Executive Assistant to CEO

Seeking a driven, tech-savvy Executive Assistant to the CEO to manage high-level projects, communications, and day-to-day operations for multiple growing ventures. If these ventures grow, you'll have opportunities to take on greater responsibility, learn new skills, and tackle bigger projects. If you're organized, adaptable, and excited by the idea of continuous learning in a dynamic environment, this role could be a great fit.

What the role actually does:

1. Own the executive's calendar
2. Take a lead role in the executive's communication with external stakeholders-vendors, clients, partners, etc, working up to being the first line of defense for his inboxes.
3. Travel: Arrange all travel; flights, accommodation, local transport, etc; adapt swiftly to changes or urgent travel requirements; maintain an updated passport and be prepared to travel with the executive if necessary (this should be exceedingly rare).
4. Oversee a wide range of administrative tasks, including filing, expense tracking, and coordinating tax preparation with an accountant.
5. Organize and maintain digital and physical files. Create, maintain, and train others as needed on systems for organization.
6. Research is a significant part of the role. Investigate unfamiliar topics, compile relevant data, and present findings in documents. Be comfortable using AI/LLM tools like ChatGPT to support this. Here's some examples of potential requests that might require research and action following the outcome of the research:
7. Setting up a simple website using a platform like Wix.
8. Creating a list of investment funds that meet specific criteria.
9. Identifying marketing firms specializing in certain industries and ranking them by custom criteria.
10. Provide light technical support (e.g., basic troubleshooting of printers or routers); I am very tech savvy but want to share the workload and have fairly high expectations for technical aptitude.
11. As needed, screen and coordinate with external contractors or freelancers (e.g., from Fiverr, Upwork) for various tasks as needed; not very common. Ensure timely delivery of outsourced work, following up on quality and deadlines.
12. Serve as a jack-of-all-trades as needed for the executive's businesses.

Things you are into or good at that would help:

1. Tools: Enthusiasm for learning new tools, platforms, or methods and tackling unfamiliar tasks. It'd be nice if you were excited about trying out new software and learning it for fun. Comfortable using common office software (email, calendars, spreadsheets) and AI-based platforms.
2. Project management: Proven ability to manage multiple projects and priorities with meticulous attention to detail. Adept at setting up and maintaining systems that keep information organized and accessible.
3. Communication: Strong written and verbal skills in English (native proficiency not required, though the executive is a native English speaker). Value clear direct communication
4. Remote ready/flexible: Able to work both remotely and in an office in/near Port Williams
5. Travel: Have a valid passport or able to obtain one promptly; open to travelling as needed (this should be very rare)
6. Discretion: Be able to keep confidential things confidential. No gossiping, etc.
7. About us / the companies / the role:
8. Growth opportunities: learn new skills, use new tools, and take on increasingly complex responsibilities
9. Flexibility: flexible schedule, no annoying office dress code, paid time off; be responsive when needed but there's a lot of flexibility.
10. Collaborative: work with someone who values initiative, creativity, continues improvement
11. Independent thinkers: I hold strong, sometimes unconventional views and may express opinions that don't align with popular sentiment. Don't apply if that's a problem for you.
12. Commitment: Sometimes it'll be "go time" and there's going to be unlimited work to do in a short amount of time. I expect you to step up and deal with it when those times come. If we plan well, they won't happen very often.

Submit your resume and a brief explanation of why you'd be a great fit. Please don't apply if you think anything in this listing is a "red flag" to you. It'll save us both time. I look forward to hearing from you!