Executive/Personal Assistant Hybrid

Keep•Miami, FL

3h•Hybrid

About The Position

At Keep, we embarked on a mission with a powerful question: Why hasn't the banking experience caught up with the rapid pace of technology? This continues to fuel our passion for reshaping the Canadian fintech landscape. We provide businesses with a comprehensive suite of cross-border banking services, offering everything from credit cards to deposit accounts, currency conversions, and revenue financing. With a team of seasoned global startup veterans with successful exits, Keep is committed to leading the charge as Canada's next-generation fintech institution. Backed by VCs in the fintech sector, we're racing ahead, expanding our reach and impact like never before. We're looking for an exceptional Executive Assistant who will be the right hand to our CTO. This isn't your typical EA role - you'll manage everything from inbox zero and calendar optimization to travel logistics and personal tasks. You'll anticipate needs before they're asked, solve problems before they become issues, and keep everything running smoothly so our CTO can focus on building and leading. This is a part-time hybrid role (20 hours per week) based in Miami, with in-person collaboration 1-2 times per week.

Requirements

4+ years of Executive Assistant or Personal Assistant experience supporting C-suite executives (preferably CTO, CEO, or founders)
Experience in fast-paced startup or tech environments - this is essential
Exceptional English communication skills - both written and verbal
Extreme attention to detail - you catch things others miss and nothing slips through the cracks
Proactive self-starter who takes initiative and anticipates needs before being asked
Highly responsive with excellent follow-through
Expert-level calendar management with complex, competing priorities
Comfortable with both professional and personal assistant duties
Located in Miami or willing to relocate - must be able to meet in person 1-2x per week
Excellent judgment with confidential information
Comfortable with part-time schedule (20 hours per week)

Nice To Haves

Background supporting technical leaders (CTOs, VPs of Engineering)
Familiarity with contract and legal document processes
Event coordination experience
Miami area knowledge and network

Responsibilities

Inbox & Communication Management: Own and manage the CTO's inbox - triage, respond to routine items, flag urgent issues, and ensure nothing falls through the cracks Follow up with third parties, vendors, and stakeholders Route tasks and requests to appropriate team members Handle sensitive and confidential communications with discretion
Calendar & Meeting Coordination: Master calendar management - schedule, reschedule, optimize, and manage conflicts seamlessly Coordinate meetings across multiple time zones with internal and external stakeholders Prepare meeting agendas, materials, and follow-ups Assist with all-hands meeting logistics and coordination
Travel & Logistics: Book and manage all travel arrangements - flights, hotels, ground transportation, itineraries Create detailed travel plans and handle last-minute changes seamlessly Coordinate logistics for company events and offsites
Administrative & Personal Support: Process payments, expense reports, and administrative paperwork Manage contract logistics and route legal documents appropriately Support personal tasks and errands as needed (forms, problem-solving, local coordination) Use company virtual card for authorized expenses only