Almost always yes.
The useful questions are what it costs, how reliable it will be, and what happens when one side changes. Those have less predictable answers, and they are what decides whether the project is worth doing.
How do two systems actually talk to each other?
Through an API, which is a door the software vendor built deliberately so other programs can come in.
Think of it as a service counter. The software will not let you wander into its database, but it will accept specific requests at the counter and hand back specific things. Create a contact. Give me this order. Tell me if this date is free.
Everything else follows from whether that counter exists and what it will accept.
What if the software has no API?
Then you have three options, in descending order of comfort.
A middleware service. Tools like these sit between systems and support hundreds of products. If both of yours are on the list, this is usually the cheapest and most reliable route, and it needs no custom code.
File exchange. One system exports a file on a schedule, the other imports it. Unglamorous, dependable, and fine when information does not need to move instantly.
Screen scraping or automated clicking. Software that pretends to be a person using the interface. This works, and it breaks whenever the interface changes, which is often. Treat it as a last resort with a known expiry date.
If a product has no API and no middleware support, that is worth knowing before you commit further to it.
What are the connections most businesses actually need?
Four, and they cover the majority of what I get asked for.
Website enquiry into CRM, with the campaign source attached. Without this you cannot tell which advertising produced customers, only which produced forms.
Bookings into calendar, both directions, so availability shown online reflects reality and nobody double books.
Orders or invoices into accounting, so the same numbers are not typed twice and the month end is not archaeology.
Customer records into email marketing, so a list is current rather than a snapshot from whenever somebody last exported it.
None of these are exotic. All of them are usually available through middleware.
What does it cost?
The honest answer is a wide range, and the thing that moves it is not what you would expect.
A middleware connection between two well supported products is a small job, often a few hours of configuration.
A custom integration to something obscure, or something with a badly documented API, costs several times that. And the cost driver is rarely the code. It is handling the situations where things go wrong: what happens when the other system is down, when a record already exists, when somebody submits the same form twice.
That error handling is most of the work and it is the part cheap quotes leave out. It is also the part that determines whether you trust the system in six months.
What breaks, and how often?
Three things, predictably.
The other side changes. Vendors update APIs. Usually with notice, sometimes not. A well built integration fails visibly when this happens. A poorly built one fails silently, which is worse.
Credentials expire. Keys and tokens have lifetimes. Somebody has to renew them, and if nobody is responsible, this is the most common cause of an integration quietly stopping.
Somebody changes a field. A person renames a column or adds a required field, and the connection that depended on it stops working. Nobody connects the two events for a week.
All three are survivable with monitoring. None are survivable without it.
What should I insist on?
Two things, and they cost little at build time.
An alert when it fails. An email or a message to somebody named, the moment something does not go through. Silent failure is the difference between an inconvenience and three weeks of lost enquiries.
A record of what moved. A log showing what was sent and what came back. When something is missing, this is the difference between diagnosing it in ten minutes and arguing about whose system lost it.
Ask for both explicitly. They are frequently omitted, not out of dishonesty, but because they are invisible in a demonstration.
Is it worth doing?
Usually, and the case is easier to make than people expect.
Count the retyping. If somebody spends thirty minutes a day moving information between two systems, that is around ten hours a month, permanently, and it grows with the business. Most integrations pay for themselves inside a year on that alone.
The larger benefit is that the information stops disagreeing with itself. When two systems hold the same customer with different details, every decision made from either is slightly wrong, and nobody knows which one to believe.
What would I do first?
List every place somebody types the same thing twice.
That list is your integration roadmap, in priority order, and it takes an afternoon to produce. Start with whichever line makes someone in your team audibly sigh.
We build integrations with failure alerts and logging as standard, because an integration nobody is watching is a system nobody can trust. Tell us what you are working on.