[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.ResponsibilitiesBuild and deploy AI-enabled tools, workflows, and internal automations that improve productivity and reduce repetitive work across the companyConnect AI agents, tools, and automations with enterprise systems such as Okta, Google Workspace, Slack, Notion, Jira, and other applications, ensuring reliable interoperabilityBuild, maintain, and improve MCP connections and supporting infrastructure, including standards for configuration, reliability, monitoring, and lifecycle managementIdentify manual or fragmented workflows and design durable automation solutions using Python, Go, or no-code toolsPartner in weekly AI enablement sessions and help turn identified use cases into repeatable, supportable workflows, or toolsWork closely with Security to implement safe patterns for authentication, authorization, token handling, data protection, and production readiness for AI-enabled workflowsUse Terraform, cloud infrastructure, and version-controlled delivery practices to manage the systems that support internal AI enablementCreate clear documentation, reusable patterns, and technical guidance that help teams adopt AI responsibly and effectivelyPartner with IT, Security, Engineering, and business teams to prioritize opportunities, collect feedback, and continuously improve solutionsBalance quick wins with long-term maintainability, using feedback and operational data to improve quality, adoption, and scaleSkillsBachelor's degree in Information Technology, Computer Science, Engineering, or a related field, or equivalent practical experience8+ years of experience in IT engineering, systems engineering, platform engineering, automation, DevOps, or a closely related roleStrong experience designing and delivering internal tools, automations, or platform capabilities from idea through productionStrong understanding of AI-enabled workflows, prompt-driven systems, agent patterns, and practical business applications of modern AI toolsExperience integrating enterprise systems, knowledge sources, and APIs into useful internal workflows or automationsExperience building and maintaining API-driven services, scripts, and automations using Python, JavaScript, Bash, or similar languagesExperience with Terraform or similar infrastructure-as-code frameworksExperience with GitHub, Git, and modern software delivery practicesStrong knowledge of cloud infrastructure such as GCP or AWSFamiliarity with identity and access patterns such as OAuth2, OIDC, SAML, or equivalent enterprise authentication mechanismsAbility to design context-aware workflows that maintain continuity across tools and systems, including thoughtful use of MCP and related integration patternsAbility to troubleshoot complex issues across SaaS systems, integrations, automation layers, and cloud infrastructureIdentifies high-value problems, evaluates solution options carefully, and focuses effort where AI and automation can create meaningful business impactConnects immediate technical work to broader architectural goals and organizational prioritiesExplains technical concepts clearly, facilitates crossfunctional collaboration, and creates documentation that others can useFinds opportunities to simplify processes, reduce SaaS dependency, and improve employee productivity through better tooling and automationOperates effectively in fast-moving, uncertain environments and can define structure where little existsDesigns systems and workflows that are scalable, secure, and maintainable over timeShares best practices openly, supports the growth of others, and raises the technical standard of the teamExperience supporting enterprise rollout and enablement of AI tools such as Claude, Copilot, or similar platformsExperience with retrieval, knowledge integration, or context management patterns for AI-enabled workflowsFamiliarity with multi-step agent workflows and orchestration patternsInterest in AI governance, security, and responsible-use frameworksAbility to deliver fast prototypes without losing sight of reliability, supportability, and enterprise standardsBenefitsRemote-First Culture - We supported #remotelife long before it was a given. We'll keep promoting it.Competitive Salary & EquityComprehensive Medical, Dental, and Vision Plan OfferingsLife and disability coverage including voluntary optionsParental 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 workplaceAnnual 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-beingPaid Volunteer Service HoursReferral Program and RewardDepending 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 OverviewOpenly offers premium home insurance exclusively through independent agents in multiple states. It was founded in 2017, and is headquartered in Boston, Massachusetts, USA, with a workforce of 201-500 employees. Its website is https://openly.com.