Price Like a Product (and Unbundle Deliberately)
Align price to where value and cost actually accrue, and kill defaulted freemium and mis-packed SKUs
- Difficulty
- Moderate
- Time to result
- ~months to results
- Steps
- 3
- Confidence
- 85%
Treat pricing as a product decision, not a default. Understand where customers derive value and where you incur cost, and align the two. Reject packaging you adopted only because 'that's what you do' — default freemium, or an enterprise SKU stuffed with features startups actually want — and unbundle so buyers can self-serve what they need.
Origin
Jeanne DeWitt Grosser's pricing philosophy, drawn from Stripe (killing a defaulted Stripe Billing free trial) and a substantial Vercel pricing change in August (unbundling the enterprise SKU).
Core principles
- 01Pricing is a product; how you choose to price materially changes outcomes
- 02Understand where value accrues to the customer and where cost accrues to you, then align them
- 03Don't underprice out of fear of charging for the value you provide
- 04Don't default to freemium/free-trial without it being an actual strategy
- 05If startups are buying your enterprise SKU, it contains things that belong in self-serve
How to run it
- 1
Map value-to-customer against cost-to-you
Explicitly work out where customers drive value and where you incur costs, and design pricing so the two are aligned rather than inherited from a template.
Watch out Many companies grossly underprice because they're afraid to charge for the value they actually provide.
- 2
Challenge defaulted freemium/free trials
Interrogate whether a free tier is strategy or habit. Stripe launched Stripe Billing with a free trial 'because that's what you do,' then realized integrating billing already creates stickiness, so they killed the free trial with zero downside.
Pro tip If adopting the product already takes integration effort (a natural retention mechanism), a free trial may add nothing.
- 3
Unbundle mis-packed SKUs by watching who buys
Look at who's actually buying each SKU. At Vercel, about half the buyers of the enterprise SKU were startups — a signal that startup-relevant features were trapped in it. They pulled those out into self-serve.
Pro tip Let customers buy what they want without a human intermediating — it's more efficient for them and cheaper for you.
In the wild
Vercel found ~half of enterprise-SKU buyers were startups, indicating desirable features were mis-packed. They removed those features from enterprise and made them self-serve online.
→ Drove significant growth in the PLG funnel — efficient for startups to buy what they want, and cheaper for Vercel with no human intermediary.
Stripe Billing shipped with a free trial by default; on reflection, integrating billing already made customers likely to stay, so the trial was unnecessary.
→ They killed the free trial with zero downside.
Common mistakes
Adopting freemium or free trials as a default
Including a free tier because 'that's what you do' isn't a strategy; when adoption is already sticky (integration effort), the free trial gives away revenue for no incremental gain.
Leaving self-serve-worthy features locked in the enterprise SKU
If startups are buying your enterprise tier, valuable features are mis-packed — keeping them there forces a human sales touch and starves your PLG funnel of efficient growth.
Is it for you?
Best for
Founders and revenue leaders at consumption or usage-based businesses re-examining packaging as they add functionality
Not ideal for
Very early products with a single simple offering where elaborate packaging decisions are premature
From the transcript
“you got to think about pricing like a”
“product”
“we killed that”
“killed the free trial to”
“about half of the folks on the enterprise skew were startups, which suggests that there's stuff in the enterprise skew that a startup really wants”
From the episode
What world-class GTM looks like in 2026
Jeanne DeWitt Grosser (Vercel, Stripe, Google)