Do you have an Apple Store anywhere within reasonable distance?

The reason I’m suggesting seeking their guidance is because they are the company best known for creating user friendly interfaces (since you’re dealing with an older and much less tech-savvy sales staff).

Call ahead and make an appointment with a manager or someone from the Genius Bar and explain the situation just as you have here.

I would be flat out amazed if they didn’t already have more than one App in the AppStore designed for exactly what your business needs. And now that they recently added the iPad minis, they’re more convenient yet.

If you hope to bring all those dinosaurs out of the Paleolithic age, you really need to make it as painless as possible or they’ll just give up. Apple is the company which puts the most planning into specifically creating idiot-proof systems which even a child can learn.

There may be others here who may have more actual experience with business integration of tablets and I’ve sent an email to one and I hope he’ll have more specific info.

Do you have some concrete, specific reason to consider tablets over traditional PCs and/or POS devices? One that could be stated in a sentence? It could be, “Our sales staff would look really cool and modern carrying tablets around.” Or, “We move around so much, why can’t we take our work with us?” Both those things seem really hard to justify in a typical traditional brick and mortar setting, but they certainly happen.

Just being old isn’t a problem by itself. Strings of text mostly don’t care what hardware they’re processed on. Business IT is often decades old, and that’s often beneficial because the oldest stuff is proven and compatible (with other business products anyway). No kidding: things like ATMs and smarter vending machines still use a lot of OS/2, Windows NT, and even DOS.

Also, have you considered maybe this is or could be just a first step? Modernizing the backend (moving to a modern database?) is probably much harder than modernizing sales-level user interface. Once both are working and tested, they know they can work with the PCs they have, maybe they’ll be ready to jump into a sexy HTML5 interface on a tablet.

Also, think about vendor lock-in. I would be pretty surprised if tech officers and sales VPs aren’t at least aware of advances in technology, but another thing to consider is the tablet market is still maturing and they want to avoid being locked into something that might not be around in 2019. Nobody knows who will be dominating the tablet market in 5 years. It probably won’t be Microsoft, but there is probably a better than even chance that it won’t be Apple either. Microsoft aborted this somewhat with Windows 8, but for the most part Windows PCs are backwards compatible going back decades. Much as I think Windows is a smouldering shitpile, it’s so entrenched in the world of business that it’s extremely hard to ignore its productivity value. If they’re orienting toward the PC, they probably have reasons.*

History lesson: “modern” tablets (think circa 2002) actually sort of started as a business-oriented product by Microsoft of all people, probably aimed at people in situations like yours. Maybe a good idea, but I don’t think they ended up filling any particular need that wasn’t already filled by laptops or even stationary PCs. Tablets weren’t commercially successful until Google and Apple began pushing them at consumers.

* One reason plays into @Buttonstc‘s point. Jumping ship to Apple or someone else might be trading one form of vendor lock-in for another, and it might be better to stick with what evil you know. You don’t want idiot-proofing, unless your sales staff really is full of idiots; you want future-proofing.

My own advice would be to take some of the key decision makers to a similar retailer’s (not a competitor’s) store (one that you wish to emulate, at least in terms of its IT functions as they apply to retail sales) and show how it’s done there. In a word, “benchmark”. People and businesses who are not in direct competition with you for sales will often be very willing to show you the nuts and bolts of how business can be done better.

The real issue is trying to get old dogs to learn new tricks. I find that, at a mere 40, I am less mentally agile than I was, so there really is no great solution. In other words, your biggest challenge won’t be the hardware or the software, but the wetware.

And while @Buttonstc is correct that Apple is decent with design, they will cost you more, and lock you in harder, while not providing any actual end-user benefit over cheaper, more open Android counterparts; both use practically the same UI, especially in apps.

Also, how strong are your SQL skills? I really think that for what your company data needs are, you all need a database administrator (even if that means you taking a few night classes to learn Oracle). Yeah, HTML makes a good front end, and can do basic forms well enough to impersonate a kludgy attempt at a database, but you need some heavy-duty database action if you want to get shit done, and I’m not sure if you have that going on.

BTW, I know of at least one place that was still using a Commodore 64 as recently as 6 years ago. It still fit their meager needs for their small business, so they didn’t bother updating/upgrading for a loooooong time.

Just curious, @jerv: why Oracle? I got the impression reading this that the OP works for a small-ish brick and mortar firm. Why wouldn’t MySQL (MariaSQL?) be sufficient?

I assumed they weren’t using flatfiles, but maybe I was wrong. :-\

If I had to guess, you’ve got an IT team that is out of their league and trying to kludge together a solution as they teach themselves. I think going with a 3rd party product makes a lot of sense. It should be much cheaper, more polished, and have a much better user interface.

If I were you, I’d start looking at alternatives and present them to your boss. It might land you a promotion or a raise. Crunch the cost of the alternatives so they have a comparison. Your use case almost certainly doesn’t necessitate a custom app which would probably easily run in the tens of thousands of dollars. I think your IT guys are looking for job security by locking you in to something that will require you to keep them around for a very long time.

@bolwerk Well, yes. My point was merely that their needs are greater that the inherent database capabilities of IE or a simple Excel spreadsheet. I assumed they were in Flatland.

@gorillapaws Nothing says “job security” like spaghetti code!

@jerv: hmm, yeah, I can see where I might be wrong. I figured the web application must be interacting with something on the back end, but “something” could be a dated relational DBS like mSQL or an utter piece of crap Access. She mentioned that they do input it into a computer from handwritten notes. (Maybe @nayeight could clarify this?) A little off-topic, but you might find it amusing: bumped into this by chance today.

@bolwerk I half suspect that data entry for the OP may involve LOAD “MULTIPLAN”,8,1