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The name that we'd like to use for a new web application is a 2-word name (e.g. "Leaf Quick", with a space) that's already a registered trademark in the reverse (e.g. "QuickLeaf", no space).

Both our product and the other company's are hosted web apps, but one is a consumer-facing application for photos and the other (ours) is an accounting application for small businesses in a specific industry vertical.

BTW, the names above are not the real names but are similar in that both names are probably Arbitrary Marks, with both words being common English words that have no meaning in either the photo-editing or accounting business.

What's the chance that our desired name will be infringing? I will be consulting an attorney but don't want to waste time and money on a name that's very likely to infringe.

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A lot depends on how big/rich the other company is and if they want to go after you. Just reversing words may or may not be enough.

Suppose for example you started selling dog food called Mac Big and McDonald's didn't like the idea. Since they have the Big Mac and lots of lawyers and money, they could probably devote far more resources to a legal battle that you would want to.

If you want to be super safe you could ask the other company if they have any objections to what you are planning on doing. You might get lucky and they say no problem or they might just object out of hand. A lot would depend on how you approached them and what kind of company they are.

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You are probably fine since your two businesses are so different from one another. Trademarks are all about likelihood of confusion and it doesn't seem that you could easily confuse a photo site with an accounting site. You could probably even use the two words in the same order if you wanted to.

These days, the fact that both of you run web apps is not that important since almost everything can be sold on the web.

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