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MarTalks: Cracking the Code for those first deals: Enterprise Sales for Startups

• Darrell Rosenstein

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In the latest *MarTalks* episode, I had the privilege of hosting three enterprise sales powerhouses—Brad Habansky, Chris Sterbenc, and Brian McGlynn—to discuss one of the most daunting challenges for startups: landing that first big deal. These seasoned pros shared their war stories, scars, and hard-earned wisdom on navigating the complexities of enterprise software sales. Here’s what stood out:  

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### **🔍 Selling Innovation is Hard Work**

Brad Habansky recounted his early days at CommerceTools, introducing "composable commerce" to a U.S. market that had no idea what it was. Before he could even pitch flexibility or scalability, he had to convince prospects why they should trust the cloud—a revolutionary concept at the time. His journey was a masterclass in persistence, education, and rapid iteration.  

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### **📈 Iteration is Key**

Chris Sterbenc shared how selling for startups often requires constant refinement of your pitch. Early on, parts of his presentations fell flat (I hate it when that happens) —but by analyzing what resonated with prospects, he adapted quickly. As he put it, “One bullet point on slide five might eventually become half your deck.” Rapid iteration isn’t just helpful—it’s essential.  

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### **🛠️ The Right Team Makes All the Difference**

Brian McGlynn emphasized the importance of hiring entrepreneurial sales talent who can navigate uncharted territory. “Your first hire isn’t just a salesperson—they’re an explorer,” he said. But it doesn’t stop there; investing in marketing and technical support is equally critical to set that salesperson up for success in a competitive market.  

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### **🚀 Leveraging Accelerators**

Chris also highlighted how startup accelerators like Plug and Play and Engage are game-changers for startups looking to break into enterprise accounts. These programs provide access to innovation teams at Fortune 500 companies, opening doors that are often shut to smaller players.  

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### **💡 Key Takeaways for Founders**  

1️⃣ **Educate Your Market:** Selling a new concept often starts with teaching prospects why they need it in the first place which requires marketing to prepare the ground for sales

2️⃣ **Iterate Quickly:** Be ready to refine your pitch after every meeting until it clicks. Encourage experimentation and celebrate those failures! 

3️⃣ **Find the Right Talent:** Your first sales hire needs grit, curiosity, and an entrepreneurial mindset to succeed in uncharted waters, like a pirate…😊

4️⃣ **Invest in Marketing:** A strong digital presence is non-negotiable when 70% of the sales cycle happens before a prospect even talks to you.  

5️⃣ **Leverage Accelerators:** Programs like Plug and Play can help startups land pilots with major brands and expand into enterprise accounts. 

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Closing that first deal is tough—it’s a gauntlet of education, iteration, and persistence. But as Brad, Chris, and Brian reminded us, it’s also one of the most rewarding milestones for any startup.  

💡 What strategies have worked for you when closing your first big deal? Let me know in the comments!  

 #MarTalks #EnterpriseSales #Startups #ComposableCommerce

Rosenstein Group: martech & ecommerce executive search

Rosenstein Group is the only martech-specialist exectutive search firm. For over 20 years, we've been matching leadership talent in sales, marketing and customer success to pioneering startups in ecommerce, supply chain and sales enablement, and for digital agencies.

Our experience with recruiting e-commerce technology leaders for companies like SAP Hybris and Demandware has established us as an authoritative and trusted liaison for startups seeking their first sales leader, and scale-ups on their way to IPO.

Visit RosensteinGroup.com to find out more.

SPEAKER_04

Welcome to Mar Talks, the number one podcast for e-commerce and marketing applications. Martalks is devoted to covering the latest technology developments that drive the global commerce ecosystem from advertising to last mile. Enjoy all of our content at Rosenstein Group.com slash Mar Talks-Podcast.

SPEAKER_02

Well, good morning, good day, good afternoon, whenever you're listening to this. This is Mar Talks. I'm your host, Joe Rosenstein. Mar Talks is where we discuss contemporary issues in the e-commerce economy. And today we're going to be talking about closing that first transaction for uh a startup, which is a momentous occasion. And for that, we're joined by three folks that have done it repeatedly. Uh Chris Sternbeck, Brian McGlyn, and Brad Habansky. Thank you so much for joining me today, fellas.

SPEAKER_01

Happy to be here. Thanks for inviting us.

SPEAKER_02

I uh I I I could go into some detail here for each of your backgrounds, but rather than you know uh essentially make stuff up, why don't we uh hear from just straight from the horse's mouth? Uh Mr. Hibanski, tell us a little bit about yourself.

SPEAKER_03

Uh well, I've been in tech for a long time. Um I uh also started a few businesses of my own, so kind of an entrepreneur you know on the side. Um but uh spent a lot of time in Oracle and Salesforce, but then it started doing a lot of startups uh or you know early stage, um in particular uh you know commerce tools most recently, well uh eight years ago um when they first started here here in the U.S. Then moved to ElasticPath, another commerce vendor after that, and now I'm with uh in River today.

SPEAKER_02

Fantastic. Christian McGlenn.

SPEAKER_01

Yeah, kind of like Brad. I've been in uh commerce for a while. I've started a few businesses on the side. So I've been I've spent a longstead at a company called Autonomy with uh a lot of interesting lessons learned there, probably worth an entire podcast on itself on that one as well. But uh really a lot about bringing new products to market. So I've learned a lot there, was at a small startup, lipy.com, intellectual property space, uh, with one of the first AI solutions to market. So I had to bring a new product and a new approach to market, uh, and then Intrashop, where I led the Americas business and really had to reboot the business as we went in back in uh the late uh 2010s. Uh after that, Cobello, and then at a brand new venture uh will be released called Wealth Write Up. So a wealth tech company that I came in recently to lead the the organization and take a brand new product, a new company to market. So uh I've got lots of scars. I won't show anyone the visuals of those, but uh lots of lessons learned and scars of I can tell people what not to do, and through all that, maybe something what you can do will come out of it as well. So uh yeah, hopefully a little background on myself.

SPEAKER_02

Well, thank you very much for restraining your hideousness. That's very uh congenitive. Thank you too. Well, Chris, Mr. Sternbeck, let's let's let's tail off with you. All right. What's your story, man?

SPEAKER_00

Well, you know, interestingly, I gotta go on with the SCAR uh theme here. Uh 30 plus years at startups, uh, a lot of mistakes made along the way, some victories, and uh a lot of learning has happened. Uh Silicon Valley startups primarily, uh currently three years now CRO at Learn to Win, which is an ed tech play, and uh it's very relevant because we're selling primarily to large commercial enterprise and the uh U.S. military, so we had to go through exactly uh the things that we're about to chat about today at this company.

SPEAKER_02

Well, fantastic. Well, again, thank you for joining me. Uh you grizzled veterans, you scarred you scarred enterprise sellers. Uh you know, I I one of the most common searches that I've had over my 25 years in recruiting has been working with a founder who needs to hire their very first sales executive because they want to sell a product. And in enterprise software, we're talking about an initial transaction and the hundreds of thousands of dollars. Could be over a million, but most of the time it's in the hundreds of thousands of dollars. It's a complex sale, it's a multi-phase sale. It in today's marketplace is handled by a committee of buyers on your client side. Five, seven, ten people have been in the room that each need to be engaged, each have agendas, each have uh veto power in many cases on a purchase. And these founders need to hire somebody who can run that gauntlet and get their paper to the promised land and get some ink on a contract and deploy that solution for that client. So my first question to the group, and we'll start with Brad, is you know, you you actually sold uh commerce tools initially in the United States when nobody had heard of composable commerce. Like, what the heck was that? Uh what was that like?

SPEAKER_03

Well, it was hard. I mean, uh I think that's the first thing is it is really hard. I mean, it's that that's that that's the the first piece of it. Um I think Brian, you mentioned you were in Inner Shop too. I mean, I think that Silicon Valley for commerce is really Germany, you know. If you think about where all the commerce platforms are coming from, you know, um, and uh I would say I was a third U.S. employee. Um, and at the time I started, there we had some German customers, but no one that anybody here had heard of. Uh, so it was essentially, you know, starting Greenfield. We have, you know, um uh so we couldn't really use any of the references that we had in Germany because no U.S. companies have heard of these companies. It was more of a mid-market Homer Tools is a mid-market solution in Germany when it started. You know, it wasn't what it is now. Um I would say the hardest part for us is um, you know, what's interesting is Brian mentioned he was an entrepreneur retour too. Um, I think that's you need that kind of mindset to start. Um, you got to know it's gonna be hard. You gotta be able to do it on your own. Um, but selling composable commerce in the early days, I mean when I first started, it wasn't even selling the mock stuff yet. Because that we we we came up with that later on, and it was more of a marketing kind of strategy. And then in the early days, it was just trying to sell a customer on putting the commerce in a cloud in the cloud. Because at that time, most of the commerce platforms were not uh SaaS solutions. They were they were either on-premise or they may have been hosted in the cloud by somebody, you know, but it's just a hosted solution. You know, so you really had to say you had to sell them on why cloud first. You know, why put in Google? Why now it sounds funny to say that now because everybody puts everything in Google or AWS or Azure. But at the time, so that was see before I could even sell them on mock or composability, you had to sell them on why put something in the crowd, the cloud that's that critical. So we started there, and then we learned that we had to learn a lot about the cloud. You know, AWS, I mean our we were in Google, so we had to learn a lot about Google. We had to learn a lot about DevOps, about how to deploy into the cloud, because you had to explain and educate a customer on if they're gonna go to the cloud, and they had to have a lot of experience with it. How are they gonna have deployed the cloud? How are they gonna be able to deploy our software to the cloud? So we learned really quickly that I had to know a hell of a lot more about than just my product I'm trying to sell. We had to know the whole ecosystem. So the cloud ecosystem, then the composable, and then all the CMSs, all the search engines, all the the customer looked to us to be educate them on this market, you know, because they didn't know anything about it. So we learned a lot of things really quick. Like it's a headless platform. We're trying to go after ATG customers and website. We get them all excited, and then we realize, wait, they haven't they haven't decoupled the front end from the back end yet to go headless. That's a 12-month project. So yeah, they want to buy us, but now I gotta wait 12 months to then decouple it, and then I can sell too much in a year and a half. You know, so then we started saying, okay, let's go after ones that already have it headless, you know, it's just to save that time. You know, so but it's it's constantly learning, and honestly, it's it's screwing up, it's making mistakes, and then it's it and it's it's it's adjusting very quickly. Like, I mean, we I mean, I'm with Kelly and I started. Kelly's our chief product officer at the time. We would go in with a pitch and a presentation to one customer, and we'd walk out and it didn't work, you know. But they didn't go over well. So then we back in the car, we light it, we do it, we try to get, you know, and we do it over and over. Eventually you you find one that does, you know. So it's it's it's just iterating quickly and learning and learning it, you know, failing fast. Like the almost like doing software development, right? And that's and that's how we did it. Yeah. Um, but then when you got to the mock stuff, I mean it it started getting better, but then no one knew what it was. So we created that the the whole mock alliance and that sort of thing. But by that time it had kind of, you know, it was starting to go, you know. But the early days, I I'd say were hard. I mean, I w I think we sold one one deal in the first year, you know. Um, and that was lucky, I would say. I mean, if I'm honest, right? It was lucky. Um and uh but I think I think that's part of it too. You've gotta you've got to find their the right customer and the and the right champion in the account that can really that's willing to take that risk. Because buying commerce tools, you know, eight years ago, wherever whatever it was, was a risk. I mean, because the you think about it, it's Oracle, IBM, and SAP, you know, or with Hybris, where the the your inner shop are all well known, big, you know, you go out and say, hey, I want to move half a half a million, half a billion or a billion dollars of revenue onto commerce tools, you know, which no one had ever heard of. That's a the person who does that, makes that decision eternally has gotta have a lot of conviction behind it and gotta be willing to lose his job, you know, if and he's wrong or she's wrong. Yeah. I could keep talking, but I want to talk the whole time, you know, stop.

SPEAKER_02

Yeah, I uh you know, it those are some gems, man. I love that. Because when you started out uh with commerce tools, most of the 18 people that I put to work at demandware were still selling Salesforce for commerce, which was still demandware at the time, which again was the first cloud-based uh platform. And even then, not not a not a headless solution. So you you you addressed the the big enchilada in for for enterprise software sellers is that evangelistic sale. You know, nobody's heard of your company, nobody's heard of your solution. You've essentially you you hope you come in with something that the client really is experiencing a problem they're aware of. They already had a commerce platform, they were already selling online, so they had a budget for your solution. It was just this is a new format, this is a more capable solution, this is a more flexible solution. But but and even in that situation where the clients had been through buying cycles and were utilizing a product that competed with your own, you had to go through the process of educating them about the cloud, of educating yourself about the limitations of your technology, about when a client was ready to buy your solution, about what building that pitch. What was that pitch? How many times does it fall flat? How many times do you, you know, Kelly's a brilliant guy. The two of you in the room talking to a customer, you think anybody with half a brain is going to want to buy from these guys because they know what they're talking about. They're they're very educated, they're so very spooled up. It's like, nope, maybe not. I mean, and and at that point you had two decades of experience. Like, it it's a tough nut to crack. But you know, I mean, even worse when a client calls me and says, I need to hire my first customer, my my first seller. And I asked them, Well, who are your competitors? And they say, Well, we don't have any. Like, oh great, terrific. So there isn't a there isn't a budget on the planet for your solution. Your clients don't even think they have a problem. So they're gonna have to start from absolute scratch on that. So if if uh you know, Chris, you've been in that situation. You've you've been the guy that's like, hey, I got a problem I want to solve for you that you don't even know about. What's that like?

SPEAKER_00

Yeah, no, great, great, uh, great question. And going back to uh a couple comments about messaging. Yeah, you'll go and give your pitch, uh, and parts of it resonate, parts of it totally fall flat, and just that rapid iteration where you're you're looking for that vein of gold. What was the part they really got their attention? And you know, over time you find out that like you know, one bullet on slide five winds up being half your deck about a year later. That was that was I thought I was solving this problem, but it's actually this other screen over here, and then if you start training it out, and and you you know, they're completely minimized and drop what your original storyline was. And um, so yeah, that that totally that process nails it exactly, right? And then the uh the other thing is we've never heard of you. Uh, you know, potentially, you know, we we don't know that we have that problem, and so you're you're fishing around for that. The uh two things that I've learned the last couple of years that were kind of new and different, um, the classic you know, pilot program or POC with the land and expand, um, that's been around forever, and we're we're doing a lot of those in a large enterprise. We have found very few uh big commercial customers that would bite off a giant chunk right up front, right? Um, but they're willing, you know, to spend a little bit of money if they've agree that they have a problem and they think you can solve it, as long as you frame it properly. Good success criteria agreed upon up front and demonstrate ROI, right? And try to limit it to two, three, four months potentially. Um we've had a lot of success with that. Um the other thing though that's changed is interesting is that there's a lot of these startup accelerators out there now. And I don't know if you guys have had experience, you know, the Y Combinator and Plug and Play. And it's interesting, they you know, they got started really as sources of you know, seed money, venture capital, maybe access to mentors. But they've they've really upped their game the last two years in terms of providing structured access to innovation teams in large fortune companies now. I'll give you one example in particular. There's a group called Engage out of Atlanta, and they're a venture capital firm also. Uh, but what they've gotten together is 17 of the largest corporations in the state of Georgia that have all paid into this program. And these are large companies that self-selected, like, I want to talk to startups, which is one of our biggest barriers that we have today, right? Most big companies are like, you're the flea MIS, I'm not gonna talk to your company. I never heard of you. These are companies that are like leaning forward, going, there's a lot of innovation out there we want to grab on.

SPEAKER_02

You're an aggressive little bugger, too. You're an aggressive, like you won't leave me alone.

SPEAKER_00

Exactly. So stay still here. Yep. So we went through the program with Engage. Uh it was basically it's a one-year program, and we are just completing it now. Um, but it's like it's Coca-Cola, it's Chick-fil-A, it's Georgia Pacific, it's Home Depot. I mean, these are giant great brand names, and they've got dedicated innovation teams that are looking at tech like this. And then the thing that's interesting is your pitch changes dramatically because I'm sure you two have experienced this as well. We're talking about that pitch deck we just did, we're solving an operational business problem for somebody. Innovation teams is kind of interesting because they don't have that exact problem, but what you're trying to do is train them to identify where you can help with somebody with that problem inside the big corporation, and then frame what you're doing in a way where they can convey that message and get that internal customer excited. Um, and so we've had some really good success with that. And um, as a result of our experience with Engage, we've gone deep with plug and play as well, which is now multinational with like 30 locations around the country, and they've broken into industry vertical actually. Sorry, what does plug and play do? Plug and play got started as like a we work for startups where you could get a cheap office space, access to a printer, a coffee machine, and a bunch of other like-minded, crazy people. And they've since expanded. Uh, the founder actually housed Google in one of their first offices, and he's had several big wins, and so he keeps plowing that money back in. And now it's uh it's a venture capital firm doing primarily seed and early A. Uh, they also have locations around the country where you can go rent a cheap office space, the WeWork model, right? But the big thing that they've established is this industry vertical play where they've got they've got a fintech location, it's centered in um New Jersey. They've got uh they've got a Health Tech one, they've got uh the supply chain one is headquartered in Bentonville, Arkansas, thanks to Walmart, right? And they've got these anchor clients in each one of the verticals, and again, these are forward-leaning companies with innovation teams that want to talk to startups. And so um our current platform is a horizontal play, it's ed tech, it's training. Um, we our first entrant into uh plug and play was in supply chain. And so we're working with companies that are like big freight brokers and things like that Nolan Transportation Group, AIT Worldwide, UPS, right? But we've gone horizontal and now we're in like we're in the health and pharma space now, and so we're getting access to companies like Glaxo and Regeneron and Navartis, and we've kind of worked our way across these silos. So whatever niche your product you think is a fit for, you can focus in on that vertical and get access to somewhere between like five and twenty big corporations that want to look at your stuff. And they hold one-day events where you can come in and do like a five-minute speed pitch, it's like speed dating, and like 10 startups will go. And then they've got other ones that are much more focused where they'll build a whole day for a company's innovation team, and they'll present lots of startup companies, and then they cherry-pick the ones they want to meet with and build a day's agenda out of it. And uh what I can tell you is that you've got these companies are self-selecting to want to work with startups, which is a giant barrier to overcome normally. It's a given in this scenario. And the second thing is they frequently want to do pilots, and they've got budgets set aside, they're looking to do it. And we've wound up doing like 30 or so pilots across different accelerators in the last two years. And the conversion rate from pilot to enterprise expansion and annual is around 50%. So it's another tool in the kit uh that I highly recommend. And there's a bunch of them out there, there's little regional ones, and then there's the plug and play is more of a big national play, you should take a look at for sure.

SPEAKER_02

Very cool, very cool. Well, that's that's fortunate when you've got uh uh uh that's a new uh as you said, that's a very new development. That's a very new development. And if if you've got the right kind of solution to work with these uh accelerators, more power to you, yeah, fantastic. They're typically not gonna help uh a lot of the enterprise offerings. The the Johnny come lately's in a space. You know, if you're if you've got a new PIM, if you've got a new search solution, if you've got a new personalization solution, you kind of you gotta go it on your own. Uh or if you're introducing something truly ground changing, that uh a completely new way of of constructing databases, that's you know, good. You're best to try to try it out on your own. And you know, there's a lot of common uh well, I uh there's a common line that I've heard many times. Hey, the founders need to close those first few deals themselves before they hire a salesperson. And um, you know, with enterprise software where you've got a very large transaction that's got the CFO involved, and you're selling to an enterprise that's uh a billion dollar plus, if you haven't got a background in sales, that could be pretty challenging. And and Brian, I think you've dealt with that. Yeah, I think I think you've been in that situation. Tell us a little bit about your your experiences there.

SPEAKER_01

You know, certainly going through, we look at uh starting out. I remember it's an interesting part. I'll go back to the Inner Shop story, where InnerShop, uh a storied brand, certainly in Germany, popped what public back in 1997. I think they had a $7 billion market cap at one part. And well, the the dot Stefan Schombach left the group. He ended up going through, start at Demand Ware. Obviously, he did very well on that one. But Inner Shop kind of candidly think lost its way. I think a lot of others would be fair to say that part as well. I I got asked to come in in uh 2016 initially to lead the Americas business, which before I came aboard, uh there, I don't think they closed a deal in 10 years. They really were living as more of a managed services outfit for uh a set of accounts that were candidly good, but at this part, you can only write a book so long at this park before you are going to hit the areas where it declines. So we we had to go in and really reboot and retool. And I came in as a VP of sales, and I was uh I was a sales team of one initially. Ended up going through and had uh great sales support and SDRs and others. And first thing I looked at was their way of selling was uh take an RFP because we did a peer based on their historical brand and swing, swing what we would swing the bat and see if we'd hit. Well, we had a good batting average of zero, unfortunately. Really good responses, and it was always that obsession of well, the product is great, it does great things. Why can't we go and close customers? Why can't we bring our customers? Daryl, you brought it out. It's like when you go into a CFO, the challenge I always went into was like, okay, you're a great. German company. How do you support us? How do you support the U.S. in this part? And we were publicly traded, all our dirty laundry was out, our size, and everything else was there at this park. So a lot of it really took how do we retool and kind of reboot a brand at this part in the America's market? So it took an approach where it went through and they initially uh I went in and we were actually even we didn't have a GM in the business. We split between Australia and the U.S. They were crazy enough to give me the car keys and said, okay, we're going to do the first inner shop history. We're going to appoint a sales guy to lead the organization. So I stepped in at this part and said, all right, let's go in. Who's the sales guy? Well, GM and chief sales guy. So part of it was we need to go and get our first customer win. How do we go in and demonstrate that we are relevant in the market and we can solve the market? And candidly, our biggest competition, we had SAP, we had Oracle, we had other really established players that were in that large enterprise space. Part of the thought was, do we want to go mid-market, down market? Well, candidly, it was an enterprise solution. And doing a couple pitches came very clear that large enterprise customers understood cost of implementation, the investment, change management that needed to be made. So it was definitely a fit. We just had to go in and find a vertical fit and get a really good story on that part. And Chris and Brad, you both pointed out well, so many times we take a pitch deck, nope, me and Andre Mihar go back in the car, fix it, go to another place. And it really came down to was it an approach where we take a whiteboarding approach and go through and really understand, okay, deconstruct a company's business problems and understand what was really good about it. Well, interesting enough, the product had been built around GSI Commerce, who had done some work to really make it not multi-tenant, but multi-tenant within a tenant at this part. So we can handle what we found out, okay, what about one holding company with massive sets of operating companies that want to go in and standardize? That's where we found an interesting fit. We can go in and work with a company and do a massive land and expand, find a visionary within a client. And we had to go in and find those risk takers, the ones that are saying, all right, we're going to go in and risk and reward. Who wants to go out and say, all right, I see fundamental changes, I see an amazing product. I'm going to put my salary, I'm going to put my job on the line and invest in this German company that hasn't had a big US presence to come in and solve problems and go forward and work with that. So we had to do a lot of market exploration, but we went in and landed a couple of pretty big deals that we ended in. And one was public, Danaher was actually one of our first clients that came in. And McGupta did a lot of talking about how we came in and selected, but had the vision at least to say, let's bring in one of our operating companies that allowed this to expand to, I think they had 20 some odd opcos that were part of it. So we went in, built a template, were able to expand, and then looked at other companies that were similar, other ones in the space, and really built the play around that. And that's how we were able to scale the company. But it was really a case where I look at it, you have to have a sales mind as a GM. That's why they tapped me, I think. And certainly I felt was a good part to go in. It was less about, yeah, we had to manage eBIT, we had to manage all the components that were out there, had to manage contracts, but a growth mindset and then an entrepreneurial mindset. I think that's the part where all of us have gone into is like, all right, it's okay to, I don't look at fail fast. I don't necessarily, I don't say fail. I really like quote by Thomas Edison as opposed to fail fast. Somebody asked him, I said, you know, you failed 10,000 times to try to build a light bulb. Why don't you keep at it? It's like, no, no, no, no. I didn't fail 10,000 times. I found out 10,000 things that don't work. And that was essentially the way I look at it is that, okay, we went in there and yeah, we'll try. We had a hypothesis. Here's a market. We tried the B2C commerce world with InterShop. It didn't work. It was too crowded. We didn't differentiate. We went in except for very few parts, the B2B commerce distributed manufacturers, like, wow, we have OMS, we have all these parts that are in there. We have the ability to do very complex catalogs in other parts. I hired somebody from one of our customers that was looking for a job, and it was an area we now went out in the field and were able to articulate what uh did of this part. And that's really where I think that mindset uh that you guys talked about, it really makes it to where, okay, we're okay to go in and test. We have to test. We had to build a licensing model that was brand new based on consumption. And then funny enough, others copied that because I had to align the ROI with our customers. Like, well, we're not getting a lot up front. I said, I understand. But look at the run what we got to go into, what we need to do to partner with our clients. So it was completely that throw everything out the window, try things new, break things, go out and take a lot of hits in the head that things didn't necessarily work, and then go back in and land that lighthouse account that grows internally, and then go find others afterwards.

SPEAKER_02

Well, uh so we've we've really discussed two German-based startups that had clients with names and installs in Europe and buyers in the United States, educated people, CEOs, CIOs, CFOs, gave no credibility whatsoever to that, didn't care. So you essentially had to build a brand in the United States, introduce your product, and then go through six months, a year of pitching before you finally got a client that was willing to sign on the bottom line. You know, that's uh that's a rugged story, it's a tough one because those are both established companies, and and even then with with referenceable clients in in uh in a westernized nation, it was it was like starting from scratch. So I guess from your perspective, and and we'll s we'll we'll we'll swing back to Brad here, if it what do you think a founder needs to know uh about their market and about what they're gonna need to do from a marketing perspective if they're gonna hire a sales executive for an enterprise software product for the first time.

SPEAKER_03

So uh say a couple things are important. One is your ICP, and the second one is hiring the right salesperson, because what you'll learn, and I I think uh probably all of us started as sales reps, and um, is that there's different kinds. Um, and um, like I worked at Oracle Salesforce for a long time, and I did fine, did well there. But a lot of people do well there, right? You know, it's it if you have a playbook, it it tell you how to sell, they have a process, everything's in place. It's just like plug and play, put a person in there. It's not that simple, but it it it it the process is there and how to sell it and the market to go after. If you start with a a new product where a lot of times the founders believe they know what the market is or their ICP is, but it's usually not what it what you end up finding out, it is, you gotta have a salesperson that can figure it out on its own, you know. And and and so I learned by myself by I was better at selling things that are hard to sell, you know, um, because there was a lot of other salespeople that couldn't do that, you know. So I started gravitating more towards new products, even within Oracle or Salesforce before I went off on it because I found that that a lot of people didn't want to do it, and I was better at it. Me personally, you know, it was a better my skill set, you know. So you gotta find a salesperson that has that skill set to be able to, and I think there's that entrepreneur side, there's that thinking just figuring it out of their own. Like you could put four new reps out there in a startup and one of them figures it out, the other three won't, you know. So it's it's um and it's hard to find that person, you know.

SPEAKER_02

Um That's that's about right.

SPEAKER_03

You know, but the the it's not because anything other than that person just figured it out how to sell it. Yeah, you know, they figured out how to sell it, and then you replicated everybody else, and after that it's easier, you know. But somebody's gotta figure out how to sell it, you know, and it's never the fo I think I don't say never the founder, but it's probably not gonna be the founder that figures out how to sell it. Um and it's probably gonna be a different ICP than they think, and it's probably gonna solve a different problem they thought it was gonna solve, you know. Um, so that that that's kind of that side. But the marketing piece is key. I mean, you gotta they gotta invest in marketing too. You can't go into a new market and just expect a salesperson to be able to do it. I mean, especially now. I think I read somewhere that 80% of the sales cycle is now done digitally, you know, before they even talk to a salesperson. So if you're not out there with a digital presence, I mean you're not gonna by the time you get in, it's too late because everybody else is already in there, you know, set the table for you, and you and you're not gonna have a chance. You know, so I don't think you can do it nowadays. Back when I did it at I mean, we we also hired a VPN marketing at the same time, and that was great. I mean, I th I wouldn't probably take a job as a startup if they didn't do that in whatever market you start in. A new any new market, if they don't put a marketing presence there or spend uh, you know, tell you how they're gonna what their plan is for that market, it's probably gonna not succeed, you know. Um and then I think you need your technical resource and you need an SCE of some kind to help to to kind of be in there with you, uh wherever that might be. Those those are the things that I think you really have to invest in. If they don't, they're not serious about the market anyways. They're just trying to see what they can get. Um so that that would be my thing. You find the right salesperson, and like nowadays you gotta invest in marketing. That's how it's you know, I I'm getting older, you know, and is so it things evolve, but you gotta stay up on it. And right now, all the digital marketing is the key. You know how they do with things like six cents and things that you can look at for see who's in market, all the they gotta invest in the tools, they gotta go out there and do the marketing, the digital marketing, all the all the things that you know drive the top of the funnel, you know, because it's not as easy to you can't just pick up a phone cold call anymore. People don't pick up the phone, you know. You you can still do it, you know, but it's not like it was before, you know. So that you really gotta you can't just go at it kind of like omni-channel and you know retail. You you gotta get they got to go for a multi-channel approach to it in order to be successful, you know. That's just the two things I would say, I guess. Yeah.

SPEAKER_02

Well, I you know, what you just described in terms of uh being uh the first entrepreneurial seller in an organization, that's who they're that's who they're hiring. Their first arch their first true entrepreneur, the person who's just all about the risk. And you're you're addicted to risk. You're like, you know, those guys that you see on extreme sports. That well, why the heck would a guy jump off a uh a cliff with a parachute when he knows if he doesn't pull it out in two seconds, he's gonna smash on the bottom. It's like because he's good at it. He likes it. So, you know, you're you're you're a good kind of freak, Brad. You're you're my kind of freak. I've spent, you know, 25 years trying to find those people. And it's hard to put my finger on it, but there's a certain, you know, there's a certain uh I I don't I don't know, cavalier nature, uh cavalier approach to risk. I dig it. I dig going where because nobody's been there before, because it's new. And a lot of entrepreneurs, when they're starting out, they know they're they're close to a space. It's like, you know, my my product is gonna attach to something from Oracle or SAP or Salesforce somewhere. So I can hire somebody from Oracle or SAP or Salesforce to sell my product because it's gonna be the same customers. Like, yeah, good luck with that. That person was essentially in a choir uh somewhere in the fifth in the 17th row, and they were uh being conducted, and they were their you know, voice was accompanied by another 150 voices. So yeah, they were technically there performing, but without the rest of the ensemble, they would have they would have been pretty off-key and fell flat on their face.

SPEAKER_03

I always told my wife when I start uh about the risk is like either I'm gonna figure out in 12 months or they're gonna fire me. So if you don't list going in, hey, it you know, it's uh it's it's intermittent. You know, it's like there's no I'm sending her some flowers. One of the two things will happen. Yeah.

SPEAKER_02

I'm gonna send her some flowers at the end of this because she's supported again if you have done some amazing things.

SPEAKER_03

Well, then we're gonna have shitty benefits because every startup has shitty but you have good medical plan or not. So you're gonna, you know, it's like uh you you may not even have one, you know. I mean, uh or you have to figure out one of your own. So all those things you gotta kind of prepare your family for, you know, before you do it. They gotta know what's coming when you get into it. Yeah.

SPEAKER_02

Yeah. Well, I mean, it for a startup founder, they're they're expecting not to have a life. They've kind of said, Yeah, I I I you know, I've got pictures of my kids on my desk, so I remember what they look like when I get home. Uh if I get home. Uh and the their first seller definitely knows that as well. It's like, I'm gonna kind of live on a plane. People are gonna forget what I look like. They're gonna forget my name. Who are you? Yeah, I live here. Yeah. Yeah. What's that ring? Okay. Uh but to your point, and uh, I'm gonna I'm gonna pivot back to Brian on this. Brad is, you know, you're you're pretty much of the mind, hey, unless the company is actually high gonna hire your marketing component partner at the same time, so budgeting the same amount for marketing as they are for sales from the get-go, they're gonna fail because the market is too sophisticated, because the digital selling portion of the equation is now 70% of the transaction process. So, unless you have a marketer who's gonna seed the ground, who's going to build the tools that your sellers are going to use to engage the client, to begin the to qualify those clients, to build the brand, to create the awareness, the seller is not going to have time. And one of the things I would also share is when you have somebody with the horsepower and sales of Brian or Brad or Chris, the least productive thing for them to be doing is to be serving as a business development representative where they're picking up the phone and calling people because that's not going to work 99% of the time. It's just a waste of talent and it's a waste of time. Uh so with that, Brian, tell me a little bit about what you think a company, you know, what your experience has been with uh companies that get it in terms of marketing and companies that don't that haven't sold the product yet.

SPEAKER_01

You know, your really good point, and very salient too. Our square we always run into is uh there's a careful balance. And I think Brad, you you've hit it well. There's marketing, there's sales, there's sales development. And I sat there and you look at it with a mature company, and so many times I've gotten in, people will do kind of an imentor company. Let's, okay, we want to, here's our sales projection, here's where we want to be. How many AEs? What can they reasonably close, and all these particular parts that are out there? People will go in, put it all together on a beautiful spreadsheet, and fail, burn a lot of cash just because the part of there's still that understanding of where it happens to be. There, there's a certain cost to market exploration. That's what I'll call it. You have market exploration, then you have kind of scale-up. So zero to one customers, one to three customers, then kind of five to ten. There's different steps. And 10 plus, you're now at a machine. You can run it, you can let you can meter it, you can do a lot of things. But that really one to five sort of range that you're getting into, the way I look at it is an ideal part. You absolutely need marketing. You need a lot of content, a reasonable amount of content to tell your story because people are gonna hit 70%. So you need to tell your story and your differentiated view and have an opinion. That's the good part about being a startup, is you gotta, I've always appreciated, even by autonomy days, it's probably what corrupted me. You gotta tell people why they're wrong or why everyone else just doesn't get it, and your company does, and those that buy in or don't. So you got to get that point of view out there. So there's a marketing component that does that. And then a sales part, when you look at it, yeah, us, my age, anyone else, anyone who's got this experience, us entrepreneur guys, we love to do, we love to pitch, we love to go in and take items out there. We're also not the cheapest people in the world. So it's really a great part is you want to go in, find young talent. You want to go and mentor and bring in. So you need an SDR, you need somebody that's gonna go in and grind to, okay, maybe it's working uh Apollo, maybe it's working some of the tools like this to go in and get meetings, going in and run the mechanics to ultimately go in and get you in front of a meeting. So I look at it as when I go on a plane, I don't want to go for one customer. I want five customers. I want to make certain that I'm on the plane, I'm taking advantage of my time. Because any times I can at least get five ad batch, I can tweak the message, I can go back, I can check it the next day, I can go in there. And that's really where I look at is uh in SDRs and efficiency multipliers. I remember one startup, uh the board coming to me saying, Hey, you know, we can get you a couple more AEs. I don't want more AEs. I say, what I need is I need more support. When I understand the business, then I can say, yeah, now I can scale. I understand what a sales cycle looks like, I understand what the buying group looks like, I understand our ICP, I can build it. But until I get really that exploration done, which may be six months, maybe a year at this part, it's an understanding to say, all right, here's my lean mean marketing machine, SDR, a digital marketing person, not a CMO, someone that can go in and run the channels. Let's get out there and test it. That's that's my that's kind of my rescue.

SPEAKER_02

You know, I know that you've been in this situation where you've got a company that that doesn't yet understand, okay, you've hired a sales executive, we need to make that investment at the same time in marketing to prepare the ground. And that with if you don't have someone that is essentially supporting you from an SDR perspective, it's it's really making it very difficult for you to iterate the iter iterate the pitch. You know, you have to be the person who builds that initial pitch, builds that initial presentation deck, builds that initial process, identifies what is our who are we gonna engage at our client? What are their, what are their what are we gonna have to do for each of these buying and the CFO, the CTO, the CIO, the VP of sales, the the chief marketing officer, everyone, we're gonna have to do a separate presentation for each of them because they have different agendas. What is what is your argument been to get more marketing?

SPEAKER_00

It's uh to me, it's kind of a cycle, and it's the three parties in it are the there's the salesperson on point, uh, there's the marketing, and then there's that SDR function, and they each have a different kind of a role, right? Um Yeah, the SDR, you want to leverage them to get as many at bats as possible, right? So you can do that iteration. And so if you're spending a lot of your time trying to get those meetings versus doing those meetings, you get less at bats. So it's uh it's a force multiplier. One of you guys put that perfectly, right? Um, but the SDR needs messaging to get those meetings, right? And they're gonna get that from the marketing guys. And then your job as the point salesperson or whoever your point salesperson is, is to bring feedback on the current messaging back to marketing and go, this part resonated, this part stopped. They really glommed onto this piece, let's try to expand it. Marketing's job is to then take that, mold the clay, feed the new weapons into the SDR, let them try to get new meetings so you get those at bats again. So it's uh it's a really cyclical thing. And the faster you can iterate, the more often you can iterate, the faster the messaging evolves, and the fat, you know, you win faster, right? So uh that's really been my experience. If you're missing any of those three, it's it's it's less efficient. If you're missing, you know, one of the two big ones, marketing or that sales point person, you're just gonna fail, right? The the evangelist, engineer, founder, they can espouse the vision, but they're not really salespeople, and so they can't do this motion that we just described very well. But the um the one last comment I wanted to make though, going back to an earlier comment about that first sales hire and um how unique that person is, the the number one trait that really kind of calls it out for me, and on top of the energy and charisma and everything else is the curiosity. You have to be really, really, really curious people to engage in just pure discovery conversations and not even know where they're gonna lead. And you're trying to suss out where are you where is your business pain? And it may not be anything I had on my deck, but we're gonna find some business pain. I can apply this thing that I have to your world, right? And curiosity, I think, is is really the trait.

SPEAKER_02

You know, that's that's been the defining characteristic that I've found, you know, is is finding the the seller that is they're they've got a a huge tolerance for risk, and they they live for that thrill. They're curious, they're they're they've they're uh telling me about all the different news cycles that they're they're following within the tech technology community, things that are you know on the other side of the planet from whatever offering they're spending their time on, they're aware of it, they're excited about it, so that when they go to work in their their niche or their space, they can they they can file fire on all cylinders. Well, you know, I I think uh unfortunately we've come to closing thoughts uh because this is this is cool. I could I could listen to initial sales process till the dogs come home. Till the cows come home, actually. The dog's already here somewhere. Anyway, he's he's been quiet for the last few minutes, thank goodness. Well, Brad, do you want to leave with leave us with anything? On see Advice for CEOs?

SPEAKER_03

Yeah, I was thinking, you know what I was thinking about is like um what makes them successful and what doesn't. When I think when I had a first my first successful one, I was I think I after it was done, I patted myself on the back saying, I built this thing. I I'm so I'm I'm probably the best I'm the best salesperson in the world, whatever. You know, um, but then you go do it again and you something similar and it doesn't work, and then maybe another one works, and so you try to start thinking, okay, maybe it wasn't just me that did it, maybe it was the the team, you know. And I think that's what you learn. So I think now what when I look at it, it's like it's the team that's so important. You got to get the right marketer because uh a bit a big company marketer is not the right one. You need a tactic, one is tactical, you know, and you gotta get the right S you gotta get the right S, you gotta get the right everything, right? You know, they all have to work together. And it's you can be the best salesperson in the world, but if you don't have those, you can't do it yourself, you know. Um so I think looking back, I had more appreciation for everybody around me. I think in the in the moment, you're you you start you're patting yourself on the back, right? Yeah, you know, but as you as you learn and you go do one that doesn't work, you know, and you start seeing, okay, I'm still the same person I was before, and the same salesperson, but what was different? And then you start seeing it's it's how you all work together. And and we we had a really good team. The ones we had a great team on did well. And it was it was probably less about the product, you know. I mean, but it was a team. So I guess that's uh my self-awareness, you know.

SPEAKER_02

There is an RIM team. Yeah, it it does, it is people tend to put all the weight on the sales professional, on the salesperson, because they're the one that actually gets to push the contract across the table and get the get the ink on it. But it is, it's a team effort in an enterprise sales, especially. It takes a team that can think together, that can share ideas, that can gain consensus, that enjoys the interplay of this idea was great. This idea stunk. How can we come up with a better idea? And that that interchange, and that's new for a company that's the the entire team up until that point had been completely obsessed with how do we make the product not break? How do we make the product better? How do we increase how do we improve our code? How do we make it more efficient? How do we put it in the cloud? How do we scale it? This is a whole new muscle that's being added to the body of the company to bring it to market. Uh Brian, any closing?

SPEAKER_03

And Brian, you mentioned Andre. I worked with Andre for overlapped. He he's great. Yeah.

SPEAKER_02

Any uh any closing thoughts for us, uh Brian?

SPEAKER_01

You know, it's it's funny, you know, Brad, you bring up Andre who were talking about uh a great guy to work with and a team. You know, it takes not a team, it's a city. I mean, you look at it with enterprise sales, all different aspects of it. You know, kind of my my thoughts too for founders that are really going in. There's a real interesting part with personality of a sales team or a commercial team. I go in there to say your first go-to-market team, there's uh one thing I learned was about the imperfect product. So you've got people trying to get a product out there, you've got sales, you need to have that back and forth where salespeople, certainly entrepreneurial salespeople, say, you know what, we've got a product that may have a couple of words here, but it's absolutely amazing at this part and it solves a problem. Be opinionated about it. That was Andre. Opinionated about it, passionate about it. And I look for that passion because if you're talking and pitching something new and you're out there, you've got to love it. You've got to be obsessed with wanting to solve that problem for a customer your way, and then be credible as to about where things are within the area, and but at the same time, just fall in love with it. You got to love the product, you got to love the problem. And that's really that part with a founder or a product person going into really hitting a salesperson. Andre was that product person, and that's kind of where we go into it. Love the product, brought the sales part and built things around it. So, all right, the two of us, when the amount of time we spent, we our wives that joke up more time on the road in front of customers seeing each other than we did in uh did probably at home in this part. So we're constantly on planes going back and forth. But you know what? That's what it took. We got there, and it was really that view of all right, a little bit of give and take. So, my kind of my parting thoughts for founders is really it's just finding that person who's gonna partner with you. You want on a founding team that you really see as all right, they're gonna love what I've built. They're gonna take what I've built, they're gonna understand it's not perfect, but they're gonna love it anyway and bring it out there. And that's really my fine success in this part.

SPEAKER_02

Warts and all, you gotta love it. Warts and all, you gotta love it. You gotta be passionate about it. Chris, what's what can you what can you share for some final pearls of wisdom for a founder that needs to hire their first sales executive and commercial team. Let's put it that way. We've established putting in place their first commercial team.

SPEAKER_00

Yeah, no, good, good, you actually hit the word I was thinking of, which is that they have to have that passion, right? That they've got this thing that they're convinced can add value to their customers or prospects, and they've got passion, and they go evangelize it basically. Uh, but in again, in the structured iteration way that we've been talking about, right? Um and then the second piece is the product piece, they need to be agile along with that cycle we talked about with the messaging, because you don't build it and then go message it. You message it, figure out what resonates, and then go, okay, I got five companies that I'll like this part. Now we got to build it, right? So, or at least build it a you know, a minimal, viable, fish showable feature to see if it scratches that itch or not. And that's actually that fourth step in that cycle that you're doing. It just doesn't iterate quite as frequently as the sales side, right? But it's it's really about you know really good communication between those departments, a good alignment, right, around what they need to get done and what's important. Um, and then the product evolves as rapidly as the sales messaging, and it gets really, really fun when you finally get you find that pattern and they go, I got it, I got it. Repeatable sales motion with the product I can solve this problem with, and then you can scale. And that's really what we're all looking for in the beginning part, right? So um it's just uh the last comment I've got really is it's a lot of fun. We talked about our scar tissue, but you've just got to have a certain mentality go in there and beat your head against the wall for this long, but it's it's super fun. I just enjoy the uh it's it's the race. It's a race of solving the problem and building a business versus running out of money and raising that next round, right? You're gonna enjoy the pressure and also enjoy the battle itself, or it'll it'll burn you out.

SPEAKER_02

Well, I find it to be a tremendous amount of fun being able to talk to you guys like you every day. You know, that's uh that's what I've been doing this for for a couple decades is people that are passionate about what they're doing, curious as all heck, and uh, you know, are uh a little adventurous, reckless, a little bit of a pirate, you know. That's uh that kind of captures in uh a nutshell what it is to be the first sales executive or member of a commercial team for a startup. And I'm glad I got to spend some time today with uh you you you pirates. Thank you so much.

SPEAKER_04

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