Overview
Chief Operating Officer Jobs in Vancouver, British Columbia, Canada at BoldHouse Executive Search
About Hollyhock
Hollyhock is a globally recognized transformative learning and leadership center on wild and beautiful Cortes Island, the traditional territories of the Klahoose, Tla'amin, and Homalco Nations. For more than 40 years, Hollyhock has convened leaders, changemakers, artists, activists, and seekers to do the inner and outer work that transformative change requires. More than 100 programs run each year, on Cortes, in Vancouver, and online. Hollyhock's culture is built on relationships, values openness, equity, and genuine collaboration, and holds those values in practice.
Hollyhock is at an exciting moment. A strategic plan for the next decade launched in 2024. A new CEO brings strong vision and directional clarity, with deep roots in leadership education and a clear picture of where the organization is going: a living practice centre for regenerative leadership, deepened relationships with the Cortes and local First Nations communities, a signature Hollyhock curriculum, hybrid and digital programs that extend the campus globally, and a financially durable model. The question now is execution, and this hire is central to it.
The Role
As Chief Operating Officer, you will be the CEO's financial and strategic partner as Hollyhock moves into the execution phase of its next decade. You will sit on the senior leadership team. Your contribution is to bring senior business and financial discipline and to drive revenue generation and innovation for an organization with strong operational, programmatic, and development leadership already in place.
With major strategic priorities on the horizon, including the implementation of a significant programmatic shift and a campus-wide revitalization project, you will provide senior financial leadership for the organization through a time of significant change. You will help guide the team in updating the business model and identifying innovative pathways for generating both earned and fundraised revenue. You will help translate the strategic plan into clear milestones and measurable outcomes, and support the team in assessing and optimizing systems throughout the organization.
This role is well suited to a senior business leader with strong people skills who is comfortable operating at the intersection of finance, operations, team leadership and mission alignment, and who brings clarity rather than complexity to decision-making. As the organization’s second-in-command, the COO will enable the CEO to focus on vision, strategy, partnerships, and philanthropy, while ensuring the organization is operationally exceptional, culturally strong, and financially durable.
The vision for Hollyhock’s evolution at this moment is ambitious. This role brings the structured planning, financial discipline, and systems thinking to operationalize it. Success in year one looks like a revenue model that is increasingly moving toward operational sufficiency, a finance and budgeting rhythm the organization can rely on, a planning structure that connects the strategic plan to annual priorities, and a leadership team operating with greater clarity and coherence. The work is to bring senior discipline to what exists and add the structure and innovation required for the next phase.
This position is remote within Vancouver or Vancouver Island, with approximately 8-12 weeks per year on Cortes Island.
What You Will Bring
- Senior leadership experience in mission-driven, hospitality, education, retreat, professional services, or values-led commercial environments.
- Demonstrated success building operating systems and financial discipline in a small to mid-sized organization. You have built rather than inherited.
- Strong financial fluency, including forecasting, budgeting, and performance analysis. A finance designation (CPA or equivalent) or MBA is a plus.
- Experience with fundraising, non-profits, and bringing in philanthropic sources of revenue is a major asset.
- Maturity and emotional self-management. You hold complexity without overcomplicating, are calm under pressure, and are good with people without being conflict-averse.
- A commitment to equity, cultural humility, and building working environments that reflect the diversity of the communities they serve.
- Comfort in a lean, values-led environment where infrastructure is uneven, the work is meaningful, and the right person finds energy in bringing order.
Compensation
$100,000 – $125,000 CAD, based on experience
Comprehensive package including health and dental, vacation, statutory holidays, wellness days, and employee assistance program. One complimentary Hollyhock course per season plus 50% off additional tuition. Discounts at the Hollyhock Store, Bodywork Studio, accommodations, and meals. On campus: complimentary breakfast, daily movement class, spa, trails, gardens, and presenter evenings.
Thank you to everyone who applies. Given the response we expect, we will only be able to contact those moving forward to the next stage.
Title: Chief Operating Officer
Company: BoldHouse Executive Search
Location: Vancouver, British Columbia, Canada