Personal Assistant to the Chairman

Full-time, Permanent


2 weeks ago in Administrative and Office Support

Job Description:

This rewarding and demanding role operates within our client, UHNW family office and must meet the needs of a principal who actively leads a global enterprise as Chairman and CEO, is the head of a prominent Canadian family, and has a demanding domestic and overseas travel schedule. Reporting to the CEO of the Family Office and supporting the Chairman and Executive Assistant, this critical role ensures that the principal’s administrative needs have been attended to in full, with exacting attention to detail, forethought and preemption. The Executive Assistant Team comprises two individuals in Canada and a further team member in the UK who work in partnership. The principal Executive Assistant – an experienced incumbent – focuses primarily on providing business support to the Chairman.


Whilst there will be overlap and the requirement to work as a closely knit team, the Personal Assistant will focus primarily on general administrative support to the Chairman and his family. The Personal Assistant will also be required to stand in for the Executive Assistant as required and thus must have a requisite level of skill, confidence, experience and gravitas.


The key responsibilities of this role are divided between supporting the principal in his role leading his multinational operating company and supporting the Chairman and his family with their demanding travel needs and extensive international commitments. This focus will be primarily on the administrative and travel components.


  • This role’s primary focus is the principal’s business travel and social schedule, ensuring the schedules of other key executives (CEOs, etc) are deconflicted. The EA Team will maintain a 12-month rolling calendar with increasing detail by quarter.
  • Deconflict business and personal/family engagements, pre-empt adjustments and predict travel scheduling.
  • Meet all business and personal travel needs of the principal and the family, both domestic and international. Perform all liaison with all supporting staff, including air and yacht crew, and house managers, drivers and hotels to ensure all detailed requirements are addressed in full and in advance.
  • Research and liaise with hotels and service providers globally. Be prepared to negotiate pricing and ensure the very highest standards of support are provided.
  • Closely monitor on-going travel planning and in-progress trips and confirm that all arrangements are executed flawlessly or adjusted as necessary.
  • Be prepared at short notice to support additional requirements/changes to travel plans including changes driven by the pandemic and COVID testing requirements.
  • The Personal Assistant will be required to review and verify invoices for accuracy, demanding an exceptional eye for detail and awareness of cost/basic accounting principles.
  • The PA will handle as necessary the principal’s correspondence, calls, filing and document handling.
  • The PA should be prepared to travel domestically and internationally albeit it rarely and must be able to stand in for the Executive Assistant as required.


  • Degree-level education is expected but not essential.
  • A minimum of 5 years experience in a similar role as PA to a C-suite/UHNW individual/family office environment and demonstrable longevity of employment in prior roles.
  • Considerable demonstrable experience with complex travel arrangements for senior executives, ideally including with private jets, yachts and car service both domestic and international.
  • This unique role requires an individual with demonstrable experience delivering exceptional results for a sophisticated UHNW family office and/or C-suite executive.
  • The individual will be a consummate problem-solver, self-starter and critical thinker with a passion for continuous improvement. The successful candidate must be resilient, unflappable and accepting of feedback.
  • He/she will be required to identify challenges and to solve them, or present recommendations for a decision.
  • A calm demeanour combined with the ability to cope with ambiguity and manage short-notice change with minimal direction is expected.
  • The incumbent must be extremely efficient with their time; effective time-management is critical.
  • The requirement for absolute discretion is paramount, as is the willingness and ability to delegate tasks and monitor progress ensuring adherence to timelines in support of the principal’s objectives.
  • The EA Team (shared responsibility) will arrive in good time every day before the principal and will be required to remain until he leaves the office.
  • There is a requirement for occasional out of hours/weekend working. The requirement to closely monitor ongoing travel arrangements in order to be responsive to required changes is paramount. This will require that the Personal Assistant aligns with other time zones (principally the UK) as necessary.
  • The role requires excellent IT skills – MS Excel, Word, Outlook, PowerPoint


To apply, upload your resume and complete the required information in the “Apply For The Job” section located to the right of the posting. Alternatively, quote the position title and email your resume to: Sherry;

TDS Personnel is an equal opportunity employer and is committed to providing employment in accordance with the Ontario Human Rights Code and the Accessibility for Ontarians with Disabilities Act. Accommodations within reason due to a disability or medical need are available on request for candidates taking part in the recruitment process.

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