Executive Assistant & Personal Assistant to the CEO

Dokainish & Company • Toronto, ON

6d • Onsite

About The Position

Dokainish & Company, a world-class professional consultancy service provider since 2011, specializes in delivering impactful results across various business functions including Project Management, Quantitative Risk Analysis, Organizational Change Management, Project Controls, Enterprise Reporting, Estimating, Asset Management, and System Implementation for Capital Projects. As a fast-growing organization, we are seeking a Senior EVM & COBRA Specialist. The Executive & Personal Assistant to the CEO is a critical support role, acting as the CEO's right hand. This position requires a highly capable professional who can keep pace with an entrepreneurial leader operating across multiple business lines, time zones, and jurisdictions. This is not a traditional desk-based role; the assistant will be on-the-go with the CEO, managing both professional and personal tasks with the same level of professionalism and care. The role demands exceptional discretion, a proactive mindset, and the ability to anticipate needs. It is ideal for someone who thrives in fast-paced, high-trust environments and takes pride in ensuring a busy executive's life runs smoothly. The position is full-time, based in Toronto, Ontario, requiring in-person and on-the-go support as needed, and reports directly to the CEO. A valid driver's license and access to a reliable personal vehicle are required.

Requirements

• 2-4 years of experience in an executive assistant, personal assistant, or similar high-trust administrative support role.
• Valid driver’s licence and access to a reliable personal vehicle (required).
• Proficiency in Microsoft Office Suite (Outlook, Word, PowerPoint, Excel).
• Exceptional organizational and time management skills; able to manage multiple competing priorities with composure.
• Strong verbal and written communication skills in English.
• High degree of professionalism, discretion, and sound personal judgment.
• Comfortable operating in a fast-paced, entrepreneurial environment with limited day-to-day structure.
• Ability to work independently and proactively, with a strong sense of personal accountability.
• Positive, flexible attitude; genuinely embraces variety; no task is too small and no challenge too unfamiliar to figure out.
• Must be based in or able to commute to downtown Toronto; this is a full-time, in-person role.

Nice To Haves

• Prior experience supporting a CEO, founder, or senior executive in a professional services or consulting environment.
• Exposure to multi-jurisdictional or international business operations.
• Familiarity with travel coordination across international destinations including the Middle East.
• Experience managing both professional and personal responsibilities for an executive.

Responsibilities

• Manage the CEO’s calendar as needed: booking meetings and appointments, and day-of coordination.
• Draft, review, and manage professional correspondence and communications on behalf of the CEO.
• Prepare briefing materials, agendas, and meeting notes for internal and external engagements.
• Coordinate domestic and international travel: flights, accommodations, ground transportation, visas, and detailed itineraries.
• Liaise with clients, partners, internal staff, and external stakeholders on behalf of the CEO.
• Track outstanding action items and follow up on deliverables to ensure the CEO’s commitments are met.
• Support preparation of presentations, proposals, and executive-level documents as needed.
• Manage CEO expense reporting and reconciliation.
• Serve as a reliable point of contact when the CEO is unavailable or travelling.
• Provide personal scheduling and logistical support including appointments, reservations, and personal errands.
• Coordinate personal travel and family-related logistics as needed.
• Manage personal vendor relationships and household service appointments on an ad-hoc basis.
• Run time-sensitive personal errands, including driving when required.
• Handle all personal matters with full confidentiality and professionalism.
• Support special initiatives and one-off projects as directed by the CEO.
• Adapt to shifting priorities and a highly varied day-to-day workload without losing momentum.
• Contribute to the broader team in a variety of ways as company needs evolve.

Benefits

• Visibility: work directly with and for the CEO of a scaling global firm, with impact felt every day.
• Culture: values excellence, initiative, and genuine collaboration.
• Open communication, accountability, trust, and respect.
• Opportunity to grow alongside a company on the move.

What This Job Offers

• Job Type: Full-time
• Career Level: Executive
• Education Level: No Education Listed