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Making Bold Decisions and Taking Risks in Your Career

with Annie Cheng, Claire Hough, Lisa Gelobter & Arezoo Riahi

January 24, 2023
Making Bold Decisions and Taking Risks in Your Career
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Annie (@annie_h_cheng)  is a VP of Engineering at Waymo, an autonomous driving technology company with a mission to make it safe and easy for people and things to get where they are going. Prior to Waymo, Annie was a VP of Engineering at Nauto, an AI-powered automotive data platform that is improving the safety of commercial fleets today and the autonomous fleets of tomorrow.  Before Nauto, Annie was VP of engineering at Yahoo responsible for the multi-billion dollar Web Search and Search Advertising business. Annie has a CS BA degree from Berkeley and MS degree from CMU.

"Sometimes great opportunities are not conventional!"

- Annie Cheng   


As CTO of Carbon Health, Claire leads engineering bringing over 25 years of experience as a technology leader. She has helped over a half dozen companies grow and scale to deliver impact-driving products and services, including Netscape, Napster, Nextag, and Udemy. Claire was named in the Forbes CIO Next List, which recognizes 50 top tech leaders who help shape the future of business and drive game-changing innovation. She is a Limited Partner at Operative Collective.

"Don't let anyone take you down. Give yourself credit, have the resilience, and go after what you are looking for.”

- Claire Hough   


Lisa Gelobter (@LisaGelobter) is the CEO and Founder of tEQuitable. Using technology to make workplaces more equitable, tEQuitable provides a confidential platform to address bias, discrimination, and harassment.

Lisa has worked on products that have been used by billions of people and pioneered several Internet technologies, including Shockwave, Hulu, and the ascent of online video.

Previously, at the Obama White House, Lisa was the Chief Digital Service Officer for the Department of Education, and prior to that she served as the Chief Digital Officer for BET Networks at Viacom.

Lisa has been named one of Inc.'s 100 Women Building America's Most Innovative and Ambitious Businesses, Fast Company’s Most Creative People, and serves on boards for: the Obama Foundation, Times Up, and The Education Trust.

Lisa is one of the first 40 Black women ever to have raised over $1mm in VC funding. She is also proud to be a Black woman with a Computer Science degree. Go STEM!

"The message that I would like to convey is your otherness is what makes you unique and special. It's gonna make you a better engineer."

- Lisa Gelobter   


Arezoo Riah (@arezooriahi) is the first dedicated Head of Equity, Inclusion, and Diversity (EID) at Waymo, an autonomous driving technology company with a mission to make it safe and easy for people and things to get where they’re going.

In her role, Arezoo is responsible for driving and executing a holistic EID strategy, helping Waymo continue recruiting, hiring and championing diversity. As a subject matter expert, Arezoo works closely with the executive team to build Waymo as a company where everyone belongs.

Prior to Waymo, Arezoo led the diversity and belonging programs at Autodesk, where she evolved employee resource groups, designed inclusive hiring training, and launched global mentorship programming. She was also responsible for developing Autodesk’s diversity analytics, launching the company's diversity dashboard to understand trends and hot spots, and leading diversity communications. Prior to Autodesk, Arezoo also held roles in the nonprofit sector, notably serving as Director of TechWomen, an initiative providing professional development to women across the globe, and working with the U.S. Department of State.

Arezoo holds a Masters in Public Policy from The University of Chicago and a Bachelor of Arts in International Affairs from The George Washington University.

Looking for ways to support the show?

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To explore sponsor opportunities, email us at sponsor@sfelc.com

Interested in joining an ELC Peer Group?

ELCs Peer Groups provide a virtual, curated, and ongoing peer learning opportunity to help you navigate the unknown, uncover solutions and accelerate your learning with a small group of trusted peers.

Apply to join a peer group HERE: sfelc.com/peerGroups


  • Why Claire jumped into a brand new industry at Carbon Health (2:31)
  • How Annie transitioned to the autonomous vehicles industry at Waymo (4:41)
  • What inspired Lisa to found tEQuitable after working for the Obama White House (7:38)
  • Annie’s big risk transitioning to search advertising & challenges faced (10:31)
  • Why Claire decided to move from engineering to product management (14:52)
  • Strategies for being bold & combating disrespect in the workplace (20:09)
  • Finding the balance between personal & professional life (22:48)
  • Advice for celebrating your wins (29:27)
  • Audience Q&As: tips for overcoming imposter syndrome (32:40)
  • Evaluate risk with a decision-making matrix (35:38)
  • What happens when you have a bad boss (39:48)
  • Lightning round – Claire, Annie, and Lisa’s best advice for women (42:12)
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