AI, Sales, And The Human Edge with Sean Meenan

Transcript

Welcome And Show Setup

SPEAKER_01 0:02

Welcome to Scaling with People, your weekly playbook for turning chaos into compounding growth. Each week we go under the hood with battle test experts in all areas of business, from marketing to sales, operation finance, and people, plus product and leadership, to unpack the plays, numbers, and systems that turn chaos into compounding growth. Learn straight from founders and experts who've done it and continue to do it successfully. There's zero fluff, just moves that you can still immediately. This podcast is brought to you by Guide to HR. Human expertise, AI-powered impact. Welcome everyone to today's Skilling with People podcast. I'm Guinevere Curry, your host and founder and CEO to Guide to HR. So, what happens when a sales pro ditches the corporate playbook and begins building companies while exploring the world as a digital nomad? Well, you get Sean Meenan. And on this episode, we're unpacking what the last three years of AI has done to sales, why most founders are still thinking about lead generation like it's 2019 and the hard lessons Sean's learned the scrappy way. If revenue feels unpredictable, this conversation might just recalibrate your entire go-to-market engine. Well, thank you, Sean, for joining us today. Welcome and tell the audience a little bit more about yourself and what is this whole nomad, digital nomad thing that you've done.

Layoff, Grit, And Owner Mindset

SPEAKER_00 1:22

Yeah, absolutely. Well, thanks, Winterview. I appreciate the invite. I'm super excited to be here. And on a yeah, so on a personal side, a little bit about myself. I'm a Colorado guy. So I grew up uh hiking in the mountains, snowboarding, playing a lot of soccer, big Broncos fan. Go Broncos. Um and yeah, about six or seven years ago, really embraced uh the sort of digital nomad life. I've traveled through about 40 to 50 different uh countries over the last five years or so while also building um and bootstrapping my own companies. So it's been an absolutely wild journey from that perspective. Um, more professionally, uh, you know, I got a degree in finance originally and started working in financial sales, which is really where I sort of cut my teeth and learned how to sell in the first place, hammering out two to three hundred phone calls a day at a boiler room type of job in New York City. Um, and slowly kind of worked my way up through the tech world. I became an enterprise sales account executive for a while. And then it was actually during that role, which was my first remote role, where I started uh traveling while working and ultimately started my own company and the rest is history. So as of today, I'm the founder and CEO of a company called Whisper. We're a marketing and lead generation agency. So we support a lot of service-based companies as well as tech and SaaS companies to scale up their pipeline and really help them build a more repeatable and data-centric pipeline that they can grow from.

SPEAKER_01 2:47

So you shared that you walked away from the corporate track and did the whole traveling uh around the world. What did the experience teach you about cells that most boardrooms or even corporate landscape still don't like understand and know?

SPEAKER_00 3:00

Wow.

SPEAKER_01 3:02

I just started with the big one, didn't I?

SPEAKER_00 3:05

It taught me so much. I think it's an important part of my journey in that I didn't necessarily choose this. I was actually laid off um while working as an enterprise account executive. I had actually just gotten into Colombia um about a week prior and was notified that I was laid off. They locked me into my computer and I'm sitting in this Airbnb in this country I didn't know anything about, thinking, what the heck am I gonna do here? Uh and so I think I really had to um find a deeper sense of grit um that I had never found in myself before. And really what was interesting about this is, you know, when you're in the sales world, you're you constantly have a boss hanging over your shoulder who's holding you accountable to a quota, some sort of number that you need to hit. Um, but when you're on your own, there is nobody holding you accountable except for yourself. So you really need to find a way to continue to keep yourself inspired and motivated and working towards outcomes rather than sort of staying busy, which I think is the original mindset that I have, which I kind of refer to that as the employee mindset, where you feel that if you're being busy, then you're being productive and you're helping. Um, I've learned that that's not necessarily the case, and especially in sales. So when you're relying on yourself, um, it really just is a different level of accountability and you have to find the things that work. And so to do that, it's really important that you follow the data, not your gut feeling and not what you think is working in sales, but really paying attention to create different ultimately they're science experiments, right? You have to set up controls and variables and make sure that you're really measuring what is working, what's not working, so that you can lean into the strategies where you're winning and just amplify those strategies. And so that was a journey that I had to go through. And uh, you know, I've been doing it now for about five years, running my own businesses, just sort of staying with staying true to that mindset.

Busy Work Versus Outcomes

SPEAKER_01 4:51

I think you've called out such a key thing, and it's not about sales, it's actually it's that mindset, right? As we get into go from employee to business owner and be the only or key or top level business owner, that mindset really has to shift. And I've also struggled with it too when I created my business because you're right, like I felt so accomplished. Look at all these meetings I went to, look at all these things. I was so busy that I had all these emails I responded to. And then I look back and go, gosh, I like what did I actually accomplish with all that quote unquote busy work and really like looking at your calendar too, like making sure your calendar doesn't own you, you own it, because it's important to be working on the right things that move the needle. I'm constantly asking myself, am I working on the right thing that's going to get me to the goal that I have defined? If you haven't defined something, you're even you're in more trouble, right? Because you don't have that goal. And shameless plug as a profit advisor. This is one of the biggest things that I work with founders on is that accountability part because you're right, you're by yourself. And sometimes, like some people just don't have that way of putting that accountability devil, and I'm gonna call it a devil, on your shoulder, right? Like that slave master that's like, no, no, you're not working on the right thing, you're not doing enough phone calls, you're not getting enough leads, you're not moving more enough prospects through the uh close rate, right? And so it's like, okay, uh, that's I think that's such an important lesson that you learned. Have you do you still find yourself kind of going back into that employee mindset or have you kind of actually won that war?

Leverage, Delegation, And Partnerships

SPEAKER_00 6:27

Yeah, it's a I think it's an ongoing battle. I I feel that I've overcome a lot, but it's still something I battle with. And there are a lot of times where I'm still, you know, I've been trained to believe that I need to be in my seat at 8 a.m. in the morning on Monday and I need to save until 5 p.m. Oh my gosh, so true. I still sort of live that. I do work, you know, more traditional business day most days, but I think there's times where it's Monday at 1 p.m. and you really look at your task list and you think, I've I've killed it. I've I've nailed the major drivers for my business so far today. It's okay to take a break and go for a walk. You don't need to be locked into this eight-hour schedule. You're not punching a clock. And it's something that, you know, as I've grown in my entrepreneurial journey, I've also had people come from all different corners of my social network that I knew as an employee and that I met while working at other companies that are trying to start their own businesses, trying to become an entrepreneur. And they've come to me in a lot of cases, they're saying things like, Sean, it feels quiet, it feels slow. I feel like I should be busier, I should be working on more things. Like, am I wrong? Am I doing something wrong? And my answer to those people is probably not, actually, because when you're just building a business, you don't have a bunch of clients and vendors to work with and negotiate with. It is a little bit slower, it is a little bit quiet. It doesn't mean you're doing anything wrong. You just have to be relentlessly focused on the biggest drivers for growth of your business, which might mean stepping in and working for 30 minutes in a day and handling that. It might mean doing 12 hours of work and staying up on a Friday night. Um, but really it's just about understanding what the priority needs to be.

SPEAKER_01 8:00

Yeah, absolutely. Yeah, 80% of your revenue comes from 20% of what you do in your business. That's what that's what I teach, but that's basically what you're you're living, right? Um, and so recognizing that and not letting yourself get sucked into all those tasks and you know, noise. It's really noise. I mean, yes, some of them have to get done, but the other question is, do they have to get done by you? Right? If you have a team, maybe you're a solo entrepreneur, but get a VA, right? A virtual assistant, or maybe it's time that you have a couple of people that are working for you, then really lean on them too, because as a founder, you don't have to do it all.

SPEAKER_00 8:40

No, absolutely not. You want to find ways to delegate, you want to find ways to access leverage in your business and especially in your sales pipeline. So a quick, very easy to understand example of that would be if you're selling to businesses like we do and like a lot of our clients do. Yes, the first thought might be to go directly to your ICP, your ideal client profile. Maybe that's like the head of marketing at a B2B company. Or you could also leverage maybe a partnership channel where you work with someone who's an advisor to 10 heads of marketing at B2B companies. And building a relationship with that person actually might unlock the door to 10 potential sales opportunities versus one. And so I think as a founder and a leader of any company, you want to be thinking about ways, especially in the early stages of your business, to leverage the incredibly limited amount of resources that you have, especially if you're bootstrapped like I am and have been. Um, you want to leverage as much as you can to get the highest outcome for the least amount of time and input.

AI’s Real Impact On Sales

SPEAKER_01 9:36

Exactly. All right, cool. That was a good lesson, man. I hope uh the listeners got something out of it because I I do this seems to be a recurring theme with uh every business leader I speak with. It's really it's protect time is the most precious thing, and you gotta protect it. And I think the most successful leaders say no more often than yes, just because they're protecting their time. And that's another great strategy, too. All right, so let's talk about sales and and um AI. So in the last three years, AI has flipped the script on outbound, inbound, and everything in between. What's fundamentally changed and what are founders still come getting completely wrong from your perspective?

SPEAKER_00 10:14

Yeah, that is a good question that I feel we could explore for days on it. I'm sure we could fold blown retreat. Um But yeah, you're totally right. I think over the last ever since Chat GPT was released in 2023, right? Everything has has just been different. Um and and sales in a lot of ways is sort of just combining some basic tasks, right? You're doing research on lead lists and putting together lists of people to engage, you're writing content to get in front of those people, um, and then you're executing that and you're getting in front of those people and starting conversations to try to get a sale ultimately. And so there's a lot of pieces of that process where AI actually can have a pretty big impact. I do think that there are a lot of missteps being taken in the industry today, and that I think it's very easy to get distracted by shiny objects. It's very easy to think that all the hype that you're seeing from influencers on LinkedIn and other areas of social media who are really just trying to get likes and engagement and aren't really in the weeds doing this every day. You know, they're gonna be expressing a certain way that things should be done. That's not always the case. And so I think it's hard to sort of sift the wheat from the chaff a little bit in what's happening right now. And I think we want to use AI, at least internally, the way that has worked for us, to really automate some of the rote tasks that we did on a daily basis. We actually had a team in the Philippines doing a lot of data entry and research that has now 100% been completely replaced by AI. Um, but for really some of the brain heavy work and the content writing, um, AI actually, in our experience, really gives you kind of an average result. Um, and we still think that you can't outsource your brain, you can't outsource human experience yet. Maybe that changes 10 years from today, but right now, I think it's still super important that um you leverage your expertise where it's still really valuable. And so certain pieces like the actual engagement, you know, communicating with your client, we I'm not a believer that that can be automated. I think there still is a big aspect of human connection that needs to take place there. Um, but for some basic tasks like doing lead research that you might have spent hours and hours doing, you know, manually, now that can be automated very simply.

Human Connection Over AI Tricks

SPEAKER_01 12:21

Yeah, when I think about AI and what it can replace or support, uh, the two functions inside of a business I that I think like I just don't see it happening is the HR function and the sales function. Why? Because they're both relationship-based. At the end of the day, you pull back all the tasks and all the things that have to be done. What are they doing? They are building and containing and moving forward relationships. And AI just can't do that. Um, and if the world ever comes of that, uh, I hope I'm no longer around because that seems very cold.

SPEAKER_00 12:50

Yeah, it's something that I see a lot that it really bothers me in this industry and just in sales in general, is that if you look at the way that people are operating today, other agencies in our competition, in a lot of cases, you know, they're building these highly complicated AI workflows to research a lead and then write a customized message. But like if you really think about the goal of what this what these people are trying to do at its base level, they're trying to trick the prospect into believing that you actually spent time manually looking at their business or their profile and personally reached out. And I just think that AI can be helpful to personalize messages and add more info and context, yes. But I just don't believe that our base level idea and the foundation of what we're working from should start with my goal is to trick this person into thinking that this is a real person reaching out when it's actually AI. So I'm a big believer in being very, very direct. If I'm trying to sell to you, I'm trying to sell to you. It's going to be clear. And if you've got someone who receives that well, that's completely okay. But I would prefer that versus me putting on this facade as if, you know, I've done research on millions and millions of businesses all today.

SPEAKER_01 13:58

You're the best one.

SPEAKER_00 14:00

Right. Um, I think that honesty is just a very important aspect of this. And so I think that it's something that we hold true as we think about how do we incorporate AI into our own workflows. Is this accelerating our ability to be honest and build great relationships? Or are we trying to trick people? And I think we just want to really lean on what you're saying. Human relationships are still super, super important in this game.

SPEAKER_01 14:24

Yeah, so true. And as a end receiver, founders, you and I, we're founders as end receivers, we get them all the time, right? The thing that really like just uh grates me so much is I know that this was AI generated because I've already gotten this 10 times to 100 times from other people. Um, so let me ask you this: if I parachuted you into a seed stage startup tomorrow with zero pipeline, where would your first focus be and what would you ignore?

Zero Pipeline Playbook: Test Like A Scientist

SPEAKER_00 14:55

Great question. Well, I think we basically do this every day with a lot of the clients that we work with. You know, we're working with a lot of startups and very early stage companies. We do have some more mid-market established companies, but this is something that we're working on all day, every day for a lot of different companies and a lot of a lot of different industries. And it always starts at the same level, which is it's scientific, right? Sales is is art and science combined. Um, but you have to, when you don't know where to go, you got to lead with the science. And so set up some hypotheses. What do you think could work? What other types of personas and people who might be interested in your offer? Really draw that out, brainstorm, throw everything against the wall and see what you can get out of your brain, or use ChatGPT to help you ideate on this. Um, but really sort of think through all the potential possibilities and then start testing, right? So set up experiments to reach out to these people, whether that's on LinkedIn or you can go on email or you can cold call, you can go to a conference and try to meet these people in person. But I think it's super important that you identify your hypotheses, set up experiments in a way that you are going to get uh useful information back about what is working and what's not. And then you just slowly scale all your energy and your and your resources into the strategies that are actually producing results. And by results, I think that's also sometimes a tricky word because in sales and certainly in lead generation, someone might think that getting responses from a prospect or getting a sales call is a result. But at the end of the day, those calls have to move forward into your pipeline. They have to become real revenue opportunities. Um so it's it's optimizing for that. What opportunity is actually going to drive through the pipeline. And sometimes that might mean that you run a campaign that has 20% of the response rate of a different campaign, but you're actually seeing real opportunities come through. That's okay. I'd rather have one great sales call than 10 tire kickers.

SPEAKER_01 16:43

Yeah, quality over quantity in some measurement.

SPEAKER_00 16:47

Absolutely.

Why Lead Gen Feels Hard Now

SPEAKER_01 16:48

Yeah, I mean it's it's you know, lead it lead generation. It's like uh I always talk to the founders I work with of like, okay, do you want uh, you know, if you're you're a dog trainer, let's say you're a dog trainer, do you want me in your system as a lead when I don't have a dog? No, of course not. I'm never gonna convert. So like getting a hundred leads with people who don't have dogs, not gonna do anything for you. Getting 10 people that have dogs, that's gonna do a lot more for you. So it's about the quality too, right? So lead generation, and I know for me it's one of my pet peeves of what I don't enjoy doing as we've talked about in the past. But it feels harder than ever for founders. Is that a tooling problem, a messaging problem, a mindset problem? Like, why do you think it's so hard for founders? Uh, maybe especially in today with AI uh on top of it.

SPEAKER_00 17:38

Well, that's a that's a great question. I think it's a little bit of everything. A, B, C, and D.

SPEAKER_01 17:44

All of the above.

SPEAKER_00 17:45

I think that you know what's unique as a challenge, especially if you're just getting off the ground, is that you have to sort of establish some level of authority and credibility with the people that you're reaching out to. And so, especially most of the campaigns that we work on at Whisper are digital, right? We're doing a lot of work on LinkedIn, we're doing some work on email. Um, and so when you send somebody a message, what's happening, right? They're getting your message. If it's any level, if it intrigues them at any level at all, what are they gonna do? They're probably gonna Google you, they're probably gonna try to find your website, they're probably gonna look for reviews online. If you're just getting off the ground, you're not gonna have a massive digital footprint to rely on versus these enterprise businesses where someone can reach out, the person who's receiving the message already has heard of your company, already has some sense of trust that you're not scamming them. But that's not necessarily true for a new founder. So you really, again, I think this just brings us back to where we were going before is that utilize AI to help you find people to research them, et cetera, to do the tasks that are gonna take you forever. But you really do have to lean on your personal background, your personal experience, who you are as a human being, and how you can connect with the other person that's receiving your message. Um, because ultimately that's gonna be the only thing that you can do as a new founder to really spark that those first conversations when you have nothing else to really lean on.

The LinkedIn Pivot And Proof

SPEAKER_01 19:00

Yeah, absolutely. And I and uh I always look at it as what what's going on in the mindset of my prospect and what is the problem they have and what solution can I provide them that will resolve that problem? And if you go in with that conversation, it like it's triggering, right? Because like the person's like, oh my gosh, yes, I have this issue. And oh, you have my solution for me? Okay, I need to talk to you, is typically how the mind works, right? So uh yeah. So let me ask you another question here about sales and your and your experience. What's one sales belief you had five years ago that you would probably challenge today?

SPEAKER_00 19:38

Well, five years ago, okay. I might stretch this a little bit and go six, but okay, six years ago.

SPEAKER_01 19:43

Uh 10 years ago.

SPEAKER_00 19:46

Um just high level. I I didn't believe in LinkedIn as a as a channel for sales.

SPEAKER_01 19:52

Okay.

SPEAKER_00 19:52

And I had, you know, sales managers pushing this down on me and saying, you have to give it a chance, you have to try it. And I did a little bit of manual outreach where I would send, you know, 20 or 30 messages that were highly thought out and researched, and I would get no response. And so I just went, you know what, this isn't enough. I don't believe in this. Um, but as we began to scale that more and automate parts of the process so I can get more messages out and get more data, you can clearly see that it can work. And I just gave up way, way too quickly on this platform. And and to your point about how do you generate interest and um in those first conversations, it's hard if you're coming from a channel like an email, if you're just sending a cold email to somebody. Yeah, you know, I can create an email right now that is elon.musk at tesla-team.co, right. And so I think a lot of people are aware of things like that where it can be tricked. What's really great about LinkedIn uniquely is that when you send a message to somebody, it comes with a nice little profile picture. They can click on that, they can see all the people that are in your network, they can see the companies you've worked for, they can see where you live. Um, and so it's a lot more authentic. There's a lot more credibility coming behind that message that it packs a punch. And you see that in the data, you get way higher response rates on LinkedIn. And now there's a lot of people that try a couple of things and can't kind of give up. And I was that person. And so I think going back and really just being more scientific about it, um, testing different things out. And sometimes, you know, you just get crickets for three or four months, and you're just like, what am I doing wrong? And then you change the approach or you change the offer, and then boom, you have a campaign that's just hitting on all cylinders. And so it's something that I've seen a lot is just don't give up too quickly on things, keep testing, make sure that you actually have significant data samples and give something, you know, real time to see if it works before you uh you quit.

Build Authority Through Authentic Activity

SPEAKER_01 21:40

And what I got from that is it's sometimes hard to hear what other people are recommending or suggesting, but they have learned it themselves and to maybe take the chance or take the opportunity and the risk of accepting that and really double down on it. Um I actually had that moment happen to me, gosh, two, three weeks ago. Um, and it was just an aha moment. I've had it before too. Like, I go to the doctor and they tell me, hey, you need more vitamin X, Y, Z. And it's like, okay, yeah, yeah, yeah, whatever. And then, like, you know, a couple of months later, I'm like, I went to the doctor to keep myself healthy. Why am I not listening to what they're telling me to do? Right. It's kind of like, okay. So especially if you have mentors, um, coaches, advisors uh working with you or you're connected to them, like it's it's sometimes hard. Like we sometimes think we know it all, but we don't. And to really learn from them is is uh a big uh area of a blind spot, I think we have as human beings.

SPEAKER_00 22:40

Yeah, absolutely. It's hard to uh it's hard to you know motivate yourself to just do the right thing sometimes. I feel like that's actually a phrase that I heard a lot when I was in my early days as a sales rep was that you have a lot of people giving you advice and giving you guidance. And if you've been in a role for two or three years, the reality is you actually do know what to do, but in a lot of cases you're not doing the right things that you need to be doing on a daily basis. And so what they always said, and I I fully believe in this, is that you know, the difference between a really great sales rep, sales rep or even entrepreneur in my mind is closing that gap between what you know you should be doing and what are you actually doing. The smaller that that gap is, the better you're gonna do.

SPEAKER_01 23:20

Yeah, that makes so much sense. And the second thing I got from that on LinkedIn, you were talking about, you know, they you can they can click on someone's profile, you can see their information, who they're connected with. But the other thing they can do is they can see your activity, they can see your post, they can see if you've responded to other people, you they can actually start to hear your voice and understand your brand. And so it's also really key if you want to be my my thinking, but tell me if you're if you disagree or agree, is that it's also important to make sure that you're putting yourself out there in a very professional, but transparent, you know, authentic way that you can about who you are and what you do.

Final Tips: Keep It Casual And Human

SPEAKER_00 23:58

Absolutely. Well, you need to put yourself out there and you need to show a little bit of personality, right? It can't just be a robot. Um, you know, you can't run everything that you're gonna say online through the marketing legal compliance filter. Sometimes you do have to just take a stance on something, and that's a really good way to build a tribe. Um, and sometimes even the more controversial the take, the better it is for building a tribe because maybe 50% of the people read what you said and they think that you're the dumbest person on planet earth, but there might be the other 50% that now really you know resonates with that and really likes you being king. And so I think it's really important. And I see a lot too on LinkedIn of you know, there's this big wave of AI generated comments that are being posted on or even posts. Yeah, or even posts, right? And so I think it's really easy to sniff that out in most cases, and I don't think it adds anything to your credibility or your authority, or it doesn't drive anybody to become part of your tribe because it's just generic. So I think it is what to your point, when someone looks at your profile, they can see the things you're commenting on, they can see what you're talking about, they can see what's important to you. I think it's super important that you really keep that authentic.

SPEAKER_01 25:06

Yeah, that's so true. Well, I think we could, like you said, talk about AI and sales all day long. But as we wrap up today, is there any last final thought tip trick you'd like to share with the audience?

SPEAKER_00 25:18

Um final thought or trick, I would say just if you're not using LinkedIn as a sales tool, you need to start using it. Um, get sales navigator, it's super helpful. Um, and I think at the end of the day, just keep it human. Just be conversational with people when you're trying to sell to them. Especially today, I really think that AI is good at writing copy that feels like marketing copy. It feels generic, it feels average, and it feels like something you'd see in an advertisement. So the more that you can lean into just being casual, even making mistakes, even making typos or grammatical errors sometimes can actually stand out in a good way for people. So just think about that and think about how you would actually speak out loud to a person versus what would you write in a document about your business? Um, think about how you'd approach someone if you're at a party and you're gonna tell them about your offer. And that'll go a lot further for you.

Closing, Community, And Guide2HR CTA

SPEAKER_01 26:08

I love that. And as you were saying, speech, like there's so many tools now on your computer where you can actually talk to it and it will type. So if you want to try to find a way to have that um sentiment of you speaking directly, but you want to move faster, try one of those options, uh, speaking tools. Some computers even come with a tool. So uh maybe that'll be a way to help uh reduce some of the typing burden you have for the day. Well, Sean, this was fun. I really appreciate the insight. And uh I I know for myself, I'm not a salesperson. So sales is always a hot topic for me. And and I think this was so great. I hope those listening got some great tippets. And until the next time, I hope you guys all have a wonderful rest of your day and week, and we'll see you on the next episode. Thanks, Sean.

SPEAKER_00 26:53

Thank you.

SPEAKER_01 26:54

That's a wrap for today's episode of Scaling with People. If you got value from this conversation, do me a favor, share it with someone building something big. And hey, I'd love to hear your take. Drop a comment, shoot me a message, or start a conversation. And don't forget to subscribe so you never miss the bold, unfiltered strategies we drop every week. I'm Gwynaver Cry, founder and CEO of Guide2HR, where we help high growth companies scale smart with people for strategies and AI powered systems that don't just keep up, they lead. If you're building fast and want your HR to move faster, head to guide2hr.com and let's talk. And remember, scale isn't just about speed, it's about people. Until next time, have a great one.