Director, Tax Clinic

Organizational Overview

Ladder Up is an entrepreneurial, Chicago-based nonprofit dedicated to providing free financial services to hardworking, low-income people. Through tax return preparation, college financial aid application assistance, financial education, and legal representation, Ladder Up helps clients access the resources they need to move up the economic ladder. Since 1994, Ladder Up has returned over $1.5 billion in life-changing dollars to hardworking families.

Position Summary

The Director of the Tax Clinic leads a dedicated team of attorneys, staff, interns, and volunteers who provide free legal representation and education to low-income clients facing disputes with the IRS or the Illinois Department of Revenue. The work is both technical and deeply human—helping individuals and families navigate complex tax challenges that can profoundly affect their financial stability and peace of mind.

This role is ideal for a mission-driven attorney who is passionate about social justice, economic mobility, and using the law to make a tangible difference in people’s lives. Ladder Up’s Tax Clinic is part of the IRS Low-Income Taxpayer Clinic (LITC) network and represents taxpayers who need to, among other things, defend audits, resolve identity theft, and file Innocent Spouse claims; the Tax Clinic also helps clients experiencing financial hardship explore collection alternatives available to them. . The Director ensures that the Tax Clinic delivers exceptional service, maintains compliance with IRS LITC guidelines, and continues to be a trusted resource for clients and partners alike.

Please note: Applicants must be an attorney licensed to practice law for at least three years. This is a strict requirement due to grant compliance. Candidates not meeting this requirement will not be considered. Bilingual (English/Spanish) candidates are strongly preferred.

Key Responsibilities

Leadership & Strategy

· Serve as a passionate and visible spokesperson for Ladder Up’s Tax Clinic, advocating for taxpayer rights and equitable treatment for low-income individuals and families.

· Lead, mentor, and support a team of staff attorneys, interns, and volunteers to deliver high-quality representation and outreach.

· Cultivate a collaborative and mission-centered team culture that values empathy, integrity, and professionalism.

· Stay current with developments in federal and Illinois tax law affecting low-income taxpayers, positioning Ladder Up to respond proactively.

· Participate as a member of the organization’s senior leadership team, contributing to cross-program strategy and impact measurement.

Tax Representation & Case Management

· Provide direct legal representation to clients in tax disputes, including but not limited to audits, collections, penalty abatements, and Tax Court proceedings.

· Supervise staff and pro bono attorneys and other tax professionals in managing caseloads and ensure compliance with IRS LITC standards.

· Conduct regular case reviews, ensuring consistency, quality, and adherence to deadlines.

· Maintain confidentiality and the highest ethical standards consistent with the Illinois Rules of Professional Conduct.

· Use case management software (Clio) to manage and report on caseloads, outcomes, and client demographics.

Program Operations

· Oversee day-to-day operations of the Tax Clinic, including client intake, volunteer coordination, and reporting.

· Collaborate across Ladder Up programs (Tax Assistance and Financial Capability) to strengthen referral pathways and ensure seamless client experiences.

· Lead the collection and analysis of data for internal evaluation, grant applications, and compliance reports.

· Ensure strong volunteer and intern engagement in partnership with the Volunteer Recruitment & Partnerships team.

Education & Outreach

· Oversee and expand community education initiatives that raise awareness and understanding of taxpayer rights and responsibilities.

· Deliver or supervise presentations to community organizations, legal aid partners, and other stakeholders on relevant tax law topics.

· Build and sustain partnerships with the IRS Taxpayer Advocate Service, other LITCs, law firms, and accounting partners.

External Engagement

· Represent Ladder Up publicly as an expert in low-income taxpayer issues and a champion for equitable tax policy.

· Attend the annual IRS LITC Conference as the designated Qualified Tax Expert.

· Collaborate with the Development team to provide data, success stories, and insights for donor engagement and reporting.

Qualifications

· Juris Doctor (J.D.) from an accredited law school.

· Licensed to practice law and in good standing for at least three (3) years – this is a required condition of employment.

· Minimum of 3+ years of relevant experience in tax law, legal aid, or public interest practice.

· Bilingual fluency (English/Spanish) strongly preferred.

· Demonstrated commitment to economic justice and experience working with low-income or marginalized populations.

· Exceptional client service and communication skills; patient, empathetic, and calm under pressure.

· Strong organizational and case management skills, including the ability to manage multiple priorities with attention to detail.

· Experience supervising attorneys, interns, or volunteers preferred.

· Proficiency in legal case management systems (e.g., Clio) and Microsoft Office Suite.

Compensation & Benefits

Salary Range: $90,000 – $105,000 (commensurate with experience) Health Benefits: Medical (BCBS), Dental, Vision Retirement: 401(k) with 3% employer match after 9 months Paid Time Off: 15 days annually + paid holidays Professional Development: Funding for CLEs, professional memberships, and annual IRS LITC Conference participation

How to Apply

Submit a resume and cover letter to info@goladderup.org with “Director, Tax Clinic” in the subject line. Applications will be reviewed on a rolling basis until the position is filled.

Job Type: Full-time

Pay: $90,000.00 - $105,000.00 per year

Benefits:

• 401(k)
• Dental insurance
• Health insurance
• Paid time off
• Vision insurance

Work Location: Hybrid remote in Chicago, IL 60654