Women's Tennis Association chief executive Steve Simon says his organisation are evaluating the "challenging topic" of taking the sport to Saudi Arabia.
Saudi Arabia has reportedly approached the women's Tour about hosting an event, potentially the prestigious end-of-season Finals.
The WTA has yet to enter any formal discussions with Saudi officials, but Simon accompanied two players and organisation representatives to the Gulf state recently to get a closer look at their plans.
Simon is well aware striking a deal with Saudi Arabia would be controversial given the region's human rights issues and treatment of the LGBTQ+ community.
"It's a very difficult and challenging topic that is being measured by many groups right now," Smith told reporters at a WTA event in London on Friday.
"In February I went to Saudi Arabia to see it for myself. We took a couple of players and some reps as well. We wanted to see what the change was.
"The Saudis are talking to a lot of people and a lot of different sports right now. I think everybody's evaluating what this means and how do you how do you move forward with that?"
As well as the Saudi interest in women's tennis, ATP chairman Andrea Gaudenzi said the men's Tour has had "positive" discussions with Saudi Arabia's Public Investment Fund about a potential deal.
That announcement drew criticism from tennis legends John McEnroe and Chris Evert, with 'sports-washing' accusations once again aimed at the Saudis.
Women's tennis was played in nearby Qatar from 2008 to 2010 when Doha hosted the WTA Finals.
And Simon believes the sport could prove a change-agent in the region if Saudi authorities continue to adopt a more progressive
"In terms of Saudi we need to look at it very seriously and decide how you take it on and involve them," he said.
"You want them to do what they are talking about right now and advance the opportunities for women in the country, to make it better. You need to support that, you can't walk away from that.
"I'm not saying Saudi is a place we should be doing business with or not but they are making huge changes.
"Where they were five years ago to where they are today with women's issues is significant. The question is should we support it and how do we support it?"
- 'This is a big one' -
Simon is keen to involve his players as much as possible given the potential for a backlash.
"I want to understand what their perception would be. This is a big one. And it's a controversial one and I value their voice," he said.
"There are still tons of issues in Saudi Arabia, with respect to the LGBTQ+ community there, that have to be done. We have had conversations and we will continue to have conversations.
"The advancement for women's rights and where they are coming from is transformational right now. They have a long way to go but they are making huge strides."
Asked if gay players would be safe in Saudi Arabia, Simon added: "Yeah. It's something that we don't agree with. There's still progress that has to be made.
"We've had direct conversations about that issue. It's a very sensitive issue over there, probably take time to get your arms around."
Simon was speaking at an event to celebrate the foundation of the WTA 50 years ago, so with the Saudi issue such a hot topic it was fitting that the trail-blazing Billie Jean King was in attendance.
King was the driving force behind the WTA's formation and remains a advocate for equality.
Asked if she would support a women's tournament in Saudi Arabia, King said: "I'm a huge believer in engagement. How are we going to change things if we don't engage. But it's hard. I understand totally (the difficulties)."
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