IT Support Specialist II

About the Opportunity

The organization has redefined the insurance experience—replacing decades of complexity with clarity. It is 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. The team brings together dedicated problem-solvers who are excited to challenge the status quo and do meaningful work.

What Sets Us Apart

• Technology That Delivers: The organization leverages 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.

Our Core Values

At the organization, its people are just as important as its product. Collaboration, communication, and work-life balance aren't just nice-to-haves—they are core to who the organization is. It believes a great company is built on a foundation of shared values, which is why it seeks out individuals driven by integrity, empathy, teamwork, curiosity, and a healthy sense of urgency.

Diversity, Equity, & Inclusion

The organization embraces individuality and knows that diverse teams build better products. Its commitment to inclusion across race, gender, age, religion, identity, and background drives its culture and its business forward every day.

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 understanding.

Requirements

• Education: Associate's 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 understanding.
  • 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 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.

Perks & Benefits

• Remote-First Culture: The organization supported remote work long before it became standard, and it remains dedicated to a flexible, distributed team.
• Competitive Pay & Equity: Top-tier base salary plus ownership in the organization's growth.
• Comprehensive Health Coverage: Medical, dental, and vision plans tailored to individuals and their families.
• 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: The organization contributes 3% of gross income, regardless of whether personal contributions are made.
• Home Office Setup: A $1,500 upfront allowance to build an ideal remote workspace, plus a $75/month internet stipend.
• Professional Development: $2,000 annually to invest in courses, conferences, or resources that help individuals grow.
• "Be Well" Program: A $50/month stipend dedicated to personal health and well-being.
• Volunteer Hours & Referral Rewards: Paid time off to give back to the community, plus generous financial rewards for referring great talent.

Our Hiring Commitment

The organization believes interviewing is a two-way street. Its hiring process is designed to be transparent, respectful, and human. At every step, individuals will have space to showcase their strengths, ask tough questions, and discover if the organization is the right place for their next chapter.