All newcomers to Toronto have their own first impressions of this city.

When Will Fleissig first came here as a visitor in 2011, his lasting memory was of the waterfront.

That was before the job of president and CEO of Waterfront Toronto was even open. It just so happens that, five years later, Fleissig would be back to fill that job.

He's lived and worked across the U.S., and comes here from San Francisco as a developer and urban planner. He has cultivated a reputation for civic engagement.

He remembers thinking on his first visit that the city and the waterfront seemed fragmented.

"It was the city's relationship to waterfront that struck me," he said. "Boston, New York — in all these cities, the waterfront is where everything began. So I tried to imagine the viewpoint those first newcomers had of the place from the water."

He remembered driving past the condos, catching only a snippet of the island and the Harbourfront, and then into downtown. He said it was like a haiku of Toronto — a not quite complete picture of the city.

In San Francisco, where he lived, the waterfront is well utilized. He liked it there, but there was something Toronto has that San Francisco is missing. Fleissig said that had to do with income inequality.

He has two daughters who were attending private school in the Bay area. He said his children were interacting with the "one per cent of the one per cent," extremely weathly people. He wanted more diversity.

"San Francisco, as beautiful and poetic as it is, is segregated diversity — by geography, economics, culture and race," he said. "For me, this is very personal."

Waterfront job posting

It was the personal connection that made all the difference for Fleissig. His prior trip to Toronto, his children and something the Waterfront Toronto role offered in its job description.

It started when Fleissig was called and asked to take a look at the job posting for Waterfront Toronto. As he remembered, the posting just "talks about all the usual stuff — great opportunity, green, jobs, infrastructure, bringing people back to the waterfront."

It was one line that caught him off guard.

"The very last line: 'To change the perception of Torontonians, Ontarians, Canadians and the world about Toronto,'" he said. "The hair on the back of my neck stood up. I've never read that before anywhere, and I've done work all over the U.S. and the world. That was unique. This was the Magna Carta for the waterfront."