We create exceptional teams  with a specialized focus on staffing UHNW domestic and corporate support-level roles.

Read more
Subscribe

Your Next Exceptional Placement Awaits.

We don’t just list jobs; we curate career-defining matches for the industry’s most dedicated support professionals.

At Sterling Estate Staffing, we specialize in connecting high-level talent with ultra-high-net-worth families, industry founders, and A-list celebrities across Canada. Our goal is to analyze your unique experience and career trajectory to ensure a placement that is both productive and fulfilling for the long term.

see job list

Featured Opportunities

Where Professional Excellence Meets Personal Compatibility.

Explore our curated list of active openings within Canada’s most prestigious households and corporate offices. At Sterling Estate Staffing, we don’t just fill vacancies; we facilitate career-defining matches for top-tier talent. Every role we represent is an opportunity to join a high-functioning team that values discretion, performance, and long-term fulfillment.

Personal Assistant - UHNW Family Office

Job: SES110

Full-time

PA – UHNW Family Office 5 days office possible 1-day WFH.

We are working with a highly impressive UHNW Principal and his private family office to find an outstanding PA who is looking for a long-term, career-defining role within a fast-paced, multi-faceted environment spanning entertainment, property, investments, and private interests.

This is a rare opportunity to join initially in a supporting role to the Operations Manager/PA, gaining full exposure to the principal’s personal and business affairs, with a clear and structured progression into a 1:1 PA role once fully embedded and up to speed.

This role will suit a highly polished, emotionally intelligent PA who thrives on responsibility, discretion, and being at the very heart of a private office operation.

THE ROLE

You will act as a true right-hand support across both professional and personal matters, ensuring the seamless day-to-day running of the principal’s life and wider interests.

  • Providing direct, support to the principal in all personal and business matters
  • Acting as gatekeeper and first point of contact for business associates, friends, and family
  • Complex and ever-changing diary management across business, investments, and private life
  • Full inbox management, prioritisation, and drafting on behalf of the principal
  • Research and preparation of presentations, reports, and key documentation
  • Organising highly complex international travel for the Principal and wider family, including fast-changing itineraries, visas, entry requirements, and security coordination
  • Supporting property management and operational projects across the portfolio
  • Treasury and financial administration support, working closely with advisors and finance teams
  • Management, hiring, and training of Junior Team Assistants
  • Lifestyle research and coordination including healthcare, private travel, restaurants, gifting, events, and holidays
  • Full responsibility for all personal medical administration for the principal and his wife
  • Running high-level personal and business errands with efficiency and discretion

THE CANDIDATE

This role will suit a career PA/EA with experience supporting at senior or UHNW level, who is commercially aware, exceptionally organised, and thrives in an environment where no two days are the same.

You will be:

  • Polished, discreet, and emotionally intelligent
  • Naturally proactive, with the ability to anticipate needs before they arise
  • Confident managing complex, high-pressure workloads
  • Comfortable liaising with senior stakeholders, advisors, and international contacts
  • Highly detail-oriented, with impeccable written and verbal communication
  • Looking for a long-term role with genuine progression into a trusted 1:1 partnership
Apply now

Head Housekeeper - UHNW Family Toronto

Job: SES111

Full-time

Live-out Head Housekeeper to manage a team of 2 housekeepers and 1 full-time launderer at the formal residence of an UHNW family of five (two adults, two teenagers, and one toddler). The property is a very large, beautifully maintained, fully staffed and formal six-bedroom home in Toronto. The household is structured and well-managed, ensuring clear guidance for the new team member while encouraging proactivity, initiative and teamwork.

This is a fantastic opportunity for an experienced Head Housekeeper with a background in luxury settings to work in a supportive and professional environment.

It is important to note that while this is a Head Housekeeper position and team management is part of the job, the successful candidate must perform all regular housekeeping duties as the rest of the team, leading by example.

HOUSEKEEPING:
  • Maintain the home to the highest standards of cleanliness and organization.
  • Handle daily cleaning tasks, ensuring every room, surface, and detail is impeccable.
  • Care for high-end furniture, fabrics, and finishes, following best practices (training provided).
LAUNDRY AND IRONING:
  • Support the full-time laundress when needed, especially during her absence, handling delicate fabrics and ensuring impeccable results.
COOKING:
  • Prepare breakfast for the family, adhering to their preferences.
TEAMWORK AND TEAM MANAGEMENT:
  • Efficiently and gracefully manage a team of 3 (2 housekeepers and 1 launderers). Creating and manage schedules on a rotating basis, managing the team and tasks and ensuring the home and the team dynamic runs smoothly.
  • Be prepared to lead the team by example, taking care of all housekeeping duties as the rest of team members.
  • Collaborate harmoniously with the rest of household staff.
  • Remain professional when interacting with the family and other members of staff. It is important to remember this is a formal household where performance to the highest standard is expected of all household team members, regardless of whether the family is at home or not.
  • Work independently when needed, particularly if assigned to prepare the family’s other residences.
TRAVEL:
  • Occasionally travel to other US/European destinations to prepare homes or provide support when the family is in residence in periods of 2 to 4 weeks at a time.

CANDIDATE PROFILE:

EXPERIENCE: 
Minimum 5 years in luxury hotels, and/or UHNW private households is required.
SKILLS:
  • Strong communication and teamwork abilities. Able to follow the household protocols that are already in place.
  • Excellent housekeeping and organizational skills.
  • Proactive and able to work independently, especially when managing tasks off-site.
  • Flexible mindset to adapt to high- and low-intensity periods while always working to a high standard and maintaining professional demeanor with other team members.
LANGUAGES: 
Fluent in French with conversational/professional English or vice-versa.
PERSONAL ATTRIBUTES:
  • Honest, reliable, and discreet.
  • Professional appearance and demeanor.
  • Able to maintain harmony within the team while staying focused on duties.
REQUIREMENTS:
  • Valid driving license and own car. A vehicle is provided for work related duties.
  • Canadian passport.
  • This position is ideal for someone with low personal commitments, they must ensure that personal responsibilities are always managed to ensure full availability.

 

ADDITIONAL PERKS:

TRAVEL BENEFITS: 
When traveling with the family, all expenses for transportation, accommodation, and meals are fully covered.
ONBOARDING: 
Comprehensive training provided to ensure familiarity with household standards and routines.
SECURE, LONG-TERM POSITION: 
This role provides long-term commitment for the right candidate.
SALARY:

$105,000 – $125,000 based on experience.

Apply now