Chief Technology Officer at Gaggle


Chief Technology Officer (CTO)
Remote (US)

Job Summary:
Join the Gaggle team and help make a difference in the lives of K-12 students throughout the United States! Gaggle has a long track record of success in schools and has been growing profitably at more than 20% each year. We’re a group of about 100 dedicated people creating superior technology to assist schools in preventing bullying, school violence and self-harm such as cutting and suicide. The work is unequivocally worthwhile – we saved 722 student lives last year alone.

We’re looking for someone with a thirst for both excellence and purpose – someone who works well remotely, is motivating to a team of highly skilled individuals and who wants to stay with an established company for 5+ years. Our top candidate will have experience leading a technology team that has adapted to increasing YOY company growth (both financial and headcount).

As the Chief Technology Officer (CTO), not only will you be responsible for overseeing all technical aspects of the company, but you’ll be helping to lead an organization that offers what other tech start-ups or IT roles cannot: a remote, flexible work environment, a stable job in what is otherwise a constantly changing field as well as a chance to make a real difference in the lives of millions of students across the country. Not only that, but you’re leading a fantastic team of twenty-eight USA-based tenured, talented and dedicated individuals (such as System Administrators, Java Developers and Machine Learning Engineers, to name a few) who want to see Gaggle succeed and are invested in your leadership.

Baseline CTO Requirements:

  • In collaboration with the Chief Executive Officer, the CTO leads all aspects of Gaggle’s technological development
  • Highly proficient in the technology we use: Java, JetBrains, mySQL, Atlassian Tool (Jira & Confluence), Slack, Tableau and Amazon Web Services
  • 5+ years leading a remote-based engineering team of 60+ SaaS IT professionals
  • Experience challenging a tenured, experienced team to adapt to change; more essential to be able to hold team accountable than to be popular
  • Won features wars against competitors that were PE-backed or funded
  • Successfully managed technical debt and migrated from data centers to AWS
  • Acts as a leader: the CTO actively communicates, inspires, values and motivates all levels of staff as well as thinking and acting both strategically, collaboratively and proactively
  • Possesses strong writing and presentation skills
  • Works in a consultative fashion with other department heads as an adviser of technologies that may improve efficiency and effectiveness
  • Provides leadership to department heads in a fashion that supports Gaggle’s culture, mission and values
  • Does not see him/herself as the Product Manager; can take direction and get things built
  • Is a true engineer at heart – still checks in codes at least 2x annually
  • Conducts research and case studies on leading-edge technologies and makes determinations on the probability of implementation
  • Acts as a good steward of Gaggle’s resources and ensures control of IT departmental budgets
  • BS in related field and at least 15 years’ experience in the Information Technology arena, at least 10 years management and strategic experience in this field; alternatively, MBA/MS in related field with 10 years’ experience, 7 of which must be managerial and strategic

Please note: although this is a remote role, the successful candidate must reside in and be authorized to work in the United States.


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