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Online to Offline Strategy Group

Executive Director

Remote / National

Executive Director
Salary: $120,000 – $150,000 dependent on experience
Location: Remote in the US.
Employment: Full-time, permanent position

ABOUT ONLINE TO OFFLINE STRATEGY GROUP
The Online to Offline Strategy Group (O2O) is a nonprofit organization dedicated to helping social justice organizations and labor unions harness digital tools and strategies not just for mobilization, but to build lasting bases of leaders for long-term organizing and real-world action.

Our online-to-offline organizing methods were born out of worker-led campaigns to change Walmart. Since then, our team has partnered with hundreds of groups —from smaller community-based nonprofits to major labor unions like SEIU and CWA— to build digital capacity, leverage innovative, scalable digital organizing methods, and run winning campaigns.

O2O is a worker self-directed nonprofit, so a culture of mutual trust, care and accountability is part of our DNA. We each have a fair amount of autonomy over our day-to-day work, and we make big decisions about our work, working conditions, and organizational direction in a collaborative fashion. 

We are a team of roughly 20 people (including full-time and part-time staff and contractors) who are located across the United States. We strive for a culture where each member of our team (whatever their role) is empowered and supported to do their best work in a sustainable way.

POSITION SUMMARY
After six years, our founding Executive Director will be transitioning out of his role in September. He will be leaving the organization on a strong financial footing. 

We are now seeking an experienced, relational, and emotionally intelligent leader to become our new Executive Director. 

In this role, the Executive Director will:

1. Serve as the senior leader responsible for advancing O2O’s impact across the broader social justice ecosystem and labor movement.
2. Lead efforts to identify and capitalize on opportunities to bring in additional revenue (both earned revenue and foundation grants).
3. Work hand in hand with the management team and staff to sustain strong organizational culture, business, and effectiveness. 

This is an excellent opportunity for someone who wants to take a leadership role in a social justice organization that seeks to produce consistently excellent work in the context of a healthy, sustainable and caring work culture.

Are you an inclusive, emotionally intelligent leader with a track record of building sustainable revenue streams and successfully managing complex stakeholder, funder or client relationships?

Are you an accountable manager who has a knack for building strong, collaborative relationships grounded in mutual trust and respect?

Are you a seasoned social justice practitioner who understands organizing and advocacy work, and has an ongoing curiosity about how digital organizing can build power and win structural change?

If so, read on! 

RESPONSIBILITIES:

Fundraise and develop new business through existing and new partners (clients).

• Lead efforts to secure new revenue across our practice areas (campaigns, training and rapid response programs). 
• Translate client needs into scoped projects, proposals, and long-term partnerships.
• Maintain strong relationships with existing partners to ensure retention and expansion.
• Support O2O team’s development and ability to bring in new work and manage relationships with budget decision makers at other organizations.

Cultivate and manage high-level relationships with our partners.

• Serve as an ambassador for O2O with movement leaders and funders, in public forums and in coalition spaces.
• Build, deepen, and manage strategic relationships with national, state and local labor unions, worker organizations, and social justice groups.
• Identify opportunities for deeper alignment and collaboration across campaigns and organizations that O2O supports.

Ensuring our team provides exceptional work across our programs.

• Work with campaign managers to ensure high-quality strategy, execution, and service across our projects.
• Support the implementation and experimentation of new, innovative online-to-offline organizing tactics and digital tools are incorporated into our programs.
• Ensure best practices are being utilized across our campaigns and align with O2O’s methodology and campaign goals.
• Troubleshoot complex campaign challenges and provide strategic guidance.

Managing the organization’s budget.

• Lead the annual budget process with the management team and O2O board, including financial planning, and revenue forecasting.
• Monitor organizational financial health to ensure sustainable growth.
• Work with staff and the Epic Works team to provide timely financial reporting, invoicing, and expense management.
• Align financial decisions with organizational strategy and values of O2O.

Support the management team with staff development & review.

• Mentor and coach a diverse team, fostering a relational culture of collaboration, accountability, and iterative improvement with a strong justice, equity, diversity, and inclusion lens.
• Support the management team in performance review processes to ensure consistency, fairness, and alignment with organizational goals.
• Support managers and staff in setting clear performance expectations, goals, and professional development plans.
• Work with the management team to review and refine staff evaluation tools, policies, and procedures to improve effectiveness and engagement.
• Ensure compliance with O2O & EpicWorks policies and employment regulations.
• Coach and advise O2O managers and staff on handling employee performance issues, feedback conversations, and career growth opportunities.

Serve as the primary point of contact with our professional employer organization (PEO), EpicWorks.

• Work with our EpicWorks point of contact to ensure invoicing, contracts, budgets, legal and compliance work are in order.
• Serve as the liaison between O2O and EpicWorks for matters related to benefits, costs & HR training.

SUCCESS IN THE FIRST YEAR LOOKS LIKE: 

• Being the primary driver in new revenue, personally bringing in hundreds of thousands of dollars.
• Developing thoughtful and trusting relationships across the organization, management team, and with key partners. 
• Identifying systems for improvement internally to coordinate and execute work across our team, and externally to improve outcomes with our partners.
• Deepening O2O’s relationship with new and existing partners including labor unions, social justice organizations and foundations who wish to work with us.
• Strengthening fiscal management and planning in coordination with the managers and O2O’s staff board.

QUALIFICATIONS

Required Qualifications:

• You resonate deeply with O2O’s mission, vision and values, and would be excited to play a leadership role in a worker-directed non-profit.
• 10+ years of professional experience with progressively increased responsibility in labor, advocacy, or social justice movements.
• Proven experience building, managing, and mentoring high-performing teams, including some experience managing a team of at least 10 people.
• Demonstrated success securing large client contracts or grants from foundations and/or major donors.
• Proven ability to manage multiple high-stakes projects simultaneously and navigate complex, fast-moving situations that required quick, sound decisions under pressure.
• Exceptional communication and partnership-building skills, with the ability to work collaboratively with a diverse set of organizations and leaders.
• Commitment and deep understanding to equity and social justice, including experience applying anti-racist and other anti-oppression principles in your work (both the substance of your work and how you show up in the workplace).
• High emotional intelligence, a growth mindset, and the ability to give and receive feedback well. 
• A transparent, inclusive, collaborative and high-integrity leadership style. 
• Proven experience organizing and building power alongside communities most harmed by systemic injustice with direct accountability to those leaders.
• Experience in strong financial management, including budget preparation, analysis, decision-making, and reporting.

Preferred Qualifications:

• Practical understanding of online-to-offline organizing strategies and tactics – i.e. how to use digital tools (P2P texting, CRMs, digital ads, etc.) to mobilize people quickly and effectively.
• Experience leading organizing campaigns and utilizing digital tools for organizing. 
• Experience leading or managing in a unionized, co-op, worker-led nonprofit or similar environment.
• Agency experience or experience managing organizational stakeholders in a coalition (or similar) setting.
• Experience with budget management and fundraising for campaigns or programs that were $2 million or more.
• Significant experience driving structural and cultural change within an organization in a collaborative, values-aligned manner.
• Ability to speak and write in Spanish.

COMPENSATION AND BENEFITS:
This is a full-time position, with an annual salary of $120,000 to $150,000 and a comprehensive benefits package. 

Comprehensive Benefits Package includes:

• Paid health, vision, and dental insurance
• 401K retirement plan with 3-6% employer match
• 17 vacation days annually for first 2 years, 12 paid sick days, and 2-week paid winter break
• 12-week paid parental leave after one year of employment
• 2-month sabbatical after 4 years of employment
• In vitro Fertilization (IVF) and other reproductive health coverage
• Life Insurance
• Pet Insurance 
• Health Savings Account (HSA)
• Flexible Spending Account (FSA)
• $500 annual home office stipend
• $1,000 bi-annual technology stipend
• $1,000 annual professional development stipend

ADDITIONAL DETAILS 
This is a full-time, remote role that can be based in any state in the contiguous US. That said, travel will average 3-5 days a month (with more anticipated in the first year), so easy access to a major airport is important.

Additionally, we work primarily in Central and Eastern time zones and have a preference for someone who is either based there or comfortable aligning their schedule accordingly. 

This role reports to O2O’s Board of Directors, which is composed of staff members and serves as the organization’s governing body. This reflects O2O’s structure as a worker self-directed nonprofit, where staff collectively hold organizational authority.

ABOUT THE HIRING PROCESS
We are currently anticipating three rounds of virtual interviews conducted over Zoom, as well as a written assessment that should take less than three hours to complete. Anyone who completes the assessment will be paid an honorarium for the time you spend on it. Finalists will be asked for references. 

We are hoping the first round of interviews will be complete by the end of July, and the hiring process will be complete in time for a start date on or before October 12, 2026. 

Please direct any questions to hiring@o2ostrategy.org. In addition, please send an email to that address if you require any kind of accommodations related to the application and hiring process.

How to Apply:
We encourage anyone who is interested in this role to apply ASAP and no later than the priority application deadline of 11:59pm Pacific Time on Sunday, July 12, 2026. 

To apply, please email your application to: hiring@o2ostrategy.org with the subject line: “Executive Director — First Name Last Name”

Applications should include a résumé and answers to the following questions in lieu of a traditional cover letter:

1. Why are you applying for this job? Why are you interested in working for O2O, and what specifically draws you to serving as O2O’s senior leader in advancing our impact across the broader social justice ecosystem and labor movement? Please be specific. (Suggested word limit: 250)
2. Please describe your overall track record bringing in revenue. What types of revenue have you been responsible for bringing in, and at what scale? In addition, please describe the single largest contract, grant or gift that you’ve personally closed. (Suggested word limit: 200)
3. What’s a campaign or movement moment that shaped how you think about building power? What made it work (or not), and what lessons have you drawn from it? (Suggested word limit: 200) 
4. How did you hear about this position? Please be specific.
5. Optional: If there is anything else you think is especially important for us to know about you as we evaluate your application (particularly if it is not reflected elsewhere in your application), you are welcome to include it. 

Questions about this position or the application process (including any requests for reasonable accommodations) can be sent to: hiring@o2ostrategy.org.

O2O is an equal opportunity employer with a strong commitment to equity. O2O values a diverse and representative workplace. We believe that historically marginalized communities must be centered in the work we do and strongly encourage People of Color, people from working class backgrounds, women and LGBTQ people to apply. O2O is committed to attracting, developing and retaining exceptional people, and to creating a work environment that is dynamic, rewarding, and enables each of us to realize our potential. 

People of color, women, and LGBTQ candidates are strongly encouraged to apply.

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Job Posting Courtesy of UnionJobs.com