Executive​/Personal Assistant Hybrid

Our Journey at Keep

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 hybrid role based in Miami, with in-person collaboration 1-2 times per week.

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

Required:

• 4+ years of Executive Assistant or Personal Assistant experience supporting C-suite executives (preferably CTO, CEO, or founders)

• 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

Nice to have:

• Experience in fast-paced startup or tech environments

• Background supporting technical leaders (CTOs, VPs of Engineering)

• Familiarity with contract and legal document processes

• Event coordination experience

• Miami area knowledge and network

You're the kind of person who:

• Anticipates needs before they're expressed

• Loves solving problems and removes obstacles without being asked

• Thrives on variety - no two days are the same and you love it

• Has great attention to detail - nothing gets by you

• Makes confident decisions even with incomplete information

• Stays calm under pressure - last-minute changes don't phase you

• Communicates proactively - you flag issues early and keep your exec informed

• Takes ownership - if something needs doing, you make it happen

Day-to-day:

• Morning inbox triage and calendar optimization

• Coordinating meetings and handling schedule changes

• Following up on pending contracts and administrative tasks

• Booking travel and managing logistics

• Handling personal errands and problem-solving

• Meeting in-person…