Richard Strom joins Warren Kucker to discuss The Tools Changed, The Job Didn't: An Enterprise AE's Take on AI in Sales. Key takeaways include Sales Reps as Conductors and The Evolution of Enterprise Sales.
The Tools Changed, The Job Didn't: An Enterprise AE's Take on AI in Sales
with Richard Strom
"The tools changed. The job didn't."
About This Episode
The episode explores how enterprise sales has evolved over 15+ years, particularly through the lens of AI's impact on sales workflows. Rich Strom discusses his journey from cold calling to closing six-figure maritime deals, examining how sales tools have historically burdened rather than empowered reps.
About the Guest
Richard Strom
Enterprise SaaS sales professional with 15+ years of experience, progressing from cold calling to closing six-figure deals in maritime shipping at Sedna. Recently transitioned from sales management back to an individual contributor role.
Key Takeaways
- ✓ Sales Reps as Conductors
- ✓ The Evolution of Enterprise Sales
- ✓ The Impact of AI on Sales
- ✓ The Role of AI in Maritime Industry
Chapters
Show Notes
Stepping back from management can make a better manager later
Richard Strom is an account director at Sedna, where he sells into the maritime industry, and he has spent more than 15 years in B2B SaaS sales at companies including Bazaarvoice, Spredfast and Khoros. He started in project management, but three or four employers in a row moved him into sales within six months, which he took as a clue. At Bazaarvoice he worked as inside sales rep for a mentor, Tony Markovsky, and took over when Markovsky left.
Strom later moved into sales management and then chose to go back to being an individual contributor. Kucker notes that management is the right role for a rep less than half the time. Strom gives three reasons. A first-line manager's job is to make the team successful, and that takes a support network he did not have when he stepped up during COVID. He also had two young children, and he describes management as adding five dependents. He did not want to keep choosing between his daughter's recital and a call to close someone else's deal. Finally, he says time back in the seat taught him more than the management role did. He now believes he would be 50 times better as a manager than he was, because he has since watched many different leadership styles and picked up frameworks he lacked.
Kucker agrees. A good to great rep often out-earns their manager and is mostly left alone, while a manager with six to eight reps loses that flexibility to strategy meetings and trainings.
The old tools tracked the rep. They did not help the rep sell
Strom's early days were a spreadsheet, the Yellow Pages and a script, selling IT support services by phone into East London small businesses. The tool was a phone and a laptop with an Excel sheet. What actually won deals was getting in front of people. As a BDR at Bazaarvoice the work became more strategic, with a territory plan and bigger Nordic accounts such as IKEA, and email outperformed the phone.
Kucker asks whether the stack of the last decade, Salesforce, Outreach and the add-ons around them, paid back the time reps put into it. Strom says it did not accelerate his deals. Those systems were mechanisms for the company to control forecasts and manage a sales process. They were not a drag, but they did not drive efficiency for the rep.
Kucker takes the point further. The sales process has been over-tooled, and most of the tooling, a more robust CRM, forecasting, data analytics, serves executives rather than the people driving revenue.
Forecasting does not help you get more revenue.
In Kucker's view forecasting tells finance how much to spend next quarter. What has changed in the past year is that LLMs can pull structured data out of unstructured conversations. That means a rep should only touch the CRM when it helps the rep, and the CRM should fill itself from what already happens in the rep's day. Strom agrees, adding that forecasting matters to the people running the business, and it is a positive when the same signals also feed the rep's own process.
Call transcripts let a rep hear what the customer actually said
The most useful change Strom has seen is call recording paired with AI. Reps miss most of what is said on a live call, because the brain cannot track it all in the moment.
Even the best sales reps sit on a lot of calls and they don't actually hear the majority of what the actual customer is saying in the moment, right?
With the transcript, a rep can ask for every question the customer raised on a call, which shows what matters to that customer. The point, Strom stresses, is to help the buyer. Where the worst reps throw spaghetti at the wall, tools such as Gong let a rep pull the important points out of information that would otherwise sit in notebooks.
Briefing a CEO for an executive call used to take him three hours. Now it takes 20 minutes. AI produces the summary, and he reads it through his own lens, corrects it and adds what only he noticed, such as the moment he saw in a person's eyes that something mattered to them. AI will not pick that up.
He applies the same idea to follow-up. Strom keeps a personal rule that any meeting gets a follow-up email by the end of that day, summarising what was discussed and the next steps. His notes used to miss some key points or next steps. Now he asks AI for the key challenges raised and the agreed next steps. He believes it sets him apart from other reps, though he admits he cannot know that for sure. He recalls a story John Kaplan of Force Management told at a Bazaarvoice sales kickoff about a man running up a hill and the question of who else is doing it. The answer is no one, and that is where a seller differentiates.
Buyers research earlier, so plant seeds and keep watering them
Asked whether buyer behaviour has shifted over 10 to 15 years, Strom accepts the common view that buyers research more and arrive later. His response is to plant seeds. Pick a set of people who could get real value from the product and keep giving them useful information, even before they need it.
At the absolute worst, you could be an educator, right?
He bets on ten seeds and waters them often, so that when a need appears the buyer already has a relationship with him. People buy from people, he says, and he will not suit everyone. The trust matters most after the deal closes, when something goes wrong and the customer needs to know who to call. Building that trust long before an evaluation starts is the key.
Kucker frames this as AI amplifying the human relationship rather than eroding it. Prospects often arrive well researched, with two to four similar options. What separates sellers is who the buyer wants to work with for the long run and who will execute. At Sedna, Kucker notes, a sale is the start of a 10 to 15 year relationship.
In maritime, AI questions are about problems, not inspiration
Maritime shipping is an old industry, and Kucker asks how its buyers talk about AI. Strom says they are no different from any other industry. AI comes up in nearly every sales process, and demos land well, but he brings the conversation back to the buyer's problem. Asking a seller to show what AI can do in general is like asking a group of artists to paint a picture without saying what it should be about. For Strom it is education.
Kucker notes the tension. Salespeople are trained never to sell a solution in search of a problem, yet buyers facing a new technology may need vision. When he asks Strom how AI will change the AE role in three to five years, Strom says he does not know, which is the same position his maritime buyers are in. Kucker concludes that sellers may have to pitch vision more than before, which makes deep market knowledge matter more.
Strom expects reps to need AI enablement over the next year or two. He returns to an idea from a conversation with his colleague Molly: the rep as a conductor. A rep does not know everything, but brings together what customers, colleagues and experts across the business know. That includes selling internally as well as externally, and he sees these tools as serving both. Kucker calls it conducting a complex orchestra, selling $100,000 contracts to solve million dollar problems.
Full Transcript Show Hide
00:13 Warren Kucker: Hey there and welcome to another episode of Selling AI. Today we're diving into the evolution of enterprise sales with someone who's seen it all. I Rich Strom on the show today and Rich is a seriously seasoned account director at Sedna. But here's what makes Rich's perspective so unique. He's been in B2B SaaS sales for over 15 years, cutting his teeth at companies like Bizarre Voice, SpreadFast and Coros before landing at Sedna where he's been absolutely crushing it in the maritime space for the past three years. In today's episode, Rich and I are going to talk about the day to day of an enterprise AE and how it's fundamentally changed from about 15 years ago to what he's doing now. What AI tools are actually making him better at selling. But here's the fascinating part. We're going to dive into how like an old school industry like maritime is starting to ask for AI features in his sales conversations. We'll also get into where Rich thinks the future of enterprise sales is going. And we're super pumped to dive into these topics. So let's do it. Hey, Rich, thank you for being here with us today. Welcome to the show.
01:08 Richard Strom: Thank you, Warren, really happy to be here.
01:10 Warren Kucker: Awesome, man. Well, first things first. Give us a quick background. How long have you been in sales? was the evolution of your career? And how did you end up at Soudna and selling Maritime?
01:19 Richard Strom: Yeah, I'll keep it to the fairly short version, but effectively when I left university, I decided I wanted to get into operations or more project management stuff because it's a skill set that I feel like I had. My dad was very organizational and that. Every time I joined a company in a project management role within six months, they pushed me into a sales role. I was like, I don't want to be a sales guy. So I moved into another operational role within six months. They pushed me into sales and this happened three, four times. So was like, there's probably some kind of a clue in here. And I think what they were noticing were some of the things that I think are important in sales in terms of being able to listen and understand curiosity drive and some other things that I gained from kind of my background in childhood. So. I started out in sales in what I would call like a vacuum clean sailor, vacuum clean sales role, which is basically knocking doors and hundred dollars a day plus just trying to hit the phones. It was a numbers game, which teaches you a certain type of resilience and it's a challenging role. But it wasn't the enterprise role that I'm in currently. interesting as it was, I got headhunted into a company, SaaS business, Bizarre Voice. I had a mentor there, Tony Markovsky, that gave me a huge amount of confidence. I was his inside sales guy, BDR, SDR, whatever. And when he left, I took over the mantle and I guess the rest is kind of history. I've jumped to other sales companies, always on the SaaS side, mainly looking at communication, gotten into sales management as well, decided to go back into individual contributor. And now I'm here at SETNAS. Happy to explain a little bit about Y7 as well, is that what you were looking for anything?
03:18 Warren Kucker: No, absolutely. Let me ask, it's a conversation I have with lot of reps that management isn't always the ideal role. In fact, honestly, less than 50 % of the time it is. Why did you like dip back into being an IC?
03:32 Richard Strom: It's a good question. think one of the things that I noticed and some of the stuff I've listened to from podcasts and stuff is is having the support network around you to actually make sure that you take that step into first line management in a good way. And ultimately, if the first line manager's role is really to make the people that you work with successful, right? And if you can't do that, and if you don't feel like you're setting yourself up for success, then why are you doing it? It's just extra stress. ultimately, it's, yeah, you need a bit of guidance. Now, I did that under the umbrella of COVID and so it probably added an extra layer of challenge and complexity. But what I realized was at that stage of my life as well, I two young children, like you're basically adding five dependents, right? And for me at that stage of my life, it wasn't the right thing because again, I wouldn't be able to serve that team in the right way. If I had to choose between a... recital for my daughter and having to jump on a call to help close somebody else's deal ultimately in my own territory, like that's a tough challenge to be in when you want to be able to go support your child, right? And I feel like you still have some of those challenges as an individual contributor, but you control that in a little bit more of your own place. And also quite frankly, what I've realized after I moved back into individual contributor was while you're never ready to move into any position, I've learned so much being back into it that I am right now in a position where I would be 50 times better in a management position than I was before and I've learned so much. So quite frankly, I don't think I had all the skill set and the frameworks that I wanted to and I hadn't experienced that from observing lots of different leadership styles. So long answers to your question, but I think It's a combination of where you're at in your life, the control that you want, and obviously, yeah, you can earn just as well, if not more, when you're sitting as individual contributors.
05:50 Warren Kucker: Awesome. That's great. Yeah, the earnings aspect to it is the, let's say when you're an early in your sales career, it just seems like management's a better earnings path. Not always the case. Actually frequently a good to great sales rep is gonna earn more than management will. But it's an interesting to think about the flexibility, right? Obviously there's a little bit more control of your own territory. A good sales rep mostly gets left alone by management, right? So you have some autonomy. And then on top of it, You're absolutely right when you have six to eight sales reps and you're in like company strategic meetings and trainings and these types of things There's a rigidity to your day that you don't necessarily have When you're working your territory close your deals to work your territories you do that in whatever hours makes my sense So that's that's an interesting we should dive into like how you're better prepared Do you think now to go back into management if you ever to would a little bit later on? Cool, let's dive into a little bit of your experience though. You mentioned door-to-door sales. I had some experiences there. I worked at UPS. I hated it, but you had to go out and basically follow FedEx trucks and then hand them flyers and say, want these 37 packages. So let's talk about then two stages then, your door-to-door kind of sales days. Then the next stage where it was, let's say, inside sales. And what's the evolution to how you're selling now? And really in particular, how are you spending your day-to-day comparatively?
07:09 Richard Strom: Yeah, I mean, early days with just the door to door or just pick up the phone and call it was literally here's a spreadsheet, here's a yellow pages and go ahead and call because we were selling it. IT support services to East London with a slightly odd accent calling into a bunch of size businesses wasn't particularly attractive. And I've learned more swear words through that job than in any other. But I think it was much more of just a slog, right? Like you had a set template of what you would say or a kind of script and then you would just see if you could open a door or two because you just caught somebody in the right situation. I think the... The tools weren't necessarily there. The tool was literally a phone and a laptop with an Excel sheet. But what I saw was being successful was when I actually got in front of people. That made a huge difference in terms of just being able to win deals. I think the... the next phase of BDRing and inside salesing. mean, ultimately the tools at the time were also fairly basic, right? Like we wouldn't have a huge amount of different tools at our disposal. So the days would go about like some kind of a territory plan, some kind of a plan of attack. And it was a little more strategic than we had the companies we wanted to go out and get. And they were bigger in this case. Nordic accounts that we were focusing on, companies like IKEA, H a lot of other ones that you wouldn't hear. And so a lot of the time was spent researching, working with partners, working with the contacts that people in our business already had, and then effectively email. Email was a lot stronger at that business than... than phone call. And I think partly that was because one of our managers was very good at emails. And so he basically taught us how to write good emails and yeah, it was an interesting way to... So yeah, I think the evolution there was just a lot more... slogging it out, right? would be the way I would kind of say it. Maybe it was because I didn't know any better and at that time you were just left to slog it out to actually get somewhere. But lot of my success I think came down to... building strong relationships internally and building strong relationships externally in businesses. And so if you fast forward to today, I think one of the biggest differences is there's so many more tools at your disposal to be able to manage it. And when you have pattern recognition, because you've been in situations where you've sold to different people in different situations, you know which tools to use at the right time. You know that there's more access to tools. And I'm both a process guy. and a tools guy, like I love to be able to leverage this, the different opportunities. And so what it effectively does is it allows you to focus on the really important things because you can take your time away from some of the more... labor intensive work that you're doing. And I think that's the biggest challenge I'm seeing, right? Like you're getting insights, you're getting information, you're being able to then funnel that in a more effective way with the experience that you've developed over time. So I don't know if you agree, like do you have a different perspective on it?
11:00 Warren Kucker: No, so your experience is drastically different than mine, right? So I've always just run, let's say, a founder-led sales model. My introduction to, let's say, a traditional scale sales process was later in my sales journey. So I probably have a different perspective than you. so, interestingly enough, let's talk about tooling just for a moment then. Let's say this. So you mentioned this a decent amount. So compare the tooling that you had, let's say, two years ago. right, Salesforce, Outreach, a couple of other lay-ons, right, like those types of like platforms, right. That tooling compared to what you had 15 years ago, where I would say it was like Salesforce, but like base Salesforce as it was 15 years ago. Do you feel like that the time you put into the tooling got you the return that you would have expected? Or do you feel like that the tooling didn't actually make it that much easier to sell? Was it a drag? Was it an accelerator? Or was it neutral all along the
12:00 Richard Strom: I I don't think it actually accelerated deals in any way or helped me in that. was simply at that time, some mechanisms to be able to control forecasts and to be able to control the deals and to manage effectively a sales process for an entire company and a post sales process as well, obviously, and some other things. I'm trying to think back. It's one of those terrible things. The memory's completely shot, but like, I don't actually remember a lot of other tools like Sixth or other things like that. I mean, even in outreach, didn't have anything like that. Salesforce did at the time. And so it was very much some basic ones. it would be, I wouldn't say a drag, but it wouldn't actually drive any major efficiency. If you look at it today, and it might just be that either I've now been made aware of more tools or been allowed access to some of them. But there's a lot of actually very powerful tools with which you can manage your own sales process, your own life, your own processes much more effectively. I think that, yeah, I think 15 years, a long time has, a lot has changed. And then even in the last two or three years, there's additional things that are coming. If I was thinking about it earlier, actually it was, it's, funny because I think that evolution has always been taking place. Right. If you think about how important is. the mobile phone to a sales guy that didn't have a mobile phone before he had it. So he's not only sitting at his desk, like how important is, for example, the internet, right? Where before you'd have to do a lot more of your work with the top of funnel stuff by having marketing send stuff through to people. suddenly you've got this access to people being able to do a lot of research beforehand without that, right? And so all of this evolution is, we know that people are doing a lot more research before they get to us as salespeople. So the question then becomes, where's that productivity and where do we actually help drive efficiencies for them and using the tools that we have at our disposal? So yeah, I have a few particular ones that I think are really interesting, but they cross every kind of spectrum.
14:37 Warren Kucker: Yeah, so think there's an interesting point that's happened more recently. This is a common theme is that for a long time, so we've over tooled the sales process just in general. It's too complex for the people that are actually driving revenue for an organization. But I think the the mentorship that we've now been kind of alerted to is that like actually most of those tools were for what exactly what you said. They actually didn't help the rep sell better. It helped the organization understand what the reps were doing, right? So like more robust CRM, forecasting, data analytics. These types of things are all like executive focused, right? And not, it doesn't help drive revenue. I get asked about forecasting all the time. Forecasting does not help you get more revenue. It helps the finance team understand how much money they should spend in the next fiscal quarter or year. But it doesn't help a rep close deals for the most part, right? On the flip, I actually think the shift that we've seen over the past year, and I want to hear about a couple of these tools that you think maybe have helped you in this shift, I don't think it's that you didn't use them appropriately or unaware. I actually think that LLMs have enabled us to get data out of unstructured data in a way where the reps can be focused on processes and tools that actually help them win more work without having to interact with the tools that the organization needs to know, needs to have in order to know what the reps are doing or how to forecast. Those should now become separate, right? So like your interaction with the CRM should only be if it's helping the rep. And honestly, most of time it's not. The CRM should get its data from all of the inputs that are just happening within the rep's day rather than those manual inputs. Have you seen, like in the past year or so, a couple of like areas where the tooling has taken a leap and it's actually helping you close deals?
16:26 Richard Strom: I definitely think so, but I completely agree that the power is when these tools are connected and they send the signals to the... whichever tool you're gonna use as your source of truth for some of that. And I completely agree that some of the forecasting tools and all of those might be more for the executives, the people that are managing the business and it's important for them. But if it feeds into the other signals that we're using to be able to drive our business, our processes as enterprise reps, then that's only positive, right? So I think some of the... It really, it's quite broad in terms of the types of tools, right? Some things like just the call recording and the ability to get the transcripts out and do very quick research on what's going on. Like, it's completely true that... Even the best sales reps sit on a lot of calls and they don't actually hear the majority of what the actual customer is saying in the moment, right? Because they just don't have time to be able to do it and the brain doesn't function that way. So the ability to listen back and actually look into these things, or even just simply saying, Hey, can you list all the questions that this customer was asking on a call? It gives you all of the intent of what's important to that customer. And that's not in a way to be able to manipulate them. It's in a way to be able to help them because otherwise, as sales rep, what you're doing is just kind of, ultimately the worst sales reps are just throwing spaghetti at the wall and hoping something sticks. But with these tools, be it a gong, a jiminy, a kaya from outreach, whatever these tools are, you're able to effectively understand what's going on with those transcripts then. You feed them into to AI, right? And so you're able to then take masses amounts of information, which would effectively otherwise be in notebooks and be a little bit more. Probably nuanced to what you think is important, but you might not have heard everything and pick out the most important bits. Therefore, when you ask your CEO to jump on an executive call, a brief them, you're not spending three hours trying to create that briefing doc. You'd spend 20 minutes, right? You've got. AI to summarize all of it. You then use your own lens on it and read through it, change it and like improve it because it's never going to be perfect. Pick up the things that you did write in your notebook that were very important that AI might not have missed, but didn't understand the context or the kind of... I see that person's eyes. This was important to them. It's not something that AI is going to pick up. those things are all joined up, right? And now with those signals, you're able to send that through to various different forecasting systems and that. So that's definitely one area that I'm seeing is basically allowing you to spend a lot more time focused on helping the customer at the end of the day or prospect, whichever.
19:31 Warren Kucker: Great, understand. Okay, let's pivot a little bit. Let's talk about the buyer's journey a bit. So like first things first, just generally, have you seen a shift in buyer behavior over the past like 10, 15 years and how they want to evaluate a solution, how they want to make a buying decision and how they want to execute a deal? Has there been a shift?
19:54 Richard Strom: I read about it and I don't, cause I, I'm not necessarily, I don't ask them directly about this. It's probably an interesting question to ask them, but you, the common thread is yes, people are spending more time researching and coming to you a bit later. My take at least in the last four years here with Sedna and even before that is you want to plant seeds, right? And those seeds are ones that somebody might have already planted a seed themselves because they've been doing research or they might be an intrinsic buyer. And so they already know what they're looking for and they're quite knowledgeable. Then they'll get quite far down in the line in terms of what they're looking to buy. So I think that there is a lot of that kind of people that are doing more research, but if you're not doing the seeding, as in like being able to continuously build the relationship, provide good information to the ones that you know are important, then you're kind of missing out on an opportunity to help that buyer as well. Because ultimately, if you work for a company that you believe has a good product that actually serves a purpose that that other people in their position could see a lot of value on. At the absolute worst, you could be an educator, right? Like you could be a professor saying, listen, if nothing else, you're gonna have three or four different companies that you're gonna look at for these kinds of solutions. It might not be relevant right now, but one day it will be. If nothing else, I'm gonna put my bet on these 10 guys or these 10 seeds, and I'm gonna water those quite frequently, right? And if you're able to do that, then those will at some time blossom and they might've done their own research as well, but if they know that they have a relationship with you and of course, coupled with it, they can do their own research as well with a good marketing engine, whatever, then you're in a much better place. And so my perspective on it is maybe they are doing more of that research beforehand, but that shouldn't stop you from... genuinely wanting to be able to connect to the people that want to learn. And that's not everybody. And people buy from people. like, I'm not everybody's cup of tea. And the way that I work with people isn't everybody's cup of tea, right? But I am somebody else's. So right, if you find the right people and the people that you trust, then I think there's a really good balance there. yeah, I think it's a... I think they definitely are doing more early, but at the end of the day, comes back to for me, people buy from people, right? And so, yeah, I think what has become quite clear throughout my entire career is it's not so much only the sales cycle and having trust in that person at the sales cycle, but it's when you've closed the business, it's... who do I call when I really need some help, right? Things aren't going right, this wasn't what I was expecting. If you've built that trust, if you've built that trust way before the actual even evaluation started, then you know that you have a go-to person to solve that problem. And that's what I think the key is, right? It's that genuine, honest relationship for longer periods of time. And it's not possible for everyone, right? Because you have... If you have a lot of people that you start working with, then your bandwidth isn't there, right? But that's where some of these tools, I think, are really helpful to be able to help serve these people that you're working with.
23:40 Warren Kucker: So it's interesting, this is another common thread that where the concern is that like LLMs and generative AI are going to tear at the threads of the human relationship and human experience, right? But we talked about this a few times and this is a new way I haven't thought about it, is that actually like some of this technology should actually amplify human relationships, right? In this case, the scenario would be if you're expected to know everything about the company that you're talking to without. asking them. Any public information before discovery call, you should know at this point. It's table stakes to do that. On the flip, prospects are more and more well researched and they have two, three, four solutions to their problems that are probably relatively weighted equally. And so it's no longer like the ROI discussion that's been typical or the discovery phase that could take meeting after meeting to truly uncover problems. The human to human relationship actually gets amplified again. And it's not, um, without reason. The reason actually is that like, who do I like to work with? And who am going to continue to work with? When you're selling someone at Sedna, you're building a 10 to 15 year relationship with them. Who's along for the ride for that relationship? But secondarily, how am I going to execute, right? Like, and the execution is just as important as the software. So like, it's an interesting perspective that if you peel away at the busy work that we used to have to do in order for buyers and sellers to come together and say, I have something that you want, and you have something that will solve my problems. We can peel that away and get right back to the, can I make your life easier, that kind of like human bonds? It's kind of interesting.
25:16 Richard Strom: I have a good example of that, at least from my own perspective. I have an internal SLA for myself of every day, if I have a meeting with somebody by the evening, by the end of that day, I have sent a follow-up email. For me, it's a, not only a respect thing, but it's a kind of ideally summarizing what that meeting was about and kind of clearing, being clear with the next steps. You can call it kind of almost secretarial or being able to have the notes of the meeting. In the past, if I did that, and I think even when you and I worked together at the beginning of our time, I would spend a lot of time doing that, but I wouldn't always have time to get all the notes perfectly written. So they were maybe not as complete. So it might be that the key summary points weren't there, or the key next steps I might have missed a few. What AI is allowing me to do is it's allowing me to grasp the majority of the stuff that I've missed really quickly and pre-populate that with, hey, these are the key points because I can ask you, hey, what were the key challenges or what are the key things that we're asking about? What are the key things that we decided we're going to do next? And so it's easier for me then to get that out. That is a really, really nice thing for the prospect to have because it basically gives them a meeting notes of things that I believe I'm gonna do better than another rep, right? And I don't know that for sure. And I don't, I can ask that question post sale sometime. But I think that's a differentiator, right? And one of the... I was at a sales kickoff many years ago at Bizarre Voice. We had John Kaplan come in from force management and he tells a story about a guy that walks up the hill, runs up the hill, right? And the question is like, he didn't want to do it anymore, but he came across one of his friends that was running with him. The question was like, who's doing this? And there's no one, right? And that's where you differentiate yourself. And so if you can use these tools to differentiate yourself by being able to provide value, That's the human element of being able to create a difference that helps somebody, right? And that, I think that's where I see the biggest value here.
27:36 Warren Kucker: That's a good way to put it. That's good way to put it. Cool. Okay. Let's talk about some other, let's say, buyer journey item here. currently you're selling into maritime shipping. Maritime shipping, it can be a bit of an older school industry. It's 150 years old just in general, right? So you have that aspect to it. How are they starting to talk about AI in products? Are they begging for it? Are they asking how to do it? Are they lightly touching it? Are they skeptical? What's happening in the buyer journey for someone that like this group of folks that may not be as like AI willing?
28:14 Richard Strom: I think it's probably the same as with most. industries and people it very very much varies right like you get you get the the groups of people that are super interested in what's going on and some that are very very forward thinking and have ideas of what's going to happen there's some people that are are like hey just tell me tell me what I should know and like using it as a buzzword so I don't think it's any different than any other industry in that I've worked with in terms of the fads that come up and people are talking about. I'm not calling AI fat, let's just put it that way, but if you get my kind of drift of like there's these big things, a lot of people, it comes up in pretty much all the sales processes. The question is like what are you guys doing on an AI side? Show me the example, clear-cut examples of it and generally when we show it, it's really interesting and cool. It comes back to a simple thing though, it's like What do you want it to do? Like what's the problems that you need fixing? And then we can talk about how AI might be able to do something about that. But if I'm throwing a bunch of spaghetti at the wall to try to inspire you around what AI is capable of, it's basically like saying to... a bunch of artists, hey, paint me a picture. like, yeah, sure, I can paint you a picture, but like, what's it gonna be about? So I think what happens a lot is, hey, tell me a little bit about what you guys are doing on AI, inspire us. And I think, again, I don't think the maritime is any further back from my perspective. It's just an education piece. And if we can help educate them, that's great.
30:03 Warren Kucker: Totally agree. And you know, it's like the technology itself is the first time for a long time opening up some new frontiers, right? I can't imagine, I wasn't around and I don't think you were, but when desktop computers at the office started to come out, right? Like, and you were doing that, people were asking like, hey, tell me what this desktop computer could do. What are you doing with desktop computers that you weren't doing before from a service standpoint, right? Like, I can't imagine this. So it's kind of a new problem and it does require some inspiration, but as salespeople, we've always kind of been trained. not to do that. Inspiring with product is founder's job early stage, right? But like a solution in search of a problem never works well in sales. So it's an interesting juxtaposition that we're in right now. Okay, let's dive in here. So I say fast forward three to five years. What do you think might be different? What do you think, let's say, generative AI might be doing better for sales reps like yourselves that it's not doing now? How do you think the role might evolve?
31:02 Richard Strom: It's a really hard question because if we look at how fast it's developed in the last six months or nine months even, it's, I don't. I'm not the visionary and I don't do enough research to be able to understand that direction in my head. All I can kind of see in the shorter term is it's about applying it at the end of the day. And it's about understanding how it's applied in an organization. So some of my thoughts are like, how much is the individual rep going to be building these different agents and different ways of working, how much is that responsibility is going to fall on to the sales enablement team or other teams that might not even be there yet? And then it's about maybe learning the prompts and being able to do that in a much more effective way. Is there going to be a point where like even that is going to not necessarily be required because there's going to be some... evolution on that that then becomes you don't actually need to do any of that prompt work either because you've basically gotten to a point where most of that's already done for the key points and then you have to think about something else. I genuinely see at least in the next year or two that the sales reps are going to have to be educated in terms of how to use it. And that's going to come from a sales enablement perspective. so I think that there's going to be a pocket of sales reps that are gonna wanna be able to do things themselves. And there always is that kind of early adopters and they're gonna be taking and pushing the boundaries. There's gonna be the laggards that are not going to wanna change anything. And some of them will continue to be successful in the way that they worked and maybe just take a few bits of it. But ultimately, I don't have any vision of exactly how it's going to completely change in three to five years. Partly that might be because right now in my role, I'm a little bit more focused on how do I use it in perspectives that I kind of understand. And I'm still early in that journey, right?
33:20 Warren Kucker: Now it's interesting, there's a sales lesson in there and the two answers you just gave back to back are a good combo for salespeople to keep in mind, right? So like one, hold on one second. So on the first hand, you have calls with folks in maritime, and we don't want to have a solution in search of a problem. And you're like, hey, great, it's like a painter. You want me to paint something? Tell me what you want to paint. On the flip, let's talk about you as a buyer of software and sales. What problems do salespeople have? I need more pipe. I need to close more of that pipe more regularly. Cool. There's three problems in each of those sections that need to be solved that could be solved for it, but it's pretty finite and it's been the same problems for a decade, right? Cool. Rich, like how do you think AI might change your role? Like how can I help you three years from now to solve those problems? Honestly, I don't know, right? Like I'm not the visionary in this space. Our customers are in the same boat now, right? Like it's new. I don't know where it's going to use. And in maritime, what do they care about? I want to drive more revenue. I want to, and I want to cut costs, right? So like. Tell me, based on what you're looking at in communication platforms, how can I do that? Salespeople might actually have to step into an uncomfortable role of pitching vision more than we used to. Less about problem, focused, and more about vision. And maybe my last point of that is actually it's going to make it even more important that you understand your market thoroughly. Rich, you've been doing this for four years. Your first year, you probably didn't understand how to drive revenue in Maritime. But now you really do. combining that, what can you be doing in AI and your communications platform to drive new revenue? We're going to have to be the ones that kind of be at the forefront of that. It'll be an interesting problem to solve for our buyers.
35:05 Richard Strom: But, I think you, you had a good conversation with my colleague, Molly, who you had another, one of these with around the kind of sales rep being a conductor. And, and, and we don't know, we don't know everything. We don't know a lot at all. And a lot of times we know probably the least of a lot of people, but we are. The word director was used a long time ago and it's sales director, which is like, sounds like a pretty high title for somebody that's effectively is sales executive or somebody that love, but it is conducting. Right. And so it's, it's learning. What are other people doing? Other one of your customers, other customers that your colleagues are bringing on board and then sharing that knowledge and that then bringing the expertise of other people in your business. And that's where you're actually just, you're conducting, right? Like you're learning, you're developing and. And I think that's another important role that is oftentimes forgotten is how important selling internally as well as externally is. And so these tools are not only used to sell externally, they're used to be able to sell internally as well.
36:13 Warren Kucker: Nope, totally agree. That's a really good way to put it. You are absolutely conducting, right? A complex orchestra to solve big problems. You're selling $100,000 contracts to solve million dollar problems, right? It's not something that can be done in a day. that's awesome, man. Well, Rich, I really appreciate you providing your experience. Tell us, you have any events you're going to, anything specific in maritime, anything you're focused on in particular in your role right now at SEDNA?
36:37 Richard Strom: We've got an IE week, International Energy Week, 10th of February in London, which is a good chance to meet people in the industry. that's coming up. We have our customer event in Copenhagen on the 19th of March, I think it is. I'll double check that. So that's another great chance to be able to meet. There's plenty of opportunities in shipping to be able to go out and meet people as well. So those are some of the events. think generally focus is, we talked about it before, for me it's still like, do I create a repeatable model? and using frameworks and processes and continue to learn and kind of develop what I'm doing. it never stops, right? So those are the kinds of things that are constantly on my mind is how to continue doing that. And that's fun.
37:36 Warren Kucker: That's awesome, man. That's really cool. Well, listen, Rich, really appreciate taking the time. Thanks so much for taking time out your busy schedule, and I look forward to speaking again.
37:43 Richard Strom: Appreciate it, one, always a pleasure.
About the Host
Selling AI is hosted by Warren Kucker, founder of Topiq. Each week he sits down with revenue leaders, founders, and operators to unpack the strategies, tools, and stories behind selling AI products and using AI to sell smarter.
Warren Kucker
A revenue leader and entrepreneur who founded Basiq.work, focusing on conversational AI for sales teams. Previously served as VP of Sales and CRO at Series B companies, scaling revenue to $2M+ quarterly bookings. His exits include Shelly.ai (ML email automation) and Boxton (digital freight platform). Started his career at Apple managing a $100M shipping efficiency program.
Related Episodes
Your Buyer Doesn't Know What to Ask For Yet
with Michael DeLeonardis
Michael DeLeonardis, chief revenue officer at Verity, explains how selling autonomous warehouse drones differs from selling software, and why AI has pushed enterprise sales back into a demand creation cycle. He and Warren Kucker discuss deep discovery around physical constraints, win-loss analysis from call transcripts, deliverable-based selling that guides the buyer through each decision, a client success role that spans pre-sales and post-sales, and why industry expertise and a LinkedIn presence matter for sellers.
Great Marketing Should Reduce Your Sales Calls
with Jen Chaney
This episode explores how AI influences demand generation strategies, examining contemporary approaches to buyer research and the transition from pursuing lead volume toward accelerating pipeline velocity. The discussion covers AI's contributions to content creation, individualized outreach sequences, and the integration of marketing and sales functions for revenue growth.
A Champion Isn't a Person — It's a Behavior That Shows Up When There's Good Friction
with David Weiss
David Weiss challenges conventional sales approaches by distinguishing deal management as a separate discipline from sales methodologies. He reframes champions as behavioral patterns rather than individual contributors and examines how behavioral shifts manifest across sales cycles.