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Chewy Senior Systems Engineer in Boston, Massachusetts

Our Opportunity:

Chewy is seeking a driven, high-energy and self-starting Senior Systems Engineer to join our fast-paced Enterprise Systems Engineering team in Dania Beach, FL, Minneapolis, MN, or Boston, MA. In this role, you will serve on a team of subject matter experts who design, build, test, deploy, and support Chewy’s foundational Enterprise Systems including core applications and technologies.

You will work with IT Operations, Service Delivery, IAM, and Site Support teams to provide mentoring, documentation, analysis, process creation, and resolution of escalated incidents. In some cases, you may act as a liaison between cross-functional business and technology teams, and be responsible for translating complex business needs to effective technical design recommendations, system/data analysis, configuring design in systems, and leading or participating in testing and deployment activities.

You will leverage your deep technical expertise to understand process and systems requirements to support and drive new functionality and enhancements within existing systems, as well as help the business scope and implement new systems and develop new integrated solutions.

What You'll Do:

  • Design, deploy, administer, monitor and enhance foundational Enterprise systems including technologies such as Active Directory, Group Policy, DNS, DHCP, file & print services, Microsoft 365, Email-related systems (Exchange, Mimecast), Microsoft Server, and patch management

  • Administer Chewy’s robust Okta landscape, including curating Zones, Policies, and building SAML and OIDC integrations for 3rd-party SaaS and internal Chewy-built apps via the OIN or from scratch, including creating authorization servers with custom scopes and claims

  • Act as an authority on your domain expertise; combining expert-level proficiency with the ability to communicate clearly to translate business requirements into solutions

  • Utilize experience to author, maintain, and leverage automation scripts with languages such as PowerShell, Python, JSON, XML, and other DevOps-related languages

  • Develop custom automations between disparate 3rd-party SaaS app APIs using Workflow and DevOps platforms such as MS Flow, Okta Workflows, and Torii

  • Perform and provide progress on project deliverables, tasks, and milestones as well as provide project documentation such as Built-As, architecture diagrams, and runbooks

  • Diagnose and resolve issues while identifying recurring issues or processes that can be remediated through automation

  • Troubleshoot system functional and operational issues as well as maintain the system operations at all times

  • Produce, maintain and update knowledge base documentation, runbooks, and SOPs

  • Identify and take advantage of opportunities to train and mentor various members of Information Technology

  • Act as a primary point of contact for system outages and escalations

  • Work directly with business stakeholders, technical staff and project teams to identify, analyze, design, test and implement new systems or improvements to existing systems and associated procedures

  • Collaborate with the IT Operations, Service Desk, IAM, Site Support, Information Security and other Enterprise Systems team members in the documentation and implementation of processes and procedures for software and hardware asset management for the enterprise system environments

  • Document the landscape and design to facilitate maintenance

  • Participate in on-call after-hours support rotation

  • Perform occasional audits of enterprise systems such as file share permissions and access to sensitive systems

  • Maintain current knowledge of solutions available to perform systems engineering, inventory, monitoring, updates and ongoing maintenance for the organization’s IT systems

  • Review system and software releases for new functionality and test to optimize existing systems, processes and integrations accordingly

  • Champion team success over individual accomplishment

  • Take initiative to develop unique projects in which you get to research new technology, solve more complex problems, perform POCs

  • Work with team members to schedule and report upon the execution of testing and validation efforts as part of a formal release ITIL Change Management process

  • Build strong relationships and influence with vendors, business and technology leaders

  • Keep ahead of emerging trends, understand business area opportunities and challenges, process or system impacts to all related business or systems areas when designing recommended solutions to achieve business objectives

  • Performs other duties as assigned

What You'll Need:

  • A minimum of 10 years experience in IT

  • Knowledge of downstream integrations to gauge the impact of changes, triage and remedy incidents

  • 6 years being responsible for designing, implementing, and upgrading Active Directory and related services

  • 3 years of demonstrated success building and using an Infrastructure-as-code/CICD pipeline using DevOps technologies such as Terraform, Ansible, Stackstorm, Jenkins (or similar), and the code repositories tied to them

  • 5 years being responsible for robust M365 Enterprise Mobility environments, including Azure AD, Exchange Online, Email Gateway/Archiving, SharePoint Online, OneDrive, and the Power Platform

  • 5 years working with automation and integration technologies such as PowerShell, Python, XML, JSON, Soap, API, SFTP, GitHub, Okta Workflows, MS Power Platform. Demonstrated ability to produce PowerShell Functions and Modules

  • Knowledge of project management and agile software development methodologies, experience with JAMF, Confluence, LucidCharts, and ServiceNow

  • Solid understanding of network concepts and troubleshooting skills, DNS, IP, subnetting, and DHCP

  • Familiar with current security protection, encryption, monitoring/auditing, and remediation techniques with the proven ability to oversee solutions for the network, servers, databases, and desktop

  • Familiar with disaster recovery, business continuity, and high availability concepts

  • Ability to work well within a team; good interpersonal relational and collaboration skills

  • Customer Service focused approach to interactions with business partners and employee user community

  • The utmost passion for technology and a thirst for knowledge and growth

  • Ability to handle escalations and friendly resolution of the most complex hardware and software problems

  • Ability to learn quickly and use new complex technical concepts and resolve issues in a rapidly changing, uber fast-paced environment

  • Ability to translate complex technical concepts with technical staff, stakeholders, and business executives in a way they understand

  • Ability to thrive in a pet-friendly open space seating work environment

Bonus (If applicable):

  • A Bachelor's degree in Computer Sciences or equivalent

  • Experience administering Okta and building custom integrations with SAML, OAuth2, OIDC, and SCIM with Okta API Access Management and Device Trust

  • Experience extending and working with Active Directory and Windows in AWS/Azure

  • Experience with SaaS Operations and Spend Management Platforms such as Torii, Productiv, Blissfully, etc

  • Have hands-on experience in grooming/mentoring individuals and being the bar raiser in the team

  • Experience working with Varonis

  • Knowledge of VMware technologies

  • Certification in Microsoft, Okta, or Terraform

  • Experience with encryption solutions such as Dell DPE, Bitlocker, and Filevault

  • Experience managing 3rd party hardware and software vendors and providers (vendor relations)

  • Experience with Security and Compliance concepts such as eDiscovery, DLP, and CASB

Chewy is committed to equal opportunity. We value and embrace diversity and inclusion of all Team Members.

If you have a disability under the Americans with Disabilities Act or similar law, or you require a religious accommodation, and you wish to discuss potential accommodations related to applying for employment at Chewy, please contact

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