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. 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.
Requirements
- Bachelor's degree in Information Technology, Computer Science, Engineering, or a related field, or equivalent practical 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 cross-functional 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.
Benefits
- Competitive Salary & Equity
- Comprehensive Medical, Dental, and Vision Plan Offerings
- Life and disability coverage including voluntary options
- Parental Leave - up to 8 weeks (320 hours) of paid parental leave based on meeting eligibility requirements
- 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 workplace
- Annual Professional Development Fund: Each employee has $2,000 in professional development (PD) funds to spend on activities or resources annually.
- Be Well Program - Employees receive $50 per month to use towards your overall well-being
- Paid Volunteer Service Hours
- Referral Program and Reward
