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Head of Operations

Toronto (remote to begin)
10+ years
Full time
$90,000 to $120,000


The Head of Operations (HOO) is a newly created position at Rainbow Railroad, reflecting the extraordinary growth the organization has experienced in recent years and the importance of expanding its senior leadership capacity and strengthening the systems, structures, and strategies that ensure operational excellence. The new HOO will join a dynamic, high-growth organization and an innovative global leader in providing life-changing and life-saving direct services.

The HOO will be a member of the senior leadership team with responsibility for continued organizational development across operations, finance, planning and administration, and human capital. They will function as a key strategic and thought partner to Executive Director, Kimahli Powell (he/him) and play a critical role in operationalizing the goals and objectives set out in Rainbow Railroad’s strategic and annual plans.


Reports to the Executive Director. Manages two direct reports, a Director of Finance and a Director of H.R. & Administration. Supervises a team of six (when fully staffed). 

PRIMARY RESPONSIBILITIES:  [NOTE: It is understood that no single candidate will have equal expertise in all these areas of responsibility.  Successful candidates will possess a compelling combination of many of them and the self-awareness and wisdom to leverage existing and/or new resources for support in the area(s) where they lack personal mastery.]

Organizational Leadership & Support 

  • Work with the Executive Director to develop and implement organizational plans, strategies, and systems to accomplish growth objectives;
  • Analyze, assess, and advise the Executive Director on financial and operational issues that could impact Rainbow Railroad’s pursuit of strategic goals 
  • Provide senior leadership experience and management perspective to Rainbow Railroad in scaling and expanding the organization;
  • Advise on business risks and opportunities, provide assessments of organizational performance, and keep the Executive Director and leadership team apprised of progress on operational priorities; 
  • Drive the cultivation of a cohesive work culture and foster a success-oriented, accountable environment within the organization.

Financial Management & Oversight

  • Manage and support the Director of Finance and provide oversight/enhancement to financial operations, budgeting, and financial management processes; 
  • Lead and oversee organizational strategies for annual budget, resource allocation, and financial planning; 
  • Oversee financial activities, systems, and controls to ensure the immediate and long-term fiscal integrity of the organization; 
  • Ensure fiscal transparency and provide the Board with regular information about the financial health of the organization. 

H.R. & People Operations

  • Manage and support the Director of H.R. & Administration and provide leadership to all People Operations;
  • With the Director of H.R. & Administration, manage the development and implementation of human resource policies, procedures, and protocols to support staff and organizational growth and expansion;
  • Up-level recruitment processes, establish staff performance and professional development goals, assign accountabilities, help establish work plans and priorities, and manage the annual performance review process;
  • Help create an environment and culture that reflects the organization’s values, encourages strong performance, rewards excellence and productivity, and ensures safety in all operations for staff and volunteers;
  • Ensure policies, practices, programs, and processes are administered effectively and in compliance with relevant laws and regulations.

Planning & Administration 

  • With the Head of Impact, co-lead the organization’s annual planning process and act as steward of the plan – making sure the organization is on track to deliver on its goals and adjusting as needed; 
  • Manage the organization at the 10,000 feet level, ensuring that the financial processes, program support, financial management, and development systems match Rainbow Railroad’s needs at present and into the future;
  • Look for ways to improve, problem-solve, and innovate on systems and tools, including case management systems, donor processing, website, etc.;
  • Co-lead (with the Head of Impact) risk management processes for the organization, working closely with the Risk Management Committee of the Board.

Board Relations 

  • Establish and maintain positive, productive, and transparent working relationships with Rainbow Railroad’s Board of Directors; 
  • Assist the Executive Director in managing relationships and communications with the Board, including staffing committees, preparing and presenting information at Board meetings, and supporting individual Board members and projects as appropriate;
  • Act as key operational liaison with the Executive Committee and standing Committees of the Board, supporting the Executive Director and the senior management team whenever necessary.


A meticulous planner, the HOO manages the strategic planning, annual planning, staffing, and budgeting processes while innovating tools and processes that allow team members to meet and exceed desired results. The HOO will know Rainbow Railroad’s finance, administration, and operational goals inside and out, and will be ready to roll up their sleeves and provide direct assistance wherever needed. Regardless of professional experience, this person will have demonstrated passion for global human rights and will understand and operate with the sense of urgency the work and organization require.


  • Minimum of 10 or more years of leadership experience in a nonprofit organization, government agency, and/or private sector company; 
  • Professional track record of supporting organizational growth, development, and improvement; 
  • Exceptional operations, finance, systems development, and people management skills; 
  • Financial management experience and acumen and ability to make strategic financial decisions, oversee financial reporting, and build/manage budgets;
  • Previous experience developing and implementing human resources systems, tools, and  protocols; 
  • Excellent project management and problem-solving skills;  
  • Knowledge and experience in utilizing organizational development models and assessment tools;
  • Demonstrated expertise in organizational design, job analysis/design, creation of staffing models, and development and stewardship of culture change initiatives;
  • Understanding of anti-oppression frameworks;
  • Previous experience in a startup or high-growth environment strongly preferred; 
  • Experience working effectively and collaboratively with a volunteer Board of Directors or similar governing body is also desired. 


University degree in business administration, organizational development, human resources, or related discipline – or equivalent combination of lived and professional experience – is required.


  • Personality type that thrives in a fast paced, start-up style environment;
  • Self-starter with a bias for action, but also able to work collaboratively with cross functional teams;
  • Energy, passion, and exceptional capacity for managing multiple initiatives at once
  • Ability to pay keen attention to detail without losing sight of larger objectives;
  • Nimbleness and flexibility to pivot, shift gears, and/or re-prioritize seamlessly without losing patience or focus; 
  • High level of comfort holding individuals and teams accountable to departmental and organizational goals;
  • Fair, honest, inclusive, management style and ability to lead team members from a broad range of professional backgrounds and personal identities; 
  • Problem solver – able to identify bottlenecks and gaps and work towards solutions;
  • Cultural competency and humility, including intersectional lens and understanding of marginalized individuals, communities, and populations; 
  • Professional maturity, diplomacy, and well-developed judgment when dealing with sensitive matters;
  • Empathy and ability to nurture and support a team in a sometimes stressful environment.


Rainbow Railroad is offering a compensation package that includes base salary in the range of $90,000 to $120,000 (commensurate with skills and experience) and a comprehensive benefits plan. 


Kevin Chase Executive Search Group has been retained to lead this recruitment effort on behalf of Rainbow Railroad. Kevin Chase Executive Search Group works only with equal opportunity employers. No applicant will be discriminated against because of racial or ethnic identity, religion, sexual orientation, gender identity or expression, sex characteristics, or disability. Individuals of LGBTQI+, BIPOC, and/or immigrant or refugee experience are strongly encouraged to apply. 

To apply, please submit a complete resume with full employment history and a cover detailing your interest in the position and the professional and/or lived experience you believe make you a uniquely qualified candidate for this role to [email protected]


 Kevin Chase, Managing Partner      

[email protected] 

Catie DiFelice, Senior Associate

[email protected]


Kevin Chase Executive Search Group

1800 Hi Point Street

Los Angeles, CA  90035 

All inquiries, applications, or referrals will be held in strict confidence.


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