Chief Operating Officer

About Hollyhock

Hollyhock is an internationally known center for transformative learning and leadership, located on the wild and scenic Cortes Island within the traditional territories of the Klahoose, Tla'amin, and Homalco Nations. For over four decades, it has brought together leaders, change-makers, artists, activists, and seekers for the inner and outer work that real transformation demands. The organization delivers more than 100 programs every year across Cortes Island, Vancouver, and online. Its culture is grounded in relationships and is guided by openness, equity, and authentic collaboration in practice.

Hollyhock is entering a pivotal new phase. In 2024, it launched a strategic plan for the coming decade, and a new CEO has arrived with a clear sense of direction and deep experience in leadership education. The organization’s next chapter includes building a living learning center focused on regenerative leadership, strengthening ties with the Cortes and nearby First Nations communities, developing a distinctive Hollyhock curriculum, expanding through hybrid and digital offerings, and creating a financially durable operating model. The key priority now is execution, and this role is central to delivering it.

The Opportunity

As Chief Operating Officer, you will serve as the CEO’s financial and strategic partner during the execution stage of Hollyhock’s next decade. You will be part of the senior leadership team and will bring strong commercial and financial discipline while also helping drive revenue growth and innovation, alongside an already established operations, program, and development structure.

With major strategic priorities ahead, including a significant program redesign and a campus-wide revitalization project, you will provide senior-level financial leadership through a period of substantial change. You will help the organization refine its business model, identify new routes for earned and philanthropic revenue, and convert the strategic plan into clear milestones and measurable results. You will also support the team in reviewing and improving systems across the organization.

This position is ideal for a seasoned business leader who combines strong people skills with confidence at the intersection of finance, operations, team leadership, and mission alignment. The right person will bring clarity to decisions rather than unnecessary complexity. As the organization’s second-in-command, the COO will free the CEO to concentrate on vision, strategy, partnerships, and philanthropy while ensuring operational excellence, cultural strength, and long-term financial resilience.

Hollyhock’s future direction is ambitious. This role requires the structured planning, financial rigor, and systems mindset needed to turn that ambition into action. A strong first year would include a revenue model that is steadily moving toward operational self-sufficiency, a dependable finance and budgeting cadence, an annual planning structure that is tightly linked to strategy, and a leadership team operating with greater consistency and alignment. The mandate is to strengthen what already exists and introduce the structure and innovation needed for the next stage.

Location and Work Arrangement

This is a remote role for candidates based in Vancouver or Vancouver Island, with approximately 8 to 12 weeks per year spent on Cortes Island.

What You Will Bring

• Background in senior leadership within mission-driven, hospitality, education, retreat, professional services, or values-based commercial settings.
• Proven ability to create operating systems and financial discipline in a small to mid-sized organization, especially where you have built the structure yourself.
• Strong financial capability, including budgeting, forecasting, and performance analysis. A CPA or similar finance designation, or an MBA, would be an advantage.
• Experience with fundraising, non-profit environments, and generating philanthropic revenue is a significant plus.
• Strong emotional maturity and self-management, with the ability to handle complexity without making it more complicated, stay composed under pressure, and work well with people without avoiding conflict.
• A commitment to equity, cultural humility, and workplace practices that reflect the diversity of the communities served.
• Comfort working in a lean, values-driven organization where systems may be uneven, the work is meaningful, and you enjoy bringing structure and order.

Compensation and Benefits

The salary range is CAD 100,000 to CAD 125,000, depending on experience.

The benefits package includes health and dental coverage, vacation, statutory holidays, wellness days, and an employee assistance program. Team members also receive one complimentary Hollyhock course each season, plus 50% off additional tuition. Additional discounts are available at the Hollyhock Store, Bodywork Studio, accommodations, and meals. On campus, the package includes complimentary breakfast, a daily movement class, access to the spa, trails and gardens, and presenter evenings.

Additional Notes

Hollyhock thanks all applicants for their interest. Because of the expected volume of applications, only candidates selected for the next stage will be contacted.