Our Leadership

Chief Executive Leadership Team

Carolyn Childers

Carolyn is Co-Founder and CEO of Chief, leading the company as it builds the largest community of senior women executives. She is also a member of Chief’s Board of Directors. Under Carolyn’s leadership, Chief has grown to be the largest community of senior women executives.

Prior to founding Chief, Carolyn was Senior Vice President of Operations at Handy, then led the launch of Soap.com and acted as GM through its acquisition by Amazon. Prior to Handy, Carolyn held strategy and business development roles at Victoria’s Secret and Avon Products. She began her career in finance, working in investment banking at Deutsche Bank. Carolyn has been named to Inc.’s Female Founders 100 List and Chief has been recognized as one of TIME’s Most Influential Companies and Fast Company’s Most Innovative Companies.

Carolyn holds a Bachelor of Science degree in Finance from Boston College, and an MBA from Harvard Business School.

Lindsay Kaplan

Lindsay is Co-Founder and Chief Brand Officer of Chief, responsible for developing and growing Chief’s brand identity as the largest network of senior women executives, designed to maximize their leadership impact. Lindsay’s oversight has helped elevate Chief’s mission and impact to senior executive women all over the country. She is also a member of Chief’s Board of Directors.

Prior to founding Chief, Lindsay spent the majority of her career leading marketing for high-growth startups, including Casper, which transitioned from a mattress product company to a beloved global sleep brand under her leadership. Lindsay has been named a New York Times DealBook Groundbreaker, one of Business Insider's Most Innovative CMOs in the World, and one of Ad Age’s Leading Women. Chief has been recognized as one of TIME’s Most Influential Companies and Fast Company’s Most Innovative Companies.

Lindsay is a graduate of Brandeis University, where she received a Bachelor of Arts in English and Creative Writing.

Trey Boynton

Trey has dedicated her decades-long career to creating change so that all people are valued, celebrated, and able to offer their unique contribution.

As Chief People & Diversity Officer, Trey leads the People function and the Inclusion & Impact strategy for Chief. Her primary focus is to ensure equity and inclusion is embedded across the entire Chief ecosystem.

Prior to Chief, Trey was Senior Director of Inclusion & Collaboration at Cisco, managing a team dedicated to building and delivering on inclusion promises. While at Cisco, Trey led the company’s first DEI strategy which remains in place today. Prior to Cisco, Trey was the first head of diversity and inclusion for Duo Security. She began her career in higher education, holding multiple diversity & inclusion leadership roles at the University of Michigan, where she worked for more than 20 years. While at the University of Michigan, Trey received the Distinguished Diversity Leaders Award.

Trey holds undergraduate degrees from Georgetown University and Spelman College and a graduate degree from The University of Michigan.

Saana Rapakko Hunt

As Chief Product and Experience Officer, Saana is responsible for the creation and management of all services included in the Chief membership. Her primary focus is to ensure every aspect of the Chief membership responds to what Chief members need as senior business leaders.

Before joining Chief, Saana was President and Chief Product Officer of The Mom Project, a digital employment agency that makes it easy for companies to hire skilled moms. Prior to the Mom Project, Saana held Head of Growth and various product leadership roles at Instagram. She began her career in management consulting at McKinsey & Company where she consulted with a variety of clients on their technology strategy. Saana is also an Angel Investor with The Fund XX, an early stage venture capital fund investing in women-led businesses.

Saana attended Stanford University, where she received a Bachelor of Arts degree in Human Biology and minor in Management Science & Engineering, as well as an MBA from the Stanford University Graduate School of Business.

Bridget Winston

Bridget Winston is the Chief Customer Officer of Chief.

In her role, Bridget oversees the entire customer journey for Chief members, prioritizing a meaningful, human-centric and tailored approach throughout their experience. Prior to joining Chief, Bridget was the Chief Revenue Officer of Shutterstock where she led Sales & Customer Success. Prior to Shutterstock, Bridget held senior leadership roles for a range of technology companies.

Passionate about public service and paving the way for future generations, Bridget serves on the Board of ChildFund International.

Erika Johnson

Erika is the Senior Vice President of Member Experience of Chief, where she leverages over 20 years of experience in both customer-facing industry and consulting roles to enhance Chief’s member journey.

Before joining Chief, Erika led customer experience insights and activation at Kantar, as the firm’s Executive Vice President of North America Customer Experience. Earlier, Erika worked at Ernst & Young, consulting with financial services clients on optimal experience strategies. Erika started her career at Capital One and American Express, leading Enterprise Operations and Membership Rewards teams.

As a servant leader, Erika has enjoyed playing an active role in multiple non-profit organizations, including Board Member for Hip Hop 4 Life, National Advisory Council Member for A Better Chance, and Leadership Board Member for The Council of Urban Professionals.

Erika received a Bachelor of Science in Commerce from the University of Virginia, an MBA from Virginia Commonwealth University, and an ASCENT leadership certification from The Tuck School of Business at Dartmouth.

Chrissy Lo

Chrissy is the Vice President of Finance of Chief. As the company’s first finance leader, Chrissy has held several strategic finance positions at Chief and built the function that she now oversees.

Before joining Chief, Chrissy worked in Investment Banking at Bank of America Merrill Lynch, advising Technology, Media & Telecommunications clients on M&A, IPO, and other debt & equity transactions. Prior to this role, she was a Senior Assurance Associate at PwC and BDO.

Chrissy is a Certified Public Accountant in the state of Washington. She also earned her MBA from Duke University and a Bachelor of Arts degree in Business Economics from UCLA.