How Oskar works

Oskar watches every paying customer so you don't have to keep them all in your head. Each day it reads what changed in your billing and product usage, decides which customers need you, explains why, and suggests what to do. You tell it when it's right or wrong, and it takes that into account next time.

1. Reading your data#

Oskar connects to two tools, both with read-only access:

• Stripe for billing: customers, plans, subscriptions, invoices and payments. See Connecting Stripe.
• PostHog for product usage: which events each person triggers, and when. See Connecting PostHog.

Stripe sends Oskar events as they happen, such as a failed payment or a new subscription, and Oskar also does a full read every night. PostHog usage is read every night. Oskar never writes anything back. Read-only by design covers exactly what it reads.

2. One picture of each customer#

Whatever tool it came from, everything about a customer ends up in the same place:

• Identities: how the customer is known in each tool, such as their Stripe customer and the people in PostHog who belong to them.
• A timeline: things that happened, such as a subscription starting or ending, or a payment failing or succeeding.
• Daily metrics: product events per day, how many people were active, and how often key features were used.

You confirm how billing customers match product usage during setup, before Oskar assesses anyone. Every usage signal depends on that match, so Oskar asks rather than guesses.

3. What Oskar knows about your business#

A failed payment means the same thing everywhere, but a quiet week does not. Oskar keeps a short profile of your business: what you sell, how often healthy customers use it, which actions show real value, the action that shows a new customer is set up, how you charge, and what matters most to you right now.

Oskar proposes much of this from your data. You confirm or correct it during setup and later in Settings. Facts are never edited in place, so each decision records what Oskar believed at the time.

4. Deciding who needs you#

Every night Oskar assesses each paying customer. You can also ask it to reassess straight away. For each customer it works out signals such as:

• whether a payment is failing
• whether usage is up or down compared with the two weeks before
• whether they have stopped using a key feature
• whether a new customer has reached their first-week milestone
• whether they have set their subscription to cancel, and what they wrote when they did
• what you have told Oskar about them recently

Those signals go to Jev, a decision model from TypeSafe AI. It decides what the customer needs (a payment problem, worth checking in, needs help getting started, possible expansion, or nothing), how urgently, and how confident it is. Low-confidence decisions are marked as needing a human check.

Claude, from Anthropic, then writes a short note explaining the decision and a suggested next step. The suggestion is for you to act on; Oskar never acts on it itself.

Every decision is saved as a record with everything Oskar knew at the time. See Decisions and feedback.

5. The focus list#

Oskar sorts customers by urgency, using your priorities to break ties, and puts the top few on your focus list. By default that's five customers a week, and you can change the number in Settings. Everyone else is grouped as quietly watching, recently resolved, looking normal, or not assessed yet.

You'll see the focus list on Today and Customers, in your email digest, in Talk to Oskar, and in any AI tool you connect. They all use the same list.

6. Learning from you#

On any decision, anyone in your account can choose:

• Useful: it was right.
• Wrong: say what the right call was and what Oskar missed.
• Already handled: you have dealt with it, and the customer leaves the focus list.

Your notes about a customer feed into that customer's next assessments for 60 days. You can also tell Oskar things in conversation, set up Watches for what you care about, and see on Impact the revenue that changed after Oskar flagged someone.