About Seamless Assist

Seamless Assist provides strategic operational support to growing businesses, particularly within the fitness, wellness, and service industries. We partner with founders and leadership teams to remove operational bottlenecks and create structured, efficient systems that allow businesses to scale sustainably.

Our approach goes beyond basic task execution. We focus on proactive ownership, documentation, process improvement, and intelligent use of technology. We are also committed to advancing AI literacy within our organization and among the small businesses we support by teaching practical AI tools and developing accessible learning resources.

Role Overview

We are seeking a highly experienced Executive Assistant to serve as a strategic partner to the CEO. This role requires a professional with a strong background in property management who can confidently manage traditional executive support responsibilities while overseeing aspects of the CEOs real estate portfolio.

The ideal candidate is proactive, systems oriented, highly organized, and aligned with our mission of operational excellence and AI enablement.

Key Responsibilities

Executive Support

CEO Calendar Management

• Full ownership of the CEOs calendar

• Strategic scheduling aligned with company priorities

• Protecting focus time and resolving scheduling conflicts confidently

Inbox and Communication Management

• CEO inbox triage and prioritization

• Drafting executive level communication

• Applying structured communication principles including Acknowledgement, Communication, and Turnaround Time

• Managing follow ups and stakeholder coordination

Travel and Logistics

• End to end travel planning including flights, accommodation, transport, and visas where applicable

• Detailed and cost conscious itinerary management

Real Estate and Property Portfolio Coordination

• Oversee and coordinate matters related to the CEOs real estate portfolio

• Liaise with property managers, tenants, contractors, and service providers

• Track leases, renewals, compliance requirements, and maintenance schedules

• Monitor property performance and escalate risks proactively

• Maintain organized property documentation and records

Operational and Project Ownership

• Track company initiatives and executive action items

• Coordinate cross functional projects

• Build and improve internal systems and workflows

• Ensure deadlines are met without requiring constant oversight

AI Competency and Strategic Alignment

Seamless Assist is committed to teaching employees AI tools at beginner to intermediate levels and developing practical AI learning modules for internal teams and small businesses.

The Executive Assistant will:

• Demonstrate familiarity with AI tools such as ChatGPT, Gemini, and other productivity platforms

• Show curiosity and a strong learning mindset toward emerging technologies

• Support the documentation and development of AI workflows

• Assist in teaching and guiding team members in the practical use of AI tools

Required Qualifications

• Minimum 5 years of Executive Assistant or senior executive support experience

• Experience supporting a CEO, Founder, or C suite executive

• Strong background in property management or real estate coordination

• Exceptional written and verbal communication skills

• High level of discretion and sound judgment

• Strong organizational and systems thinking ability

• Comfortable working in fast paced, high accountability environments

Key Attributes

• Proactive and anticipatory

• Strategic thinker with strong judgment

• Detail oriented without losing sight of priorities

• Independent yet collaborative

• Professional and solution oriented