BEYOND QUOTA PODCAST

Episode 25: Will Aitken

The man with a literal Scratchpad tattoo, Will Aitken, joins Beyond Quota with Pouyan and Ross. Will leaves it all out on the field in this interview as he reveals his path from sales to “marketing” and how he finds the fine line between engaging and educational content for salespeople.

Transcript

Will Aitken  
And it feeds you ideas. Right? So like that video I mentioned, what if other departments worked in sales? It came because I watched you, Ross and Ben chatting about like, hey, should should other departments have a target over their head? That's from this podcast. Yeah, exactly. Yeah. Yeah. Yeah, I listen to this podcast.


Ross Pomerantz  
See Pouyan, value created.


Pouyan Salehi  
My work is done. Thank you. I'm gonna go get buzzed now. Well, you inspired me. I'll be honest, I still don't fully believe here. But hey, we'll take your word for it.


***Beyond Quota Intro***

Pouyan Salehi  

We're back. I'm Pouyan from Scratchpad here with Corp, again.

Ross Pomerantz  
Good to see you as well.


Pouyan Salehi  
I still every time. Excited for today for another episode of beyond quota. We've got Will Aitken with us. Did I pronounce that right.


Will Aitken  
Yeah, most people pronounce it Atkins. So I thank you. All right.


Pouyan Salehi  
Well, we've got Will Aitken with us. And apart from having an awesome background that we'll get into on how it's actually been controversial. Maybe one or two cases, has a really interesting story around sales and content, and maybe even back to sales. So that's probably a first that I've heard.


Ross Pomerantz  
Give us the quick. I don't know one minute elevator spiel on where you were, where you are


Will Aitken  
Born in 1994, in the city of Milton Keynes, UK. Basically, I was in b2b sales for a little while that I started making little Tik toks of selling software to sales leaders, the personal brand was helping me out but it got the attention of my now boss Tyler's side of Vidyard. So he brought me on as a founding member of the Sales Feed team. And now I've taken I've done the dark switch from sales to marketing. Which Ross you know all about? Right. I've heard about it. So yeah, that's the quick background. So right now full time, full time content creator on behalf of sales.


Pouyan Salehi  
I haven't heard that much in terms of the content that's out there. Right. There's, it feels like, oh, I shouldn't say this. Maybe I will. It's like everyone's creating content for salespeople. Now, as I sit in front of two sales creators.


Ross Pomerantz  
Everyone's LinkedIn these days, yeah, totally.


Pouyan Salehi  
Sales influencers. Maybe I've just missed it. But right, but everything's on like, oh, you should you know, the question you should ask when you start the follow up email template, you should send, have you seen anyone actually take a deliberate accent approach, because I, hey, go put yourself in a training program for four weeks, learn how to do this accent, and then start cold calling.


Will Aitken  
I sit next to a guy. So I went from sales to recruitment. And then I recruited salespeople, and that's how I knew I wanted to work in SaaS, because they'd been paid really well. I used to sit next to this guy, and he was British, but he had Indian parents and he actually went to training to sound less like from his because he actually found that had a direct result on his conversions. Now, I don't think I think that's not a fair comparison. But that that is a thing that people will do. It's a shame. I've definitely heard a lot of people had to godown that route.


Ross Pomerantz  
I mean, there is implicit bias, explicit bias racism, I mean, it's all of it right? Like all you're trying to do is it's all psychology and either if there was like a single opening line that was the silver bullet whoever comes up with that is a Nobel Prize winning billionaire at that point, because they're closing every deal they're they're absolutely killing it. So you know, that's where I like personally struggle on the whole like, sales content sales like train lead people, like Dude, give us more like serious stuff. And I'm curious on your thoughts about this, because you do much more. I mean, you obviously do the comedy stuff, which is great. But you also tend to do a little bit more actionable, like, sales advice, true sales advice, where I tend to, like shy away from that because I don't I don't feel like there is I know what works for me, but it's not going to work for most other people.


Will Aitken  
Like what you just said that Ross as well. Like if there was one silver bullet, I'd hope it wouldn't tell everyone what it is because then everyone would go ruin it. Like, there's obvious being a silver bullet when everyone's doing it. It's no longer a pattern interrupt. It just stops being that when everyone's doing it. It's no longer special. Now, for me making extra content Yeah, kind of I still feel like an impostor make like I mentioned I now work in marketing. I haven't closed I have recently but I hadn't closed the deal for nine months and I was still posting about sales three months ago. Right. And I the way I look at it is you don't have to take everything you read as gospel mine and I like to pick and choose so I like you know Jed Jed Molly's point on how to do competitors, but I like No, John Salix Coco opener. It's funny, so I like to look at it like that. It's kind of like a pick and mix stuff that everything that someone says is gospel. I 100% miss like the people on Tik Tok they let you know when you miss that. Yeah, then they're ruthless. So like it's like it's okay. And like I think that's just part of it. Is that when you when you're out there looking at this advice You just find stuff that works for you. And you take that, and I found the best sell. It's kind of taken a bit of everywhere. They're not like, Oh, I love David Sandler, I do everything you ever thought that stuff came out like 30 years ago now. So they're probably doing a little bit of that. A little bit of Kenan or whatever. And I think that's, that's the best sellers take it. The Newbies probably are taking a lot of stuff, gospel, and oh, we'll set it so I have to do it. Right. So I think there's there's some nuances that but that's how I look at it.


Pouyan Salehi  
How did you get into creating content in the first place? Tell us about that.


Will Aitken  
I've always liked loved attention to be fair, all right. It was probably naturally gonna happen always wanted to be a YouTuber, like, like gaming or whatever. I don't know what it is. I started like three different YouTube channels. And now I use them with like nine videos. When I think I made a post in like January of last year, so it wasn't that long ago. And Sarah brazier just closed the deal with my company proposal. And I've kind of given up and given her the inside scoop, because I followed her and I was like, Yeah, this is what's happening with ops right now. Think we were churning from chorus and go into Gong. So I was kind of given her like what objections were coming up internally. And then I made a post and she liked it. And that obviously, when you when you get people like that, and like it get kind of got a bit of momentum behind it. And I saw some direct kickback onto my pipeline from that. People requesting demos from me, people mentioning it during our calls when I was getting back on calls with customers as an AE. So then I was like, I should do more of this. And then I posted a meme about let's go on Tik Tok. When it goes trade deal. I said, you get this. And you get this. And I was like, should it should I start making sales tik toks? And was like, Yeah, do it. And then I just did that every day. And it became a bit of a hobby. And then it became this.


Pouyan Salehi  
How do you go about the content you put out there? Like how do you think about that? Is it planned? Is it just whatever comes to mind?


Will Aitken  
Sometimes I think of an idea. And I'll just write down. I've like got more ideas than I can action right now. So like, it's more so like most of it's just in the moment, I think we're so funny. I'm like, that's funny to make, like probably the most successful video I've had the day was like, what if other departments got treated like sales, I was sick that day, I woke up feeling horrible. But I had this idea of like, right before I went to bed and I woke up, I need to make that right now. And then it went ahead and came like LinkedIn is obviously a little bit harder to go viral on but became the biggest part of LinkedIn. And that's normally how everything goes. It's kind of like what we're going to make today.


Ross Pomerantz  
It's always the quickest stuff that's the best. It's always the stuff that comes in a moment of inspiration, like you can sit down there and grind out a bunch of tiktoks or like ideas. And then like, you'll find they're uninspired and kind of contrived and like, they just don't hit the same. At least on tik tok though, you can like put out a volume, they want you to put out a volume of content. If something bombs, like no one sees it, it's not like people go to your feed and are like combing through your feed. It's like they either get presented it or they don't. And like I think I used to be I used to hard avoid all other content. Like I didn't want to watch anybody else's content cuz I didn't want to be either accused or influenced or like, inspired as a bad choice of word here, but inspired by somebody else's thing to do something similar, because I always was like, I'll come up with something original, I wanted to like be totally different. And then it got to a point I was like, what what am I why would I do that? Why wouldn't I just like, with with Tik Tok, like originality, for better or worse has kind of gone away. And it's like, you can repurpose, like they've created kind of templates and like repurpose, you can repurpose things for your own voice and like, it doesn't matter. For again, for better or worse, like old school people will be like, That's bullshit, like, new stuff, like you need to do blah, blah, blah, blah. But now I'm kind of like, you know, this is the game now. And this is how you got to play and like, not now I also sit there and watch a bunch of content, like, much more like


Will Aitken  
and it feeds you ideas, right? So like that video I mentioned, what if other departments worked in sales? It came because I watched you Ross and Ben chatting about like, hey, should should other departments have a target over their head? Right? And I was like, oh my god, wouldn't it be a funny idea of everyone had and then one of the comments was like, Yeah, you know, the marketer on a pip if, if she doesn't get 100,000 likes in the next Instagram post, and then I saw that and I was like, Oh, that tapered off, right. So it's not necessarily copying, but it's like looking for inspiration in places. All right. That's from this everything. Yeah, exactly. Yeah. Yeah. Yeah, I listen to this podcast.


Ross Pomerantz  
See Pouyan, value, value created. If you ever do


Pouyan Salehi  
My work is done. Thank you. I'm gonna go get buzzed. Now. Will you inspired me?


Ross Pomerantz  
What do you think the future of like content creation in b2b is like, do you think, you know, the every reputable b2b company at some point will have a I know you hate the term sort of why like evangelist or like a chief content creator or a content machine of some sort that is outside of that is not traditional marketing.


Will Aitken  
I think one in every category, at least. I think I think the issue the issue companies have is because they got VC funding. And they got these investors who were like, give us metrics show us where the money is coming from, is that this is a really hard thing to justify. And it's not cheap to hire us. Even if you're let's say, let's say you're an HR tech company, right? It's so easy for us to get trapped in this like revenue tax space, because we sell it and it's easy for a salesperson to become a marketer. There is potential for someone who's in HR out to go join a marketing team for our HR tech company. Right? That's that's a potential as well, we know you're thinking about those things. The issue is the metrics attached to this type of role are likes and comments it is so hard to prove attribution of this kind of thing, that you do really need a forward thinking founder, and VC and board really behind it to actually make it happen. And most companies just don't have that. So I think at least one in every category will will jump in on this and make a ton of money from it. Because I do know that we've seen some people were like, meant it's the soft stuff that you can't, it's hard to measure. But when you put in your gong thing, like, pick up for the word Will Aitken being said out loud, and you start to see that in sales conversations that you're having. Well, at that point, like it's like the light bulbs start going off in the light. Right? Okay, this is actually, it's feeding in somewhere, we're just having a hard time tracking it. But that's, that's the biggest challenge. So maybe if tracking gets better on that side of things, if social listening and all that improves, then it will become more common. For the time being, I think it's still a risky event, especially now. It's a risky venture for a lot of companies,


Ross Pomerantz  
like content creation needs to be more authentic and more raw and more truthful. And a lot of companies are scared of those truths. And like customers, seeing those truths, or hearing kind of how the other side thinks, or even how both sides think I think like, you know, the reason, like doing this stuff for salespeople is probably the easiest isn't the right word, but the best fit for like, consumers of like comedy towards their profession and so forth. Whereas like, I mean, you see all these cybersecurity guys who are just like freaking out on LinkedIn about God knows what like, what aside like a CISO, like a security analyst, like content look like maybe I'm sure there's something Oh, yeah.


Will Aitken  
But on LinkedIn, because they're trying to hide from us and horrible sales messages. But to be fair opinion, like you, I'd like to throw the question about the new because you kind of got a similar thing going on with, you know, Ross, and Ben does a lot of content as well.


Pouyan Salehi  
I think you're right, and trying to find good old ROI in this journey is hard, or ROI, I should say. Good old ROI. Think you have to change your thinking on it. And I actually think it's more of a foundational belief of Do you believe that good storytelling will have an impact? In some way, shape or form on what you do? And I certainly do, I actually think storytelling is one of the most important skill sets to learn whether you're going into sales to marketing, definitely, if you're going into starting anything, right, especially a company, because all you're doing is telling stories, right? When you're trying to raise your first round how your first folks it's all story, you don't maybe you have a an early version of a product, right? So I come from that school of thought and that belief that stories matter. I believe people consume and remember stories a lot better than anything else. So for me, it's actually a lot easier to, like, lean into this and say, Listen, I don't know exactly what metrics we're going to track or what necessarily the outcome will be. I just fundamentally believe that this is an important thing to do. And in in parallel to that, though, I think you also have to believe that it's a creative endeavor versus a scientific endeavor. Because to your point, like you call it before, how many misses do you have before you have one that finally lands? And how many times do you go through something and you learn, and then your mental model improves, and you start saying, okay, like, I started building this intuition that this type of content is going to work better than that one


Ross Pomerantz  
depends on the type of company you're running to, like, you know, when you're using doing kind of a plg, like when you're in user early, early on for scratch, but obviously, it's changed now where like leadership and Reb ops are like very much involved in this. But like in the OG most basic forms, like we're trying to get in front of sales reps, and like, sales reps are watching content, they're on Tik Tok. They're on Instagram, like they're out there. And like, I believe, I mean, obviously, I believe the same thing around storytelling. And if you can create some sort of positive association, some positive feeling, in conjunction with your brand, then that it can only be net positive, and it may not manifest for years, they may not, you know, manifest in the way that we think it will at all, but who knows, like, you know, where that story and how far it can reach and influence people.


Pouyan Salehi  
But back to what you were saying, Will, on the approach, I think you have to have at the highest levels leadership on into the creative process. And that recognize that you know, what, sometimes not sometimes most of the times are misses, and sometimes you have to test the boundaries to know that okay, like that one a little bit far. We need to bring it back. Without that, that I think it's hard.


Will Aitken  
The one that probably because it was at that line, right? That line is always a place where they can do really well. It's just about knowing how far you can go on it.


Pouyan Salehi  
But I wonder if you could take this outside the plg movement to it and just start like, why not start creating content? I mean, go to the extreme. Why not start creating content for other CEOs right you Talk about going high and wide in a deal, right? You certainly want to multithread up but like to that extreme


Ross Pomerantz  
CEO tam issue. But that is true but a valuable enterprise type


Pouyan Salehi  
deal to tam issue from what the TAM issue from maybe the number of them. Tam is you could actually be huge from


Ross Pomerantz  
dollar value and retired. Agree, Agree. Yeah,


Pouyan Salehi  
that's a silver bullet right there? Well, you start getting, you start getting the CEO to say, I want to buy this from every target company you have, you'll probably probably do well on your quota.


Ross Pomerantz  
The problem is not enough CEOs are watching content.


Will Aitken  
That's the thing is when the reach relies on like, it scales, right? The reason why it's really, it's easy to make content for the sales reps, because there's hundreds of 1000s of sales reps, there's probably only 10s of 1000s of VPs of sales, so becomes smaller and smaller. And the way you get them to see the content is like because it gets liked by one person, which shows it to more people. So you'd have to find like an a core network, shake some hands and get them to like it. So their friends will see it right. There's probably some thoughts for that. I'm gonna go shake some hands at SaaStr and then do it.


Pouyan Salehi  
Or if it's valuable enough, just go direct it,


Ross Pomerantz  
we'll see it will be there, and it's


Will Aitken  
straight to him. That's a really good point as well. People don't do that they wait to play about content, you send me a funny video. I'm gonna be like, thank you. That was awesome, right?


Ross Pomerantz  
Well, that's what Ben and I are gonna be we're gonna be cold calling CEOs to watch Sales are Dope, when that comes out. Are you a big part of our campaign? Yeah, we're Ben and I are gonna be on the phone, just calling sales VPs and CEOs and be like, You need to watch the show.


Will Aitken  
You'll get some great content out of that. Yeah. Yeah.


Pouyan Salehi  
I have a feeling. I'm on that list of not being called that and be like, Hey, Pouyan. Yeah, and we need some extra bandwidth here. So can you join in and start cold calling with us?


Ross Pomerantz  
Yeah, we're gonna need some executive leadership here. Lead from the front. Maybe hop on some of these calls for us.


Pouyan Salehi  
Let's get our engineering team involved. I think that would be fun to start getting


Ross Pomerantz  
That would be actually hilarious videos. Engineers cold calling to watch the show. And have them cold call about that. There you go. There's uh, oh, God, I feel them cringing.


Will Aitken  
Cold call. Yeah, yeah. Make marketing work. And Ross sorry. All you really


Ross Pomerantz  
Okay. So I mean, first of all, I'm a consultant.


Will Aitken  
I'd be curious. If you could someone who's like, hey, it's Pouyan on the CEO of Scratchpad. You started the call like that? I'd be curious. Because I always used to when I was a little excuse making cold caller, I'd be like, Oh, it's easy for you because you can tell you're the sales manager. I always thought my leaders had like a, an extra, an extra card in their pocket because they could say, Hey, I'm the VP of sales. I wonder if there'd be any noticeable difference?


Ross Pomerantz  
I think there's definitely a difference. Like I think if you're on par with someone like he probably on calls the CEO, they're much more likely to listen as like an equal and peer, whereas like every, you know, as much as sales nats at the bottom, just a bunch of ants crawling around just looking for scraps. You know, they know.


Pouyan Salehi  
Yes. All right. Well, well. So we're getting up on time. Maybe let's let's just ask. I heard you want to get back into sales.


Ross Pomerantz  
Who told you that?


Pouyan Salehi  
A little bird? Yeah, a little birdie. That flew by but what what is that? Correct? And if so, that's an interesting one because usually we talk to folks that have found their way out they stumbled into it somehow couldn't be happier. But yeah, the other way out, but you you know.


Will Aitken  
I'm selling stuff right now. But but not crazy active. And what what I'm doing is I'm trying to I'm trying to sell budgets, so I can spend more money on the stuff I'm making, basically. And we figured out the best way to increase my budget of how much good content I can make and I've got the camera but you know, get that take me places like to know San Francisco and whatnot. To get that I'm going to need to find that somewhere we want so I'm starting to sell sponsorships for Sales Feed to reinvest back in the brand. And ideally bring that value straight back vendor. We're getting a lot of eyes on us right now. So I'm basically having some conversations like those. So once I got two three so far, but two of them a little ones, and one of them was okay. sighs So that's what I'm doing now. And it feels good because I feel like less of an imposter when I'm talking about sales again, right?


Ross Pomerantz  
That's definitely the hardest part about doing sales content when you're not on the floor every day. Can 1,000,000% relate to that and like damn, I get mad at Tim I turned into the VP who doesn't know what's what anymore. You know, it's been 13 years I feel I feel that happening. I hate it. That's why


Will Aitken  
You have been going to make those cold calls.


Pouyan Salehi  
Anytime. Anytime. You just want to get back into it and you feel like you know, this is a day to start making some cold calls. We we run that plg motion, we've got the leads, you can throw them over for you anytime pick up the phone.


Ross Pomerantz  
Send me a couple of CEOs really just let me start at the top and we work with the best leads.


Will Aitken  
You're gonna you're gonna open with me it's Corp Bro. Like that's how you got to open though.


Ross Pomerantz  
Sup Johnny. It's Corp Bro. How you doing, man?


Pouyan Salehi  
So, Will. Two questions. What is your what's your recovery song? First, you're in Australia. You get you just get laid into


Ross Pomerantz  
A bomb on Yeah, like five times. It's not funny anymore. It was funny the first four times.


Will Aitken  
I'd probably go down some T Swizzle


Ross Pomerantz  
One. Okay, He sweat Taylor, yeah. Familiar.


Will Aitken  
Freezing out of Nashville. And for the song of hers, I'd probably go for love story or maybe even like teardrops on my guitar or whitehorse, one of those.


Pouyan Salehi  
So what's your hype song? Yeah.


Will Aitken  
So you gotta go. I'm either going down AC DC, thunderstruck, or x go give yeah.


Ross Pomerantz  
Well, and last but not least, we'll please. This is the time to be shameless. Self promote. Where can people find you? Where should they look for you? If they want to reach you? What's the best way to do it?


Will Aitken  
Yeah, if you want to contribute to the Sales Feed budget, then hit me up on LinkedIn. That's where I'm most active, probably. Sales Feed. Will Aitken. I'm on Tik Tok on LinkedIn for the most part, as the best places to reach me. And yeah, you'll know what to expect when you get there. It's kind of like, knockoff Ross, in its own way.


Ross Pomerantz  
Not it's much it's more


Will Aitken  
Intentionally knockoff Ross. It's gonna like, it's a different thing, but


Ross Pomerantz  
It's also the accent. So therefore, taken more seriously,

You take it far more seriously, you know, far more credibility.


Pouyan Salehi  
Well, thanks for joining us.