Job Description
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.
About the role
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.
What you’ll do
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
About you
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
What makes an A-player in this role
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
What to expect
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 with the CTO 1-2x per week
Preparing materials for all-hands meetings
Solving unexpected problems as they arise
Work schedule:
Typical 9am-5pm schedule with occasional flexibility for after-hours communication
Hybrid: In-office 1-2 days per week, remote the rest
What we offer
Competitive salary
Comprehensive health benefits
Flexible hybrid work model
Professional development opportunities
Direct partnership with CTO and exposure to executive leadership
Dynamic, fast-paced environment where you’ll make real impact
Want to Learn More?
Head over to our webpage to discover more about us. Take a peek at our Glassdoor profile to see what our Keepers are saying, and stay tuned for exciting updates on our LinkedIn page and learn about our values and benefits on our career page.
Commitment to Diversity and Inclusion
Keep provides equal employment opportunities (EEO) to all employees and applicants for employment without regard to race, color, religion, sex, national origin, age, disability, genetics, sexual orientation, gender identity, or gender expression. We are committed to a diverse and inclusive workforce and welcome people from all backgrounds, experiences, perspectives, and abilities.
