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Bill Bailey's work experience includes:

- Senior Vice President Talent & Learning at Sompo International, where they are responsible for property and casualty insurance and reinsurance. (2022 - Present)

- Senior Director Global HR Consulting & People Solutions at UKG, where they focused on optimizing HR service delivery and expanding the digital experience for employees. (2021-2022)

- Vice President Human Resources at The Hanover Insurance Group, where they served as the senior HR business partner for specialty insurance and HR operations support. (2017-2021)

- Vice President Talent Management at Staples, where they provided strategic leadership for talent management and oversaw 90 employees across multiple regions. (2016-2017)

- Vice President Human Resources at Staples, where they led the HR Business Partner team and supported various departments. (2014-2016)

- Human Resources Director at Staples, where they served as the senior HR business partner and provided strategic and tactical leadership. (2011-2014)

- Held various roles including Director of Human Resources at Staples from 1996 to 2011.

- Manager Human Resources Business Process at EMC Corporation. (2000-2001)

- Program Manager Associate Communications, Recognition & Development at MassMutual Financial Group. (1994-1996)

Bill Bailey holds a Master of Science (M.S.) degree in Industrial/Organizational Psychology from Springfield College. Bill also has a Bachelor of Science (B.S.) degree in Psychology with a minor in Business Management from the same institution. Furthermore, they have obtained additional certifications in Strategic Workforce Planning from the Human Capital Institute and Everything DiSC Certification from Everything DiSC: A Wiley Brand, both in 2023.