Chief Business and Operations Officer

The Leadership Institute dba Hollyhock • Full-time • Remote (BC, CA) • C$ 100k - C$ 125k / year • 1m ago

Position: Chief Business & Operations Officer (CBOO)

Reports to: Chief Executive Officer (CEO)

Start Date: April 1, 2026 or sooner if available

Location: Hybrid - Remote within Vancouver, Vancouver Island, or in-person on Cortes Island (If remote - ~8-12 weeks/year on site at Hollyhock)

Compensation: $100,000-$125,000 plus comprehensive benefits package

Term: Full-time (40hrs/week) (0.8 FTE possible)

ABOUT HOLLYHOCK

Hollyhock is a globally recognized transformative learning and leadership center with a beautiful nature-based campus located on the traditional territories of the Klahoose, Tla’amin, and Homalco Nations on Cortes Island, BC. For over 40 years, Hollyhock has convened leaders, changemakers, artists, activists, and seekers to explore the inner and outer dimensions of social and ecological transformation.

Community, connection and impact are the foundation of Hollyhock, through each uniquely curated gathering or program. Our vision is a living and loving planet for all, we nurture inspired leadership through collective and immersive experiences, through renewing people’s connections to themselves, one another, and the natural world.

At Hollyhock, staff really care about each other. Season after season, staff consistently report that one of the best things about their work is the relationships they build with their colleagues.

We believe that our staff must reflect the diversity of the communities we serve. We strongly encourage applicants of all genders, ethnic and cultural backgrounds, sexual orientations, abilities, and with a range of life experiences to apply. Please feel free to state any aspects of your identity that may contribute to diversity in our workforce in your cover letter, so we can prioritize your application.

POSITION SUMMARY

Hollyhock is in a profound period of renewal, expanding its vision and impact as a bioregional center of excellence for transformative leadership, community and place-based learning, and regenerative practice. To deliver on this bold vision, the CEO seeks a Chief Business & Operations Officer (CBOO) to serve as their primary partner in leading the organization and translating Hollyhock’s new strategic plan into action over the coming decade.

The CBOO will have responsibility for both financial and operational oversight within the organization. They will support the CEO and Senior Leadership Team by overseeing day to day operations, organizational alignment, and team management. Working closely with the Director of Operations, they will help ensure that there are well-functioning and values-led operations across campus systems, people & culture, finance, risk, policy, and organizational infrastructure.

Second, the CBOO will lead Hollyhock’s enterprise-level business strategy, revenue performance, and the optimization of systems to ensure the financial wellbeing of the organization, improve financial resilience, and align revenue-generating activities with its long-term mission. The CBOO’s role is to bring business discipline, integration, and forward-looking planning to an organization with strong operational, programmatic, and development leadership already in place. The role focuses on how the organization sustains itself financially, how its revenue streams work together, and how strategy is translated into clear priorities and measurable outcomes.

This role is well suited to a senior business leader with strong people skills who is comfortable operating at the intersection of operations, finance, and mission alignment, and who brings clarity rather than complexity to decision-making.

This is the organization’s second-in-command, enabling the CEO to focus on vision, strategy, partnerships, and philanthropy while the CBOO ensures the organization is operationally exceptional, culturally strong, and financially durable.

KEY RESPONSIBILITIES

1. Organizational Leadership & Strategic Plan Implementation

Oversee day-to-day internal operations and management of the Senior Leadership Team
Hold the operational center of gravity, enabling the CEO to focus on vision, partnerships, development, and external relations
Act as the CEO’s principal partner in operationalizing the strategic plan (2026–2035).
Translate mission, vision, and strategic priorities into annual plans, KPIs, budgets, and cross-team execution frameworks.
Serve as a member of the Senior Leadership Team, modeling clarity, collaboration, and accountability across the organization.
Work closely with the Director of Operations to ensure cross-functional integration across the organization and ensure campus and remote teams, processes, and systems are aligned and working with coherence.
Surface risks, interdependencies, and decision points to support timely and informed executive and Board decision-making.

2. Business Strategy & Revenue Model Stewardship

Lead the development and ongoing refinement of Hollyhock’s multi-year business strategy, ensuring alignment between mission, market realities, and financial sustainability.

Assess the performance and mix of current programs and revenue streams and identify opportunities to strengthen contribution margins and reduce volatility.

Guide pricing strategy, portfolio balance, and revenue assumptions in collaboration with functional leaders.

Identify and evaluate selective growth opportunities, pilots, partnerships, or new revenue concepts, focusing on feasibility, alignment, and financial impact rather than execution.
Generate leads and close deals for high level sales and revenue opportunities, e.g. for top tier group bookings
Track and report on key operational performance indicators and support continuous improvement.

3. Financial Leadership & Performance Oversight

Serve as the CEO’s primary thought partner on business and financial matters.
Create systems for and execute multi-year revenue forecasting, scenario planning, and financial modelling to support strategic decisions.
Review financial and business performance across major revenue areas and identify trends, gaps, and corrective actions.
Support resource allocation decisions by linking financial insight to strategic priorities.
Ensure that business decisions are supported by clear, accessible financial information and assumptions.
Oversee finance, budgeting, compliance, and financial reporting, working closely with the fractional CFO
Build multi-year planning dashboards (budgets, cash flow, reserves, endowment strategies).
Strengthen internal controls, business processes, and organizational policies.
Partner with the CEO and development team to support financial sustainability and philanthropic strategy.

4. People, Culture & Organizational Development

Work closely with the Director of Operations and People and Culture Manager to implement the CEO’s vision for Hollyhock’s culture and people development
Support the development and growth of managers across the organization through developing clear performance management frameworks and improved systems for onboarding, feedback, training, coaching, and mentorship.
Partner with the CEO to develop and operationalize Hollyhock’s emerging internal leadership pathways.

Coach and support senior leaders in strengthening business thinking, planning discipline, and cross-functional collaboration.

5. Systems Stewardship & Risk Management

Lead the design, assessment and continuous improvement of organization-wide systems, workflows, and decision-making structures.
Support effective collaboration between departments by aligning systems and tools.
Oversee the implementation and upgrading of key operational tools, technology platforms, and vendor relationships.
Assess the current accounting and financial management practices and systems, and design and implement advanced systems to support more efficiency and accuracy.
Support operational risk awareness, escalation pathways, and readiness planning.

Help the organization move from reactive decision-making to a more deliberate, planned, and data-informed operating rhythm.

6. Board and Governance Support

Prepare operational reports and dashboards for the CEO and Board.
Support policy development, risk management, compliance, and special initiatives.
Ensure governance information flows smoothly and accurately between staff and Board.

QUALIFICATIONS

Education & Experience

MBA or equivalent senior executive experience demonstrating strong business judgment and financial acumen.

8–12 years of senior leadership experience in mission-driven, hospitality, education, retreat, or service-based organizations.

Demonstrated success designing and implementing business strategies tied to financial outcomes.

Strong financial literacy, including expertise in forecasting, budgeting, and performance analysis.

Experience working across functions and integrating diverse teams toward shared business and organizational goals.

Familiarity with customer experience or service-based environments; hospitality or campus-based experience is an asset, not a requirement.

Exposure to sustainability or regenerative business practices is beneficial but not essential.

Leadership Qualities

Strategic, pragmatic, and execution-oriented.
Calm, grounded, and relational, with strong judgment.
Able to hold complexity without overcomplicating solutions.
Comfortable operating as a second-in-command rather than a solo authority.
Clear communicator who builds trust across staff, executives, and Board.
Comfortable holding mission devotion and financial discipline simultaneously.

Personal Alignment

Resonates deeply with Hollyhock’s mission and values.
Appreciates land-based learning, community partnerships, and regenerative futures.
Thrives in purpose-driven environments where business strategy and social transformation intersect.
Enjoys working in both remote/at-home office and in a rural, natural setting

COMPENSATION

$100,000-$125,000 (Salary commensurate with experience)
Comprehensive benefits package, including:
- Health, dental and life insurance
- Vacation, statutory holidays, wellness days
- Employee assistance program (EAP) for mental health and well-being support
Flexible and hybrid work with time on Cortes Island (~8-12 weeks per year)
One complimentary Hollyhock course per season, plus up to 50% off discount on any additional program tuition
Benefits while on campus at Hollyhock:
- Complimentary breakfast
- Discounts at Hollyhock Store, Bodywork Studio, Accommodations (for you and your family members), Meals (for you and your family members)
- Daily movement class (yoga, tai chi, meditation)
- Access to spa, hiking trails, gardens, and more
- Guided nature tours
- Attendance at Hollyhock Presenter evenings and special events
- Staff development trainings

APPLY

To apply please email your cover letter and resume to:

jodi@hollyhock.ca

This position is open until it is filled. Please submit your application as soon as possible.

Only short-listed candidates will be contacted.