Senior Systems Administrator (remote or NYC)

Location: New York, NY

Department: Engineering

Type: Full Time

Min. Experience: Experienced

Job Description

You’ll be joining our Infrastructure Team, responsible for keeping Olo’s food ordering and delivery systems up and running reliably and securely.


Our DevOps-oriented team uses Infrastructure-as-Code with automation wherever possible. The system has many moving parts and frequent deployments.



  • Proactively monitoring all systems for uptime and security. Noticing trends before they become issues. Improving Monitoring infrastructure as needed.
  • Responding to PagerDuty alerts as part of an on-call rotation with another engineer. Resolving or escalating production issues to development teams as needed.
  • Trying to outsmart our security penetration testing “red team” by constantly improving security implementation.
  • Forecasting and optimizing capacity and AWS infrastructure costs.
  • Required Skills/Experience
  • At least 2 years experience administering a 24/7 web application
  • Expert level Windows Server knowledge, including Active Directory, Windows Server Failover Cluster and Windows Networking
  • In-depth working experience with AWS services and APIs
  • Comfortable in your scripting tool of choice - PowerShell, Python, Bash etc.
  • At least mildly comfortable in a Linux environment
  • Experience designing and creating build pipelines (TeamCity, Jenkins, Octopus)
  • Solid networking knowledge, capable of troubleshooting all types of network traffic issues.
  • A passion for uptime



  • Experience with any of the following technologies: Ansible, CloudFormation, GitHub, SQL Server, Redis, ElasticSearch, SumoLogic, Datadog, Windows Server Failover Clustering, Consul, Docker
  • PCI compliance experience


This position can be remote based or based out of our NYC office.


Olo is located at 26 Broadway in the historic Standard Oil Building, the former home of John D. Rockefeller.  We offer great benefits, such as 20 days of Paid Time Off, fully paid health, dental and vision care, stock options, a generous parental leave plan, and perks like FitBits, rotating craft beers on tap in our kitchen, and food events featuring our clients' menu items (now you know why we give out FitBits!).


We are an equal opportunity employer and value diversity at our company. We do not discriminate on the basis of race, religion, color, national origin, gender, sexual orientation, age, marital status, veteran status, or disability status.

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