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IT Support Engineer

| Chicago

About Sittercity

Sittercity’s mission is to make child care finally work. We pioneered tech enabled child care in 2001, and we connect millions of parents with babysitters and nannies every year. Recently recognized as a 2018 Chicago Innovation Award winner and one of the best places to work by Crain’s and Built in Chicago, we are building a platform that is radically simplifying the way we find, book and pay for trusted care. Headquartered in Chicago, we serve families and caregivers nationwide.

What you’ll do

We are looking for an IT Support Engineer who is a self-starter that enjoys a variety of IT operations challenges from day to day. You will balance responding to specific support requests alongside managing larger projects that improve our IT operations. You will seek to implement efficient solutions that favor automation over supervision. The IT Support Engineer will report to the Head of Technology and work in collaboration with our entire team to support their IT needs.


  • Provide IT equipment and support to staff, including provisioning and maintaining Apple and Windows workstations and office equipment including Printers and Scanners.
  • Manage and support our Identity and Access Management systems, including user on- and offboarding activities.
  • Procure and manage software licenses for the organization.
  • Manage and support our Google Suite productivity tooling.
  • Provide regular recommendations to the Head of Technology on IT infrastructure investment and optimization opportunities.
  • Maintain and support our connectivity to the Internet from our main and satellite offices.
  • Hardware support, laptop procurement and management, IP voice management
  • Maintain internal documentation of our internal IT support processes and network architecture.
  • Manage and maintain our video and voice telephony and conference applications.
  • Assist in annual Technology budget planning and operate within agreed budget parameters.
  • Own and maintain the Sittercity Business Continuity Plan.

About You

  • Experience with Cisco Meraki network equipment, including Routers, Firewalls and Switches.
  • Managing persistent secure VPN connections between physical locations and cloud infrastructure.
  • Maintaining and supporting Polycom or similar IP Phone systems.
  • Experience supporting Google Hangouts / Meet or similar conference room audio/video equipment.
  • Experience managing G Suite for small to medium sized businesses.
  • Experience deploying at scale Mac and Windows workstations for customized for different roles in an organization.
  • Running IT services in cloud environments using modern containerized environments such as Docker, Kubernetes, or Istio.

Benefits and Perks

  • Support for flexible and remote working environments
  • Food and healthy snacks throughout the day
  • Ping pong, foosball and on-site fitness center
  • Company events, social outings and volunteer opportunities
  • Open personal time off policy
  • Industry leading maternal and paternal leave
  • Subsidized use of Chime for personal childcare services
  • Great benefits package, including; health, dental, vision, disability, life, 401(k)

Sittercity is committed to hiring a diverse workforce. We consider all applicants for employment without regard to race, color, sex, sexual orientation, gender identity, religion, age, national origin, disability, veteran status, or any other basis as prohibited by federal, state or local law.


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Technology we use

  • Engineering
  • Product
  • Sales & Marketing
    • GolangLanguages
    • JavascriptLanguages
    • KotlinLanguages
    • RubyLanguages
    • SwiftLanguages
    • GraphQLLanguages
    • Ruby on RailsFrameworks
    • RxSwiftFrameworks
    • MySQLDatabases
    • PostgreSQLDatabases
    • ClubhouseManagement
    • BrazeCRM


In the heart of River North, our office boasts views of the Wrigley building and Marina Towers. Grab a drink or lunch at the great restaurants nearby!

An Insider's view of Sittercity

What are some social events your company does?

During the work day, break time can equal Mario Kart, coffee runs or ping pong. After work, we have had fun activities including Trivia Night and happy hour. For food lovers, we've had potlucks, a chili cook off, and cookie contest!


Operations Manager

What's the biggest problem your team is solving?

Analytics is core to what we're building here. By leveraging data from social networks, family demographics, and existing users, we're creating a smarter matching experience for families and sitters. My team is making these data sources accessible to every team member, so we can make smarter business decisions and improve the user experience.


Director of Analytics

How does the company support your career growth?

Sittercity has allowed me to take on different projects and claim ownership in order to grow. They've supported my career decisions, like moving from operations to customer success. Every project I do matters and contributes to our overall success. Not only has Sittercity helped my career growth, they've helped me grow outside of work as well.


Customer Success Advocate

What are Sittercity Perks + Benefits

Health Insurance & Wellness Benefits
Flexible Spending Account (FSA)
Disability Insurance
Dental Benefits
Vision Benefits
Health Insurance Benefits
Life Insurance
Pet Insurance
Wellness Programs
Onsite Gym
Retirement & Stock Options Benefits
Child Care & Parental Leave Benefits
Child Care Benefits
Generous Parental Leave
Flexible Work Schedule
Remote Work Program
Family Medical Leave
Vacation & Time Off Benefits
Unlimited Vacation Policy
Paid Volunteer Time
Perks & Discounts
Casual Dress
Commuter Benefits
Company Outings
Game Room
Stocked Kitchen
Some Meals Provided
We cater team lunch every Wednesday and have a fully stocked kitchen the rest of the week!
Happy Hours
Pet Friendly
Professional Development Benefits
Job Training & Conferences
Diversity Program
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