Client Experience

A selection of organizations I’ve supported, along with client feedback from recent engagements.

Rosalynd provided thoughtful advice and steady support on change management as we advanced our People & Culture Target Operating Model. She helped us navigate complexity, anticipate stakeholder dynamics, and approach the work with greater clarity and confidence.
— Nadim Kara, Executive Vice President, Head of People and Culture, GreenShield
GreenShield logo with stylized shield icon and company name in bold lettering.

“Rosalynd Rupert is the perfect person to turn to when you need strategic leadership in communications planning. From employee communications to multi-faceted issue-laden projects, she’s got it covered.”

- Beth Waldman, Director, Strategic Communications & Public Affairs, Peel Regional Police

It was a pleasure to work with Rosalynd. She took a vast, complex internal communications landscape and expertly narrowed our scope to focus on what truly mattered. She listened to our needs, helping to keep us focused. From crafting a comprehensive quantitative survey to conducting insightful focus groups, and analyzing all this data, she provided a final report that was incredibly comprehensive. Rosalynd is professional, thorough and highly strategic. She is an absolute asset to any team.
— Emily Rabe, Director, Marketing and Communications, The Bishop Strachan School
Logo for The Bishop Strachan School featuring a stylized church steeple and cross with water waves below

Impact Stories

Turning Communication Overload into a More Connected Experience

An audit and tailored roadmap designed to strengthen stakeholder communications through practical, audience-informed recommendations.

A large independent school engaged external support to take a fresh look at how its communications channels were serving internal and external audiences. Working closely with the client throughout the process, I co-led a communications audit that combined channel review, stakeholder engagement, and strategic analysis to build a clear picture of what was working well and where there were opportunities to strengthen the overall approach.

The process was grounded in thoughtful listening. Through surveys, focus groups, and review of communications materials and platforms, we developed insights into audience needs, channel effectiveness, and opportunities to improve clarity, consistency, and the overall user experience.

From there, we developed personalized, actionable recommendations across the short, medium, and longer term. Rather than a cookie-cutter plan, the client received a tailored roadmap designed for its specific audiences, their communications environment, and organizational priorities, with practical next steps that could be implemented immediately alongside longer-term opportunities for modernization and improvement.

Outcome: a stronger foundation for more effective communications, including quick wins the client could begin acting on right away, reduced redundancies and resourcing pressures, and a clearer path forward designed to move with the organization into the future.

City of Toronto: Developing a Culture Framework for the Toronto Public Service

A city-wide employee engagement and culture initiative that helped define shared values, align leadership, and embed culture across 40,000 employees.

To help the City of Toronto define and operationalize its corporate culture, I led an employee engagement and internal communications process that centered on input from employees and translated it into a practical culture framework.

The goal was not simply to create a set of values on paper. Working closely with the City Manager and leadership team, I helped design and facilitate an engagement process that gave employees at all levels across the organization an opportunity to contribute their perspectives on what it means to be a member of the Toronto Public Service, what the culture should stand for, and how that culture should show up in day-to-day work. The engagement process was designed not just to gather input, but to build a sense of ownership and connection among employees at every level.

From there, I led the internal communications strategy to introduce the new culture pillars to employees and build organization-wide awareness and understanding. The work did not stop at launch. In parallel, I worked with our HR team to support people leaders in bringing the culture to life through resources and training to equip managers with the tools they needed to model the culture in their day-to-day leadership.

The culture pillars were also embedded across the organization through employee recognition programs, performance management and visual branding, helping to make the culture visible, practical and consistent.

Outcome: a more unified workforce across multiple teams and work locations, stronger alignment between the employee experience and the City’s strategic priorities, and greater support for managers that helped them lead consistently and confidently.

Leadership Brand and Communications Strategy

Partnering with leaders to strengthen their visibility, presence and influence

I have worked with many CEOs, CHROs and other senior leaders to define an authentic personal brand and translate it into a practical communications strategy. Working directly with each leader, I clarify their voice, define key messages and develop a plan for LinkedIn, networking, speaking engagements and other opportunities to build and extend visibility and influence.

This includes developing content themes, content calendars and speech framing that help leaders communicate consistently across platforms while staying true to who they are. The goal is to strengthen their presence without making them sound generic or overly managed, so their communication feels credible, consistent and distinctive.

The results are both immediate and long-term. Leaders typically see stronger engagement with their content, increased LinkedIn followers, more speaking invitations and greater visibility with the audiences that matter most. Over time, they gain confidence in how they show up professionally, become more recognizable to peers and stakeholders, and are often acknowledged by leaders, peers and their teams for the strength and clarity of their communications.

Outcome: a leadership presence that is more visible, more consistent and more influential across digital, networking and professional platforms.