If you're comparing timesheets and expense reporting software, you'll probably end up asking the same five questions most finance teams ask. In recent discovery calls and demos with controllers, CFOs, and AP leads at construction firms, nonprofits, professional services firms and government contractors, they had a few commonalities even though they were in different industries.
Here they are, in close to the buyers' own words, with what a good answer should cover. The right answer for your team depends on your ERP, your cards, and how you code costs, so treat each one as a question to bring to your demos.
The short version: Finance teams want to know whether the software (1) syncs with their ERP so nothing is entered twice, (2) works with the cards they already have, (3) gets costs coded to the right job, grant or cost center at entry, (4) stops incomplete reports before they reach accounting, and (5) what it really costs and how long setup takes.
1. Will it sync with our ERP so we stop entering everything twice?
Many conversations start here. In one real example, a construction controller adds every new job and cost code in Sage Intacct, then again in her expense tool. A nonprofit team running NetSuite for grants and ADP for payroll wanted to know how data would move among all three systems so staff only enter it once. Another buyer asked the shortest version: if I set up a project in the ERP, does it show up on its own?
A good answer starts with the ERP staying the system of record. Projects, dimensions and GL codes should flow in from it, and approved timesheets and expense reports should flow back. Beyond that, press on specifics:
- Which data moves in which direction, and how often
- How to push an urgent change through between scheduled syncs
- How long the integration with your ERP has been in production, and who you can call for a reference
What decides the answer: which ERP you run (Sage Intacct, NetSuite and Microsoft Dynamics 365 each work differently), whether HR or payroll holds your employee records, and how often your projects change. Save this one for your demo. Bring your ERP and your list of dimensions, and we'll show you the sync with a setup like yours. Book a demo.
2. Can we keep the cards we already have?
Another frequently asked question was about existing corporate cards from AMEX or Mastercard or even specialty carsds like WEX. One construction firm's owners refused to move off their fuel card provider, so any tool had to work with it. A nonprofit with two card programs downloads statements every week into a shared folder for each cardholder. A membership association's finance lead said they would believe a card feed works when they saw it in writing.
That last instinct is the right one. Before you sign, ask for written confirmation that the vendor can pull transactions from your bank or card processor, how often, and what happens if a feed can't be set up. Also ask what happens when a receipt is uploaded before the charge posts.
DATABASICS doesn't require you to switch cards. The DATABASICS Visa® Commercial Card is optional. Whether your bank or processor can feed transactions directly is the part that depends on you, so raise it early. Ask about your cards in a demo.
3. Can people code to the right job, grant, or cost center without memorizing codes?
This is a common question because it can be some of the most painful stories. A construction controller codes some expenses to overhead (a GL account only) and others to job, cost code, and category. She can't expect every employee to know which fields apply. Another firm has one person whose full-time job is working out cost codes for fuel and card charges after the fact. A consultancy pays an outside consultant to post negative time entries every time someone charges a closed project. And a membership association wanted to split one director's trip across a board meeting, a committee and a member visit.
What to look for:
- Fields that change based on what's selected, so picking a job-related GL account asks for a job and cost code
- Lists limited to each person's projects or grants, with closed ones hidden
- A choice between a warning and a hard stop when something is missing
- Splits by percentage or preset allocation
- Corrections by authorized people, with every change logged
How this works for you depends on your dimensions and how strictly you want to enforce them. Bring a few of your messiest real expenses to a demo and watch how they get coded. Book a demo.
4. Will incomplete or out-of-policy reports stop before they reach accounting?
This question has to do with policy management. A controller worried cardholders would snap a photo and submit it with no coding. A heavy civil contractor wanted an approval step before anything reaches the journal. One finance team wanted to review only the 25 flagged transactions, not hundreds, and another wanted reminders to replace their monthly chase emails.
A good question for your demo is to ask about required fields and policy checks at submission, before a manager opens the report, and confirm nothing posts to the ERP until final approval. The approval path itself, by project, dollar amount, role or person, is specific to your organization. Map yours out and bring it to a demo.
5. What will it really cost, and how long until we're live?
And here's an essential practical question: are there any other costs or fees I'm not thinking of? Ask about one-time setup, integration and training fees, what drives the subscription price, and what changes at renewal. Timelines depend on how ready your data is and how many systems you connect. Current plans are on the pricing page, and a demo is the fastest way to get a quote for your setup.
Bring these questions with you
Every one of these questions is about context: which job, which grant, which card, who approved it and why. Your timesheets and expense reports already hold that context. Most teams never get to use it.
Try it on your own data. Context In, Answers Out is a free set of AI prompt ideas for project timesheets and expense reports. Use them with your company-approved AI assistant to find answers in the data you already capture.
Get the prompt pack
Ready to ask these yourself? Book a demo.
