Strategic Executive Assistant — Hybrid, Project‑Driven Support

sentryinsurance; United States; Hybrid; USD 60,000 - 90,000; Full time

Benefits offered by this job

Hybrid flexibility

Tuition reimbursement

401(k) match

Paid time off

Parental leave

Pet insurance

Caregiver leave

Wellness resources

Job summary

Sentry is seeking an Executive Assistant to partner with executives and ensure smooth day-to-day operations. You will manage calendars, travel, and meeting logistics, and support special projects with discretion and accuracy.

Ideal candidates have at least 3 years in executive support, strong Microsoft Office skills, and the ability to work independently while coordinating with teams across the organization. Hybrid work options available across the U.S.

Qualifications

• Associate degree or equivalent work experience required.
• Minimum 3 years of related work experience.
• Executive-level administrative experience preferred.
• Proficient in Word, Excel and PowerPoint.
• Proficient with productivity tools (Workday, Zoom, MS Teams, WebEx).
• Ability to work with minimal supervision and make decisions within authority.
• Strong written and verbal communication with high attention to detail.
• Ability to handle confidential information.

Responsibilities

• Develop and maintain deep knowledge of supported business areas.
• Proactively manage complex calendars and travel arrangements.
• Relieve leadership from routine administrative tasks.
• Partner with executives on special projects and board preparations.
• Prepare documents, reports, and presentations with independent judgment.
• Act as the point of contact between executives and colleagues.
• Maintain confidentiality of executive data and documents.
• Collaborate with administrative team across the organization.

Skills

Microsoft Office

Workday

Zoom

MS Teams

WebEx

Attention to detail

Confidentiality

Education

Associate Degree or equivalent

Tools

Word

Excel

PowerPoint

Job description

Sentry is seeking an Executive Assistant to partner with executives and ensure smooth day-to-day operations. You will manage calendars, travel, and meeting logistics, and support special projects with discretion and accuracy.

Ideal candidates have at least 3 years in executive support, strong Microsoft Office skills, and the ability to work independently while coordinating with teams across the organization. Hybrid work options available across the U.S.