Strategic Executive Assistant to CEO — Proactive Partner

Drake & Associates, LLC; Milwaukee (WI); On-site; USD 65,000 - 90,000; Full time

Job summary

Drake & Associates, LLC is seeking an experienced Executive Assistant to partner with our fast-moving CEO. This high-impact role is ideal for someone who thrives in a dynamic, structured environment and owns priorities end-to-end.

You will manage calendars, emails, meetings, travel, and confidential documents, ensuring the CEO remains focused on high-impact work. 5+ years of C-level EA experience is required.

Qualifications

• 5+ years supporting a CEO/Founder in an entrepreneurial environment.
• Confident, proactive, and able to take full ownership of the role.
• High attention to detail and strong organizational skills.
• Emotionally intelligent with excellent communication skills.
• Tech-savvy and comfortable with fast-moving priorities.

Responsibilities

• Strategic Calendar Management: anticipate priorities and align CEO time with top work.
• Communication Management: triage emails and relay messages with clarity.
• Meeting & Project Support: prepare leadership meetings, create presentations, track projects.
• Travel Coordination: manage complex travel plans with accuracy.
• Information & Document Management: produce polished reports and research for decisions.

Skills

Attention to detail

Organizational skills

Communication skills

Proactive ownership

Tech-savvy

Job description

Drake & Associates, LLC is seeking an experienced Executive Assistant to partner with our fast-moving CEO. This high-impact role is ideal for someone who thrives in a dynamic, structured environment and owns priorities end-to-end.

You will manage calendars, emails, meetings, travel, and confidential documents, ensuring the CEO remains focused on high-impact work. 5+ years of C-level EA experience is required.