Alyssa Willis

People-first Chief of Staff and HR/benefits leader with 15+ years of experience building teams, strengthening people operations, administering complex benefits programs, and translating executive priorities into scalable processes. Combines strategic leadership with hands-on expertise across talent acquisition, onboarding, employee relations, performance management, policy development, compliance, benefits, and cross-functional operations.

Chief of Staff at Sigmatico (2026-06 – Present)

• Partner with the CEO to stabilize and scale a fast-moving stop-loss general agency, aligning people, priorities, client operations, and internal accountability.
• Lead cross-functional operations spanning implementation, account management, reporting, workflow design, team communication, and process improvement.
• Establish clearer ownership, operating rhythms, training expectations, and quality-control practices to support a newly built team and improve execution.

Chief of Staff at National Integrative Health (2024-10 – 2026-05)

• Served as a strategic partner to executive leadership, translating growth priorities into people, organizational, and operational initiatives.
• Scaled the organization from 4 to 34 employees, leading workforce planning, recruiting, onboarding, role development, and team infrastructure to support rapid growth.
• Owned core People Operations functions, including employee relations, performance management, benefits administration, policy development, employee communications, and manager support.
• Built and formalized HR programs and policies across PTO, leave, bereavement, background checks, referrals, performance reviews, disciplinary practices, 401(k), payroll cadence, and workplace expectations.
• Designed onboarding and 30/60/90-day performance practices, strengthened employee experience, and created repeatable processes for a growing multi-functional team.
• Managed benefits vendors, enrollment, employee communications, commercial insurance, and compliance-related administration while partnering closely with leadership on organizational risk.
• Built strategic partner and vendor relationships and collaborated across operations, sales, clinical, and pharmacy teams to improve internal processes and client experience.

VP, Strategic Partnerships & People Operations at National Integrative Health (2024-10 – 2025-09)

• Led People Operations while supporting business growth, including recruiting, onboarding, benefits, employee support, policy administration, performance expectations, and organizational communications.
• Developed and expanded the Pharmacy Services function, clarifying roles, workflows, training needs, and cross-functional collaboration as the department grew.
• Supported CEO priorities, outside sales performance, strategic partnerships, partner onboarding, and implementation deliverables.

Benefits Manager at Wright Tree Service (2025-09 – 2026-02)

• Directed medical, dental, vision, retirement, wellness, and voluntary benefits administration, including annual enrollment, vendor management, employee education, audits, and reconciliations.
• Managed FMLA, ADA accommodations, STD/LTD, and leave processes while supporting compliance with ACA, COBRA, HIPAA, ERISA, and FMLA requirements.
• Resolved complex employee benefit issues and served as a trusted resource to employees, leaders, brokers, and external vendors.

Employee Benefits Account Manager II at Lockton (2023-02 – 2024-10)

• Advised clients on group insurance strategy and coordinated complex projects across pharmacy, analytics, wellness, and specialty teams.
• Led renewal planning, RFP and marketing processes, financial analysis, recommendations, presentations, and client communications from strategy through execution.

Sr. Employee Benefits Client Manager & Department Supervisor at North Risk Partners (2014-01 – 2023-12)

• Led employee benefits client service while supervising department operations and supporting HR functions including recruiting, retention, employee relations, performance management, training, and policy administration.
• Managed HRIS data, HR reporting, wellness initiatives, learning and development plans, disciplinary processes, and employee communications.
• Built and maintained carrier/vendor relationships and administered benefit programs with a strong focus on service, accuracy, and employee experience.

Human Resources Administrator at Storey Kenworthy (2011-05 – 2014-01)

• Administered employee benefits, recruiting and retention, HRIS, performance management, employee training, wellness programs, policies, and disciplinary processes.
• Supported EEO/AAP responsibilities, HR reporting, employee relations, learning and development, and company-wide events.

Bachelor in Human Resources Management and Organizational Leadership – Columbia Southern University

Associate in Liberal Arts – Kirkwood Community College