Strategic Executive Assistant

Bully Pulpit International; United States; Hybrid; USD 56,000 - 75,000; Full time

Benefits offered by this job

Medical, dental & vision insurance

401(k) with employer match

Vacation time

Phone reimbursement

Unlimited sick time

Paid parental leave

Job summary

Bully Pulpit International in Chicago is seeking an organized Operations Assistant to support multiple executives. You will help manage complex calendars, arrange travel, submit hours, and handle expenses, enabling leaders to focus on strategic priorities and daily operations.

Based in our CHI office with some cross‑office collaboration, the role requires proactive problem solving, discretion, and strong communication.

Qualifications

• 3+ years in an executive assistant or internal operations role.
• Experience managing complex calendars in fast-paced environments.
• Ability to prioritize and meet deadlines while balancing long-term goals.
• Exceptional organizational and time management skills.
• Strong interpersonal and communication skills with discretion.

Responsibilities

• Provide executive level administrative support for high-level executives.
• Manage complex schedules, travel, timesheets and expenses.
• Oversee CHI office operations and ensure smooth daily activities.
• Collaborate with leadership to plan events and calendar activities.

Skills

Executive support

Calendar management

Organizational skills

Communication skills

Discretion

Multitasking

Proactive mindset

Job description

Bully Pulpit International in Chicago is seeking an organized Operations Assistant to support multiple executives. You will help manage complex calendars, arrange travel, submit hours, and handle expenses, enabling leaders to focus on strategic priorities and daily operations.

Based in our CHI office with some cross‑office collaboration, the role requires proactive problem solving, discretion, and strong communication.