Executive/Personal Assistant Hybrid (part time)

📋 Description

• • At Keep Labs Inc., we are revolutionizing the Canadian fintech landscape by addressing the critical gap between banking services and technological advancement. Our mission is to empower businesses with a comprehensive suite of cross-border banking solutions, including credit cards, deposit accounts, currency conversions, and revenue financing. Founded by a team of seasoned global startup veterans with a proven track record of successful exits, Keep is poised to become Canada's next-generation fintech leader, fueled by significant VC backing and a relentless drive for innovation and expansion.
• • We are seeking an exceptional and highly proactive Executive/Personal Assistant to provide dedicated, part-time hybrid support to our Chief Technology Officer (CTO). This is far more than a traditional administrative role; it's an opportunity to be the CTO's indispensable right hand, ensuring seamless operational efficiency and enabling them to focus on strategic initiatives and technological leadership. You will be instrumental in managing the CTO's daily workflow, from meticulously organizing their inbox and optimizing their calendar to orchestrating complex travel logistics and handling a variety of personal tasks with utmost discretion and efficiency.
• • Your primary objective will be to anticipate needs before they arise, proactively identify and resolve potential issues, and maintain a smooth, high-functioning operational environment. This role demands an individual who thrives in dynamic, fast-paced settings, possesses an extraordinary level of detail-orientation, and demonstrates impeccable judgment, especially when dealing with sensitive and confidential information. The ideal candidate will be a self-starter, capable of taking initiative and driving tasks to completion with minimal supervision.
• • Key responsibilities will encompass comprehensive inbox and communication management. This includes triaging emails, responding to routine inquiries, identifying and escalating urgent matters, and ensuring that no critical communication is overlooked. You will be responsible for following up with external parties, vendors, and key stakeholders, ensuring timely responses and progress on ongoing matters. Furthermore, you will expertly route tasks and requests to the appropriate team members, facilitating efficient cross-functional collaboration.
• • Calendar and meeting coordination will be a cornerstone of this role. You will be responsible for mastering the CTO's complex schedule, seamlessly scheduling, rescheduling, and optimizing appointments while adeptly managing conflicts. This involves coordinating meetings across multiple time zones with both internal teams and external partners, ensuring all participants are informed and prepared. You will also be tasked with preparing meeting agendas, compiling necessary materials, and distributing follow-up action items. Additionally, you will provide crucial logistical support for all-hands meetings and other significant company gatherings.
• • Travel and logistics management will be another critical area of focus. You will be responsible for booking and managing all aspects of the CTO's travel, including flights, accommodations, ground transportation, and creating detailed itineraries. The ability to handle last-minute changes with grace and efficiency is paramount. You will also coordinate the logistical intricacies of company events, offsites, and executive retreats, ensuring a smooth and successful experience for all attendees.
• • Beyond core executive support, you will provide essential administrative and personal assistance. This includes processing payments, managing expense reports, and handling various administrative paperwork with accuracy. You will also manage contract logistics, ensuring legal documents are routed appropriately and deadlines are met. A unique aspect of this role involves supporting personal tasks and errands as needed, ranging from managing forms and resolving local coordination issues to utilizing company virtual cards for authorized expenses, always adhering to company policy.
• • The ideal candidate will possess a minimum of 4 years of experience as an Executive Assistant or Personal Assistant, specifically supporting C-suite executives, preferably CTOs, CEOs, or founders. Experience within a fast-paced startup or tech environment is essential, as you will be navigating a rapidly evolving landscape. Exceptional English communication skills, both written and verbal, are non-negotiable, as is an extreme attention to detail that ensures nothing is missed. You must be a proactive self-starter who anticipates needs, demonstrates excellent follow-through, and is comfortable managing complex calendars with competing priorities. The ability to seamlessly blend professional and personal assistant duties is required. This is a part-time role (20 hours per week) requiring you to be located in or willing to relocate to Miami, with the necessity of in-person collaboration 1-2 times per week. Excellent judgment with confidential information and comfort with a flexible, part-time schedule are also key requirements.
• • A background supporting technical leaders, familiarity with contract and legal document processes, event coordination experience, and local Miami area knowledge are considered advantageous. What truly sets an A-player apart in this role is their innate ability to anticipate needs, a passion for problem-solving, a love for variety, meticulous attention to detail, the confidence to make decisions with incomplete information, the composure to remain calm under pressure, proactive communication, a strong sense of ownership, and the ability to thrive amidst ambiguity in a dynamic startup culture. You will be expected to manage your time effectively, communicate proactively despite limited hours, and ensure the CTO's operational needs are consistently met.