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.

• Provide a variety of consulting and training services to clients • Ensure client satisfaction and successful implementation of software applications • Assist with planning the implementation and developing the project plan • Review existing technology, systems, infrastructure, and data integrity • Work with client personnel to ensure readiness for deployment • Set up and configure applications to meet business needs • Conduct Conference Room Pilots to verify new business processes • Train client personnel, including management and field users • Provide on-going training and application support for users

• Operationalize Onboarding & Reporting • Define onboarding governance models and delivery standards • Establish and manage timelines, milestones, and dependencies in onboarding plan • Align onboarding plans with customer goals, Value Realization Moment, and Year 1 success criteria • Coordinate cross-functionally with CS, AEs, Solution Architecture, and Delivery to ensure aligned execution • Track progress across all active onboardings and maintain end-to-end visibility • Provide clear, consistent reporting on progress, risks, and blockers to customers and Cutover's leadership • Escalations & Communication • Identify delivery risks, delays, or misalignment early across customers and Cutover teams • Drive accountability with customers and Cutover teams to meet onboarding commitments • Ensure blockers are clearly documented, owned, and resolved • Lead timely escalations to the appropriate stakeholders when onboarding outcomes are at risk • Facilitate clear, proactive communication to keep onboarding on track with customers • Onboarding Policy & Continuous Improvement • Own onboarding policies, playbooks, and standards at Cutover • Continuously evaluate onboarding performance, effectiveness, and customer outcomes • Identify recurring gaps or inefficiencies and drive improvement to onboarding processes • Raise onboarding maturity and consistency across teams

This description is a summary of our understanding of the job description. Click on 'Apply' button to find out more. Role Description An exciting and unique opportunity to join a high growth organization with immense career potential. The primary function of this position is to act as our implementation "warrior" where you will be the initial point of contact and Viventium brand ambassador to new clients, promoting our vision and core values, executing them by becoming acquainted with client’s payroll contacts, data and practices, resulting in successfully converting them to our cloud-based HCM software in an accurate and timely manner ensuring a seamless transition to Client Services. The duties of this job require a high degree of specialized expertise and skill in maintaining established standards of quality and accuracy. Drive, determination, and a self-disciplined approach to achieving results that meet these established criteria are necessary for successful job performance. While the pace of the work is faster than average, quality is never compromised. The focus of communication and organizational relationships is based on technical expertise. The work requires specialized technical problem solving and ingenuity while working within approved organizational systems and technology, and the demonstration of the values of integrity, quality and caution. New ideas and concepts are also important but will be carefully analyzed and tested before communication and adoption. The position encompasses a span of control and opportunity for someone who engenders trust, demonstrates a sense of urgency and assures consistent achievement of quality standards. The work requires making decisions that support company guidelines authoritatively and quickly. Qualifications - Ability to handle multiple implementations at one time - Average company size exposure: up to 50-250 people - Ability to handle all aspects of implementation: Basic knowledge of PTO, GL, Wage Parity, Time and Attendance, custom reports, taxation, data extraction and manipulation, file uploads - Excellent attention to detail, time management, organization and prioritization skills - Proficiency in Microsoft Office Suite (Outlook, Word, Excel) - Excellent project management skills - Strong sense of ownership and results oriented - Strategic thinker with ability to understand and communicate client requirements and find corresponding solutions - Troubleshooting and problem-solving experience - Ability to handle escalations with minimal to no supervision - Experience managing simultaneous projects with 3rd party vendors Requirements - 1+ year(s) of experience in payroll/HCM - 1+ year(s) of experience in payroll implementation - Experience with HealthCare Industry and Unions Essential Duties and Responsibilities - Manages the collection and review of new client paperwork for proper format and completion to ensure the integrity of the intake process is upheld - Identifies possible errors in new client paperwork, effectively communicates and/or escalates to the appropriate team members (i.e., Clients, Implementation and/or Tax partners) to resolve as needed (i.e., resource coordination) - Conduct/compose launch calls/emails setting proper client expectations - Comprehensive analysis ensuring completion and accuracy of submitted new client data - Utilize payroll knowledge to streamline client experience and ensure compliance with payroll best practices, Tax (Federal, State, Local), FLSA and ACA laws - Schedule and confirm follow-up calls, client training, the first process and check dates - Enter new client information in the system according to documented procedures - Collect, enter and balance previous year-to-date payroll and employee information - Setup all value-add services such as Direct Deposit, Tax Service, PTO, ESS, etc. - Support client training on software ensuring comprehension of applicable features, as needed - Offer client support for first few payrolls ensuring client comfort level with the process - Oversee transition to client service which includes hand-off email/call with client and CSR - Collaborate and support teammates maintaining a positive work relationship - Participate in special projects and department initiatives as requested - Maintains strict confidentiality of sensitive client data - Attend annual Implementation bootcamp in person