Episode #99 The Hottest Takes Guests Have Had Over the Years on A.I., GTM, and More...

From letting go of 40% of your team to sending friendship bracelets to CROs, this supercut of the hottest takes from Bridge the Gap Podcast over the years dives deep into the messy middle of building, selling, and scaling in 2025.

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Transcript

This is Bridge the Gap powered by Revenue Reimagined, the podcast where we dive into all things revenue. Each episode, we bring you the top founders and go-to-market leaders to challenge how you think about growth and help you bridge your biggest go-to-market gaps. I'm Adam Jay. And I'm Dale Zwizinski. 

As always, thanks for hanging with us. There's a million ways you can be spending your time and we're grateful for you choosing to spend it with us. Be sure to check out our newsletter if you want the show notes and tactical advice on how to bridge your GTM Gaps. Let's get to it. 

So are any jobs safe? Like is there any job that's truly safe from AI? I mean, if you were to force a ride, yeah, electricians and plumbers. 

And if you're in our world. And if you're building an AI product, you're probably safe. 

For now. Yeah. Until the AI product builds itself. Well, look, I think all jobs are safe. Adam, I think the question is, is what people in those jobs are safe? And I've said this before and I've said it since 2017 when I saw the first artificial intelligence email that freaked me the fuck out. Because it was better than I could have written in. It was faster than I could have written in. And this was 2017? 

2017. And I've been preaching, Jeff, that the average sales rep, it's not death of the sales rep, it's death of the average sales rep. I think AI is going to make good sales reps great. Great sales reps incredibly valuable. And average sales reps are relevant. And I think that's going to do 

it across the board in every industry. 

So I think nowadays, honestly, this assumption that you got to ship fast and iterate fast, it might be going away. It might be in a way where it's like you have to build a really good product so then you can get people to stick with it. I think that we're heading back in that direction where it's like less of ship fast, iterate fast, and it's more of like, let's button it up, let's polish it. Like don't take forever to ship, right? But like, I kind of think that. 

Like good enough is not good enough anymore. It's almost like in the go-to-market space, it's shifting so quickly. 

Alina, one of the things that I think a lot of founders struggle with is that balance for growth versus sustainability, right? Like in a startup world, it's like, we've got to grow fast. We've got to get the revenue. 

We've got to go hire 187 people. And all of these things that you have to do to grow. But at the same time, you have to be sustainable and nimble and agile. Talk to us like, is there a single or maybe one or two like really hard choices where you've had to manage that growth versus sustainability challenge? 

I was lucky enough to be in both stages of that. We were both bootstrapped and we were both thrown cash out at some point with the goal to grow as fast as possible. And I saw the benefit of both. 

I don't think enough people realize how important data is across all aspects of your business. It's not just, oh, I want to look at Salesforce or HubSpot and understand who my customer is and know their address and who the point of contact is. People don't realize the effect everything you're talking about, right? How do we find the right people, sell to the right people, convert the right people, convert more of the right people at the right time and the right place for the right amount? It's not just make my Salesforce look pretty. I think sadly, John, and tell me if I'm wrong, most people when they think data, they think, oh, like, do we have the right contact like in Salesforce and you know, are the fields set up properly? Like, that's not data. Eric, working with founders, how do you have the conversation of this is going to take time and time isn't seven days? 

Yeah, before working with founders, man, I had a full head of hair. Let's put it that way. And I mean that in the utmost respect, right? Adam, you can kind of test this. But let me just say what it comes down to is the visionary practice, right? We can give them the tangible. It's all day long. 

Start with what is the best message that you could send by hand? If you could spend on Adam, if you could spend on the amount of time researching on the web and writing one message to one customer, what is the message that you would write that they would pay to receive and then you can reverse backwards into how you turn that into a system? I really believe a process over prompts is like one of my more convictions. And specifically as you interact with AI, that you are the guide, not the river. And so you need to have insights on your customers to be able to help guide these large language models to say this is exactly what I'm looking for. And then they will perform beautifully for you. But you have to have a nuanced understanding with customers. 

But it's funny. I have to go. I don't know if you can look, but if you think about it, it is true. Even when we talk to one another, I'll use an example. 

We're going pretty heavy on AI right now and Dale's much smarter at AI than I am. And go research it as one thing versus here is this video. Go to this timestamp that tells you exactly what I want you to see. 

That's going to help you understand it from my coding side of brain that Dale has, but I don't. He'll validate this. I messaged him this morning. I'm like, dude, thank you for fucking sending me that. That is exactly what I needed. And now I totally get what we want to do. 

People that you would do anything to see play again or watch, but the audience that was involved and interested in soccer aid was mainly there for this influencer, like 27 year old influencer who had built a soccer community because they were like, this is the guy we want to see play. We've been watching his journey. Right. And so that just speaks so much to how much more relatable and relevant that creator, like the creator economy is because people are seeing the journey of people. 

Yeah, those days are long gone, man. But if I could generate a million dollars in business for somebody, and they pay me, I don't know, 10% on that, the company cost 100 grand. They didn't have to manage me. They didn't have to give me a computer. Like I said, they don't have to deal with my insurance stuff, my medical, nothing. 

They don't have to deal with me at all other than just like what they want to deal with, which is opportunities showing up. So you think- The company totally cost much more than the 100 grand that they would pay out. 

So economically- So what you're saying is that this is going to kill the SDR role? Like, not the SDR role. The this will kill the SDR role. 

It should kill the SDR role, yeah. What's the hardest leadership lesson that you learned? 

The thing that's the trick- The thing that I would focus on, the thing that I remember the 

most, the most difficult thing is letting go of 40% of my stuff. 

Because I grew too quickly, hired too many people, didn't have product 

market fits, spent too much money, was going to run out of money and burn all the capital I raised, and so I had to fire 40% of myself, sat down with 25 people back-to-back 15-minute meetings and let them all go. That was the most challenging thing and I'll never make that mistake again. 

Because ease of use is huge. We want to talk about things that remove friction from your processes. And so you can take something and simplify it for the end user. The better the whole organization is going to be, right? When it becomes hard and everything is- It's difficult and people get in and you start hearing the complaints about what's going on. That's when you start getting friction within your organization, right? Internally, you start trying to remove some of those barriers. And so I just felt that- And I have seen that HubSpot helps companies have less friction internally. 

And what they're doing- And I will literally tell you everything that I can possibly tell you that I know that will work. You don't have to pay me a dime. And the reality is that if you don't go out and execute, then it doesn't matter whether you pay for it, or if you got the advice you're free. So, you know- I was going to answer your question, but that's a whole other way of saying it. I've done a lot of cool things and here I am chatting with you guys now to talk about it. 

That's an incredible place to double-click, though, right? So we work with startups all the time who pay us a lot of money to provide guidance, advice, strategy. And we also execute as well. Like, we physically will show you how to do it. 

You know, I think about some of the gifts that I've sent. I recently sent a CRO. His name is John McHillup. He's the CRO at Open Prize. Shout out to him. Love him. He mentioned that him and his wife were going to be Taylor Swift in a few months, right? 

Amazing. So I asked, of course, if he had any friendship bracelets, if they've made the little bracelets to trade at the concert, they hadn't yet. So I went on Amazon, sent him a $15 friendship bracelet kit. And now every time we're on a call, he brings that up, right? And so it's sending these thoughtful... 

Listen, the great ignore is the fact that it takes 20 to 25 touches now to get somebody's interest. That's not even to book a meeting. That's just to, like, pique their interest. And the great ignore, really, if I boil it down to, in essence, what it is, the fact that we're sending such lazy, automated, horrible, irrelevant, uncompelling messaging that's so self-centered and so wrong. And we took those ideas that actually were semi-decent and sort of worked back in the day in the golden age of sales before the economic downturn. And we scaled that out of control. And now we have things like GDPR, CCPA, and do not call this, which are societal pushbacks, governed law body people making legislation against our own crappy salesmanship. 

Just like little random appreciation drops, those go a long way. And then, you know, when it comes to renewals, right, I don't think that gifting should only happen at time of renewal. 

You can smell that from a mile away, right? So I think it's really important to consistently check on your customers and make sure that they're happy. And you can do that with a one-to-many email campaign, like, hey, we'd love to check in on you and the team, you know, talk about anything that you may be experiencing. I think that that can really help when it comes to that renewal, just that constant support and appreciation, which is so important today, as it's been a main goal for a lot of revenue teams. 

I want to give an interesting example of this. 

And I will never forget him telling me things like, hey, did you know the Super Bowl, the Oscars, the Grammys, it's all produced on a spreadsheet? And I'm like, there's no way when I go to a concert or to a Falcons game that all that's done on a spreadsheet, he's like, oh, yeah, it is. Our industry is so underserved. I'm like, that's got to be just your company that operates that way, not the whole industry. He's like, nope, it's the whole industry, and I want to start a company, and I want you to come help me run it. And so my background was in workforce management, his was in event production, so we kind of combined our skill sets. And here we are 10 years later, changing the industry, and really excited about it. I love that. 

Shopify was interesting because they were One of the really interesting philosophies that they have is to operate as a 100-year company. We're here to build a 100-year company. So they don't get caught up, even for a public company. 

They don't get caught up in the quarter. We're here to drive value for the customer. In the long term, it's a weighing machine because the real value you're creating is what will be represented in the market cab. So the mandate I was given is, hey, you've got in my first year 80 headcount. That's earmarked for you. Do what you want with it. I was like, oh, okay. 

I get that carte blanche. There's no gates. There's no this. It's like, yeah, yeah. We know that the point of sale product is good. We are confident that a sales motion is going to accelerate our growth based on some early learning. So go for it. And so I could scale as fast as I thought we could go without things falling apart. And I could make upfront investments without needing to worry about the burn impact or overbuilding. 

And I said, I don't care what it takes. I'm having a heart palpitation. You say this like one of the scariest things I've ever been through. And then the coaster didn't stop. It was still it was still still it didn't go again. And I said, God, I promise I won't wait anymore. 

I'll just just get me down. I'll do it now. And I kid you not that that moment that 

the coaster took off and I'm like, well, I guess I'm on the hook when we get back and we will get back to a 2020 to 2020 or post COVID 2020 to 2022 economy. And there's not enough people. Then people aren't going to they won't be able to care about that. 

It's a swing. They're all markets, right? You'll, I mean, you, you remember to die. I remember going through that. Oh, I was I was a part of it. Yeah. Yeah. I went through the same thing and I remember like, you know, I thought about it at the time I was getting my grad degree and I saw a lot of people like they they'd lost their jobs and they just had to go full time back to their grad back to grad. And I thought to myself, I have to remember this time and what's happening in this space because it's going to happen again. And now here we are again going through very similar things. 

And so finding ways to test it could be, you know, making website fake websites and wait lists and Sigma mockups, just doing the very MVP of understanding how can you validate this without putting a lot of engineering hours towards it. Once you feel the pull, that's when you have to start dedicating engineering time. And we have conversations every quarter when we're doing road mapping of what percent should go to existing customers and what percent should go to new business. And it does shift based on the market and the quarter. 

I love that. I love it. I think gone is the day of the alpha cells rep. 

Yeah. Who just kicks in the door and just tries to control the whole 

deal cycle because they have this big alpha personality. 

You know, what we learn is like this like this introverted, empathetic cells rep who knows how to listen and ask great questions, brain supreme, because they're really good at running discovery. 

I was just coaching someone the other day and we were talking about how their introverted technique has really helped them excel over those really outgoing reps on their team. He has moved into the number one selling spot and he was so concerned when he started that he was so introverted and how am I going to do it? And you nailed it. That empathy, that discovery, that listening is so much more now than the person is like, we're going to do this and you didn't respond. So I'm going to send you a break up email. 

We see it all the time. Max, you you compete against some of the I'll say most well known names out. Yeah, I don't want to say the biggest. I'll say well known people who are prolific on LinkedIn. I believe I read the other day that you actually met in real life with one of your biggest competitors. Why such a competitive space with people who are so prolific in their brand? 

So is something funny to me because about a year and a half ago, we decided that we'd go pretty hardcore on a LinkedIn social strategy and just being very vocal about what we do. And we're taking a unique approach. 

I think we I just might go in clear things. So I basically transparently share all of our metrics and numbers on LinkedIn and share what I'm learning because I want other people to grow from that and not other people in our space do that, but they do post on LinkedIn all the time. 

But why do all the vast majority of companies still say, well, we're going to train on on Medpec and we're going to train on Bant and we're going to train on spin and we're going to train on disk and whatever BF acronym you want to give. And it's literally and we've all stabbing these trainings, right? Of, okay, so let's talk how we're going to go through budget authority needs and timeline. I swear, like no joke, we were talking to a customer the other day who said that the sales methodology they want us to train on is banned. 

And I literally almost throw up on my keyboard. I don't understand why sellers and leaders still think that the way to sell is by some scripted methodology of making sure you're checking check boxes. Why can't we make this adjustment to selling in a human centric way? 

I think it's because the way people go about developing salespeople today cannot equip people with the sales they need to sell in a human centric way at scale. 

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If you're looking for a proven way to win and retain more customers, visit Sundosa.com. I love this for a ton of reasons and there's so many places I want to go. Like I want to talk BDR. I want to talk creator, but I'm going to stick with creator for a second. There's so many brands out there now that I feel go to LinkedIn, just find someone who has, you know, some stats and they're like, oh, we're going to make you an influencer and go post about us or vice versa. You have some tool on LinkedIn who thinks they have cred, who posts of, you know, at whatever company I want, like, let me be an influencer for you. I, I, my gut is that is not the way to do it. 

And it's broken. Talk to us. How can brands and how are you guys helping brands properly leverage the correct influencers to grow their brand versus let me go find someone on LinkedIn who has 50,000 followers. 

Tell us a little bit about what's the thing you like most about go to market and what like really liked your passion around go to market. Yeah. 

My, my biggest passion around go to market is a lot of folks don't even know where to start in terms of go to market. And what you'll find is that once you start peeling back the onion, so to speak, they actually do have the tools and their toolkit to do it. 

They just didn't know how. And so I love, you know, expressing to folks, you had this all along. Here's a time to leverage it. And here's how you, how you use this tool or here's how you use your voice or here's how you build your brand. So it's for me, it's more educational. I love educating people on what they didn't even know they knew they could do. 

And the reason it's called that is because I do not believe there's anything such as a buyer's journey. I think we've all been forced to add that idea. And the only thing that matters is the buyer's experience through the journey. And that journey is created by sales and marketing. They've had some experience, whether it's an inbound or outbound, they've had some experience that makes them want to talk to you. And at that moment, they're on the seller's journey, my journey that I create. Right. And my job is to make that experience amazing for them. So that's how I like it. 

I like the perspective. 

Yeah. Well, the stats that I was able to find is that 95% of sales managers have never had any sales management training whatsoever, which is a great thing to think about it. I think, Adam, to your question, like, why has this happened? Why is it kind of persisted? I think low interest rates over the last decade has probably exacerbated it because because money was cheap, it was cheap to throw just more people at the problem. It didn't really matter if our churn across the team was completely ridiculous. You know, if we lost a salesperson every 14 months, oh, well, if we lost a sales manager every 17 months, oh, well, I think now the economics have changed, where it's actually not sustainable to keep operating in that way. 

They're not hitting revenue targets because the revenue targets are too high. Nobody's teaching the reps how to have the soft skills and conversational skills of, you know, managing a conversation. How do you talk to procurement? How do you, you know, prospecting has probably changed the most in the last 10 years. You know, from an execution perspective. 

So all the pains are there. The fractional stuff is interesting because I think a lot of people have gone fractional because they lost their job and then they had one or two people who said they would pay them, which is fine. Like I love this. 

Like I'm glad people can support their livelihood. What so many people don't understand, which is what I saw over the last 10 years is you're good for about six months. And then what happens? You're good when you work your network. Right. And then the good ones know how to hustle and grind and build it out and make it happen. Others don't. And then they also don't like the insecurity of it. 

I'm like, all right, well, I'll play in this field because S &B will be really good. We'll build up a lot of S &B. And then I listened to Brian, um, Hal again, talk about the future of HubSpot. And I went, I think this guy is going to try to compete with Salesforce. And I was like, that's kind of ballsy. Right. 

Like you're a small marketing company, market animation, number one in the world, but you're going to go try to compete again, Salesforce. And so I said, you know what, I'm going to, I'm going to hitch my wagon to this. I liked what he said. 

And that might be, and this is a great place to close, that might be the single best piece of advice we have ever got on this show. Because if you don't, and I don't, Dale will tell you, I don't, I'm not great at giving out praise. If you're not putting yourself and everyone talks about secret shopping and this bullshit and, but like every CRO, how often do we talk about your, your sales process doesn't align with your buyers process? Your 17 different sales stages in your CRM are not how your buyer buys. 

If you're not going through that process and saying, would I fucking sorry buy from me? And if the answer is not hell, yes, you need to change your damn process. That is the takeaway from this show. Thanks so much for listening. We hope you enjoyed the conversation as much as we did. 

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