Mary Weimer | Founder, Ready Executive

I work with senior leaders, boards, and organizations to strengthen leadership by addressing the systems around it — including decision-making, governance, structure, and execution.

My approach is grounded in lived experience. Over nearly 30 years, I’ve worked inside organizations as an entrepreneur, executive, board member, and advisor. Across industries and stages, I’ve seen firsthand how leadership succeeds and struggles when systems evolve more slowly than expectations.

Entrepreneurial roots

My career began in 1999 when I purchased Assiniboia Gallery, a well-established art gallery in Regina, Saskatchewan. For more than 25 years, my husband Jeremy and I have grown the business while navigating the realities of founder-led decision-making, creative vision, operational discipline, and sustainability.

This experience shapes how I work with entrepreneurs and small business leaders today. I understand the weight founders carry and the importance of building leadership and operational systems that allow a business to grow without losing what makes it distinctive.

Scaling and executive leadership

In 2013, I stepped into a Chief Operating Officer role at Hillberg & Berk, a fast-growing jewelry company. Over five years, I supported the organization’s expansion from a single location to eight, helping translate a founder’s vision into operational structure, leadership rhythms, and execution.

This period reinforced a pattern I’ve seen repeatedly: growth succeeds when leadership systems such as roles, decision-making, accountability, and culture evolve in step with ambition.

Leadership in regulated and governance-heavy environments

I later held senior executive roles at Conexus Credit Union, including Chief Member Experience Officer and Chief Advice Officer, with responsibility for diverse portfolios spanning retail and business banking, wealth management, marketing, community investment, and a technology incubator.

Working within a regulated environment deepened my understanding of governance, accountability, and stakeholder responsibility. It also strengthened my leadership philosophy which is rooted in trust, autonomy, and clear decision-making along with my comfort operating at the board–executive interface.

Most recently, as Chief Operating Officer at Harvard Developments (The Hill Companies), I oversaw Property Management, IT, Legal, Marketing, and Human Resources for the Canadian real estate division. This role reinforced the importance of long-term thinking, leadership continuity, and legacy within private family-owned enterprises.

How this experience shapes my work today

Across every role, a consistent theme has emerged:
strong leadership depends on systems that support it.

My work now focuses on helping organizations:

• clarify leadership roles and decision-making

• strengthen governance and accountability

• reduce over-reliance on individual leaders

• create leadership structures that are effective and sustainable

I do this through Leadership Systems Advisory, Fractional COO engagements, and context-aware Executive Coaching, depending on what the organization needs most.

Community and governance

I am an active volunteer and board member, currently serving as a director with Cowessess Ventures Ltd., the economic development arm of Cowessess First Nation. Past board roles include SaskArt, Globe Theatre, Youth Ballet of Saskatchewan, Saskatchewan Chamber of Commerce and the Regina Food Bank Capital Campaign Committee.

This governance experience informs my advisory work and reinforces the importance of stewardship, accountability, and leadership beyond day-to-day operations.

Outside of work

I live in Regina with my husband Jeremy and our four children. Family, community, and creative pursuits are central to my life and shape my perspective on leadership, sustainability, and impact.