Application Guide

How to Apply for Controller - Independent School Manager

at Breakwater Accounting + Advisory Corp

🏢 About Breakwater Accounting + Advisory Corp

Breakwater Accounting + Advisory Corp is a woman-led, four-time Top Workplace and Inc. 5000 fastest-growing company that provides outsourced accounting services to small businesses and nonprofits. They offer a fully remote, flexible work environment with a focus on strategic advisory rather than just bookkeeping, making them a unique place for experienced controllers who want to act as trusted advisors.

About This Role

As a Controller for Independent Schools, you will serve as the strategic financial advisor for 10-20 small to mid-sized independent schools or nonprofits, preparing high-level insights for Boards and Finance Committees. This role goes beyond traditional accounting—you'll lead monthly and quarterly conversations that turn financial data into actionable strategies, identifying risks and opportunities to guide client decisions.

💡 A Day in the Life

A typical day might start with reviewing client financials and preparing for a virtual meeting with a school's finance committee, where you present monthly insights and strategic recommendations. You'll then spend time on client calls, addressing ad-hoc questions from school administrators, and wrapping up with internal team check-ins to ensure all portfolio clients are on track.

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Interview Prep

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🎯 Who Breakwater Accounting + Advisory Corp Is Looking For

  • A seasoned accounting professional with 5+ years of progressive experience specifically in Independent Schools, including client advisory services (CAS) or as an Assistant Controller/Controller.
  • Proficient with student billing platforms like Veracross or FACTS, and comfortable translating financial data into strategic insights for non-financial stakeholders.
  • Exceptional communicator who can present to Boards and Finance Committees with clarity and confidence, acting as a trusted advisor rather than just a number-cruncher.
  • Self-starter comfortable with remote work, managing a portfolio of 10-20 clients, and prioritizing multiple deadlines in a fast-paced environment.

📝 Tips for Applying to Breakwater Accounting + Advisory Corp

1

Highlight your specific independent school experience in your resume, including the names of schools you've worked with and your role in student billing or board presentations.

2

In your cover letter, mention any experience with Veracross or FACTS explicitly, as these are strongly preferred.

3

Tailor your application to emphasize advisory and strategic thinking—use phrases like 'trusted advisor' and 'financial insights' to mirror the job description.

4

Include metrics or examples of how you've improved financial processes or identified risks for schools in past roles.

5

Research Breakwater's culture (Top Workplace, woman-led) and mention why that appeals to you in your cover letter or interview.

✉️ What to Emphasize in Your Cover Letter

['Your deep experience with independent school accounting and student billing platforms (Veracross/FACTS).', 'Your ability to present complex financial information to Boards and non-financial stakeholders in a clear, actionable way.', 'Your track record of acting as a strategic advisor, not just a controller—identifying opportunities and risks.', "Why you're excited about remote work and managing a diverse portfolio of schools/nonprofits."]

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🔍 Research Before Applying

To stand out, make sure you've researched:

  • → Review Breakwater's website and blog to understand their advisory approach and client success stories.
  • → Look up their Inc. 5000 and Top Workplace awards to understand their growth and culture.
  • → Check LinkedIn for current employees in similar roles to see their backgrounds and common career paths.
  • → Research the specific challenges independent schools face financially (e.g., enrollment fluctuations, tuition dependency) to show insight in interviews.
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💬 Prepare for These Interview Topics

Based on this role, you may be asked about:

1 Walk me through how you would prepare for and lead a quarterly financial review with a school's Finance Committee.
2 Describe a time you identified a financial risk or opportunity for an independent school and how you communicated it to leadership.
3 How do you prioritize and manage your workload when juggling 10-20 clients with different reporting cycles?
4 What experience do you have with student billing platforms like Veracross or FACTS, and how have you used them to improve processes?
5 Why do you want to work for a woman-led company like Breakwater, and how does our remote culture fit your work style?
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⚠️ Common Mistakes to Avoid

  • Do not submit a generic application that lacks specific independent school experience—this role requires it.
  • Avoid focusing solely on technical accounting skills; emphasize advisory and communication abilities.
  • Don't overlook the importance of student billing platforms—if you lack experience, acknowledge it and show willingness to learn quickly.

📅 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 Breakwater Accounting + Advisory Corp!

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