Literary Arts is looking for an exceptional leader to serve as Deputy Director to help ensure that strategy becomes action and that every part of the organization moves in concert. The Deputy Director, as a key member of the core Leadership team, reports to the Executive Director (ED) and manages the Director of Marketing & Communications, the Managers running Literary Arts’ cafe and bookstore, and the Audience Services & Office Administration Coordinator.
As the Deputy Director, you are primarily concerned with how the organization functions as a whole — across programs, development, marketing, retail, and staff culture. You are able to see the whole, facilitate alignment, ensure accountability across departments, and drive coordinated execution of the Executive Director's vision.
This role requires a leader with exceptional emotional intelligence who can build trust, navigate complexity, and hold people accountable with clarity and care. The right person is a systems thinker who is equally comfortable facilitating a leadership meet ing, troubleshooting a retail staffing challenge, or coaching a director through a difficult personnel situation. You are drawn to the how of making mission -driven organizations work , ensuring cohesion and alignment , and bringing out the best in people.
Core Areas of Responsibility
Organizational Integration & Execution
- Collaborate with the Executive Director and the rest of the leadership team (an exceptional, dedicated group of 8) to translate organizational vision into systems, strategic priorities, and coordinated execution.
- Ensure that the individual department priorities align with the Executive Director's vision and the organization's strategic plan.
- Lead quarterly and annual planning processes in partnership with the Executive Director, translating long-term priorities into clear work plans with defined milestones, ownership, and timelines.
- Maintain the leadership team meeting cadence (weekly, monthly, quarterly), ensuring agendas are focused, commitments are tracked, and the team operates with transparency, directness, and accountability.
- Model and reinforce a culture of accountability, follow-through, and healthy conversation among the leadership team.
- Lead preparation for all-staff meetings, ensuring information flows clearly between leadership and the broader team.
- Represent Literary Arts in the media and with board members, funders, and community stakeholders, as needed.
People, Culture, & Internal Communication
- Support healthy organizational culture by overseeing internal communication, staff engagement, and the resolution of personnel or culture issues.
- Coordinate with Literary Arts’ external HR partner (Xenium) on employee relations, hiring processes, onboarding, and policy compliance.
- Surface and address emerging personnel or culture challenges early, in partnership with the Executive Director and relevant directors.
- Lead or support change management during organizational growth or transition periods.
Management and Supervision of Key Roles & Functions
- Supervise the Bookstore Manager and Cafe Manager to ensure retail operations deliver a high-quality public experience consistent with the Literary Arts brand and values, strong financial results, operational excellence, and mission alignment. Support coordination among retail managers and program directors to align retail activity, literary programming, events, and community activations in the building. Maintain accountability for customer satisfaction and achieving financial goals.
- Oversee the Audience Services & Office Administration Coordinator (new role) to ensure an excellent and consistent patron experience across ticketing, event bookings and subscriptions, and front-of-house. Develop and refine systems for gathering feedback and continuous improvement. Maintain accountability for patron/customer satisfaction targets achieved across events.
- Supervise the Director of Marketing & Communications, who is responsible for brand strategy and positioning, audience development, internal communications, and marketing initiatives that support organization-wide priorities and earned revenue goals. Work together to ensure that marketing resources are allocated strategically across the organization. Maintain accountability for meeting established marketing KPIs.
Qualifications
Minimum Qualifications
- 10+ years of progressive leadership experience, ideally in nonprofit, arts, or mission-driven organizations.
- Demonstrated experience coordinating initiatives across departments — aligning people, priorities, and execution without relying on hierarchical authority.
- Supervisory experience managing multiple direct reports across different functional areas.
- Experience in and passion for strategic internal communications. Strong written and verbal communications skills.
- Strong financial literacy, including experience with nonprofit budgeting, retail P&L, or earned revenue management.
- Demonstrated high emotional intelligence: self-awareness, sound judgment, discretion, and the ability to navigate sensitive situations with empathy and clarity.
- Exceptional interpersonal, communication, and conflict resolution skills with the ability to build trust at all levels.
- Experience overseeing or coordinating HR functions in partnership with an external HR provider.
Desired Qualifications
- Experience in or passion for the literary arts or arts-adjacent industries.
- Experience in or passion for marketing, retail operations such as bookselling or food and beverage services, or for ticketed events and other customer service environments.
- Comfort with ambiguity and the ability to build structure in a growing, evolving organization.
- Deep commitment to equity, inclusion, and anti-racism.
- Demonstrated ability to represent an organization credibly in an executive capacity.
Compensation & Benefits
Salary: $120,000–$150,000/year, commensurate with experience.
Literary Arts provides a comprehensive benefits package including employer-paid health, dental, and vision insurance; 401(k) with employer match; short- and long-term disability insurance; three weeks paid vacation (increasing to five weeks after five years); three personal days; and approximately 12 paid holidays. As a registered nonprofit, Literary Arts qualifies for Public Service Loan Forgiveness.
About Literary Arts
Literary Arts is a community-based nonprofit arts organization located in Portland, Oregon, with a 40-year history of serving the state’s readers and writers. Our programs include Portland Arts & Lectures, one of the country’s largest lecture series; Oregon Book Awards & Fellowships, which celebrates Oregon’s writers and independent publishers; the Portland Book Festival; and Writers in the Schools, which hires professional writers to teach semester-long creative writing workshops in Portland’s public high schools. Literary Arts’ new headquarters—The Susan Hammer Center, located in Portland’s historical Central Eastside—features an independent bookstore, a podcast studio, staff offices, and community spaces.
To Apply
Send a resume and cover letter that tells us why this position is right for you to applications@literary-arts.org with the subject line "Deputy Director - [FIRST NAME] [LAST NAME]." Please include all attachments in a single PDF. Applications will be reviewed on a rolling basis. For best consideration, submit by June 3, 2026.
We encourage BIPOC (Black, Indigenous, and people of color), members of the LGBTQ+ community, people with disabilities, and other communities historically underrepresented in arts administration to apply. We value a diverse workforce and an inclusive culture. No single candidate will offer every desired skill and characteristic — we take a holistic view of candidates and welcome applications from a wide range of experiences and backgrounds.
