Jennifer Morrissey to be Recognized at the 2021 Smart Women Awards, Progressive Woman Honoree, Oct. 7

oswaldcompanies September 15, 2021

CLEVELAND – Sept. 15, 2021 – Jennifer Morrissey, Chief Information Officer of Oswald Companies, has been named a 2021 Smart Women Award honoree in the Progressive Woman category. She will be recognized at the Smart Women Breakfast, Oct. 7, 2021, at the Westin Cleveland Downtown. View the full list of honorees here and watch for the Smart Women Breakfast feature in the October issue of Smart Business Northeast Ohio Magazine.

About Jennifer Morrissey

Morrissey joined Oswald Companies in November of 2016 as Chief Information Officer and became the first person to hold this position within the firm’s 128-year-old history. Prior to Oswald she held information technology leadership positions with one of the world’s largest risk and insurance brokerage firms, applying her global insight and experience to transform Oswald’s IT practice.

As Chief Information Officer of Oswald Companies, one of the nation’s largest privately held insurance brokerage and risk management consulting firms, she cultivates teams across departments and functions, to improve and deliver measurable results, optimize business performance, and foster collaboration for positive, goal-directed transformations.

For nearly two decades Morrissey has served in executive leadership capacities for Fortune 500 companies, leading in both the corporate and expert consultant capacity. Her results-driven approach has enabled large-scale turnarounds, integrations, mergers and acquisitions, and substantial growth strategies for her organizations and its valued clients therein.

In addition to leading the strategic information technology division for Oswald Companies, Morrissey is also a member of Oswald Companies’ Executive Committee, which drives corporate-level decisions and strategic planning on behalf of the business and employee-owner population.

Morrissey’s leadership at Oswald is highlighted by her innovative approach to Technology aimed at realizing value for our clients as insight-driven risk management advisors. She is shaping the future through Technology Modernization, enhancing the Client Digital Experiences, and harnessing the power of Data Analytics.

Women in the insurance industry have historically faced challenges in achieving qualified leadership positions, closing wage gaps, and gaining a voice at the leadership table. From early in her career, Morrissey faced these challenges head-on, quickly advancing into leadership roles, and through her actions and example, serving as both an advocate and mentor to women in her workplaces and throughout her business networks. Morrissey was the first woman to hold a position on Oswald Companies’ Executive Committee. She also serves in the senior advisory and mentorship roles for Oswald’s Women’s Leadership Council.

Currently, Morrissey serves on the Board of Directors for Junior Achievement (JA) of Greater Cleveland, the nation’s largest organization, with 106 local JA areas, dedicated to giving young people the knowledge and skills they need to own their economic success, plan for their futures, and make smart academic and economic choices. She frequently presents at leadership, women’s and trade events, and led Oswald Companies to earn the 2019 Vertafore Champion Award for outstanding achievement automation, advocacy, leadership and service.

Learn more and connect with Jennifer here.

About the Smart Women Breakfast and Awards Program

According to, what started out as the Women in Business conference in 2005, the Smart Women Breakfast addresses issues facing women in the workplace. This morning conference also recognizes the achievements of leading businesswomen, inspiring male advocates and effective women’s programs through the Smart Women Awards program.

The Awards are presented in three distinct categories:

  1. Progressive Woman Award – Recognizes female executives or managers who have risen through the ranks in their career and overcome significant challenges along the way.
  2. Progressive Organization AwardRecognizes organizations that support or promote women based initiatives, develop specific programs that provide opportunities for advancement, or create family-friendly workplaces.
  3. Progressive Entrepreneur Award –  Recognizes female entrepreneurs who have either founded or co-founded a for-profit business that has achieved substantial growth within the last two years due to an innovative product or service.

About Oswald Companies

Founded in 1893, Cleveland-based and employee-owned, Oswald is one of the nation’s largest independent insurance brokerage and risk management firms. As a proud member of Assurex Global, the world’s largest association of privately held insurance brokers, our risk management professionals can service and support the needs of our clients throughout the U.S. and worldwide. Learn more at