Executive and Personal Assistant

EXECUTIVE AND PERSONAL ASSISTANT
Toronto-based IT and Cybersecurity Firm | Full-Time | USD $1,200/month | Start: Second week of June 2026

WHO WE ARE
We are a small, five-person IT and cybersecurity firm based in Toronto, Canada. We manage the technology for professional services companies, including law firms, architecture studios, and tech startups.

The CEO you will be working directly with is entrepreneurial and fast-moving. He is not a micromanager. He will give you real responsibility from day one and trust you to run with it. In a team this size, good work is visible and recognized quickly.
We treat remote tea ---------- mbers as real tea ---------- mbers. You will have direct access to the CEO, regular check-ins, and genuine investment in your growth. We want this to be a role you stay in and grow with, not a stepping stone.
This is a role for someone who wants ownership, not a job description.

THE ROLE
This is an Executive and Personal Assistant role with real teeth. You will be the person the CEO thinks out loud with, hands things off to, and trusts to run with them. You will interact with the team, drive follow-through, flag what is slipping, and keep projects moving without being asked twice.
The CEO you support is a high-D, visionary operator who moves fast and thinks big. Your superpower is the opposite. You catch what he misses, maintain what he will not, and bring order to his chaos. If you are energized by being the detail-oriented counterpart to a fast-moving leader, this role was built for you.
This person will be in meetings, on calls, and across documents with the CEO daily. They will retain details, anticipate needs, and have information ready before it is asked for. If the CEO is heading to a client site, the address, suite number, contact name, and reason for the visit are already in his calendar before he asks.
The split is roughly 80% business and 20% personal, with approximately 20% of your time also supporting other tea ---------- mbers.

Hours: 9am to 5pm Eastern Time during onboarding (60 to 90 days), then shifting to 7am to 3pm ET.
This role has no ceiling. The more capable and proactive you are, the more responsibility you will earn.

WHAT YOU WILL DO
Execution and Follow-Through

Receive direction and ideas from the CEO and turn them into moving parts
Coordinate with tea ---------- mbers to make sure tasks are assigned, understood, and completed
Track open items, follow up without being asked, and bring back status updates, not problems
Maintain accountability on internal projects and process builds
QA on internal processes to ensure steps are not skipped

Communications and Inbox

Own the CEO inbox, triage, prioritize, and draft replies to near-send quality
Target: CEO clicks send without editing 8 out of 10 times
Screen and route incoming calls as a warm, professional first point of contact
Manage calendar, schedule meetings, and coordinate logistics
Communicate professionally with clients, vendors, and contacts on behalf of the CEO

Business Operations

Maintain and update CRM with new meetings, contacts, and follow-ups
Track client check-ins and coordinate quarterly and 6-month touchpoints
Monitor helpdesk queue and flag CEO-relevant tickets
Support internal process documentation, including SOPs, wikis, and system guides
Light project management, track open tasks, follow up on outstanding items
Coordinate with the internal team on overflow admin tasks

Marketing and Content

Draft and schedule LinkedIn and social media posts based on CEO's direction
Repurpose existing content including recordings and notes, into posts and emails
Light research on competitors, tools, and industry trends

Personal Admin and Property

Research, compare, and execute on personal tasks, including insurance, logistics, vendor negotiations, purchases, and warranty claims
Personal travel booking and logistics every 6 months
Handle vendor and provider calls on behalf of the CEO
Light coordination on investment properties and an Airbnb, including guest communication, cleaner bookings, and annual rental admin

WHO YOU ARE

Business-level English is non-negotiable. Written and spoken communication must be clean, professional, and client-ready. Western business English grammar and fluency is required, not just the ability to be understood.
You are anticipatory, not reactive. You think one step ahead and have what the CEO needs before he asks for it.
You retain details. Clients, addresses, project context, open items. You know where everything is and can retrieve it instantly without attitude.
You are detail-oriented by nature, not by effort. You catch errors, close loops, and do not let things fall through the cracks.
You take initiative. You figure things out and bring back solutions, not questions.
Smart, driven, and someone who pushes back respectfully and gets things done.
You have an entrepreneurial mindset. You have operated with ownership, managed others, or run your own venture.
You are warm, high-energy, and someone people genuinely want to work with.
You are comfortable handling both business tasks and personal admin without treating either as beneath you.
You are discreet. You will have access to personal finances, client relationships, and property matters.
You are comfortable using AI tools like ChatGPT or Claude to work faster and smarter.
You are available exclusively for this role. You may not take on other clients or employers while working with us.

WHAT WE OFFER

USD $1,200/month, full-time
Start date: second week of June 2026
Fully remote, work from home
Hours: 9am to 5pm Eastern Time during onboarding, shifting to 7am to 3pm ET once ramped
90-day trial with a structured review and compensation increase for strong performers
A role with no ceiling. Responsibilities grow with your capability.
Paid time off
Annual bonus for strong performers

TECH AND SECURITY
As a cybersecurity-focused firm, you will be required to install our standard security suite on your work computer. Your device must be used for work purposes only and not shared with household members. Full details provided upon offer.

HOW TO APPLY
Include a 2-minute video (Loom or similar) answering this question: Tell us about a time you solved a problem that was not your job. What happened, what did you do, and what was the outcome? Include the link in your application.
Also, write a short email on our behalf using this scenario: You are emailing a client to let them know their server maintenance is scheduled for this Saturday between 10pm and 2am. Reassure them that disruption will be minimal and that the team will be available if anything comes up. Paste this email directly into your application message.
Applications in which the video does not demonstrate business-level English fluency will not advance, regardless of other qualifications.

We are looking for one person who is exactly right. We will take the time to find them.

One final detail in this posting will tell us you read it carefully. Make sure your application reflects that.