Chief Operations Officer
, Chief Operations Officer

Few people know Silicon Valley like Gabrielle Toledano. Most recently she has been working in the venture capital industry as an Executive in Residence at Comcast Ventures. She’s expanding her leadership breadth by recently accepting a Chief Operating Officer role where she will lead HR, but also Finance, Marketing, Communications, IT and other operational functions at Keystone Strategy. Gabrielle also sits on the Board of Directors of Namely, Glu Mobile and Visier. Moving effortlessly between industry sectors and now functions, she has held senior leadership roles at Microsoft, Siebel Systems, Electronic Arts and Tesla.

Trailblazer Experience
Latest Transition

Entertainment → Consulting

Other Sectors

Data & analytics
Venture Capital





When Gabrielle Toledano made her first big career switch, she had to learn fast. Leaving a job at Microsoft for a C-suite role as Chief Human Resources Officer at software company Siebel Systems (now part of Oracle Corporation), she suddenly found herself leading a team of older, more seasoned colleagues.

“I quickly learned to appreciate the experience of those around me. I was empathetic as a leader and appreciative of the team, and at the same time not afraid to make the calls and be the leader I had been hired to be” she says.

The experience taught her the value of having experienced specialists on her team to rely on. “At a young age, I learned how to recruit and promote people who were better than me in their own crafts, and often knew more than I did,” she says. “I always surrounded myself with the best people I could get and focused on creating positive and collaborative team dynamics.”

As she has progressed in her Silicon Valley career, moving seamlessly across the enterprise and consumer sectors and now into technology consulting, Toledano has herself become a mentor and thought leader. One of her proudest achievements is having helped 16 HR leaders on their journeys to become CHROs themselves. “I enjoy seeking out high potential and encouraging them to go for it,” she says.

“I always surrounded myself with the best people I could get and focused on creating positive and collaborative team dynamics”

Mark Moreau, Co-Head of Europe
Interview with
Mark Moreau
Co-Head of Europe

Her journey has been shaped by a hunger to work for inspiring and ambitious CEOs. “I am attracted to – rather than fearful of – big challenges, and people with courage and strong points of view.”

Toledano was Chief Talent Officer at Electronic Arts (EA), joining in 2006 when it was undergoing major transformation to a direct-to-consumer subscription business. She arrived at a company which had just lost a class action lawsuit. The company culture needed to change in order for it to grow. At one point during her EA tenure, its market capitalisation fell to below $3 billion, she recalls. “I’m proud of riding the downturn and working with the leadership team to turn that business around. When I left it had risen to above $30 billion in market cap.”

“The CHRO,” she says, “has a key role in any such corporate transformation. The CHRO must know as much about the business as anyone else at the executive table. You need to intimately understand what skills are needed in order to recruit and promote the right people who can transform the business.”

“I am attracted to – rather than fearful of – big challenges, and people with courage and strong points of view”

Most of her time has been in the technology sector, but she worked in manufacturing at Tesla, where she joined as Chief People Officer in 2017. She learned valuable lessons around labor issues and safety, and once again brought in key specialists to help her.

She identifies the four key attributes of great leadership as: authenticity, integrity – or more specifically honesty and fair mindedness – vision and accountability. As she looks to the future, she predicts a “rebalancing” of the leadership qualities most valued in Silicon Valley, with a shift in emphasis towards integrity, empowerment and resilience, and less of an obsession with charisma.

Most importantly, she says, leaders must wake up to the demands of digital native consumers and digital native workers. “They’ve grown up on social networks and now anyone can be called out for any bad behaviour publicly. This is a good thing. Maybe the bad behaviour will stop,” she says.

Which is why leaders need HR experts at the table and need their own people skills themselves, she says. “That top HR job is high-risk. You better be a great listener, you better be a learner, you better understand the sensitivities of all generations and be open to changing your mindset.”

Access the research
Convergence Trailblazers

Register for access and receive an email invitation to download SRI's Convergence Trailblazers research document.