Managing Director

Tom O'Connor Consulting Group

Washington Dc, DC 20004




Jul 01, 2022

The Managing Director’s primary responsibilities will be in the following areas:

Organizational Leadership & Strategic Vision

  • In partnership with the Artistic Director serve as the executive leadership of Woolly Mammoth, collaborating on a stewardship model for the company that centers the art and programs of the theatre, while building organizational sustainability through a commitment to quality, equity, inclusion, anti-racism, financial health and acumen, and attention to community.
  • In collaboration with the Board of Directors and Core Leadership Team, align business strategies with the overarching company goals as articulated in the strategic plan.
  • With the A.D., model communication practices that ensure that key stakeholders in all areas of the organization – board, staff, core partners, and others – are well-versed in annual operations plans, goals, metrics, and progress tracking.
  • Be a mentor and advisor to Woolly staff, with a focus on people management, recruitment, and retention of team members in a challenging era of changing employee expectations and needs.

Culture and Community

  • In partnership with the A.D. and the Leadership Team, oversee and model Woolly company values in all theatre operations and community relationships.
  • Co-lead an organizational culture that welcomes productive experimentation, in part by encouraging change and making room for failure—all while building sufficient elements of stability and clear direction to support these values.
  • Provide leadership, and space and time, for long-term planning, vision clarity, and the strengthening of operational infrastructure as part of developing team capacity for change and nimble thinking in those in-the-moment times of need or opportunity.
  • Provide vigilance to prioritize the continuous learning required to be an anti-racist organization, ensuring ongoing conversation, training, and evaluation of progress to ensure that company practices reflect growth in incorporating commitments to those learnings.

Resource Development & Board Engagement

  • Provide leadership to the development team to generate overall strategy and philosophy for national and local fundraising and manage a portfolio of direct personal engagement in major gift cultivation and solicitation.
  • Provide leadership and support to the marketing department to increase both ticket sales and brand clarity, fostering direct show sales as well as increased institutional awareness.
  • With Board leadership, work to deepen engagement of a passionate Board, creating opportunities to grow into an even stronger and more impactful group in support of the work of Woolly.
  • Manage overall administrative operations through the direct reports—including budgeting, forecasting, and HR needs—in order to track the organization’s health on an ongoing basis, in both financial terms and people terms.
  • Develop, articulate, and implement a vision for strengthening and streamlining the operational infrastructure of the organization to support its mission and impact in its next chapter.
  • Serve as the Woolly liaison to and treasurer of the board for the Penn Quarter Controlling Entity that manages the shared condo block of which Woolly is a part.



Skills and Experience:

  • The ability and desire to work in a collaborative partnership with a co-executive leader; in this case, bringing an authentic passion for the kind of work on stage for which Woolly is renowned, and a personal alignment with and commitment to Woolly’s stated values. With these as touchstones, has the ability to engage in productive, respectful conflict as part of making joint leadership decisions, including presenting a united front once a decision is made.
  • Demonstrated leadership skills in leading a team with distinct areas of expertise and responsibility, and sometimes competing needs; in other words, able to lead with clarity of purpose for the organization, and with respect for each team member’s contribution to the whole and a willingness to step in whenever needed to help resolve unanticipated problems.
  • Strong financial literacy, with a practical understanding of non-profit accounting, to participate in budget creation, understand forecasting models, and ensure accuracy of tracking and reporting.
  • A spirit of entrepreneurship, including an evident comfort with weighing and taking risks, monitoring results and making course corrections as needed; and to build an organizational aptitude that allows the company to seize sometimes late-breaking programming opportunities with equanimity.
  • Experience with and comfort in fundraising that is rooted in belief in the mission and impact of Woolly’s role in the communities it serves, both locally and nationally.
  • Experience in or demonstrated understanding of the position of an executive in a non-profit organization, bridging the connection and understanding between professional staff and a governing volunteer board, and in effect being responsible to and for both of those entities.
  • Experience managing competing priorities in complex settings, and taking an “ecological” approach to decision making (impact of a decision on the entire organization).
  • Strong communication skills, with the authenticity to effectively inspire excitement for Woolly across a range of diverse communities and stakeholder groups.
  • Demonstrated experience in people management, including success managing a highly accomplished and effective staff with a focus on collaborative leadership and a willingness to creatively problem-solve and adapt as situations demand.
  • A demonstrated commitment to anti-racism, an inclusive world view, and a dedication to staying abreast of best practices around creating equity and access and applying them to the work of running an organization.

Qualities and Characteristics:

  • Passion for bold work and a firm belief in the power of theatre as a force for positive social change.
  • Organized and attentive to deadlines and their role in keeping the entire team on track with clear priorities, but also maintains enough long-term focus to know when to be flexible on managing those deadlines.
  • Understands that growth brings occasional pain and tension but can lead through those moments with thoughtfulness and optimism for positive outcomes.
  • Comfortable with uncertainty, and able to move forward even in the face of uncertainty.
  • Belief in the value of engaging authentically with the broadest range of people to share the experience of the theatre, including but not limited to the productions.
  • Ability to build trust and loyalty.
  • Finds joy in collaboration, knows that conflict is normal unless it remains unresolved, and assumes good intentions.

Not sure you meet 100% of our qualifications? Research shows that men apply for jobs when they fulfill an average of 60% of the criteria. Yet, women and other people who are systematically marginalized tend only to apply if they meet every requirement. If you believe that you could excel in this role, we encourage you to apply.

We are dedicated to considering a broad array of candidates, including those with diverse workplace experiences and backgrounds. So, whether you’re returning to work after a gap in employment, simply looking to transition, or taking the next step in your career path, we will be glad to have you on our radar.

Please use your cover letter to tell us about what you hope to bring to this role, and how your background and experience responds to the desired skills and qualities.