OPEN | Executive Assistant to the CEO | 100% On-site in Waukesha, WI
Full-time Executive Assistant position with Drake & Associates in Waukesha, Wisconsin
QUICK FACTS:
Company: Drake & Associates
Location: Waukesha, Wisconsin
Employment Type: Full-time, 100% on-site
Salary: $90,000–$100,000 based on experience
Travel: Occasional on a small privately owned aircraft piloted by the CEO himself
Reports to: CEO
Seeking a genius-level Executive Assistant to become the force multiplier behind a values-driven CEO, industry innovator, and entrepreneur.
This is a dynamic, high-trust role for someone who thrives in fast-paced environments and drives execution with precision. The CEO is looking for someone who helps him move faster, think more clearly, and execute better across his many businesses.
This role demands someone who can match his pace without sacrificing accuracy, organization, or follow-through—someone who knows when to move quickly and when to slow down, ask the right questions, and make sure they truly have the full picture. You’ll handle business and personal tasks alike, helping him stay focused, organized, and operating at peak performance.
The CEO is the founder of a fast-growing retirement and wealth management firm rooted in entrepreneurial spirit and built on a culture of trust, ownership, and integrity. He’s a strategic visionary who thrives on speed, innovation, and impact.
A high-D DISC profile, he is direct, visual, data-driven, organized, and fiercely loyal. He expects results and operates best when surrounded by smart, capable people who can anticipate, challenge, and execute. He values honesty, extreme ownership, and coachability.
The right person will bring structure to the chaos, offer solutions instead of problems, and make the CEO’s life easier in ways big and small.
WHAT YOU’LL DO:
CALENDAR, COMMUNICATIONS, AND EXECUTION
Own his calendar like a chessboard—move with purpose, navigate shifting priorities, defend his focus, and stay ahead of the day-to-day demands
Confidently triage hundreds of emails, filter what matters, and manage full inbox ownership
Ensure every meeting is purposeful, prepared-for, and followed up
Help draft polished presentations, reports, and responses for both internal and external audiences
Identify roadblocks early and remove them quickly with good judgment and a bias for action
Comfortable using AI and automation tools to streamline workflows and reduce manual work
MEETINGS, PROJECT MANAGEMENT & STRATEGIC SUPPORT
Track deadlines, deliverables, and decisions across business lines
Coordinate with the leadership team, including weekly meeting prep and taking meeting minutes
Lead preparation for leadership meetings, support speaking engagements (including PowerPoints and content), and track projects with accountability
Maintain visibility into what’s happening across the organization and flag what matters most
Support ongoing special projects, speaking engagements, presentations, and coaching deliverables
TRAVEL, EVENTS, & PERSONAL SUPPORT
Coordinate complex travel arrangements, including private flights (FBOs), hotels, car service, and restaurant bookings—with clear, concise itineraries in advance
Plan and execute internal team-building events that reinforce culture and community
Organize and occasionally attend offsite retreats, industry events, and coaching sessions (3–6x/year travel required)
Handle personal tasks such as travel, gifting, Amazon returns, and school calendar reminders with professionalism and discretion
WHO WILL SUCCEED IN THIS ROLE
A high-performing EA with 5+ years of experience supporting a C-level executive, preferably in a fast-paced or entrepreneurial environment
A strategic thinker who can make judgment calls and act on behalf of the CEO when needed
A master communicator who can handle good news, bad news, and everything in between with clarity and competence
Confident enough to ask questions, admit when they don't know something, and clarify expectations before moving forward
Emotionally intelligent with a strong backbone and zero fear of standing up to big personalities
Exceptionally organized and reliable — creates systems that ensure commitments, details, and follow-ups are captured and completed without the CEO having to check behind them
Deeply caring about their team and company mission
Proficient in Google Workspace, Basecamp, RingCentral, Salesforce, and 90.io (or a fast learner). Must be fluent in Apple/Mac systems and iPhones
Bonus: Experience with Trainual and/or EOS or Traction systems
WHO WILL NOT SUCCEED IN THIS ROLE:
Someone with low confidence, low self-esteem, or a timid presence
Career-changers who want to "try out" being an EA
Someone who says “I've got it” before they actually understand the assignment, rather than slowing down, asking questions, or requesting additional context
People who need constant praise, reminders, or step-by-step instructions
People who overpromise, underdeliver, or make excuses when things go sideways
Anyone who gets flustered easily, hesitates to speak up, or is overly emotional
Someone who isn’t comfortable with fast pivots, complex personalities, or high expectations
COMPENSATION, REQUIREMENTS & LOGISTICS
$90,000–$100,000 annual salary depending on experience
Full health, vision, and dental benefits
401(k) with employer match after eligibility period
Three weeks PTO
Participation in company-wide incentive programs
Opportunities for professional development
Relocation assistance may be considered for the right candidate
Final candidates will complete a DISC assessment as part of the hiring process.
If you want to be a force multiplier to a mission-driven leader, and you have the skills and confidence to back it up, this is your role.
Candidates should apply only if their experience reflects the judgment, discretion, precision, and executive-level support required for the role.
Looking for other executive assistant opportunities?
FREQUENTLY ASKED QUESTIONS ABOUT THE ROLE
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NO. This is a 100% on-site/in-office position, Monday–Friday, in Waukesha, Wisconsin. No exceptions.
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Primarily executive/business support, but personal support is absolutely part of the job. The EA will handle personal travel, gifting, returns, family/school-calendar reminders, and other tasks that protect the CEO’s time.
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Yes. The CEO owns and regularly uses a private aircraft. The EA will coordinate private aviation logistics, including FBOs, ground transportation, hotels, restaurants, and detailed itineraries. Prior private aviation experience is strongly preferred.
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He is fast-paced, direct, highly entrepreneurial, visual, and data-driven. He expects accuracy, ownership, responsiveness, and strong follow-through. This is best suited to an EA who is confident, adaptable, and comfortable working with a strong personality.
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Once you’ve applied, you can expect a confirmation email that your application has been received. If your application is selected, you will receive an email from Monique Helstrom to schedule your first interview.
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Every candidate is personally reviewed by me, Monique Helstrom, former Executive Assistant to Simon Sinek and an executive recruiter specializing in high-trust executive partnerships.
My goal isn’t simply to place candidates. It’s to create partnerships that thrive.
If your application isn’t accepted for this role, don’t take it personally! This role may just not have been the one for you. Feel free to browse other open roles or schedule a resume review with me.
APPLICATION TIP FROM MONIQUE
If I were coaching someone for this interview, I’d tell them…
come prepared with specific examples that show you can keep a fast-moving executive organized, catch what others miss, ask smart clarifying questions, and follow through without needing to be managed.
P.S. Want more interview tips? Schedule a resume and interview coaching session with me. Or click here to learn more about what I do.