Jennifer Mackay

Jen J. MacKay is an accomplished insurance executive and transformation leader with more than 15 years of experience guiding underwriting organizations through periods of significant growth, modernization, and strategic change. She currently serves as Senior Director of Digital Transformation at H.W. Kaufman, a role she has held since 2021. In this capacity, she leads enterprise‑wide initiatives that leverage technology, data, and process optimization to strengthen operational efficiency and accelerate innovation across the organization.

Before joining Kaufman, Jen spent two years in London as Head of North American Property for Globe Underwriting, where she oversaw portfolio strategy, underwriting performance, and expansion across the North American market from 2019 to 2021.

Prior to her international leadership role, Jen served as President of WSG Specialty Underwriting in Houston, Texas, from 2010 to 2019. During her tenure, she guided the company through key phases of market development, organizational restructuring, and specialty product growth—establishing WSG as a competitive force within its segment.

Outside of work, Jen enjoys a vibrant and hands‑on life. She is the proud parent of three grown children and the doting grandparent of three grandchildren. At home, she shares her days with one loyal dog and a lively flock of seven chickens. Her free time is spent renovating her historic farmhouse—one project at a time—and exploring her creative side as an amateur artist.