Executive Assistant; Chief Operating Officer & Managing Director, Human Resources

Wespath Benefits and Investments • Glenview, IL

8d • Hybrid

About The Position

Wespath has an opportunity for an Executive Assistant; Chief Operating Officer (COO) & Managing Director, Human Resources (MDHR). This hybrid role provides executive administrative support (60%) to the Chief Operating Officer and support (40%) to the Managing Director, Human Resources. The position serves as a trusted liaison across the organization, while maintaining a high degree of discretion, independent judgment, and disciplined execution across confidential, documentation‑heavy workflows, including daily operations, document preparation, and general administrative support.

Requirements

• High school diploma
• 7+ years of experience as an Executive Assistant supporting C-suite level executives in a corporate or business environment.
• Proven ability to manage confidential, complex work independently with strong judgment and discretion.
• Critical thinking and problem-solving skills.
• Strong organizational, time management, documentation, and follow‑up skills across multi‑stakeholder workflows.
• Excellent written and verbal communication skills with high attention to detail.
• Proficiency in Microsoft 365 (Excel, Outlook, Teams, SharePoint/OneDrive); ability to quickly learn new systems.

Nice To Haves

• Bachelor’s degree in a related discipline to the role
• 1 - 3 years of experience supporting or working closely with the Human Resources function
• Experience supporting compliance, regulatory, and audit processes (including SOC‑1)
• Experience using CRMs, workflow tools, or document management systems to maintain a single source of truth.

Responsibilities

• Manage all aspects of internal and external scheduling and maintenance of calendar and appointments. Resolve conflicts and respond effectively to urgent issues.
• Coordinate comprehensive domestic and international travel arrangements.
• Prepare and distribute meeting agendas in coordination with other managers, directors, and senior leaders and that all preparation for all future events is on schedule.
• Track and follow-up on action items and requests to ensure assignments are completed on time.
• Draft and manage correspondence, minutes, board materials, reports, presentations, and other documents, including those containing confidential or sensitive information.
• Coordinate onboarding logistics for senior leaders, such as arranging schedules and coordinating individual meetings.
• Oversee the allocation of expenses to the COO budget, process expense reports and invoice payments.
• Develop and maintain an efficient filing system. Create and update office procedures, workflows, and operational dashboards as needed.
• Act as the primary liaison for coordinating efforts with internal stakeholders and external partners.
• Greets and hosts guests cordially and professionally, receives and screens telephone calls for the COO and in backup situations for the General Secretary.
• Process expense reports, reconcile corporate credit card statements, and handle invoice approvals.
• Draft, edit, and/or format company-wide announcements, policy memos, or confidential correspondence.
• Provide high-level administrative support including document assimilation, preparation, and quality assurance.
• Coordinate logistics, agendas, and note-taking for executive leadership or HR team meetings.
• Assist with company-wide HR events, training sessions, and employee engagement programs.
• Support HR leadership routines and confidential people-related processes by preparing materials, coordinating follow ups, and escalating sensitive matters appropriately.
• Serve as a trusted partner and advisor to the MD, HR, proactively managing priorities and anticipating needs.
• Ad-hoc administrative support for the HR team.

Benefits

• Medical benefits
• Dental benefits
• Vision benefits
• Well-being benefits
• 8% employer contribution to retirement plan with an additional match up to 2% on day one.
• 22 days of PTO
• 12 paid holidays
• Hybrid working arrangement
• Bonus opportunity

What This Job Offers

• Job Type: Full-time
• Career Level: Executive
• Education Level: High school or GED