Topic · 18 pieces
SaaS to AI Business Models
Software priced per seat is priced against a labor cost that AI removes. The pricing model has to move to the outcome, and the margin structure moves with it.
This is the cluster that earns links, because it is the one where the arguments carry a company name and a number. Airtable at 2.7x ARR, Sierra's growth curve, what per-outcome pricing does to a gross margin that used to be ninety percent. The through-line is simple: seats priced human labor, and the labor is being removed. Everything downstream of that, procurement, quota design, the shape of a renewal, has to move.
Start here
- 01Salesforce Put Its CRM Inside ClaudeSalesforce beat on GAAP because it owns a piece of Anthropic, then shipped its CRM inside Claude. The app layer just volunteered to be the substrate.8 min read
- 02Cost Gets You In. Usage Keeps You.Glean's jump from $100M to $300M ARR got read as growth. The better read: why a buyer approves your product and why they keep using it have come apart.7 min read
- 03One Org That Got Landing RightSnowflake made landing its business model: it only gets paid when customers use the product. How consumption pricing solved what an org chart could not.7 min read
In the handbook
- Gross Margin Is Your Job NowCost per successful action is the new primary PM metric. If you don't own it, your CFO will kill your product before your customers do.
- Pricing for AI ProductsPer-seat is dead for AI. Price the work the seat is no longer doing: outcomes, usage, value units.
- Pricing Migration: The 18-Month Quarterly PlaybookSix quarters, four mandatory CFO/CRO/Board/Lead-customer conversations, the gross-margin recovery curve, and the contract terms that defend outcome billing.
- The Investor and Board Narrative for AI-Era SaaSGross margin compression, NRR redefinition, the new rule of 40, the right comp set, and the four CFO sub-agreements that make the trough boring.
Everything on this topic
18 pieces- 01Salesforce Put Its CRM Inside ClaudeSalesforce beat on GAAP because it owns a piece of Anthropic, then shipped its CRM inside Claude. The app layer just volunteered to be the substrate.8 min readAug 26
- 02Cost Gets You In. Usage Keeps You.Glean's jump from $100M to $300M ARR got read as growth. The better read: why a buyer approves your product and why they keep using it have come apart.7 min readAug 26
- 03One Org That Got Landing RightSnowflake made landing its business model: it only gets paid when customers use the product. How consumption pricing solved what an org chart could not.7 min readAug 26
- 04The Repricing, Beyond AirtableAirtable at 2.7x ARR is not an anecdote. Chegg, Stack Overflow, Squarespace, and Smartsheet are the same repricing, in two kinds. Which one is yours?9 min readAug 26
- 05Airtable Sold for 2.7x ARR. That Number Is the Whole Lesson.Airtable did not fail. It has ~$480M ARR growing over 20%. What collapsed was the story investors were paying for, and the AI pivot could not save it.16 min readAug 26
- 06Financial Fluency for PMs: Own the Margin Before It Owns YouFinancial fluency is now a PM job requirement. The five numbers to know cold, the finance working session agenda, and a 4-week plan to own your margin.9 min readJul 26
- 07Software Categories AI Is Killing: A PM's Field GuideThree forces are collapsing entire software categories. Which are dead, which are reshaping, which have moats, and what to do this quarter if you build in one.21 min readMay 26
- 08Distribution Beats Product, and AI Made It HarsherAdobe taught me distribution beats product. I unlearned it at startups for a decade. AI made product cheap to build and distribution the only moat.8 min readMay 26
- 09Per-Outcome Pricing: What Gets Clearer and What Gets TerrifyingThree SaaS-to-per-outcome pricing redesigns: support automation, sales enablement, contract review. Margin math, dispute mechanics, and contract terms.13 min readMay 26
- 10From SaaS to Service-as-Software: The CPO's Field GuideThe CPO field guide to Service-as-Software: outcome-based pricing, what changes inside the product, the new org chart, and when to make the shift.15 min readMay 26
- 11The CFO Conversation: Defending a 20-Point Margin DropThe single most important conversation of the entire pricing migration. The script, the part that almost didn't land, and the seven leading indicators.4 min readMay 26
- 12The Jevons Cliff in Outcome PricingInference costs drop 50% per year. Your $0.50/resolution price is a moving target. Hold or pass? The framework nobody has published until now.4 min readMay 26
- 13Margin Watch AgentTracks gross margin per outcome daily, classifies compression cause, and forecasts the Jevons cliff. Pricing reviews stop being post-mortems.7 min readMay 26
- 14The Pricing Migration Sequence: An 18-Month Quarterly PlaybookPer-seat is dying, but it pays your payroll. The quarter-by-quarter playbook for moving $20M ARR to hybrid outcome pricing without crashing NRR.20 min readMay 26
- 15The Cannibalization Playbook: How CPOs Win the AI TransitionThe honest CPO move when AI replaces your SaaS: set a sunset, kill the comp asymmetry, pre-sell the gross-margin trough. The seven-decision sequence.16 min readMay 26
- 16The AARRR Dashboard You Actually NeedForget vanity metrics dashboards. Here's how to build a pirate metrics dashboard that tells you where your product is leaking value - and what to fix first.14 min readMar 26
- 17The Shift from SaaS to Service-as-SoftwareSoftware is evolving from a tool humans use into a workforce that does the work. Here's how the SaaS to Service-as-Software shift changes everything for PMs.4 min readNov 24
- 18SaaS Is Becoming Service-as-SoftwareSoftware used to help people do work. Now it does the work itself. This shift changes how you build, price, and think about product. I'm living it at Smartcat.6 min readNov 24
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