Monique Helstrom · 1 day ago
Executive Assistant
Waukesha, WI
Full-time
Onsite
Mid, Senior Level
$90K/yr - $100K/yr
5+ years expMonique Helstrom is seeking a genius-level Executive Assistant to support a values-driven CEO, Tony Drake, in a dynamic and fast-paced environment. The role involves managing the CEO's calendar, communications, and execution of various projects while providing personal support and ensuring operational efficiency.
Professional Training & Coaching
Hiring Manager
Monique Helstrom
Responsibilities
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
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
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
Qualification
Required
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
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
Preferred
Trainual, and/or have experience with EOS or traction systems
Benefits
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
Company
Monique Helstrom
How does one build and maintain a solid partnership, team, or business? It takes self-awareness, confidence, and skilled communication.
0-1 employees
Funding
Current Stage
Early StageCompany data provided by crunchbase