Crisis is asking captains of industry to spend a night in a homeless shelter and help raise £100,000 for its Big Cheese Challenge.
The campaign aims to recruit 10 chief executives from leading UK companies.
Each will be expected to raise £10,000 for the campaign through sponsorship from their employees and peers.
The Big Cheese Challenge will involve a brainstorming session where the bosses will be asked to use their experience in running large businesses to help Crisis think strategically about solving the problem of homelessness.
"We're always looking for opportunities to work with the corporate sector but this is the first time we've targeted chief executives specifically,
said a Crisis spokesperson. "We started with the idea of a sponsored 'sleep in' but didn't want to waste the opportunity to get an extremely influential and knowledgeable group of people together at the same time."
Although the money raised will not be earmarked for any specific area of the charity's work, Crisis is planning to launch a range of new projects later this year. These will include a scheme to offer financial rewards to former rough sleepers to help pay for employment training and courses.
The event will be hosted at the charity's innovative 365 shelter, which the charity has designed to try and highlight new ways of looking at daytime homelessness, and will offer guests education, sports and arts classes.