Probably not. .
Offering a free pilot might sound like a smart move. You’re a young SaaS company, hungry for logos, eager for feedback, and trying to get your product into real hands. Should SaaS pilots be free?
Surely making it free removes friction… right?
Well—yes. And also no. Mostly no.
A free pilot can actually backfire. Think: zero commitment, half-hearted engagement, and ghosting at the finish line. If you’re serious about converting leads into revenue, a free pilot might be killing your momentum.
1. A Free Pilot Is Just a Demo With Extra Steps
If they’re not paying, they’re not playing. Free pilots often fall into this awkward limbo where the client says “sure, we’ll test it,” but no one actually uses the thing.
Pro Tips:
- If it’s free, don’t expect prioritization. That champion you were banking on? She’s now buried under 47 other tools her boss actually paid for.
- “We’ll try it out and get back to you” = We will forget this exists by Thursday.
- Your internal team wastes cycles on a deal that isn’t even real yet.
In the wild: Jason Lemkin of SaaStr notes, “Free pilots generally don’t convert. You need to charge to get real buy-in.” (SaaStr)
2. Paid Pilots Create Skin in the Game
Want engagement? Put a price tag on it. When a company pays—even a token amount—they’re more likely to actually pilot your product, not just sign up and disappear into the SaaS abyss.
Pro Tips:
- Even a low fee signals, “This matters.”
- Paid pilots tend to convert 60–90% of the time. Adobe Sign reported a 90%+ conversion rate from paid pilots because it required minimal workflow disruption. In contrast, pilots that involve significant business process change tend to convert at lower rates due to internal friction. (SaaStr))
- You can always credit the pilot fee toward the annual deal—so it’s not even about the money. It’s about mindset.
Expert view: In “Create and Deliver a Killer Product Demo,” Oscar Santolalla stresses the value of structured, paid engagements: “The more serious the client, the more they’re willing to pay to validate.”
3. Free Screws Up Future Pricing Conversations
Imagine this: you do a killer job, the client’s happy, results are in. Time to close the annual deal. You show them your pricing, and they blink like, “Wait… we thought this was free?”
Pro Tips:
- Free sets expectations you’ll struggle to reset.
- When they expect to pay, they start measuring value. That’s a good thing.
- When they don’t, you get the dreaded: “We need to run this by procurement… in Q4… maybe.”
Pricing psychology: In “Pitch Anything,” Oren Klaff warns, “When value isn’t framed early, price becomes the enemy.”
4. OK, But Is There Ever a Case for Free?
Sure. Sometimes. Kind of.
You can offer a free pilot if:
- You’re collecting very specific feedback and you’ve handpicked the client to co-develop features.
- It’s a strategic partnership where the long-term upside clearly outweighs the short-term revenue.
- You’re time-boxing it to death (e.g., 14 days, one user, limited scope, no support hotline).
Data insight: According to Userpilot, free trials work best when paired with onboarding nudges and limited to 7–14 days. Any longer and engagement drops off fast. (Userpilot Free Trial Best Practices)
Let’s say you’re sold. Great. Now don’t go charging €50K out of the gate. Structure your pilot so it’s both accessible and sets you up for success.
Here’s your starter pack:
- 4–8 weeks max (of course, there are exceptions like high internal friction products)
- Clear scope and KPIs (“we’ll reduce churn by 15%” > “we’ll see how it goes”)
- Modest fee ($1K–10K depending on your market)
- Weekly check-ins to show momentum
- Fee gets credited if they convert
Playbook note: Headway.io recommends time-boxed pilots with pre-defined check-ins and outcome metrics to avoid scope creep and ensure measurable success. (Headway)
Not every SaaS pilot should look the same. The structure depends heavily on your product type, the level of touch required, and your customer’s internal processes. there are multiple trial formats worth exploring—ranging from opt-out freemium to concierge-led onboarding. Your pilot doesn’t have to follow a rigid format.
If you’re not sure what fits your GTM motion best, feel free to get in touch with me at angkan.mukherjee@gmail.com for quick feedback or ideas.
References
- Jason Lemkin, SaaStr – Should We Charge for the Pilots and How Much?
https://www.saastr.com/we-are-a-b2b-saas-startup-and-want-to-develop-our-product-in-pilots-with-customers-should-we-charge-for-the-pilots-and-how-much/ - SaaStr – What is the Typical Conversion from Paid Pilot to Annual Contract in B2B SaaS?
https://www.saastr.com/what-is-the-typical-conversion-from-paid-pilot-to-annual-contract-in-b2b-saas-2/ - Oscar Santolalla – Create and Deliver a Killer Product Demo (Book)
https://www.amazon.com/Create-Deliver-Killer-Product-Demo/dp/1783004912 - Oren Klaff – Pitch Anything: An Innovative Method for Presenting, Persuading, and Winning the Deal (Book)
https://www.amazon.com/Pitch-Anything-Innovative-Presenting-Persuading/dp/0071752854 - Userpilot – SaaS Free Trial Best Practices
https://userpilot.com/blog/saas-free-trial-best-practices/ - Headway – How to Run a Software Pilot Program: B2B Dos and Don’ts
https://www.headway.io/blog/how-to-run-a-software-pilot-program-b2b-dos-and-donts
