We Take "Super" Seriously


We will welcome new Super Sitters again in Spring 2021!

We will be looking for candidates with part, full, recurring, day and evening availability, and everything in between. 

We would love to stay in touch! Please click here or the big pink button to make sure we can get in touch with you when hiring starts up again! 

Want us to let you know when hiring starts again?

We are re-opening to new Families and Sitters in Spring 2021!

We have been fixing, updating, and refining our intake process and we can’t wait to meet you soon.

Read below to learn more about our process so you’re ready when we get started again!

We want the best for you and the best from you.

Why should you become a Chicago Super Sitter? We know what makes a babysitter great and what makes a great babysitter happy. Not only do we know how everything works, we know how hard the job can be. We expect a lot from our sitters, and that’s why we’ve got your back. We give advice when you need it, we help nurture your strengths, and we make sure you feel like a valued part of our team. We screen each family before you meet them and then provide you with a detailed profile. There are no surprises when you walk in the door.

We match our sitters to families based on personality, parenting style, location, and schedule needs, even during a pandemic – we will not compromise our level of service.

1. Submit your Application

We review it and if we like what we see, we contact you directly. We are looking for details, professionalism, and a genuine interest in working with children. 

2. Phone Interview

We schedule a call and if we like what we hear, we keep you moving forward. 

3. Reference Check

We ask for a minimum of three recent (non-family) childcare references and one professional reference. And we definitely check their validity. All check out? You keep going.

Super Tip: Start collecting your references right away (we’ll provide you a link) and ask for more than you need. Many applicants drop off at this stage because their references aren’t being cooperative.

4. In-person Interview *During CV19, this is being done by video

We want as many perspectives as possible and really want to know who you are. You will meet with a CSSitters staff member via video chat for an in-depth screening to help assess qualifications and professionalism. If this goes well, we’ll keep things moving.

5. Meeting with Tori

Tori is very serious about who is selected to represent her company and still talks with all candidates before they join the roster. If she thinks you have what it takes, you’ll move to the final stages.

6. on-boarding and paperwork

There are calendar and scheduling instructions, Sitter Policies and Expectations to revise, and final details to review (by you, and by us).

Super Tip: Don’t flake out during this part. These are important details that we must have and it is still part of the screening and our search for professionalism. Remember, you aren’t in just yet.

7. Background Check & *CPR Validated

Background Checks are non-negotiable and must be completed before you start working. 

*CSSitters believes strongly in hands-on, in-person training. Because that is not possible at this time, we are temporarily suspending mandatory CPR Certifications for sitters. If you do not have a current certification, it will be noted on your profile, and the family that you work with will have to okay it before confirmation of a gig. Once our in-person classes can resume safely, every Active Super Sitter will be required to be certified.

8. Officially Become A chicago super sitter

Once everything checks out and if after the long hiring process we feel we are a good fit for each other, we invite you to join the team and get you working! Whether here with us during CV-19 or for the long-haul, we are excited to have you!


Please understand that although being a babysitter includes lots of giggling, and peek-a-boo, we take our screening process VERY seriously even as we work in these crazy and different times. As we have said, our reputation relies on our caliber of sitters, and we will only work with the best.

Want to be a Super Sitter?

  • Do you have at least three years of professional childcare experience?

  • Can you provide exemplary childcare and professional references?

  • Do you work hard?

  • Do you want to be part of an incredible Chicago family?

Why should you work with SuperSitters?

  • We screen all of our families too, so you’ll know who you’re meeting before you meet them.

  • We provide family feedback from other sitters so you are totally prepared before a gig.

  • We’re really fun and badass.

Sitter Hiring FAQs

These FAQ are about sitting gigs and the work in general. All CV-19 specific questions can be found on the CV-19 FAQ page.

Parents working from home - how does this work?

We know this changes the dynamic. Most families have one or both parents working from home. The biggest thing that makes a day like this successful is making sure that you are really clear as to what your responsibilities are and how you can be helpful. Ask specific questions of the parents to make sure you know how they would like to handle things.

How often will I be placed?
Ideally, as often as you would like. During CV19, we are placing sitters in Part-Time and Full-Time Recurring Schedules to help minimize exposure and ensure that we are safely and ethically placing sitters and families. We are NOT placing one-time requests at this time.
What’s the pay and how does it work?

You will be paid directly from your client family at the end of each placement. Your hourly rate will vary from family to family. You can see the rates HERE. You and the family will know this rate before you accept a placement.

How does scheduling work?

We are NOT placing one-time requests at this time (as we would in ‘regular’ times). To accommodate the new need for families working from home and/or essential workers we are exclusively placing Part and Full time recurring placements only. These placements are the same days and times each week, with the same family. We are extending two weeks at a time, and operating with an open-ended timeline (until we learn more about the school year, openings, etc). We will adjust each placement as needed when schools/businesses reopen.

You can learn more about these packages HERE.

How much will I know about the job before I arrive?
When a family signs up with CSSitters for the first time, they are asked to fill out a form that outlines who makes up the family and how you will be expected to handle the children while they are in your care. We also talk to them during an intake call, ask a bunch of questions, and vet them before their first placement. We will make sure you have all of the information you need to feel fully prepared.
What will be expected of me when I get there?
FIRST – Wash your hands.
There is a suggested 15-minute minimum parent/sitter overlap so all questions can be answered and to ensure the kids feel as comfortable as possible. We expect you to use this time to ask questions of the parents, engage the children, and do your best to make sure the parent(s) are feeling ready to leave you in charge.
Why don't I just give the family my number and let them contact me directly?
Our system is based on trust. We expect all sitter requests to go through CSSitters’ booking system and ask our sitters to send the families to us if contacted directly.  If we find out that a sitter is booking CSSitters families without our knowledge they will be removed from the active roster.
Nanny Cams?
With the new fancy technology in our world, nanny cams now come in all different forms. Security system cameras, baby monitors, programs on phones, and the tried and true, hidden ‘teddy bear eye’ camera. These cameras can be a great tool for parents so that they can monitor what is going on with their kiddos when they aren’t home. Chicago Super Sitters asks that families tell sitters if and when recording devices are in use. We firmly believe that these tools are best used as a method of prevention. ‘An ounce of prevention is worth a pound of cure’.
Who are these families and what are the kids like?
We understand how nerve-wracking it can be to walk into a new home, be faced with new rules and expectations, and have no idea what they actually want from you. Never have that worry again! Before you are placed in a new home, we will send you as much information as we can about the family including discipline style, bedtimes, age-appropriate tantrums or freakouts occurring as of late, demeanor of the parents, and so on. We want you to go to the placement feeling confidently prepared and able to do your best job.
Do family cancellation fees still apply?

As you know, all of the changes/cancellations happening are affecting everyone in different ways. It’s especially hitting the gig economy hard, and we are asking families to consider their sitter’s income and to pay cancellation fees at their discretion and only if it is in their budget to do so.