Application Guide

How to Apply for Managing Director - Chicago

at Compass Pro Bono

🏢 About Compass Pro Bono

Compass Pro Bono uniquely bridges the gap between local nonprofits and business professionals, fostering community resilience through pro bono consulting, board matching, and leadership summits. Working here means directly empowering nonprofits with strategic resources while leveraging business acumen for social impact.

About This Role

As Managing Director, you'll lead the Chicago market, driving growth and impact by building relationships with nonprofits and corporate partners. You'll oversee pro bono projects, manage a team, and ensure operational excellence, making a tangible difference in community equity.

💡 A Day in the Life

Your day might start with a call with a corporate partner to explore a pro bono project, followed by a team check-in on active consulting engagements. Afternoon could involve meeting with a nonprofit executive to assess their needs, then strategizing on fundraising or board recruitment. Evenings may include networking events or preparing for the annual leadership summit.

🚀 Application Tools

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Interview Prep

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🎯 Who Compass Pro Bono Is Looking For

  • 10-15 years of experience as a nonprofit executive, corporate leader, relationship manager, or fundraiser, with strong preference for nonprofit fundraising background.
  • Entrepreneurial mindset with ability to think strategically and execute hands-on, balancing big-picture vision with day-to-day operations.
  • Proven track record in building and managing cross-sector partnerships, especially between nonprofits and businesses.
  • MBA or comparable graduate degree preferred, with exceptional communication and leadership skills.

📝 Tips for Applying to Compass Pro Bono

1

Highlight your specific experience in nonprofit fundraising or pro bono consulting, quantifying impact (e.g., dollars raised, projects led).

2

Tailor your resume to emphasize relationship management and partnership development, especially with corporate and nonprofit stakeholders.

3

In your cover letter, mention familiarity with Compass Pro Bono's mission and programs, showing genuine alignment with their values.

4

Prepare a brief example of a time you led a cross-sector initiative, detailing challenges and outcomes.

5

Network with current or former Compass staff on LinkedIn to gain insights and mention your connection in the application.

✉️ What to Emphasize in Your Cover Letter

['Your passion for connecting business and nonprofit sectors to build equitable communities.', 'Concrete examples of fundraising success or pro bono project leadership with measurable results.', 'Your entrepreneurial drive and ability to operate in a lean, impact-focused organization.', 'Understanding of the Chicago nonprofit landscape and how you can leverage local relationships.']

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🔍 Research Before Applying

To stand out, make sure you've researched:

  • → Review Compass Pro Bono's current programs (consulting, board matching, summit) and recent success stories on their website.
  • → Look into the Chicago nonprofit ecosystem, including key players and challenges Compass addresses.
  • → Read about the organization's impact metrics and any news about their expansion or partnerships.
  • → Understand the pro bono consulting model and how Compass differentiates from competitors.
Visit Compass Pro Bono's Website →

💬 Prepare for These Interview Topics

Based on this role, you may be asked about:

1 How would you develop and maintain relationships with local nonprofits and corporate partners?
2 Describe a time you managed a complex project with multiple stakeholders; what was your approach?
3 How do you prioritize competing demands in a fast-paced, entrepreneurial environment?
4 What strategies have you used to raise funds or secure pro bono commitments?
5 How would you measure success in this role, and what metrics would you focus on?
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⚠️ Common Mistakes to Avoid

  • Submitting a generic application without mentioning Compass Pro Bono or the Chicago market specifically.
  • Focusing only on corporate experience without demonstrating understanding of nonprofit needs and fundraising.
  • Overlooking the entrepreneurial nature of the role; avoid expecting a structured corporate environment.

📅 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 Compass Pro Bono!

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