Agent & Extension Deployment Specialist

Gaggle is seeking an Agents & Extensions Deployment Specialist to lead the technical deployment of agents and browser extensions that power both Gaggle’s Web Filter and Safety Management solutions.

This role owns the end-to-end technical implementation of endpoint agents and browser extensions across district-managed devices. The specialist will work directly with district IT teams to plan, deploy, validate, and optimize installations to ensure accurate filtering, monitoring, and student safety coverage.

This position is specifically focused on technical deployment execution, including device-level rollout strategy, policy configuration, extension management, authentication validation, and post-deployment verification.

The ideal candidate has hands-on experience deploying endpoint agents, browser extensions, or security tools in a K–12 or enterprise environment and understands device management ecosystems such as Google Admin Console, Microsoft 365, and MDM platforms.

Key Responsibilities

Technical Implementation & Deployment Ownership

• Own and manage implementations focused on:
  • Web Filter and Safety Management deployments, which include:
    • Chrome/Edge/Safari browser extension rollouts
    • Microsoft Agent deployment
    • OS Agent deployment
• Develop and manage deployment plans tailored to each district’s device ecosystem (Chromebooks, Windows, Mac) and MDM.
• Guide IT administrators through:
  • Agent installation methods (manual, scripted, or MDM-based)
  • Extension deployment via Google Admin or Microsoft Admin tools
  • Organizational Unit targeting and user scoping
  • Authentication and policy validation
• Ensure proper configuration for both:
  • Web filtering enforcement
  • Safety monitoring visibility and alert accuracy
• Validate successful installations and confirm correct data flow and policy application before closing implementation.

Project Management

• Manage multiple deployment projects simultaneously while maintaining clear timelines and milestone tracking.
• Ensure implementations are completed within 60 days of purchase.
• Lead structured onboarding calls focused on deployment planning and technical execution.
• Identify risks to timeline or technical success and proactively coordinate with internal teams to resolve issues.
• Maintain detailed implementation documentation within CRM and internal systems.
• Provide clear handoff notes to Customer Success once deployment is complete.

Customer & IT Stakeholder Management

• Establish a consistent communication cadence with district IT teams.
• Serve as the primary technical advisor during deployment.
• Translate technical requirements into actionable, step-by-step guidance.
• Escalate at-risk accounts internally with a recommended action plan.
• Monitor deployments for 30 days post-go-live to ensure stability and proper coverage.

Technical Experience (Required or Strongly Preferred)

Experience deploying or administering:

• Endpoint agents (security, monitoring, or filtering tools)
• Browser extensions at scale
• Web filtering or cybersecurity solutions

Hands-on experience with:

• Google Workspace Admin Console
• Microsoft 365 / Azure AD
• Device management systems (Intune, JAMF, Google Admin MDM, etc.)
• Organizational Unit and policy-based deployment strategies

Understanding of:

• DNS filtering and web filtering principles
• Endpoint security fundamentals
• Authentication and identity management
• K–12 device environments and student device management best practices

Experience working in a K–12 district technology department is strongly preferred; equivalent private-sector experience is also valuable.

Skills & Qualifications

• Strong organizational and project management skills.
• Ability to manage multiple technical deployments concurrently.
• Excellent written and verbal communication skills.
• Comfortable leading technical conversations with IT Directors and System Administrators.
• Detail-oriented with strong follow-through.
• Ability to work independently in a fully remote environment.

Education & Experience

• Bachelor’s degree or equivalent professional experience.
• 3+ years in a technical, customer-facing role (implementation, systems administration, IT consulting, or technical account management).
• Proven experience managing onboarding or deployment projects.
• Experience using CRM systems (Salesforce preferred).
• Prior K–12 edtech or cybersecurity experience is a plus.

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.