Executive Assistant to Chief Executive Officer

Monique Helstrom; Waukesha (WI); On-site; USD 90,000 - 100,000; Full time

Benefits offered by this job

Full health, vision, and dental

401(k) with employer match

Incentive programs

Professional development opportunities

Relocation assistance may be possible

Job summary

Drake & Associates in Waukesha, WI is seeking an executive assistant to be the force multiplier behind a values-driven CEO and entrepreneur across its retirement and wealth management ventures.

You will manage calendar and communications, triage emails, prepare polished presentations, and coordinate with the leadership team. Expect travel planning, private arrangements, and high-trust collaboration in a fast-moving, results-driven culture.

Qualifications

• 5+ years of experience supporting a C-level executive.
• Strong organizational and execution capabilities in fast-paced environments.
• Ability to move quickly while maintaining accuracy and follow-through.
• Comfort with AI and automation tools to streamline workflows.
• High-D DISC profile; values of honesty, ownership and coachability.

Responsibilities

• Own calendar management and prioritize shifting demands.
• Triage emails and manage full inbox ownership.
• Ensure meetings are purposeful and well-prepared.
• Draft polished presentations and reports for internal and external audiences.
• Identify roadblocks early and remove them quickly with bias for action.
• Leverage AI and automation to streamline workflows.
• Coordinate travel, events, and personal support tasks as needed.
• Coordinate with leadership team and prep meeting minutes; track projects.

Skills

Executive support

Calendar management

Email triage

Communication

Project coordination

Decision making

Discretion

Tools

Google Workspace

Basecamp

RingCentral

Salesforce

90.io

Apple/Mac systems

iPhone proficiency

Trainual

EOS/Traction

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.

https://www.linkedin.com/in/tony-drake-cfp/

https://www.linkedin.com/company/drake-&associates/