Doug Leeds has taken one of the more unlikely career paths in Silicon Valley. After graduating law school, Doug spent two years at a big firm before accepting a policy role at a company that was quickly acquired. Over the next two decades, he worked in various in-house roles at startups, which eventually led to his appointment as CEO of Ask.com, IAC Publishing, and Dictionary.com.
His resume includes scaling global consumer internet brands through key acquisitions, competing against Google during the dot-com boom, and now teaching leadership by persuasion at UC Berkeley Haas School of Business.
Doug met GC AI founder Cecilia Ziniti in 2003, when CZ was still a paralegal at Yahoo. The company had acquired another startup where Doug was in-house counsel, so Doug joined Yahoo by default. Though CZ was early in her career, Doug taught her a great deal about
effective leadership at rapidly growing organizations.
"The definition of leadership that I use in my class is the ability to get other people to do what you want them to do as if it was their own idea,” Doug said.
Doug’s Legal Career Crisis Turned Opportunity
Two years at a big firm was plenty of time for Doug to learn that firm life was not for him.
“They made it easy for me because they told me I could either choose the firm or my family,” Doug said. “I obviously chose my family.”
That ultimatum was an unexpected gift. He jumped ship for a policy role, and when that turned out to be short-term, it was back to the drawing board.
“They gave me a bunch of money to leave, like literally five times my annual salary to go away,” Doug laughs. “It was a fantastic stroke of luck. I thought, great, I'll start a company!”
Business went well, until the dot-com boom went bust. Doug had three daughters to support, so his wife made the practical case for dusting off his law degree. Doug landed an in-house role at Overture, the company that pioneered pay-per-click advertising.
Finally, Doug felt like he had found the right fit. Overture’s legal team was full of people who also didn't particularly want to be lawyers, so everyone got to do things outside their job description. Doug was intentional about getting involved in product and business development, but after the company was acquired by Yahoo, the culture began to shift.
"If I did something well, they would say, ‘you did a great job on that. Now we're going to give it to a business person because a lawyer shouldn't have it,’” Doug recalls. “And if I didn't do well, they would say, this is what happens when you let a lawyer do it."
Realizing he was once again stuck in Legal was jarring for Doug. At Yahoo, his role had a clearly defined perimeter, and Doug kept bumping up against it. The startup mindset where he got to experiment outside his role was gone, and everyone expected him to get in line. Once again, it was time for Doug to leave his law job. And this time, it would be for good.
Competing With Google and Knowing When to Pivot
Doug joined Ask Jeeves (now Ask.com) in 2006 as the SVP of Product Management, right after they had rebranded to the now iconic name. Doug spent two years in product management before being promoted to Chief Strategy Officer. Throughout his tenure at the company, there was one persistent issue: Google.
“Google was kicking our butt,” Doug said. “It wasn't even a product issue, it was more of a brand issue. We would innovate. We'd create new things. We release them. And then within a week, Google would copy them.”
Ask Jeeves had a head start in the search engine game, but in the end, it didn't matter. The search giant was able to invest billions where Ask had hundreds of millions, and Google had already captured 90% of the search market. By the time Doug became an executive, Ask had already spent $100 million on marketing trying to close the gap. The needle hadn't moved, and it wasn't going to.
"I used to be asked all the time: how do you feel about competing with a company whose name has become a verb?” Doug remembers. “And I would say, ‘Ask was a verb first.’"
By 2008, the Ask Jeeves executive team knew they could no longer compete with Google on the original terms. It was time to find new opportunities or drown, which was not an option. Doug got to work acquiring smaller domains to give the company a more diverse portfolio.
A few of his key acquisitions included Dictionary.com, Thesaurus.com, and Reference.com. That same year, the company launched the first search engine for children, Ask Kids.
Ask Jeeves had become a glorified arbitrage business. They would purchase ads on Google, direct them to their own search engine, and then retarget those same customers wherever they went.
“It was just moving the traffic, and we came incredibly good at that,” Doug said. “At one point, we were spending a billion dollars a year on Google ads. At its peak, every ten to twelve searches worldwide on Google had an Ask ad on it.”
The business became extraordinarily profitable by making Google's dominance work in Ask's favor, rather than try to compete with it. The interesting detail most people miss is why Google would allow Ask to make money off of their tech.
In reality, it was a symbiotic relationship. Google needed a credible, visible search competitor to show antitrust regulators that the market wasn't monopolized. Ask was the perfect candidate: a pure search player with real scale that Google could quietly prop up while demonstrating to regulators that competition existed. Their convenient legal angle was Ask’s commercial opportunity.
When Leadership Means Finding a Way to Say Yes Instead of No
Doug's experience navigating Yahoo's rigid org chart and Ask's competitive constraints taught him something that applies just as much to in-house legal as it does to running a business: authority and influence are not the same thing. Confusing these two things is where most lawyers get stuck.
In-house lawyers have authority over what the rules say, but they have almost no direct authority on anyone else. The lawyers who are most effective at getting their way are those who find a way to say yes instead of no.
"The enjoyment I got out of being a lawyer was working with teams to figure out a way to get them to do what I needed them to do,” said Doug. “How do we find a way to say yes instead of saying no?"
Doug calls in-house lawyers who do this well “legal product managers.” And just like a PM on the product team, these lawyers are people who identify the legal risk and build the solution into the product itself.
Note from CZ: I've been saying for years that compliance is sales. The Amazon Alexa story is my favorite example of this: we mapped all 50 states' wiretapping statutes, found the path where the product could exist legally and the customer could trust it, and got to work. Nobody said no. They built the solution, a listening indicator light, into the final product. That is an example of great legal product management.
Improv, Psychological Safety, and a 2,000-Person Experiment
The same leadership skills that made Doug an effective in-house lawyer became what made him successful as a CEO. At IAC Publishing, Doug put his entire company of 2,000 people through improv training.
His senior executives hated it initially, but within weeks, they were telling him it had changed their family lives. The idea behind this exercise was to help the team build trust and get comfortable with public failure.
"Silliness and being able to fail in front of other people in a risk-free way allowed you to build trust so that you could talk about other things," Doug said.
Trust is where opportunities are born, but only in environments where people feel safe enough to surface hidden issues. Doug calls this psychological safety, and he considers it the foundation for everything else, including AI adoption. He says companies where employees are uncomfortable raising concerns about how AI is being used are generally the ones with the biggest governance gaps.
In his current role as an instructor at Berkeley Haas, Doug teaches two classes built around his core leadership philosophy: Leadership by Persuasion and Creativity and Leadership. He's also the co-founder of RSL, Really Simple Licensing, a nonprofit building the ASCAP for internet content in the AI era. His goal is to give creators and publishers a machine-readable standard and a collective rights organization to get compensated when AI companies use their work for training models.
For legal teams navigating AI adoption right now, Doug's framework is a useful compass: build trust with your team first, surface the problems early, and find the path to yes before someone else finds the path around you. GC AI is the tool that helps your team do all three. Try the best legal AI for free today or request a custom demo.
