Director of Benefits

Who We Are

At Benesch we pride ourselves on exceeding expectations and building trust not only with our clients but with our employees - Benesch's #1 asset. Committed to providing not only the highest level of legal service to our clients, Benesch also aspires to create a positive work environment for our employees. Our Firm continues to earn placement on Chicago and Cleveland's Top Workplaces list, along with Cleveland's NorthCoast 99 Top Workplaces rankings. We also continue to advance on the AmLaw 125 list, placing us among the top 125 law firms in the country.

Benesch is proud to be recognized for being a Firm that attracts and retains top talent - making Benesch a great place to work. We offer a hybrid schedule, career development and growth, transparent and visible leadership teams, and a place where diversity, equity and inclusion is celebrated. In addition, the Firm offers a full array of benefits which can be viewed at

Working with Us - Come and "Be Benesch!"

We are one of the fastest growing firms in the nation, and have offices in Chicago, Cleveland, Columbus, Miami, New York City, San Francisco, and Wilmington. We continue to expand our geographic footprint and value the talent that comprises each of our locations. If you are someone who champions a First in Service approach and are ready to be part of an exciting and growing Firm, we would invite you to apply to join our team.

Want to know more? To hear from some of our team, click here:

Benesch is proud to announce the opening for a Director of Benefits  in our Cleveland  office! This position is hybrid and has work from home flexibility.

Position Summary:

The Director of Benefits provides strategic leadership and hands-on direction for the full benefits function at Benesch. The Director develops and executes a forward-looking benefits and wellbeing strategy that supports the Firm's talent objectives, employee and partner experience, financial stewardship, and commitment to a high-performing workplace. This role is accountable for the design, administration, governance, communication, and continuous improvement of health and welfare benefits, financial wellbeing programs, leaves and disability programs, workers' compensation, and Firm-wide wellness initiatives.

The Director serves as a trusted advisor to the Chief Human Resources Officer and Firm leadership, translating market trends, utilization data, financial results, regulatory developments, and workforce needs into clear recommendations. The role combines enterprise-level strategy with tactical execution, including vendor and broker management, annual renewals and RFPs, budget ownership, compliance oversight, escalated participant advocacy, technology optimization, and leadership of the benefits team.

Essential Functions

Benefits Strategy and Leadership

1. Develops and leads a multi-year benefits and wellbeing strategy aligned with the Firm's business priorities, talent strategy, culture, growth, and market position within the legal and professional services sector.
2. Advises the CHRO and senior leadership on plan design, funding, cost-sharing, emerging benefits, policy direction, risk, and investment priorities. Presents clear, decision-ready recommendations supported by financial, competitive, utilization, and employee-experience data.
3. Maintains a disciplined benefits roadmap and annual operating calendar that integrates renewals, RFPs, open enrollment, compliance, communications, vendor reviews, audits, and program launches.
4. Monitors legislative, regulatory, market, workforce, and healthcare trends and proactively recommends changes that strengthen competitiveness, sustainability, access, and participant value.
5. Partners across Human Resources, Finance, Payroll, Legal, Internal Communications, People Systems, and Firm leadership to ensure benefits priorities are coordinated and effectively executed.

Plan Design, Financial Stewardship and Analytics

• Leads the evaluation, design, implementation, and ongoing management of the Firm's health and welfare, retirement and financial wellbeing, leave, disability, life, voluntary, and ancillary benefit programs.
• Owns benefits budgeting, forecasting, renewal modeling, monthly variance review, invoice governance, and executive reporting. Identifies cost drivers, financial risks, savings opportunities, and areas for strategic reinvestment.
• Uses claims, utilization, enrollment, demographic, engagement, service, and financial data to evaluate program performance and guide decisions. Establishes meaningful scorecards and key performance indicators for the function.
• Oversees plan audits, eligibility and census reconciliation, funding and billing controls, compliance testing, and documentation to support accurate and financially sound administration.
• Balances employee and partner experience, access, program quality, market competitiveness, administrative feasibility, fiduciary considerations, and total cost in benefits recommendations.

Vendor, Broker and Consultant Management

• Serves as the executive relationship owner for benefit brokers, consultants, carriers, administrators, technology partners, wellbeing providers, and other third parties supporting the benefits function.
• Leads competitive RFPs, finalist evaluations, negotiations, contracting, implementation, and transition planning in partnership with Procurement, Legal, Finance, and other stakeholders as appropriate.
• Establishes measurable service levels, performance guarantees, implementation standards, reporting expectations, escalation protocols, and governance routines. Conducts periodic business reviews and holds vendors accountable for outcomes.
• Evaluates vendor performance, fees, transparency, service quality, participant experience, data security, financial results, and strategic fit. Develops corrective action plans and recommends vendor changes when performance does not meet expectations.
• Coordinates vendors and internal teams to resolve complex or systemic participant issues while protecting confidentiality and ensuring a consistent, high-touch experience across Firm offices.

Benefits Operations and Tactical Execution

• Provides leadership and oversight for end-to-end benefits administration, including new-hire and life-event enrollment, annual enrollment, eligibility, executive and partner benefits, COBRA, leaves, disability, claims support, appeals, workers' compensation, and participant communications.
• Ensures benefits administration platforms, interfaces, payroll deductions, plan configurations, workflows, records, and data are accurate, secure, well controlled, and continuously improved.
• Leads annual open enrollment strategy and execution, including plan decisions, system readiness, testing, communications, educational programming, enrollment support, and post-enrollment reconciliation.
• Serves as the senior escalation point for complex benefits, leave, disability, claims, access, and vendor service matters. Ensures issues are resolved promptly, consistently, and with appropriate documentation.
• Establishes and maintains standard operating procedures, controls, service standards, calendars, and cross-training to support reliable execution, business continuity, and a scalable benefits operating model.
• Remains actively engaged in critical deliverables and is prepared to execute tactical work directly when needed to ensure deadlines, service expectations, and compliance obligations are met.

Wellbeing Strategy and Engagement

• Develops an integrated, inclusive wellbeing strategy that addresses physical, emotional, financial, family, and social wellbeing and reflects the needs of a high-performance professional workforce.
• Builds a cohesive portfolio of wellbeing programs, resources, education, campaigns, and incentives that connects employees and partners to relevant benefits and supports sustainable engagement.
• Uses workforce feedback, participation, outcomes, vendor data, and program utilization to assess effectiveness, identify gaps, and refine the wellbeing strategy.
• Partners with internal communications, Firm leaders, benefits vendors, and local office stakeholders to create accessible, practical, and compelling wellbeing experiences across offices and employee populations.
• Ensures wellness programs are administered consistently with applicable legal requirements, privacy standards, reasonable accommodation obligations, and voluntary participation principles.

Compliance, Governance and Risk Management

• Maintains current, expert-level knowledge of laws and regulations affecting employee benefits and leaves, including ERISA, ACA, COBRA, HIPAA, FMLA, ADA, USERRA, Section 125, workers' compensation requirements, and applicable state and local laws.
• Oversees required filings, notices, disclosures, plan documents, nondiscrimination testing, audits, privacy practices, records retention, and governance processes, working with legal counsel and external advisors as appropriate.
• Supports the Firm's responsibilities as plan sponsor and plan administrator by maintaining prudent processes, clear documentation, appropriate controls, and effective oversight of delegated administrators and other service providers.
• Identifies compliance, fiduciary, privacy, operational, and financial risks; escalates material issues; and implements timely remediation plans.

Team Leadership and Service Delivery

• Leads, develops, and holds accountable the benefits team, establishing clear roles, priorities, service standards, performance expectations, and development plans.
• Builds a collaborative, knowledgeable, responsive, and solutions-oriented team culture grounded in accuracy, confidentiality, empathy, accountability, and continuous improvement.
• Assesses capacity, skills, workflow, and technology needs and allocates work to ensure strategic initiatives and recurring administration are both executed successfully.
• Creates benefits education, decision-support resources, and targeted communications that help employees and partners understand, access, and use the Firm's programs effectively.
• Demonstrates exceptional judgment and discretion when handling sensitive medical, financial, employee, and partner information.

Additional Responsibilities

• Participates in broader Human Resources and Firm initiatives and contributes benefits expertise to workforce planning, talent, employee experience, and organizational change efforts.
• Develops and maintains productive relationships with benefits peers and professional networks to identify emerging practices and strengthen the Firm's market perspective.
• Performs other duties and leads special projects as assigned.

Qualifications

• Bachelor's degree in human resources, business administration, finance, healthcare administration, or a related field required. Advanced degree or relevant professional certification, such as CEBS, SHRM-SCP, SPHR, or equivalent, is preferred.
• Ten or more years of progressively responsible employee benefits experience, including substantial responsibility for strategy, plan design, financial management, vendor governance, compliance, and complex benefits administration. Prior people leadership experience is required.
• Experience with self-funded health plans and sophisticated health and welfare programs is required.
• Experience in a law firm, professional services firm, or other multi-office, high-touch environment is preferred.
• Demonstrated ability to operate as both a strategic leader and hands-on functional owner, moving effectively between executive recommendations, program design, vendor negotiations, operational problem-solving, and detailed execution.
• Expert knowledge of employee benefits laws, plan governance, privacy requirements, and compliance practices, with the judgment to recognize when legal, actuarial, financial, or other specialized guidance is needed.
• Strong business and financial acumen, including experience with budgets, forecasting, claims and utilization analysis, renewal modeling, contract terms, performance guarantees, and executive-level reporting.
• Proven ability to lead RFPs, negotiate with vendors, manage complex implementations, establish governance and service standards, and drive measurable performance improvement.
• Exceptional written and verbal communication skills, with the ability to translate technical, financial, and regulatory information into clear guidance and decision-ready recommendations for varied audiences.
• Advanced project management, organization, analytical thinking, and problem-solving skills.
• Demonstrated ability to manage multiple priorities, anticipate risk, and deliver high-quality work in a fast-paced environment.
• High proficiency with benefits administration platforms, HRIS and payroll integrations, reporting and analytics tools, and Microsoft 365 applications. Demonstrated interest in using technology and automation to improve service, controls, and efficiency.
• Unquestioned integrity, sound judgment, executive presence, discretion, and a strong commitment to client service.

Confidentiality

Due to the nature of this position, the Director of Benefits will have access to confidential and sensitive Firm, employee, partner, medical, financial, and business information. All such information must be handled with the highest degree of discretion and maintained in accordance with Firm policy and applicable law.

The salary range for this position is $183K to $225K.

Please note that quoted salary ranges are based on Benesch's good faith belief at the time of the job posting and are not a guarantee of what final salary offers may be. Base pay is based on market location and may vary depending on job-related knowledge, skills, and experience. Base pay is only one part of the Total Rewards that Benesch provides to compensate and recognize our staff professionals for their work. Full-time positions are eligible for a discretionary bonus and a comprehensive benefits package.

Benesch is an equal opportunity employer. We strongly value and encourage diversity and solicit applications from all qualified applicants without regard to race, color, gender, sex, age, religion, creed, national origin, ancestry, citizenship, marital status, sexual orientation, physical or mental disability (where applicant is qualified to perform the essential functions of the job with or without reasonable accommodations), medical condition, protected veteran status, gender identity, genetic information, or any other characteristic protected by federal, state, or local law.

Applicants who are interested in applying for a position and require special assistance or an accommodation during the process due to a disability should contact the Benesch Human Resources Department by phone at View phone number on click.appcast.io or email at View email address on click.appcast.io.

Equal Opportunity Employer/Protected Veterans/Individuals with Disabilities