Mary Weimer | Founder, Ready Executive

Mary Weimer is a Certified Executive Coach (CEC), fractional C-suite consultant, and seasoned business leader with nearly 30 years of experience across diverse industries. A lifelong resident of Regina, Saskatchewan, Mary has built a career marked by entrepreneurial success, executive leadership, and a deep commitment to continuous learning and community impact.

Entrepreneurial roots

Mary’s journey began in 1999 when she purchased the Assiniboia Gallery, a renowned art gallery in Regina, where she and her husband Jeremy have continued to grow the business for over 25 years. This entrepreneurial venture sparked her passion for helping other business owners scale and navigate growth.

Managing growth and expansion

In 2013, seeking broader leadership challenges, Mary transitioned from running the gallery day-to-day to becoming the Chief Operating Officer at Hillberg & Berk, a fast-growing jewelry company. Over five years, she played a pivotal role in the company’s rapid expansion from a single location to eight, gaining invaluable experience in shaping operations, driving culture, and aligning business strategy with a founder’s vision.

Cultivating a solid leadership philosophy

Mary continued her executive journey at Conexus Credit Union, where she held senior roles as Chief Member Experience Officer and Chief Advice Officer. During her time at Conexus, she led diverse portfolios, including Marketing, Community Investment, Cultivator (technology incubator), Retail and Business Banking, and Wealth Management. Mary’s leadership philosophy at Conexus was rooted in trust and autonomy, fostering a culture of continuous leadership development and alignment with the organization’s purpose and values.

Shaping legacies

Most recently, Mary served as Chief Operating Officer at Harvard Developments, part of The Hill Companies, where she oversaw Property Management, IT, Legal, Marketing, and Human Resources for the Canadian real estate division. Her time at Harvard reinforced the importance of community building and creating a lasting legacy within family-owned businesses.

Throughout her career, Mary has consistently prioritized relationship-building, customer-centric service, and creating meaningful impact across every organization she’s been a part of. Whether in the art world, jewelry industry, financial services, or real estate, Mary’s approach is grounded in fostering collaboration, developing high-performing teams, and leading organizations through change.

Family and community

Mary is also a dedicated volunteer and board member, currently serving as a director for Cowessess Ventures Ltd. (CVL), the economic development arm of Cowessess First Nation, and as a member of the Regina Food Bank’s Capital Campaign Committee. Her past board roles include SaskArt, Globe Theatre, Youth Ballet of Saskatchewan, and the Saskatchewan Chamber of Commerce.

Outside of her professional life, Mary is married to Jeremy and together they have four children. Together, they enjoy an active family life filled with sports, music, and creative pursuits. Mary’s commitment to her family, her community, and her professional growth is the foundation of her work and approach as a Fractional Executive and Executive Coach.