The VP of Free
Somebody must be the champion of the users who never pay — and it can only be product and the founders.
- Difficulty
- Moderate
- Time to result
- ~ongoing to results
- Steps
- 5
- Confidence
- 88%
Every company has a VP of Growth and a VP of Product; almost none has a VP of Free. That's a structural bug: the growth team is bonused on conversion, the sales team can't care about non-payers, and marketing only cares if free users monetise. Nobody is left to defend the long tail — the vast majority of users who love you and never convert, but who advocate, compound and make the business durable. Lemkin's prescription is that founders and product must consciously take that role, and use it to defend long trials, monthly billing and earned price increases against short-term revenue pressure.
Origin
Jason Lemkin, from a post he wrote years ago asking 'who's your VP of free?', reinforced by watching customer success get weaponised into a revenue function across the industry in 2023, and by Matt Mullenweg's observation to him that the biggest thing he underestimated at Automattic/WordPress was the power of compounding.
Core principles
- 01Nothing matters in B2B except that it compounds; customer-hostile tactics anti-compound.
- 02Products with a free edition are structurally better — they cannot hide bad onboarding behind humans who bridge buying and deployment.
- 03Run the longest trial that is still customer-centric. Slack, Canva and Zoom happily waited years to convert.
- 04Do not weaponise functions you don't need to weaponise — the customer-success revenue mandate destroyed relationships across the industry.
- 05Let customers pay the way they want to pay: individuals monthly, big companies with procurement annually.
- 06If you raised prices, you must have earned it with commensurate new value.
- 07For a self-serve/PLG business, churn is the number one metric. 3-4% monthly churn is close to unsolvable.
How to run it
- 1
Name the role and give it to product plus the founders
Explicitly ask: who is the VP of Free here? It cannot be growth (bonused on conversion), sales (cannot care about non-payers) or marketing. It has to be a founder-product collaboration.
Pro tip Frame it as being the voice of the customer — the job customer success used to do before it became a revenue function.
Watch out A head of growth given the free base will optimise it into a conversion funnel. That is their job; it just isn't this job.
- 2
Set the longest trial that is still customer-centric
Interrogate whose interest your trial length serves. The 14-day and 30-day norms trace back to Salesforce reps wanting to close in the same month — not to any evidence it was better for customers.
Pro tip Demand evidence: 'show me the money, show me the data that this is better for the customer.'
Watch out Be sceptical of any trial-shortening advice that arrives during a revenue crunch.
- 3
Refuse the reflexive move to annual contracts
Pushing SMB customers to annual looks great on a spreadsheet and is bad for customers who want to try something monthly on a card. Enterprise buyers with procurement departments want annual anyway — let each pay the way they want.
Pro tip Ask yourself: for a random product you just discovered, would you pay $240 up front, or $19 a month?
Watch out Lemkin calls this 'terrible advice from people who have never built products and aren't in the field'.
- 4
Earn every price increase
If you raised prices 8%, ask honestly whether you added 30% more value. In the pre-crunch era companies waited years and shipped a genuinely better product before repricing.
Pro tip Give the team one pass for the 2023 crunch — then get back to earning it.
Watch out Sending an email that says you're paying more, with no new edition and no new functionality, damages the relationship permanently.
- 5
Make churn the north star and ship three great things
For a self-serve model, drive churn relentlessly down — it is the metric that decides whether you compound to a billion. Then commit the product team to shipping three genuinely great things this year, not thirty good ones.
Pro tip Few things energise a whole company — including marketing and sales — more than shipping great product.
Watch out Lemkin passes on any low-end investment whose churn is not top-decile; 3-4% monthly churn is almost unsolvable.
In the wild
A leading public SaaS company, one Lemkin's team had used and loved for years, weaponised its customer success team with a revenue mandate. CS came to them mid-term: pay $50,000 up front or we turn it off this week — on a $299/month account. The demand was later walked back.
→ The relationship was destroyed, and the walk-back made it worse by revealing it as a threat. Lemkin's evidence that weaponising a customer-facing function anti-compounds.
Lemkin points at Lenny's own newsletter: ~600,000 readers, maybe 1-2% paying. A growth leader bonused on conversion will spend every calorie ramming the other 590,000 toward the paid edition.
→ Over-monetise them and the community — the whole basis of the business — ceases to exist. Somebody has to be the champion of the non-converting long tail, and that person is the founder.
Slack, Canva and (until recently) Zoom ran effectively infinite free access and were content to wait years for a user to convert.
→ All became epic companies — evidence that long/free access, when the product is good, compounds rather than leaks.
Common mistakes
Weaponising customer success (or product) into a revenue team
Across 2023, CS goals flipped from happy customers (NRR/GRR) to bringing in revenue from the existing base. It destroyed customer relationships industry-wide. Be careful before you do the same to product.
Copying trial and contract metrics without asking who they serve
The 14-day trial exists because Salesforce's SMB reps wanted to close deals in the same month. There was no evidence it helped usage or customers. Check the provenance of any 'best practice' metric.
Dark-pattern monetisation of the long tail
Checkout-page upsells that trick customers into buying things they didn't want (Lemkin's sister's job at Vistaprint) work — and they anti-compound, killing NPS and the relationship you need to reach a billion in revenue.
Is it for you?
Best for
Founders and product leaders at PLG/freemium companies deciding trial length, pricing and how hard to monetise a large free base
Not ideal for
Pure enterprise products with no viable free edition and a human-led buying-to-deployment bridge
From the transcript
“I wrote this post years ago saying who's your VP of free because who's got a VP of free”
“another related terrible piece of advice VC's give you is switch to annual contracts this is terrible advice”
“think about I would do the longest possible trial that is still customer Centric and understand there's tension”
“did you earn it what feature did you sh did if you raised prices 8% last year did you add 30% more value to your…”
“nothing matters in B2B that it compounds and some of this dark stuff you talk about on plg it anti-c compounds”
From the episode
Building a world-class sales org
Jason Lemkin (SaaStr)