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Director of Technology Operations

Technology | Chicago, IL | Full Time

Job Description

Director of Technical Operations


Sittercity is a dynamic, rapidly growing Internet based company located in Chicago, IL.  We are looking for a Director of Technical Operations to manage Sittercity’s growing production and development operations team with the goal of keeping the site available, scalable, and secure. The role will work to refine operational policies & procedures, set infrastrucure strategy, and participate early in software design.

Key Responsibilities:

  • Lead production operations, taking responsibility for Sittercity’s infrastructure and services
  • Lead development operations including release management and continuous delivery
  • Manage a small team of system engineers
  • Develop and execute technical operations procedures
  • Responsible for maintaining service levels, availability, capacity, security, performance, and change management of the production and test environments
  • Manage procurement and budget of hardware and services related to systems and software architecture.
  • Design, implement, and maintain production systems


  • 8+ years in system engineering / system administration, 3+ managing.
  • Experience experience with production web topologies, networking, protocols
  • Experience with Linux, Apache, Ruby, MySQL
  • Experience with project management and prioritization
  • Experience with security management and standards such as PCI
  • Demonstrated ability to communicate technology issues to non-technical audiences
  • Excellent oral and written communication skills


  • Proven success in web based startup environments
  • Deep understanding of IaaS architectures, specifically AWS offerings.
  • Interest in DevOps and Continuous Delivery

We operate in a casual and fun environment in River North.  Perks include weekly on-site yoga classes, unlimited healthy snacks, weekly lunches, and quarterly outings.  In addition, we offer a very competitive benefits package including Health, Dental, Vision, Short-Term Disability, Long-Term Disability, and Life Insurance as well as 3 weeks of paid time off to start.

Sittercity is an Equal 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.

Interested applicants, please apply at