Writing skills

You could hire a writer from the Warriors for Hire section if you want to outsource it.
Otherwise, you have to start practicing until you are happy with your email.

Writing letter is something different from writing content..Everyone may not be good at writing letters..I would advice you to hire someone who specializes at writing letters..If you don't wanna spend money ask your friends out as they may knowledge about writing letters...:-)

I wouldn't go the route of email. It's too easy for your email to get lost in their email inbox, along with the hundreds of other emails they likely get each day.

I'd hit them with a direct mail package... maybe even lumpy mail to get their attention. Done right, they'd be falling over themselves to contact you which gives you massive leverage in closing the sale.

Mike

There are a couple things you should consider before putting pen to paper or finger tips to keyboard. Do you actually know the person you are trying to contact? And, why should they be dealing with you (versus your competition)? If you already know the person, then skip the email and pick up the phone. If you can't get through directly to that person, then schedule an appointment with the gatekeeper (secretary or whoever is there) when you can talk to this person by phone. When you get a chance to speak to them, cut to the chase fast. If you decide to write something to the person ahead of time anyway, go with a written letter which briefly details your idea and mentions a time when you will contact by telephone. There's a chance this letter won't be read but at least you tried. An email might seem like the fastest way to reach someone but it can also be perceived as spam. So if you decide on the email anyway, just keep it short and to the point. Lead with your biggest benefit, such as why they should buy from your company rather than a competitor. The potential customer will always think in terms of "What's in it for me?" Keep those points in mind as you craft your email. Once you have sent the email, don't assume it's been read. Follow up with another email or phone call.

Like any marketing campaign, you'll have to determine what the competition is doing and how you can compete against that. Most large booster clubs are already working with established vendors. What can you offer that they don't?

One angle is that same-season sports booster clubs end up competing with each other, each offering similar items. If the football team uses vendor X, go to the cheerleader booster club with a plan--show how you can offer merch the other booster club does not sell.

It helps to have one unique "high profile" item that starts the buzz with kids and parents. "Cool, they have a 37-foot beer mug you can swim in!" or whatever. Add on sales are easy from there.

Try the same angle with wrestling/swimming/basketball in winter, and spring sports like baseball/track and field.

If you're not a good writer, I would tell you to consider outsourcing it. If you don't have the money to afford outsourcing, take a look at some online resources to improve copywriting skills.