VolunteerOne of the huge challenges of putting on a running or triathlon event is finding and coordinating volunteers. How profitable event companies convince people to work for them for free in the first place is a mystery to me (note to self for future blog post).
However, this common need for free labor can be seized upon and many race directors will be prepared to dish you a free entry for a future race if you offer, or recruit someone else, to help out at one of their events. I've even helped out the day before at registration (which is a far better job than being stuck on a street corner with an orange vest and a flag for hours) and raced the next day. It was a nice little arrangement.
WinOn the couple of rare occasions I've won an event I've usually been invited back the next year for free. It's worth asking if it's not offered to you. Unfortunately, attracting fast athletes to races seems less and less of a priority (see Competitor Groups recent decision to dump support of elite athlete fields) so simply having good performances might not get you a comped entry.
If you're speedy try sending a nice resume, and promising some collateral marketing, like a blog post previewing the race and some social media love and you might get in for nix. Finish Line Productions in California has the novel idea of giving away race credits as age group prizes at its events to use for future events.
CorporateTeam Building! Running a relay with your work buddies is a much better option than falling back into each others arms in the conference room IMHO. I've had great times at corporate paid events; a team adventure race at the Sea Otter Classic, Seagate paid my entry for years to the Wharf to Wharf when they were the major sponsor and Tuesday I've taken the afternoon off work to go run the JP Morgan Chase Corporate Challenge in San Francisco. If you work it right you can get time off work, and travel reimbursed as well, in exchange for your competitive endorphin fix. Win, win, win.
Don't wait around for it to be offered the opportunity either. Find a team event, some sporty work mates and pitch it to your Corporate Communications people. If you do it right you'll come across as a motivated team oriented employee and not distracted endurance junkie who can't wait to get out of the office.