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Lead Software Developer

Technology | Chicago, IL

Job Description

Lead Software Developer

Sittercity enriches the lives of children and seniors by helping people connect with amazing caregivers safely, quickly, and efficiently.  Help us make these bonds even stronger. 

Do you have battle scars from many years of making real, production code, but still get excited at the idea of writing something new? Have you learned how to excite, energize (and perhaps wrangle) other team members into amazing feats of code of their own? Do you love watching the team build something amazing, while rolling up your own sleeves and diving in?

You just might be what we're looking for. We have a team of exceptionally talented software engineers who've just moved over from PHP to Rails, and who would jump at the chance to learn from you and your wise experience. We've recently started a green-field project, so you'll get to help mold the code base from the beginning.


  • Lead a team of 4-5 Rails engineers in taking a new product idea from concept through development and beta launch.
  • Guide a team of extremely talented software engineers of differing levels of experience as they learn Rails (coming from PHP); a core part of this job is helping engineers to grow and learn in their own ways while making sure the project remains solid, reliable, and robust.
  • Facilitate and participate in collaborative technical design of the project, in everything from coding standards and libraries through overall architecture and data-storage systems. Apply pragmatic decision making to maximize coding velocity, while ensuring technical design does not suffer.


  • Bachelor's degree or higher in Computer Science
  • 5+ years of professional experience, with 8+ strongly preferred
  • At least 1-2 years of experience working as a technical leader or manager among teams
  • Experience and knowledge implementing solutions on Rails stack
  • Experience with agile software engineering methodologies
  • Excellent verbal and written communication skills
  • Strong interpersonal and leadership skills


Our Workplace: 

We operate in a casual and fun environment in the River North neighborhood of Chicago.  Perks include weekly on-site yoga classes, unlimited healthy snacks, weekly lunches, quarterly outings and work-at-home Fridays.  In addition, we offer a very competitive benefits package including Health, Dental, Vision, Short-Term Disability, Long-Term Disability, Life Insurance, 401(k) as well as 3 weeks of paid time off to start. 

Sittercity is a Recipient of the 2012 Work-Life Seal of Distinction Award from the Alliance for Work-Life Progress.                                                                      

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 and conducts background checks on all employees.

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