Jes Pendergrass is a trusted general counsel and chief compliance officer with more than 20 years of global experience advising companies in highly regulated industries on commercial and strategic transactions, import/export controls, regulatory and environmental compliance, intellectual property, litigation and dispute management, investigations and audits, corporate governance, crisis management, and government affairs.

Jes has negotiated business transactions in dozens of countries, including supply chain, distributor, and supplier contracts; sponsorship, influencer, and other marketing agreements; master service agreements and statements of work; IP licenses; and software (SaaS, enterprise, and OSS) licenses. She brings deep experience across consumer packaged goods (including alcohol beverage), U.S. government contracts, military-aerospace, and ITAR compliance, along with unique experience developing in-house legal teams from the ground up and building enterprise-wide regulatory compliance programs for highly regulated industries.

Before joining Outside GC, Jes served as the first-ever General Counsel and Chief Compliance Officer for Heaven Hill Distilleries, the second-largest holder of aging bourbon whiskey in the world and the fourth-largest distilled spirits supplier by volume in the U.S. In this role, she built the company’s first internal Legal & Compliance department from the ground up, overseeing all legal matters and developing an enterprise-wide compliance program. She also developed and led the company’s government affairs function, implementing political strategies that achieved favorable legislative, trade, and administrative outcomes for Heaven Hill and the distilled spirits industry.

In recognition of her industry leadership, Jes was honored with the Kentucky Distillers’ Association’s Esprit de Corps award for leadership and collaboration within the distilled spirits industry. She is the third woman to chair the KDA in its 140-year history, a role she has held twice. Jes also serves on the board of the American Distilled Spirits Alliance and was the first-ever chair of its General Counsel Committee.

Previously, Jes spent 12 years with Siemens Corporation as Senior Counsel and International Business Partner, advising on regulatory and trade compliance, domestic and international contract transactions, export/import compliance, environmental compliance, intellectual property, data privacy, disputes and litigation, internal auditing, investigations, mergers and acquisitions, and corporate governance. Throughout her career, she has built and led teams across the Americas, EMEA, and APAC.

In addition to her core legal work, Jes has played a key role in shaping broader organizational initiatives. At Heaven Hill, she oversaw the company’s environmental program, led the creation of its first 10-year sustainability plan, and initiated the formation of the Kentucky Distillers’ Association’s first Diversity, Equity and Inclusion Advisory Panel. She also served as executive sponsor for the company’s diversity, equity, and inclusion initiatives and corporate citizenship programs.

Jes has extensive nonprofit and community leadership experience, particularly in environmental sustainability, urban forestry and gardening, food accessibility and healthy eating, and education. She has served as Board Chair and Interim Director of Louisville Grows, President of the Jefferson County Master Gardeners Association, and Trustee of the Board for Bernheim Arboretum and Research Forest.

A Kentucky native, Jes earned her B.A. in photojournalism from the University of Louisville and her J.D. from Lewis & Clark Law School in Portland, Oregon, where she focused on Environmental and International Law. She also holds a Certificate in International & Comparative Law from the University of San Diego School of Law and is a member of the Oregon and Kentucky State Bars.

Jes currently splits her time between Kentucky and Florida. She has traveled to more than 50 countries and all 50 states, and is a bourbon lover, experienced chef, and certified master gardener.