Simon has been chairman and chief executive of the WTA for eight years but has come under increasing fire from players recently, not least over the decision to stage the Finals outdoors in the Mexican resort of Cancun.
"Maybe it's time for new leadership," 18-times Grand Slam singles champion Navratilova told broadcaster Amazon Prime.
"For me personally, this being a woman's association and being involved for such a long time from the beginning, we’ve only had two women at the head of it. I think it's time, hopefully, when we get a new leader, that it's a woman.
"There's plenty of them that are qualified for the job. It's going to be hard for Steve to stay in the job somehow because everything is pointing the other way right now."
Cancun was named as the venue for the $9 million WTA Finals, which brings together the top eight singles players and doubles partnerships to conclude the season, less than two months before it started on October 29th.
World number one Aryna Sabalenka blasted the WTA over the court conditions after the opening day of group play and said she felt "disrespected" by the standard of organisation at the prestigious event.
The tournament was supposed to conclude on November 5th but rain and high winds meant the semi-final between Iga Swiatek and Sabalenka was not completed until that day, with the final shunted to Monday.
"The players adjusted, they had to," Navratilova added.
"But to come to Cancun in the rainy season? You cannot be hoping it's not going to rain at the premier event for the WTA Tour.
"You have to own the bad decisions you made and make some choices after that.
"There was a sequence of bad decisions. Ultimately, Steve Simon has been the boss for eight years and here we are."
In a letter to the players leaked to the media last week, Simon said the late selection of Cancun to host the showpiece tournament was "based on a number of complicated factors".
He said the WTA accepted responsibility for the poor conditions and signalled changes to the operation of the tour after a series of other complaints from top players about how they are treated.
The WTA said in a statement to Reuters on Friday that it would continue to listen to players about the direction the tour should take.
