Sitter Policies and Expectations

updated 2/1/24

We value transparency and are obsessed with clear communication in every form.

For current Active Super Sitters, and any potential Super Sitters.

We are still flexible, understanding, and start with empathy and curiosity in our Super Process. These policies are here to keep us all clear on expectations and operating from the same playbook.

On this page you will find policies and info related to:

  • Placement & Booking
  • Transportation 
  • Availability Calendar & Email 
  • All Sitter Payment
  • Feedback 
  • Cancellations & Sickness
  • Sitter Cancellation & Lateness Policy – Points System
  • Agency Contact Info & Team Members 

These apply to all Active Sitters on the Chicago Super Sitters Roster. You can read and review all Family Policies here. We have high expectations for them too.


Placements Info - booking, transportation, sickness

How do I get booked for a placement?
What happens when I do get one?
What happens afterward?
What is the transportation expectation?
What happens if someone gets sick?


**Sickness Policy** updated 2/2024

UPDATED Feb 2024

Baseline Sickness:  Sniffles, runny nose, and some sort of dry cough (no fever) – AKA the “Chicago Winter Cold”. The cold that is prevalent in parents, kids, & those around children, especially during the winter months.

This ‘Baseline Sickness’ means that the agency, families, and sitters understand that while working with kids, or having kids in your home, this “Baseline Sickness” is to be expected and is not a barrier to work, or to placement confirmation, unless shared with the agency separately on this form (sitter) or this form (family).


  • If a sitter declines to work in a home with “baseline sickness” present, they are NOT due a cancellation fee, but they also do NOT lose a point with CSSitters. CSS will attempt to find a substitute sitter for the family.
  • If a sitter has “baseline sickness”, and the family declines the coverage, the family is responsible for the cancellation fee due to the confirmed sitter.
  • If a family has anything more than “baseline sickness,” a sitter may decline to work and the family is responsible for the cancellation fee due to the confirmed sitter.
  • If a sitter or family has anything more than “baseline sickness”, standard cancellation protocol applies. 


Covid Exposure:  It is the agency’s opinion that at this point, anyone exisiting without a mask in any public space these days has been exposed to Covid, even if they have not been told specifically about an exposure. If a sitter/family/child is exposed to a known positive Covid case, it is expected that person will test for Covid and relay this information to the agency and/or the sitter/family.

If the family, child, and/or sitter exposed is testing NEGATIVE, is otherwise not displaying any symptoms, and is willing to wear a mask, the placement is expected to proceed as booked.


  • If a sitter declines to work in a home that has been exposed to Covid but where all parties are testing negative, are showing no symptoms, and willing to mask, they are NOT due a cancellation fee, they will NOT lose a poing with CSSitters. CSS will attempt to find a substitute sitter for the family.
  • If a sitter has been exposed to Covid but has tested negative, is showing no symptoms, and is willing to wear a mask, and the family declines the coverage, the family is responsible for the cancellation fee due to the confirmed sitter.
  • If a sitter or family has tested positive for Covid, standard cancellation protocol applies.

Both families AND sitters are able to inform CSSitters if they feel they are an exception, and the “baseline sickness” and “covid exposure” policies should NOT apply to them or their household. Please use this form (sitter) or this form (family) to share this information with the agency. 


If ANY sickness is not disclosed:

  • If a Super Sitter arrives at a placement and finds more than “baseline sickness” that has not been disclosed, they are permitted to leave immediately, and full placement compensation is due.
  • If a Super Sitter arrives at a home with more than “baseline sickness” that has not been disclosed, the family is permitted to send the Super Sitter home with no payment and a refund for placement from CSSitters if a replacement can not be found.

As always, we expect that there will be thorough communication between sitters and families around any and all sickness. We continue to encourage everyone to wash hands and wear masks to ensure the utmost safety of everyone involved in any CSSitters placement.

How do I book/Accept a placement?

CSSitters Requests Line will reach out VIA TEXT for placements we think are a good fit specifically for you.

‘Good Fit’ includes:

  • Being listed as available on your CSS calendar
  • Experience with the specific number and age(s) of the kid(s)
  • Proximity to family home, and safe transportation to/from
  • Pet allergies/comfort
  • Family needs/sitter strengths
  • And any other detail we can include
  • We prioritize sitters that have been requested by name on a family’s request.

CSSitters Requests Line will reach out VIA EMAIL  for placements that are being asked of a group of sitters, or the whole roster.

  • Recurring Placements
  • Last minute placements
  • Hard-to-fill placements
  • Special requests

What happens when I accept a placement?

Once you have confirmed you are interested and available for a gig, CSSitters will send:

  1. A confirmation email that includes:
      • Placement Date
      • Placement start and end time
      • Family details (including address, contact information, and child(ren’s) age(s)/allergies/notes, and general famiy notes)
      • Feedback from past sitters (if applicable)
      • Any relevant notes from CSSitters that will inform your experience.
  2. A Google Calendar invite
    • The invite should be ‘accepted’ in the email invite OR in the calendar event itself.
      • The invite includes: Parent contact info and the placement address
      • For Recurring Placements: This calendar invite is sent to parents too

What Happens at the end of a placement?

You are paid directly by the family before you leave.

You complete the Sitter Feedback Form as soon as the placement is over.

Transportation To/From Placements

Sitters should assume responsibility for transportation to and from a gig unless clearly stated otherwise.

    • For one-time placements we require the families to note if they’d be willing to send a sitter home in a car / provide a ride home afterward so if a ride home after is important to you and we don’t mention it in the original pitch, just ask us.

Availability Calendar & CSSitters Email

Each Super Sitter recieves a private account when they join the active roster.
You will be issued an email address.
Your calendar is a Google Calendar associated with your email address.

Availability Calendar

  • Your availability should be listed as FIRSTNAME LASTNAME and show the times you are available and looking to work
  • Make sure your start and end times are accurate and reasonable
  • Give yourself time to commute to/from a gig if your availability starts before/after another engagement
  • Do not use your CSS calendar for personal events and activities – this makes it very difficult to read everyone else’s availability and also we see them on the admin calendar

Your calendar should be up-to-date and accurate so the scheduling team can tell at a glance who is available, when.

  • CSS will take down/adjust your availability when you accept a gig
  • You are responsible for taking down/adjusting your calendar when your availability changes outside of CSS.

Super Sitters email account

You will be issued an @ChicagoSuperSitters email when you join the Active Sitter roster.

  • This is a Google account
  • All  correspondence with CSSitters goes through this email
  • This email is closed if/when a sitter leaves the Active Sitter roster

All Sitter Payment Info

All General Payment Policies
All Sitter Hourly Rates – One-Time and Recurring Placements
Monthly Payment to the Agency – how and when

SItter Payment Policies

Hourly payment always goes directly to the Super Sitter at the end of any in-home placement. 

  • Payment is due when the placement is over, before you leave a placement. Parents know this, but sitters should be prepared with their payment handles, and/or the anticipated total so they can confidently ask for payment at the end of a placement.
  • Hourly rates are always listed in every confirmation email, and will vary family to family. 
  • Hourly rates are not negotiable by sitters or parents (though parents are permitted to pay more if they’d like).
  • If a family relieves you before the scheduled end time, they are responsible for paying for the time worked, not the time booked, as long as it still meets the minimum of 3 paid hours. *You can submit this on feedback as we know it can be a deterrant to future gigs.
  • All payments go directly to individual Super Sitters. Chicago Super Sitters Ltd. does not record, report, or track income, or provide any tax documentation. This is the responsibility of each individual Super Sitter.

Sitter Hourly rates

Suggested hourly rates are determined by CSSitters and sent in every confirmation email.

  • Your hourly rate will vary family to family, based on the criteria listed below.
  • Rates are for every hour and are paid directly to the Super Sitter at the end of the placement. 

One Time Placements:

    • 1 Child – $20/hour
    • 2 Children – $21/hour
    • 3 Children – $22/hour 
    • 4 Children – $TBD – based on age-spread, needs of placement.
    • 5+ Children – $TBD – based on age-spread, needs of placement.

Recurring Placements:

    • 1 Child – $22/hour
    • 2 Children – $23/hour
    • 3 Children – $24/hour
    • 4 Children – $TBD based on age-spread, needs of placement.
    • 5+ Children –  $TBD based on age-spread, needs of placement.

Additions to hourly rate:

    • Infant (under 6mos): +$1/hour
    • Two children under 2y: +$1/hour
    • Sitter in Hotel Room/Home Rental: +$1/hr
    • Sitter working somewhere other than the family home: +$1/hr
    • Combined Families (two or more): +$2/hr for each extra child from family #2, 3, etc.

Possible TBD Extras:

    • Gas/Travel stipend: $TBD, based on location (will be known prior to booking)
    • Special Skills Required (Language, special training):  $TBD – depending on request.
    • Overnight Care: Rates vary based on sleeping habits, ages, etc. Inquire for more info.

Monthly Fee paid to the Agency

All Active Sitters are required to pay a $20 monthly fee to CSSitters.

  • This is due on the 1st of each month you are on the Active Sitter Roster. 
  • This fee will be first charged 3-6 weeks after becoming an active sitter (depending on the calendar month) to give you a chance to work with us before paying a fee.
  • When offboarding from the roster, we need 7+days notice in order to stop billing for the following month. 

Feedback Info

Feedback is part of what makes Super Sitters successful. Sitters and families are expected to complete a feedback form after each new sitter/family match. 

Feedback Form Link

  • Feedback form Link:
  • The same link can be used over and over again (save it!)
  • The feedback form should be completed as close to the end of the gig as possible (so it’s still fresh in your mind)
  • Feedback is especially important if it’s a family you haven’t met before or haven’t seen in a while!

    What happens with submitted feedback?

    Please fill out this form honestly!

    • Families NEVER see sitter feedback
    • Feedback is read by admin staff to ensure sitters are being placed with families they felt comfortable with and excited to go back to
    • If it was a great experience and you’d love to see this family again and again, we need to know so we come to you with their future requests!
    • If it didn’t feel like a great fit, and you get a pit in your stomach at the thought of being asked to sit for the family again, we need to know – you don’t have to go back
    • Feedback is given to future sitters so they have the information and context they need to feel up-to-date and informed before they walk in the door

    Family Feedback about Sitters

    Families are asked to complete a feedback form about their sitters.

    • If a family sings your Mary Poppins praises, we will let you know.
    • If a family brings a negative something to our attention that we feel needs to be addressed, we’ll come to you directly to ask for your side of things.


    We take cancellations seriously, from families and from sitters. 

    Cancellation - When a SITTER has to cancel (RECP or OTP)

    • The sitter must first complete the Sitter Cancellation Form
    • The sitter should text the family and let them know that they are no longer available, and that the agency is working on a replacement sitter
    • The sitter will lose one point. Please see the specific Sitter Cancellation & Lateness policy for more information on the points system

      Cancellation - When a FAMILY has to cancel (RECP or OTP)

      • If a family cancels through the agency, CSSitters will notify the sitter, and the reminder is sent that a fee is due directly to the confirmed sitter
      • If the family cancels directly to a sitter, the sitter should tell the family to contact the agency right away, and the sitter should contact the agency as well. CSSitters will send the reminder that a fee is due directly to the confirmed sitter.

      Cancellation fees vary based on the notice given:

      • $50 –  if a placement is cancelled after it has been confirmed
      • $Full Hourly for cancelled placement – if placement is cancelled with less than 48 hours before placement start time.

      Points System - what it means, and how it works

      Every Super Sitter starts with 3 points. 

      A Sitter loses a point by:

      • Canceling a confirmed placement (Rec or OTP)
      • Being late (we hear from the family or from you)
      • This counts for sickness, family/personal emergencies, or last minute tickets to Riot Fest

      A sitter regains a lost point after 60 days

      If a sitter gets to 0 points they will be ineligible for gigs until they talk to a CSSitters Admin Staff Member. This means a sitter has canceled or been late 3 times within 60 days

      If a sitter does not schedule a meeting with an admin within 30 days of being notified, they will be removed from the roster, ineligible for rehire.

      What we're hoping this does

      • Encourages sitters to double-check and be clear about their personal calendars before committing to a gig.
      • Emphasizes the commitment to CSSitters when accepting a gig.
      • Helps us keep track of how you are feeling and doing in general, and watching for any trends or need for help (burnout, etc).
      • Provides some accountability for cancellations to avoid overusing the agency’s flexibility.

      What we're hoping this doesn't do

      • Makes sitters nervous to accept gigs. Things happen, this is why the points can replenish. We need to be sure it’s not happening frequently.
      • Encourages sitters to hide/downplay sickness. Yes, sickness cancellation is still a point. Cancelling multiple gigs in a row due to the same sickness is still one point. See Sickness Policy.

      What the admin meeting is for

      To communicate clearly with voices, and not emails.

      And to allow the sitter to give CSS insight into why they have canceled and/or been late 3 times within 60 days.

      • Maybe you’re burned out, overwhelmed, and exhausted by childcare or life outside of CSS
      • Maybe you’ve been struggling with mental and/or physical health issues
      • Maybe there are other things going on in your life that keep you from prioritizing CSS right now
      • Maybe it’s something else entirely that we can’t even imagine
      • ^that’s okay! But we can’t support you if we don’t know

      What the admin meeting is not for

      • Immediate removal from the roster
      • Punishment for the sitter
      • Scolding of any kind

      Agency Contact Info

      CSS Requests Line – 773-609-1277

      • Receiving / accepting one-time gigs
      • Questions / information that needs to be seen by an admin and answered ASAP and/or outside of business hours
      • Cancellations, sickness, changes in a confirmed gig, etc.

      Requests Team:

      • Receiving / accepting all-calls, recurring gigs, general CSS info 
      • Questions / information that can be seen and answered during business hours

      Sitter Hiring/Roster Management Team: 

      • Information updates (address, name, pronouns, etc.)
      • Invoicing Questions
      • Offboarding/leaving the roster

      Team Members

      Tori U.  She/her
      Founder, Owner, CEO

      Jenni N. She/Her

      Breanna B. She/Her