Director of Operations (Tax Industry)

Job Description

Description:

Milestone Tax Solutions is a fast-growing startup providing IRS tax resolution services for its clients. We’re dedicated to helping individuals get a fresh start by resolving their tax challenges efficiently and empathetically. Our innovative approach combines technology, creativity, and personalized service to guide clients back to financial stability.

We’re building a team of driven professionals who thrive in a dynamic, entrepreneurial environment. If you’re an experienced enrolled agent who is passionate about problem-solving, eager to make an impact, and ready to shape the future of tax resolution, we’d love to hear from you!

Job Summary:

We are seeking a proactive and experienced Director of Operations to oversee and optimize the daily functions of our growing Tax Resolution firm. This role is responsible for ensuring operational efficiency across multiple departments—including client intake, compliance, case management, tax resolution, and customer success. The ideal candidate will drive results through process improvement, team leadership, regulatory compliance, and alignment with company goals.

This is a high-impact leadership position for someone who thrives in a fast-paced, client-focused environment and understands the nuances of working with the IRS and resolving complex tax issues.

Responsibilities:

Strategic Leadership & Process Optimization

Lead day-to-day operations across all departments, ensuring workflow efficiency and high-quality client service.

Design, implement, and optimize scalable operational processes that support compliance and resolution timelines.

Establish and track KPIs to drive performance, productivity, and client satisfaction.

Collaborate with leadership to align operations with long-term business strategy.

Team Management & Development

Hire, manage, and mentor departmental managers (e.g., Compliance, Client Intake, Tax Prep, Sales, and Customer Service).

Foster a culture of accountability, collaboration, and continuous improvement.

Provide training and development to enhance team performance and engagement.

Compliance & Risk Management

Ensure all IRS submissions (Forms 2848, 8821) and processes meet federal regulatory standards.

Oversee the handling of IRS transcripts, case monitoring, and communication procedures.

Implement audit-ready documentation practices and oversee quality control systems.

Client Experience & Case Progression

Ensure timely movement of clients through each phase of the resolution process.

Monitor bottlenecks and proactively address issues affecting service delivery.

Work closely with the resolution team to expedite resolution timelines and improve outcomes.

Technology & Tools

Oversee the implementation and usage of platforms such as:

Tax Help Software (THS)

CRM systems

Case management software

Evaluate technology tools for process automation and efficiency gains.

Cross-Departmental Collaboration

Partner with Sales, Marketing, and Finance to align operational goals with company growth targets.

Act as a liaison between executive leadership and functional teams.Requirements:

5+ years in operational leadership, preferably in tax, legal, financial services, or a regulated industry.

Deep understanding of tax resolution processes, IRS protocols, and client compliance needs.

Proven experience in scaling operations, managing teams, and optimizing workflows.

Strong analytical, problem-solving, and project management skills.

Excellent communication and interpersonal abilities.

Experience with Tax Help Software, CRM systems, and reporting tools is a plus.

Bachelor's degree required; MBA or related advanced degree preferred.

Physical Requirements:

Prolonged periods sitting at a desk and working on a computer.

Legacy Capital Services is an Equal Opportunity Employer. We are committed to creating a diverse and inclusive workplace and do not discriminate based on race, color, religion, sex (including pregnancy, gender identity, and sexual orientation), national origin, age, disability, genetic information, veteran status, or any other protected characteristic as outlined by federal, state, or local laws.

Full-time