Executive/Personal Assistant Hybrid

Keep is a Canadian fintech providing cross-border banking services for businesses, including credit cards, deposit accounts, currency conversions, and revenue financing. They are hiring an Executive/Personal Assistant to support the CTO by running day-to-day administrative, communication, scheduling, and logistics operations. The purpose of the role is to remove friction and proactively manage priorities so the CTO can focus on building and leading.

• Manage the CTO’s inbox: triage, respond to routine items, flag urgent issues, and ensure follow-through
• Follow up with third parties, vendors, and stakeholders and route requests to the right team members
• Handle sensitive and confidential communications with discretion
• Own calendar management: schedule/reschedule, resolve conflicts, and optimize time
• Coordinate meetings across multiple time zones with internal and external stakeholders
• Prepare meeting agendas/materials and manage follow-ups
• Support all-hands meeting logistics and coordination
• Book and manage travel (flights, hotels, ground transport) and create detailed itineraries
• Handle last-minute travel changes and coordinate logistics for events/offsites
• Process payments, expense reports, and administrative paperwork
• Manage contract logistics and route legal documents appropriately
• Support personal tasks/errands and local coordination as needed
• Use the company virtual card for authorized expenses only

• 4+ years of Executive Assistant or Personal Assistant experience supporting C-suite executives (preferably CTO/CEO/founders)
• Exceptional English communication skills (written and verbal)
• Extreme attention to detail and strong organizational skills
• Proactive self-starter who anticipates needs and takes initiative
• Highly responsive with excellent follow-through
• Expert-level calendar management across complex, competing priorities
• Comfortable handling both professional and personal assistant duties
• Located in Miami or willing to relocate and able to meet in person 1–2 times per week
• Excellent judgment handling confidential information

Nice to have:

• Experience in fast-paced startup or tech environments
• Experience supporting technical leaders (CTOs, VPs of Engineering)
• Familiarity with contract and legal document processes
• Event coordination experience
• Miami-area knowledge and network

• Hybrid role based in Miami with in-person collaboration 1–2 times per week
• Typical schedule 9am–5pm with occasional flexibility for after-hours communication
• Competitive salary
• Comprehensive health benefits
• Flexible hybrid work model
• Professional development opportunities
• Direct partnership with the CTO and exposure to executive leadership
• Dynamic, fast-paced environment