Payroll Assistant Remote Jobs in Bolingbrook, IL

519 Southwest Blvd, Kansas City, MO 64108, USA

This position is based in the Kansas City, MO area, and offers remote and hybrid work arrangements. Applicants should either currently reside in the Kansas City Metro area or plan to relocate to Kansas City.

e2E helps startups, small businesses, and nonprofits successfully grow to the next level by providing the strategic finance, human resources, payroll services, and/or tax expertise they need to succeed, freeing them to focus on the growth and profitability of their businesses.

To learn more about e2E, visit our website at www.e2ekc.com.

The Director of Tax serves as e2E's primary tax expert and a trusted advisor to client organizations, providing strategic and technical guidance across all areas of tax compliance, planning, and reporting. This is a hands-on role: the Director of Tax personally prepares some returns, reviews all returns, and remains directly involved in the technical work while owning the full tax function for assigned clients. Responsibilities include managing complex multi-entity, multi-state return preparation, engaging and overseeing an outsourced tax preparation resource to add capacity, and developing the internal processes and staff capabilities that ensure timely, accurate compliance across federal, state, and local jurisdictions. The Director of Tax partners closely with clients and internal teams to deliver proactive, high-quality tax solutions aligned with each client's business goals.

Essential Duties and Responsibilities 

• Own and manage the tax function for all assigned clients; communicate timelines, filing status, and tax preparation progress on a regular basis.
• Prepare tax workpapers and returns for Corporations, S Corporations, Partnerships, Individuals, Fiduciaries, Non-Profits, and Private Foundations, including complex and newly onboarded engagements.
• Contribute to complex entity proposals and newly onboarded engagements to ensure capacity and analyze whether there is a good fit to engage for tax services.
• Review returns prepared by internal staff and outsourced providers, remaining accountable for the accuracy of every filing that leaves the firm.
• Prepare and review quarterly estimated tax payments for individuals, pass through entities, and corporations.
• Deliver tax planning guidance and proactive compliance solutions, including identifying opportunities to reduce tax exposure and mitigate risk.
• Manage the Indirect Tax Consultant position responsible for developing and administering SALT (state and local tax) registration and compliance procedures, client delivery templates, and timely compliance outcomes. Serve as a resource to staff and clients for more complex scenarios requiring research or registration with applicable governmental entities at the federal, state, county, and city levels.
• Research and register clients with applicable governmental entities at the federal, state, county, and city levels to ensure timely compliance.
• Identify, engage, and manage an outsourced tax preparation resource to scale capacity defining scope and turnaround, coordinating engagement handoffs, and holding the provider accountable for quality and deadlines.
• Advise nonprofit clients on unrelated business taxable income (UBIT), exemption maintenance, and Form 990 governance disclosures.
• Assist clients with responses to agency notices.
• Monitor and interpret federal, state, and local tax legislation; proactively communicate changes and their impact to clients and e2E staff.
• Develop, document, and administer internal tax and compliance procedures to ensure consistent workflow management and deadline adherence.
• Design and facilitate tax training sessions for e2E staff on technical updates, compliance requirements, and best practices.
• Maintain effective communication with team members and client stakeholders, participating regularly in client calls and meetings.
• Collaborate with accounting, payroll, and HR teams to support seamless cross-functional client service.
• Perform other duties and client-related projects as assigned.

Minimum Requirements

• Bachelor's degree in accounting, finance, or a related discipline required.
• CPA certification required.
• 8+ years of tax preparation experience in a private or public accounting firm.
• Willingness and ability to serve as a current, hands-on preparer. This role requires direct preparation and review of tax returns rather than solely overseeing or delegating that work to others.
• Demonstrated experience advising on the tax implications of mergers and acquisitions, business transition transactions (e.g., ownership changes, succession planning, entity conversions), and review of operating agreements and other governing documents to identify tax-related provisions, risks, and planning opportunities.
• Demonstrated experience with a variety of tax compliance software and bookkeeping platforms.
• Proficiency in Microsoft Office Suite, document-sharing platforms, virtual collaboration tools, and emerging technologies (AI).

Knowledge, Skills, and Abilities 

• Deep technical knowledge of federal, state, and local tax law, including compliance requirements across multiple entity types and jurisdictions.
• Demonstrated experience researching technical tax matters and applying best practices in complex client scenarios.
• Ability to direct and quality-check outsourced preparers or third-party tax providers, or readiness to take that on, while remaining the primary preparer and reviewer.
• Excellent written and verbal communication skills; able to present recommendations to business owners, executives, and key stakeholders with clarity and professionalism.
• Strong client-service orientation with a commitment to responsiveness, accuracy, and building lasting relationships.
• Forward-thinking approach to technology and process improvement; comfortable leveraging tax automation tools and workflow platforms.
• Solid organizational and project management skills; proven ability to manage multiple concurrent client engagements with competing deadlines.
• High attention to detail with the ability to work at both strategic and tactical levels.
• Ability to handle sensitive and personal client information with discretion, confidentiality, and professionalism.
• Self-starter with a strong ownership mentality and comfort operating in an entrepreneurial, fast-paced environment.
• Collaborative team orientation with proven ability to work effectively across functions.

Benefits

• Competitive salary and performance-based bonuses.
• Comprehensive benefits package, including healthcare and retirement plans.
• Professional development opportunities and ongoing training.
• Collaborative and innovative work environment.
• Opportunity to work with diverse and exciting clients.
• Company culture that values creativity, initiative, and growth.

Additional Information: All offers are contingent on successful completion of a background screen.