Scale Like a CEO

Scaling B2B Tech Companies with Jonathan Buckley | Scale Like a CEO

• Justin Reinert • Season 1 • Episode 30

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Stop treating scale like a job title upgrade and start treating it like a system you can prove. Justin sits down with Jonathan Buckley—founder of Artesian Network and a seasoned fractional CMO/CEO—to unpack why early-stage B2B tech companies win when they favor efficacy over efficiency, generalists over siloed specialists, and fractional leadership over rushed, permanent hires. If you’ve ever felt the pressure to “hire the CMO now” after a Series A, this conversation offers a smarter path.

We walk through the traps that stall growth: mistaking friendly beta users for product-market fit, elevating big-company directors into startup VPs, and copying sales playbooks that depend on large BDR teams and no longer deliver ROI. Jonathan shares a practical way to confirm PMF with real evidence—tight ICP definition, channel and message experiments, quant you can trust, and clear conversion signals from first touch to expansion. He explains how fractional teams keep the work senior and hands-on: writing copy, building demand gen infrastructure, instrumenting the funnel, and coaching engineer-founders with metrics that matter. Instead of optimizing costs too early, we focus on building a minimal viable revenue engine you can repeat and predict.

You’ll also hear why finance benefits from the same model. A fractional CFO provides runway visibility, pricing and packaging analysis, and capital planning without bloating burn. Together, a fractional CMO and CFO create a cross-functional spine that speeds decisions and reduces risk. Once the playbook is real—ICP, channels, sales motion, content cadence—then it’s time to hire permanent operators to tune and scale.

If you’re a founder or investor searching for a clear, data-driven route to repeatable revenue, this one’s for you. Subscribe, share with a founder who needs to hear it, and leave a review with your PMF litmus test—we’ll feature the best ideas on a future show.

Jonathan:

What you need are generalists, really multidisciplined athletes that can run across all these disciplines at any given time with agility. The other is there in large companies, they're used to a well-orchestrated handoff and collaboration between teams. In smaller companies, you have to make that happen. You roll up your sleeves and you do the work. Even I, as the fractional CMO, I copyright a lot. I'm a big participant in building out the demand gen infrastructure and the processes. I don't hand this down to someone with lesser experience on my team. You need that in these early stage tech startups. So getting a director and up-leveling their title sets false expectations. And that's why the CMO in Silicon Valley has an average lifespan of 18 months. It's the shortest tenure of the C-suite. And the root cause we found over the years comes back to these facts. The disappointment is set up because they didn't move outside of the narrow cast expertise that they have in leading a team.

Speaker 01:

Welcome to Scale Like a CEO, the podcast where we explore the strategies, insights, and leadership principles that drive successful tech companies from startup to scale. Today we welcome Jonathan Buckley, founder of Artesian Network and seasoned fractional CMO and CEO, to dive into the world of scaling B2B tech companies. We'll explore the unique challenges founders face, the evolving landscape of leadership in tech, and the innovative approaches that are reshaping how startups grow and succeed.

Justin:

Give us a 90-second intro to you and your business.

Jonathan:

Excellent. Thank you very much for having me, Justin. I started my career as a career chief marketing officer for companies public and private in the tech sector in Silicon Valley. I was 32 years in San Francisco before making the jump for Europe for some time and now ended up back in the States. I formed 16 years ago a company called the Artesian Network. An Artesian water well is one, if you drill it in the exact right way, the water comes up under its own volition. And so it's a metaphor for revenue models. We developed a solid focus on early stage B2B tech companies, getting them to market after product market fit and scaling them. Over 50% of our clients have ultimately reached IPO or a successful M ⁇ A exit. Now I personally on the team step in as a fractional chief marketing officer for our clients, or in the most recent case with a company called Olympus.io, I stepped in as the fractional CEO of the company. But I have a full team behind me from creative to product marketing, pricing analytics, and optimization, infrastructure, build, content, all of that. So we come in as a fully integrated, trustful team to assist companies getting to scale.

Justin:

That's really great. You're focusing in kind of tech B2B, right? Absolutely, yes. And so curious, I'm going to combine a couple things here. If you think about what some of the challenges are in scaling tech B2B companies and the unique value prop that you offer, what is that and how you're solving those challenges?

Jonathan:

Sure. If you look at the composition of my team, many of us started as management consultants, really generalized business exposure across the different silos and businesses. We're also seasoned operators. Rather than passing work down in a typical consulting pyramid, if you will, to very young, new people to the workforce, we actually keep the work highly elevated. We feel that early stage tech companies have the need for speed and accuracy maintained. And there is an art and a science to getting these companies to prove themselves in the market and scale to a repeatable, predictable revenue model. And so having that experience is important. Those are the things that really differentiate us. Yes, we're a lot less costly than building your own team in-house, but there are many reasons why we don't recommend building a marketing team too early. That's in essence what carves out our ability. Each of us also is a marketing generalist. That is to say, we cover everything from the messaging positioning to demand gen, etc. Rather than have people on my team that are strict siloed disciplines like demand generation, like systems, we like each person to think like a management consultant in approaching the entrance in marketing and sales to the market.

Justin:

That's great. I'm curious, what do you see? Being as you have this perspective of seeing multiple organizations through scale to an exit, what are the biggest challenges that founders face as they scale?

Jonathan:

The biggest challenges, there's many of them, but let me try and boil it down to a handful here. Number one in the process is getting confirmed product market fit before putting any money towards scaling in the market or early stages of scaling. That is to say, we see many times across our clients that they feel like they ran a beta process, let's say, and they have a half dozen to a dozen testers of the product and feel like, well, we have a minimal viable product, it's it's confirmed product market fit. What we find though is when you separate out the early beta customers, which typically are not at arm's length from the CEO or other people in the company, their friends and family that adopt this. That too few of these companies have an empirically proven product market fit confirmation. So that's that's a challenge. When we come into a company, we look for that. The couple of failures that we've seen in our work over the last 16 years happened to have a root cause in a failed assumed product market fit before we came to the company. And we circled back, it took 18 to 24 months, but we had to eliminate every other variable until we got down to that one. Another challenge is quite typically in the tech space, the companies are founded and led by engineer-driven expertise. Obviously, they invent something, they're technical in nature. This is a different skill set than necessarily the leadership in marketing in sales. And so one challenge is coaching that early stage CEO along, especially if he or her are are in their first role as a CEO in areas of leadership in general, but then also guide them through the marketing maze. Remember, nine out of 10 times there's hostility between engineering and marketing. It's just the way it's always been. There are too many jokes to count in that area, but building credibility with that early stage founder and teach as we go so they can appreciate ultimately what we're doing, why we're doing it. And we make certain adjustments. We're a quant-driven group. So typically we relate on those levels with engineering-driven founders and CEOs. So those are two of the, I would say, top challenges. Maybe I'll put one more in, Justin. And that is we're seeing less and less of this, but with the advent of AI, but we find that some of the early-stage tech companies bring in very senior sales talent and they have a set playbook that has worked over the last couple of decades. For instance, building out big BDR or business development rep teams or SDR teams, sales development reps. And these are no longer provide the ROI that's really demanded for the efficiency of the modern day tech company. So there are other the change management part of this with the rest of the team, not just the CEO, but the VP of sales or the CRO is an important component. If you can overcome those things, the rest of it is math and execution.

Justin:

Yeah, that sounds familiar. I mean, I've a many that I talk to, it comes up that product market fit. Do we have that right? And then that leadership equation. So, number one, the founder, are they getting the development that they need to be an effective CEO? Because often they aren't. Maybe they're an engineer or maybe they're just a specialist in whatever area it is that they're founding around. Um, so being able to build that capability, but then also scale that in with as they grow, getting the right leaders in place to help them continue to grow. Um, and that the sales one is an interesting one because I definitely not just specific to sales, but I think there's also this challenge that oftentimes the what I see is companies that hire these very experienced people who maybe come from a much larger company and are used to having so many more resources, and now they get to the small company and really struggle with not having any many resources. I'm curious how you've seen that play out.

Jonathan:

Yes, Justin, that's so important to mention. Recently, I've actually written an article that was fairly well received on LinkedIn. It's also on artesiannetwork.com. And I also produced a podcast with a well-known finance guy, Glenn Solomon of Notable Capital, and a CRO friend of mine, Michael Hughes. We've worked together many times on this exact subject. So the paradigm we see in Silicon Valley over and over again, company gets funded, maybe they get their Series A, they're told they need marketing leadership. And what they do is recruit out of the larger tech companies, say a Cisco HP, and that train perfectly well-qualified people, absolutely. But coming out of a larger company like that and up-leveling the title, say taking a director and making them all of a sudden VP of marketing or CMO, has two problems with it. One is the large companies train their people in almost a siloed specialty track. So you are a demand gen expert at Cisco, you are a copywriter at Cisco, you are a content manager, you are a web person at Cisco. And what you need are generalists, really multidisciplined athletes that can run across all these disciplines at any given time with agility. The other is there in large companies, they're used to a well-orchestrated handoff and collaboration between teams. In smaller companies, you have to make that happen. You roll up your sleeves and you do the work. I even I, as the fractional CMO, I copyright a lot. I'm a big participant in building out the demand gen infrastructure and the processes. I don't hand this down to someone with lesser experience on my team. You need that in these early stage tech startups. So getting a director and up-leveling their title sets false expectations. And that's why the CMO in Silicon Valley has an average lifespan of 18 months. It's the shortest tenure of the C-suite. And the root cause we found over the years comes back to these facts. The disappointment is set up because they didn't move outside of the narrow cast expertise that they have in leading a team.

Justin:

Yeah, I've seen I've definitely seen that challenge in a lot of different roles. We assume, oh, hey, this person did really great at this big company. I'm gonna hire them, make them the senior-titled role, and they last maybe nine months. And if they last longer, there's a lot of dissatisfaction and tension in that relationship.

Jonathan:

Yes. I I wrote a recent article called Don't Hire the CMO Yet. And it was this very thing. We we actually, it sounds self-serving. We use an experienced fractional marketing team. We're there because there is a need for us to be there. But our our thesis is that forego putting a permanent team in place, other than maybe a generalized marketing manager, to start working with an outside experience team. And you can move faster. You don't have to spend two months recruiting and training and then turn around and have them hire, take two months to hire their team at all that expense and load. Bring in an agile team that has that experience and get to the repeatability and predictability in the model and then staff it with folks that are trained on driving efficiency versus efficacy. See, our our team is obsessed with efficacy, experimentation and finding the right things to do, not necessarily doing them right, first and foremost. I'm not saying we don't do things right, but what I'm saying is there's a focus on you can focus on efficiency and you can and optimization, or you can focus on efficacy. What are those things we should be doing unique to this company, its market, its selling proposition? Hopefully that makes sense, Justin.

Justin:

Yeah, and I wanna I want to clarify. So I think what I'm hearing is, you know, the reason we don't you wouldn't hire a CMO is because you actually need to focus on the processes and getting things right within that kind of marketing machine before you then hire the people that are full-time that are going to execute that. Is that is that a thought?

Jonathan:

Yes. Remember, we talked about generally you're pulling in more senior or or folks from the larger companies. In a larger company, the playbook is known, and the goal is day to day to drive better efficiencies in executing that playbook. In these early stage tech startups, you're doing a lot of entrepreneurial experimentation to find out what the playbook should be originated in the first place. So that's what I mean by focus on efficacy first and drive the optimization or efficiency later. So that's why we say get the company to, you know, there's debate whether it's this before or after the series B to bring in your permanent CMO and full-time team. We we had that debate on the previous podcast I told you about. But it's not the series A, it's not early in the process because they're going to tend to be your efficiency drivers and work on scaling at an efficient rate, your cost of customer acquisition. Well, in the early stage, we're working on how we should acquire customers. What are the right channels, the right messages, the right personas, the right tactics in supporting the strategy?

Justin:

Yeah. I like that that view on this fractional work because fractional and gig work is definitely on the rise. We see, I see so many more people hanging their shingle out as fractional workers. And I think companies have more of an appetite of that contractual expandable or elastic talent, if you will. I'm I'm curious, aside from marketing, are there any other functions in an organization that you recommend a startup leads fractional before they start building a permanent team around that function?

Jonathan:

Absolutely. Finance would be another area. Your CFO. Two things. And this goes for any fractional permanent C suite exec, like the CMO, the CFO A is very difficult to hire, attract and hire seasoned CFO talent when the company hasn't been de-risked yet. And by de-risking, I mean to attract these folks and have a sample of people to hire, you need that repeatable, predictable model there, or it's just seen as potentially career suicide. The other thing is, again, you want at this earliest stage the most senior talent you can get. So you can get this talent through a fractional basis. And the third thing is, frankly, like the CMO work and like the CFO work, early stage doesn't require full-time personnel. It's not a full-time job. We put in anywhere from 15% to 33% of a week into a company, even while we're hustling to get it going. And that should be enough. Again, there isn't administrative meetings and other things that come with a full-time, full-time staff. So we're able to move much faster. The CFO is one of those other examples I've seen successfully hired as fractional talent until they reach a later stage of financing. And then that can really come in handy. Yeah, yeah, that's great.

Justin:

I love that. Um, so what's the future look like for the artesian network?

Jonathan:

Well, since my return from Europe about two and a half years ago, I took I took a little time here where I landed and uh and then decided to restart the artesian network, reinvigorated. It was on hiatus when I was spent time in in London and Barcelona. And much of the team came back, and we've now added this past month, we've added two more people. We'll probably add two more people next month or the month after. And we've really worked on, we've refined our brand, our messaging positioning on artesiannetwork.com, and most most importantly, our demand gen engine we use ourselves. Primarily, we're using LinkedIn automation now. We're we're reaching out to very specific people. As you can imagine, those would be founders and CEOs at the right stage company, and to some extent to the VCs that fund them and staff their boards. And our message is a good one. Our discussion today, plus the fact that we've shown the results. You know, greater than 50, 50, 55% of our clients to date have gone public, have been successfully acquired, and roughly the other half have gone on to their series B, C, D, etc., and ultimately may reach that exit.

Justin:

That's great. Well, thank you, Jonathan, for joining me on the podcast. If folks want to get in touch with you, what is a good way to do that?

Jonathan:

Well, there's two ways: artesian network.com, there's form fill there. The other way is jonathanw.buckley.com. Again, jonathanwbuckley.com. And that is my professional but personal brand site. It has much of this content that we just spoke about and uh in the subject matter and just gives you background on me. Let me throw in a third LinkedIn, Jonathan W. Buckley on LinkedIn. I'd be happy to consult with anyone if they have ideas they want to bat around with their startup. Great. Well, thank you so much, Jonathan. Thank you. Thank you very much, Justin. I appreciate being here.