Sitter​/Driver

Sittercity seeks a reliable Sitter/Driver to support a family with two busy middle and high school teens. In this role, you'll manage after-school and occasional weekend pick-ups, drop-offs, and activity runs across Chicago, ensuring safe, on-time transportation. You'll coordinate schedules, communicate clearly with parents, and help teens navigate busy days with calm, friendly support. Join a mission-driven, tech-enabled marketplace focused on safe, flexible care and make a direct impact on a family's daily life.

Responsibilities

• Provide after-school and occasional weekend transportation for two teens to school, practices, and activities
• Ensure timely, safe pick-ups and drop-offs using a reliable, insured vehicle
• Monitor schedules, adjust plans, and communicate changes with parents promptly
• Support teens' independence while maintaining appropriate supervision and boundaries
• Use Sittercity's platform and tools for scheduling, messaging, and updates
• Maintain a calm, professional demeanor in traffic, changing plans, and teen-related conflicts
• Respect family privacy, household rules, and safety guidelines at all times
• Perform light related tasks such as confirming appointments and planning routes

Required Skills

• Safe driving and navigation
• Time management
• Schedule coordination
• Use of mobile apps/GPSBasic childcare/teen supervision
• Clear written and verbal communication
• Risk and safety awareness
• Problem-solving and adaptability
• Customer service mindset
• Boundary setting with teens