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Executive Assistant to the CEO: Alex Aleksandrovski

Wooter · Miami, Florida · Posted Jun 28, 2026 · $80,000 to $160,000 a year

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Executive Assistant to the CEO

Location: Miami, FL.

Reports To: Alex Aleksandrovski, Founder/CEO.

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Alex's Website/Portfolio

Company Overview:

Alex Aleksandrovski is a serial entrepreneur with a proven track record of launching and scaling innovative ventures. He is the founder and CEO of :

Wooter (Wooter.com), a custom sportswear company that has generated over $120M in total revenue.

AGS (Robograding.com), the first AI-driven grading company for collectibles. Both companies are headquartered in Staten Island, NYC.

Collectors Club (CollectorsClub.com), a high-end collectibles store and lounge in Wynwood, Miami.

WagerUp (WagerUp.com), the #1 sports focused prediction market.

As Executive Assistant to the CEO, you will have the opportunity to be involved in multiple high-growth, cutting-edge ventures that span industries from sports and apparel to collectibles and gaming.

Job Overview:

We are seeking a highly organized, detail-oriented, and proactive Executive Assistant to provide top-level support to Alex Aleksandrovski. In this role, you will act as the CEO's primary point of contact, managing his schedule, coordinating meetings, and supporting his day-to-day activities across his multiple ventures. You will play a critical role in ensuring the CEO’s time is maximized, and that all projects and tasks are efficiently handled. This is an exciting opportunity for someone who thrives in a fast-paced environment and wants to work closely with a visionary leader.

Responsibilities:

  • Manage the CEO’s complex schedule, ensuring all meetings, travel, and events are organized and prioritized effectively.
  • Act as a gatekeeper for all incoming communications, including emails, phone calls, and meeting requests.
  • Coordinate logistics for business trips, conferences, and speaking engagements, including international travel arrangements.
  • Support the CEO with preparing presentations, reports, and materials for internal and external meetings.
  • Track and assist with special projects related to Wooter, AGS/Robograding, Collectors Club, and WagerUp.com, ensuring timely execution.
  • Liaise between the CEO and various stakeholders, including investors, clients, and internal teams.
  • Handle confidential information with the utmost discretion and professionalism.
  • Manage ad hoc requests and personal tasks, including running errands as needed.
  • Assist with the planning and execution of key company events, openings, and special functions, such as the launch of Collectors Club in Miami.
  • Maintain task lists, monitor progress on ongoing initiatives, and ensure deadlines are met.
  • Provide flexibility to work outside normal hours, as the CEO’s ventures operate across multiple time zones.

Requirements:

  • Proven experience as an Executive Assistant or in a similar role, supporting senior executives in a fast-paced, high-demand environment.
  • Superior organizational and time-management skills, with the ability to prioritize tasks and manage multiple responsibilities.
  • Strong written and verbal communication skills, with a keen attention to detail.
  • High level of professionalism and discretion, particularly when handling sensitive information.
  • Proficiency in Microsoft Office Suite (Word, Excel, PowerPoint, Outlook) and project management software.
  • Experience managing complex travel arrangements and meeting coordination.
  • Ability to work independently and take initiative when necessary.
  • Experience or interest in the tech, collectibles, sports, or gaming industries is a plus.
  • Bachelor’s degree preferred.

What We Offer:

  • The opportunity to work closely with a visionary CEO involved in several innovative industries.
  • A fast-paced, entrepreneurial work environment with ample room for growth.
  • Competitive salary and benefits package.
  • Exposure to cutting-edge ventures in sports, apparel, collectibles, and gaming.

Apply on company site