CLOSED | Executive Assistant to Wealth Manager | Waukesha, WI
This job opportunity is currently closed. Please return to the Job Opportunities page for more open Executive Assistant positions.
QUICK FACTS:
Company: Drake & Associates
Location: Waukesha, WI
Employment Type: Full-time, onsite M-F
Salary: $90,000-$100,000 with benefits
Travel: 3-6x per year
Reports to: CEO
ABOUT THE ROLE
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, drives execution with precision, and wants to be more than just an assistant. The CEO is looking for a true thought-partner—someone who helps him move faster, think clearer, and execute better across both his financial business and his speaking, coaching, podcast, and radio ventures.
This role demands someone who can match his speed and intensity, anticipate his needs, and stay three steps ahead without being asked. You’ll handle business and personal tasks alike, helping Tony stay focused, organized, and operating at peak performance.
ABOUT THE CEO
Tony Drake is the Founder and CEO of Drake & Associates, 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, Tony 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 always being coachable.
The right person will bring structure to the chaos, offer solutions (not problems), and make Tony’s life easier in ways big and small.
WHAT YOU’LL DO:
CALENDAR, COMMUNICATIONS, AND EXECUTION
Own Tony’s 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
MEETINGS, PROJECT MANAGEMENT & STRATEGIC SUPPORT
Track deadlines, deliverables, and decisions across business lines
Coordinate with Tony’s leadership team, including weekly meeting prep and talking 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 fastpaced 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
Emotionally intelligent, grounded, and loyal, with a strong backbone and zero fear of standing up to big personalities
Solution-oriented and forward-thinking, with a dog-with-a-bone mindset for getting things done
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 own an iPhone—if you’re a PC or Android user, this won’t work
Bonus: Trainual, and/or have experience with 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
People who need constant praise, reminders, or step-by-step instructions
Anyone allergic to speed, ambiguity, or feedback
A toxic personality who stirs up drama or tension on the team
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.
Do not apply unless you meet the qualifications and expectations clearly outlined above.
Looking for other executive assistant opportunities?
FREQUENTLY ASKED QUESTIONS ABOUT THE ROLE
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No — this role is onsite in Bonita Springs, Florida.
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3+ years of high-level Executive Assistant experience is required for this role.
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Relocation expenses are not being considered at this time.
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Though this role involves helping to coordinate travel for the CEO, the Executive Assistant is not expected to travel for work.
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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 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…
To spend surprisingly little time talking about calendars and travel because this is not an administrative job posting—it’s a partnership job posting.
(The clues are everywhere in the language.)
The CEO isn’t looking for someone to assist her—she’s hiring someone to manage the conditions that allow the CEO to do her best work. She’s looking for someone to create calm, judgment, and leverage.
Every interview answer should reinforce that you are not an order-taker, but a trusted operator who brings judgment, foresight, emotional intelligence, and calm to a fast-moving executive environment.
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.