Anna N. Alfano

Benefits and Leave leader proven success driving cost savings, compliance, and scalable operations across complex organizations, expert in benefits strategy, M&A integrations, retirement plan governance, and team leadership, delivering measurable financial impact and improved employee experience.

Benefits and Leave Manager - CRYSTAL CLEAN, LLC - Hoffman Estates, IL (HYBRID)

(2025 - 2026)

Benefits and Leave leader proven success driving cost savings, compliance, and scalable operations across complex organizations, expert in benefits strategy, M&A integrations, retirement plan governance, and team leadership, delivering measurable financial impact and improved employee experience.

• Owned renewal process reducing renewal costs by 10% through plan design optimization, vendor governance, budgets, and clinical cost-management programs.
• Presented benefits changes and strategic recommendations in leadership and board-level meetings; recommendations were adopted by leadership and translated into plan, vendor, and employee-impacting decisions.
• Partnered directly with the CFO, CEO, and senior leadership on mergers and acquisitions, providing benefits due diligence, cost considerations, integration recommendations, and implementation planning.
• Presented benefit renewal strategy, plan design alternatives, cost analysis, and recommendations to C-suite and senior leadership, including clear options and financial impact to support executive decision-making.
• Led benefits due diligence and integration for multiple acquisitions, including special enrollments, plan conversions, and 401(k) deconversions.
• Directed 401(k) governance, including audits, discrimination testing, and in-house company-wide true-ups to remediate historical contribution gaps.
• Served as executive owner of benefits and retirement regulatory compliance, overseeing 5500 filings, 1095 processing, participant disclosures, and audit readiness.
• Partnered with HRIS, Payroll, Finance, Legal, and vendors to ensure accurate system configuration, file feeds, and operational execution.
• Established scalable benefits and M&A operating models, creating SOPs and playbooks to support growth.
• Led implementation of new life and disability programs, including vendor selection, integrations, communications, and enterprise training.
• Provided strategic leadership for Benefits, Leave, and Workers’ Compensation, including organizational design and performance management.
• Implemented vendor governance for workers’ compensation and leave administration, closing 20% of claims within three months.
• Acted as senior escalation leader, aligning benefits and total rewards programs with business strategy and employee experience
• Reason for leaving: Position eliminated due to organizational restructuring under Centers of Excellence model

Benefits Program Manager of North America - pRESTONE PRODUCTS CORPORATION (d/b/a Recochem inc) - Rosemont, IL (HYBRID)

(2024 - 2025)

Health and Welfare Benefits Management & Administration expert responsible for overseeing comprehensive benefits programs for ~1000 employees in the US and Canada, including leave of absence administration, benefit plan implementation, and the annual renewal process.

• Led the marketing and implementation of comprehensive benefit programs post-acquisition, 20 benefit plans with 14 vendors, including Medical, Dental, Vision, Life and Disability, Absence Management, Flexible Spending Accounts, COBRA, and Voluntary Benefits. Successfully coordinated with vendors to ensure seamless setup, file feed integrations, and system configurations.
• Directed the deconversion of two retirement plans into a single, unified retirement plan, managing plan design, data migration, and employee communication strategies, and compliance filings (5500s, non-discrimination testing, true-up calculations).
• Partnered with HRIS and technical teams at Ceridian/Dayforce to develop and implement an open enrollment system ensuring full functionality, platform testing, and readiness for the open enrollment period.
• Conducted benefits cost forecasting and analysis, identifying opportunities for cost savings and aligning benefits spend with company goals.
• Partnered with executive leadership on acquisition-related benefit strategy, including plan changes, integration decisions, financial considerations, and employee communications.
• Developed and presented Open Enrollment strategy, communications, leadership materials, and employee benefit fair content to drive understanding and participation across the U.S. and Canada.
• Presented renewal findings, cost projections, plan design recommendations, and proposed changes to senior leadership, translating complex benefits data into actionable business decisions.
• Led consolidation of legacy benefit plans post-acquisition, ensuring seamless integration.
• Spearheaded the US and Canada Open Enrollment process, creating communication materials, conducting webinars, hosting onsite employee meetings, and auditing post-enrollment activity for accuracy.
• Directed the implementation of wellness programs and other health initiatives designed to support employee well-being and long-term health.
• Administered leave of absence process, collaborating with site HR teams to ensure compliance and timely responses.
• Implemented and managed the new ACA administration process through Dayforce to ensure compliance with regulations.
• Managed all vendor relationships and transitions from implementations to day-to-day activities.
• Reason for leaving: Position eliminated after acquisition and closures of manufacturing sites in Canada and US

Senior Total Rewards Specialist - lanzatech - SKOKIE, IL (CONSULTANT 6 month contract - HYBRID)

(2024 - 2024)

Hired as a consultant specializing in Health and Welfare Administration and Leave of Absence Management, overseeing the renewal process for the United States.

• Led the end-to-end marketing efforts for the search and selection of a new broker, managing all phases including vendor evaluation, investment reviews, and committee coordination.
• Managed the daily administration of retirement plans, ensuring seamless operation and adherence to plan guidelines, including processing transactions and contributions.
• Evaluated vendor performance and recommended necessary changes or new vendor selections.
• Presented vendor performance findings and recommendations to leadership and committees; recommendations supported decisions to change vendors, processes, and plan strategies.
• Participated in retirement committee meetings, reviewing investment performance, plan results, and fiduciary considerations and contributing recommendations regarding investment and plan changes.
• Collaborated with Accounting, Finance and HR departments to ensure accurate records and maintain internal compliance.
• Delivered direct support to employees, resolving issues, and addressing inquiries related to retirement plans. -
• Partnered with vendors to identify and resolve any root causes of issues, ensuring timely resolutions and continued plan effectiveness.

Human Resources Benefits Manager - United Rentals - Stamford, CT (REMOTE)

(2023 - 2023)

Expert in Health and Welfare Administration and Leave of Absence Administration, including participation in renewal process for United States, Canada, and Puerto Rico, and managing the Global Employee and Family Assistance Program, and Global Recognition Program. Lead the execution of U.S. and Puerto Rico annual open enrollment process including all related communications and system configuration, wellness programs, open enrollment meetings and webinars and other initiatives to foster long-term employee health for ~24,000 employees.

• Partnered with Director in strategy and planned design of all benefit plans, managed relationships and communications between consultants, administrative vendors, and insurance carriers to ensure quality of service and adherence to standards. Discrimination Testing, ACA reporting, and HIPAA required notices.
• Implemented life and disability programs with new carrier, including the plan designs and configuration of files.
• Managed new system implementation of Open Enrollment and ACA in WorkDay, while partnering with HRIS for a successful launch.
• Executed forward-thinking family benefits in fertility and caregiving programs, as well as enhancing wellness programs with a new diabetes program.
• Oversaw company’s Leave of Absence program for United States, Canada, and Puerto Rico, and was a subject matter expert on leave-related regulations, partnering with legal counsel on complex leave and accommodations cases.
• Oversaw benefit plan compliance by partnering with legal counsel and brokers, not limited to Plan Audits, 5500 filings, Discrimination Testing, ACA reporting, and HIPAA required notices.
• Developed webinar education on various benefits topics for 24,000 employees.
• Planned and delivered leadership communications, employee meetings, webinars, and benefit-fair education to support Open Enrollment and adoption of benefit changes.
• Presented benefits strategy, renewal recommendations, plan changes, and Open Enrollment plans to senior leadership, supporting executive decisions for a population of approximately 24,000 employees.
• Led, trained, and managed a team of 8 in benefits and leave administration ensuring all company and department goals were executed and performance evaluations completed.
• Reason for leaving: Position eliminated due to company restructuring

Human Resources Senior Benefits Manager - Follett CORPORATION - McHenry, Illinois (REMOTE)

(2021 - 2022)

Oversaw and led Benefits Department. Seasoned in strategy, design, compliance, and communication of corporate bene