Head of Operations

Location: Chicago, IL Department: Operations Type: Full Time

About Sittercity

Sittercity’s mission is to make child care finally work. We pioneered the child care technology category in 2001, and we connect millions of parents with babysitters and nannies every year. With Sittercity and Chime, our on-demand service, we are building a platform that brings revolutionary simplicity to the way we find, book and pay for trusted care. Headquartered in Chicago, we serve families and caregivers nationwide.

Job Description

We are looking for a leader who breathes operational excellence and is eager to put their best in class operations experience to use solving an important problem - and making child care finally work!  This role is responsible for building and running operations for our marketplace. The right person for this role will possess strong analytical and problem-solving skills, a strategic mindset, and will find simple innovative solutions to complex operational problems. This person knows how to prioritize and doesn’t need to be told how to operate- they treat company resources like their own and and are rigorous when it comes to understanding and improving our business.

The ideal candidate will have people leadership experience and several years experience in tech, consulting or finance.  Experience with on demand services or sharing economy companies would be a plus.


  • Strategize – Devise and execute the overall strategy for the supply side of the business
  • Systematize- Decide what to systematize and what not to, be rigorous in automating and optimizing the right things and saying no to one-offs
  • Analyze – Build models to evaluate the economic and strategic costs and benefits of various sitter acquisition, engagement, retention programs and experiments
  • Lead- Manage a team of Operations Managers that work to strengthen our product, streamline processes, and improve the way we do things
  • Experiment- Use data-driven decision making and sound business judgment to test assumptions

About you:

  • Self-Starter- ability to work independently, thrive in a fast-paced environment, and represent the voice of operations with the executive team
  • Curious- always looking for ways to innovate and improve
  • Entrepreneurial- you love responsibility and want to shape the vision and direction of the company and aren’t afraid to do it
  • Gritty- you roll up your sleeves and do whatever it takes to make things successful
  • Problem Solver- you independently notice and work to solve complex and ambiguous problems with a bias for action.


  • 6+ years of experience in consulting / strategy / operations / technology / banking / analytics or related experience; high-growth or early-stage start-up experience is a plus
  • Proven track record of leading initiatives, hitting goals, and succeeding in a team environment
  • Startup and consumer facing product experience
  • Bachelor’s degree, with MBA preferred
  • Excellent Excel skills; SQL knowledge is a plus, but not required

Our Workplace

Sittercity is a recipient of the 2016 WorldatWork, Work-Life Seal of Distinction Award for demonstrated leadership in workplace strategies and practices to help employees achieve success in work-life effectiveness. 

Sittercity is an Equal Employment Opportunity Employer 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. 

Sittercity participates in E-Verify and background checks all employees. 

* Required fields
First name*
Last name*
Email address*
Phone number*

Attach resume as .pdf, .doc, or .docx (limit 2MB) or paste resume

Paste your resume here or attach resume file