Executive Assistant

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 is a growing financial planning firm dedicated to helping clients achieve financial confidence through comprehensive planning and an exceptional client experience. As we continue to grow, we are seeking an experienced Executive Assistant with 5+ years of C-level EA experience to serve as a trusted partner to our fast-moving CEO.

This is a high-impact role for someone who thrives in a fast-paced environment, takes complete ownership of their work, and finds satisfaction in keeping complex priorities organized and running smoothly. More than a traditional administrative role, you’ll be expected to stay ahead of priorities, anticipate needs, make confident decisions, and ensure the CEO’s time and attention remain focused on the highest-impact work.

If you’re someone who values impact, structure, and partnership, this role was designed for you.

What You’ll Own

• Strategic Calendar Management - anticipate priorities, manage shifting demands, and ensure the CEO’s time is always aligned with the most important work.
• Communication Management - confidently triage hundreds of daily emails, prioritize what matters, and communicate with accuracy and clarity.
• Meeting & Project Support - lead preparation for leadership meetings, support speaking engagements (including PowerPoints and content), and track projects with accountability.
• Travel Coordination - oversee complex travel plans with 100% accuracy and deliver clear itineraries in advance.
• Information & Document Management - create polished reports, presentations, and research that support confident decision-making.
• Ownership Mentality - bring backbone and confidence to the role. You won’t wait for instructions - you’ll act, anticipate, and stand strong in your space.

Success Metrics

• Calendar: 98% accuracy, 95% briefs delivered 24 hours in advance.
• Communication: 100% emails acknowledged within 2 hours, 99% accuracy relaying messages.
• Projects & Tasks: 95% on-time completion, weekly updates without misses.
• Meetings & Events: 100% logistics success, 90%+ satisfaction rating.
• Travel: 100% accurate itineraries, delivered 48+ hours before departure.
• Process Improvement: 1-2 workflow enhancements per quarter.
• Confidentiality: 0 breaches per year.
• Team/Client Coordination: 90%+ satisfaction, 100% flawless VIP handling.

Qualifications

• 5+ years supporting a CEO/Founder (entrepreneurial environment preferred)
• 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