System Support Engineer (Remote, United States)

Gaggle • Remote • Yesterday

At Gaggle, we’re on a mission to help schools prevent suicide, self-harm, violence and bullying. As a Systems Support Engineer at Gaggle, you’ll serve as an integral part of a critical team your peers, other Gaggle teams, and the schools we serve. Using a combination of internal tools, critical thinking, and your knowledge of Device Management, you’ll help Gaggle save student lives by facilitating new customer onboarding, troubleshooting customer configurations, and acting as the primary liaison between Engineering and the rest of the organization.

Note: At this time, we are only able to consider candidates that live in and are authorized to work within the United States, and do not require sponsorship.


Here’s how we like to work:

  • Favor a proactive, customer-oriented approach to problem solving, valuing collaboration over rigid requirements
  • Leverage automation to build procedural, repeatable, and well-documented solutions to frequent tasks
  • Support our peers and other teams through understanding, accepting challenges and assessing as a team to identify solutions
  • Foster a growth-centric environment, challenging ourselves to learn new technologies, optimize the ones we already use, and invent new tooling where it doesn’t already exist
  • Meet with district technical contacts to improve and reduce timelines for new service enablement.
  • Collaborate through Slack, Google Meet, Jira, and GitHub


We will look to you to help us solve challenges such as:

  • Assist customers in the deployment of new product offerings by creating processes, custom tooling and scripts
  • Work with other internal Gaggle teams to onboard new customers and troubleshoot existing customer implementations
  • Interacting directly with databases to extract information, perform updates, and troubleshoot tasks
  • Add to and improve custom tooling to reduce risk and streamline commonly-executed tasks
  • Work with Engineering to triage, diagnose, and prioritize bugs and other system issues, recommending solutions when presenting challenges
  • Improve and contribute to internal documentation, enforcing standards, ensuring quality, and empowering employee self-service


Required Skills:

  • PowerShell experience
  • Enterprise Device Management experience
  • Customer Enablement Experience
  • Strong critical thinking
  • Bash scripting experience
  • Basic SQL knowledge
  • Excellent communication skills, both written and verbal
  • Experience with Google Workspace and Azure by way of the administration tools


Preferred Skills:

  • Linux, any flavor
  • Knowledge of ticketing and help desk solutions such as Salesforce, JIRA
  • Previous technical support experience
  • AWS console/cli experience
  • District K-12 IT Experience
  • Solutions Engineering around Web Filter or Similar Technologies


Salary Range and Benefits

Please apply to this posting in order to learn more about the starting salary range and benefit options. Some benefits highlights:

  • We’re a remote-first company; our team works together across all 50 US states
  • PPO and HDHP health insurance plans through BCBS of Illinois; coverage includes treatment for fertility (including IVF) as well as offering virtual visits and mental health resources
  • Dental insurance (including orthodontia) through Guardian
  • Vision insurance through BCBS/EyeMed
  • HSA, FSA, LPFSA, and DCFSA available, with a $500 annual company contribution
  • 401(k) plan with immediate vesting and a 4% company contribution with each paycheck
  • Employee Assistance Program through Paychex and Guardian (includes financial and legal assistance)
  • Flexible PTO
  • Generous, 100% to 70% paid leave plans, up to 90 days
  • Pet Insurance Discount Program
  • Fun perks such as team recognition programs, holiday gifts and bonuses, company retreats, raffles, and fantasy football leagues

Our Team Commitment

Gaggle is proud to be recognized as a 2023 Top Workplace and also a proud recipient of the 2024 Top Workplaces USA Today award. We are committed to equal opportunity without regard to age, race, creed, color, national origin, ancestry, marital status, affectional or sexual orientation, gender identity or expression, disability, nationality, or sex.

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