Personal Executive Assistant

American Tall is a thriving e-commerce brand, dedicated to producing world-class quality clothing for tall men, and women, up to 7’1. Founded by a father and son duo in 2015, the business has grown to a level that seemed almost unimaginable just a few years ago and is now a leading brand in the tall community. The growth can be attributed to the excellent leadership team and family values that drive the business – respect, passion, support, and empowerment.

We believe the best ideas come from a diverse group of people. This is a special opportunity to join an innovative business with tremendous upside, and a work culture built on the foundation of respect, inclusiveness, and continued learning.

We are seeking a proactive, detail-oriented, highly organized, and resourceful Personal Executive Assistant to support both our President and CEO. In this role, you will act as a trusted partner, helping to manage priorities, create space for deep work, and ensuring their time is spent on what matters most. You will play a critical part in simplifying both professional and personal responsibilities, freeing them to focus on driving the company’s vision forward.

This is an ideal role for someone who thrives on taking ownership, stays two steps ahead, exercises discretion, proactive problem-solving, and enjoys being the go-to person.

• Executive Support (EA Responsibilities):
• Act as a trusted partner to the President and CEO, helping to manage their time and priorities.
• Own complex calendars and daily scheduling, ensuring time is optimized and aligned with shifting priorities.
• Organize daily priorities and manage detailed to-do lists, ensuring deadlines are met and expectations are clear.
• Streamline requests and communications, ensuring the President and CEO can stay focused on key priorities while keeping the team informed and supported.
• Manage email inboxes, draft responses, and flag high-priority communications; work toward inbox zero when possible.
• Prepare agendas, take clear and concise meeting notes, and manage follow-ups to ensure nothing falls through the cracks.
• Assist with coordinating key initiatives by tracking tasks, monitoring progress, and ensuring follow-ups are completed in collaboration with project owners.
• Provide general administrative support to streamline operations and enhance productivity.
• Support the planning and execution of meetings, events, and special projects.
• Maintain confidentiality and handle sensitive information with discretion.

• Personal Support (PA Responsibilities):
• Coordinate personal scheduling, including appointments, family logistics, and errands.
• Plan and manage both personal and business travel, including complex itineraries and last-minute changes.
• Assist with lifestyle management including event planning, reservations, personal gifting, and special projects (e.g., family events, home coordination, contractor management).
• Take the initiative to suggest ways to simplify life and create space for what matters most; helping balance a demanding role with a healthy lifestyle.
• Manage personal administrative tasks as needed (e.g., expenses, bills, returns).

• Relationship Management and Communication:
• Serve as a liaison between the President, CEO, and internal/external stakeholders, communicating clearly, tactfully, and professionally.
• Build and maintain strong relationships across the leadership team to support smooth collaboration and decision-making.
• Ensure alignment between departments by staying on top of key conversations, decisions, and priorities.

• 5+ years of experience supporting senior executives in both business and personal capacities.
• Highly organized, proactive, and able to stay two steps ahead with excellent judgment.
• Strong emotional intelligence and diplomacy; able to protect executive time while fostering collaborative relationships.
• Comfortable working independently and ensuring tasks are completed without extensive oversight.
• Critical thinking and problem-solving abilities.
• Strong written and verbal communication skills.
• Tech-savvy, with proficiency in Microsoft 365 (Outlook, Teams, OneNote, etc.) and project management tools like Asana.
• Experience handling sensitive and confidential information with discretion.
• Comfortable using AI tools to enhance productivity.

• Detail-oriented and obsessed with organization.
• Adaptable, proactive, and resourceful in handling dynamic priorities.
• Genuine, trustworthy, and capable of maintaining strict confidentiality.
• Collaborative yet capable of operating independently.
• Adaptable and calm under pressure, with the ability to juggle multiple priorities.

Why Join Us?

At American Tall, we take care of our employees and strive to create an environment where you can flourish. When you join our team, you'll enjoy a comprehensive range of benefits designed to support your personal and professional development.

Healthy Lunch Program (onsite only): Enjoy delicious and nutritious meals curated by our personal chef, promoting a healthy lifestyle. Meals are $2 a day and all proceeds go to charity. Vegan and gluten free options are available.

Annual Performance Bonus: Your hard work and dedication are rewarded with an annual bonus, reflecting your contributions to our success.

RRSP Matching: Plan for your future with our RRSP matching program, helping you build your retirement savings.

Health Benefits: We offer comprehensive health benefits for both single employees and families, ensuring you and your loved ones are well taken care of.

Tuition Reimbursement Program: We support professional development. We will reimburse up to $1000 a year for courses taken outside of work to further develop your skills.

Generous Vacation Package: We value work-life balance and offer a generous vacation package, complete with additional gifted days off to give you the time off you deserve.

Professional Headshots: Start your journey with us on the right foot! All new hires on site are invited to receive a professional photoshoot to capture their best side.

Community Engagement: We are committed to giving back. Our lunch program supports philanthropic initiatives that benefit the community.

Office Celebrations & Social Events: Experience the joy of working in a vibrant environment with regular office celebrations and in-person socials to connect with your colleagues.

Flexible Work Hours: We understand the importance of flexibility and offer work hours that can accommodate your personal schedule when needed.

Referral Program: Help us grow our team! Receive rewards through our referral program when you bring in great talent.

Employee Discounts: Enjoy a 50% discount on our entire online collection.

Accommodations and Accessibility:

American Tall provides employment accommodation during the recruitment process. Should you require any accommodation, please indicate this on your application and we will work with you to meet your accessibility needs. For any questions, suggestions, or required documents regarding accessibility in a different format, please contact us at HR@americantall.com

Inclusion:

At American Tall, we are committed to building an environment where everyone feels included, valued, and heard. Diversity, inclusion, and belonging are an important part of our everyday work, and it is our belief that they enable us to reach our goal of providing excellent quality and care in our products. We strongly encourage applications from Indigenous peoples, racialized people, people with disabilities, people from gender and sexually diverse communities and/or people with intersectional identities.