I am not familiar with this at all, so I am imploring you for ideas and help.

We have an employee whose fiance is dying of brain cancer. The guy, age 24, has no health insurance and she is a single mom. We wanted to do a fundraiser (employees only) with a raffle for a weekend getaway.

Is this permissible? Does anyone have any other thoughts of what we could do to raise a substantial sum for these poor kids?

I did a similar thing for a former employee. However we used an offsite facility, and held an auction (all items donated) as well as selling meals (much of the food was donated as well. What we anticipated would raise around $5,000 actually raised 5 times that amount.

If it's employees only, I don't think there would be an issue.

How many employees, locations do you have (might help with ideas)?

At least 100 employees at our headquarters.

We have been running a variety of fundraisers for a co-worker over the last few months who was in a very bad car accident. We sold soda (75 cents) and microwave popcorn ($1.00) for a month which raised over $600.00. The soda was either donated - employees would just pick up another twelve pack when they were shopping - or purchased with proceeds. We've been very lucky because most of it was donated. We also ran coffee sales for a month which brought in about $400.00.
We've had a candy bucket out that anyone can grab a piece and throw some money in. We've also had book sales where employees brought in books and cd's for us to sell. This week we're having a Cinco de Mayo (sp?) food day. An anon employee wanted to donate a rather large amount but have it used for something that we could make even more money on. We're doing a "make your own taco" for five bucks a plate.
We've also done an outside fundraiser at a local watering hole. The owner was kind enough to take ten percent of the net till and donate it. We sold t-shirts and had raffles, etc which came out to over $1000.00.
We know this young lady and her husband will have a long road to recovery so we are trying to put some time between these fundraisers so that noone gets too sick of them!
Her family also has created a web site where we've posted the fact that an account has been opened if anyone wants to contribute. We, her coworkers, have already raised almost five thousand dollars....so far!
We have back offices in other cities (out of state) that have never actually met this young lady, but have had fundraisers of their own because they've worked with her over the phone. One of their ideas was raffling off a basket of goodies, they did one for Valentine's Day and another for St. Patricks day...
Hope this helps a bit....good luck! And I'll also say a prayer for them.....

This came in via PM, I thought I'd share because it is another great idea:

I know that you said that you wanted to do an Employee only fundraiser. But here's what we did - if it will help you. Some bank employees and friends of ours held a fundraiser out-side of the bank. All employees were invited to attend - but since it was away from the bank, they didn't feel obligated.

A local Knights of Columbus Hall offered to let us use the facility. We advertised in all the local papers. We did a silent auction, a live auction, dessert auctions (silent), and served a mexican FEAST! It was VERY successful and so far we've raised $40,000.00. I think that this was in part due to opening it up to the whole community and not making it an event sanctioned by the bank, but having bank employees volunteer in the planning.

This is exactly what we did, it is amazing how the community jumps in to help when someone is in need. I say open it up to all. You will be amazed at how much money you will raise. We raised 28,000.00 in one day with food sale, and silent and live auction. We were getting offers of donations before we even attempted to solicit for items, ended up with over 100 items for auction alone.

Be careful with the raffle issue and how it is connected to the bank as it may be considered a lottery. I know someone who was questioned on that issue in connection with a disaster fundraiser. Also, apparently some cities/states require a license for a raffle? You might want to check on that.

A services auction usually raises quite a bit. You can do the top 5-10 items in a live auction and the rest silent. Examples would be use of a cabin at the lake, a golf outting, a hunting trip, washing/detailing a car, a custom-bulit dog house, a half-day of gardening, giving a dinner party, flying lesson, providing music, tennis lessons, cooking lessons, dog walking, etc. If you can get your executive officers and directors on board, you can usually come up with some good items.

We recently held a silent auction to raise money for Relay for Life. Even though it is mostly employees, we had a few customers get involved. Employees donate items or obtain them from local businesses. Many are great to help when they find out it's for a good cause. We only have around 50 employees and still raised over $1,000 dollars. A big draw was two rival university fans (employees of course) put themselves up to have to wear the other universities shirt for a day - we had two buckets and people would vote with money. We even got front page news in the paper with that one! The president even donated old office chairs that we had replaced and those were a hit.