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OpenlyOP

IT Operations Engineer II (Remote, US)

Openly is a premium home insurance provider that sells exclusively through independent agents, leveraging technology to offer comprehensive and transparent coverage.

Openly

Employee count: 201-500

Salary: 90k-150k USD

United States only

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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 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.

Key Responsibilities

  • 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.

Qualifications

  • 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.

Technical Acumen

  • 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.

Core Competencies

  • 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.

Compensation & Benefits:

Below is the budgeted salary range for this position. Actual compensation for this position will be determined based on the successful candidate's experience and skills. We are committed to providing a compensation package that not only reflects the responsibilities and requirements of the role, but also the unique expertise that the chosen candidate will bring to our team.

Budgeted Salary Range
$96,000—$114,000 USD

The full salary range shows the min to max salary range for this position. Actual compensation will be commensurate with experience and qualifications and determined based on various factors including the candidate's qualifications, skills, and experience.

Full Salary Range
$90,000—$150,000 USD

Benefits & Perks

  • Remote-First Culture - We supported #remotelife long before it was a given. We'll keep promoting it.
  • 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
    (Birthing parents may be eligible for additional leave through STD)
  • 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. We want each Openly employee to achieve personal and professional success and to feel supported, confident, and informed about improving their efficiency and productivity.
  • Be Well Program - Employees receive $50 per month to use towards your overall well-being
  • Paid Volunteer Service Hours
  • Referral Program and Reward

Depending on position, Employees generally are eligible for cash incentive compensation, including commissions for sales eligible roles. In all cases, eligibility for compensation and benefits is subject to applicable plan and policy terms in effect from time to time.

U.S. Citizens, Green Card Holders, and those authorized to work in the U.S. for any employer and currently residing in the US will be considered.

Openly is committed to equal employment opportunity and non-discrimination for all employees and qualified applicants without regard to a person's race, color, sex, gender identity or expression, age, religion, national origin, ancestry, ethnicity, disability, veteran status, genetic information, sexual orientation, marital status, or any characteristic protected under applicable law. Openly is an E-Verify Employer in the United States. Openly will make reasonable accommodations for qualified individuals with known disabilities under applicable law.

We strive to provide an exceptional applicant and candidate journey when you engage with us. In an effort to respond to applicants in a timely manner, we leverage AI to organize applications and resumes based on required and applicable skills and experience. To allow our applicants to drive their initial interview experience with us, we may leverage an AI-supported scheduling tool so you can choose when to meet with our team. While AI assists with efficiency, all hiring decisions are made by our team members. Rest assured, your data is protected according to privacy laws and company policies. Contact our recruitment team with any questions about our AI-assisted hiring process.

About the job

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Posted on

Job type

Full Time

Experience level

Salary

Salary: 90k-150k USD

Education

Bachelor degree
Professional certificate

Experience

4 years minimum

Location requirements

Hiring timezones

United States +/- 0 hours

About Openly

Learn more about Openly and their company culture.

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Openly is a premium homeowners insurance provider that leverages advanced technology and deep industry expertise to offer comprehensive and transparent coverage. Founded in 2017 by Ty Harris and Matt Wielbut, the company was established to address a gap in the market for straightforward, customer-friendly home insurance policies distributed exclusively through independent insurance agents. Openly's innovative approach integrates actuarial science, machine learning, and cutting-edge technology to streamline the insurance process for both agents and consumers. This makes quoting faster, policies clearer, and claims smoother, ultimately enhancing the overall customer experience. The company is dedicated to empowering independent agents by providing them with a superior technology platform and a product that offers robust coverage options tailored to individual homeowner needs.

Headquartered in Boston, Massachusetts, Openly has rapidly expanded its operations and now offers its services in numerous states across the United States, with ongoing plans for further nationwide expansion. The company prides itself on its core values of integrity, empathy, teamwork, curiosity, and urgency, which guide its interactions with customers, agents, and employees. Openly operates as a remote-first company, allowing it to attract top talent from across the country. It has built its entire technology stack in-house, including systems for pricing, underwriting, billing, and policy management, which provides greater flexibility and efficiency compared to traditional carriers relying on off-the-shelf software. This commitment to technological innovation and customer-centric service has positioned Openly as a transformative force in the insurtech landscape, focused on rebuilding insurance from the ground up with a strong emphasis on transparency and simplicity.

Employee benefits

Learn about the employee benefits and perks provided at Openly.

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Paid Volunteer Service Hours

Paid volunteer service hours.

Vision Insurance

Openly offers vision insurance.

Company-sponsored outings

Openly has company paid off sites for teams to meet in person.

Life Insurance

Openly offers basic life insurance and accidental death & dismemberment.

View Openly's employee benefits
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