20 Questions to Ask in a Childcare Software Demo

Billing and payments (5 questions)

1. Walk me through what happens on billing day — from the moment attendance is finalized to when invoices are in families’ inboxes.

Why this matters: The billing workflow is where most centers spend the most administrative time and where errors are most costly. A demo that jumps to the invoice view without showing you the steps to get there is hiding the complexity. You want to see the full path: attendance confirmation, invoice generation, review, and delivery.

2. If a child is absent for three days but the family doesn’t notify us, how does billing handle that?

Why this matters: Absence policy enforcement varies significantly across systems. Some automatically charge for absence; some require manual override; some have configurable absence policies by enrollment type. Your center’s policy on absences needs to match how the software handles them — or you’ll be manually adjusting invoices every month.

3. How does the system handle billing when a child receives subsidy from the state and also pays a family co-pay?

Why this matters: Split billing (part subsidy, part family-pay) is where most childcare billing systems show their limitations. The billing module should know which portion of the weekly rate comes from which payer, generate the family invoice for only the co-pay portion, and track the subsidy claim separately. If the demo involves the salesperson saying “you’d handle that in two separate steps,” you’ve found a gap.

4. If a family disputes an invoice, what’s the workflow in the system — not what I’d do manually, what does the software do?

Why this matters: Dispute resolution is an edge case that happens regularly. Software should support it: viewing invoice history, seeing payment records, attaching notes to a specific charge, generating a corrected invoice. If the answer is “you’d handle that outside the system,” you know disputes require manual workarounds.

5. Is pricing per child, per family, or a flat monthly fee? Are there caps or tiers?

Why this matters: Pricing structure affects your total cost as your enrollment grows or shrinks. A per-child model that’s affordable at 40 children may become expensive at 60. A flat fee that seems high at 30 children becomes efficient at 60. Know the model and calculate your cost at current enrollment and at 20% above it.

Attendance and ratios (4 questions)

6. Show me the ratio dashboard — what am I looking at right now, in real time, if I’m a director looking at all my classrooms?

Why this matters: Ratio compliance is the highest-stakes operational task in childcare. The ratio view should show current headcount, current staff count, ratio status (compliant/warning/violation), and capacity status for every room simultaneously. If it shows yesterday’s data or requires you to navigate room-by-room, it’s not a real-time ratio tool.

7. If a room goes out of ratio right now, what happens — what does the system do and who gets notified?

Why this matters: Alert design is as important as detection. A ratio violation that the director finds out about by checking the dashboard 20 minutes later is less useful than an alert sent in real time to a designated person. Ask what the notification path looks like and how configurable it is.

8. How are staff counted toward ratios — do floaters and administrators count when they’re in a room?

Why this matters: Ratio counting rules vary by state — some states count floaters only when they’re actively supervising children; others have specific rules about which credentials qualify for ratio counting. The software’s ratio calculation needs to match your state’s rules, not a generic standard.

9. Can I see a historical ratio report — what our ratios looked like on a specific date and time last month?

Why this matters: Licensing inspectors may ask for ratio documentation for specific past dates and times. If your system can only show current ratios and not historical records, you have a documentation gap. A historical ratio report, retrievable by date and time, is the required evidence for a compliance inspection.

Subsidy billing (4 questions)

10. How does subsidy billing work with my state’s CCDF format? Can you show me a sample export file?

Why this matters: This is the most important question if you have subsidy-funded children. Don’t accept a description — ask to see the actual export file in your state’s format. Take the sample file and ask a colleague who submits to your state portal whether it would be accepted.

11. What happens if a state changes its required submission format — who updates the software and how fast?

Why this matters: States update their portal formats periodically. If your software doesn’t update to match, you lose the ability to submit claims electronically. Vendors with active state-format maintenance have a defined process; vendors without it often leave customers stranded when formats change.

12. After I submit a claim, where does it appear in the system and how do I track whether it was paid?

Why this matters: Claim submission is the beginning of the subsidy billing cycle, not the end. You need to track approved amounts, pending amounts, and discrepancies. A system that treats claim submission as the end-state gives you no visibility into outstanding reimbursements.

13. How does the system handle co-pay collection — can I track whether each subsidy family’s co-pay was actually paid?

Why this matters: Most subsidy programs require centers to collect family co-pays as a condition of participation. An audit may ask for co-pay collection records. If your system treats all subsidy billing as a single transaction rather than tracking co-pay separately, you have an audit documentation gap.

Data and security (3 questions)

14. What happens to my data if I cancel — specifically for historical records I might need for a licensing inspection two years from now?

Why this matters: You are required to retain childcare records for 2-5 years depending on program. If your software is your record system, you need access to historical records even after you cancel. Get the specific answer: how long post-cancellation, in what format, and is there a fee for extended access.

15. If there’s a data breach affecting my center’s records, how quickly do you notify me and what’s the process?

Why this matters: Your center has legal obligations when children’s personal data is breached. You need to know what the vendor’s breach notification timeline is, whether they’ll provide information about what was accessed, and what support they provide for your required notifications to families and regulators.

16. Are you SOC 2 Type II certified, and can you provide the certification documentation?

Why this matters: SOC 2 Type II certification indicates that the vendor’s security controls have been audited by an independent third party over a sustained period. It’s not a guarantee, but it’s the best baseline security indicator available. If the answer is no, ask what equivalent security audit they undergo.

Pricing and contract (4 questions)

17. What’s the exact annual vs. monthly pricing, including all fees — onboarding, per-user, support, and any feature add-ons?

Why this matters: Advertised prices are often the base price for a limited feature set. Subsidy billing, advanced reporting, and additional user seats are commonly add-ons. Get the full-feature price, not the landing-page price.

18. Is there a price lock for the contract term, or can pricing change during my subscription?

Why this matters: Month-to-month pricing can be adjusted with notice. Annual contracts should include a price lock — if your contract doesn’t explicitly say your rate is locked for the term, ask for it in writing before signing.

19. What is your auto-renewal policy — how much notice will I receive before my subscription renews?

Why this matters: Software subscriptions that auto-renew without adequate notice have surprised many center operators with an unexpected year’s charge. Ask for at least 45 days of advance written notice before auto-renewal. Confirm this is in the contract, not just a verbal commitment.

20. If I want to cancel, what’s the process and what are the data export options before my access ends?

Why this matters: Know your exit before you commit to an entry. A vendor who can’t clearly explain the cancellation process and data export options is telling you something about how they prioritize customer rights. You should be able to export all your data, in a usable format, with adequate time to do so after cancellation notice.