Arena Careers

At Crooked, we believe the answer to a rising authoritarian movement is a democratic movement powerful enough to fight it and (fingers crossed) defeat it. That means using all the tools at our disposal as a media company to help build a massive, diverse coalition united behind a core set of democratic values: freedom, equality, compassion, and the rule of law.

Job Summary:

Crooked is hiring for an Executive Director to lead Crooked Ideas, a 501(c)(3) not-for-profit organization. The Executive Director is a seasoned leader who can help Crooked Ideas execute on its content-based strategy for 2026 and beyond. They will lead a small but nimble team working alongside the Crooked Media ecosystem and ensure the organization meets its strategic content goals while delivering value to their fundraising partners.

This role is based out of our Los Angeles office, and follows a hybrid schedule based on the jobs needs. We are ideally looking for Los Angeles-based candidates or candidates willing to relocate within the first 3 months of accepting an offer.

How You’ll Spend Your Time:

Organizational Leadership & Strategy

• Provide executive leadership for all aspects of Crooked Ideas, and oversee ongoing development and growth.
• Guide high-level strategic planning and continue to develop priorities and programs based on learnings and opportunities, and the external landscape, and in alignment with potential and committed funding.
• Establish and develop partnerships, projects, and ongoing strategic alignment.

Fundraising & Budget Oversight

• Lead and ensure the achievement of the organizational budget and fundraising targets on an ongoing basis, including support of current projects.
• Cultivate relationships with philanthropic partners, individual donors, and aligned funders.
• Ensure timely and accurate assessment of program goals and reporting of outcomes to donors.
• Oversee and manage organizational budget and finances.

Operational & Legal Oversight

• Ensure organizational health, legal compliance, and strong governance practices.
• Oversee and manage key vendor relationships, contracts, and nonprofit reporting requirements.

Board Management

• Oversee, plan and lead quarterly board meetings with accurate and concise reporting on program outcomes, budget health, and fundraising goals.
• Manage board composition, development and ongoing communication/relationships.

Content Strategy, Program Development, and External Partnership Development

• Lead strategy development and execution of Crooked Ideas’ impact-focused content and campaigns, and ensure alignment with overall program goals and donor and grant commitments.
• Partner and develop collaborative projects and campaigns with internal teams and external creators and influencers to develop truly impactful editorial, social and media content, in accordance with the current donor and grant commitments and in alignment with audience growth goals.
• Develop, manage and extend partnerships with the external social movements associated with the various campaigns, including the climate movement.
• Monitor and stay connected to the various cultural, political, and policy landscapes to ensure programming is timely and relevant.
• Support evolution of Crooked Ideas strategy.

Marketing & Communications

• Oversee execution of marketing, social media, and audience development strategy in order to achieve program strategy and outcomes, according to donor goals and commitments, as well as potential fundraising opportunities, and in line with audience growth goals.
• Guide messaging and public-facing communications and campaigns in alignment with the organization’s voice and values.
• Represent the organization in public forums and key partner convenings.
• Oversee development and execution of an Annual Report on Crooked Ideas, for distribution to external partners and stakeholders.

Team Leadership & Culture

• Hire, support and manage a high-performing, mission-driven team.
• Collaborate with key constituents and colleagues who provide services to Crooked Ideas.
• Foster a culture of creativity, collaboration, experimentation, and fairness.
• Work with the board to ensure strong organizational health and team support.

What You Bring to the Table:

• A strong sense of ownership and excitement related to our mission,
• A self-starter and leader who will guide the way of our program initiatives.
• A strong collaborator who is eager to create a positive environment to work well with others and bring multiple stakeholders together to accomplish amazing things.
• A strategic thinker and doer who maintains a strong balance between creative vision and project management skills, which many times will require one to actively roll up their sleeves to bring great ideas to life.
• A facilitator of constructive conversations, who values diverse perspectives and promotes critical thinking to ensure compelling ideas are shared and valued.

What Experience You Have:

• Senior leadership experience in nonprofit organizations.
• Strong fundraising track record (especially with foundations, high-net-worth donors, and/or content-based funding)
• Experience in content development, strategic communications, or storytelling for change
• Deep familiarity with climate and democracy issues, social-impact work, or movement-building.
• Strong understanding of nonprofit operations and legal compliance.
• Values-driven, collaborative, and the ability to navigate complexity with humor and humility.

• Have startup experience (especially in nonprofit or media ventures).
• Know your way around political media, the impact/narrative space, or cultural campaigns.
• Have successfully managed a leadership transition before

This job description provides a summary of how you’ll spend your time, but is nowhere near exhaustive, so other duties may be assigned over time.

Pay and Perks:

At Crooked, we believe in paying employees at market rates that are informed by salary surveys and industry benchmarks. In addition to competitive salaries, we offer full-time employees excellent benefits including:

• Competitive salaries
• Paid healthcare
• 401k match
• Unlimited discretionary time off
• Paid leave including, sick, bereavement, pregnancy loss, and disability leaves
• 20 weeks of paid parental leave
• Commuter reimbursement or paid parking
• Communications stipend
• Professional development opportunities
• Did we also mention our offices are closed at the end of the year?

Once we’re ready to extend an offer, we look at the individual’s years of relevant experience and other compensable factors to determine a competitive offer. And for this role, the total potential cash package ranges from $175,000-$200,000, which is inclusive of a base salary and an annual bonus. We evaluate bonuses based on company and individual goal achievements.