Multi Offices - Paralegal, Employee Benefits & Compensation

Winston Taylor LLP; Chicago (IL); On-site; USD 70,000 - 110,000; Full time

Benefits offered by this job

Comprehensive benefits

Healthcare coverage

Job summary

Winston Taylor LLP is seeking an Employee Benefits & Executive Compensation Paralegal to support attorneys with benefits matters, regulatory compliance, and due diligence for transactions. The role involves document preparation, research, and matter coordination within a busy law firm environment.

The ideal candidate has a Bachelor's degree, at least two years of paralegal or benefits experience, and is able to work at least 3–4 days a week in the office, with strong writing, organizational,

Qualifications

• Bachelor's degree required.
• 2+ years of paralegal, legal, or related benefits support experience.
• Must live within commuting distance to a local office and be willing to come into the office 3-4 days per week.
• Experience with ERISA and IRS provisions.

Responsibilities

• Assist attorneys with employee benefits and executive compensation matters, including plan matters and regulatory compliance.
• Draft, proofread, review, redline, and revise legal documents and related materials under attorney supervision.
• Conduct legal, regulatory, and factual research concerning employee benefits, executive compensation, and plan administration.
• Assist with due diligence for mergers and acquisitions and other corporate matters involving benefit plans and compensation.
• Prepare and review plan documents, SPDs, summaries of modifications, and related materials.
• Coordinate with attorneys, clients, plan administrators, and third parties; maintain matter records.

Skills

Legal research

Drafting & editing

Attention to detail

Project management

Communication skills

Education

Bachelor’s degree

Paralegal certificate preferred

Tools

Westlaw

LexisNexis

Microsoft Office

Job description

About Us

At Winston Taylor, we set the standard, together. Winston Taylor is a transatlantic law firm built for the businesses, people, and markets driving capital and innovation. Here, you're in the room. In the action. Sleeves rolled up.

You'll work with leading clients. Disruptors. Fast-growth companies. And help them to stay one step ahead of the moment and make critical decisions that shape their future. We're present in the U.S., U.K., Europe, Latin America, and the Middle East, combining the scale and speed that clients demand.

You’ll be trusted with real responsibility from the outset and build experience through hands‑on work. We take your progression personally. We provide the platform. You shape the work around your goals and aspirations.

Step into the moments that matter. Join Winston Taylor.

Position Summary

Employee Benefits & Executive Compensation Paralegal provides substantive legal and administrative support to attorneys in connection with employee benefits, executive compensation, and related matters. The position assists with the preparation, review, organization, and maintenance of legal documents; conducts legal, regulatory, and factual research; supports due diligence and transaction-related activities; and coordinates matter management to facilitate the efficient delivery of legal services to clients. The role also supports routine employee benefits work and practice development initiatives under attorney supervision.

The ideal candidate is detail-oriented, highly organized, technology-forward, and capable of managing multiple priorities in a deadline-driven law firm environment. The candidate will demonstrate strong research, writing, analytical, communication, project management, and executive functioning skills, along with the ability to handle confidential client, employee, compensation, and benefits information with discretion.

Position Responsibilities

• Assist attorneys with employee benefits and executive compensation matters, including qualified retirement plans, health and welfare plans, deferred compensation arrangements, equity-based compensation, and related regulatory compliance.
• Draft, proofread, review, redline, compare, and revise legal documents, correspondence, memoranda, summaries, charts, reports, and other materials under attorney supervision.
• Conduct legal, regulatory, and factual research concerning employee benefits, executive compensation, plan administration, and applicable federal laws and regulations, including ERISA and relevant provisions of the Internal Revenue Code.
• Assist with due diligence for mergers and acquisitions, corporate transactions, reorganizations, and other business matters involving employee benefit plans and executive compensation arrangements.
• Assist with the preparation of document requests, due diligence reports, disclosure schedules, and summaries of employee benefit plan and executive compensation information.
• Assist with the preparation and review of plan documents, summary plan descriptions, summaries of material modifications, plan amendments, employee benefit policies, participant communications, and related materials.
• Perform and coordinate routine employee benefits work, including beneficiary designation and related document review, recurring participant communications, government forms and filings, and routine plan amendment drafting, subject to attorney review.
• Support the preparation, submission, and tracking of applicable regulatory filings and government forms with the U.S. Department of Labor and Internal Revenue Service, including matters under the EPCRS and VFCP programs, under attorney supervision.
• Assist with qualified domestic relations order review and certification, including maintaining matter files and tracking outstanding items.
• Assist with the preparation of IRS determination letter submissions, private letter ruling requests, and related supporting materials.
• Prepare, review, and revise health and welfare plan materials, including Summaries of Benefits and Coverage and related compliance documentation.
• Organize, review, and maintain electronic and hard-copy files, transaction documents, and supporting materials.
• Track deadlines, filing requirements, document execution, compliance calendars, and other matter-related milestones; identify outstanding items and communicate status to the matter team.
• Coordinate with attorneys, clients, opposing counsel, plan administrators, benefits consultants, governmental agencies, service providers, and other third parties as directed.
• Maintain accurate matter records and ensure documents are properly named, organized, and retained in accordance with firm procedures.
• Apply strong project management and executive functioning skills to plan and sequence work, manage competing priorities, identify dependencies, maintain deadlines, and move assignments through completion.
• Support non-billable practice development activities, including researching and preparing blog posts, client alerts, presentations, and first drafts of other client-facing and internal materials.
• Handle sensitive and confidential client, employee, compensation, and benefits information appropriately.
• Perform additional duties and special projects as assigned.
• Be familiar with and utilize available technology, including firm-approved AI tools, to support document review, drafting, research, workflow management, and process improvement in accordance with firm policies, attorney direction, and confidentiality requirements.
• Work additional hours, with little notice, and may require more than 35 hours per week to perform the essential duties of the position; may also require irregular hours.
• Follow the ethical requirements set forth by the applicable Rules of Professional Conduct.

Experience, Skills, And Qualifications

• Bachelor’s Degree required; paralegal certificate preferred.
• 2+ years of experience providing paralegal, legal, or related benefits support in a law firm, corporate legal department, employee benefits practice, or comparable professional environment required.
• Candidate must live within a commutable distance to a local office and be willing to come into the office 3-4 days per week.
• Experience supporting an employee benefits, executive compensation, tax, corporate, or ERISA practice.
• Familiarity with ERISA, the Internal Revenue Code, qualified retirement plans, health and welfare plans, and executive compensation arrangements.
• Experience assisting with transactional due diligence, mergers and acquisitions, or corporate reorganizations.
• Experience conducting legal research using Westlaw, LexisNexis, or similar research platforms.
• Familiarity with legal document management systems and electronic transaction platforms.
• Strong written and verbal communication skills, including the ability to proofread and prepare accurate, professional documents.
• Excellent attention to detail, organizational skills, and ability to manage competing priorities and deadlines.
• Strong project management and executive functioning skills, including planning, prioritization, organization, follow-through, time management, adaptability, and accuracy across multiple concurrent workstreams.
• Strong technology skills and demonstrated ability to learn and use new systems and tools, including approved artificial intelligence tools.
• Proficiency in Microsoft Office applications, including Word, Excel, Outlook, and PowerPoint.
• Ability to handle confidential information with sound judgment and discretion.
• Demonstrated ability to work independently while collaborating effectively with attorneys and other professionals.

Benefits

Winston offers comprehensive benefits that provide a full spectrum of coverage and support for our full-time employees and their families. Additional information about benefits and rewards can be found here.

Salary

The target annual salary range for this role is currently $70,000-$110,000 based on a regular, full-time schedule. The amount of compensation offered will be determined by several factors, including but not limited to experience, qualifications, market data and internal equity. Total compensation includes a comprehensive healthcare benefits package, yearly retirement contribution, and may include an annual discretionary merit bonus.

We are an equal opportunity employer and welcome applicants from all backgrounds and experiences.