Demo

Windows System Engineer

FreshDirect
FreshDirect Salary
Bronx, NY Full Time
POSTED ON 12/28/2025
AVAILABLE BEFORE 2/2/2026
Brief Description

About Us

At FreshDirect, we are reinventing the grocery experience. Since day one, our mission has been simple: bring the best, freshest food directly from the farm to people’s home – faster, fresher, and smarter than anyone else.

We are not just a food company – we are a technology powered, customer obsessed team building the most innovative end to end food supply chain in the industry. From proprietary routing systems to our state of the art fulfillment center, every part of our business is designed to deliver unmatched quality, convenience and care.

We partner directly with farmers, fishermen, and artisans to source the highest quality ingredients, then use smart data, automation, and logistics to get them to our customers’ door at peak freshness. It’s grocery shopping reimagined and we are just getting started.

If you are passionate about innovation, care about what people eat, and want to be part of a team doing what no one else is doing, come build future of food with us.

The Role

We are seeking a highly skilled Windows System Engineer to join our dynamic IT team. This role is crucial for maintaining, troubleshooting, and optimizing our Windows-based infrastructure to support business operations and ensure seamless performance across the organization.

What You’ll Do

  • Manage the full lifecycle of Windows server systems, including setup, upgrades, and decommissioning.
  • Configure and oversee user access, roles, and permissions to ensure the integrity and security of the infrastructure.
  • Regularly update and patch servers to maintain system health and reduce vulnerabilities.
  • Continuously monitor system performance using industry-standard tools to identify and address potential bottlenecks.
  • Implement and manage proactive alerting systems to prevent downtime or performance degradation.
  • Design and apply security measures such as firewalls, antivirus programs, and intrusion detection systems.
  • Conduct routine audits and vulnerability assessments to identify risks and develop mitigation strategies.
  • Collaborate with the cybersecurity team to respond swiftly to security incidents and breaches.
  • Establish and maintain robust backup and recovery procedures to ensure business continuity.
  • Create, test, and deploy PowerShell or other script-based solutions for automating repetitive tasks such as user management, server configurations, and log analysis.
  • Develop tools that streamline processes and enhance the efficiency of daily operations.
  • Partner with network engineers, application developers, and other IT teams to design solutions that meet business needs and align with IT standards.
  • Participate in strategy meetings and contribute expertise on system capabilities and limitations.
  • Serve as a subject matter expert to resolve complex technical issues, both during normal operations and in incident response scenarios.
  • Diagnose and rectify software and hardware issues with Windows servers and related technologies.
  • Keep a log of incidents and their resolutions for future reference and training purposes.
  • Develop comprehensive documentation, including server configurations, process flows, technical guidelines, and standard operating procedures.
  • Lead or assist in IT infrastructure projects, such as server upgrades, data center migrations, and the rollout of new services.
  • Coordinate with stakeholders to gather requirements, establish timelines, and deliver results within deadlines.
  • Provide technical input to ensure projects align with overall IT strategy and business goals.
  • Partner with network engineers, application developers, and other IT teams to design solutions for chosen cloud providers which utilize industry best practices.
  • Implement cloud-based solutions utilizing IaC leveraging automation tools such as github and terraform.
  • Server as subject matter expert for cloud-based infrastructure and services

What You Bring

  • Minimum of 10 years of experience in Windows system administration or engineering.
  • Bachelor's degree in Computer Science, Information Technology, or a related field (or equivalent experience).
  • Strong expertise in Windows Server (2016/2019/2022), Active Directory, Group Policy, and server virtualization technologies (e.g., VMware, Hyper-V).
  • Relevant certifications such as Microsoft Certified: Windows Server Hybrid Administrator Associate or similar are preferred.
  • Proficient in scripting and automation (PowerShell, Terraform, etc).
  • Familiar with git version control (Github, Gitlab, Bitbucket, etc)
  • Familiarity with monitoring tools (e.g., SolarWinds, Nagios).
  • Excellent problem-solving and analytical skills.
  • Strong interpersonal and communication skills.

What We Offer

  • The expected compensation for this role is ($135,824 to $159,793) per year, depending on experience and qualifications. Final compensation will be discussed during the interview process.
  • Time Off: PTO, Safe & Sick Time, and Paid Holidays.
  • Health Benefits: Medical, vision, dental and voluntary disability benefits.
  • Financial Benefits: 401(k) employer match and life insurance.
  • Location: Our state-of-the-art campus is located in the Bronx, featuring an on-site gym, cafeteria and an employee market. We offer free on-site parking and provide an employee shuttle service from nearby MTA stations.
  • People Investment: We offer job training to our operations and transportation team members to facilitate career advancement. Additionally, we invest in leadership development programs that provide opportunities for professional growth. We have also partnered with local colleges to offer tuition discounts.
  • Perks: Employees can take advantage of a 20% employee discount on online orders and at our wine store. Our on-site employee market showcases our products at substantial markdowns. Additionally, we organize vendor spotlights and engagement events that give employees the opportunity to experience our products firsthand.

Our Culture

We embrace an in-office culture, composed of individuals who thrive on the collaboration and energy that comes from working together in a shared space. We are looking for people who excel in this environment, where physical presence enhances connections and engagement. At FreshDirect, we've created an environment that thrives on teamwork, where associates can innovate, grow, and have successful careers. Many of our leaders have successfully come up through our ranks. Because of our team's extraordinary efforts, we are a leading innovator in the e-commerce and grocery industries.

Equal Opportunity

We are proud to be an equal opportunity employer. Fresh Direct, LLC and its affiliates do not discriminate against applicants or employees because of their race, color, citizenship status, national origin, ancestry, gender, disability, sexual orientation, age, religion, creed, marital status, veteran status, domestic violence victim status, political affiliation, or any other factor protected by federal, state, or local law.

Disclaimer

The above statements are intended to describe the general nature and level of work being performed by the Team member(s) assigned to this position. They are not intended to be an exhaustive list of all responsibilities, duties, and skills required of individuals in this position. Position Expectations may be subject to change as the needs of the organization changes.

Salary : $135,824 - $159,793

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