[Remote] IT Staff Engineer - AI Enablement & Automation (Remote, US)

Note: The job is a remote job and is open to candidates in USA. Openly is a company focused on transforming the insurance industry through innovative technology and data-driven solutions. They are seeking a proactive Staff IT Engineer to lead technical enablement for their AI adoption program, which includes building AI-enabled tools, integrating AI systems, and automating workflows to enhance productivity across the organization.

Responsibilities

• Build and deploy AI-enabled tools, workflows, and internal automations that improve productivity and reduce repetitive work across the company
• Connect AI agents, tools, and automations with enterprise systems such as Okta, Google Workspace, Slack, Notion, Jira, and other applications, ensuring reliable interoperability
• Build, maintain, and improve MCP connections and supporting infrastructure, including standards for configuration, reliability, monitoring, and lifecycle management
• Identify manual or fragmented workflows and design durable automation solutions using Python, Go, or no-code tools
• Partner in weekly AI enablement sessions and help turn identified use cases into repeatable, supportable workflows, or tools
• Work closely with Security to implement safe patterns for authentication, authorization, token handling, data protection, and production readiness for AI-enabled workflows
• Use Terraform, cloud infrastructure, and version-controlled delivery practices to manage the systems that support internal AI enablement
• Create clear documentation, reusable patterns, and technical guidance that help teams adopt AI responsibly and effectively
• Partner with IT, Security, Engineering, and business teams to prioritize opportunities, collect feedback, and continuously improve solutions
• Balance quick wins with long-term maintainability, using feedback and operational data to improve quality, adoption, and scale

Skills

• Bachelor's degree in Information Technology, Computer Science, Engineering, or a related field, or equivalent practical experience
• 8+ years of experience in IT engineering, systems engineering, platform engineering, automation, DevOps, or a closely related role
• Strong experience designing and delivering internal tools, automations, or platform capabilities from idea through production
• Strong understanding of AI-enabled workflows, prompt-driven systems, agent patterns, and practical business applications of modern AI tools
• Experience integrating enterprise systems, knowledge sources, and APIs into useful internal workflows or automations
• Experience building and maintaining API-driven services, scripts, and automations using Python, JavaScript, Bash, or similar languages
• Experience with Terraform or similar infrastructure-as-code frameworks
• Experience with GitHub, Git, and modern software delivery practices
• Strong knowledge of cloud infrastructure such as GCP or AWS
• Familiarity with identity and access patterns such as OAuth2, OIDC, SAML, or equivalent enterprise authentication mechanisms
• Ability to design context-aware workflows that maintain continuity across tools and systems, including thoughtful use of MCP and related integration patterns
• Ability to troubleshoot complex issues across SaaS systems, integrations, automation layers, and cloud infrastructure
• Identifies high-value problems, evaluates solution options carefully, and focuses effort where AI and automation can create meaningful business impact
• Connects immediate technical work to broader architectural goals and organizational priorities
• Explains technical concepts clearly, facilitates crossfunctional collaboration, and creates documentation that others can use
• Finds opportunities to simplify processes, reduce SaaS dependency, and improve employee productivity through better tooling and automation
• Operates effectively in fast-moving, uncertain environments and can define structure where little exists
• Designs systems and workflows that are scalable, secure, and maintainable over time
• Shares best practices openly, supports the growth of others, and raises the technical standard of the team
• Experience supporting enterprise rollout and enablement of AI tools such as Claude, Copilot, or similar platforms
• Experience with retrieval, knowledge integration, or context management patterns for AI-enabled workflows
• Familiarity with multi-step agent workflows and orchestration patterns
• Interest in AI governance, security, and responsible-use frameworks
• Ability to deliver fast prototypes without losing sight of reliability, supportability, and enterprise standards

Benefits

• Remote-First Culture - We supported #remotelife long before it was a given. We'll keep promoting it.
• Competitive Salary & Equity
• Comprehensive Medical, Dental, and Vision Plan Offerings
• Life and disability coverage including voluntary options
• Parental Leave - up to 8 weeks (320 hours) of paid parental leave based on meeting eligibility requirements (Birthing parents may be eligible for additional leave through STD)
• 401K Company Contribution - Openly contributes 3% of the employee's gross income, even if the employee does not contribute.
• Work-from-home stipend - We provide a $1,500 allowance to spend on setting up your home workplace
• Annual Professional Development Fund: Each employee has $2,000 in professional development (PD) funds to spend on activities or resources annually. We want each Openly employee to achieve personal and professional success and to feel supported, confident, and informed about improving their efficiency and productivity.
• Be Well Program - Employees receive $50 per month to use towards your overall well-being
• Paid Volunteer Service Hours
• Referral Program and Reward
• Depending on position, Employees generally are eligible for cash incentive compensation, including commissions for sales eligible roles. In all cases, eligibility for compensation and benefits is subject to applicable plan and policy terms in effect from time to time.

Company Overview