Property Manager Costa Rica Jobs in Toronto, ON (NOW HIRING)

A Toronto-based family with twin boys (age three) is hiring a head caretaker and team lead to be the senior practitioner for their children’s care. The role is hands-on with the boys daily and leads a small junior caretaking team in a fully staffed household. The boys have been raised with RIE and Pikler practices since they were six months old as a daily lived practice, applied rigorously, and the candidate must match that depth fluently. The household currently operates as a collaborative team, and the principals are hiring this role to lead it. The family are open to full-time, five days a week, or a structured rota (3:1, 2:2, or 1:1). Candidates would need to be comfortable working full-time for at least 6 months to build the relationship with the children and team, then the opportunity could shift to a ROTA schedule. The ideal candidate will either be Toronto-based or willing to relocate, with relocation expenses covered by the family. Travel between residences and periodic international travel is expected.

About the family

Two parents and twin boys, age three. The principals are hands-on parents; the right candidate is comfortable working closely alongside them. The boys have been raised with RIE and Pikler practices since they were six months old. This is a daily lived practice in the household, applied rigorously from the start. As a result, the boys are unusually verbal and self-aware for their age; the right candidate brings deep, fluent practice in these philosophies and can help them continue to evolve.

The household

The household currently operates as a collaborative team environment, and the principals are hiring this role to lead it. The team includes a small caretaking team, a chef team, a housekeeper, a chief of staff, and a property manager. A RIE coach can be engaged on an as-needed basis if helpful. Senior care decisions presently sit with the principals; the head caretaker will take them on in partnership going forward.

Travel

Toronto is the family’s primary residence. The longer-term aspiration is to spend colder months somewhere warmer — likely California (South Bay) or Costa Rica — with periodic international travel. Travel could amount to three to five months a year. The family is still developing its travel infrastructure for moving the team and the boys; experience helping other families establish stable team-and-children travel rhythms is valued.

The head caretaker & team lead is the senior practitioner for the children’s care — hands-on with the boys most of the day, leading the junior caretaking team, and holding consistency across the household on philosophy, sleep, food, transitions, and communication. The role partners with the principals on strategic care decisions and brings senior judgment to family planning that affects the boys. In short: deep RIE/Pikler fluency, prior leadership of a children’s care team, and genuine love for hands-on caregiving and team leadership in equal measure.

Responsibilities

• Direct hands-on care of the boys: feeding, dressing, sleep transitions, outings, emotional support, and daily activities.
• Leading, managing, and developing the junior caretakers: schedules, standards, onboarding, and modeling practice in the day-to-day.
• Holding consistency across the team on RIE/Pikler practice, sleep, food, transitions, and communication norms.
• Direct communication with the principals and senior household leadership on what’s working and what needs attention.
• Sole-charge coverage if the principals travel for periods up to a week.
• Senior input on family decisions affecting the boys: travel and relocation logistics, school choices, transitions.
• Traveling with the family between residences and on periodic international travel.
• Stepping in on adjacent areas when needed: light meal prep, child-related errands.

Admin

• Act as the "anchor" and the lead childcare professional in the home
• Ensure continuity of care across the caregiving team.
• Supervise and mentor other caregivers; facilitate clear communication and professional growth.
• Maintain organizational systems for daily, weekly, long-term and seasonal projects, and team schedules to ensure a predictable environment.
• Maintain clear, professional communication with the parents

• Has led a children’s care team — head nanny, daycare director, ECE program lead, or similar — and genuinely loves the leadership work.
• Equally loves hands-on caregiving; treats moments like wiping a child’s hands or face as an intentional, attuned moment of connection.
• Deep RIE and/or Pikler practice. Formal training (RIE Foundations or Associate, PiklerPedagogue, or equivalent) strongly preferred.
• Prior experience in fully staffed households; comfortable working closely with hands-on parents.
• Has worked as part of a high-trust caregiving team and finds that environment energizing.
• Holds clear, healthy professional boundaries. Communicates concerns directly upward to the principals and senior household leadership.
• Sole-charge ready: confident running the children’s care function for periods up to a week if the principals travel.
• Drives. Holds the structure of meals, sleep, medical, transportation, allergens, and routines.
• Brings senior input on family decisions affecting the boys — travel logistics, school choices, transitions, philosophy evolution as they grow.
• Comes to work calm and grounded with the ability to read energy and adjust accordingly. This matters above all.
• Comfortable in a detail-oriented, systems-driven household. The home runs on structure, so daily life feels calm and flows smoothly; comfort working within that is expected.
• Comfortable signing an NDA and practicing discretion as a matter of course.
• Bonus: prior parenting experience, Spanish or French, ECE degree.

Ideal skillsets and history:

• You have experience with sole-charge caregiving rooted in presence and respect.
• You have a deep understanding of child development, best practices and caregiving philosophies and are seasoned enough to advise the parents as needed.
• In addition to exceptional caregiving you have a proven history of team leadership, organization, and household management skills.You are highly organized, proactive, and capable of managing the complex moving parts of a high-net-worth household.
• Deep knowledge of child development, standards of care, RIE approach, next approach.
• Seasoned enough to advise as parents where to go and next stages, on a caretaking lens.
• Family looking for: family thought partner. Working with them in the best interests of their children

• Valid U.S. Passport, Green Card, or Employment Authorization Card (EAC) - candidates do not need to have Canadian citizenship in order to apply to this role.
• This is a gluten-free household; one child has digestive sensitivities with an active reintroduction protocol for certain allergens (dairy, egg).
• Unscented home. Non-smokers and non-vapers only.
• Candidates should be up to date on their annual Flu shot.

• Candidates should be comfortable with a live-out set up, with separate accommodation provided when needed (e.g. during travel).

• Driver’s license required.
• NDA required.

• Very competitive salary, commensurate with experience and fit.

• A healthcare stipend is offered, along with all other industry standard benefits.