Guide
Four onboarding questions to ask every new SaaS subscriber
October 30, 2026 · Written by the New Odyssey team, with AI help.
Your billing platform knows that someone subscribed, to which plan, and when. It doesn't know what they hoped to do. That gap is where onboarding goes wrong: everyone gets the same welcome, whether they came to replace a spreadsheet or to impress their boss.
A few short questions, sent right after the first payment, close the gap.
1. What best describes your business?
Offer choices that match your market: agency, online store, professional services, software, other. This tells you who your customers really are, which is often not who your homepage assumes.
2. What brought you to the product?
List the three or four reasons people most often give, written for your product, with an "Other" box. This is the single most useful question: it says what they expect to happen.
3. What would success look like?
Offer a few outcomes in plain words, plus optional free text. People who can name a goal are easier to help reach it.
4. Are you replacing another tool?
Optional, but valuable: it tells you who you compete with in practice.
Only ask what you'll use
Every question should change something: the first email, a help article, a roadmap discussion. If an answer wouldn't change anything, don't ask it.
Use the answers
- Segment: group new customers by what they came to do.
- Personalize the first email: point each group to the part of the product that matters to them.
- Spot mismatches: if many people arrive expecting something you don't offer, fix the promise or the product.
- Compare with cancellations: reasons for joining and reasons for leaving, side by side, show where expectations broke.
Know what billing data can't tell you
Billing shows paying customers, so these questions reach people who have already subscribed. Free signups and what people do inside your product need a signup form or product analytics.
Where Joinfold will fit
Joinfold will email each new paying subscriber a short, optional questionnaire drafted from your website for you to edit, tie the answers to their subscription, and show the most common reasons for joining in a weekly brief. Joinfold isn't built yet; join the early-access list to be invited as places open.
Questions
How many onboarding questions are too many?
More than you'll use. Four short questions, each of which changes something you do, is plenty.
Can I ask people who signed up for free?
Yes, but not from billing data alone: billing shows paying customers. Free signups need a signup form or another source.