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Personal Executive Assistant

53 minutes ago

Toronto, Canada CSC Generation Full time

Be among the first 25 applicants CSC Generation is an AI-native holding company re-engineering omni-channel retail. We acquire iconic brands and transform them with Genesis—our operating platform combining a data fabric, automation engine, proprietary tools, and shared services—to modernize operations, elevate customer experience, and expand margins. With more than $1B in revenue across 13 brands, our portfolio includes Sur La Table, Backcountry, One Kings Lane, and others that serve as real-world innovation labs. We’re hiring a Personal Executive Assistant to support our CEO. This is not a traditional EA role focused only on gatekeeping and travel booking. It’s a high-leverage, systems-driven role for someone who loves using technology (especially AI/automations) to keep a complex life and calendar running smoothly—often beyond standard business hours. You must be detail oriented, quick, available, adaptable and comfortable with constant change in a fast-paced environment. This is a contract position at $34/hour, starting at ~20 hours/week during a probationary period, with the potential to convert to full-time (40–50 hours/week) if there is a mutual fit. LinkedIn profile must be on resume or application to be considered. Please read job description closely before applying & only apply if you believe you're a good fit for this role. What You'll Do Own a very dynamic calendar. Manage a heavy volume of meetings across time zones. Book, rebook and cancel meetings as priorities change. Communicate changes. Run the CEO’s day like a control tower. Send/schedule daily schedules and reminders before each block of meetings, including “prep now,” “join in 5 minutes,” and “leave now” nudges. Time management for in-person meetings (max ~3 per week). Track traffic and transit time so that reminders reflect when to leave, not just when a meeting starts. Adjust alerts if conditions change and build simple automations so this process gets smarter over time. Travel & flight management. Track flights, typical security wait times, and airport busyness using available tools. Recommend when to leave, how much buffer to add, and proactively flag risks (weather, delays, tight connections). Occasionally change flight or seat. Use AI and automation to increase leverage. Apply tools like ChatGPT, Claude, Gemini, and others to draft communications, summarize information, create checklists, and streamline scheduling workflows. Set up and maintain simple automations (rules, zaps, shortcuts, scripts, etc.) that reduce repetitive work and help the CEO stay on track. Keep communication and follow-through tight. Track decisions, follow-ups, and priories in a shared note with CEO. Nudge the right people at the right time to keep things moving. Who You Are Calendar and time management is your superpower. You have experience managing a high-volume, frequently changing calendar for a senior leader, founder, or equivalent. You’re comfortable creating calendar invites across Outlook & Google Calendars and adjusting on the fly. AI-curious and automation-minded. You already use AI tools (e.g., ChatGPT, Claude, Gemini, n8n, Zappier & etc.) in your work or personal life. You enjoy experimenting with new tools, setting up automations, and continuously improving your systems. Candidates who do not use or fundamentally don’t want to use AI tools will not be a culture fit for this role. Comfortable with non-traditional hours. You understand that supporting an executive sometimes means after-hours and occasional weekend availability for urgent changes, travel issues, or priority shifts. Responsiveness is CRITICAL for this role. High judgment: you know when to ask vs. when to act. You’re comfortable asking clear, concise questions when context is missing. You know when to pause and clarify versus when to take a best‑effort step and move things forward. You’re proactive without being reckless. Organized, precise, and discreet. You notice small details that prevent big problems. You handle sensitive information with confidentiality and professionalism. You communicate clearly and succinctly in writing and verbally. Thick‑skinned and low-ego. You’re comfortable with direct, candid feedback and fast‑paced, sometimes blunt communication. You don’t take things personally, you recover quickly from changes or mistakes, and you focus on fixing the problem and moving forward. Salary : $34 an hour The CSC family of brands provides equal employment opportunities to all employees and applicants for employment and prohibits discrimination and harassment of any type without regard to race, color, religion, age, sex, national origin, disability status, genetics, protected veteran status, sexual orientation, gender identity or expression, or any other characteristic protected by federal, provincial, state or local laws. The CSC family of brands is committed to providing reasonable accommodations for qualified individuals with disabilities in our job application procedures. If you need assistance or an accommodation due to a disability, please contact (email protected) . We may use artificial intelligence (AI) tools to support parts of the hiring process, such as reviewing applications, analyzing resumes, or assessing responses. These tools assist our recruitment team but do not replace human judgment. Final hiring decisions are ultimately made by humans. If you would like more information about how your data is processed, please contact us. Seniority level: Mid‑Senior level. Employment type: Contract. Job function: Administrative. #J-18808-Ljbffr