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

Openly is rebuilding insurance from the ground up. We are re-envisioning and enhancing every aspect of the customer experience. Doing this requires a rapidly growing team of exceptional, curious, empathetic people with a wide range of skill sets, spanning technology, data science, product, marketing, sales, service, claims handling, finance, etc.

We created Openly because we saw an evident gap in the market for premium insurance made simple. Consumers deserve more complete coverage at competitive prices.

• The Price Difference: Using cutting-edge data and technology, we provide you with customizable, competitive prices to protect your most valuable assets.
• The Policy Difference: Coverages are truly customizable to meet your individual protection needs, for both standard coverages and optional add-ons.
• The Experience Difference: From tailored claims handling to highly responsive customer service, we are focused on making the home insurance purchasing process a better overall experience.

At Openly, our people are just as important as our product. For us, collaboration, communication, and work-life balance are more than nice-to-haves— they’re the must-haves that make us who we are. We believe a great company is the result of a shared set of values, so we look for these qualities in every candidate we hire. 

• Integrity
• Empathy
• Teamwork
• Curiosity
• Urgency

We've designed our hiring process with you, the candidate, in mind. At every step, you have the chance to present your strengths and learn more about what makes Openly a great place to work.

We embrace individuality and believe diverse teams are winning teams. Our commitment to inclusion across race, gender, age, religion, identity, and experience drives us forward every day.

We are looking for a proactive Staff IT Engineer to lead technical enablement for Openlyʼs AI adoption program. This role will help accelerate enterprise-wide AI usage by building practical automations, integrating AI tools with internal systems, and turning high-value business problems into reliable internal solutions.

This person will sit at the intersection of IT, security, infrastructure, and platform engineering. The role will own and improve the technical foundations for AI enablement, including tool rollout, integration patterns, MCP connectivity, workflow automation, and the operational standards required to scale adoption safely. The right candidate will be hands-on, product-minded, and able to move from rapid prototype to supportable internal solution.

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

• Education: Bachelorʼs degree in Information Technology, Computer Science, Engineering, or a related field, or equivalent practical experience.
• 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.

• Product thinking: Identifies high-value problems, evaluates solution options carefully, and focuses effort where AI and automation can create meaningful business impact.
• Strategic thinking: Connects immediate technical work to broader architectural goals and organizational priorities.
• Effective communication: Explains technical concepts clearly, facilitates crossfunctional collaboration, and creates documentation that others can use.
• Innovation: Finds opportunities to simplify processes, reduce SaaS dependency, and improve employee productivity through better tooling and automation.
• Dealing with ambiguity: Operates effectively in fast-moving, uncertain environments and can define structure where little exists.
• Architecture: Designs systems and workflows that are scalable, secure, and maintainable over time.
• Mentorship: 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.

• Increase adoption of AI across the company through well-designed tools, integrations, and technical enablement.
• Improve employee productivity by automating repetitive tasks and streamlining cross-system workflows.
• Create reusable technical patterns that allow AI solutions to be delivered more quickly and safely.
• Strengthen the technical foundation of Openlyʼs AI enablement program so it can scale with the business.

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