[Hiring] Cloud Operations AI Engineer @Upland Software

Role Description

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.

Qualifications

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

Requirements

• Strong foundation in operating production SaaS systems.
• Solid understanding of AWS and DevOps practices.
• Ability to apply AI effectively to operational engineering challenges.
• Experience with AI-assisted engineering tools such as GitHub Copilot, AWS Bedrock, Claude-based coding tools, or similar assistants.
• Experience automating manual operational work such as health checks, remediation steps, patching processes, reporting, recurring maintenance, and deployment support.
• Strong experience with Infrastructure-as-Code technologies; Terraform is required, and Ansible is a plus.
• Strong production experience with Amazon Web Services in a 24x7 SaaS environment.
• Expertise in Windows Server administration.
• 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.

Benefits

• This role requires overlap with multiple time zones for planning meetings, status updates, etc. on a regular basis.
• Upland India has the flexibility to manage your working hours accordingly to help in your work-life balance.