IT Operations Engineer II (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 IT Operations Engineer II to oversee and optimize our IT environment.  As an IT Operations Engineer II, you will be a key driver in optimizing our entire IT ecosystem.  With a high degree of ownership, you will not only administer our core technologies but also lead projects, improve processes, and become a subject matter expert in our technology stack. You will be responsible for owning independent IT projects from technical design through to launch, ensuring our IT systems are scalable, secure, and efficient.

This position is ideal for a proactive problem-solver who can balance independent work with collaborative guidance and effectively mentor junior team members.

• →Administer and manage our IT applications (e.g., Okta, Google Workspace, Slack, Zoom, Jira, Notion) to ensure secure configurations and efficient user access.
• →Design and implement integrations, workflows, and automations to streamline processes and improve efficiency.
• →Utilize Python, or no code solutions to automate repetitive tasks.
• →Utilize Terraform to administer Openly’s IT Infrastructure.
• →Collaborate with cross-functional teams to identify opportunities for automation and process improvement.
• →Configure Jira projects, custom fields, permissions, and workflows to align with evolving business requirements.
• →Maintain access controls, enforce security policies, and ensure data integrity within our technology stack.
• →Collaborate with IT leadership to define project requirements, scope, timelines, and success metrics.
• →Lead and coordinate IT projects, leveraging project management methodologies and tools.
• →Mentor junior IT team members, sharing best practices and fostering a culture of continuous learning.
• →Document and maintain clear, comprehensive guidelines and procedures of our environment.
• →Participate in IT support escalations, addressing complex end-user issues and providing advanced troubleshooting.
• →Proactively identify potential issues, implement monitoring solutions, and coordinate preventive actions.
• →Maintain effective communication with stakeholders regarding incident status, impact, and resolution progress.
• →Monitor application performance, troubleshoot issues, and implement enhancements to maintain high availability and optimal user experience.

• Education: A Bachelor's degree in Information Technology, Computer Science, or a related field, or relevant certifications.
• Experience: 4-6 years of experience in IT Engineering, Systems Administration, DevOps, or a related role.

• Advanced proficiency with Okta, Google Workspace, Jira, and other SaaS applications.
• Proficient in Python or similar languages (e.g., Bash, Javascript).
• Experience with Terraform or other infrastructure-as-code frameworks.
• Experience with version control systems (Github, Git, etc.)
• Experience with public cloud infrastructure (e.g. GCP, AWS)
• Ability to build applications and tools that provide and/or use APIs
• Ability to troubleshoot complex technical issues across a variety of systems and platforms.

• Strategic Thinking: Oftentimes thinks about team practices and processes and discusses improvements with the team.
• Effective Communication: Communicates effectively, clearly, concisely in written and verbal form. Does so both with the team and others in the company, taking the audience into account. Actively listens to others and ensures they are understood. Pays attention to nonverbal communication.
• Innovation: Identifies opportunities for internal process improvement. Communicates and implements innovative solutions in collaboration with IT leadership. Participates in the evaluation and integration of new IT tools and technologies.
• Dealing with Ambiguity: Handles and communicates to leadership any risk, change, and uncertainty within their personal scope of work effectively.
• Architecture: Provides recommendations on systems designed for future scaling. Collaborates in architectural discussions with IT Leadership. Plans for potential 2nd order problems. Collaborates in monitoring work on their team based on the organization's observability philosophy.
• Mentorship: Mentors their teammates in an open, respectful, flexible, empathetic manner. Seeks out mentoring opportunities specifically to create team redundancy and backfill ability.

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