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#63 - Is AI Taking Over Sales Roles?

14m 54s

#63 - Is AI Taking Over Sales Roles?

In this conversation, Connor and his co-host discuss the current state of the tech sales job market amid fears of AI disruption and market downturns. They acknowledge that portfolios are hurting and there is widespread anxiety, but they argue that much of the fear is overblown. Despite predictions from 2022 that SDR roles would disappear, the roles remain largely similar, with AI being integrated gradually rather than replacing jobs overnight. The key risk lies in working for "nice to have" companies that are not AI-native, while opportunities abound in sectors like storage, data analytics, and core AI. The speakers emphasize that individual sales reps who learn to use AI tools (e.g., GPTs, Claude, automation for reports and emails) are becoming more valuable, as their skills are in high demand. Cold calling is presented as a particularly AI-proof activity, relying on human connection. The overarching message is to adopt an "opportunist" mindset—embracing AI to gain an edge, rather than fearing it. Simple daily experimentation with AI, even for 30 minutes, can put reps ahead of the majority, as most peers are not actively adapting. The speakers encourage viewers to lean into AI, use it to enhance productivity, and capitalize on the current market fear to stand out.

Transcription

3346 Words, 17352 Characters

English
- Connor, what's good, man? - It's doing well. Did the V out here? - Yeah. Lake Tahoe Edition, just diving in. Once a year we get together and wanted to make an unedited video, in today's case, on the broader job market. I think let's call it what it is. Like everybody's favorite tech stock, but they have some money in, is down about 25% right now. A lot of fear in the market, and this isn't gonna be a blind, like everything's okay. Like there's a lot changing, but I think, I don't know, at least from my vantage point, I see a lot of people maybe skeptical of a tech in tech sales career, not gonna blindly say, yes, it's the best career for you, but it's changing rapidly. Curious your thoughts on the topic, and we'll break it down. - Yeah, I mean, 25% might be generous, so I think a lot of portfolios are hurting. There's a lot of, you see a lot of headlines, there's a lot of fear and hype. I think there's a lot of nuance to it. Like I don't wanna be clipped five years from now, saying that all of it was overblown, but in my opinion, a lot of it is kind of fear mongering, and if you actually look at how much has changed in the last four years, really since the advent of ChatGPT in this whole AI era, a lot of roles still look pretty similar. It hasn't played out like a lot of the people in 2022 talking about how SDR roles are gonna be dead within a year. Four years later, here we are, and yeah, we're starting to integrate AI into our workflows a bit, but for the most part, a lot of these roles are still the same, but at the same time, you gotta stay on top of this stuff, because if you're not, I mean, eventually, there is gonna be a point where you are falling behind people who actually know how to leverage AI are gonna thrive in this new era. So it's hard, I mean, it's easy, like I'm not gonna act impervious, sometimes I see headlines, and I'm like, "Oh shit." And then I look into it, and I'm like, "All right, let's actually break this down. How much of this is actually gonna change daily? Is this actually taking over jobs or responsibilities? The truth is gonna be somewhere in the middle." - Yeah, no, I totally agree. I think if there is one risk that maybe wasn't present five years ago, I think even more so than ever, it's getting at a nice to have company. Think anything dashboarding, anything that kind of like pulls lots of disparate information together. If it's not AI native, I could definitely break that down, but that's a huge risk. But I think on the other side of it, things like storage, database, data analytics, obviously your AI companies that are doing like really meaty work, not just AI wrappers on top of something. There's so much evergreen opportunity, and I think if you're on the forefront, it's insane. And like last thing I'd say on at least this point is, I know we've been poking around a lot with like cloud co-work and how much we've already done there. There's no doubt that's disrupting a lot of workflows, but I think the individual rep right now, if you are in tech and tech sales, you are learning how to use AI on the forefront. Not only do I think one, there's huge demand for people who are actually leveraging this correctly. The things you have access to, even in 2026 compared to last year is insane at your fingertips if you know how to use it. So that value is going up. The individual rep value is going up as these other things like marketing, coding, become more commoditized. But also I think, again, not that my Doomsday scenario is like everyone's gonna be out of job in five years, but if things rapidly progress, I think if you have the skill set of being able to leverage these incredibly powerful tools in a sales capacity, God forbid you lose your job, God forbid you want to pivot. Like I have to stay focused right now because my first spot with all of the AI going on and my sales skills is, dude, let me approach some businesses that have like a 1990s or early 2000s tax stack and overhaul everything for like 10,000 a month. Like that's where my mind is at right now. And my point being is if you can get paid to learn all of that, I think it's still an incredible skill set. Tons of demand, we're still seeing tons of people break in, but that was a long run. I'll end it to you. So yeah. - He can, uh, the portfolios in the beginning, you almost have to treat the company you pick, almost like you're picking a stock. You can't just take a job anywhere and not think about how is this company position 'cause you're right. A lot of those nice to have companies, if you're just like a simple dashboard or like a little marketing widget that you integrate into some broader system or system of record. Like yeah, there's probably some companies that aren't positioned well. So you wanna be able to sleep well at night that your company isn't a good spot and has a good trajectory moving forward. But I think a lot of people take one of two sides. Either you can be an AI opportunist or like a Doomsday or I think the Doomsday or one is appealing where it's like a lot of people, you sound smart when you say it. It's like, oh, AI's gonna take over everything. We're gonna hit super intelligence and AI's just gonna be working all sales jobs. And it's like, yeah, you could take that route. I don't think you're gonna be right. I think there's a low probability that happens, call it anytime in the next 10 to 15 years personally. But like if you're right, then you're screwed anyway. So you might as well be an opportunist because chances are there's gonna be a very long stretch period where it's people who actually know how to use AI and learn it and implement it to make themselves more effective salespeople that will make a lot of money. As a lot of companies need to buy AI tools and systems like someone's gonna sell that stuff. It might as well be you. So cash in and make some money. And then we can worry 20 years down the line when there's AGI and super intelligence like taken over our jobs. So I would rather be an opportunist and be wrong than just be a Doomsday or just sit here and you're basically resigning yourself to failure. It's like you kind of have to hope you're right at that point. 'Cause if you're a Doomsdayer and then it turns out AI doesn't take all the jobs and there was actually a ton of money to be made. Well now you just sat there being a pessimist and didn't do anything about it and missed out on the opportunity. So you might as well be an optimist and you don't, I think a mistake a lot of people make is they see all these LinkedIn posts and cloud co-work and all this new stuff coming out and they feel like if they're not automating their end-to-end workflows and using AI STRs to do their jobs for them that they're falling behind. We're still in a time period where if you are making basic GPs or projects or gems for Gemini, whatever you use around core workflows that you do repeatedly in like saving you time, writing email templates, writing scripts, taking notes on discovery calls. You're ahead a 90% of the crowd 'cause most people have their head in the sand when it comes to this stuff. So it's like you don't need to start by running the marathon to start with a three mile run and then a five mile run and work your way up. It's the same thing with this stuff. So it's not hard to get ahead of the crowd. I mean that's what we're here to do is help you guys figure out how to actually implement this stuff as sales reps. But I'm very much on the opportunist side. I think we're gonna look back 20 years and it's gonna be one of those things where you kinda laugh at the people who were, I think this is just so obviously gonna make all our lives so much better and you already look back at stuff even four years ago where you're like I can't believe I used to have to manually take notes on calls and draft the email afterwards and enter all the YOS, Y now, like in the sales force. It's like all that stuff is so easy now. So I think it's only gonna get better and better personally. - No, I'm with you 100%. I mean last month alone I'm just thinking back on students that have reached out to me. We've done testimonials with like your snowflakes, your oracles, your deals, ramp, rippling, like tons of students that are still breaking in. So just on like a yes or no is the job market cooling down. I think there's still tons of opportunity and like I said, even better. And then also just adding some nuance and some flavor to this as well. I think it's like especially if you're early in your career or maybe you're transitioning and wanna be a business owner in the future and/or learn sales have higher upside all of these things. You get a front row seat if you're at the right company at how AI is like integrating into massive businesses. And like what an opportunity to get paid during your day job and if you're ambitious and I know tons of sales people try to do things on the side. Like you get a front row seat to see the biggest challenges that AI is trying to solve. And then on top of that you have the luxury of being in the industry, being well versed in the tools and being able to do things on the side like we talked about, I mean it's insane. Literally yesterday in about 30 minutes I have a cloud co-work automation that takes our YouTube videos and now makes it a blog post, post ready on our website with zero other effort. Like it's absolutely insane. - There's a huge opportunity for, this isn't, I'm speaking in generalities but a lot of our audience is 35 and below. A lot of the people who need help in the ones who are running these sales orgs are above 35 and they're the ones who particularly, not all of them. Like we have lots of them on our channel here. But a lot of them have their head in the, their head in the sand and don't know what to do with AI. And if you can just become that AI expert within your org, again not doing anything fancy, not automating entire workflows, but if you can share GPTs with your team and your org that do things like prep for discovery calls, call call scripts, email templates, whatever your job is, you can really separate yourself and you can see like you said, you can get paid to figure out how businesses are using this and how you can add value. Because here's the other thing is, and I hope this calms a lot of people who have AI fear. You know who actually made one of the best points on this, I think is funny enough is Ben Affleck on Joe Rogan's podcast. They're talked because in that industry, they're talking about how like movie production and TV shows, it's everyone's gonna get replaced because AI's just gonna be able to spin that stuff up for basically zero costs, so why pay for all this stuff. And the point he made was that AI always will revert to the median, like it's very easy to get a minimum viable product. It looks like a script, it looks like a movie, the characters look real, but it still requires that elite technical expert from like a movie production standpoint to finish that lap. That's the hard part, finishing that last 5% to take the AI median, the AI slop and use it to save time and turn it into a high quality output. It's the same thing in sales where it's really easy, like a lot of leaders are thinking, oh, I can replace my SDR, look how easy it is to draft email templates, because yeah, it's easy to just say, hey, I work at XYZ Company, write me an email template for an HR director, and it looks like an email template, it looks clean, it's written grammatically correct, but it reads and sounds like AI, you need someone who's a top 10% producer who knows how to coach the AI and implement that nuance to all of these workflows. and that's your opportunity is like the people who actually do this at a high level on a day-to-day basis are going to be the ones who know how to take AI, apply it, spread it to their organization, become that AI expert or subject matter expert. I don't know. There's just so obviously so much opportunity with this stuff. I see it in my own day-to-day. I hope all of you start taking advantage of it because yeah, a lot of the people who need the most help and are actually in charge of running these sales orgs are the ones who still barely know how to even prompt chat GPT at this point. Yeah. Now I'd say in closing on my side too, you know I can't get specific but we have a very detailed engagement where someone alone their first week as an SDR set four meetings straight via Cole-Cole. No email, nothing. Four meetings via Cole-Cole. I myself this past week Cole called someone that we were in conversations with on an engagement. Cole called them, they picked up the phone and they ended up signing that evening. So in terms of the tactics, yes, on some ways it's getting harder but I would say one, personally, I get 50 plus spam emails a day now and I have maybe two people actually give me a genuine Cole-Cole per week and two, I would just say it's like again, what we teach here too has always been at the framework level and it always evolves. So it's like, go back to 2020. Most SDRs were not even aware of how to build like detailed reporting in their CRM and I still think 80 plus percent don't even give enough of a shit to even dry quite frankly and that's why our students do so well is because you're just looking for the thing that gives you an edge. AI is not going to replace SDRs like your point on the creative copy, how to actually connect with people and things of that nature but the person who is codifying their work in GPT's, they're codifying their work in Claude skills. They are using if they have access like the Claude HubSpot connector and they're able to create extremely detailed reports not only that other reps don't have but maybe they're able to generate them faster and literally that extra four hours back you're getting by having Claude automatically create those reports or whatever the case may be. That's your advantage as an SDR and it's not that it's ever going away but the tools the leverage that you have is something you need to constantly reiterate whether it's content like this or otherwise like that is the thing I would be worried about with AI is what are my peers doing that I'm not even aware of or what are things if I even gave it 30 minutes a day in seat with the tools that I have with all the AI capabilities. If I blocked 30 minutes a day to try and do something with AI that I'm doing manually right now could I get as good of a result or better if I had AI do it and that's literally all it takes. Do that for 30 minutes a day like learn even 15 just play around like learn like practice making a GPT play around with Claude again it's like most people aren't doing this it's not hard to get to be on the AI forefront you don't need to be like you know who what's his name Dario and Anthropically you don't need to be at that level you just need to start testing with it like playing around with it codifying your workflows one last point I'll make too on the cold call front that might be a whole separate topic I guess let us know if you want to see a video on that I think that email is still going to be important but I think cold calling going forward is going to be the most AI proof form of prospecting I think it's going to get more and more important most people don't know how to do it don't want to do it there's not as many people cold calling as you think and it's something that is so far away you can clip me on this like 10 years from now I still think AI is going to be clueless when it comes to making cold calls I also think there's risk that's like of like regulatory I don't think people are going to want like AI bots cold calling or at least it's going to have to present itself as AI that's just a prediction which is totally going to make it ineffective so the human to human connection knowing how to cold call for AEs that would also be like going on site stuff like that that AI can't replace you got to be figuring out which which activities and things like that are going to be AI proof and become more important than ever so I guess let us know if you want you know follow the video on that yeah well great stuff I mean again you know it's I think the people that are doing the things that it's funny like I feel like in times like this where the market's down like yes there are bad companies there are bad opportunities to avoid to be very clear but at the same time like it's crazy how much I even see in the comments and whatnot in the last month and a half two months on TikTok on YouTube of like oh tech is going to zero you know xyz that's maybe a bit dramatic but all that to say it's like now's an even better time to kill it because there's a lot of people that see a CNBC headline and then their goals and dreams of becoming a tech sales rep go because they're just playing scared like if you're cold calling a hiring manager if you're reaching out via LinkedIn email all those fundamentals that stands out times 10 maybe we'll cap it there if you have something else I don't want to be summarized it well go down swinging the the AI stuff is is I don't let yourself get scared out of it it's going to be a big opportunity so let's just lean in and figure out how to use it yeah well Lake Tahoe Edition part one signing off

Podcast Summary

Key Points:

  1. The job market, especially in tech sales, is experiencing fear and volatility, with some portfolios down about 25%, but the speakers argue much of this is fear mongering.
  2. AI has not eliminated sales roles (e.g., SDRs) as predicted four years ago; instead, it is being integrated into workflows, and those who learn to leverage AI will thrive.
  3. Individual sales rep value is increasing as AI automates commoditized tasks (e.g., marketing, coding), creating demand for reps who can use AI tools effectively.
  4. Choosing the right company is critical—avoid "nice to have" companies that are not AI-native; focus on companies with strong fundamentals like storage, data analytics, and AI.
  5. Speakers advocate an "opportunist" mindset over a "doomsday" one, emphasizing that AI will enhance sales productivity, not replace it, for the foreseeable future.
  6. Cold calling is highlighted as the most AI-proof prospecting method, as human-to-human connection remains irreplaceable.
  7. Simple AI adoption (e.g., using GPTs for email templates, call scripts, or CRM reports) can put reps ahead of 90% of peers, as most people are not actively experimenting with AI.

Summary:

In this conversation, Connor and his co-host discuss the current state of the tech sales job market amid fears of AI disruption and market downturns. They acknowledge that portfolios are hurting and there is widespread anxiety, but they argue that much of the fear is overblown. Despite predictions from 2022 that SDR roles would disappear, the roles remain largely similar, with AI being integrated gradually rather than replacing jobs overnight.

The key risk lies in working for "nice to have" companies that are not AI-native, while opportunities abound in sectors like storage, data analytics, and core AI. , GPTs, Claude, automation for reports and emails) are becoming more valuable, as their skills are in high demand. Cold calling is presented as a particularly AI-proof activity, relying on human connection.

The overarching message is to adopt an "opportunist" mindset—embracing AI to gain an edge, rather than fearing it. Simple daily experimentation with AI, even for 30 minutes, can put reps ahead of the majority, as most peers are not actively adapting. The speakers encourage viewers to lean into AI, use it to enhance productivity, and capitalize on the current market fear to stand out.

FAQs

Yes, despite a 25% drop in some tech stocks and widespread fear, there's still strong demand for sales roles, especially at AI-native or essential companies like data analytics and storage.

Treat it like picking a stock—evaluate the company's positioning. Avoid 'nice to have' companies (e.g., simple dashboards) and focus on those with evergreen needs or AI-native solutions.

No, AI is unlikely to fully replace SDRs soon. It's more about augmenting workflows—AI can draft emails or take notes, but human skills like cold calling and creative copy remain crucial and AI-proof.

Be an 'AI opportunist' not a doomsayer. AI offers huge potential for those who learn to leverage it, and most people aren't using it yet, so even basic adoption gives you an edge.

Start small—spend 15-30 minutes daily testing tools like GPTs or Claude to automate repetitive tasks (e.g., email templates, call notes). Codify your workflows in these tools to save hours and stand out.

Yes, cold calling is becoming more important and AI-proof. Most people avoid it, so human-to-human calls stand out, while AI bots are likely to be ineffective due to regulation and lack of personal touch.

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