Cloud Operations AI Engineer

Job Description

Opportunity Summary:

Upland is hiring a Cloud Operations AI Engineer to help modernize how we operate SaaS applications in AWS. This is a hands-on hybrid role that combines cloud operations, DevOps, and AI-enabled engineering. You will work closely with developers and operations teams to use tools such as GitHub Copilot, AWS Bedrock, and Claude-based assistants to troubleshoot production issues, automate repetitive work, and improve reliability, performance, and availability across our product portfolio.

The ideal candidate has experience operating production SaaS systems on AWS and knows how to apply AI responsibly to accelerate troubleshooting, reduce manual effort, and improve service resilience. This person is comfortable working across infrastructure, automation, observability, and developer collaboration and can turn operational pain points into scalable improvements.

What would you do?

• Partner with developers and Cloud Operations teams to troubleshoot production issues and improve service reliability.
• Use GitHub Copilot, AWS Bedrock, Claude-based tools, and related AI capabilities to accelerate troubleshooting, scripting, and automation.
• Automate manual operational work, including health checks, remediation, reporting, deployment support, patching, and recurring maintenance.
• Improve performance, availability, scalability, and observability across AWS-hosted SaaS environments.
• Contribute to incident response, root cause analysis, corrective actions, and operational documentation.
• Administer complex Microsoft-based web hosting configuration components, including Windows Server configuration, .NET framework, IIS web sites, and SQL Server database servers.
• Create and maintain runbooks, automation documentation, and system configuration records.
• Participate in on-call support for customer-facing SaaS environments and serve as an escalation point for complex issues.
• Promote responsible AI practices by validating output, protecting sensitive data, and applying sound testing and review standards.
  
  

Why this role matters

• Bring an AI-first approach to move faster—paired with strong engineering rigor, testing, and secure practices to help Upland transform our portfolio of products.
• Own automation and tooling that reduces operational toil and improves reliability across environments.
  
  

What are we looking for?

Technical Skills

To be successful in this role, you should have a strong foundation in operating production SaaS systems, a solid understanding of AWS and DevOps practices, and the ability to apply AI effectively to operational engineering challenges. The ideal candidate can move between infrastructure, automation, troubleshooting, and developer collaboration, and can use AI tools to accelerate delivery while maintaining security, reliability, and engineering discipline.

Experience

Overall, 6+ years of experience in DevOps, site reliability, platform engineering, or cloud operations, with hands-on responsibility for AWS-based production environments. A part of experience (~3 years) should include GitHub and GitHub Actions, infrastructure automation, containerized workloads such as EKS and ECS, observability platforms like Grafana and Prometheus, and support for 24x7 SaaS applications.

Primary Skills: The candidate must possess the following primary skills:

AI Development

• Hands-on experience using AI-assisted engineering tools such as GitHub Copilot, AWS Bedrock, Claude-based coding tools, or similar assistants to accelerate scripting, automation, troubleshooting, and operational analysis.
• Ability to use AI to generate, debug, refactor, and validate scripts, runbooks, and automation in languages such as Python, Bash, and PowerShell, while applying testing and peer review.
• Experience applying AI to investigate performance bottlenecks, failure patterns, alert noise, and availability risks in production systems.
• Strong understanding of responsible AI usage, including protection of sensitive data, prompt hygiene, output validation, and review of AI-generated code for security, cost, and operational reliability.
  
  

DevOps / Automation

• Experience automating manual operational work such as health checks, remediation steps, patching processes, reporting, recurring maintenance, and deployment support through scripts, workflows, Lambda functions, or related tooling.
• Strong experience with Infrastructure-as-Code technologies; Terraform is required, and Ansible is a plus.
• Experience building or maintaining CI/CD workflows and operational automation that improve consistency, reduce toil, and support reliable production changes.
  
  

AWS/Public Cloud

• Strong production experience with Amazon Web Services in a 24x7 SaaS environment.
• Experience designing, operating, and improving AWS-based application and infrastructure services, including the introduction of new services into existing production environments.
• Hands-on experience with container platforms and deployment patterns, including EKS, ECS, and Docker.
• Strong knowledge of AWS networking concepts, including Route 53, VPC design and management, load balancing, private networking, and secure connectivity.
• Strong knowledge of AWS security and operations services such as IAM, KMS, CloudTrail, CloudWatch, and related monitoring and alerting capabilities.
  
  

Systems Administration

• Expertise in Windows Server administration is a must
• Administer complex Microsoft-based web hosting configuration components, including Windows Server configuration, .NET framework, IIS web sites, and SQL Server database servers.
• Experience with monitoring and alerting tools, such as Prometheus, Grafana, and PagerDuty.
• Experience partnering directly with software engineers to improve application operability, deployment quality, and production support practices.
• Experience modernizing legacy applications, improving deployment processes, or strengthening observability and reliability engineering practices.
  
  

Soft Skills

• Strong written and verbal communication skills directed to technical and non-technical team members
• Willingness to take ownership of problems and seek solutions
• Ability to apply creative problem-solving and manage through ambiguity
• Ability to work under remote supervision and with a minimum of direct oversight.
  
  

Growth Skills

The candidate should have a strong work ethic, be a self-starter with a desire to grow, and consistently seek better ways to accomplish tasks.

Qualification

• Bachelor’s degree in Computer Science, Engineering, or a related field.
• Proven experience as a DevOps Engineer with a focus on AWS.
  
  

This role requires overlap with multiple time zones for planning meetings, status updates etc. on a regular basis. The duration of these overlaps can change depending on the type of meeting. Upland India has the flexibility to manage your working hours accordingly to help in your work-life balance. You can find out more about this during your interview conversation.

Upland Software is an Equal Employment Opportunity Employer. All qualified applicants will receive consideration for employment without regard to race, color, religion, sex, sexual orientation, gender identity, national origin, disability, veteran status or other legally protected status.

About PSA

Upland PSA focuses on planning, execution and financial management of projects. This includes project related business functions such as Timesheet & Leave Request Management, Expense Entry & Approvals, Project Planning & Scheduling, Resource Allocation, and Invoicing.

About Upland

Upland Software (Nasdaq: UPLD) is a leader in AI-powered knowledge and content management software. Our solutions help enterprises unlock critical knowledge, automate content workflows, and drive measurable ROI—enhancing customer and employee experiences while supporting regulatory compliance. More than 1,100 enterprise customers rely on Upland to solve complex challenges and provide a trusted path for AI adoption.

Upland India is a fully owned subsidiary of Upland Software and headquartered in Bangalore. We are a remote-first company. Interviews and on-boarding are conducted virtually.