Director of Leadership and Learning Programming

Director of Leadership and Learning Programming

About Hollyhock

Hollyhock is a globally recognized transformative learning and leadership center located 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 actually requires. More than 100 programs run each year, on Cortes, in Vancouver, and online. The community that has grown up around Hollyhock is one of the most distinctive in the social change world.

Hollyhock's culture is built on relationships. Staff consistently describe their working relationships as one of the best things about being here. It is a place that values openness, equity, and genuine collaboration - and holds those values in practice. The work is serious and the culture is alive - there is genuine joy in how people show up here, and in what they are building together.

Hollyhock is at an exciting moment. A strategic plan for the next decade launched in 2024. Its new CEO brings deep roots in leadership education and a clear vision: Hollyhock as a living practice centre for regenerative leadership - including deepened relationships with the Cortes and local First Nations communities, a signature Hollyhock curriculum, hybrid, digital and cohort-based programs that extend the campus globally, and a financially durable program model. The question now is execution - and this hire is central to it.

The Role

As Director of Leadership and Learning Programming, you will lead the full program portfolio at Hollyhock - overseeing the presenter-led programs team, providing direction for the Hollyhock Leadership Institute, and guiding the development of the next generation of programming alongside the CEO. This role sits on the senior leadership team.

The immediate work is grounded and operational. You will step in as the director-level program portfolio lead, provide visionary leadership to the Hollyhock Leadership Institute portfolio, and get a prototype version of a Hollyhock online learning platform and digital community up and running by the end of 2026.

The longer-horizon work involves building Hollyhock's next chapter. Working with the CEO, you will help design and orchestrate the transition from the current presenter-led program model to a living leadership practice center. You will build and guide a team that collectively develops Hollyhock's signature leadership curriculum - with clear pathways from introductory to immersive and hybrid courses, and into ongoing digital community. You will own the revenue performance of the program portfolio and be responsible for ongoing program evaluation and performance metrics.

A central part of this role is strengthening Hollyhock's programmatic revenue model. You will develop and refine pricing strategies and program mix to optimize both impact and financial return, partner with Marketing to drive enrollment and conversion, and collaborate with Development to align programming with funder priorities and philanthropic strategy. As a nonprofit that relies on a mix of earned revenue and philanthropy, this role plays a critical

part in ensuring that programming contributes meaningfully to organizational sustainability while expanding reach.

A typical week moves between program team support, strategic conversations with the CEO and senior leadership team, presenter and partner development, budget tracking, and curriculum design work - with the occasional week working on Cortes Island with views of the water. This role is primarily remote, with meaningful time on-campus each year.

The person who succeeds here earns the trust of a tenured team, holds what exists while building something new alongside it, and finds real satisfaction in translating a compelling vision into rigorous program work. Success in year one means a team with clear direction, a 2027 Hollyhock Leadership Institute calendar that reflects your creative input, an online community platform that is live, and a clear roadmap for the development of Hollyhock's signature leadership curriculum.

This is not a purely build role, but it is far from a maintenance one. The existing programme calendar runs two years ahead, the team has deep tenure, and the first 12-18 months will require earning trust while managing a large and active operation. At the same time, the leadership curriculum and online platform are genuinely new builds - there is real creative and strategic room here for someone with initiating energy. The three-year opportunity is significant. The first-year reality holds both.

What You Will Bring

• Demonstrated expertise in adult leadership education, program development, or experiential learning - you have led program portfolios, you understand learning design from the inside, and you are fluent in the frameworks and traditions that Hollyhock draws from.
• A track record of leading teams through change, with genuine respect for what exists and conviction about what needs to shift. You know the difference between moving fast and moving well.
• Experience designing cohort-based, curriculum-led, or immersive leadership programs - you have done this work, not just managed people who have.
• Financial fluency at the program level: you can build and manage budgets, think carefully about program mix and pricing, and own revenue performance.
• A commitment to equity, cultural humility, and building learning environments that reflect the diversity of the communities they serve.
• Comfort in a lean, distributed, values-led environment where infrastructure is modest, ambiguity is real, and the work is genuinely important.

The Details:

Compensation - $80,000 - $105,000 CAD, based on experience

Benefits - Comprehensive package including health and dental, vacation including statutory holidays and wellness days; employee assistance program. One complimentary Hollyhock course per season, plus up to 50% off additional program tuition. Discounts at the Hollyhock Store, Bodywork Studio, and on accommodations and meals at Hollyhock. While working on campus: complimentary staff breakfast, daily movement class, access to the spa, hiking trails, gardens, guided nature tours, and attendance at presenter evenings and special events.

Location - Remote, with approximately 4-8 weeks per year on Cortes Island.

Reports to - CEO