Openly
Insurance
ITStaffEngineer-AIEnablement&Automation
Neural analysis suggests this role is
optimal for Staff candidates.
“IT Staff Engineer - AI Enablement & Automation at Openly. Skills: AI Enablement, Automation, Integration, Platform Engineering, Infrastructure as Code. Lead technical enablement for Openlyʼs AI adoption program. Accelerate enterprise-wide AI usage by building practical automations”
What You'll Achieve.
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
Industry & Context.
What They're Looking For.
Must Have
8+ years of experience in IT engineering, systems engineering, platform engineering, automation, DevOps, or a closely related role, Experience designing and delivering internal tools, automations, or platform capabilities from idea through production, 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, 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
Nice to Have
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
What You'll Do.
Lead technical enablement for Openlyʼs AI adoption program
Accelerate enterprise-wide AI usage by building practical automations
Integrate AI tools with internal systems
Turn high-value business problems into reliable internal solutions
Own and improve the technical foundations for AI enablement
including tool rollout
and operational standards
Build and deploy AI-enabled tools
and internal automations
and automations with enterprise systems
and improve MCP connections and supporting infrastructure
Identify manual or fragmented workflows and design durable automation solutions
Partner in weekly AI enablement sessions and help turn identified use cases into repeatable
supportable workflows
Work closely with Security to implement safe patterns for authentication
and production readiness for AI-enabled workflows
and version-controlled delivery practices to manage the systems that support internal AI enablement
Create clear documentation
and technical guidance
and business teams to prioritize opportunities
and continuously improve solutions
Balance quick wins with long-term maintainability
using feedback and operational data to improve quality
How You'll Work.
Team & Collaboration
Partner with IT, Security, Engineering, and business teams to prioritize opportunities, collect feedback, and continuously improve solutions; Facilitates crossfunctional collaboration; Shares best practices openly, supports the growth of others, and raises the technical standard of the team
Communication Scope
Effective communication: Explains technical concepts clearly, facilitates crossfunctional collaboration, and creates documentation that others can use.
Full Job Description
Why Openly 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. The Openly Difference 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. Welcome to your next adventure. 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're committed to Diversity, Equity, & Inclusion 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. Job Details We are looking for a proactive Staff IT Engineer to lead technical enablement for Openlyʼs AI adoption program. This role will
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