Why SaaS Founders Hate Pilots (But Do Them Anyway)
How to Turn Customer "Tests" Into Real Revenue (Without Getting Bled Dry)
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Today we're talking about the unavoidable reality of SaaS sales: pilot programs. 😱
Picture this: You've just launched your digital product. You're hustling for customers, racking up proof points of product-market fit like trophies on a shelf, and suddenly...a Fortune 250 company reaches out. They love what you're building. They want to work with you. There's just one tiny catch—they want to start with a "pilot."
Your heart races. This isn't just another prospect—this deal would be the ultimate validation trophy—the enterprise logo that would prove you’re gonna make it after all!
Here's the reality check from a seasoned veteran: you're going to say yes to that pilot. And the one after that. And so on, and so on. And you should—but you must master the game of the paid pilot.
Notice how I said “PAID.” We’ll get to that part shortly.
Pilots are an unavoidable part of enterprise sales. Some founders start out saying "absolutely not" to pilot requests. (These are usually VC-backed founders, by the way—the only kind who can afford to turn down revenue.)
I get it—pilots sound like a wishy-washy pain in your ass. But here's what you need to understand: refusing pilots means refusing enterprise customers. And if you're willing to let a chance at an enterprise deal slip through your hands, you might as well get out of the game.
If you’re still reading this, the question isn't whether you'll do pilots, but whether you'll do them successfully and strategically, or let them drain your resources and derail your business.
I’m going to show you how to master pilots instead of letting them bleed you dry.
Storytime: The Legend of Carl the Bleeder
Early in our Boardroom Insiders journey, we got what seemed like a massive opportunity with a large enterprise. I was practically giddy when I met with my contact there—an SVP with budget juice who went bonkers for our product.
After our meeting he said he would "run it up the chain."
Record scratch. Freeze frame. That should have been a big red flag, but hey, he seemed to really, really like us!
Then the requests started trickling in like a leaky faucet. "Can you send me a few more profiles to show my team?" "We need some additional research for our presentation." "Could you hop on a call to explain your methodology to my boss's boss's boss?"
"Carl" called it a "pilot," but it was really just him running a masterclass in How to Get Free Sh*t 101. Free data, free records, free consulting, free meetings—if there was a way to extract value without opening his wallet, Carl found it.
I'm mortified to admit I let this pathetic dance continue for six months. SIX. MONTHS. Every time we thought we were finally close to a contract, Carl would pull out his greatest hit: "Just one more thing to help me make the case internally."
My partner and I dubbed him "Carl the Bleeder"—someone who strings you along in a bad relationship, with zero intention of ever putting a ring on it (or in this case, a signature on a contract). We finally cut him off like a toxic ex.
"Carl the Bleeder" became company shorthand for the rest of our journey. Whenever someone started asking for endless freebies under the guise of "evaluation," we'd exchange knowing looks: "Uh-oh, we might have another Carl on our hands!” 👹
The lesson? Some people will bleed you dry if you give them the chance. Don't let them.
Never. Do. Free. Pilots. 👹
If you take nothing else from this article, remember this: never do free pilots.
Jason Lemkin from SaaStr is clear: "If you don't charge, it's not a pilot. It's an extended demo." He argues that free pilots are "fraught with issues" and "never convert to paid."
Why? Because customers don't take seriously what they don't pay for. It's basic human psychology—when they have zero skin in the game, they treat your product like a free sample at Costco. They don't bother exploring features, asking meaningful questions, or diving into your customer success resources. Why should they invest effort when they haven't invested money?
So they half-ass their way through your free "pilot," come back with a big, fat "meh," and suddenly you're out the contract AND you’ve burned a critical lead.
Congratulations—you just played yourself.
Don’t believe me? Then run your free pilot. Go ahead. Then look at the usage data. Most of your users will show 1 or fewer log ins. I’d bet money on it!
The psychology is simple: investment creates commitment. Without financial skin in the game, you're just another vendor they're casually window-shopping—or worse, you're about to get bled by another 👹 who thinks your time is free.
So now that we've established the ground rules, the rest of this article assumes you're only offering paid pilots, OK?
Why Smart Customers Demand Pilots (And Why You Should Respect That)
Before we dive into the pilot playbook, let's put ourselves in your customer's shoes for a moment.
Picture this: You're a marketing director at a Fortune 500 company. Your CEO just dropped an aggressive growth target in your lap, and you need new tools to hit those numbers. You've found a promising startup with a product that could be a total game-changer—but they've been around for all of three years and have 30 employees.
Now imagine strutting into your next leadership meeting and announcing: "I'm dropping $200K of our budget on this startup I found. No, we haven't stress-tested it. Yes, they're completely unproven at our scale. But I've got a really good feeling about this one, guys!"
How do you think that conversation goes? Spoiler alert: not well.
When the implementation inevitably hits a snag, when the startup can't handle your enterprise volume, when their "support team" of two people goes radio silent during your crisis—guess whose head rolls? Hint: it's not the startup founder’s.
And this career-threatening phenomenon isn't just a Fortune 500 problem. At smaller companies, the stakes can be even higher. Resources are tighter, and every decision gets scrutinized by literally everyone at the company. A $50K vendor mistake at a 100-person company? That's a resume-updating event. Every significant vendor decision is a high-wire act because there are fewer safety nets.
This is why smart customers demand pilots. They’re not trying to scam free work or waste your time—they're protecting their careers from the very real risk of betting big on an unproven solution.
Understanding this mindset transforms how you approach pilot requests. Your customer isn't being difficult—they're being smart. And if you help them look smart to their bosses, you'll win every time.
The Hard Reality: This Sh*t Never Ends
Here's what most founders don't realize: pilots aren't just an early-stage, scrappy startup problem. You'll be fielding pilot requests when you're pulling in several million in ARR and feeling like a bona fide company.
At Boardroom Insiders, we were still getting pilot requests when we hit $4 million ARR. Why? Because to Fortune 500 companies, whether you're at $500K or $4 million in revenue, you're tiny. You're a rounding error on their quarterly reports. You're still "that little startup" they need to vet.
So expect to be treated like an unproven garage joint regardless of your ARR, your customer testimonials, or that shiny Inc. 5000 award on your wall.
This means pilot management isn't a phase you graduate from—it's a permanent strategic capability you need to master. The sooner you accept this reality and get really good at it, the better off you'll be.
Why Most Pilots Fail (And How to Fix That)
Turns out, I'm not the only founder who's developed pilot PTSD. The broader entrepreneurial community has reached a painful consensus on why pilots—even the paid ones—can be hazardous to your startup's health:
They can be resource black holes. As the folks at BuyerDeck bluntly put it, pilots fail because you can't afford to support them properly, or they succeed at completely destroying your focus. You end up pouring all your resources into this one shiny pilot while your actual paying customers and hot leads get ignored.
You have to sell twice. Jason Lemkin of SaaStr nails the other brutal reality: pilots force you to "sell the deal twice. Once for the pilot, and again to convert the pilot for a longer deal." Congratulations—you just doubled your sales cycle and halved your efficiency.
The Pilot Playbook: Your Step-by-Step Guide
So…when customers inevitably ask for pilots, here's your playbook:
1. Qualify the request hard. Ask why they need a pilot instead of your standard trial or contract. Often, they're really asking for custom development work disguised as a pilot. It’s up to you whether you want to do that kind of work. If you are still testing product-market fit and they fit your ideal customer profile…maybe? 🤷♀️ I’m not gonna lie—we did plenty of this early on.
2. Propose alternatives first. Offer extended trials, proof-of-concept sessions, or reference calls with existing customers. Many "pilot" requests can be satisfied with less resource-intensive options.
3. Price appropriately. The fee should be relatively low cost for the customer but substantial enough to ensure commitment. Spinnaker Sales Group says $5K to $20K per month is considered discretionary spending in most larger organizations—enough of a commitment without requiring board approval. Pilot pricing should also be aligned with your full pricing structure to avoid transition shock when converting to a full contract, which is the goal. Customers don’t like pricing surprises and they want to see logical math behind what you charge.
4. Set boundaries. No custom development, no integrations, no scope creep. Test your product as it exists, period. You want them to have the same great experience that you offer all of your customers—nothing more, nothing less.
5. Establish clear success criteria upfront with all stakeholders. What specific outcomes will trigger a full contract? Define this in writing before you start. Be specific. Steer clear of vague and inaccessible things like “feedback from the sales team” when you are not working with that team directly—because you’re probably not going to get that. (Ask me how I know! 😬)
6.Limited timeline. Six to eight weeks maximum, with defined and mandatory milestones and check-ins. Any longer than that, the customer will delay getting into your product, and you’ll lose momentum and the chance for a deal. (Again, ask me how I know! 😭)
7. Plan the path to conversion and deployment like your life depends on it. How exactly will they transition from pilot to full customer? Don't wing this—map out every step in advance, including timelines, teams, points-of-contact, and implementation phases. If you're dealing with a big enterprise, this isn't just important—it's make-or-break. When we finally landed our white whale deal with Salesforce, we spent months working with our contact to choreograph a careful, staged rollout across dozens of teams. Why? Because Salesforce had literally crushed small vendors under the weight of sudden enterprise demand before. They'd seen promising startups buckle when hit with massive demand overnight. We listened, we learned, and our rollout was a success. But only because we planned for it instead of just hoping.
8. Lock down executive-level champions who can actually write checks. Don't rely on some mysterious decision-maker hiding in an ivory tower that you've never met. You need to know exactly who this person is, be on a first-name basis with them, and have their direct phone number. Your champion should be genuinely curious about your solution, engaged in the pilot process, and enthusiastic about the possibilities. If your "executive sponsor" is a ghost who only appears in email signatures, you're setting yourself up for disappointment.
When to Walk Away (AKA Spotting Carl 👹)
Not every pilot request deserves a yes. Walk away when:
They won't pay for the pilot
They want extensive customization or integration work
They can't articulate clear success criteria
They don't have executive sponsorship
They want to pilot indefinitely without commitment timelines
They're clearly shopping multiple vendors with no intention to buy
They keep asking for "just one more thing" to help make their case
Remember: your time and resources are finite. Every hour spent on a low-probability pilot is an hour not spent on high-probability prospects or existing customers.
The “Pilot as Investment” Mindset
Here's the mindset shift that changed everything for me: pilots are great qualifying mechanisms.
A well-structured pilot tells you whether a prospect is serious about buying, has budget authority, and can implement your solution successfully. It's market research that pays—and most of the time it leads to a great-fit customer. It will also save you time and aggravation by eliminating the uncommitted and bad-fit customers.
When you frame pilots this way, you stop seeing them as revenue opportunities and start seeing them as investment decisions. Some investments pay off, others don't, but all will teach you something valuable.
Your Pilot Policy
As your business and your team grow, you need strict pilot policies so that everyone at your company is clear and on the same page. Here's what worked for us:
All pilots pre-approved by leadership
Standard pilot agreement template with no exceptions
Clear handoff process from sales to customer success
Mandatory onboarding session for customers
Post-pilot debrief required regardless of outcome
Immediate red flag process for "Carl the Bleeder" behavior
These boundaries protect your team's time and ensure pilots serve your business goals.
Be a Pilot Master!
Pilots are a reality of SaaS sales, especially if you are selling to large customers.
The companies that succeed with pilots treat them as strategic investments with clear boundaries, success criteria, and conversion paths. They charge appropriately, set firm timelines, and walk away when prospects won't commit to reasonable terms.
The companies that fail let pilots become consulting engagements that drain resources without generating the sustainable revenue, proof points or case studies that young companies so desperately need to make it through another year.
Which type of company will you be?
Remember: you're building a scalable business, not a custom development shop. Pilots should prove that, not disprove it.
And whatever you do, beware of 👹.
What questions do you have about the entrepreneurial journey? Email me at sharon@sharonkgillenwater.com and I might address them in a future issue or an office hours session (for paid subscribers only).
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