IT Support Specialist II (Remote, US)

Openly has redefined the insurance experience—replacing decades of complexity with clarity. We’re the insurance provider for people who expect more and the partner independent agents have been waiting for.

Building a better future for personal lines insurance requires diverse expertise and thoughtful execution. We bring together dedicated problem-solvers who are excited to challenge the status quo and do meaningful work.

• Technology That Delivers: We leverage cutting-edge data to modernize underwriting and deliver tailored insurance solutions.

• Superior Protection: Highly customizable coverage designed to match the unique needs of modern homeowners.

• A Seamless Experience: Frictionless workflows for independent agents and fast, human-centered care for policyholders.

At Openly, our people are just as important as our product. Collaboration, communication, and work-life balance aren't just nice-to-haves—they are core to who we are. We believe a great company is built on a foundation of shared values, which is why we seek out individuals driven by integrity, empathy, teamwork, curiosity, and a healthy sense of urgency.

We embrace individuality and know that diverse teams build better products. Our commitment to inclusion across race, gender, age, religion, identity, and background drives our culture and our business forward every day.

Job Details:

We're looking for an experienced and proactive IT Support Specialist II (EDT, MST, CST timezones preferred) to join our team. In this mid-level role, you'll be instrumental in managing our IT infrastructure, resolving complex technical issues, and guiding junior team members. You'll take ownership of technical challenges, contribute to the improvement of IT processes, and collaborate with other teams to ensure our IT operations are efficient and effective. This position is ideal for a skilled IT professional who is ready to take on a larger role in technical support and is passionate about process improvement.

Key Responsibilities:

• Provide advanced technical support to end-users, serving as an escalation point for hardware, software, and technology issues that require in-depth troubleshooting and analysis.

• Take ownership of technical challenges, providing guidance to junior team members and collaborating with other IT teams to address and resolve intricate problems.

• Administer and maintain IT infrastructure, including user account management, access control, and other critical systems.

• Identify opportunities to enhance IT support processes and actively implement improvements to increase efficiency and effectiveness.

• Create and maintain comprehensive documentation for IT infrastructure and processes, ensuring knowledge is shared across the team.

• Provide training and guidance to end-users and junior team members on best practices and the use of various hardware and software applications.

• Facilitate the IT onboarding process for new hires by configuring their computers and applications, and serving as their primary point of contact for any initial technical questions.

• Manage IT assets and inventory, from procurement and deployment to tracking and disposal of hardware and software.

• Lead and coordinate small to medium IT projects, leveraging project management methodologies and tools.

• Support and maintain both macOS and Windows environments, staying updated on new technologies and industry trends.

• Effectively communicate technical solutions to both technical and non-technical stakeholders, actively listening to others and ensuring you are understood.

Requirements: 

• Education: Associates degree in Information Technology, Computer Science, or a related field, or relevant certifications.

• Experience: 3-5 years of experience in an IT support role.

• Awareness of scripting languages (Python), no code automation tools, and infrastructure as code technologies (Terraform)

Technical Acumen:

• In-depth understanding of hardware, software, and IT environments.

• Proven experience in advanced troubleshooting and problem resolution.

• Strong understanding of networking concepts.

• Knowledge of administering and maintaining IT infrastructure including Okta and Google Workspace.

• Proficiency in macOS and Windows environments.

• Ability to implement IT best practices and processes.

Core Competencies:

• Customer Service: A strong commitment to providing prompt and effective support to end-users with a patient and empathetic approach.

• Communication Skills: Communicates clearly and concisely with both technical and non-technical stakeholders, actively listening and ensuring you are understood.

• Documentation: Creates and maintains comprehensive documentation for IT infrastructure and processes, sharing knowledge with the team.

• Process Improvement: Proactively identifies opportunities to enhance IT support processes and implements solutions to increase efficiency.

• Proactive Learning: A strong desire to learn and expand your technical knowledge.

• Collaborative Problem-Solving: Acts as a resource for troubleshooting across the organization, working with other IT teams to address complex issues.

Location: 

This is a remote position with candidates in the Central, Mountain, and Eastern timezones preferred, with the ability to flex hours as needed.

Applicants must be currently authorized to work in the United States on a full‑time basis. This position is not eligible for employer visa sponsorship now or in the future.

Great work happens when people feel supported, valued, and empowered. From comprehensive health coverage to remote-work flexibility, our benefits are designed to care for you and your family at every stage of life.

• Remote-First Culture: We supported remote work long before it became standard, and we remain dedicated to a flexible, distributed team.

• Competitive Pay & Equity: Top-tier base salary plus ownership in Openly’s growth.

• Comprehensive Health Coverage: Medical, dental, and vision plans tailored to you and your family.

• Life & Disability Insurance: Full coverage including voluntary supplemental options.

• Parental Leave: Up to 8 weeks (320 hours) of paid parental leave for eligible employees (with additional disability coverage available for birthing parents).

• 401(k) Company Contribution: Openly contributes 3% of your gross income, regardless of whether you make personal contributions.

• Home Office Setup: A $1,500 upfront allowance to build your ideal remote workspace, plus a $75/month internet stipend.

• Professional Development: $2,000 annually to invest in courses, conferences, or resources that help you grow.

• "Be Well" Program: A $50/month stipend dedicated to your personal health and well-being.

• Volunteer Hours & Referral Rewards: Paid time off to give back to your community, plus generous financial rewards for referring great talent.

Note: Select roles may also be eligible for cash incentives or sales commissions. Eligibility for all compensation and benefits is governed by applicable plan terms.

Our Hiring Commitment: We believe interviewing is a two-way street. We’ve designed our hiring process to be transparent, respectful, and human. At every step, you’ll have space to showcase your strengths, ask tough questions, and discover if Openly is the right place for your next chapter.

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.