Executive Operations Manager (IT Services | CEO Right Hand, Executive Assistant | Operations, [...]

Goodwork; Colombia; Presencial; COP 61.126.008 - 83.372.753; Jornada completa

Ventajas ofrecidas por este puesto de trabajo

Work from home with full remote setup

Competitive compensation for the international market

Learning and growth opportunities

Descripción de la vacante

A leading managed service provider in Colombia seeks a Remote Executive Operations Manager to transform vague directives into actionable solutions while supporting the CEO. This role requires at least 6 years of executive support experience, advanced proficiency in AI tools, and expert knowledge in Google Workspace. Candidates who excel will have opportunities for significant growth, including a clear path to Chief of Staff. The position offers competitive compensation and allows for a full remote setup.

Formación

• 6+ years of experience in Executive Assistant, Corporate Secretary, or Chief of Staff roles.
• Exceptional memory and pattern recognition.
• Strong, clear English with neutral accent suitable for Canadian business owners.

Responsabilidades

• Manage CEO's emails and communications efficiently.
• Conduct strategic research and present actionable insights.
• Develop processes and document decisions for future reference.

Conocimientos

Executive support experience

Draft-first mentality

Advanced AI proficiency

Expert-level Google Workspace skills

Educación

Undergraduate degree or relevant work experience

Herramientas

Google Workspace

Asana

Descripción del empleo

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 projects and present recommendations with analysis, not raw data; preprocess information into decision-ready summaries; operate with increasing autonomy (target 75% by month 6, requiring minimal daily direction); respectfully challenge CEO when you spot risks or better approaches; anticipate needs based on calendar patterns
• Process & Systems Development: Build organizational handbooks and SOPs; consolidate scattered information into coherent systems; use AI tools to identify and fill process gaps; create memory systems so CEO doesn't repeat context; document decisions for future reference; conduct quality checks on existing processes
• Team Coordination & Accountability: Monitor team assignments and deliverables; hold teammates accountable; support Project Coordinator with vendor coordination; manage CEO's task list and ensure nothing falls through; surface team blockers with drafted solutions; act as CEO's accountability partner
• Client Relations & Business Development: Schedule client status meetings and touchpoints proactively; maintain CRM and client contact information; follow up on CEO networking commitments; represent company professionally when CEO unavailable; handle client communications with Canadian business cultural fluency; coordinate client retention initiatives
• Financial & Administrative Operations: Conduct monthly cloud account audits and identify cost savings; track service pricing and vendor offerings; handle light financial admin; answer business line calls and triage appropriately; organize team events and 1:1 meetings
• Marketing & AI-Powered Content: Create LinkedIn content using AI tools (draft 3-5 posts from vague directives like "talk about AI in MSPs"); explain reasoning and suggest posting cadence; collaborate with CEO to refine messaging; manage posting schedule; use CustomGPTs to accelerate drafts
• Personal Support (10%, decreasing over time): Coordinate travel arrangements; handle limited short-term personal tasks; manage occasional communication for two quadplexes and Airbnb unit

Skills & Qualifications

• 6+ years of experience in Executive Assistant, Corporate Secretary, Chief of Staff, or similar executive support roles
• Draft-first mentality: Turn vague directives into options with stated assumptions, not clarifying questions
• Low interruption style: Batch questions into single touchpoints; protect executive attention
• Comfortable disagreeing respectfully: Challenge assumptions when you spot risks or better approaches
• Advanced AI proficiency: Daily ChatGPT usage, custom GPT creation, workflow optimization
• Expert-level Google Workspace and project management tools (Asana preferred)
• Strong memory and pattern recognition: Remember context so the CEO doesn't repeat themselves
• Old-fashioned work ethic: No excuses, take pride in your work, get things done
• Professional empathy: Pick up on the CEO's priorities; know when to handle independently vs. escalate
• Strong, clear English with neutral accent suitable for Canadian business owners

Bonus if you also have:

• Background in IT service firms or technical troubleshooting
• Deeper AI and automation experience beyond ChatGPT
• Track record with high-growth startups or scaling companies
• Experience supporting executives with ADHD or high-energy leadership styles
• Familiarity with our tools: Google Workspace (Gmail, Google Chat), Zoom business line, ChatGPT, Loom, Halo helpdesk ticketing, Asana, VPNs

Working Hours

Fixed - 8:30AM-4:30PM ET (Eastern Time). Changes with Daylight Savings Time.

Full-time vs Part-time: Full-time (40 hours/week)

Education: An undergraduate degree, or relevant work experience

Level: Intermediate (3-5 years of relevant work experience)

Compensation: ~CAD $2,036-$2,777 (COP 5.5M-7.5M) per month, based on experience. Structured as a Consultant Agreement (independent contractor), meaning you'll be responsible for your own taxes, benefits, and insurance.

Benefits of working with us:

• 🚀 Work directly with a forward-thinking Canadian MSP focused on strategic, sustainable growth
• 🏡 Work from the comfort of your home with full remote setup
• 🏆 Join an incredibly talented, close-knit team with exceptional retention (6-11 year tenure)
• 🧘🏾♀️ Work-life balance: 8 hours a day, 5 days a week with fixed hours
• 💰 Competitive compensation for international market
• 💻 Remote-first company culture with premium tools and technology
• 🧠 Learning & growth opportunities as first Executive Operations hire with clear path to Chief of Staff
• 📞 Direct connection with leadership through daily Google Chat and Google Meet
• 📊 Weekly Monday status calls for alignment and personal support
• 🎁 3 personal days annually plus 2 weeks vacation (increasing with tenure)
• 🤝 3-4 days bereavement leave and mental health support