Flexible Governess Jobs (NOW HIRING)

A warm, thoughtful, and private family based in Chicago is seeking a calm, proactive, and highly engaging Governess/Educator to join their household beginning in late August or early September 2026. The family has two young daughters, ages 5 and 2, and is looking for someone who can provide developmentally focused educational support, enrichment, and hands-on engagement for both children as needed.

The ideal candidate will bring a strong educational background along with a nurturing and grounded presence. The family gravitates toward candidates who are warm and intuitive, with a calm demeanor and the ability to be proactive without being overly forceful or intrusive. They are hoping to find someone who naturally creates enriching learning opportunities through play, conversation, exploration, and everyday routines.

Schedule:
Approximately 25 hours per week. The family is flexible regarding scheduling but would ideally like coverage spread across 3–5 days per week. They are open to structuring the schedule over several shorter days or a few longer days each week for the right candidate.

Travel & Summer Flexibility:
The family spends the majority of the year in Chicago and summers in Los Angeles. While this position is primarily intended to support the family's Chicago home long-term, the family is open to discussing a few different arrangements for the summer months with the right candidate.

Potential options may include:

• Traveling with the family to Los Angeles during the summer, with accommodations and travel expenses provided.
• If services are not needed during the summer months, the family would consider offering a retainer arrangement to retain the right candidate with the intention of resuming the position upon their return to Chicago.

• Creating age-appropriate educational activities and learning-based experiences
• Supporting developmental milestones, emotional growth, and intellectual curiosity
• Providing engaging, hands-on care primarily for the family’s 2-year-old daughter during the day
• Assisting with school-aged support and enrichment for the family’s older daughter as needed
• Encouraging outdoor activities, walks, creative play, and experiential learning
• Preparing simple meals/snacks for the children and assisting with light child-related tidying
• Maintaining a calm, organized, and positive environment for the children
• Collaborating closely with the parents and providing thoughtful communication and feedback

• Experience designing curriculum or enrichment activities for young children
• Experience working in private households
• Familiarity with gentle, play-based, or developmentally focused educational approaches
• Flexible schedule and openness to occasional future travel
• Long-term mindset and interest in growing with a family

• Bachelor’s degree required; degree in Education, Child Development, Psychology, or related field strongly preferred
• Significant experience working with toddlers and young school-aged children
• Background in private education, teaching, or governess roles strongly preferred
• Calm, emotionally intelligent, and highly engaging personality
• Able to take initiative while remaining respectful of parental preferences
• Comfortable working collaboratively with a hands-on mother
• Strong understanding of developmental milestones and age-appropriate learning
• Valid driver’s license and passport preferred

• Flexible Schedule
• $65/hourly