At Artesian, we’ve been quietly dedicating resources to something we believe will become a core strategic advantage for our clients.
We are developing custom GPTs designed to perform deep, empirical strategic work—not generic automation.
Enterprise PMF Advisor is the first of these.
It is engineered using: • Our experiential data from years of B2B technology launches • Internal frameworks we’ve proven repeatedly in-market • The most current industry benchmarks and best practices in B2B PMF, GTM, and scaling readiness
The goal is not to replace people.
The goal is to drive: precision, objectivity, and quality—at speed.
Trained as an economist, Jonathan W. Buckley began his career in the federal government before moving into telecom and later Arthur Andersen’s consulting practice, where he advised major technology players including Sun Microsystems. By the late 1990s, Buckley joined the founding team of NetBrowser Communications.
“I was the chief operating officer, responsible for everything from sales to accounting. But it was through the coaching of our chairman of the board that I was pushed toward marketing and business development,” Buckley says. It was an experience that shaped the rest of his career, leading him to serve as CMO for both public and private tech companies in Silicon Valley before founding The Artesian Network, a team of marketing professionals focused exclusively on scaling early stage B2B technology companies. With more than three decades of experience across consulting, operations, and marketing, Buckley has built a reputation as an advisor who sees business growth as a system rather than a set of disconnected tactics.
Jonathan recently sat down with techbullion.com and provided his insights on building credibility as a trusted advisor. Read the article here.
Early in my career, in the role of Business Development, I once walked into a boardroom convinced I had the perfect pitch. 30 slides. Financial models. Competitive benchmarks. Every detail nailed down.
I thought the math would speak for itself. It seemed compelling enough for me and the team backing me.
It didn’t.
Halfway through, the CFO was scrolling his laptop, the COO doodled in her margins, and the CEO looked politely detached. The deal never closed. It was over.
Months later, I tried again. This time I led with a story. A real company in their industry, with the same problem they faced, the same anxieties, and the same tough decision. I walked them through what happened when that company chose change. I created context, drama, tales of true outcomes.
The math didn’t disappear. It just came later—after the room leaned in and in support of the story, not the lead. That deal closed in 45 days.
Hundreds of millions of dollars in Sales, Corp Dev, Business Development and money-raising transactions later, I can summarize the tips to closing large deals in four basic steps. No, this is not comprehensive sales training. I have been schooled over the years in three major enterprise sales frameworks. Sandler, SPIN Selling, and Challenger Sale in addition to specialized Business Development training created by Arthur Andersen when I was a business consultant there. This outline in no way can replace the breadth and depth of these frameworks.
What I am attempting here is to take an abstraction of all of them and then shaping the macro concepts into a simple outline with the backdrop of having either leading large transaction deals or supporting them as the Marketing Executive/Team.
The Science of Why Story Wins
Stories are not fluff. They’re science. There is some real math to show why you absolutely need to start with a story, not “a pitch”, but a narrative. Why?
People remember facts “22 times more effectively” when told in story form (Stanford study).
A well-told story activates up to “seven regions of the brain”, compared to two for raw data (Princeton study).
“95% of purchase decisions are subconscious” and rooted in emotion (Harvard study).
For high-value deals, where risk looms large, story changes the math. Consider the Expected Value equation buyers run in their heads:
“EV = (Probability of Success × Benefit) – (Probability of Failure × Loss)”
Without story, they may peg success at 50%. With a compelling narrative—supported by a case study, testimonial, or analogy—they might raise it to 70%.
– No story: (0.5 × $500K) – (0.5 × $100K) = $200K EV – With story: (0.7 × $500K) – (0.3 × $100K) = $320K EV
That’s a “60% increase in perceived value”—from the same numbers, framed differently. This is why you need to be teamed up with a very strong storyteller in your marketing department who is skilled in the precision of messaging and positioning.
The Hidden Science of Enterprise Pre-Selling
By the time you’re in the room, the battle is half-won or half-lost. Enterprise deals don’t generally come down to one decision-maker. On average, there are 6–7 constituents involved in a large Enterprise sale: champions, skeptics, influencers, and decision-makers. Studies show this, my experienced validated this.
Marketing science tells us that each needs to be touched 5–6 times before they’re even open to a serious sales conversation.That means the real work begins before the pitch—with marketing that tells stories, primes trust and creates familiarity across the buying committee. Without this groundwork, the perfect story in the room may never get its chance.
This math of hitting 6-7 constituents 5-6 times should be the obsession of your marketing department or marketing partner. Each constituent will have different fears, uncertaintiesnbsp;andnbsp;doubts and they much be addressed uniquely in accordance with role in the company. Your marketing partner should be tailoring this messaging.
A simple example of such tailoring would be to examine the difference in content to say, a Vice President or C level exec versus, say, a director level professional. VP+ tend to be more concerned about issues of strategy, competitiveness and 18 month+ outlooks. Director level professionals tend to be more concerned with budgets and staffing impacts of large buying decisions. Staff and manager levels tend to be more concerns with more of a personal risk assessment. How does this impact them day-to-day. We do a lot of this work. It is effective.
The Four Phases of Closing Large Deals
Every big deal I’ve seen close follows the same rhythm.
First comes Preparation. You do the research—industry trends, financials, competitors. You map the stakeholders: who decides, who influences, who blocks. You build a narrative that connects your solution to their pain points, not in abstract, but in terms they live every day.
Then comes the Pitch. This isn’t about features; it’s about outcomes. You tell the story of how someone like them achieved results. You show the financial impact, yes—but you anchor it in a human journey they can see themselves in.
Next is Trust. You don’t win this with polish. You win it by being real—transparent about risks, clear about limitations, generous with references. You stop being a vendor and start being a partner.
Finally, Closing. Big deals don’t close on discounts; they close on clarity. You simplify decision paths, tie your solution to urgent priorities, and make the cost of inaction greater than the cost of investment. And you leave the room with shared ownership of what success looks like.
Bringing It All Together
Here’s the truth: spreadsheets don’t close seven-figure deals. Stories do. But stories alone aren’t enough. You need the right story, told to the right people, at the right time, within a disciplined process.
Marketing lays the groundwork.
Storytelling shapes the pitch.
Execution seals the deal.
Data convinces. Story converts.
And when the stakes are highest, story isn’t just a nice-to-have—it’s the difference between a lost opportunity and a transformative win.
💡 Takeaway: If you’re chasing large enterprise deals, stop polishing the deck and start crafting the narrative. Because when the story is right, the math finally makes sense.
When early-stage tech companies show me their go-to-market plan, I ask one simple question: “Can a rep with no industry experience close a deal in 60 days using this story and these tools?” Most founders pause. Then nod. Then—more often than not—they realize the answer is no. That pause is the real test. Because if your GTM motion only works when the founder is in the room, or when the AE is a 20-year industry veteran, it’s not a repeatable strategy. It’s a fragile workaround disguised as momentum. After decades leading GTM teams and helping nearly 40 companies go from early traction to exit, I’ve developed what I call the “60-Day Litmus Test” for evaluating go-to-market strategy. It cuts through hype, slides, and sentiment to reveal if your playbook is actually built to scale. Let’s break it down.
🚦The 60-Day Litmus Test
Ask yourself: Can a freshly hired sales rep, with no industry background, close a deal in 60 days using only the narrative, tools, and process you’ve built? If the answer is yes, congratulations—you’ve operationalized product-market fit into a functioning revenue engine. If the answer is no, don’t panic. But do diagnose.
🛠️ What This Test Reveals
This one question surfaces weaknesses fast. Here’s what it’s really testing: – Narrative clarity – Is the story simple, specific, and sticky? If a rep has to “learn it by shadowing the founder,” it’s not a story. It’s tribal knowledge. – ICP precision – Can a junior rep identify who to call without needing a three-week onboarding on industry jargon? – Enablement & tools – Is your sales motion codified in a way that enables consistency? Can they demo? Handle objections? Get a contract out quickly? – Product readiness – If a deal closes, can the delivery team implement and support it without heroics? Too many early-stage companies build their GTM strategy around unicorn reps and founder-led sales. That may get you from $0 to $1M, but it won’t get you to $10M and beyond.
💡 Best Practices from the Field
Here’s how I help clients build GTM systems that pass the 60-Day Test: 1. Codify your messaging into a single source of truth. One-pagers, demo narratives, objection-handling guides—every company needs them earlier than they think. 2. Instrument your pipeline to flag bottlenecks. If reps are getting stuck at the same stage, it’s not them—it’s your process. 3. Shrink the ICP, don’t expand it. Early-stage founders often try to go broad. The sharper the ICP, the faster new reps find traction. 4. Test with a “cold rep.” Hire a smart, coachable AE with no prior domain experience. If they can’t close quickly, fix the system—not the person. 5. Get out of the founder’s shadow. Build systems that work without you. Your GTM shouldn’t depend on your charisma, network, or ability to jump in late-stage deals.
🔁 GTM is Not a One-Time Strategy
It’s a system. A loop. A series of plays and messages that must be learned, adapted, and refined continuously. The companies that win aren’t the ones with the most slides. They’re the ones that reduce the sales process to something that can be learned, executed, and repeated. The 60-Day Test isn’t about lowering the bar. It’s about designing a GTM motion that doesn’t rely on miracles.
🧠 Closing Thought
Next time you review your go-to-market plan, skip the spreadsheets and ask this:Could someone brand new close a deal in 60 days using this?If the answer is no, fix it before you scale it.If the answer is yes—build the machine and press play.
A PR firm can be useful if: – You’re announcing a major funding round (Series A or higher). – You’re entering a highly competitive or consumer-facing market where media buzz directly drives business outcomes. – You have a compelling narrative and a founder/executive team able to deliver it well in interviews. – You’re already experiencing traction and need to amplify a moment, not manufacture one. Even then, PR works best when paired with existing momentum—not as a substitute for product-market fit or customer validation. We, at The Artesian Network have worked with many highly valued great PR firms in the past. We have gotten our clients as featured stories on Bloomberg TV, CNBC Top Disruptive Company Lists, and at the top of headlines on all the tech and business blogs and publications.
But PR Firms are best used at a later stage in the company lifecycle. With resources tight in the early years, you will receive a much greater ROI in other marketing tactics.
🚫 Common Pitfalls of Hiring a PR Firm Early
High cost, low control: Most PR firms charge $8K–$20K/month retainers. That’s a huge chunk of budget for startups with unclear ROI. – No guarantees: Media hits are never guaranteed. You’re paying for effort, not results. – Low relevance: Unless your startup already has a unique, newsworthy hook, reporters often pass on the story. – Misaligned incentives: PR firms optimize for coverage, not customer acquisition.
💡 Smarter Use of Early-Stage Marketing Budget
At the seed or pre-seed stage, founders should prioritize direct, measurable growth activities: – Content marketing (especially founder-led thought leadership on LinkedIn) Paid acquisition tests (Google, LinkedIn, Meta) – SEO for long-tail keywords – Email nurturing and marketing automation – Community building (forums, Discord, Slack) – Webinars or strategic partnerships These channels yield clearer attribution and faster feedback loops.
Strategy for PR Outreach for Early-Stage Startups
📣 Define the Newsworthy Angle
Product launch? – Customer milestone? – Funding announcement? – Major hire or partnership? – Social impact?
📋 Build a Media List
Use tools like: – Muck Rack (https://muckrack.com) – Hunter.io (https://hunter.io) – Manual research via LinkedIn, Twitter, and article bylines Segment by: – Tech journalists – Industry-specific reporters – Local business press – Podcasts/newsletters relevant to your space
✉️ Craft the Press Email (Pitch)
Example Subject Line:
“New AI Tool Helps SMBs Save Hours on Client Research — Interview Ready”
Example Email Body:
1 short sentence of relevance
1–2 sentence summary of your news
Why it matters now
Link to press kit or landing page
Offer exclusive quotes, data, or interviews
🗂️ Prepare a Lightweight Press Kit
Include: – Founder bio and headshot – One-pager about the company – High-res logo and product images – Key metrics or validation (users, customers, revenue milestones) Contact information Host it on a Notion page or Dropbox link.
📤 Pitch Strategically
Personalize each pitch (reference an article or beat they cover) – Use a CRM or spreadsheet to track opens and responses – Follow up once after 3–5 business days
📢 Amplify Any Wins
Share published stories on LinkedIn and Twitter – Add logos of featured publications to your homepage – Mention press in investor or prospect meetings – Repurpose quotes/testimonials in sales and fundraising decks
✍️ Final Recommendation
Unless you’re making a high-stakes, public announcement with broad appeal (e.g., $10M+ Series A, celebrity investor, or product going viral), skip the PR firm and invest in growth tactics with short-term ROI. When the time comes, you can revisit PR—possibly with a part-time contractor or a specialist aligned with your GTM goals.
AI is no longer a novelty in B2B tech marketing—it’s a competitive necessity. But while many marketers are exploring how generative AI can save time, fewer are using it to actually improve the quality of their positioning and messaging. At The Artesian Network, we’ve been launching and scaling AI-driven companies since 2017, well before ChatGPT introduced the broader market to what was possible. What we’ve found is that the power of AI in marketing isn’t about replacing expertise—it’s about multiplying it. When used well, AI helps experienced marketers move faster, test more ideas, and spot value gaps that human teams often miss. Here are ten best practices we use to get the most out of AI for B2B messaging and positioning:
1. Start with a Value-Claims Analysis Table
Before you write a single line of copy, use AI to map your product’s value claims against those of key competitors or substitutes. At The Artesian Network, we start this process by instructing the AI to summarize the marketing claims from competing product pages into a condensed list of recurring value statements—phrases like “faster onboarding,” “low-code customization,” or “seamless integrations.” To do this effectively, we: – Feed the AI the exact URLs of competitor websites—especially their product, solutions, and use case pages. – Instruct it to extract and normalize claims into consistent language. – Ask it to count how many times each claim appears on each competitor’s site to gauge emphasis and repetition. This process produces a value-claims matrix showing which claims are ubiquitous (table stakes), overused (hard to differentiate), and which are clear gaps your product can credibly own. But here’s the key: We always consolidate down to just 4–5 focused value claims for your product. These should be the claims your messaging consistently reinforces—across site copy, decks, demos, and outbound. Why? Because spread too thin, your positioning becomes noise. Concentrated, it becomes power. And it goes without saying: you must actually deliver on the claims you make. The most dangerous positioning mistake is to promise what the product doesn’t support—because that’s not positioning, that’s just brand erosion in disguise.
Value-Claims Analysis Output
2. Prime AI with a Fully-Formed Contextual Folder
Think of your AI as a junior strategist—it only performs well when it’s given a complete context pack: – ICP and buyer persona breakdowns – Buyer committee roles (typically 6–7 stakeholders in enterprise sales) – Competitive collateral and positioning – Industry-specific language and macro/microeconomic conditions – Pricing dynamics (commodity, premium, or disruptive) – Funding paths (which budget line the purchase comes from) Without this structure, outputs will always lack depth.
3. Clarify the Type of Sale
AI needs to know if you’re competing on price, features, ecosystem, or disruption. For instance: – A commodity sale competes on cost and utility. – A disruptive sale might draw funds from innovation or transformation budgets. That distinction radically changes how you frame benefits, urgency, and objections.
4. Define the Desired Messaging Tone and Voice Upfront
The best results come when you establish whether the voice should be authoritative, optimistic, provocative, or humble. AI excels at adaptation—but only when you’ve specified your brand’s persona clearly.
5. Use AI to Generate Hypotheses—Then Pressure-Test Them with Sales
Let AI rapidly propose alternative ways of expressing your value prop. Then run those through your sales team or revenue leaders. Often, the best ideas don’t come from a boardroom—they come from a rep’s inbox.
6. Train AI to Recognize Vertical-Specific Language and Pain Points
Generic messaging kills enterprise momentum. Load the AI with case studies, call transcripts, and customer quotes specific to your vertical. This primes it to speak the buyer’s language—without sounding robotic or detached.
7. Generate Variant Messaging for Each Buyer Committee Role
Your economic buyer, technical evaluator, and frontline user all care about different things. Use AI to tailor benefits for each: – CTOs care about scalability and integrations. – Operations leaders want faster workflows. – CFOs focus on ROI, not features. AI can handle that personalization at scale—if you feed it role-specific prompts.
8. Map Messaging to the Buying Journey
AI can accelerate the creation of nurture sequences, but only if you map messaging to awareness, consideration, and decision stages. Use AI to test which content themes move leads downstream fastest.
A Typical Enterprise Customer Journey Map
9. Avoid Over-Reliance on Prompt Templates—Invest in Prompt Craft
The best outcomes don’t come from prompt libraries—they come from experienced prompt engineers who understand marketing strategy. AI is only as strong as the marketer guiding it. You wouldn’t give a Ferrari to a student driver. Same rules apply here.
10. Continuously Refresh Competitive Inputs and Market Signals
Your AI models and prompt structures should evolve with your market. Refresh inputs monthly or quarterly: – New product launches – Pricing shifts – Analyst reports – Buyer objections from sales calls This ensures your messaging doesn’t go stale—and your positioning stays ahead.
Final Thought
AI doesn’t replace your positioning strategy. It reveals the gaps, accelerates the iterations, and makes it easier to go to market with confidence. But only if it’s used by people who know what they’re doing. At The Artesian Network, we build that process into every GTM engagement. Because the future of B2B marketing belongs to those who can see the signal in the noise—and move fast on it.
Why early-stage B2B tech startups need experienced, technical, senior marketing teams—and how to find the right one
Let’s be honest: most startup founders don’t trust marketers. And with good reason.
In the B2B tech world, we’ve seen a familiar pattern repeat itself—over and over. It usually starts with an incredible technical insight: a founder (or founding team) builds something genuinely novel. There’s a real gap in the market, and the early product makes a few smart people sit up and take notice.
But then comes the realization: you need to tell the story, not just build the system.
Why Founders Get Burned by Marketing
Many technical founders view marketing with a mix of suspicion and disappointment. They’ve either hired marketers who couldn’t grasp the product—or they’ve heard horror stories from friends who did.
This disconnect is almost inevitable. Too few marketers can “speak tech.” They mistake features for benefits, miss the architectural brilliance under the hood, or fail to translate a powerful capability into a message the market can actually understand.
It’s no surprise that many founders keep marketing at arm’s length. In fact, some are outright hostile to it.Let’s be honest: most startup founders don’t trust marketers. And with good reason.
In the B2B tech world, we’ve seen a familiar pattern repeat itself—over and over. It usually starts with an incredible technical insight: a founder (or founding team) builds something genuinely novel. There’s a real gap in the market, and the early product makes a few smart people sit up and take notice.
But then comes the realization: you need to tell the story, not just build the system.
That’s when the friction starts.
The burn cycle
They’ve seen the polished decks, the vague slogans, the cookie-cutter playbooks that ignore product nuance. They’ve seen form without function.
The Marketplace of Marketing Help is Siloed—and That’s a Trap Most of the marketing help available to startups is fragmented. You get:
Each offers a slice of the puzzle, but few are able to pull the full picture together. More often than not, they aren’t aligned with outcomes—they’re aligned with outputs. Blog posts. Pitch decks. Ad campaigns. Funnels. Metrics.
But early-stage startups need something much more foundational: go-to-market strategy rooted in reality, driven by insight, and delivered with speed.
The “Pyramid Problem” in Marketing Consulting Even when founders do engage outside help, there’s another common pitfall: the pyramid model.
You meet with a senior partner who seems credible—maybe even great. But once the deal is done, the work gets handed down to junior staffers. People who’ve never launched a company, never sat in a board meeting, never felt the existential pressure of a cash runway and a market that’s not quite biting.
These junior consultants often lack the pattern recognition that only comes from cycles of failure and success across dozens of startups. They may be smart. They may be eager. But they’re not ready to call the shots.
Startups don’t have the luxury to wait for someone to learn the ropes on the job.
When Founders Try to Hire In-House…
It Gets Risky Fast. So maybe you decide to build your own marketing team.
It sounds good on paper: hire a full-time VP of Marketing and let them build from there. But here’s what happens far too often:
You hire someone from a large company—a mid-level manager, maybe a director—and up-title them to VP or CMO. But their experience is shaped by a world that’s very different from yours.
In big companies, marketers are highly specialized—not generalists.
They’re focused on efficiency, not efficacy.
They’re trained to optimize existing systems, not create new ones from scratch.
Big Company Marketers Versus Those Optimized for Startups
Early-stage companies need the opposite. They need people who can navigate ambiguity, test hypotheses, iterate fast, and work across functions—not within a silo.
No wonder the average tenure of a startup CMO is under 18 months. The mismatch isn’t about intelligence—it’s about context.
The Time Trap: Why Startups Can’t Afford to Assemble a Team Slowly
Even if you’re determined to build the “perfect” team, you’ll face another brutal constraint: time.
Let’s break it down:
2–3 months to hire a VP
Another 1–2 months per discipline (content, demand gen, ops, design)
Weeks or months for onboarding and team chemistry
And that’s before you’ve produced anything of value.
The Timeline For A Full-time Marketing Team is Too Long
Speed is the only real advantage most startups have in the early years. You cannot squander it building infrastructure. You need traction. Fast.
Why Full-Time May Not Even Be Necessary
Here’s the kicker: most early-stage companies don’t need a full-time marketing team.
What they do need is a cross-functional senior team who can jump in immediately, drive strategy, deliver execution, and stay aligned to business outcomes—not just marketing metrics.
You need one part business consultant, one part execution partner. Not a loose federation of vendors. Not a junior team that needs mentoring.
You need a co-pilot.
What to Look for in a Fractional Marketing Partner If you’re ready to go the fractional route, don’t just look for an agency or an outsourced “stack.” Look for a team that:
Has deep operator experience—they’ve sat in your chair
Can “speak tech” and act as a translation layer between engineering and market
Brings product management insight, not just product marketing polish
Offers true cross-functional capability, from strategy to execution
Delivers one senior point of accountability—not a rotating cast
Follows a proven framework like Build It. Test It. Prove It.
And above all, make sure they know how to identify—and call out—a lack of product-market fit. It’s better to hear it early than fund a flawed GTM strategy.
The Artesian Network: Built for This Moment
At The Artesian Network, we’ve been that partner—for over 15 years.
We’ve supported dozens and dozens of early-stage tech companies across Silicon Valley, the broader U.S., Europe, and the Middle East. And the results speak for themselves:
The Artesian Network Has Serviced Clients Across The Globe
Over 50% have gone on to a successful IPO or acquisition
The others? Nearly all have raised successive rounds and achieved real traction.
In the rare cases where failure occurred, it was not without our early signal that product-market fit had not been achieved as outlined in two case studies we have outlined in previous LinkedIn Articles.
We don’t just “do marketing. “We help startups move faster, execute smarter, and build companies that scale.
Final Thought: This Isn’t Just Marketing. This Is Survival.
Marketing isn’t a department. It’s how the market comes to understand your value.
You can’t afford to get it wrong. You can’t afford to go slow. And you certainly can’t afford to bet your trajectory on junior talent and fragmented tactics.
If you’re ready to move faster—and smarter—bring in a team that understands the whole game. Marketing, product, growth, strategy—all in one.
Because the right fractional team isn’t a cost. It’s a multiplier.
