Jamie Wilcox

About Jamie Wilcox

I’m an experienced and strategic Benefits Manager with over 17 years of success designing, managing, and optimizing comprehensive health, welfare, retirement, and leave programs. I specialize in building benefits strategies that strengthen the employee experience, streamline operations, and align seamlessly with business goals.Throughout my career, I\'ve led large-scale benefits initiatives, driven process improvements, enhanced compliance practices, and delivered measurable cost savings—all while ensuring employees feel genuinely supported and valued. With deep expertise across U.S. and Canadian benefits landscapes, self-funding, regulatory compliance, and HR technology, I’m passionate about using benefits as a tool to shape a positive, inclusive workplace culture and attract and retain top talent.I thrive in fast-paced, high-growth environments, partnering with executive leadership to develop employee-first solutions that drive engagement and business success. As a trusted advisor and collaborative leader, I am committed to delivering thoughtful, innovative benefits programs that truly make a difference.CORE SKILLS & EXPERTISE Strategic Benefits Leadership: Health & Welfare Programs (U.S. & Canada)| Leave Administration | ASO & Self-Funded Plans | Regulatory Compliance (ACA, ERISA, HIPAA, Section 125)| 401(k) Plan Management & Audits | Form 5500 Filings | Nondiscrimination TestingEmployee Experience & Engagement: Open Enrollment Strategy & Communications | Employee Advocacy | Wellness & Mental Health Programs | DEI-Centered Benefits InitiativesHR Technology & Process Optimization: HRIS Expertise (Workday, ADP, Paylocity, UKG/UltiPro, Benetrac, Gusto, JIRA)| Benefits Process Automation | Data Analysis & Reporting | Operational EfficiencyStakeholder Collaboration & Leadership: Vendor & Carrier Management | Executive Partnership & Communication | Cross-Functional Team Collaboration | Project Management | Team Coaching & DevelopmentPERSONALITY INSIGHTSEnneagram: Type 1 (The Reformer – principled, purposeful, self-controlled)DISC Style: SC (Technician – systematic, accurate, and supportive)

Experience

1. Senior Manager, Benefits

   1Password

   Mar 2026 — Present

Education

• California Polytechnic State University-San Luis Obispo

  BA, History

  2003 — 2006

Skills

• Carrier Relationship Management
• Microsoft Office 2007
• Account Coordination
• Employee Wellness
• Employee Benefits
• Adobe Professional
• Health & Welfare Benefits Administration
• Superior Client Service
• Brokers
• Disability Insurance
• Css
• Claims Resolution
• Benefits Administration
• Management
• Strategic Communications
• Open Enrollment