Peter Halkett is leaving Kathmandu after eight years of leading the outdoor clothing retailer.
Mr Halkett, 53, said in a statement that he felt it was time to take a break and he intended to take up to a year off before looking for a fresh challenge.
The share market took the news badly, shaving 17 cents, or 5 percent, off the share price to $3.20.
The chairman, David Kirk, said Mr Halkett had previously said five years was long enough to lead a trans-Tasman listed company.
Mr Kirk agreed it was not the best news for the company.
"No, in the short-term it certainly isn't, but the company is very well positioned in its markets and has a very solid and clear growth strategy. I'm sure that will be recognised by investors."
He said the company was taking normal steps for replacement and would look at both internal and external candidates.
"It's always very difficult to predict. Peter has a three-month notice period and we'll certainly be moving ahead on the process of finding a replacement as quickly as we can."