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PART-TIME: Flexible, organized, and proactive sitter for two creative and smart boys, 5 and 9, in Cobble Hill.

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Are you flexible and proactive? Do you have experience with early school aged boys in an after school capacity? A returning family in Cobble Hill is looking for someone energetic, proactive, intuitive, and positive to join their team as they enter into the new school year. Their boys, 5 and 9, are in private school and are very likely to return to school full-time, so they are looking for someone who can assist in the afternoons and be flexible to help out during the days on occasion. They are a very open and communicative family so should schedules be changing due to Covid, their sitter will be the first to know! This also means that their ideal sitter is flexible and adaptable as they navigate this new world together. It's $20-25/hour gross for 25 hours/week guaranteed! The position will begin in the fall with interviews taking place virtually in the weeks to come!

The Ideal Sitter for this Job

They are looking for someone positive, upbeat, energetic and willing to take initiative and plan activities for the kids. The ability to drive valid driver's license and clean driving record), cook and assist with meal preparation, do some light clean up (i.e., toys away, counters washed off, loading/unloading dishwasher) an open communicator who will partner with the parents to maintain a COVID safe relationship. Someone who can bring maturity to the position and exercise good judgement in the heat of the moment. Someone positive and upbeat is super important for their family. Someone who is flexible and willing to take on new tasks and try new things with the boys; they are really looking to get the boys into new activities and learning about the world around them. Someone super engaging and can come up with creative ways to explore the boy's new interests. Someone athletic who can keep up with them and keep them motivated. Someone who can encourage their outdoor activity more as well. Someone who can take initiative to plan things for them and can be thoughtful with their activities together. They love for their kids to be active and for ther sitter to take charge in the planning of both activities and meals. Suggesting new plans and foods is huge for them. Someone who is communicative with them about their own needs and is easy going.  If someone had early ed and had worked with kindergarten age extra plus. Both parents working from home. Comfort potentially traveling to the Berkshires for a week or so at a time if the kids are virtual is a plus, but not required. 


Starting in Fall, the schedule will likely be Monday to Friday, from 3-7 PM, with flexibility to come earlier or staying later if the need arises or if schedules change as a result of covid. Flexibility to assist with their school holidays and days off for full days as well. Flexibility is important in this role as things may be changing with Covid in the city. They are happy to guarantee 25 hours/week!

About the Children

boy, 9- He is smart and chatty! boy, 5- He loves trains and building.  They are smart kids who like to have a lot of conversations. They aren't particularly sporty or artsy, but they are active and are creative in their own ways. They like science projects. 


If the kids are in school, which is likely, it will primarily be for after school to assist in taking kids to any after-school activities or playdates (depending on COVID) via their car (license and clean driving record needed). If the days are virtual, the sitter will engage with the kids and supervise our little one in particular during the school day.  Helping with their meals and tidying up after dinner and play. Keeping the boys on track when it comes to their homework, etc. In a safer time, taking packages to the UPS store and keeping an eye on household supplies, doing a bit of shopping in the neighborhood as more household management.

Additional Information

They have been up in the Berkshires since March and may try to go up more in the fall for a week or so at a time. The current plan is to send the kids to school in person. The school will have precautions in place, but they are super open and communicative about what the plan will be and wouldn't expect anyone to come should the kids have to quarantine at any point due to covid exposure. Dad is back at the office once every 3 weeks with a skeleton staff. 

  • Rate

    $20-25/hour gross


    through the 2020-2021 school year

    Total Hours per Week

    25 hours/week guaranteed

    Apply Now

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