IT Staff Engineer - AI Enablement & Automation

About Openly

Openly is rebuilding insurance from the ground up, re-envisioning and enhancing every aspect of the customer experience. The company is transforming the insurance industry by combining cutting-edge technology, data science, and a customer-first approach. Openly is on a mission to deliver premium insurance made simple—providing consumers with more complete coverage at competitive prices.

The Role: IT Staff Engineer - AI Enablement & Automation

We are seeking an experienced IT Staff Engineer specializing in AI Enablement and Automation to join our rapidly growing technology team. This is a pivotal role for a senior engineer who will lead technical initiatives around artificial intelligence integration, process automation, and system optimization across Openly's infrastructure and operations.

As an IT Staff Engineer, you will work at the intersection of enterprise technology and cutting-edge AI capabilities. You'll be responsible for designing, implementing, and scaling automation solutions that enhance operational efficiency, reduce manual processes, and enable the organization to leverage AI effectively across departments. This role requires deep technical expertise, strategic thinking, and the ability to collaborate with cross-functional teams including product, engineering, data science, and business operations.

Key Responsibilities

• AI Strategy & Implementation: Lead the evaluation, adoption, and integration of AI and machine learning tools into Openly's IT infrastructure and business processes. Develop best practices for responsible AI deployment.
• Automation Architecture: Design and implement enterprise-wide automation solutions for IT operations, infrastructure management, and business workflows. Optimize system performance through intelligent automation.
• Technical Leadership: Provide technical guidance and mentorship to engineering teams. Lead design reviews, establish coding standards, and drive technical excellence across automation initiatives.
• Infrastructure & DevOps: Oversee IT infrastructure modernization, cloud optimization, and deployment pipelines. Implement automation tools and frameworks for infrastructure-as-code and continuous integration/continuous deployment (CI/CD).
• Cross-Functional Collaboration: Partner with product, data science, and business teams to identify automation opportunities. Translate business requirements into technical solutions that drive measurable impact.
• Security & Compliance: Ensure all AI and automation implementations meet enterprise security, privacy, and regulatory requirements. Develop governance frameworks for AI systems.
• Performance Optimization: Identify bottlenecks in existing systems and processes. Implement AI-driven and automation-based solutions to improve efficiency, reduce costs, and enhance user experience.

Required Qualifications

• 10+ years of experience in IT infrastructure, systems engineering, or software engineering roles, with at least 5 years at a staff or principal level
• Deep expertise in enterprise automation frameworks and tools (e.g., Ansible, Terraform, Python, PowerShell)
• Demonstrated experience with AI/ML technologies, including large language models, prompt engineering, and AI application development
• Strong background in cloud platforms (AWS, Google Cloud, or Azure) and modern DevOps practices
• Proficiency in infrastructure-as-code, containerization (Docker, Kubernetes), and CI/CD pipeline management
• Experience designing and implementing scalable, highly available systems in production environments
• Excellent problem-solving skills and ability to think strategically about technology roadmaps
• Strong communication skills with the ability to explain complex technical concepts to non-technical stakeholders

Preferred Qualifications

• Experience in the insurance or fintech industries
• Familiarity with enterprise AI governance and responsible AI frameworks
• Background in security architecture and compliance (SOC 2, ISO 27001)
• Experience leading engineering teams or managing technical projects
• Published work or contributions to open-source automation or AI projects

Why Join Openly

The Openly Difference: Openly is transforming the insurance industry with three key differentiators. The Price Difference leverages cutting-edge data and technology to provide customizable, competitive prices protecting your most valuable assets. The Policy Difference offers truly customizable coverages meeting individual protection needs for both standard and optional add-on coverage. The Experience Difference focuses on tailored claims handling and highly responsive customer service, making the home insurance experience better.

At Openly, people are central to our mission. We prioritize collaboration, communication, and work-life balance as must-haves, not nice-to-haves. We believe exceptional companies are built by teams that share a commitment to innovation, customer obsession, and mutual support. You'll be part of a team of curious, empathetic professionals spanning technology, data science, product, marketing, sales, service, claims, and finance.

Work Environment

• Location: Remote position based in the United States, offering flexibility and work-life balance
• Culture: Join a rapidly growing team of exceptional talent committed to reshaping insurance
• Impact: Lead strategic initiatives that directly influence Openly's technology roadmap and competitive advantage
• Growth: Opportunities for professional development, mentorship, and career advancement in a scaling organization

If you're a visionary technologist passionate about leveraging AI and automation to transform business processes, and you're excited about reshaping the insurance industry, we want to hear from you. This is your next adventure.

💰 Compensation not publicly listed. Market estimate for similar roles: from $180K, varying by experience and location.