Application Guide

How to Apply for Executive Assistant to the CSO and COO

at Way to Win

🏢 About Way to Win

Way to Win is a unique home for movement politics, donor organizing, and long-term power building, working alongside grassroots organizations to support a multiracial democracy. If you're passionate about progressive social change and want to work remotely with a mission-driven team, this is an inspiring place to contribute.

About This Role

This role provides high-level administrative support to the Chief Strategy Officer and Chief Operating Officer, managing calendars, travel, and expenses while also coordinating cross-functional workflows across operations, HR, finance, and compliance. You'll be a key facilitator of organizational priorities, using modern tools and AI to streamline processes and keep leadership aligned.

💡 A Day in the Life

You start your day by reviewing the CSO and COO's calendars, resolving conflicts, and preparing briefing materials for their morning meetings. Midday, you coordinate with operations, HR, and finance teams to track key deliverables, and use AI tools to streamline expense reporting and meeting notes. You end the day by drafting internal communications and updating project trackers to ensure nothing falls through the cracks.

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🎯 Who Way to Win Is Looking For

  • You have 7+ years of executive-level administrative or operations support experience, ideally in a nonprofit or mission-driven organization.
  • You possess excellent writing and editing skills, with the ability to draft clear internal communications and prepare polished briefing materials.
  • You demonstrate high emotional intelligence, discretion, and sound judgment when handling sensitive information and interacting with senior leaders.
  • You are comfortable with technology and AI-supported workflows, and you proactively seek ways to improve systems and efficiency.

📝 Tips for Applying to Way to Win

1

Tailor your resume to highlight experience with cross-functional coordination across operations, HR, finance, and compliance, not just calendar management.

2

In your cover letter, explicitly mention your comfort with AI and productivity tools, giving an example of how you've used them to improve workflows.

3

Research Way to Win's mission and recent campaigns, and reference how your values align with their commitment to movement politics and multiracial democracy.

4

Demonstrate your writing skills by submitting a clean, error-free application with clear formatting and a compelling narrative.

5

Emphasize your ability to work independently in a remote environment, providing examples of how you stay organized and communicate effectively without direct supervision.

✉️ What to Emphasize in Your Cover Letter

["Your passion for the company's mission and how your background supports movement politics and grassroots organizing.", 'Specific examples of providing high-level support to executives, especially in a remote or nonprofit context.', "Your proficiency with modern tools and AI, and how you've used them to enhance efficiency and organization.", 'Your ability to handle sensitive information with discretion and collaborate across diverse teams.']

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🔍 Research Before Applying

To stand out, make sure you've researched:

  • → Read about Way to Win's recent grantmaking and partnerships with grassroots organizations.
  • → Review the bios of the CSO and COO to understand their priorities and working styles.
  • → Look into the company's use of AI and modern tools by checking their blog or press releases.
  • → Understand the broader landscape of donor organizing and movement politics to speak knowledgeably.
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💬 Prepare for These Interview Topics

Based on this role, you may be asked about:

1 Describe a time you managed competing priorities for multiple executives. How did you stay organized?
2 How have you used AI or technology to improve administrative workflows in a previous role?
3 Why are you drawn to Way to Win's mission, and how does your experience align with movement politics?
4 Tell us about a time you had to exercise discretion with confidential information. What was the outcome?
5 How do you approach cross-functional coordination, especially in a remote setting? Give an example.
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⚠️ Common Mistakes to Avoid

  • Submitting a generic application that doesn't reference the company's mission or specific role requirements.
  • Overlooking the emphasis on technology and AI; failing to mention your comfort with these tools.
  • Not demonstrating your writing skills through a polished, error-free cover letter and resume.

📅 Application Timeline

This position is open until filled. However, we recommend applying as soon as possible as roles at mission-driven organizations tend to fill quickly.

Typical hiring timeline:

1

Application Review

1-2 weeks

2

Initial Screening

Phone call or written assessment

3

Interviews

1-2 rounds, usually virtual

✓

Offer

Congratulations!

Ready to Apply?

Good luck with your application to Way to Win!

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