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

Job Description

Openly is rebuilding insurance from the ground up, re-envisioning the customer experience with a focus on premium insurance made simple. The company values integrity, empathy, teamwork, curiosity, and urgency.

Job Location

Remote (US-based candidates only: Citizens, Green Card Holders, or authorized to work in the U.S.)

Job Description

Openly is seeking a proactive Staff IT Engineer to lead technical enablement for the company's AI adoption program. This role sits at the intersection of IT, security, infrastructure, and platform engineering. The successful candidate will build practical automations, integrate AI tools with internal systems, and transform high-value business problems into reliable internal solutions.

Machine Learning & Artificial Intelligence

The role requires a hands-on, product-minded individual capable of moving from rapid prototyping to supportable, scalable internal solutions.

Key Responsibilities

• AI Solution Development: Build and deploy AI-enabled tools, workflows, and internal automations to improve productivity.
• Integration and Enablement: Connect AI agents with enterprise systems (e.g., Okta, Google Workspace, Notion, Jira) to ensure reliable interoperability.
• MCP and Platform Ownership: Build and maintain Model Context Protocol (MCP) connections, including configuration, reliability monitoring, and lifecycle management standards.
• Process Automation: Identify manual workflows and design durable automation solutions using Python, Go, or no-code tools.
• Security and Governance: Partner with Security to implement safe patterns for authentication, authorization, token handling, and data protection.
• Infrastructure Management: Use Terraform, cloud infrastructure, and version-controlled delivery practices to manage supporting systems.
• Documentation and Training: Create clear documentation and technical guidance to facilitate responsible AI adoption.
• Cross-functional Collaboration: Work with IT, Security, Engineering, and business teams to prioritize opportunities and refine solutions.

Required Skills And Qualifications

Education & Experience

• Bachelor's degree in IT, Computer Science, Engineering, or a related field (or equivalent practical experience).
• 8+ years of experience in IT engineering, systems engineering, platform engineering, automation, or DevOps.

Technical Acumen

• Strong experience designing internal tools and automations from idea through production.
• Deep understanding of AI-enabled workflows, prompt-driven systems, agent patterns, and modern AI business applications.
• Proficiency in building API-driven services and automations using Python, JavaScript, or Bash.
• Experience with Infrastructure-as-Code (Terraform) and modern software delivery practices (GitHub/Git).
• Strong knowledge of cloud infrastructure (GCP or AWS).
• Experience with identity/access patterns (OAuth2, OIDC, SAML).
• Ability to design context-aware workflows and troubleshoot complex SaaS/integration issues.

Core Competencies

• Product Thinking: Identifies high-value problems and focuses on meaningful business impact.
• Strategic Architecture: Designs scalable, secure, and maintainable systems.
• Communication: Explains technical concepts clearly and facilitates collaboration.
• Mentorship: Supports team growth and raises technical standards.

Preferred Attributes

• Experience deploying AI tools like Claude or Copilot in an enterprise setting.
• Familiarity with retrieval, knowledge integration, and multi-step agent orchestration.
• Interest in AI governance and security frameworks.

Compensation & Benefits

Salary Range

• Budgeted Range: $168,000 - $200,000 USD
• Full Salary Range: $168,000 - $252,000 USD
• Note: Actual compensation is determined based on experience, skills, and qualifications.

Benefits & Perks

• Remote-First Culture: Dedicated support for remote work.
• Compensation: Competitive Salary & Equity.
• Medical: Comprehensive Medical, Dental, and Vision plans.
• Parental Leave: Up to 8 weeks (320 hours) paid; additional STD options for birthing parents.
• 401(k): Company contributes 3% of gross income.
• Home Stipend: $1,500 one-time allowance for home office setup.
• Professional Development: $2,000 annual fund for PD activities.
• Wellness: $50/month "Be Well" allowance.
• Other: Paid volunteer hours, referral rewards, and performance-based cash incentives where applicable.

Equal Opportunity Employer

Openly is committed to equal employment opportunity and non-discrimination. Openly is an E-Verify Employer.