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Head of Operations

  • Posted:Apr 25, 2022
  • Apply by:May 25, 2022
  • Job Type
  • Full Time
  • Job Level
  • Senior
  • Location
  • Toronto, ON
  • Impact Area
  • Human Rights
  • Impact Category
  • Nonprofit
  • Company Type
  • Nonprofit

About this position

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).

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.

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.

About us

Rainbow Railroad stands at the forefront of the global movement to advance and protect the human rights of LGBTQI+ people wherever they are in the world. With a focus on helping those most vulnerable find safety from persecution and violence, Rainbow Railroad is internationally recognized for its work in providing support and resettlement assistance to individuals in some of the most virulently anti-LGBTQI+ locations in the world.

In this time when there are more displaced people around the world than any period since World War II, LGBTQI+ people are uniquely vulnerable due to systemic, state-enabled homophobia and transphobia. These factors can displace LGBTQI+ individuals in their own country and/or prevent them from escaping harm. In partnership with a global network of LGBTQI+ organizations and human rights defenders, Rainbow Railroad coordinates directly with individuals experiencing violence to get them out of danger.

Initially founded as an all-volunteer operation in 2006, Rainbow Railroad has since received formal charitable and nonprofit recognition in both Canada and the United States. Despite its relatively short history, Rainbow Railroad enjoys a strong and growing reputation for its work on behalf of LGBTQI+ individuals. Through its Emergency Travel Support programs, the organization has facilitated travel to a safe destination for more than 1,500 people. And while this work has tremendous impact, it is practically impossible to fully resettle every single person who reaches out to Rainbow Railroad for help. In response, the organization is expanding its programs and services to support thousands of additional LGBTQI+ individuals in the places they live. These expanded interventions include medical care; access to essential medicine; in-country relocation to safer housing; short-term financial aid; private sponsorship of refugees; and active partnership with other global LGBTQI+ and human rights organizations to provide lifesaving support.

In partnership with a global network of LGBTQI organizations and human rights defenders, Rainbow Railroad coordinates directly with individuals experiencing violence to get them out of harm’s way. Around the world, we are recognized for our efforts to support and protect the thousands of LGBTQI people living in countries which criminalize their existence.

With headquarters in Toronto and an office in New York City, Rainbow Railroad employs a dedicated and mission-driven staff of 17 full- and part-time employees and a network of 130+ volunteers in Canada and around the world. The organization is almost entirely funded through private donations and has a current revenue budget of more than $6 million, representing an increase of 300% in just over three years.

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