By business type
A subscription product is answering three different audiences at once
The unusual thing about a subscription website is that everybody arrives at the same page with a different job. Somebody is deciding whether to start, somebody is two weeks in and about to be charged, somebody has been paying for two years and cannot find a setting, and somebody in procurement is filling in a form about where your data lives. An assistant is genuinely good at three of those. The fourth needs your documentation to be better than it currently is.
What people actually type
Not the questions on your FAQ page. These are the phrasings that arrive in a chat window, lowercase and unpunctuated, and the material has to answer them in those words rather than in yours.
- what is the difference between the pro and business plan
- is there a free trial
- do you charge per seat or per workspace
- what happens when i go over my limit
- can i change plan halfway through a month
- where is our data stored
- do you have a security report we can review
- how do i cancel
- why was i charged twice this month
- can you invoice us instead of taking a card
- do you have a discount for non profits
- does the starter plan include the integrations
What to feed it
In rough order of how much work each one takes off the front desk. Every one of these is a document you almost certainly already have.
| Your pricing page plus the tier boundary rules behind it | Not the marketing grid, the rules underneath it. What counts as a seat, whether a deactivated member still bills, what happens at the limit (blocked, throttled, or billed for the overage), and how a mid cycle change is prorated. Tier boundaries are the most asked and worst documented thing in this business, and every one of these is a fixed rule rather than a fact about the person asking. |
|---|---|
| The product documentation, all of it | The material with the highest ratio of value to effort, because it already exists and almost nobody treats it as support content. A help centre nobody links to still answers the question. Index the whole thing rather than curating it, because the pages you would never have chosen are the ones people search for at eleven at night. |
| The trial terms in plain words | Whether a card is required to start, what happens on the last day, whether data survives if the trial lapses, and whether a trial can be extended and by whom. The question underneath is almost always am I about to be charged, and an unanswered version of that question produces a cancellation rather than a conversion. |
| Your security, subprocessor and data location pages | Where data is processed, which third parties touch it, how long backups are kept, what your audit report covers and how a prospect requests it. These arrive from a buyer who will never open the product, and treating them as an afterthought loses deals silently, because nobody tells you that was the reason. |
| The billing policy you would actually enforce | Refund windows, what happens on a failed card, how many times you retry, tax handling by region, and whether you accept a purchase order. Publish the version you enforce rather than the generous version, because the assistant will quote it back to somebody who then holds you to it. |
| Onboarding and migration material | How data comes across from whatever they use today, what an admin has to configure before inviting anybody, and what is realistically achievable in the first afternoon. This is the material that stops a signed up account from going quiet in week one. |
What has to reach a person
Anything that begins with my account
Why was I charged this amount, is my plan still active, has my invoice been issued, why did my card fail, how many seats am I using. These are the highest volume questions on a subscription site and the assistant cannot answer a single one of them, because it has no view of billing state and should never guess at one.
The right handling is to explain the general rule from the billing policy, say plainly that it cannot see this particular account, and take a name, an email and the message so a person can look it up. An assistant that explains proration in general and then admits it cannot see the invoice is more useful than one that stays silent, and far safer than one that improvises a figure.
Cancellation, by policy rather than by capability
Most subscription businesses want a person in the loop when somebody cancels, not to obstruct them but because the reason is worth hearing and the alternative is sometimes a downgrade nobody knew existed. That is a business decision, and it is worth being clear with yourself that it is one rather than pretending it is a technical limit.
So the assistant should answer honestly how cancellation works, what happens to data afterwards, and when billing stops, then offer the handover. What it must not do is imply that it has cancelled anything, because it writes into nothing.
A price that is not on the pricing page
Volume deals, annual commitments, custom terms and anything with a negotiated floor. The assistant can quote published list pricing and say that larger arrangements are discussed with the team, then collect the details. It should not invent a discount, because a figure produced in your name is the figure somebody opens the negotiation with.
A security questionnaire that needs completing
A buyer pasting in a control question is not asking for a chat, they are asking for a document with a signature on it. The assistant can point at what you publish, say what your review process is, and take the contact details. Filling in the spreadsheet is somebody's job, and it is a job that carries an attestation.
The wording when it cannot help
This is the message the assistant returns when nothing in the material covers the question. It is written by you rather than generated, which matters here more than anywhere: it is the sentence a stranger reads at the worst moment.
I cannot see your account, your invoices or your usage, so I cannot answer anything about this specific workspace. I can explain how plans, limits and billing work in general. If you leave your name, your email and what you need, I will pass it to the team and somebody will look it up.
It names what it cannot do, gives the route that can, and offers to take a message. A refusal that only apologises leaves the person exactly where they started.
Rules and duties that shape the answer
The person asking is often not the person using
Procurement, legal and security review arrive through the same widget as a confused trialist, and they ask completely different questions in a completely different register. A question about data residency or breach notification is a buying question from somebody who has been handed a checklist, not a support question from a user.
That has a practical consequence for what you index. If your trust material is a page nobody links to, the assistant cannot answer the questions attached to the largest contract values on your site.
Published pricing is a commitment, and stale pricing is a worse one
An assistant quoting an old limit or a retired plan is not a cosmetic problem: it sets an expectation you then have to decline in writing. This is the argument for pointing it at the pricing and documentation pages you actually maintain rather than uploading an export you will forget about after the next repricing.
The practical rule is that anything read from the live site ages with the site, and anything uploaded ages from the day you uploaded it.
Data protection requests arrive as ordinary chat messages
Somebody asking to have their account deleted, or to be sent everything you hold about them, is exercising a right that exists in most data protection regimes, usually with a response deadline attached. It arrives phrased as a support question rather than as a formal request, which is exactly why it gets missed.
Index the process, let the assistant explain it accurately, and make sure the handover lands somewhere a person reads daily. In most regimes the clock starts when the request is received, not when somebody notices it.
Never, whatever the documents say
Out of bounds
- Why a particular customer was charged a particular amount.
- Whether a specific account, invoice or subscription is active.
- A discount, a custom price or a contract term that is not published.
- Whether a security questionnaire answer would satisfy a given reviewer.
- Confirmation that a cancellation, refund or plan change has been carried out.
Playbooks for this trade
One page per recurring question, written for a SaaS company rather than in general. Each carries the phrasings, the material that answers them, a reply worth copying, and the line where it has to stop.
- Tier boundaries are the real question, not the headline priceSeats, overages and mid cycle changes are where SaaS pricing questions actually land. What an assistant can quote, and what it must never invent.
- Explaining how a charge was calculated without ever seeing the chargeProration, tax numbers and missing invoices arrive constantly. What the assistant explains from policy, and the point where it takes a name.
- A cancellation message is a retention conversation that has not happened yetThe assistant cancels nothing. It can be exact about notice, the last charge and what happens to data, then get a person into the conversation.
- A procurement reviewer working through a vendor assessment at speedMid deal a buyer's security team pastes control questions into chat. What can be cited, and why the spreadsheet stays somebody's job.
- The moment a subscription question turns into an account nobody can seeOn a subscription site the handover line is account visibility. What to collect in the message field, and why a second vague reply costs you.
- The card expired, and the notice went to somebody who has leftDunning, grace periods and the annual renewal that declines. What can be explained from policy when nobody in chat can see the payment.
- Reset my password is often the wrong question on a team accountIf sign in is federated there is no password to reset. What the assistant can explain, and why it can never send a link itself.
- Nobody still at the company can administer the accountOrphaned admin rights, expired invites and the wrong workspace. Access questions on a team product, and where the assistant has to stop.
- Three different people send this message and only one of them owns the dataDeactivating a member is not deleting them. Backups, subprocessors and who is asking decide the answer, and none of it happens in chat.
- The one question where the correct reply is somewhere elseAn assistant reads documents, not systems, so it cannot know the service is degraded. Point at the status page and say nothing about now.
- The account is open and nothing has been set up yetImport limits, what an admin configures first and what trial work does at conversion. Onboarding answers that stop a week one stall.
- The steps do not match what the customer is looking atSupport questions on a subscription product where the documentation lags the interface, and the fault may be the plan rather than a bug.
- Will it work with what we already haveWill it work with our sign in, our browsers and the tools we already pay for. Three questions, and one is answered by the pricing page.
- We did not mean to renew for another yearAuto renewal, a converted trial and a refund window that has closed. What the assistant may quote, and what only a person can decide.
- A conformance statement, and somebody who cannot finish the formA conformance statement is a document; a blocked user is a defect report. Neither is answered by claiming the product is accessible.
- The angry message is from an administrator with a renewal comingReliability, a capability moved to a higher tier and a bill in dispute. Where a paying team's complaint goes, and what is never conceded.
- Somebody wants into the beta, and the answer is not a dateAn invite queue for an unfinished capability is not a line. What may be said about early access, and why no date may be given.
- It is the middle of the night somewhere and the product is still runningThe software runs all night and the team does not. What to publish about coverage windows, time zones and plan based response times.
Questions
- Our pricing has edge cases. Will it get them wrong?
- It answers from what you index, so the edge cases it gets wrong are the ones your pricing page leaves out. That is uncomfortable and useful: the questions it fails on are a list of the things your buyers cannot work out either. Write the tier boundary rules down once, index them, and the failure disappears for the assistant and for everybody reading the page.
- Can it tell somebody how much they will be charged next month?
- No. It has no view of usage, seats or billing state, and it should say so rather than reason its way to a number. What it can do is explain how the charge is calculated, which is often what the person actually wanted, then hand over if they need the figure itself.
- Should we point it at our documentation or upload it?
- Point it at the site. Documentation changes constantly and a crawl that follows your sitemap picks the changes up, whereas an uploaded copy is accurate on the day you upload it and then slowly stops being true. Uploads are better for material that is not published at all, such as an internal billing policy you are willing to have quoted.
- Will it stop people contacting support, or just annoy them first?
- It depends entirely on how quickly it hands over. The pattern that works is a confident answer on documented things and a fast, honest handover on anything account specific. The pattern that fails is an assistant that keeps trying, because a customer who has typed the same question twice is now annoyed as well as unanswered.
Keep reading
- For a developer tools companyOn a docs site an assistant competes with search, not a phone line. Version skew, deprecations and error strings decide whether it earns its place.
- For a fintech appFees, limits and identity checks are safe ground. Balances, transactions and anything reading as a personal recommendation are not.
- For a healthtech appHealth data is a special category and clinical claims carry device rules. What a healthtech assistant answers for patients, and for buyers.
- Every business typeWhat an assistant has to know before it can answer for a trade.
Try it on your own material
Upload a document or point it at your site, paste one line of HTML, then ask it something only your business could answer.