Gabrielle ‘Gaby’ Toledano: Leading Internal Teams to Outsized Growth and Expansion

Keystone is an innovative strategy and economics consulting firm delivering transformative ideas and uncommon service to global brands on leading-edge challenges related to technology and business model innovation. 

Gabrielle 'Gaby' Toledano is the COO at Keystone Strategy. After earning her undergraduate degree in Humanities and then her Master's in Education from Stanford and spending a year on a Rotary Scholarship in Santiago, Chile, Gabrielle began her career in Human Resources (HR) at Oracle and then at Microsoft. She left Microsoft, after 7 years to lead HR and Facilities at Siebel Systems. Siebel was acquired by Oracle while she was serving the company.  From there, Gabrielle spent the next 11 years leading global HR and Facilities at Electronic Arts (EA) which was a unique experience as it was transformed from a traditional packaged-goods company into a digital direct-to-consumer interactive gaming leader. Gabrielle's efforts there focused on retooling every aspect of how EA did business, including major shifts in the talent composition of the company. 

After EA's digital transformation and three CEOs during her tenure, Gabrielle joined Tesla as the Chief Human Resources Officer (CHRO) and implemented the HR, Security, Facilities and Environment, Health and Safety team and infrastructure required to scale the business. For the last decade, she has served as an advisor and board member for a variety of public and pre-IPO technology companies. 

Today, Gabrielle is at Keystone as its Chief Operating Officer, building out the finance, HR, recruiting, IT, labs and office management functions. Previously, she was a board member at Keystone Strategy for a number of years, and had a first-hand view into the brilliant team, and understood the firm's aggressive growth strategy. Gabrielle considers as an honor to use her 30 years of industry experience to build out a world-class operations function based on the principles that she values the most for a service organization: transparency, innovation, simplicity, technology-enabled service, and a phenomenal client experience. 

An Exceptional Leader and A Change Agent 

Gabrielle has learnt that it is important to work hard, focus on the job one has today vs. what's next. One must do today's job well, and then they will move up. She has also learnt the importance of doing what is said one would do, authenticity with everyone at all levels. Gabrielle doesn't have any interest in politics, but she is a change agent and an achiever.  

It is important to bring people as one moves along. Gabrielle has hired so many people again and again who have worked for her or with her in the past, those who have demonstrated excellence and strong values day-to-day. Gabrielle believes in making sure that one enjoys the work and those with whom they work. She has worked for some tough bosses and there were difficult moments, but she has always tried to apply empathy and not to be defensive, while also finding her voice. Lasting and great leaders respect honest, authentic and smart contributors, not unopinionated followers. 

Balancing Challenges to Encourage Excellence 

Gabrielle remembers early on having peers who were so ambitious that they competed with her. She didn't like that kind of team environment and learned to find others who wanted to work well together and encourage excellence mutually and with support. When she had her children, she found being a great mom, partner to her spouse and employee was hard to balance. She would work and miss time with her kids or husband or she'd choose family time and sometimes not be there 24X7 for the company's CEO or the team. Gabrielle says, "You can have it all, but there will be times when there is an imbalance. Make sure you have a partner who is supportive of your ambitions and interests and trade off the work and home duties depending on where you each are in your professional career. If you decide to leave an organization, due it with dignity, gratitude and respect; don't burn bridges and remember that you are ready for the next thing because of what you learned at this thing!" 

Grit and Determination to Excel Transformational Leadership 

Gabrielle believes that every innovative and transformational leader should have grit and determination, passion and curiosity, and both humility and courage. A great leader is a brilliant thinker and problem solver but is also a great listener and a people leader, with empathy and intuition to drive as many decisions as does data they collect for the same decisions. 

Leveraging Innovation to Understand Complex Eco-Systems 

At Keystone Strategy, diverse teams are purpose-built to leverage a triad of skills including business, technology, and economics. This triad sets their work apart and offers the company a unique vantage to analyze and understand the complex ecosystems its clients face as well as provides Keystone Strategy an edge to develop bold strategies that have a far-reaching impact for its clients. 

Working with Disruptive Technologies with Skilled Capabilities 

Keystone Strategy has been working with disruptive technologies for nearly two decades. Recently, its chairman co-authored a book entitled Competing in the Age of AI, which draws on the firm's decades of experience and provides a clear framework for transforming the operating model and business strategy. By reinventing the firm around data, analytics, and AI, companies can remove traditional constraints on scale, scope, and learning that have restricted business growth for hundreds of years. Today's successful leaders must confront silos and fragmented legacy systems, add skilled capabilities, and retool culture to support innovation. 

Blending Expertise for Future Gains 

Speaking in general terms for the tech industry, the trends are very clear. The application of AI and machine learning to every aspect of how companies do their work will continue to have a staggering impact on business and the economy. It is unfortunate, but companies left without a digital strategy will not be able to compete. But, for tech firms that build enabling technology, the future is bright. As a long time, HR professional and executive, Gabrielle believes it is an interesting world, where transformational automation is not just sunsetting manufacturing jobs, but white-collar work as well, and it is an incredible time to be associated with Keystone Strategy, a firm deeply involved in leading the thinking around digital transformation and complicated problem-solving. 

Keystone Strategy's consultancy is a unique blend of economics, tech, and legal expertise. at the firm works at the intersection of these disciplines, helping companies chart their digital transformation, and enabling clients navigate complex software and tax-related litigation. Today, Keystone is poised to double in size over the next few years, delivering transformativedeas to some of the world's most amazing brands. Its brilliant consultants, their passion for the business, and the company's deep relationships with recognized academic experts gives Gabrielle and her team the intellectual capital needed to help companies solve some of their most complex challenges. 

A Word of Advice for Emerging Women Leaders 

For emerging women leader's, Gabrielle asks them to take a stand and have a point of view, but they must also respect their audience and teachers at all times, as there is always another perspective and way of thinking about a problem or a solution. She further advices, emerging leaders to make sure they focus on hiring a great team to work with them. Gabrielle has always learned from people who have worked for her, as well as learned from peers and leaders above her. She encourages women leaders of tomorrow to not just focus on details and execution day-to-day, but stop and consider the bigger picture, the strategy for their company or organization as they look ahead. They must say yes more than saying no; and they must take a risk.  

Moreover, she says, "Don't become complacent; change it up now and again. I come back to my earlier comment – surround yourself with a team that is not only smart, but driven, open-minded, diverse, and kind. Do not underestimate the importance of assessing the values of those with whom you work. Values such as integrity, teamwork, respect, inclusiveness, community and many others that come to mind, are, if not more, important to assess than experience, skills and capabilities when you are hiring someone."