Pie's mission is to empower small businesses to thrive by making commercial insurance affordable and as easy as pie. We leverage technology to transform how small businesses buy and experience commercial insurance.

Like our small business customers, we are a diverse team of builders, dreamers, and entrepreneurs who are driven by core values and operating principles that guide every decision we make.

We are looking for an IT Support Analyst to join our team.  This role is responsible for providing best in class Information Technology helpdesk support that will ensure Pie team members have the tools and technologies they need to set them up for success from onboarding and throughout the team member’s life cycle. This individual will be responsible for hardware/software/VOIP troubleshooting, identity and access management via Okta and EntraID, copier/printer support, and asset management. The candidate should have extensive experience troubleshooting LAN/WAN/VPN and strong understanding of networking protocols. Atlassian administration experience (Jira/Confluence) is preferred as well as familiarity working with mobile device management tools (Intune/Endpoint Management and Addigy). Must be proficient in both PCs and Macs. 

Security and Cloud Service Operations:

• Ensure internal security best practices for team member computers, Pie data, Pie network access and backup systems.
• We are a 100% cloud/SaaS organization. Administer and integrate cloud services: Okta, Google Workspace, Office 365, Zoom, Slack.
• Create and update technology documentation for internal IT teams and for Pie team members.
• Administration of Atlassian Cloud (Jira/Confluence/Service Desk).

Work to Onboard New Team Members:

• Ensuring all new Pie-oneers have their computer and applications set up and ready for use when they arrive on their first day.
•  Work with functional teams and business leaders to ensure all standard profiles for new hire access are kept up to date.
• Keep the IT team scaling efficiently by automating recurring tasks such as onboarding, offboarding and access workflows
• Provision/Deprovision accounts/computers. Setup and document all required access for new employees.

Managing Technical Support for Team Members at all Levels:

• Managing end-point protection, telephony, computer hardware, and computer software.
• Provide IT assistance via remote support channels to all Pie employees for a multitude of operational tasks e.g. password resets, access requests, application support.
• Provide IT support for remote team members, including configuring, shipping, and receiving employee devices.
• Direct interaction with people is central to this role.

• 2+ years of IT Support and Systems Administration experience.
• 2+ years experience with onboarding and employee management experience - Strong proficiency in employee on-boarding, and how to efficiently set-up new employees for success on their first day is required.
• Knowledge of setting up and administering cloud based infrastructure systems is required. Working with Okta, Google Workspace, Office 365, Zoom, Slack, cloud anti-virus, such as SentinelOne is highly preferred.
• Knowledge with system administration of a cloud phone system required.
• Knowledge of working with remote monitoring systems (RMM) required. Connectwise Control highly preferred.
• Must have strong interpersonal and communication skills. Strong problem-solving skills, with ability to quickly resolve issues as they arise.
• Working with device management software programs, specifically Addigy or Intune/Endpoint Management  is  highly preferred.
• Strong understanding of using automation to scale IT infrastructure for a start-up or a small business is a plus.

The use of AI in Application Review: To support a fair, efficient, and consistent hiring process, we use AI-powered tools to assist in the initial screening of applications. These tools help us identify qualifications and prior work experiences that align with the requirements of the role. We may also use AI assistant video tools during interviews to support note-taking and candidate evaluation. All AI-powered outputs are still subject to human oversight and decision-making at multiple stages of the process. By submitting your application, you acknowledge and consent to Pie utilizing these AI technologies to assist in our evaluation process.

Base Compensation Range

$30.25—$36 USD

Compensation & Benefits 

• Competitive cash compensation
• A piece of the pie (in the form of equity)
• Comprehensive health plans
• Generous PTO
• Future focused 401k match
• Generous parental and caregiver leave
• Our core values are more than just a poster on the wall; they’re tangibly reflected in our work 

Our goal is to make all aspects of working with us as easy as pie. That includes our offer process. When we’ve identified a talented individual who we’d like to be a Pie-oneer , we work hard to present an equitable and fair offer. We look at the candidate’s knowledge, skills, and experience, along with their compensation expectations and align that with our company equity processes to determine our offer ranges. 

Each year Pie reviews company performance and may grant discretionary bonuses to eligible team members.

Unless otherwise specified, this role is remote. Remote team members must live and work in the United States (territories excluded) and have access to reliable, high-speed internet.

Pie Insurance is an equal opportunity employer. We do not discriminate on the basis of race, color, religion, sex, sexual orientation, gender identity, marital status, age, disability, national or ethnic origin, military service status, citizenship, or other protected characteristic.

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Safety First: Pie Insurance is committed to your security during the recruitment process. We will never ask you for credit card information or ask you to purchase any equipment during our interview or onboarding process.

Pie Named to 2025 America's Best Startup Employers

Pie Insurance 2025 State of Workplace Safety Report

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