Personal Assistant and Executive Assistant to the CEO

Executive Assistant & Personal Assistant to the CEO 

About Dokainish & Company

Since 2011 Dokainish & Company has been providing world class professional consultancy services.

We specialize in working diligently and collaboratively with our clients to achieve long-lasting and impactful results across numerous business functions. Our areas of expertise include, but are not limited to, Project Management, Quantitative Risk Analysis, Organizational Change Management, Project Controls, Enterprise Reporting, Estimating, Asset Management, and System Implementation for Capital Projects. We draw upon decades of project experience to deliver customized solutions to our clients’ most complex challenges.

We are a fast-growing organization, currently seeking a Senior EVM & COBRA Specialist to support the delivery of complex capital projects through rigorous cost and schedule performance management.

Role Overview

The Executive & Personal Assistant to the CEO is one of the most important support roles in our organization. This person serves as the CEO’s right hand; a trusted, highly capable professional who keeps pace with a fast-moving, entrepreneurial leader operating across multiple business lines, time zones, and jurisdictions.

This is not a traditional desk-based EA role. The CEO operates dynamically; across the office, client sites, business meetings, and personal engagements, and this role moves with him. The right person will be equally at ease managing a board-level briefing package and handling a last-minute personal errand and will treat both with the same level of professionalism and care.

This role requires exceptional discretion, a proactive mindset, and the ability to anticipate needs before they are voiced. If you thrive in fast-paced, high-trust environments and take pride in making a busy executive’s life run smoothly, this role is for you.

Location:  Toronto, Ontario: in-person and on-the-go with the CEO as needed

Type:  Full-time

Reports to: CEO

Requirement: Valid driver’s licence and access to a reliable personal vehicle

Who We Are Looking For

The ideal candidate for this role is not defined by years of experience alone; it’s defined by who they are. We are looking for someone who:

• Is genuinely proactive; you don’t wait to be told; you anticipate, prepare, and act.

• Has high emotional intelligence. You know when to ask, when to act, and when to just take care of it.

• Is discreet. You will be trusted with confidential professional and personal information, and you treat that trust as non-negotiable.

• Adapts quickly. No two days look the same and you are energized, not unsettled, by that.

• Takes ownership. You follow through on everything, big and small, and nothing gets dropped.

• Is comfortable operating in ambiguity. Direction may be minimal at times and you’re able to use good judgment to fill in the gaps.

• Has no ego about task type. You move fluidly between drafting an executive briefing and picking up dry cleaning, because both matter.

• Is a warm, polished communicator; someone the CEO’s clients, contacts, and family feel comfortable interacting with.

Key Responsibilities

Executive Support

• 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.

Personal Assistance

• 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.

Ad Hoc & Special Projects

• 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.

Note: This role description is intended to provide a general overview of the position. It is not an exhaustive list of all responsibilities, duties, skills, or qualifications required.

What Success Looks Like

Success in this role isn't measured by completing a task list, it's measured by how well the CEO can focus on leading the business. The right person will build trust quickly, learn the rhythm of how he operates, and move from executing instructions to anticipating needs. Over time, you become a genuine extension of him: someone who exercises good judgment when direction is incomplete, handles the unexpected without losing composure, and makes a fast-moving CEO leading a growing global consultancy feel organized, supported, and free to do the work only he can do. The team knows they can reach you when they can't reach him, and nothing gets dropped. That is this role at its best.

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 Have

• 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.

Why Join Us

At Dokainish & Company, you’ll be joining a team that values excellence, initiative, and genuine collaboration. This is a role with real visibility; you will work directly with and for the CEO of a scaling global firm, and your impact will be felt every day. We recognize and value the uniqueness of every individual on our team and foster a culture of open communication, accountability, trust, and respect.

If you are looking for a role where no two days are the same, where your contributions matter, and where you can grow alongside a company on the move, we want to hear from you.

Notes

VACANCY STATUS: This posting is for a new position.

AI USAGE: This organization does not use artificial intelligence to screen, assess, or select applicants for this particular open position. All applications are personally reviewed by our Talent Acquisition Team.

Dokainish & Company is an equal opportunity employer. Qualified applicants will receive consideration for employment without regard to age, gender, race, colour, religion, sexual orientation, gender identity, national origin, disability, age and veteran status, or any other protected status required by applicable law.

In accordance with the Ontario Human Rights Code, Accessibility for Ontarians with Disabilities Act, 2005, and Dokainish & Company AODA Policy, accommodation will be provided in all parts of the hiring process. Applicants need to make their needs known in advance.