12 High-Powered Operators You Need on Your Board

As business challenges grow more complex, the need for fresh perspectives and varied expertise has never been more critical in the boardroom. Research consistently shows that gender-diverse boards correlate with stronger financial performance, improved decision-making, and enhanced corporate reputation, but some reports show the needle is moving in the wrong direction. Here are 12 powerhouse operators who can drive innovation, enhance risk management, and foster sustainable growth in the boardroom and beyond.

From technical leaders to finance chiefs to GTM champions, each one brings a potent mix of expertise, vision, and proven leadership - exactly what companies today need to stay ahead of the curve.?

Anneka Gupta

Chief Product Officer, Rubrik ?

Fresh off a hot IPO, Anneka brings more than a decade of product and SaaS expertise with a track record of driving revenue growth, navigating expansions to new markets, and overseeing diversity, inclusion, and belonging initiatives. She joined Rubrik from LiveRamp where she was the President and Head of Product and Platforms leading product development and go-to-market operations and strategy. Anneka also sits on the board of directors for Tinuiti.

Billie Sue Chafins

Chief Technology Officer, Tripadvisor

Billie Sue has spent 25+ years shipping world-class consumer and enterprise software for large consumer technology companies, with over 15 years of experience leading teams. Before joining Tripadvisor earlier this year, Billie Sue was Head of Engineering at Level. Prior to that, she was SVP of Software Engineering at Disney Streaming, where she led Web engineering for Hulu, Disney+, ESPN+, and Star+; Identity Access and Management for The Walt Disney Company; and Viewer Experience tooling. She managed a team of nearly 300 developers across Seattle, Santa Monica, New York, Amsterdam, London, and Beijing and was the site lead of Hulu’s Seattle office. Prior to Disney Streaming and Hulu, Billie Sue spent 14 years at Microsoft.

Deborah Holstein

Chief Growth Officer, Rocket Lawyer

Deborah has over 15 years in marketing leadership roles in SaaS businesses (B2C, B2B and B2B2C). She’s currently the Chief Growth Officer at Rocket Lawyer. Previously, she led the marketing function at Dropbox, where she was responsible for driving profitable, full funnel growth for all Dropbox products. She has held marketing leadership roles at Betterworks, Cisco and Yahoo as well as launching and growing technology startups including Hightail and Grokker. Skilled in building and leading highly engaged teams, Deborah is an active leadership mentor with Torch.io and regularly publishes articles on marketing and leadership topics.? She holds an MBA from New York University in Marketing and Statistics and a BS in Business Administration from Georgetown University.

Erica Dorfman

EVP, Global Financial Products, Brex

Erica is the head of global financial products, where she manages teams responsible for building Brex's core financial services functionality and Brex's global expansion strategy. She has previously held executive finance roles including CFO for Tally Technologies and Head of Capital Markets for SoFi. She is an active angel investor and advisor in fintech and B2B software (including: Silo, Evergrow, Anchorage Digital, Mundi, Causal, Cardless, Vartana).

Francessca Vasquez

Global Vice President, Amazon Web Services (AWS) Professional Services and GenAI Innovation Center

Francessca is VP, Technology and Customer Solutions at Amazon Web Services (AWS). She oversees the sales and delivery P&L of AWS consulting services, consulting offerings, and management of customer engagements across the worldwide public sector, commercial, industries, and partner business. Francessca also serves as the Executive Sponsor for the AWS Global CIO Council and is a co-founder of AWS’ Workforce Transformation STEM and customer initiatives fostering untapped talent development and representation in tech equity. Prior to AWS, Francessca spent 11 years with Oracle, most recently as the Group Vice President of the North America Cloud Infrastructure team. She has held numerous leadership roles in consulting, business development, and business-technology architecture strategy with Salesforce, CSC (now DXC) Sun Microsystems, and the U.S. Department of Defense (DoD).

Jeanne DeWitt Grosser

Chief Business Officer, Stripe

Jeanne has been with Stripe for more than 8 years, and has helped build out Stripe’s Sales org from the ground up, driving go-to-market strategy and many of the specialized functions required to support complex customers. She is also a board member of Upside, a technology company that increases the financial power of people and businesses. Prior to Stripe, Jeanne was the Chief Revenue Officer of Dialpad, where she ran all go-to-market functions and drove 4x year-over-year revenue growth. She was also a Director of SMB and Mid-Market Sales at Google, where she led new business acquisition, account management, direct and channel sales for Google Workplace in North America, LatAm, and APAC.?

Jessica Rusin

Senior Advisor, Executive Coach, Fractional CTO

Jessica is an experienced technology executive, startup investor and advisor. She currently advises and offers fractional CTO consulting and executive & leadership coaching. Most recently she was CTO of OpCo PortCo Guild , a high-growth startup valued at over $4B, providing a platform for workers at America’s largest employers to access debt-free education programs. Jessica joined Guild in early 2016 as the second employee and successfully grew and managed the technology organization from one employee to over 225 employees. Prior to joining Guild, she was the Senior Director of Engineering at MobileDay, a venture-backed startup providing one-touch conference and international dialing solutions. Jessica has 20 years of technology experience and in addition to co-founding and leading at startups, she has led software engineering teams at Digital River, Inc., an e-commerce company, and two large telecom companies, Level 3 Communications and Time Warner Telecom, where she focused on scaling enterprise systems. Jessica graduated with honors from the University of Minnesota, with a B.A. in Computer Science and a minor in Mathematics.

Kristy Friedrichs (McBride)

Chief Partnerships Officer, Palo Alto Networks

Kristy is Palo Alto Networks Chief Partnership Officer, where she is responsible for bringing the platform to market alongside and through an ecosystem of value-added partners, strategic advisers, service providers, technical partners and distributors. Prior to Palo Alto Networks, Kristy was COO of New Relic, where she oversaw? corporate operations, business systems and applications, data analytics and engineering, sales strategy and operations and product operations. Before COO, she was the Chief People Officer. She is passionate about what she calls ‘turning strategy into reality’: aligning the company around an inspiring vision, mission and strategy; establishing goals and clear priorities toward achieving that strategy; and enabling cross-functional execution against those goals. Prior to New Relic, she spent more than 15 years at Bain & Company, first as a consulting principal and most recently as the head of consulting operations for the Bay Area.

Li Fan

Chief Technology Officer, Circle

One of Forbes’ America’s Top 50 Women in Tech, Li? is CTO of global fintech firm Circle. She was formerly CTO and interim CPO at electric scooter company Lime. Before Lime, Li was SVP of engineering at Pinterest, where she launched computer vision and recommendations. She was also? Senior Director of Engineering at Google overseeing image search., and Vice President of Engineering at Baidu, China.?

Shannon Nash, Esq., CPA

Chief Financial Officer, Wing

Shannon is CFO at Wing, a drone delivery company and subsidiary of Alphabet, Inc, who oversees all corporate finance, strategy, accounting, investor relations, fundraising, and regional/partner operations. Shannon is a financial expert, attorney, and CPA with over 25 years of experience helping scale companies through strong financial and operational leadership.? She serves on the Board and Audit Committee of NetScout Systems Inc. (NASDAQ: NTCT), and is also a Board Member and Audit Chair at Lazy Dog Restaurants, one of the fastest growing restaurant companies with 41 locations in 8 states. Additionally, Shannon is on the Board of SoFi Bank, a subsidiary of SoFi Technologies Inc. (NASDAQ: SOFI).? She formerly served as the Lead Independent Director, Chair of the Nominating & Governance Committee, and member of the Audit Committee at UserTesting (NYSE: USER) until the company was acquired by Thoma Bravo in January 2023. She’s also an award-winning documentary film producer with her film, Colored My Mind, winning best short at the 2013 American Pavilion in Cannes. Her latest film is OnBoard, a brilliant chronicle of the rise of Black women on America's boards and the evolution of board diversity from Patricia Roberts Harris in 1971 to the present day, as seen through the eyes of a group of fearless women organized during the Summer of 2020 to create change.

Tiffany To

SVP/GM Enterprise and Platform, Atlassian

Tiffany is an accomplished product executive with over 15 years of experience leading high-performing product teams. She is currently the SVP/General Manager of Enterprise and Platform of Atlassian, a leading provider of collaboration and productivity software. Prior to Atlassian, she served as product and marketing leads at companies such as Intel, VMware, Cohesity, Nutanix, and more. On top of her daily role, Tiffany regularly advises and invests in early stage startup companies.

Yolanda (Yolis) Ruiz

Vice President, Finance, Grindr

Yolis is VP of Financial Planning and Investor Relations at Grindr. Yolis has spent her career in finance and operations roles and has had the opportunity to be part of the IPO journey of multiple companies. Prior to Grindr, she held finance roles at various organizations including Coursera, Eventbrite, and Gap, 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.