Executive Assistant

Drake & Associates is seeking a high-performing Executive Assistant to the CEO in Waukesha, Wisconsin. This is a dynamic, high-trust role supporting a values-driven CEO, industry innovator, and entrepreneur across multiple businesses. The right person will help him move faster, think more clearly, and execute better while keeping the fundamentals—accuracy, organization, judgment, and follow-through—firmly in place.

The CEO is the founder of a fast-growing retirement and wealth management firm built around trust, ownership, and integrity. He is direct, fast-moving, data-driven, and highly entrepreneurial, and he works best with people who can anticipate, challenge, and execute rather than simply wait for direction. The ideal EA will bring structure to complexity, offer solutions, and make the CEO’s life easier in both large and small ways.

This is a 100% on-site. Benefits include health, vision, and dental coverage, 401(k) with employer match after the eligibility period, three weeks of PTO, company-wide incentive programs, professional development, and possible relocation assistance for the right candidate.

• 5+ years of Executive Assistant experience supporting a C-level executive, preferably in a fast-paced or entrepreneurial environment.
• Strong strategic thinking and judgment, with the ability to act on behalf of the CEO when appropriate.
• Exceptional organization and reliability; able to create systems that ensure commitments, details, and follow-ups are captured and completed.
• Excellent communication skills and the ability to handle difficult, sensitive, or high-stakes conversations with clarity and professionalism.
• Confidence to ask questions, clarify expectations, admit when more information is needed, and push back when appropriate.
• Emotionally intelligent, resilient, and comfortable working with strong personalities.
• Able to operate at a fast pace without sacrificing accuracy, organization, or follow-through.
• Highly proactive with strong ownership and a bias toward solving problems.
• Comfortable managing both business and personal executive support.
• Proficient in Google Workspace, Basecamp, RingCentral, Salesforce, and 90.io, or able to learn quickly.
• Fluent with Apple/Mac systems and iPhones.
• Experience with Trainual and/or EOS/Traction is a plus.
• Comfortable using AI and automation tools to improve workflows and reduce manual work.
• Willing to travel approximately 3–6 times per year for offsite retreats, industry events, and coaching sessions.
• Final candidates will complete a DISC assessment as part of the hiring process.

• Own and strategically manage the CEO’s calendar, navigating shifting priorities, protecting focus time, and staying ahead of day-to-day demands.
• Manage full inbox ownership, including triaging hundreds of emails and filtering what requires the CEO’s attention.
• Ensure meetings are purposeful, properly prepared for, and followed up.
• Draft and prepare polished presentations, reports, correspondence, and responses.
• Identify roadblocks early and resolve them quickly using sound judgment and initiative.
• Use AI and automation tools to streamline workflows and reduce repetitive work.
• Track deadlines, deliverables, decisions, and follow-up across multiple business lines.
• Coordinate with the leadership team, including weekly meeting preparation and meeting minutes.
• Lead preparation for leadership meetings and support speaking engagements, presentations, and coaching deliverables.
• Maintain visibility into organizational activity and flag the information that matters most to the CEO.
• Support special projects and ensure accountability around key commitments.
• Coordinate complex travel, including private flights/FBOs, hotels, car services, restaurants, and detailed itineraries.
• Plan and execute internal team-building events.
• Organize and occasionally attend offsite retreats, industry events, and coaching sessions.
• Handle personal executive-support needs such as personal travel, gifting, returns, and school-calendar reminders with professionalism and discretion.