Executive Assistant

This range is provided by Monique Helstrom. Your actual pay will be based on your skills and experience — talk with your recruiter to learn more.

$90,000.00/yr - $/yr

Direct message the job poster from Monique Helstrom

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 a simple 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.

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.

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 Power Points 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

• 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
• 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, Ring Central, 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,…