Executive/Personal Assistant Remote

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.

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 (primarily US-based)

• 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 remotely (forms, coordinating services, problem-solving)

• Use company virtual card for authorized expenses

About you

Required:

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

• Native or near-native English proficiency (C1/C2 level) - you communicate as clearly in English as in Spanish

• Proven remote work experience successfully supporting US executives with full time zone overlap

• 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 despite working remotely

• Expert-level calendar management across time zones with complex, competing priorities

• Comfortable with both professional and personal assistant duties

• EST/CST time zone overlap - your working hours align with Miami time

• Excellent judgment with confidential information

• Reliable internet and professional home office setup

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

• Previous experience with US-based companies in LATAM remote roles

• EST time zone preferred

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 despite working remotely

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

• Excels at remote work - you're self-motivated, over-communicate, and create structure for yourself

What to expect

Day-to-day:

• Morning inbox triage and calendar optimization (aligned with EST hours)

• Coordinating meetings and handling schedule changes

• Following up on pending contracts and administrative tasks

• Booking travel and managing logistics

• Coordinating services or tasks remotely for the CTO

• Preparing materials for all-hands meetings

• Video check-ins with the CTO as needed

• Solving unexpected problems as they arise

Work schedule:

• Typical 9am-5pm EST schedule (aligned with Miami time)

• Occasional flexibility for after-hours communication

• Fully remote with strong internet connection required

What we offer

• Competitive LATAM salary

• Professional development opportunities

• Direct partnership with CTO and exposure to executive leadership

• Dynamic, fast-paced environment where you'll make real impact

• Work with a US tech company while maintaining work-life balance in your country

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.