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Job description
WAUKESHA, WI | 100% ON-SITE EVERY DAY (M-F) NO EXCEPTIONS
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 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.
ABOUT THE CEO:
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 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
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 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 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 & BENEFITS
$90,000–$100,000 annual salary depending on experience
Full health, vision, and dental benefits
401(k) with employer match after eligibility period
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.
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Worksite address
waukesha, WI, 53188, US
Who can apply
Review the original listing for work authorization, qualifications and employer requirements.