance in each version of the sales cycle.
Especially considering the deal metrics & overall size of the opportunity (1,000+ employees).
Nick did his homework, knew his persona in & out, and overcame a few barriers along the way.
Guest Feature
Nick Smith was a Submarine Nuclear Technician in the US Navy serving on the USS Montpelier.
He then entered into consulting & sales world 10 years ago and never looked back.
Currently, Nick is an AE at WorkSpan & creating funny sales content on TikTok (@nickreedsmith).
What problem does WorkSpan solve?
WorkSpan builds a bridge between your CRM and your partners CRM.
Companies that are selling a lot through partnerships and ecosystems, WorkSpan helps build the infrastructure that powers their programs.
Deal details
What are you selling?
- Software product for backend integrations.
Where did the prospect come from?
- Target account list from the marketing department.
Company type
- Big ISV company. Well-known in the AWS, Microsoft, & Google ecosystems.
Prospecting method
- Personalized cold email after trigger-focused research.
Barriers to Overcome
- All the classics: pricing, legal, timing, etc. But had responses ready to go beforehand.
- Got ghosted halfway through that deal. Sent a hail mary text to re-engage…it worked!
Buyer type
- Users: Salesforce Admin, Revenue Operations Team
- Decision Maker: Alliance Manager
Episode Highlights
Note: timestamps correlate with the full conversation
Prospecting: Keep cold emails painfully short (8:41)
Discovery: Competing against no-decision (12:17)
Objections: Addressing deal pitfalls to build trust (22:53)
3 Tips for Account Executives
1. Get in front of the timeline.
Prepare for & confront barriers before they set you back.
2. Deals are fluid. Listen & adapt.
Don't ask a question just to check a box.
3. Be creative & interrupt patterns in your outreach.
Don't just send 100 emails & call it a day.
Watch the full conversation
Full transcript
Taylor Dahlem
Welcome back to How I Deal, where we discuss past closed and lost deals, how they played out that way, and provide some useful or at least hopefully useful, sales tips that you can use in your deals today. My name is Taylor Dahlem, full cycle account executive, now turned content guy, and as always, joined by our sales brain here at Pickle, Junior Lartey. How are you doing, man?
Junior Lartey
Doing good. So, fun fact, I've had some account executives reach out because our podcast is a little bit unique in the aspect that we're really trying to get away from just being a prospecting podcast or a metrics podcast. We're just trying to expose deals end to end, from enterprise to min market SMB right. We know it's not perfect, so if you have feedback, find myself or Taylor on LinkedIn, drop us some feedback because we'd love to hear it.
Taylor Dahlem
Absolutely. Sales is a human experience. It's a story. It's a narrative that's told over time. It's not just, hey, how did you first get a hold of them? We're also interested in how did it close? So we're just tying all that together for everybody and we're certainly glad people are enjoying it. But a quick refresher if you've heard maybe a past episode or haven't heard us at all. Each conversation we chat through a past deal. We want to keep all names, places fictionalized or at least anonymized. And that way we can dive really deep. Understand? The first time an account executive or full cycle seller saw a prospect in their CRM or on a list or really anywhere, you first discover someone all the way to getting the DocuSign approved or wherever your deals are closed and moved to close one in your CRM.
Junior Lartey
Today we've got Nick Smith, who before cells, was a submarine nuclear technician in the US Navy and served on the USS Montpelier, which is obviously incredible enough. He then merged into consulting and selling and is currently creating funny motivational and helpful sales content on TikTok at Nick Reed Smith, and he is currently an AE at WorkSpan. Nick, you've got quite the story, my friend.
Nick Smith
I appreciate it, guys. I'm excited to be here.
Taylor Dahlem
Nick, give us some more insight into your role and more specifically, what problems you're solving at work.
Nick Smith
Span yeah, for sure. Well, I think the easiest way to explain WorkSpan is essentially we help to build a bridge between your CRM and also your partner CRM. Right? So for companies that are selling a lot through partnerships and ecosystems, we help to build the infrastructure that powers that.
Junior Lartey
So real quick, Nick, how often are you asked that question? What promises, WorkSpan solves?
Nick Smith
Probably all the time.
Junior Lartey
So everyone listening to know before, when we asked Nick this question, he pulled up this diagram that he wrote on a little whiteboard to paint a really clear picture. Nick, do you do that, like, in your actual demos or discoveries?
Nick Smith
It's more for networking conversations. I do that because I'm a very visual kind of a person. Right. And so yeah, I get the point of having like everybody says, hey, you should have your seven-second pitch or your thirty-second commercial. But for me what's more authentic is drawing a picture, like actually sitting down, drawing a picture for somebody and walking through it. It just feels more natural. To me.
Taylor Dahlem
That's the TikTok. Much more of a visual teacher and.
Junior Lartey
Educator, the content guy, the content creator. Well, I love that aspect, so thought I'd bring it up now. But Nick, ultimately what deal are you walking us through today?
Nick Smith
Yeah, so I'll actually walk through the first deal I closed here at WorkSpan.
Junior Lartey
Heck yeah. Sweet, very cool. Yeah. Tell us about the company that you sold into. Some specs around it, I suppose.
Nick Smith
Sure. Big ISV one thousand plus employees, very well known in the AWS, Microsoft and Google ecosystems. I mean, it was just a perfect fit right within our ICP, right in the strike zone. I got a list assigned to me. I'm very lucky. We have a real marketing team that actually does research and gives us lists of people to go out to. And so when I saw them I was like, oh, these guys are perfect.
Junior Lartey
Okay, so one thing that we're really trying to do is we're trying to help reps identify the difference between awareness research and prospecting. Awareness is like how you heard about this company. It sounds like for you it was a curated list from your marketing team that's ultimately like where you found them. But then research, that's what info you go out and find yourself before you ever reach out. And when you reach out, that's obviously prospecting. So awareness came from the marketing team. What research did you conduct here? What did you learn?
Nick Smith
Yeah, absolutely. So once I got basically got the list right, and then that was kind of my first indication of awareness. But then from there the additional research to your point took place where I'm actually looking at the AWS partner directory, the Microsoft Partner directory, I'm looking through LinkedIn, I'm looking at insights on zoom info and other places like that. I'm just trying to gather as much information as I possibly could and even looked at the LinkedIn profiles of all the different people who I thought would be decision-makers or stakeholders in this deal. And I took all of that information and it really helped me paint a very clear picture and it almost enriched that idea that I already had from the start, like, hey, this is a perfect fit running the ICP. And I saw lots of different triggers, lots of different things that were coming out in that research that then enabled me to personalize my outreach. Right. Because I could now say, hey, look, I know this about your company. I'm ninety-nine percent sure that you have this pain because everybody else I'm talking to in this situation? Who's talking about these things? This is the situation that they're going through. Is that relevant to you?
Junior Lartey
We've used that term on the podcast before, like, triggers. Try to find these triggers, try to find these events to help you recognize when to reach out. We haven't directly tied a trigger to a pain point where you say, because of this trigger, I reckon they have this very specific pain. In the past, it's been like, hey, you're hiring. So because you're hiring, you're likely just going through the emotions of this, but you're like, this trigger is this pain. And I think when you do some outreach, that probably helped quite a bit.
Nick Smith
It's huge. In fact, I don't think we've talked about this before, but literally, when I got the email, we ended up kind of doing a post-mortem after the deal. And he even told us, he's like, When I got your email, I get hundreds of Cold emails a day, but when I got your email, I was like, this is exactly what I need. He's like, I ignore most of them, but because you knew exactly what was going on in my life, like, you knew my pains, I knew I had to take the call. So that research, it was huge. That probably was one of the most important parts of the deal.
Taylor Dahlem
That's massive. And I think we talked about sales cadence always just being a hot topic on this podcast, but there's different ways to approach it. Call first, email, first LinkedIn, whatever. But as long as the message is right on point, it doesn't really matter where you're hitting them. Maybe it does based on where the answer is, but for the most part, as long as you're correcting your message in specific, that's what matters the most. And you mentioned, obviously, this email hit right on target, right in the strikes of the pain. I'm curious, could you give us a little more detail, like, specifically how you outlined that message or maybe what resonated the most?
Nick Smith
Yeah, so generally, kind of my framework for emails is you want to keep them painfully short, and you always start with it's all about you, like you being the customer. It's not about me at all. It's like, Show me. You know me. Right? Sam McKenna talks a lot about this, right? So it was pretty much a summarization of all the stuff I found out about them. Right? Like, hey, you guys are really well-known in this industry. I noticed you have this many deals with AWS. People who have that situation are currently dealing with these types of pains. Is that relevant to you? Like, literally, it's that short and simple, but it shows, like, okay, the fact that he knows we're in the AWS ecosystem, he knows the amount of deals that we've closed, partnered deals, that shows a level of research that you're not typically getting in just a form email. Right.
Taylor Dahlem
And you're doing it in a concise enough way that you're hitting the target, but also at the same time you're creating something interesting. Right?
Nick Smith
Yeah.
Taylor Dahlem
You could do a million bits of research, but if you throw it into four paragraphs in an email, I don't give a shit what you have to say or how well you can solve the problem I'm putting on the trash, but the fact, like you said, painfully short and just almost demanding attention with the specific language you're using is just a beautiful combination.
Junior Lartey
Before I pull up this other question, I just want to reiterate Sam McKenna. So the Show Me, you know, Me, that came from her, she is a great sales influencer, has really great sales content, does training. So for sure look up some of her methodology, if you so please. But at this point, okay, you've got the meeting booked. It's game on. Tell us about the discovery experience, what you learned that helped fuel the rest of this deal.
Nick Smith
Yeah, so this is actually a really quick discovery experience for me coming from in the past, I was working bigger services-type deals. I spent a lot more time in discovery here. It's a much more prescriptive approach. So it was basically just kind of following the Sandler pain funnel like we got on the call. First call was just with the main guy I had emailed, didn't have his whole team engaged quite yet. Just kind of said, well, hey, based on the email and your response, clearly you've got this pain. Just tell me a little bit more about that, okay? How long has this been going on? What have you tried to do to fix it? Kind of going through each of those steps in the process and building out a really clear understanding of what's going on in his world, what he is trying to achieve, and then even trying to quantify the pain. Right. Hear about how much the situation sucks, but what is it costing you as a business? What's it costing you at the personal level? Like, what goals are you not going to achieve if we don't fix this? And then being able to take that quantification of pain and say, okay, well, now we've got this really big problem. We're making it look even more clear how big the problem is. But now let's look at the payoffs. Right? So if we solve this problem, what are the additional things you're going to gain? Yeah, we're solving this big problem over here, but oh, you know what? Your team is actually going to get some additional time that they can spend on pushing more deals through the pipe or whatever else those payoffs are going to be.
Junior Lartey
Yeah. Nick, this sounds like something that they had just been living with. Like, this is just a pain they live with.
Nick Smith
Yeah. And that's pretty common. We don't really have a lot of at least at the time, we didn't have a lot of direct competitors. Pretty much the other options for people were to build their own integration, which is pretty time-consuming, or people were just throwing bodies at the problem. Right?
Junior Lartey
Yeah. So one thing that's really interesting is the trigger pain that you found in your initial research is literally just pain that they live with every day. It's not this huge initiative to like, oh, we have this massive we recognize this massive problem and need to fix it. It's just like, hey, that's kind of painful. Next email is interesting. And they tied the two together and then what your job as the seller to do is to help them recognize that living with this pain is actually costing them a lot more than they recognize. And being able to do that, I think, is the difference between getting this discovery to go from demo to close one and demo to close loss. Because a lot of times your prospects are living with this type of pain, but they're living with it. They don't recognize that, oh, my gosh, it's costing me so much, and it's more than just pain. So, I mean, kudos to you. You did a really great job leading them through. Like you mentioned, the Sandler pain funnel to recognize this is not livable pain. Like, what you're living in is actually misery. Let's fix it.
Nick Smith
Yeah. Just to build off of that really quick. In a lot of different sales jobs I've had, our biggest competition was do nothing. Right. Live with the pain. Because to your point, a lot of times people have that pain. It's kind of latent, and the easiest thing to do is just to kind of continue going through the motions and not address it.
Junior Lartey
We've talked about this before, but banish indecision. Banish it. Don't let them choose nothing. Make them choose something.
Taylor Dahlem
It's always easier to choose something.
Nick Smith
Love it.
Taylor Dahlem
And I think, Nick, you had mentioned before we started recording like this was your first, maybe not your first, but in this role, selling a product over a service.
Junior Lartey
Is that correct?
Taylor Dahlem
And that's kind of where maybe that changed the approach a little bit. And this will dive into the next step here where Gap Selling. We're big fans of Keenan and his work, but ultimately he talks about limiting how much you demo and just really sticking to a small amount of features, five, six, max. And so, like we preempted here, this is the first time you're walking through a product, an actual pain that you solve via product, not just a service. So you start with a big priority or main reason, whatever you dug up in discovery. But a lot of times, people can get lost along the way. Maybe there's too much, too many details and you get too in the weeds or you just didn't do enough. And like we were talking about, maybe indecision is now you're going to be your biggest enemy because, oh, it hasn't killed us yet. We can keep living with it. So I'm curious, with a short discovery, demoing had to be a much, I guess, more targeted, specific process because it's kind of your last swing at the back. Hopefully you did good enough discovery. So how did that demo experience go and ultimately, how do you keep that process organized?
Nick Smith
Absolutely great points. And so the second meeting was really that more in-depth demo and it was kind of understanding who are all of the personas that are going to be involved? Right? So I already was talking to the business decision maker, but he had other people that he needed to get involved, other stakeholders like, hey, the salesforce administrator rev ups, okay, other people in his sales team. So all these other people have their own fears and their own things, and many of them could veto the deal. Right. So trying to understand ahead of time, what is it that they're going to be concerned about, like, what are they going to be worried about? And then try and tailor that demo to them. So, for example, the partner alliance manager, he's kind of the chief decision-maker on the business side of things. For him, it's going to be about attribution and deal registration and about reducing amount of time that he needs to spend actually maintaining the CRM system. But for the salesforce administrator, they're going to be concerned about, do I have to, like, physically change the way I'm doing all of my deals, all my opportunity objects? That's going to be way too big of a lift. We're not going to do that. So how do I reduce that pain point? How do I show them? Okay, hey, look, now it's not that hard. We're not going to adjust any of this. We're just going to add like, these two little extra buttons into your environment. We're going to add in this custom opportunity object, the referral object. Here's how you map fields. Here's how you map values. So understanding that's the things that they're worried about. And then for the sales team, right, okay. They don't want to have to learn a whole new platform. So how can I show them within their current workflow? Hey, look, it's really easy. All you have to do right, within your current way that you're creating a deal. I'm just adding these two little buttons over here and then bing, bamboo, you're ready to submit a referral. Right? So trying to understand what each of those personas cares about and then tailor that demo to what they need, I.
Junior Lartey
Think it's fair to say you clearly understand those personas. Like, I myself, I'm in none of those rules and I'm comfortable moving forward at this point. But one thing that I love about this too, is this deal. There's no executive. There are buyers that are not executives. I have deals like that. Lots of sales reps have deals like that. And so in this case, you're treating the alliance manager as your decision-maker. Right. You mentioned this is the business decision maker and I think you're treating this person the same way that you would an executive. And I think that is key to getting all the other parties involved, all the other parties to the table. And then when you're there, obviously you do a great job like tailoring all of their roles, understanding their personas. So one of my favorite parts of the podcast are the objections. This is where I personally learned the most. This is where I learn like the tact of selling. We learn through objections. So sometimes the what to do, sometimes the what not to do. Most of the time it happens in hindsight. But were there any major barriers or objections in this deal that you had to overcome?
Nick Smith
Yeah, well, all of the ones that you could predict. And I think this is actually even something that we should talk about a little bit because typically, if you think about it, what are the common objections that always come up? There are always going to be something around pricing. There's going to be something around legal, procurement, security. So I'm very lucky here at work, Span, that we have a great team, great sales leadership. So we already had mapped out what we thought the objections were going to be ahead of time, and we already had responses ready to go for those. So we could even bring them up prior to them coming up. But then even when they do come up, it's like, hey, we know how we are going to handle those objections. So yeah, those all came up, but we kind of went through the motions and tackled all of those and went pretty well. And then two, I think one of the things that I don't know if I would call this an objection, but it was a barrier was I ended up getting ghosted through the deal, right? And sometimes you're like, oh, what did I do? Did I do something wrong? Or is he just really busy? And so I even remember in that situation, it's like, okay, well, I shot an email, I tried to call, I sent him a LinkedIn, what am I going to do here? I ended up even picking up my phone and just texting him. And normally I'm not a fan of just sending out a text without getting permission first, but I even sent out the text with an apology. It's like my first line, I'm sorry for texting you without your permission, but I've tried all these other approaches and I don't know what else to do, and then fired back and it's like, hey man, text is great. And then where it became like best buds and we're texting everybody.
Taylor Dahlem
It's got to be extremely to me, like you said, you took a risk, you shot a message, but at this point and probably for the listeners. We've gone through a few meetings at this point. I would assume consent has been achieved at least a little more than just cold texting right after your research stage. So it seems like that was a risk, but not a huge risk. But the payoff was huge, obviously.
Junior Lartey
Maybe we should just establish like a precedent. If you've had two meetings with somebody, you should probably feel comfortable texting them.
Taylor Dahlem
Any form of communication.
Junior Lartey
Yeah. Getting outside of what you're typically comfortable with, which is probably email. I imagine most reps are sticking to email and I guess this is going into our next little bit. But Nick, obviously texting was big to rekindle the conversation, but understanding, hey, they're probably going to bring up legal, they're probably going to bring up procurement, getting ahead of those things, talking about them before they do. In hindsight, obviously very valuable. Knowing that these things are going to come up can be very helpful in the deal without extending the timeline of conversations and trying to manage all the moving pieces here.
Nick Smith
Totally agree. I didn't hear a question there.
Junior Lartey
There is no question. I started to ramble.
Taylor Dahlem
It's less of a question, more of a lesson where if you know your persona well enough, if you know your buyer well enough, you understand not only what the pains they have and what questions might come up, but more importantly, where is this deal going to fall apart? If you understand that and then have the gumption to bring it up before they do, like, hey, here's probably where you're going to tell me no. Or here's where this is going to fall apart. I think it does something in the psychology side of sales where it creates a little more trust. Right. It shows you a true consultant because you're like, hey, here's all the reasons you're going to say no to me. Let's just air it out and answer these questions before they put the kibosh on. We're three months in and we didn't even cover this one hang-up that we're going to get at that point; a deal falls apart.
Nick Smith
Yeah. I hate it when people overpromise and underdeliver. Right. And so to your point, trust is everything. And so when you can be upfront and be a little bit vulnerable and say, hey, here's where things typically get tied up. Here's some of the things that we're not perfect at. Here's a few things that we've gotten called out on before and we're working on, and here's our plan for fixing it. I think that goes a long way toward establishing trust versus saying, oh, no, everything's perfect. Nothing could go wrong. No one's going to believe that.
Junior Lartey
Yeah. It's just not true. It's just not true. Nick, give us a recap of the timeline and we're going to start calling this deal management, like how you managed communication throughout this whole deal. Give us some perspective there.
Nick Smith
Yeah. So it was a three-meeting deal, right. So first that initial discovery, second meeting, broader demo with the rest of the team. Meeting three was really more of like a recap, getting more into, like, answering some of those technical questions, getting to that verbal commitment. And then from there, most of the communication happens asynchronously it was two months start to finish from that initial outreach to a closed one deal. And a good part of that was just the back end, getting all the paperwork sorted out. Right. Getting through procurement, getting through legal, getting through infosec. And a lot of that communication happens through text messages and sending emails back and forth at the end of it.
Junior Lartey
How many texts do you think you exchanged just in like the two-month process?
Nick Smith
Oh, gosh, I don't even know that I could put a number on it.
Junior Lartey
Okay, let me ask a better question. Go ahead.
Nick Smith
Well, it's funny because we tested a lot about the business side of it, but then it ended up turning into more of like a friendly conversation.
Junior Lartey
Yes, that was going to be. Let me ask you a better question. Did texting go from business to personal? Because when you bridge that gap, that is a different level of selling and commitment.
Nick Smith
Absolutely. I feel like the texting really advanced the relationship. It even got to the point this is going to sound really unprofessional. You're even like, sending memes back and.
Taylor Dahlem
Forth, not professional at all.
Nick Smith
And so it was getting to that point where we're talking about the kind of whiskey that he likes and all that kind of stuff. And so that was great because the relationship part was there, but then there was also the business part attached to it as well. So it was, I don't know, hundreds of texts.
Junior Lartey
Yeah. Taking the deal management from text to personal life, I think is really cool to be able to do that. And we're talking about three meetings. Someone might look at that. I'm in the SouthWorld, I have three meeting deals all the time, but someone may look at that and be like, only three meetings? That's not a lot of communication. Well, there was a ton of text exchange, and in that you get exposure to things that you wouldn't typically get to even if you had ten business meetings with no backend texting. So huge there. Let's wrap up here. What are three things that any sales pro can do today to inch closer, to close one on some of the deals that they're working?
Nick Smith
Yeah. One, get in front of the timelines, really understand them if there's certain things that you can run in parallel instead of sequential, try and run them in parallel as quickly as you possibly can. Right. In my case, if I could have sped up that procurement process and brought it up earlier, I could have saved myself a lot of time and probably even close this within a month instead of two months. Right. You don't have to check every personal box to feel comfortable. This is my first time selling a product instead of a service. So I was used to running very thorough discovery meetings. Like having almost like a full questionnaire of different things filled out where I understood all the different pain points of all the different decision-makers and all their motivations. I didn't have that in this case. It was much more prescriptive, shorter timeline, and that's okay, I didn't have to have all of that. The deal is still closed. And then three, I would say find ways to break through and communicate, right? If one method that you're trying isn't working, don't just send one hundred email. Try sending a LinkedIn, try sending a text message, try sending a voice memo. There's many different communication mediums. In this particular deal, text worked out, but I've had it happen the opposite to where texting wasn't working. And then, hey, I caught someone on LinkedIn and I was able to catch them in the comments section of someone's post or sending them a video through, like Vidyard or actually, you can send videos through LinkedIn Messenger. There's a million different ways to communicate. People keep trying things until you finally find something that works.
Taylor Dahlem
Like you said, send some memes.I think memes are the new golf course of the business world. Just where deals get done.
Nick Smith
Actually, I'm going a little off-script here, but the nice thing about making I make a bunch of TikTok's. I use that as a way to break through the noise sometimes.
Junior Lartey
Perfect.
Nick Smith
I've sent videos, I've sent stuff like that out to people and I've had people, they respond to it because they're doing that right.
Taylor Dahlem
Every barrier breaks through all the noise that happens there. But I love it. We infuse humor all the time in our sales. I think that's a great tip.
Junior Lartey
I've been a new rep before and I would just follow up email after email after email, and then my VP of sales would be like, where is this? I'm like, well, they're not responding to my emails. Well, you got a phone, you idiot. You got LinkedIn, you dummy. So there's that for you. It's not that you're stupid. We just got to start thinking about those things. But Nick, this was a great conversation, a fantastic deal to walk through. The texting aspect was so cool to hear about. Go connect with Nick Smith on LinkedIn. Go follow his TikTok. If you have TikTok at Nick ReedSmith. And again, really great to have you.
Nick Smith
Thanks, guys. This is a blast. I love everything that you're doing and I can't wait to see more episodes.
Taylor Dahlem
Absolutely. As always, a true pleasure to talk.
Junior Lartey
With a real full circle seller and.
Taylor Dahlem
Account executive that's in the trenches with us. So always refreshing. And just like that, another episode of how ideal is in the. Books. If you tuned in via Spotify, Apple, wherever you listen to your podcast, please feel free to leave a comment rate of three, four, five stars, even if you truly enjoy it and give us some feedback. As Junior said at the top of the episode, we thrive on that and want to make this truly engaged agent and a great experience for everybody listening. So, with that being said, thanks again, Nick, and we will see everyone next time.
