Application Guide

How to Apply for Billing Assistant (part-time) at Law Firm Exclusively Serving Nonprofit/Tax-Exempt Organizations

at Cheshire Law Group

🏢 About Cheshire Law Group

Cheshire Law Group is an award-winning, woman-owned law firm that exclusively serves nonprofit and tax-exempt organizations as outside general counsel. With 15 years of experience, they provide sophisticated legal counsel at affordable rates, believing nonprofits deserve the same expertise as for-profits. Their commitment to collaboration, systemic problem-solving, and community strengthening makes them a unique and mission-driven employer.

About This Role

As a part-time Billing Assistant, you'll be responsible for the monthly billing cycle, including proofreading, coordinating attorney review, editing, and sending a high volume of invoices during the first two weeks of each month. You'll also monitor client billing communications, resolve billing questions, and generate accounts receivable aging reports. This role is critical to ensuring the firm's financial health and maintaining strong client relationships.

💡 A Day in the Life

A typical day during the first two weeks of the month might involve reviewing and editing a batch of invoices, coordinating with attorneys for approvals, sending invoices to clients, and responding to billing inquiries. Later in the month, you might focus on generating accounts receivable reports and following up on outstanding payments. The role is remote, so you'll communicate with the team via email or virtual meetings.

🎯 Who Cheshire Law Group Is Looking For

  • Exceptional attention to detail and proofreading skills, with the ability to catch errors in invoices and billing communications.
  • Experience in billing, accounting, or a related field, preferably in a law firm or professional services environment.
  • Strong communication skills to interact professionally with attorneys and clients, resolving billing inquiries promptly.
  • Ability to work independently in a remote setting and manage time effectively, especially during the high-volume first two weeks of each month.

📝 Tips for Applying to Cheshire Law Group

1

Highlight any experience with legal billing software or accounting systems, as the firm likely uses specialized tools for invoicing and accounts receivable.

2

Emphasize your ability to handle a high volume of detailed work under tight deadlines, particularly during the first two weeks of the month.

3

Demonstrate familiarity with nonprofit organizations or a passion for the nonprofit sector, as the firm exclusively serves these clients.

4

Mention your remote work experience and ability to collaborate effectively with a distributed team.

5

Reference the firm's mission or recent client testimonials in your application to show genuine interest in their work.

✉️ What to Emphasize in Your Cover Letter

In your cover letter, focus on your detail-oriented approach to billing and proofreading, your experience with high-volume invoice processing, your ability to communicate effectively with clients and attorneys about billing matters, and your interest in supporting a mission-driven law firm that serves nonprofits.

Generate Cover Letter →

🔍 Research Before Applying

To stand out, make sure you've researched:

  • Visit the Cheshire Law Group website to learn about their practice areas, values, and the types of nonprofit clients they serve.
  • Read client testimonials to understand the firm's reputation and the importance of client service in their billing process.
  • Research common billing practices in law firms, especially those serving nonprofits, to speak knowledgeably about the role.
  • Look up the firm's leadership and recent news to understand their growth and culture.
Visit Cheshire Law Group's Website →

💬 Prepare for These Interview Topics

Based on this role, you may be asked about:

1 Your experience with billing software and how you ensure accuracy in invoice preparation.
2 How you prioritize tasks during the high-volume first two weeks of the month.
3 A time you resolved a billing discrepancy or difficult client inquiry.
4 Your understanding of the nonprofit sector and why you want to work with nonprofit clients.
5 How you handle confidential information and maintain professionalism in a remote environment.
Practice Interview Questions →

⚠️ Common Mistakes to Avoid

  • Avoid generic cover letters that don't mention the firm's nonprofit focus or the specific billing responsibilities.
  • Don't neglect to proofread your application materials, as attention to detail is crucial for this role.
  • Avoid implying that you can only work during certain hours without acknowledging the need for flexibility during the first two weeks of each month.

📅 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 Cheshire Law Group!