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Our employment and benefits practitioners bring decades of experience in helping our clients manage human resources most productively, with an emphasis on "preventive maintenance" and litigation avoidance, design and support benefit arrangements that serve the broad needs of their employee base, and address the unique needs of their executive suite and boards.

Skilled practitioners in the highly regulated world of employment and benefits, our practitioners regularly provide the type of pragmatic support our clients need.  With a client base that ranges from the sole proprietor and small businesses to public companies and established financial institutions and service businesses with thousands of employees and offices worldwide, Sullivan’s employment and benefits specialists can support your business objectives.

Employment & Benefits Practice Areas

Employment Counseling & Litigation

Compensation & Benefits Plan Design and Administration

Executive Compensation

ERISA Fiduciary

Accolades

  • The 2024 edition of Chambers USA recognized the Employee Benefits and Executive Compensation Group and noted the breadth of its capabilities in employee benefits matters and for its representation of a range of corporate and individual clients, particularly in the financial services industry. The group is singled out for its expertise in tax implications and considerations of benefit plans, M&A-related matters and compensation arrangements.
  • 2025 Best Lawyers, Best Law Firms® ranked the group in Employee Benefits (ERISA) Law
  • The 2025 edition of The Legal 500 United States ranked the group in Employee Benefits, Executive Compensation and Retirement Plans: Design
  • The 2025 edition of Chambers USA recognized the Employee Benefits and Executive Compensation Group, praising its deep bench of lawyers and its ability to assemble teams with the specialized knowledge needed to address a wide range of complex issues

Useful Resources

Regulatory Compliance Checklist - Employment and Workplace Policies

Regulatory Compliance Checklist - Benefits

Viewpoints
All Viewpoints
Hiring: Add a Colleague, Not a Liability
Hiring a new employee is typically a moment of optimism—and sometimes, the relationship really does go wonderfully for its entire length and ultimately ends on good terms. But when that hope is treated as an assumption, companies make themselves vulnerable. If a client-facing employee does not have a non-solicitation agreement, a business’s customers could be poached. A new employee, hired because of their great industry relationships, might actually have an undisclosed non-compete or non-solicit with a competitor—and suddenly, your business is being sued. Strong contracts are an essential part of protecting the business against unexpected outcomes. ​Using Contracts to Protect Business Assets By requiring upfront agreement on boundaries to protect the business—such as agreements regarding non-solicitation, non-competition, confidentiality, invention assignment, and non-disparagement—a business both discourages disloyalty in the first place and has ammunition if an employee later crosses the line. Companies often invest substantial resources into relationships, whether with employees or with business partners, but these relationships can be vulnerable to poaching. For example, an employee may look effective and helpful to customers because of institutional support that costs the business time and money, but which is invisible to the customer, who assumes the individual employee deserves all credit. A non-solicitation agreement bars a former employee from trying to ​hire the company’s employees and/or from trying to do business with the company's clients for a fixed period of time after the relationship ends. This protects the company's investment in those relationships. Most businesses depend on information that they would not want a competitor to have. If a confidentiality agreement is not written clearly enough, it might turn out to be a picket fence where barbed wire is needed. Confidential information is not just cutting-edge scientific research—it can also include hard-won insight into specific customer preferences, proprietary analysis of market trends, and much more. New hires who are likely to be given access to confidential information should generally be required to sign a confidentiality agreement that firmly protects the business’s informational assets. A confidentiality agreement needs to appropriately define the confidential information being protected and the expectations on the employee (such as not disclosing that information or using it outside non-disclosure and return of information at the end of employment). Similarly, invention assignment agreements ensure that the employee’s ideas—particularly those in line with the company’s own business, research, or development—belong to the business. This prevents employees from collecting a salary while developing ideas that would be valuable to the business—but keeping those ideas to themselves, possibly to use in competition against the business. Non-solicitation and confidentiality agreements are important, but they can be difficult to enforce in time to prevent damage. A business often will not know that confidential information was given away or misused until it is much too late to the put the horse back in the barn. A non-competition agreement prevents a former employee from competing against the business for a fixed amount of time. Especially when a former employee has had access to confidential information and to valuable business relationships, this can be a valuable for tool for avoiding misbehavior. If an employee cannot work for a competitor at all, they are less likely to be in situations where they might violate other restrictions. Finally, a non-disparagement agreement protects the company’s reputation. However, some employees may balk at agreeing to this upfront, before the relationship has even begun. Companies should consider whether a non-disparagement agreement is a term worth including as a hiring requirement. As with most employment terms, a company may decide that this term will be included for certain hires, but not all. Agreements should match the specific needs of each employment situation; to be enforced, it is essential that they also match state law. State employment laws vary substantially. One state may require that a confidentiality agreement have an exception for sexual harassment; another may require certain carve-outs to invention assignment agreements; a third may impose an annual compensation minimum for non-solicitation agreements; a fourth may require that employees are told of their right to consult with counsel before signing a non-competition agreement. An agreement that does not comply with applicable state law might not be enforceable, which means the company does not have the protection it thought it had. In some cases, a noncompliant contract raises additional issues: for example, in California, non-competition agreements are banned in most circumstances, and businesses face a penalty if they require an employee to sign one. Businesses should work with counsel on agreements that are appropriate to each circumstance and applicable state and federal law. Hiring from Competitors Conversely, businesses often hire people who have worked in the field before—perhaps even at a competitor. Even though the business didn't sign the employee’s prior employment agreement and is not a party to it, when a former employee breaches a contract to benefit a competitor, the competitor is typically sued alongside the employee.[1] Upfront preparation can reduce risks. When hiring a new employee, a business may require the employee to confirm (as a written requirement of employment) that this job will not conflict with any other contractual commitments of that employee. If the employee raises a concern about another contract, the business should review the contract with counsel. In some instances, there may be an argument that the contract is not enforceable, and the employee and the business will each need to decide whether they are willing to take a risk. In some instances, there may be a confidentiality or non-solicitation restriction but no non-compete. In those cases, although employment is allowed, the former employer will likely be suspicious and may sue. When there are confidentiality and non-solicitation restrictions, businesses should strongly consider instructing the employee not to engage in any conduct that would violate those restrictions, and it may choose to be even more proactive by keeping the employee siloed from the customers or parts of the business that raise the contractual risk. Those protections can often be time-limited, such as to the amount of time remaining on a non-solicitation agreement. ​When ​a former employee does not have any prior agreement, a company has much more flexibility, but risks still exist. For example, the federal Defend Trade Secrets Act allows a business to sue for misappropriation of trade secrets, and a former employer may allege that a company misappropriated its trade secrets through the departed employee. Companies can reduce risks by providing instructions to employees that they should not use or disclose confidential information from any other business in their work. Requiring Commitment Employees sometimes engage in outside work. Guardrails set important expectations and give the business a clear exit ramp if an employee breaks the rules. For some positions, it may be appropriate to restrict all outside work. Most businesses would not want their CEO to be managing another business on the side. In those cases, requirements that an employee to devote their full business efforts to the position, and not to engage in outside work, makes the expectation both clear and firm. In other situations, outside work may be appropriate; additionally, some states have pro-moonlighting laws that protect employees’ off-hours activities. In those cases, agreements or policies create a moat of protection around the business. Businesses can set expectations around not participating in moonlighting during working hours, not using the business’s equipment for an outside venture, and similar issues. Conclusion By establishing clear rules up-front, a business encourages the right type of behavior from the beginning, and it is better able to defend itself against attacks from current and former employees—often the people who best know its vulnerabilities and its proprietary secrets. [1] Whether the former employer’s claim against the new employer is strong, or even viable at all, are different questions and depend on many factors, including specific facts and state law. But even an unsuccessful claim can force expensive defense costs and distractions from the business.   Further resource: Listen to Erika Todd discuss legal concerns for freelancers with fulltime jobs on The Freelance Mindset Studio podcast here. Coming up: The next article in this series will discuss key issues to know about creating incentive compensation plans—including the risks of a casual or ambiguous arrangements and triggers for tax penalties. This article is not legal advice. If you are interested in discussing any of these topics further, please contact a member of the Employment & Benefits Practice Group.
Erika Todd Featured on Podcast Discussing the Legal Risks of Freelancing While Employed
Erika Todd was recently featured on The FreeLance Mindset Studio Podcast with host Joy Batra in an episode titled, “The Hidden Legal Risks of Side Hustles.” During the conversation, Erika discussed legal considerations for professionals to keep in mind when balancing a full-time job with a side business. Topics covered included key agreement and policy language that affect employees’ rights (such as invention assignment agreements and restrictions on outside work); state law differences in the legal protections available to freelance workers; and navigating discussions with a primary employer about a side venture. You can access the episode on all platforms here.
Top Tier Firm, Legal 500 United States 2026
Sullivan & Worcester Ranked in the Legal 500 United States 2026 Edition
Boston, MA – Sullivan & Worcester announced that its practice groups and attorneys have been ranked and recommended in the Legal 500 United States 2026. The firm’s Real Estate practice was newly ranked Tier 1 in the “Real estate – mid-market ($0-500m)” category and the firm maintained rankings across a variety of practice areas. Partners Nicole Crum and John Steiner were newly ranked as Leading Partners and Ryan Rosenblatt as a Next Generation Partner. Peers and more than 300,000 corporate counsel were surveyed and interviewed globally in the past 12 months to assess law firms’ overall visibility and reputation, culminating in detailed rankings and editorial. The Legal 500 is an independent guide, and firms and individuals are recommended purely on merit. Sullivan's lawyers received the following rankings: Leading Partners: The Legal 500’s Guide to Outstanding Lawyers Nationwide Benjamin Armour - M&A: Middle-Market (Sub-$500m); M&A: middle-market ($0-250m) Ameek Ashok Ponda - Real Estate Investment Trusts (REITs)  Nicole Crum - Mutual/registered/exchange-traded funds Lewis Segall - M&A: Middle-Market (Sub-$500m); M&A: middle-market ($0-250m) John Steiner - Real estate – mid-market ($0-500m) Douglas Stransky - International Tax Joel Telpner - Fintech Next Generation Partners: The Legal 500’s Guide to Up-and-Coming Lawyers Nationwide Ryan Rosenblatt - General commercial disputes – mid-market ($250-500m) Sarah Wellings - Real Estate Investment Trusts (REITs) Practice Areas Ranked and Attorneys Recognized Corporate Governance “Our lead partner, Nicole Crum, who leads the investment industry practice, is exceptional. She demonstrates strong industry knowledge yet is very personable and anticipates what we need to know or what we should consider doing to handle any matter. The team roll up their sleeves and provide recommendations as to how we as a board should handle any matter. Strong service commitment and work ethic!” “The team we have at Sullivan & Worcester has served our company for years and knows the management team, staff as well as our board members. They are extremely responsive and proactive and anticipate what we should be aware of, concerned about, excited about, and how to handle oversight, processes and protocols to ensure we are carrying out our fiduciary duties. The partners are experts in this industry.” Leading Partner: Nicole Crum Recommended Lawyers: Howard Berkenblit, David Leahy Dispute Resolution/General Commercial Disputes “Diverse skillset. Client centric. Transparency. Urgency provided on all matters.” “I have worked with Gerry Silver for over 15 years and have found his pragmatic approach to complex matters refreshing. He understands our business, culture and market, and will give me his opinion in a digestible manner.” Next Generation Partner: Ryan Rosenblatt Recommended Lawyers: Gerry Silver, Patrick Dinardo, Laura Steinberg, Michael Sullivan, Amy Zuccarello, Erika Todd, Christopher Shields, Anna Lea McNerney Employee Benefits, Executive Compensation and Retirement Plans: Design “The level of expertise is top shelf. David Guadagnoli seems to know all of ERISA and IRS rulings.” “David Guadagnoli and Amy Sheridan both have superior knowledge in their respective areas. I value the ability to raise issues whether simple or complex. The firm takes the same diligent approach across all spectrums of complexity.” Recommended Lawyers: David Guadagnoli, Amy Sheridan Environment: Transactional Fintech “Sullivan & Worcester is one of the finest firms with which I have worked.” “The lawyers are excellent, and the firm consistently provides the highest quality of customer service.” Leading Partner: Joel Telpner Recommended Lawyers: Natalie Lederman, Benjamin Armour, Scott Kaufman, Harvey Bines, Christopher Curtis Land Use/Zoning Recommended Lawyers: Gregory Sampson, Ashley Brooks, Victor Baltera, Karen Kepler, Ashley Tan M&A: Corporate and Commercial: Venture Capital and Emerging Companies Recommended Lawyers: Scott Kaufman, Lewis Segall, Benjamin Armour, Michael Student M&A: Middle-Market ($0-250m) “The partner Lewis Segall has been working with our company for 15 years and we have a good working relationship with him. He knows our history and very attentive to our needs.” “Lewis Segall is very attentive to our needs. We very much value him.” Leading Partners: Benjamin Armour, Lewis Segall Recommended Lawyers: Natalie Lederman Mutual/Registered/Exchange-Traded Funds “Sullivan & Worcester's practice is defined by its deep expertise in investment funds and its ability to deliver clear, commercially grounded advice across the full fund lifecycle—from formation and structuring to regulatory compliance and complex transactions.” “The team is highly experienced, collaborative, and excel in efficient execution and clear communication.” Leading Partner: Nicole Crum Recommended Lawyers: David Leahy, David Mahaffey, Rachael Schwartz Real Estate Leading Partner: John Steiner Recommended Lawyers: Ashley Brooks, Karen Kepler, Gregory Sampson, Sharon Leifer, Louis Monti, Spencer Stone, Ashley Tan Real Estate Investment Trusts (REITs) “We have built multiple complex and sophisticated REIT platforms over the years and worked with many top-tier REIT specialists, but Sullivan’s REIT practice is by far the best, with Sarah Wellings.” Leading Partner: Ameek Ashok Ponda Next Generation Partner: Sarah Wellings Recommended Lawyers: Angela Gomes, Louis Monti, Shu Wei, Cameron Cosby International Tax “The international collaboration with S&W is exceptional.” “What really stands out is their willingness to engage, openness to different ideas and opinions, clearly expressed expectations, and clients' objectives.” Leading Partner: Douglas Stransky Recommended Lawyers: Lewis Greenwald, Eric Rietveld Tax > US Taxes: Contentious Recommended Lawyers: Richard Jones, David Nagle, Daniel Ryan, Caroline Kupiec Tax > US Taxes: Non-Contentious “Sarah Wellings is, quite simply, the best lawyer we have ever worked with. Her expertise extends far beyond tax and REIT matters, encompassing governance, financing, and complex commercial issues. Decades of experience and technical mastery make her an indispensable partner. Sarah is our central point of contact who makes everything seamless. Her in-house counsel background gives her a unique client perspective: she anticipates needs, solves problems before they arise, and delivers concise, well-structured updates that simplify even the most intricate issues. She coordinates effortlessly with all parties involved. Her judgment is exceptional. Sarah strikes the perfect balance between comprehensive academic rigor and practical, business-oriented advice. She combines technical REIT/tax excellence with commercial instincts, ensuring every recommendation is both legally sound and strategically smart. Her ability to translate complex law into clear, actionable guidance is unmatched. Sarah is incredibly responsive without ever sacrificing quality. She treats our matters as her own, demonstrating a rare ownership mindset and collaborative spirit. Her integrity is uncompromising, giving us absolute confidence in her counsel. In short, Sarah Wellings defines legal excellence: reliable, commercially minded, and client-focused. Working with her feels like being in the safest possible hands; she consistently exceeds expectations and orchestrates complex transactions with clarity and precision.” Recommended Lawyers: Ameek Ashok Ponda, Richard Jones, Douglas Stransky, Sarah Wellings About Sullivan Sullivan & Worcester (Sullivan) is a premier international law firm with lawyers in Boston, London, New York, Tel Aviv and Washington, D.C. Sullivan’s clients, including Fortune 500 companies, leading financial services firms and asset managers, boards of directors, real estate companies, and emerging businesses, rely on Sullivan’s ability to navigate complex legal and operational landscapes, the impeccable judgment of its lawyers, and its commitment to best-in-class client service.
Sullivan & Worcester Ranked in Chambers USA 2026 Edition
Boston, MA – Sullivan & Worcester announced that its practice groups and attorneys have been highly ranked by Chambers USA in its annual rankings of the foremost law firms and attorneys in the country. In the 2026 guide, the firm is newly ranked in Banking & Finance in Massachusetts and partner Will Hanson is newly ranked in Private Equity: Fund Formation in Massachusetts. Partner Ameek Ashok Ponda retained a Band 1 nationwide ranking for REITs: Tax and a Band 1 ranking in Massachusetts for Tax. Partner Cameron Cosby retained a Band 1 nationwide ranking for REITs: Tax. Partners Amy Sheridan and David Guadagnoli retained Band 1 rankings in Massachusetts for Employee Benefits & Executive Compensation. Partner Stephanie Monaco retained a Band 1 ranking nationwide in Investment Funds: Regulatory & Compliance. The Chambers USA guide ranks firms and attorneys annually based on in-depth research, as well as client and peer interviews. Chambers evaluates attorneys based on their legal knowledge and experience, ability and effectiveness, and client service. Sullivan Practice Group Nationwide Rankings Registered Funds REITs Sullivan Practice Group Regional Rankings Banking & Finance (Massachusetts) Bankruptcy/Restructuring (Massachusetts) Employee Benefits & Executive Compensation (Massachusetts) Litigation: General Commercial (Massachusetts) Real Estate (Massachusetts) Tax (Massachusetts) Individual Rankings/Client Comments Ashley Brooks – Real Estate (Massachusetts). “Ashley Brooks has a burgeoning Boston-based real estate practice. She routinely assists with matters pertaining to acquisitions and developments. She often works on mixed-use residential and retail projects.” "Ashley has done an excellent job of building Sullivan & Worcester's practice as well as her own reputation and quality of work." Cameron Cosby – REITs: Tax (Nationwide). “Cameron Cosby is commended for his strength across the REIT tax space, with notable experience of formations, M&A and debt and equity offerings.” "He is one of the most well-respected REIT tax lawyers. Cam's decades of experience advising REITs in all asset classes makes him unique among REIT tax lawyers. He is able to navigate complex and contentious transactions with no drama." David Guadagnoli – Employee Benefits & Executive Compensation (Massachusetts). “David Guadagnoli is an accomplished employee benefits practitioner, with notable expertise on the tax aspects of retirement plans and welfare benefits. He is also known for negotiating employment and severance agreements.” "His knowledge and ability to communicate that knowledge is the best I have come across during my years." Will Hanson – Private Equity: Fund Formation. “William Hanson of Sullivan & Worcester advises both sponsors and investors on the formation of private equity funds targeting a wide range of sectors, with a particular focus on the food and beverage industry." Will Hanson is knowledgeable, efficient and listens patiently when we discuss issues. He ensures that what we need is appropriate to our business plan." Richard Jones – Tax (Massachusetts). “Richard Jones provides transactional advice and litigation counsel to his clients across a broad range of sectors. He is noted for his expertise in relation to state and local tax matters.” David Leahy – Registered Funds (Nationwide). “David Leahy is valued for his astute advice to independent trustees and directors of mutual funds, closed-end funds and ETFs.” "David is always knowledgeable, with a plethora of experience." David Mahaffey – Registered Funds (Nationwide). “David Mahaffey is best known for his high-level representation of independent trustees for ETFs and open- and closed-end funds.” "David is an industry exemplar with his breadth of experience and in-depth industry knowledge. He is very much a problem solver with a can-do attitude." Stephanie Monaco – Investment Funds: Regulatory and Compliance (Nationwide). “Stephanie Monaco of Sullivan & Worcester frequently advises both private and registered fund clients on SEC and ’40 Act compliance. She brings experience of working in the hedge funds sector to her private practice.” Louis Monti – REITs (Nationwide). “Louis Monti represents REIT clients in NYSE and NASDAQ-related matters. His work often includes a broad range of tax, corporate and wider finance matters.” Ameek Ashok Ponda – Tax (Massachusetts) and REITs: Tax (Nationwide). “Ameek Ashok Ponda's global transactional REIT practice regularly sees him handling REIT conversions as well as M&A.” "Ameek is a great leader in the industry and helps provide detailed advice – highly trusted." Domenick Pugliese – Registered Funds (Nationwide). “Domenick Pugliese's broad capabilities enable him to handle ETFs and mutual funds matters, with particular expertise in advising independent trustees.” Nicole Rives – Private Equity, Fund Formation (Massachusetts). “Nicole Rives of Sullivan & Worcester has a broad-based private equity practice that sees her acting on behalf of both sponsors and institutional investors.” Gregory Sampson – Real Estate: Zoning/Land Use (Massachusetts). “Gregory Sampson has experience across a range of real estate matters including permitting, developments, entitlements and loans.” "Greg Sampson is super smart. He continues to do wonderful things in land use development." Amy Sheridan – Employee Benefits & Executive Compensation (Massachusetts). “Amy Sheridan has a broad practice and regularly advises on tax compliance, as well as assisting with transactional matters. She is also well-versed in deferred compensation plans.” "Amy is exceptional in all facets of ERISA. I trust her technical skills and professionalism." Douglas Stransky – Tax (Massachusetts). “Douglas Stransky has experience advising on complex domestic and international tax planning for clients across finance, life sciences and other sectors. He leads Sullivan's international tax practice group.” "Doug's deep knowledge of the law is matched by a sharp strategic mindset and exceptional attention to detail." Sarah Wellings – REITs: Tax (Nationwide). “Sarah Wellings is an up-and-coming practitioner at Sullivan & Worcester who is highly regarded for her REIT tax practice. Sarah is active acting as tax counsel in REIT compliance matters.” "Sarah is detail-oriented, proactive and a true partner. She is excellent and patient with educating clients regarding matters." Amy Zuccarello – Bankruptcy/Restructuring (Massachusetts). “Amy Zuccarello focuses her practice on the area of corporate trust. She often serves as counsel to creditors and debtors in Chapter 11 bankruptcies and out-of-court restructurings.” "Amy is always timely, conscientious and practical." Practices/Client Comments Banking & Finance – "The team provided creative advice in complex situations." Bankruptcy/Restructuring – "Sullivan & Worcester have a breadth of knowledge and the ability to provide necessary advice." Employee Benefits & Executive Compensation – "Sullivan & Worcester's attorneys have tremendous knowledge and the ability to share that knowledge in a clear, concise manner that assures understanding." Litigation: General Commercial – "Sullivan & Worcester is exceptional when it comes to complex litigation." Real Estate – "Sullivan's local knowledge, general expertise and good people distinguishes it." Registered Funds – "Sullivan & Worcester's team is very experienced and well-versed in a variety of topics." REITs – "Sullivan & Worcester are always available, proactive and extremely thorough. They provide practical advice, quickly analyzing changes to deal structure and recalling minute details along the way." Tax – "Sullivan & Worcester resolve issues efficiently and shows commitment to client satisfaction." About Sullivan Sullivan & Worcester (Sullivan) is a premier international law firm with lawyers in Boston, London, New York, Tel Aviv and Washington, D.C. Sullivan’s clients, including Fortune 500 companies, leading financial services firms and asset managers, boards of directors, real estate companies, and emerging businesses, rely on Sullivan’s ability to navigate complex legal and operational landscapes, the impeccable judgment of its lawyers, and its commitment to best-in-class client service.

Employment & Benefits

Wonder Media Network (WMN) Acquired by the World's Largest Independent Podcast Company

Sullivan represented Wonder Media Network (WMN), a female-founded, audio-first creative studio based in New York City, in its sale to Acast, the world’s largest independent podcast company. "WMN’s mission is so tightly aligned with that of Acast - bringing important and changemaking stories to the world," said WMN CEO Jenny Kaplan. "Together, we will allow both creators and advertisers to reach new audiences, build successful businesses, and shape the future of audio."

Lewis N. Segall, Joel R. Carpenter, Amy E. Sheridan, Erika L. Todd, Johanna Colpritt and Nathan Kosik-Desmond

Nonprofit Network Drives Skills-First Movement for a More Equitable and Inclusive Future Workforce

Sullivan acts as outside general counsel for Skillsright, Inc., a nonprofit coalition of the country’s top employers and their CEOs with a mission of driving a skills-first movement to unlock career opportunities for talent without four-year degrees, for a more equitable and inclusive future workforce. Sullivan handles a wide range of matters including obtaining the organization’s nonprofit (Internal Revenue Code Section 501(c)(3)) status, advising on a variety of legal issues associated with the organization’s work, negotiating intellectual property rights, drafting employment offers and dealing with related employment and benefits issues, overseeing all contracting issues and advising on corporate governance.

Kimberly Herman, David A. Guadagnoli, Judith G.H. Edington, Erika L. Todd and Michael S. Palmisciano

Employment & Benefits

Employment & Benefits

Employment & Benefits

Employment & Benefits