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Pricing and packaging, from a first business model to AI agents

The Pricing work group takes on pricing in group chats, from a first business model and SaaS tiers to AI features. Members also cover what gets people to pay at a paywall and how to move existing customers to a new price.

Updated October 13, 2026

Questions Answered

  • Retainers, project fees or upside: pricing consulting work

    Pick the fee by the shape of the work, and add a performance component only once the metric, the baseline and the client's part are written down.

  • Choosing a business model while a startup or community is young

    Find the behavior that creates value, put the charge where it does the least damage to it, and test with real buyers before you commit.

  • Setting a per-transaction fee: flat, percentage or volume tiers

    Charge for a completed transaction customers see as value, size the fee against the work the platform takes on, and judge it by what customers do after the first paid transaction.

  • Taking a pricing proposal to the executive team

    Put the decision on the first slide, show the evidence and the exposure account by account, and ask for a staged test with agreed stop rules rather than a full rollout.

  • Designing SaaS tiers around a value metric

    Choose the value metric before you draw tiers, start from Good-Better-Best, and plan for the packaging to change.

  • Tearing down a competitor's pricing, and the business behind it

    List what the competitor charges and how its plans step up, then work out why: the value metric, where the revenue sits and whether a high price pays for sales or is margin.

  • Pricing AI features and agents by the work they do

    Bill for a unit customers can understand and verify, check it against the cost of serving heavy users, and let people finish a real task before they pay.

  • Moving existing customers to new pricing, one cohort at a time

    Simulate each account's first bill under the new model, prove the model on new buyers, then move existing customers in cohorts with notice and a fallback.

  • Sizing a free trial to the time retained customers need

    Measure how long retained customers take to reach the paid value, treat 14 days as a starting test for simple self-serve products, and compare lengths on revenue and retention at the same cohort age.

  • Where a paywall should stop people, and what it should offer

    People pay when the wall stops them partway through a job they care about and offers to sell them the thing they're stuck on.

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Topics

  • Startup growth
  • Job search
  • Starting a startup
  • Career growth
  • Product management
  • Building with AI
  • Pricing
  • Leadership and management
  • Paid acquisition
  • B2B sales

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