Vanilla Appoints Jim Sinai as Chief Marketing Officer and Karen Nachbar as General Counsel


Jim Sinai, Marketing Director

Portrait of new General Counsel Karen Nachbar

Karen Nachbar, General Counsel

Vanilla announces the addition of key executives following a $30 million Series B investment to accelerate Vanilla’s growth.

Our mission is to empower everyone to create a meaningful legacy. Jim and Karen join us at an important time.

— Gene Farrell, CEO

UNITED STATES, Aug. 4, 2022 / — Vanilla, the award-winning real estate advisory platform designed to transform the way wealth advisors help their clients manage their estates and build their legacies, announces the arrival of Jim Sinai as Chief Marketing Officer and Karen Nachbar as General Counsel. Jim and Karen join following a $30 million Series B investment led by Insight Partners to complement a leadership team announced earlier this year and accelerate Vanilla’s growth.

As CMO, Sinai will lead the marketing function and report to Gene Farrell, CEO. Jim brings to Vanilla his extensive experience in introducing new software products, launching brands, creating demand and growing marketing teams.

As General Counsel, Nachbar is responsible for Vanilla’s legal, compliance and risk matters, and also reports to CEO Gene Farrell. She acts as a strategic advisor to the management team and the board of directors and is responsible for providing advice on corporate strategy, ethics and compliance, privacy and data governance.

“Jim and Karen are joining us at an important time. Our mission is to empower everyone to create a meaningful legacy. said Gene Farrell, CEO. “Our platform helps advisors build deeper relationships with their clients by helping them integrate their estate plan with their financial situation to maximize the impact on the people and causes they care about. Adding Jim and Karen will help us scale faster and continue to raise the bar on security, privacy and compliance. »

“We created Vanilla to simplify estate planning for advisors and their clients. With Vanilla, advisors and clients work together on a collaborative platform to minimize their tax burden and maximize their inheritance,” said Vanilla President, Founder and Wealth Advisor Steve Lockshin. “We are thrilled to welcome Jim and Karen to our growing team.”

With over a decade of enterprise software marketing experience, Sinai joins Vanilla after nearly 3 years as Senior Vice President of Marketing at Procore Technologies, a construction software company. At Procore, he led global marketing where he helped the company grow from $200 million to nearly $500 million in revenue, including a successful IPO in 2021. Prior to Procore, Jim held various marketing leadership positions at Salesforce in various business units, including Salesforce Einstein, Salesforce Platform, AppExchange,, and Salesforce Industries. Jim holds a BA from Brown University and an MBA from Stanford Graduate School of Business.

Nachbar brings 25 years of experience providing legal advice to technology companies across all industries. She previously served as general counsel for Bark, Inc., where she oversaw the company’s legal affairs. From 2017 to 2019, Karen served as Senior Vice President, Associate General Counsel and Compliance Counsel at Sotheby’s, where she supported all aspects of technology, data and privacy for the house of world fine art auction. She has also held legal positions at Scholastic, Houghton Mifflin Harcourt and Morgan Stanley. Karen holds a JD with honors from George Washington Law School and a BS from Cornell University.

About Vanilla

Vanilla is the real estate advisory platform, purpose-built to empower financial advisors to build deeper relationships with their clients and empower them to build and protect their legacies. From robust, easy-to-understand visualizations of complex estates, to detailed diagrams of how assets are transferred to future generations, to ongoing estate tracking, Vanilla is reinventing the estate planning experience, end-to-end. Learn more about vanilla at

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