Executive Operations Manager

Overview

We're a managed service provider (MSP) that's served Toronto businesses for 20 years. Our mission: help small and medium businesses get great IT support, keep their data safe, and focus on their business - not IT.

We provide comprehensive IT management for small to medium businesses, including helpdesk support, cybersecurity, network deployments, and emergency incident response. We serve clients who face sophisticated cyberattacks but can't afford in-house IT teams, delivering enterprise-level support at a fraction of the cost with 15-minute average response times.

Our clients range from 10-person businesses to enterprise organizations like Mejuri and Priceline across architecture, professional services, and communications industries. While most clients are located in Toronto's downtown core, we serve businesses across Canada and maintain international partnerships. We're expanding our service offerings to include AI and automation consulting.

We achieved 60% growth 2024and are focused on sustainable 30% growth this year with a new marketing strategy. Over 250 companies trust our services with a 99% client retention rate. Team members typically stay 6-11 years with us, reflecting our strong company stability and employee satisfaction.

Our Company Values

• 🤝 Play as a Team
• Keep Growing
• Adapt and Evolve

We're a hybrid organization with 5 (soon to be 6 ) teammates, including 2 Helpdesk Specialists, 1 Project Coordinator handling invoicing and vendor procurement, 1 Cybersecurity Expert, and our CEO. We're headquartered in downtown Toronto at Yonge and Bloor in a premium co-working space, with one team member working remotely from Regina, Saskatchewan.

Our culture balances high expectations with trust - no micromanagement, but we expect rock star performance. We support each other and stand up to clients who disrespect our staff. Connection happens through daily Google Chat and weekly Monday calls that cover work updates plus personal check-ins. We celebrate with annual team events, Christmas dinners at the CEO's house, and personalized gifts.

About the Role

We're looking for a remote Executive Operations Manager who operates as an extension of the CEO's thinking—not traditional support, but true leverage. This isn't about being helpful; it's about reducing decision fatigue, protecting executive attention, and independently converting vague ideas into execution. The CEO is managing burnout and needs someone who drafts solutions instead of asking questions, batches interruptions ruthlessly, and operates with minimal direction.

In this role, you'll own the CEO's operational ecosystem with one mission: free up two full days per week of executive time for strategic work while ensuring nothing falls through the cracks. You'll anticipate needs based on calendar patterns, surface team blockers with drafted solutions, and handle 75% of your scope autonomously by month 6—bringing the CEO options to react to, not problems requiring instruction.

This role has a clear growth path to Chief of Staff for the right person. You'll have access to sensitive information that could make or break the company. You'll also represent our company with clients when needed, requiring sound judgment and Canadian business cultural fluency.

Our IDEAL CANDIDATE

br brings 6+ years of experience in Executive Assistant, Corporate Secretary, or Chief of Staff roles. You have exceptional memory and pattern recognition—the CEO never repeats themselves with you. You draft first, ask never: given "We should do more on LinkedIn," you produce 3-5 drafted posts with stated assumptions, not clarifying questions. You batch questions ruthlessly into one daily touchpoint. You're comfortable disagreeing respectfully when you spot risks. You're comfortable being occasionally wrong in service of speed rather than paralyzed by perfectionism. You communicate with clear, professional English and neutral accent suitable for Canadian business owners.

Reporting Structure: You'll collaborate with our entire team and work closely with our Project Coordinator, with occasional client-facing responsibilities. This position reports directly to the CEO.

You’ll be doing things like:

• Inbox & Communication Management: Clean inbox daily and deliver executive summary by 9AM; draft responses without asking "What should I say?" (bring CEO something to react to); batch questions into one daily touchpoint; triage emails and ghostwrite on behalf of CEO; schedule meetings with context alerts; maintain inbox zero; package information concisely to reduce cognitive load
• Strategic Research & Analysis: Turn vague directives like "We should do more on LinkedIn" into drafted options with stated assumptions; lead research proj