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Boston, MA

Systems Engineer III (Automation) at Chewy

| Greater Boston Area
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Our Opportunity:

Chewy is seeking a driven, high-energy and self-starting Sr. Systems Engineer to join our fast-paced Enterprise Systems Engineering team in 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
  • Act as an authority on your domain expertise; combining expert-level proficiency with the ability to communicate clearly and collaborate to turn broad requirements into deliverable work items
  • Author, maintain, and leverage automation scripts with languages such as PowerShell, Python, JSON, XML, etc.
  • Develop custom automations between disparate 3rd-party SaaS app APIs using Workflow automation platforms such as MS Flow, Okta Workflows, and Torii
  • 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
  • Define and maintain corporate VMware templates, standards, and system documentation
  • 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
  • Perform and provide progress on project deliverables, tasks, and milestones as well as provide project documentation such as Built-As, architecture diagrams, and runbooks
  • 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, 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 leadership to gather ROI and complete whitepapers to justify purchase approval
  • 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
  • Represent team recommendations to leadership, demonstrate influence over governance bodies, and coach on communicating technical issues, impact, and risk mitigation strategies in business terminology that non-technical resources can understand
  • 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
  • 7 years being responsible for designing, implementing, and upgrading Active Directory and related services
  • 4 years being responsible for robust M365 Enterprise Mobility environments, including Azure AD, Exchange Online, Email Gateway/Archiving, SharePoint Online, and OneDrive
  • Experience working with Infrastructure-as-code technologies such as Ansible, Stackstorm, Terraform, Jenkins
  • 5 years working with automation and integration technologies such as PowerShell, Python, XML, JSON, Soap, API, SFTP, GitHub, Okta Workflows, MS Flow. 
  • Demonstrated ability to produce PowerShell Functions and Modules
  • Solid understanding of network concepts and troubleshooting skills, DNS, IP, subnetting, and DHCP
  • The utmost passion for technology and a thirst for knowledge and growth
  • Ability to work well within a team; good interpersonal relational and collaboration skills
  • Knowledge of downstream integrations to gauge the impact of changes, triage and remedy incidents and/or scope level of effort for new initiatives
  • Knowledge of VMware technologies
  • Have hands-on experience in grooming/mentoring individuals and being the bar raiser in the team
  • Demonstrated attention to detail with the ability to design and develop solutions to meet business needs creatively
  • Customer Service focused approach to interactions with business partners and employee user community
  • Strong organizational and time management skills
  • Demonstrated success managing a fast-paced, high-performance and deadline-driven engineering team
  • 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 environment
  • Ability to discuss complex technical concepts with technical staff, stakeholders, and business executives in a simple, straightforward manner
  • Familiar with current security protection, encryption, monitoring/auditing, and remediation techniques with the proven ability to oversee solutions for the network, servers, databases, and the desktop
  • Familiar with disaster recovery, business continuity, and high availability concepts
  • 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 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
  • Experience working with Varonis
  • Working knowledge of Linux operating system
  • Knowledge of project management and agile software development methodologies, experience with JAMF, Confluence, LucidCharts, and ServiceNow
  • Experience in SAN storage technologies and integration with VMware
  • VMware certification
  • Experience with encryption solutions such as Dell DPE, Bitlocker, and Filevault
  • Experience managing 3rd party hardware and software vendors and providers
  • Experience with Security and Compliance concepts such as eDiscovery, DLP, and CASB
  • Experience with Microsoft Power Platform
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 [email protected] 
To access Chewy’s Privacy Policy, which contains information regarding information collected from job applicants and how we use it, please click here:
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Where we are

Located in the Fort Point neighborhood, home to many of Boston's hip and upcoming restaurants along with emerging technology companies.

Technology we use

  • Engineering
  • Product
  • Sales & Marketing
    • JavaLanguages
    • JavascriptLanguages
    • KotlinLanguages
    • PHPLanguages
    • RLanguages
    • ScalaLanguages
    • SqlLanguages
    • SwiftLanguages
    • jQueryLibraries
    • VueJSLibraries
    • AngularJSFrameworks
    • DjangoFrameworks
    • HadoopFrameworks
    • Node.jsFrameworks
    • SpringFrameworks
    • GRPCFrameworks
    • Microsoft SQL ServerDatabases
    • MySQLDatabases
    • OracleDatabases
    • PostgreSQLDatabases
    • RedisDatabases
    • VerticaDatabases
    • AerospikeDatabases
    • Google AnalyticsAnalytics
    • BalsamiqDesign
    • IllustratorDesign
    • InVisionDesign
    • PhotoshopDesign
    • SketchDesign
    • UXPinDesign
    • ConfluenceManagement
    • JIRAManagement
    • dotCMSCMS

What are Chewy Perks + Benefits

Chewy Benefits Overview

We offer competitive salaries and 401k, unlimited time off, comprehensive medical, dental, and vision benefits, in addition to wellness programs, online communities, and resources for improved physical and mental health... enabling you to be your best self - in and outside of work. With mentorship programs, employee resource groups, cross-functional job trainings, events, and customized development tracks for advancement, we're proud to help develop and promote our team members from within.

True to our business, we're pet-friendly and have fun pet-related perks like Paw-ternity leave for new pup parents and Chewy employee discounts. We offer countless volunteer opportunities, recreational club teams, company outings, happy hours, and team events to enable you to bond with fellow Chewtopians and have some fun!

Volunteer in local community
Partners with Nonprofits
Friends outside of work
Eat lunch together
Intracompany committees
Daily sync
Open door policy
Team owned deliverables
Team based strategic planning
Group brainstorming sessions
Pair programming
Open office floor plan
Dedicated Diversity/Inclusion Staff
Highly diverse management team
Unconscious bias training
Diversity manifesto
Diversity Employee Resource Groups
Hiring Practices that Promote Diversity
Health Insurance & Wellness Benefits
Flexible Spending Account (FSA)
We offer a commuter transit, parking, and dependent care FSA.
Disability Insurance
Dental Benefits
Vision Benefits
Health Insurance Benefits
Life Insurance
Pet Insurance
Wellness Programs
Mental Health Benefits
Retirement & Stock Options Benefits
401(K) Matching
Company Equity
Performance Bonus
Child Care & Parental Leave Benefits
Generous Parental Leave
Flexible Work Schedule
Remote Work Program
We're currently 100% remote due to caution and care for the health & well-being of our team. Post-pandemic, we plan to operate in a combination of onsite and remote, with logistics still being defined
Family Medical Leave
Return-to-work program post parental leave
Vacation & Time Off Benefits
Unlimited Vacation Policy
Paid Holidays
Paid Sick Days
Perks & Discounts
Beer on Tap
Casual Dress
Commuter Benefits
Company Outings
Game Room
Stocked Kitchen
Some Meals Provided
Happy Hours
Pet Friendly
Recreational Clubs
Chewy sponsors office sports leagues year-round.
Relocation Assistance
Professional Development Benefits
Job Training & Conferences
Diversity Program
Lunch and learns
Cross-functional lunch and learns.
Cross functional training encouraged
Promote from within
Mentorship program
Time allotted for learning
Online course subscriptions available
Customized development tracks

An Insider's view of Chewy

What’s the vibe like in the office?

Fast paced! We work in "doggy-years" here. It's a place where talent and hard work is valued and where team members can think big and can bring their dreams to life.


Senior Technical Recruiter

What kinds of technical challenges do you and your team face?

At Chewy, one of our operating principles is Accelerate Time. We release new features weekly, fail fast, and iterate often to bring incremental progress quickly to our Pet Parents. Our success is driven by a customer first mentality, a culture of collaboration, and empowering individuals and teams.


Associate Director, Product Management

How does the company support your career growth?

Chewy gives a significant amount of freedom and autonomy to do your best work. I am able to pursue the most important objectives, and work that I really enjoy. It’s an amazing feeling to see your hard work pay off immediately and have a positive impact on the team—and something that makes life at Chewy really unique!


Human Resources Business Partner

How do you make yourself accessible to the rest of the team?

Aside from the standard 1x1s and team meetings: 24/7 via text, email, chat, voice and during business hours by walking around the office engaging in conversation, listening to current challenges and proposed solutions.


VP, Software Engineering

What projects are you most excited about?

Collaborating with so many different teams on a daily basis and seeing how we all come together to help pet parents find the products that they need for their pets.


Senior Integrated Marketing Manager

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