S7E2 - Sales Strategies, Trends, and Insights: Shifting to RTO

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Are you doing it? I guess I'll do it then. Perfect. You do it together.

What's up everybody? Welcome to another episode of the Surf and Sales Podcast. I'm Scott Lise. That's Richard Harris. We're a little rusty.

We have— we've been— it's been a minute, man.

It's—

I think we've done one this year. It's 2026. It's almost March. And we've decided to change the format a little bit. We've decided that we're going to— we're going to— we're thinking we might tap out at episode 500.

We might count down to 500.

I think countdown to 500. We are at 480 this episode. As of, uh, the recording date of February 24th, 2026, will be our 480th episode, uh, our 7th season. And we're going to change it up a little bit. We've decided to, um, just have the two of us talk about different things that come across our world, come across our desks. A lot of things we agree on, a lot of things we disagree on. So we decided to change the format for the next 20 episodes. So we appreciate you being with us, and, uh, uh, hopefully we don't bore you or put you to sleep. Or if we do put you to sleep and that's what you need, congratulations, we're going glad to do it.

Yeah. Do you know how— do you know how many days 480 hours worth of content is, Richard?

I have not. Uh, well, it's more for me because I'm the one who has to do all the work behind this. True. I knew it's 480 hours.

Yeah, 480 hours of actual, like, recorded content. That's 20 days.

20 24-hour days. Is that—

we could have just locked ourselves Yes, for basically almost a whole month. That's fantastic. And do nothing but listen to the Surf and Sales podcast for the whole month of February, basically.

Man, that's like better than a lot of Presidents Club. Better than any president.

That's a lot of content. That's a lot of content.

All right. Today's topic, and we might shift because that's just how we ramble. Returning to office, right? So this is one of those things that's coming back around. I actually like being in an office, even though I've been working from home longer than everybody since about 2012. And Scott, generally speaking, doesn't want to go to an office.

So Scott, I don't—

what are you, what are you hearing from people? Like, is it coming back or is it just headlines? Like, are still more people being pragmatic from the cost perspective and doing remote?

Well, I think it's a little bit of both. I think the smaller companies, smaller startups, are still doing the remote stuff. And then once you've hit a certain scale, it seems like everybody wants you back in the office. And it feels very much to me like the power dynamics have shifted completely back to the employer has the control and has the power. Yeah. You know, I think a lot of that has to do with like the AI revolution and the fear of, you know, doom and gloom of am I going to have a job in 6 months, 12 months, 18 months, whatever. So I think people are just, you know, sucking it up and having to do what they have to do.

So let me ask you, because I know you work with a lot of early stages, right? Um, a lot of founder-led sales stuff. Um, Are you seeing them? Are they asking you, hey Scott, when should we get an office? Or, because I know you're pretty early stage with most of your business, so it may be too premature, but like, are they even asking you this question? And if so, where do you think that answer is?

They don't really ask that question at all. Sometimes they ask it with the context of, hey, we're looking to grow our sales team from 3 people to 10 people or something like that. You know, if you were going to do that, would you have everybody in the office or would you have everybody remote? You know, and most of my career prior to 2020, I would definitely have said everybody should be in the office. I built and scaled sales teams. It was always in the office. Then 2020 hit and, you know, it felt very much like, oh, remote, we could do this. Remote, and so I would build remote team. And they're asking me that question right now, and I really don't have a good answer. The answer I find myself giving has been very dependent upon the situation, the company, who they're selling to, what the sales cycle is, the seniority, the seniority of the tenure of the team. Okay, so an example would be like if we're, uh, doing quarter-million-dollar deals and, you know, we've got a team of 10 and everybody has 10 to 20 years of experience, I don't feel as compelled to say we need an in-office sales organization, right? But if we're, you know, a team full of salespeople who have like 2 years experience total on average, I'm going to feel more compelled to bring everybody into an office and have more in-person teaching moments and collaborative kind of learning and accelerated ramping potentially. So I, I think about it a lot like, a lot like that, you know.

But do you, do you think that the, um, are people now trying to hire geographically again though? Like the, the whole cool thing about, you know, the remote thing was that you could hire anybody anywhere, right? And now are, you know, you know, and I just don't know, like, you know, I'm in the Bay Area and I know the office buildings are starting to fill up again, which is great. Is it these early stage founders who like to have everybody in the office?

Do you think?

Is it, you know, have you noticed any trend there or?

No, I got to say that the real early ones, the like seed stage, Oh yeah, Series A ones, they're all remote. Yeah, it feels like to me the, the larger Series A to Series B ones, they're the ones starting to kind of, you know, command people be in the office, want people to be more geographically aligned. I mean, I, I was helping a client on an account executive search and somebody lived in San Diego and the client was in San Francisco, and that was like problematic.

You know, 2 years ago that would not have been problematic.

That's it. No, not at all. It's the same time zone, it's a 1-hour flight, right? But now it's problematic. But in the same breath, I have a Series A client that was hiring a VP of Sales, but they're based in the Bay Area and they don't care where the VP of Sales is. So it, it seems from my perspective is very case by case.

Yeah.

You know? Yeah.

Yeah.

But it sounds, it also sounds like it's case by case based on experience of the sales team. I would assume some level of experience of that leadership team, right? If they're early stage leaders.

I would agree with that.

Right? Early stage leaders probably need their early stage salespeople all in one location. Right? Like they just, they all gotta learn from each other. Is my opinion. Tell me if I'm wrong.

No, I don't disagree with that assessment at all.

And what do you— how do you— so let's reverse it, right? So if you're doing— because I've never been a fan of the remote world, right? How do you ensure training and coaching actually occurs, right? Is it all related on you know, non-sponsored companies because we won't mention their name because they aren't sponsoring us at the moment, recording softwares, or is it, you know, how did you see that working?

You really have to proactively build it into your, to your day, into your schedule.

Yeah, but you know, I hate buzzwords, Scott. What the fuck does that mean?

What buzzword was that? Proactive is a buzzword?

Build it.

Yes. Oh my God. Okay. You just haven't said buzzwords piss you off in a while. Um, you have to, you have to put it in your schedule. You have to say like, you know, 10 AM or whatever, I'm meeting with Richard and we're having a, you know, 15-minute chat. And then 10:15, I'm meeting with Scott, I'm having a 15-minute chat. So you have to have like frequent kind of check-ins with people and They have to be about a specific topic, pipeline management, I don't know, activity coaching, closing, objection handling, whatever the topic is. Um, you have to make the most of it. You know, I don't think you want to manage or can manage remotely by having 30 to 60 minute one-on-ones with everybody on your team. The whole day is gone before you know what happened. So you have to be very efficient with your time. Very kind of targeted with whatever the topic is and whatever the message is and kind of get in and, and get out, you know. But you have to do it regularly. Yeah. And you have to not book over it. You have to not cancel it as a manager or, or as a rep. Um, yeah, and I think if you don't, if you don't plan it out like that and stay on top of it, it just gets away from you. And then the team and your performance struggles and suffers. But this is part of the logic of why founders, you know, are trying to pull people back into the office because they find it difficult to develop people remote, difficult to manage people remote. They think ramp times are slower remote. And I think you believe that. That's a great question. I think I want to say the answer is yes. I think it is harder to do remotely. It requires different skill sets that not, not that many leaders and, and managers, you know, are great at or got good at. Um, I think there's just so many opportunities to learn faster when you're in an office and surrounded by all sorts of people. So I think if you have a team of really junior-level people, it, it makes a lot of sense to have everybody in the office. But a team of senior-level people, yeah, I just don't really think I need that.

Yeah, yeah. Well, usually those 6-figure deals are for lack of a better old-school phrase, is field sales, right? Where you are still going out to visit people. So proximity to where they're— yeah, to their, to their location and where they're based out of in their territory may be more important than proximity to the home office.

Well, talk about trend lines. The, the amount of conversations I'm having about field sales has astronomically gone up.

What do you mean?

Well, Scott, you know, do you think we need to get out in the field and go meet prospects? It's getting harder and harder to get a hold of people on the phone or, um, you know, email or LinkedIn or whatever, getting people to make decisions. So all of a sudden I'm having conversations left and right about how do I develop a strategy to go out into the field. How often should we go? You know, how many appointments in Omaha are needed in order to justify a trip there?

Right.

How often should people go? Is 25 to 50% travel a reasonable expectation to put on account executives?

Right.

And what should our strategy be? Do I just show up and knock on the door unannounced? How do I kind of alert them, right? Do I call people up and say, hey Richard, I'm actually going to be in La Merinda, you know, next Wednesday, would love to meet up? And then even more specific than that, like, what are we doing? Are you just asking people to get a coffee? Are you asking people to just meet at their office? Is there any creative things that we can— you can do? So this last couple months for me, I've had so many conversations about field sales, basically. People saying, how do I build a field sales team? All of this has really like increased in the last few months for me.

It's so funny because I remember when, you know, when COVID hit, right? I had all these companies coming to me saying, I've got a field sales team and they don't know how to do inside sales, right? And it's come full circle and I'm like, really? Like, and I know, look, I think you and I, we both grew up sort of doing inside sales, right? I did one year of outside sales. I hated being a dashboard warrior. It was never my thing, but it was super interesting that people were like, I don't know how to do this from outside to inside. Right. Which to me is not that hard. Like, that's, that's a very repetitive, know your process, know your tasks, know the motions you have to go through, you know, to, to make things happen. Flipping it though, from someone who's never done outside sales and they've only done inside sales to outside sales. That feels like a much bigger hurdle, but maybe that's just because of how I was conditioned, you know, through my own career. Because you're right, like, what is the meeting? How do I even, you know, if I can't generate a phone call meeting, what makes me think I can generate an in-person meeting?

Right? Yeah. Yeah. So it's what, what I'm finding is the results seem to indicate a regular sales message might go unanswered or replied to, but a message that says, hey Richard, I'm actually going to be in Moraga on Tuesday, you know, would love to stop by and just say hello, that message is getting responded to.

Interesting.

Yeah.

Okay, that's— which is— so I'll go deeper and say it sounds like people are craving that human touch.

Right, yeah, it's definitely possible, you know, for, for if no other reason than they know it's real, right?

Right, they're looking for that IRL.

Faked— they know it's not fake. It's not gonna be a, you know, AI slop or auto-generated something, right? There's like— I can sit across from you and have a conversation about whatever is going on in the business, whatever tool you're selling, or whatever. Yeah. Right. Yeah.

Cool, cool, cool, cool. What else? Ask me something, dude. I've been interviewing you for the last 15 minutes.

Yeah, well, what I want to know is, have you Claude coded something yet?

I have not Claude coded anything.

And are you going— are you going to learn how to do one of those things, or are you just gonna say nah?

What do you think my answer is?

I think you're going to say no thanks. And I think that what you'll do is— and this is, I think, a huge near-term emerging market business opportunity— is, uh, I think you'll hire somebody to sort of do that cloud coding bit for you if you have a particular need or, or a good idea. And I think that will become a real short-term, like, powerful service industry type business. AI, my business. Claude Code does the thing for me.

Yeah, I haven't, and I have leaned towards not doing it, but I'm, I had a conversation at dinner last night and I am going to start self-educating a little bit more. I think there's some online stuff from Harvard and Stanford around that's free around AI and coding and sort of the future of it. And I, I do need to be better at that because you know me, I'm a creature of habit. Right? I don't like to get out of my comfort zone. So that is going— that is one of my things. I will let you in on a secret. Just for the sake of it, this afternoon, because I have a little bit of time, I'm going to apply for the sales roles at Anthropic and ChatGPT. Oh my goodness.

Just for fun?

Just for fun, because I'm curious, like, You know, and I know, look, I'm gonna write everything myself. I know not to put it in everything. And, and of course my, you know me and my ego, right? But it's like, where's my resume? Here's my book. Fucking tell me, like, what's my resume? I've trained everybody at Zoom and Salesforce and Gainsight and all these huge companies and General Electric, right? Like, what more do you want? Right? Billions of pipeline creators.

You know the, you know the objections that you're gonna get.

Yeah.

They're gonna say, okay, well you've been, running your own business for, you know, right, 15 years or whatever, you know, why do you want to— why are you stopping?

Yeah. Yeah. So, well, I got to, I got to even get to that part, right? Like, that's the interesting thing. I think my biggest fear is that I will apply and I'll just get thanks, no thanks.

You know, are you going to get aged out?

I mean, it could be everything from age out to, you know, my resume Yeah, has great, you know, 100+ consulting gigs of training people and closing my own business. But I don't have a traditional resume at this point, so I could see them being like, who is this guy? He's desperate.

You're not gonna, you're not gonna blind apply though.

Oh no, no, no, I gotta put some thought into it. Like I can actually build something and get an intro from somebody and try to cut the line and whatnot a little bit, you know, so we'll, we'll see how it goes. So, um, You know, yeah. So if you know anybody over there or anybody listening knows anybody, you know, hit me up. I'll start applying in the next week.

That would be great. That would be funny.

So yeah.

And you're doing that just for the sport of it?

I'm actually, I'm doing it because I'm curious to see one, yes, the sport of it, but I'm actually curious to see what that interview process looks like if I can get into that interview. Right? I'm curious to see what they're looking for. What are, what are these kinds of companies looking for in an industry that didn't exist? Right? You're almost like, it's like you're, you know, you're selling airplanes after the Wright brothers. Right? It's kinda like, okay, we know this works. We know that it's there. You know, I wanna understand, like, you know, we talk about how fast AI is moving, but How fast is it moving at that, you know, fortune level and how is it moving fast versus that startup level who just, as you said, will cloud code anything.

Yeah.

Right. So, so there's a whole bunch of stuff. And then I'm also curious to see what these companies, how they run themselves, right? Like there's, there's a whole lot of curiosity. Not that I want to go write about it or anything. I just want to, I'm curious. So, you know, we'll see. We'll see how it goes.

Well, I built— it's terrible, but I built my first thing. Yeah, I tried to build this little cloud code thing that does my taxes for me.

Right. AJ's not going to like that.

Well, which independently is a massive business opportunity, I think, for somebody because.

Right.

Nobody wants to do their taxes and nobody wants to pay an accountant $10,000 a year, right? You know, nobody wants to use Intuit or TurboTax or whatever anymore, probably, right? Um, let's spit out something. It's very interesting, you know.

How accurate do you think it is? Are you— I'm sure you're gonna compare it to AJ.

Yeah, I don't think it's very, very accurate. I think I made a million mistakes, but at least I have a working prototype now that I can kind of try to refine. I'll definitely put it side by side to my accountant and see like the delta between the two and right, whatnot. Um, but my, my problem, which I maybe would assume is a lot of business owners' problem, or even busy parents and executives' problem, is just where am I supposed to find the time to learn how to do this, right? Because I'm running my business, or businesses in my case. I'm still, you know, parenting full-time, traveling, all the things that you're doing. And now on top of that, in order to stay relevant, I have to learn this new stuff. Yeah, and you know, everybody's like, you need to be spending, you know, 2 hours a day like learning AI tools or coding things, whatever. I'm like, fuck, where do I find 2 hours a day, right, to work on that? Because if I'm working on that, I'm not doing something else that I need to do in my life. That's my challenge right now is I understand the need I understand the opportunity, and I struggle to prioritize the time required to get good at it because of the sacrifices that result in the near term for me. Yeah, that's, that's been hard. That's been hard for me.

Yeah, that, that, that's why it's so easy for me to go, no, I don't think so.

What do you mean? Like, I don't know, it's not hard to find the time. Oh, to say, nah, I'm not gonna do it.

I'm just not gonna do it.

Yeah.

Oh, yeah.

Don't worry about that.

Well, then do you worry? Do you worry about finding yourself obsolete?

Oh, well, first of all, I'm 10 years older than you. So I have a much shorter horizon. So I do and I don't, like, you know, I've been talking about this for a while, you know, like, I'm, I'm I think that when I'm— when I quote unquote, I don't know that I'll ever officially retire, you know, but I will take business as it comes kind of a thing, right? Just because I need to keep busy, right? But at some point, you know, I need to go do something else. So no, I think I would say that the good thing about all the AI for me, you know, is that it is forcing me to lean in a little bit harder. All jokes aside, all the humor I've been saying, it's like it is forcing me to lean in. Like, let's, let's say, turn around, you know, Anthropic turns around and offers me a job. Do I fucking take it? Because I'm sure it's not right.

What an interesting dynamic that would be.

Yeah, right. Like, it's kind of like, wow, if I want to be relevant and this company, you know, sees my value and sees that I have enough value for them, Shouldn't I go do that for 2 or 3 years? Like, what does that set me up for?

It also could be a gravy train for 2 years, right?

Like, there's 100 things that could happen out of that, you know? And you know what it's like. Like, I got to pay my own health insurance. And when you're a consultant, it's not always— Yeah, it's hit and miss, right?

So it's up and down sometimes. Yeah.

Yeah.

So if you read the news too much, you know, it says all knowledge workers are out of a job in 6 to 18 months anyways. So you better prepare and do something else.

It's like, yeah, that's the, that's the part I don't believe. That is the part I don't believe.

It's been nice to see more thought pieces saying the opposite of that.

Yes. Yes. I think certain things, like I was talking to someone last night, I was, I was talking about, you know, Those thought pieces are, to me, those are the lawyers and the accountants. But what I think's gonna happen is I will go and write something, have whatever, write it for me from a legal perspective, and then I'll hand it to my lawyer and say, go through any research. I know it's research. You just tell me what's missing. Right? So now I'm paying them for an hour instead of 4 hours. Right? Like, that's where I think they, those people get hit. Right? We already do it with doctors. It's like, oh, I've got these 6 things. Hey, Doc, I think this is my challenge. What should I do? Right? We already use Dr. Google. Right?

Yeah. Dr. Google.

Like, it's the same thing. So it'll just, it's just gonna be an interesting time, man.

Can you imagine the power of if you, if you got that sales role to just try to ring somebody up and be like, hey, this is Richard from Anthropic.

Right.

You think that's exactly, you think people might take that call, their ears perked up a little bit, you know?

The right people would. The people who know me.

Do you think, do you think I should also apply to these roles and you and I can compete to see which one of us gets farther in the process?

That's why, that's why, because I don't want to lose.

You might win. You might win.

I'd rather just win in my head. No. Yeah. I mean, why not? Like, it's an interesting, like, granted you don't have time in your day, right? But it would be an interesting thing just to like experience that. I mean, it's been so long since I've been through an interview. My, my expectations. Applications are low, you know what I mean? So even if I got the interview, I'd have to check my ego big time.

It'd be really hard to be managed.

Yeah. Yeah. So we'll see. Hopefully, hopefully I'll get through the process before this episode drops.

Well, you'll have to keep us, you'll have to keep us posted on the, on the progress of, of your application.

I will, but it's like, think about it. It's like they're going to go Google any candidate, right? Or they're going to throw it in their own LLM. You and I probably have the most amount of information that would overwhelm them when they research us, right? Like, to the point of like, what the fuck?

They might just be like, oh, it's too much. I can't even handle this. Yeah.

Or like, this guy's trying to use us. Like, you know what I mean? Like, they could see that too. Which is not the case for those listening.

Yeah.

All right, brother.

How do you— last question since Surf and Sales is coming up in November.

November.

Just a quick little plug for the Surf and Sales Summit coming up in November. 18th to 22nd, I believe, of this, uh, year. We sold a few tickets. We usually— yep, we've sold a few tickets. You, you are blissfully unaware, you're working on other things. I've sold a few tickets. We are chipping away towards, uh, June, July. We usually sell out in the summer.

We do.

My question is, what do you think people will want to talk about the most at Surf and Sail.

It's gonna, it's gonna be, yeah, it's gonna be AI, right? In a more structured way. I think, you know, when we did it in Portugal, you know, back in October, it'll be interesting, right? Because it'll be 13 months since we last did it, right? Um, it's, it still felt a little more unclear, new, scary, etc. Now I think there will be more clarity and some more scaries and hopefully a stronger sense of where this is headed. Like, I think, I think everybody will like to know their fears will be answered. Am I losing my job? How fast am I losing my job? What is the latest? And now there's more use cases of how to do this, right?

Yeah.

Like the Claude Code thing, right? Like, you know, I, you know, I'm, I'm still looking at the ClawBot thing, right? That new thing that's coming out or that's out. And I think that's where people are gonna try and, try and figure out how do I build this into my daily life? Whereas before it was more research mode, maybe it's more execution. Like, how can I execute on this stuff?

I like that. Right? Yeah.

That's, that's my belief. How about you?

Yeah. Yeah. I like that a lot. How to move more from what is this and what do I need to pay attention to, to what do I build that makes my life better.

Yeah, how do I use this, right?

Yeah. So even if it's not, even if it's not commercially, even if it's just internally for yourself, like, you know, hey, I have 5 doctor's appointments that I need to make, can I ClawBot something that just like schedules my doctor's appointments for me while I'm on the Surf and Sales podcast. That, right, I would, I would want that. I would use that.

So, right, I actually had to make a bunch of doctor's appointments yesterday, as a matter of fact.

But we're at a world now, Richard, where you could argue you and I should not be spending our time making these appointments.

Well, I think that's the point of the use case thing of like you know, this comes back to the generational thing. We're growing, we're growing into it from the outside. We're not native. Yeah, right. Like, sure, you know, our kids are much more native social media. We were forced into social media. Now it's just a part of their day. Yeah, right.

Yeah.

Like, those things are just uniquely inherent to them. Whereas for us, we have to stop and actually think about it. Right, and make a conscious effort. And I think that's the difference, which will also be interesting at Surf and Sales generationally, how people see that, right? Like, how will, how will the, the old fuckers like me and the medium old fuckers like you, um, compared to the 20-somethings who come in and be like, they probably cloud-coded 20 things, and we'd be like, fuck, really? Yeah, not that hard.

We'll let them, we'll let them run this session. So hey, if you want to come to Surf and Sales— and you're an AI cloud coding wizard, maybe we'll give you a speaking slot.

We'd love you to.

At the event. So, all right, everybody, that's episode 480. We are 20 episodes to go till 500. Richard and I are going to be counting them down week by week. We'll see you all next time at the Surf and Sales Podcast.

See everybody.

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