Collective Spotlight

Hispanic Heritage Month: Celebrating the OpCo Community

Caroline Caswell

To celebrate Hispanic Heritage Month, we’re highlighting some of the most successful, respected executives in the tech industry who identify as being of Spanish, Mexican, Caribbean, Central American, and/or South American descent. Get to know (and follow!) these exceptional Operator LPs, investors, and portfolio founders and CEOs:

Elena Gomez

Chief Financial Officer, Toast. Board Member of PagerDuty, SmartSheet, the Haas School of Business and OpCo Advisory Board.

While most people go to restaurants to simply eat the food, Elena Gomez spends just as much time observing the operational flow from order to execution, giving her a leading advantage in her latest role of Chief Financial Officer of Toast, Inc., a cloud-based, end-to-end technology platform purpose-built for the entire restaurant industry. Elena is responsible for Toast’s finance organization and leads the company’s accounting, treasury, financial and strategy, and business operations. With over 30 years of experience ranging from scaling SaaS businesses into multi-billion organizations, building and leading large-scale operational teams, and achieving executive alignment on strategy and financial goals across multiple stakeholders, Elena has no shortage of proven outcomes. Most recently she helped scale Zendesk to over $1B in annual revenue while serving as CFO. While her accomplishments seem like they couldn’t get any bigger, she recently added one more title to her CV: 5th grade basketball coach to her daughter’s team.  

Elena currently serves as a member of the Board of Directors at Smartsheet and PagerDuty. She also serves on the board of the Haas School of Business and The Boys and Girls Club of San Francisco. She holds a BS in Accounting from the University of California, Berkeley.


Maia Josebachvili

Head of Strategic Operations, Financial Services, Stripe. Board Member of Brightwheel, Dartmouth Magnuson Center. Board observer at Forma, TrueLayer.

Maia Josebachvili is currently a member of the Leadership Team at Stripe, transitioning from Head of Strategic Operations, Head of Corporate Development, and Head of People at the company. Prior to her current run at Stripe, she served as Vice President of Strategy, Marketing, and People at Greenhouse, a recruiting and automation platform. While Maia’s talents seem endless, she's also had stints as a Founder & CEO (sold the company), a derivatives trader on Wall Street, an engineer, and a pro-skydiver logging over 750 skydives. Throughout these experiences, she's been a part of the growth journey of scaling several companies from 1 to 8000+ employees. Maia is on the board of Brightwheel and the Dartmouth Magnuson Center, and is a board observer at Forma and TrueLayer.

Outside of work, you can find her trail running, camping with her husband and two young sons, living the part-time van-life, and working towards a life of full-time adventure. Maia holds a BS in Mechanical Engineering from Dartmouth College and an MBA from Stanford Business School.


Manny Medina

CEO, Outreach.

Manny Medina is the CEO of Outreach, a sales platform he co-founded in 2014. Prior to Outreach, Manny was employee number three on Amazon’s AWS team where he engineered Amazon’s compensation system for Amazon Associates, and led the Microsoft mobile division from launch to $50M in annual revenue. He holds an MBA from Harvard and a Masters in Computer Science from the University of Pennsylvania. 

Known for his vulnerable and transparent leadership, Manny sends heartfelt weekly emails to his employees, hosts Friday get-togethers, and encourages everyone to recognize the highs and lows of their job and workplace. Manny grew up in Ecuador and now lives with his wife and three children in Seattle.


Olivia Nottebohm

COO, Dropbox (Former). Board Member, AppFolio, Lightmatter. Advisor, Arcadia.

As the COO of Dropbox, Olivia was responsible for the company's business functions - Sales, Marketing, Customer Success, Support, Partnerships, Strategy & Operations, Communications and People. Olivia has over 20+ years experience making decisions, driving results and growing tech companies. She was responsible for growing the Google Cloud SMB business from $400M to $2.4B from 2016 to 2020 (bringing it to profitability and maintaining a profit margin uniquely across the Google Cloud platform). Olivia then went on to grow Dropbox revenues profitably - delivering its first 3 subsequent quarters of profitable growth while delivering the 15% growth she committed to the Street at the start of 2020. Olivia then built out the Go-to-Market functions of Notion (Sequoia-backed start-up valued at $10B), profitably growing revenue 125% year-over-year.

She holds a BA in Economics from Harvard University and an MBA from Stanford Business School.


Christina Calvaneso Ross 

Co-Founder and CEO, Cube.

Christina Ross is the Founder and CEO of Cube, a real-time FP&A platform for modern finance teams. With prior roles at Rent the Runway, Criteo, Eyeview, and GE, Christina has over two decades of finance experience that she’s now leveraging for her latest startup. As a venture-backed CFO and in roles prior, Christina is committed to ensuring company diversity exists at the start, enabling the greatest possible experiences and outcomes for employees and users alike.

Christina holds a BBA in Operations Management from the University of Massachusetts Amherst.


Yolis Ruiz 

VP of Financial Planning and Analysis, Coursera.

With more than 20 years of experience and leadership positions in high growth companies ranging from pre-revenue to post IPO, Yolis has spent her career in finance and operations roles. Prior to Coursera, she held finance positions at various organizations including Eventbrite, Gladly, and Gap Inc and has a unique blend of experience in marketplace, consumer, and enterprise software businesses. Earlier in her career, she served as an investment Partner at Pacific Community Ventures, and also served as a consultant for The Boston Consulting Group.

She holds a BS in Industrial Engineering from Tecnológico de Monterrey and an MBA from Stanford Business School.

Lolita Taub

GP, Ganas Ventures.

As a Latina emerging manager and general partner at Ganas Ventures, Lolita enjoys working with or investing in community-driven founders, funders, and friends. She has a strong track record with 15 years of experience in the Silicon Valley ecosystem. She has sold over $70 million in tech products and services, made over 90 investments as an angel investor and venture capitalist with Backstage Capital, Lightspeed, and The Community Fund, and had three successful exits from her portfolio. She has been acknowledged by Forbes, Inc Magazine, Nasdaq, and others for her efforts in advocating investment in founders who are underestimated and undervalued.

She holds a BA in International Relations from the University of Southern California and an MBA from the IE Business School.

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