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Spotlight:
Jason Warner

CEO at Poolside

As the former CTO at Github, Jason Warner helped revolutionize how developers work. And as the founder of Poolside, he is further unlocking their potential by enabling developers to leverage large language models as part of the software creation process.

“Every human on the planet will eventually be touched by AI in a positive sense. For software, this is going to allow more people to express themselves and get their ideas out there,” he said.

Warner spoke with Riviera Partners to share his key lessons learned in leadership, team building, and what Silicon Valley often gets wrong about both.

01

Learn,
don’t copy

02

Remember where
value is produced

03

Greatness is
engineered

04

Star players don’t
always make star teams

01

Learn,
don’t copy

Success in business often comes down to identifying and exploiting a market gap. It’s no different for a career. “Honestly, what inspired me to go into leadership was bad bosses,” Warner said. 

Far too often, aspiring leaders seek to imitate successful leaders without understanding why they were successful in the first place. The result is leadership cosplay. 

“I wanted to show there was a different way, where you could have an outsized outcome without trying to imitate Steve Jobs or Elon Musk. While they’re idolized in Silicon Valley, people tend to overlook the negative consequences of their style,” Warner said.

“You can’t copy. You have to learn. You need to look at the context of the situation to learn a lesson that can then be adapted to your situation.”

“You can’t copy. You have to learn. You need to look at the context of the situation to learn a lesson that can then be adapted to your situation.”

02

Remember where
value is produced

Warner recalls a compliment he originally took as an insult: “I was early in my engineering management career, and my boss said that with my personality I should probably be in marketing or sales. I couldn’t think of a worst possible thing for me to go do.”

It was only later that Warner discovered the potential that can come from being an engineering leader who is built like a CEO. By keeping a foot in both worlds, Warner was able to win the respect of engineers when wearing his CEO hat while ensuring engineering has a seat at the table during critical business discussions. 

“Engineering is where value is produced, but that is not how Silicon Valley is run. If you go into a board meeting, think about how many times the head of engineering talks. It’s almost always the heads of product, sales, marketing, or operations leading the discussion – that’s who’s in the room. My view is that the head of engineering should be the second most important person in the company outside the CEO,” Warner said.

“The head of engineering should be the second most important person in the company outside the CEO.”

03

Greatness is
engineered

While youth has the energy, Warner believes that more experienced founders still have the advantage. 

“I think it’s a superpower to be a founder when you’ve got more experience,” he said. “The thought generally is that the young will run through walls and never give up, but have to make a thousand decisions over the next two weeks to make the ones that matter. An experienced founder understands which four decisions actually matter, and doesn’t get bogged down with the rest.”

“If you’re young, you’re going to get to the decisions that matter by sheer luck, but you won’t know if it’s right or wrong. That’s not how great companies are built. That’s luck. Great companies are engineered, and engineering means understanding what is worth your time, energy, and effort, and what is not.”

“Great companies are engineered, and engineering means understanding what is worth your time, energy, and effort, and what is not.”

04

Star players don’t
always make star teams

When building a team, culture must take precedence over even the most talented individuals. If you sacrifice your ideals to accommodate a flawed superstar, the damage it can do to the team will put you in last place. 

“I wrote a blog post about this. I had someone on a team once that was clearly heads and shoulders above everybody else, but he was such a drag on me and the team culture. He was by far the best engineer on the team, but when I finally let him go the team’s productivity shot through the roof,” Warner said.

Because the engineer dominated so much of the team’s energy and well-being, it prevented other role players from developing into starting players. Leaders must focus on maximizing long-term success, even if that means sacrificing short-term results.

“If you have a weak culture, you’ll always be fearful of losing your star. ‘If we let that person go, we’re in trouble.’ If you have a system, an approach, a culture, you can overcome that loss and maintain a championship team.”

“If you have a weak culture, you are fearful of losing your star. If you have a system, an approach, a culture, you can overcome that loss and maintain a championship team.

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