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The thing that comes after founder led sales is unlearning all the stuff that worked in founder led sales.
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Welcome back to another episode of Builders. As always, this show is brought to you by Frontlines IO, Silicon Valley's leading B2B podcast production studio. If you're bringing technology to market and want to learn from your peers, we have a library of more than 1200 interviews with Venture backed founders and marketers. Where they talk, all things go to market. Of course, if you want to launch your own podcast, we offer podcasts as a service to more than 80 tech startups. The idea there is very simple. You show up and host and we do everything else. Now with all that said, let's jump in today's episode. Our guest today is Wiley Jones, CEO and co founder of dos. Wiley, welcome to the show.
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A
Hey Brett, thanks for having me on one block away.
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B
Next time we got to do this in person.
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A
I know I didn't ask this in any of the pre combo. Is that a real bookshelf? Is that a real background?
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B
It's the real deal. My daughter hates it. As you can see, she's starting to like terrorize and move things around. So we'll see if the organization lasts. But I'm sure you're nine month old, you're starting to feel something similar of like orderly houses. They don't exist anymore.
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A
Yeah, no, you need more green books. I think you need some greens.
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B
We need more green. That's always the advice. I always tell people that if you're ever going to write a book, do a green one. It's like there's no green books. So do a great book.
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A
You would think there'd be more about money or something. I don't know. Anyway, you'd think so.
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B
Let's talk about what you're building, man. Talk to us about your technology and the problem you're solving.
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A
So DOS is an operations cloud. We're building a product that helps companies move, manage inventory, sell their product and get it into their customers hands. It's procurement, inventory management, order management, all that sitting on, let's just call it like modern data, warehousing, data platform and being able to connect up to third party systems, manage it all in one control plane. This has been a category that's been around for a long time and so we don't really have to reinvent the wheel in a lot of ways, but do it better.
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B
Is the category ERP or what's the exact category?
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So a lot of our customers understand it as ERP and a lot of Our customers understand it as inventory management. And inventory management is like one subset of the thing that we're kind of trying to create now, which is the idea of an operations cloud. You know, if you think about sales and marketing and many of these other people, they all got a cloud and operations teams didn't get a cloud is the idea. So we want to give them procurement, inventory management, order management, finance and accounting is something that we get plugged into. We used to sell it first party, we used to do it ourselves, we don't do that anymore. We could talk about the entire strategic component around that and how we made that decision, but we think of DOS as the donut and ERP as the entire system of the donut and the donut hole is the general ledger. We just want to sell the ring around, we don't want to sell the thing in the middle.
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B
How do you position that then with clients?
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A lot of it is marketed through the lens of the problems. And our customers in our ACP are looking for capabilities that they aren't getting from the point solutions they have today. They are covering using manual process and spreadsheets. They are looking for a either composite or unified solution. And the thing that they see in the market that's available to them is very large, long lead time enterprise software that is prohibitively expensive and not ideal. And so they're wanting a lot of those capabilities from that enterprise software, but in a more tractable and digestible shape. And the way we deliver that to them is say instead of giving you the full erp, we give you operations cloud plus your existing finance and accounting system and they go, okay, great, that makes sense. Because it's not just inventory management, it's not just procurement, it's not just order management. It's the combination of those things that they're really looking for.
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B
Do you envision that operations cloud is going to emerge and become a category that has competitors and has Gartner covering it?
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A
I don't know. I don't actually think it's the end terminal state for us. So I'm not super interested in its own self. The same way that if you think about Salesforce has sales cloud and they also have service cloud and they have a bajillion other ones. We think there's a similar world for us to be able to go into these adjacencies that are very obvious from these products based companies we work with. Field Services is a really simple example. We get a lot of requests for integrations into things that are in the realm of Field services and construction, that we just do not want a service today. Not because we don't have the capabilities to in the way that the product is architected, but because we don't want to dilute our focus and our concentration of our messaging.
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B
You touched a little bit on icp. Who's the icp and is that the exact ICP that you started with?
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A
Oh, it's definitely not the ICP we started with. ICP is, you know, it's one of those things it should be with a thing with an asterisk on. It is you should always tell people as of when and how long you think that will last. And so our ICP today is relatively recent in its formation, probably the last few months. It's actually that we filtered it down. We had a larger set that was crystallized and we made it a very selective decision to cut a few areas. So physical products based companies, but doing between 20 ish mil and about 200 mil though revenue is not the perfect proxy or heuristic. It's useful, but it's not sufficient. And they have to be like more complex than single channel dropshipping type businesses and less complex than like building rockets or doing pharmaceuticals. It's got to be in the middle of those things. And the degree to which it's in the middle is the main thing that we cut on. So we cut out a lot of the manufacturing customer base that we had been serving historically primarily because it wasn't rinse and repeat enough for the stage eradicate business.
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B
How painful was it to make those decisions and to make those cuts?
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A
It was not painful to make the decisions and make the cuts. It was painful to accumulate the information that showed us we needed to make those decisions and make those cuts. So what does it say? People say, I think the statement's kind of stupid, but it's pain is weakness leaving the body. It's like, no, no, no. Pain is information entering the body. Ow, I stubbed my toe. Your body telling you that there's something there that you shouldn't hit, right? It's like, ow. That customer was not good. It's like, yeah, you shouldn't sell to them, don't do that. And so making the decisions on the ICP was not the hard part. It was accumulating the knowledge to make those decisions that was the hard part.
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B
How long did that pain last of accumulating that knowledge?
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A
We did it for about a year. So we've been in market selling for let's call it about 20 to 22 months. Give or take. And we spent about 12 months out of that, let's say less, about nine months out of that, selling to companies that we probably shouldn't have sold to. And it kind of works its way through the system because you spend time marketing to them, they spend time in your deal cycle, you spend time in the post sales cycle. And then you spend enough time going through a few data points to then figure out it was a bad idea. And the degree to which it was a bad idea. I think the closer it is to your real icp, the harder it is to figure this out. Because it's like you can always be like, well, you know, it was close and you know, oh, our champion got fired halfway through the okay. And you kind of like you can find all these reasons and then the counterfactual is really hard to prove. But the thing that's really useful is just go look at the customers that have been slam dunk successes and be like, are they all the same? What is common about them? What is common about the ones that have been catastrophic failures? And then having the courage to be intellectually honest to then cull a large percentage of your pipeline.
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B
How do you deal with outliers there? I remember when I was first starting my company, I went through an exercise like that. I remember there was like one enterprise and then a bunch of like startups. And it was so hard for me to like mentally grasp that idea that like exclude the enterprise client and not to think about the enterprise client.
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A
I mean, everyone's going to make that mistake. I don't know anyone. You know, I had a really good conversation with someone about this who was a rippling for quite a while and I was asking them about how they went through this. And I think this is really common for people who sell to really horizontal markets or sell their product horizontally across quite a few markets is they were like, this is a rippling anecdote where they were like, we were selling into these healthcare groups and then we were selling into dentistry. And like the healthcare groups, horrible. The dentistry practices totally fine. And we're like, wait, what? Like, why is this different? And the nuances are more subtle than you expect and the impact of them is more profound than you expect. And so finding kind of that like in your ICP definition, it's a point in time. It's like a space in a point in time or a point in the kind of the passage of time. And it's multi dimensional. And figuring out which of those dimensions matters the most for your company is the most important exercise you can go through on a routine basis and taking inventory of that.
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B
Those were insights from Rippling or the guy at Rippling. What other insights have you heard that have been really impactful from a GTM perspective?
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A
Well, a lot of it is you take a lot of advice from people and you learn things from people who have built companies before. And I think it's really important to figure out what kind of company you want to be and to, like, really align that within yourself. You know, it's like, what game do you want to play when you're starting your company? And for me, I was like, oh, very clearly, early on, when we were building the business, I was like, I am very uninterested in building vertical SaaS. It's just deeply uninteresting to me. And there's nothing wrong with it. It just doesn't get me excited. I was like, okay, so then that forces you to make a couple of decisions about the how you build your product, how you sell your product, the vision that you articulate in the market and how you make that legible to the market. And then you go out to mentors and you find people who have built those variants of those companies, and you just show them what you're doing, and you're like, okay, what's wrong? What am I doing? That's stupid. And they'll tell you a bunch of different things. And then your job is like the ultimate job that the founder, and especially the CEO. Honestly, less important for the other founders to do this or, you know, is to figure out who you need to listen to. And sometimes the only person you end up listening to is yourself. But you have to figure out then whose advice you got to take. And usually you'll get three good pieces of advice, like, maybe at all. Someone said this to me also, so maybe that counts as one of the pieces of good advice. It's like you'll get three good pieces of advice, like, ever. You have to figure out what those are. That's basically, this show is brought to
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you by Frontlines Media, a podcast production studio that helps B2B founders launch, manage, and grow their own podcast. Now, if you're a founder, you may be thinking, I don't have time to host a podcast. I've got a company to build. Well, that's exactly what we built our service to do. You show up and host, and we handle literally everything else. To set up a call to discuss launching your own podcast, visit Frontlines IO Podcast. Now, back to today's episode. You should be clarified with him. Is that one of them or is this a startup?
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A
Yeah, yeah. I was like, didn't use one of my wishes. Like is that. Yeah, that's kind of meta. But no. And like, honestly, there was an unnamed person at a really awesome VC firm who was the CEO of a public company and I've been fortunate to spend a decent amount of time with him and their company went through a lot of hardship, was a massive market player, a big category winner and almost even a category creator. And then they ended up kind of going through some turbulent like, kind of like acquisition outcome. And he was the CEO there for like, you know, over a decade. And he basically told me like we were showing a bunch of stuff. He was like, hey, if you don't figure out how to play nicely with the ecosystem and coexist with the people who think that you are competitive right now, you will get your face ripped off. I'm just telling you this. He's like, I've seen this before. He's like, unless you can do something that no one else has ever done before, this is what's going to happen. And he was 100% right. And basically over the course of a month we completely changed the way we were architecting that strategy. We shut down first party finance and accounting and now we co sell it with a few major other providers. And it has been transformative for the business to do that.
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B
Where do you stand today in terms of building out the Go To Market team and the Go to market. Org?
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A
So we're in the leadership build and we're at the tail end of it and now we're in the ramp and it was funny. I love our sales leader. He's a very funny guy because he's very, very intellectually honest. And he was like, hey, you need to be nicer to your reps. And not that I'm a mean person or anything, but he was like, they have no process, they have no enablement, they have no tooling in systems. They have you as the only subject matter expert, solutions consultant, sales engineer. I was like, yeah, they don't need sales engineers. We hired great reps at ae. No, no, no. He's like, do you understand how hard this product is to sell? And I was like, no, I don't. He's like, yeah, that's the problem. And so I think a lot of the like the thing that comes after founder led sales is unlearning all the stuff that worked in founder led sales because your goal is to stop doing like you are not the thing that moves the chains on activity. Like you don't want to be the running back running the ball up the cut every single play because you have to be the coach of the team now. And like, okay, what do I do? How do I put the right pieces on the board and the right people in place and enable them to make the right decisions? And then I get brought in for top to top executive alignment when we can drive a deal to close. And like I'm still selling the vision and pushing the vision, but I'm not running deal set rep on Tuesdays and making sure the pipe is clean. Like it's unlearning all the stuff that you did to get to here. And it's really good to have a leader that can A, like that knows what that should look like and B is just way better at it than you are. And like unless you are a sales leader that is starting a company, like if you're a product person, you're an engineering person, like, oh my God, just make sure you run a great executive search for a sales leader.
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B
Like gotta get any painful lessons that you learned when you were running that process to find the sales leader.
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Talk to a lot of them. Oh, okay. Salespeople are great at selling. They're also very good at selling themselves. So be super careful. And I think it's the same for also talent executives. You know, it's like talent leaders, everyone says this is like you're going to have a hard time figuring out if this person's right for you and to the company. And a lot of people don't get their sales leader hire right. The initial ones, it's very uncommon to get it right on the first try. So just generally, you know, a lot of people will say so yeah, I think my view of that is like actually spending time finding the right person for the company. And like it just kind of goes back to the thing I said about knowing yourself. And it's like, what kind of sales leader does this company actually need? Do they need an evangelical person? Do they need someone who's going to come in and mechanically drive activity and force intellectual honesty and rigor in the company? Do we need someone who actually just like brings a bench, Someone who brings a Rolodex? Like what do you need as a company? And for us I was like, oh, we need someone who can think in systems and be really rigorous because we have so much other stuff and we have so much other firepower and like this is what we're missing. And we're missing industry and Domain expertise, you know, and like kind of fill out the blanks there. But I didn't realize that that was what was missing until I talked to a bunch of these variants and then I was just like, yeah, I can't imagine ABC person dropping in and like transforming our sales. Org. I can't imagine them transforming gtm, having that openness to the right person and not so much looking at the resume but like hiring the human being. That's kind of my mode now for hiring these, especially on the leadership side, which is like really the meta point to drive home, which is like when you get out of that founder led sales mode is like, oh my God, make sure you hire the right leader. If you don't hire the right leader, like you're not ready to leave founder led sales.
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Did you hire an exec search firm for this?
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Yes. Any regrets? Absolutely not. No.
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Do you think timing wise you waited too long to start to transition out of founder led sales? Did you get it just right?
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No. We definitely could have waited a little longer on the products piece of it. Like having pieces of the business ready to do that. But honestly also like, it's kind of one of those things where the right person meets you, where you are as a business. Yes. Like you could say, oh, I waited too long. It's like if you hire someone who is too early and they can't take the business where it needs to go and the stage in which you bring them in, then yeah, you waited too long. But if you hire someone at the right time and they catch you on that journey, then they're going to accelerate everything and they're actually going to change the thing that comes after them having joined. And so it's almost like it rewrites the truth of what's happening. And I've definitely been radicalized about the quality of leadership hires and it was not something because obviously I'd never hired an executive before. Like I'm, you know, this is the first time building company. The degree to which that matters is cannot be overstated. This show is brought to you by the global talent company, a marketing leader's best friend. In these times of budget cuts and efficient growth, we help marketing leaders find, hire, vet and manage amazing marketing talent for 50 to 70% less than their US and European counterparts. To book a free consultation, visit globaltalent.co.
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B
i believe you've said 22 months in market so far. What have you done or what did you do the past 22 months to grow? That was just a total waste of money?
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A
Well, we didn't waste a lot of money growing. I would say that's an easy answer. You selling to the wrong customers. Like, if you can save yourself the pain up front by knowing your icp, then you will save yourself a lot of money and you'll save yourself a lot of time. If you can't know your ICP upfront for many reasons, which is totally reasonable, then run minimum viable experimentation around that. Don't sign 10 customers that are, you know, hey, maybe we can do this. Like give yourself a budget. Don't go crazy and say I'm going to sign a handful of these like kind of weird things because I think there's something here. And like that openness is totally great. But like don't make it 50% of the deals you sign. If you are like, oh also we have a bread basket and this is what the breadbasket feels like. Like, you know, especially engineering folks and product people, they think in terms of like, oh, if we parallelize and like your eyes get so big they're like oh my God, that's what you said, the enterprise customer, right? They're like, oh my God, public company's coming, talk to us. Oh my God. Like you get super excited, right? And your job as a leader is to be optimistic and to be excited. Great sales leaders, great GTM folks, they are so paranoid, so skeptical, so distrusting of what's in pipeline, what is real, what's going to close and founders jobs is to not be like that at all. And so just try to apply a little bit of that in the experiments you're running. That's what wasted us a bunch of money. Like that's the thing we wasted money on is we spent time, energy and effort selling to customers. We should never have sold it.
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B
Now that you have locked in, you have the sales leader, marketing leader I believe you said is coming soon. Where are you going to put a lot of money? What are you betting on in 2026?
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A
I mean all engineering and product is like a massive piece of it. And pushing more demand into that organization, pushing more energy into the ways we outbound. Not on a one to many, but on the one to one working through key accounts and a lot of field marketing. I love field marketing. I think it's great and I think a lot of people are going towards it because you're competing against the hours in the day that someone has with marketing at this point. And when you have a captive audience and you have something compelling, being physically with them is so powerful for building relationships, especially in what we do where it's a lot of talking to people about their problems. I think it just depends on the business. You know, it's like for us, having a captive audience and being at a conference and asking someone about their business and they tell you everything about their business and you mirror back to them the things that we do for our customers and they're like, oh my God, that's the thing that we need. And they're like, yeah, I know. That's why I'm here. Spending a lot of energy on field marketing as a business is one of the easiest things that we've seen that's been really high leverage.
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B
I hope you're right because we're betting big on that idea too. Building out this podcast network of studios that in person matters a lot.
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A
So it does.
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B
Hopefully you're right.
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Yeah, I'm a huge proponent of it and I think it's only going to get more important is my sense of it.
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B
Yeah, I think that's my thesis and I think a lot of other founders, marketers, I know, they feel the same. I think in this AI world that we're living in, in person is just the logical place to bet.
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A
Yep, agreed.
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B
What does that look like for you in terms of the field marketing strategy? Can you unpack that for us a little bit? Is that big conferences, you know, small events, mix of everything, you know, like
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A
I had this conversation with someone on our team. This is going to sound crazy. I don't look at it as trying to manipulate like a person or a market or a perception of these things. It's that you want to surround them with what you are doing and you want to be in the air of their presence wherever they go, where they are thinking about these things. And so in our customers cases, it's going to their conferences where they transact with one another and they are thinking about the future. And so they're not thinking about the future when you cold call them. They're probably doing something important and they're probably not happy that you're calling them and they're probably not thinking about the future when they're scrolling through their inbox. But when they go to a conference and they're like, they're thinking about growing their sales channels and they're trying to think about how they can bring new products to market in the coming years and grow the footprint of their business and brand and et cetera. And we're there not selling to them, but showing them that there is a viable alternative in the world that we live in. And what we do, then the horizon and aperture of kind of what they think is possible begins to open and you build a real relationship. So field marking tactically to us is about building authentic experiences where our customers are instead of saying, hey, let's go to a software conference for erp, we are like, let's go to the food and beverage conference for XYZ and like, you know, we're going to a coffee trade show. It's like it'll probably be the only software vendor there. But also we can talk about how with one of our customers, they're doing a bunch of really cool stuff in our product and they're also a really cool coffee brand. And if you know Verve Coffee, you're a Bay Area, you know, they're a great brand, great company and they're doing a ton of really cool stuff and it's something that they think that needs to be a message to other people in their industry. And so like that's a cool opportunity for us is like, how do we go to the places where our customers are paying attention and opening their minds to new ideas?
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B
Okay, let's wrap here with one final question. We always like to ask about the big picture vision. So what does that look like? Take us out five years, 10 years, 20 years.
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A
So I would have put it on the 10 to 20 years a while ago, but now it's just like everything is going faster than anyone imagined. So if we are being really naive and extremely ambitious and we can kind of hold some space for that functionally. We have taken human intelligence and we have taken sand and put it into shapes and electrified it at a massive scale. And now we've taken human intelligence and made it machine reproducible for sense. And it's very cheap. So, okay, what are we going to go do with that? Well, every piece of excise and waste and time energy drain on how we do our day to day work, especially knowledge work. I don't think physical work will be as disrupted, but especially knowledge work can be automated in a way that is just as good, if not massively better than what we can do. And one of the things that we care a lot about is how do you help the physical real world move a lot faster by making it so that the information model of the real world can keep up. And a lot of that looks like the things that people do where they're manually verifying, checking items from document A and document B and spreadsheet A and spreadsheet B and coordinating commerce, managing inventory, procuring and buying things so that you can prevent items from stocking out or overstocking. We think that almost all of those workflows will be done by machines and not humans. And I would be almost a bit of a zealot and legitimately say that I think we have a moral obligation to do that because there's a much more meaningful way for us to spend our time as people. And so if we position that, then we think that that means that there's a lot of large enterprise software that's going to have to get ripped out over the next decade. And we want to be one of the people that's helping chip away at a lot of that. All right.
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B
Love the vision. That's where we're going to end things. We'll have to do this again in person next time before we wrap. For those listening in that want to follow along with you, where should we send them? Where should they go?
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A
Yeah, just look up doss.com,-o s s.com and connect on LinkedIn. I try to respond as fast as possible. And yeah, Wiley Jones on LinkedIn. And then if you're in San Francisco, hit us up.
- [24:05]
B
We're here.
- [24:05]
A
We always love having people by the office. Awesome.
- [24:10]
B
Well, that's all for today's episode of Builders, brought to you by the if you want more amazing content like this, visit Frontlines IO, where you'll find a library of more than 1500 interviews with founders, marketers and other GTM leaders, where we unpack the tactical lessons from their journey. And of course, as always, if you do want to launch your own podcast, we'd love to have a conversation with you. Visit Frontlines IO Podcast as a service. Mention that you listen, mention you love the show, and we'll give you a 10% discount. Thanks for listening. We'll catch you on the next episode.
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A
Sam.