via Rippling
$70K - 120K a year
Provide technical support and troubleshooting for macOS and Windows environments, focusing on endpoint management and deployment issues.
Must have 3+ years of system administration experience in macOS and Windows, with strong troubleshooting skills and experience with endpoint management tools.
Job Description: Before you apply, please note: This is a full-time role open to remote or hybrid candidates in eligible U.S. states (AR, AZ, CO, CT, FL, GA, ID, IL, IN, KY, MD, MI, MN, MO, NC, NH, OK, OR, TN, TX, UT, VA, WA, WI). No visa sponsorship is available for this position. PDQ is seeking an experienced Systems Administrator who knows Windows and macOS in the real world: troubleshooting, packaging, logs, MDM, and the messy edge cases that show up in production. You’ll join the Solutions team supporting PDQ Connect, our cloud-based, agent-driven endpoint management platform, as we expand macOS capabilities. You’ll also support SimpleMDM, our Apple MDM product for macOS and iOS device management. This role provides technical support for other sysadmins and IT departments. You will: Own customer issues Debug deployments and inventory/scanning problems Reproduce and escalate product bugs with excellent technical detail Improve docs and knowledge articles Provide feedback to Product and Engineering based on customer reality Support is primarily email-based, with some live chat. From time to time we may provide outbound phone & remote support. While this is not a Sales role, you may be the first contact that trial users have with PDQ, so we will be looking for sysadmins who know how to treat a customer right. You will test new features, provide product feedback, reproduce bugs, and support real-world IT environments with all their quirks and inconsistencies. You will be solving hard problems with other people like you: system administrators with real-world experience. Most of our support is conducted via email, with some live meetings via chat or phone. What you'll be doing: Ticket ownership and technical investigation from start to finish Troubleshoot macOS endpoint issues across diverse environments (SMB, enterprise, education, MSP, government) Diagnose scanning/inventory failures, deployment failures, remote access issues, connectivity/credential problems, and environmental constraints Primary focus: PDQ Connect (macOS): PDQ Connect Agent (macOS) PDQ Connect/ISL Remote Desktop apps (agent and viewer) (macOS) PDQ package library and user-created custom packages (macOS) Secondary product focus: SimpleMDM Write and maintain internal docs and customer-facing help center articles. Capture and prioritize customer feedback and feature requests Investigate faults in PDQ Connect’s scanning/inventory capabilities, as well as its application and command deployment. Troubleshoot connectivity issues, credential problems, and environmental issues across customer networks. Collaborate with Engineering, Product, and Strategy on quality and usability improvements We're looking for people who have: Must Have: 3+ years system administration in macOS and Windows environments Strong macOS troubleshooting skills, including command line troubleshooting and reading/interpreting macOS and application logs Experience with Apple MDM (e.g., SimpleMDM, Jamf, Mosyle, Iru/Kandji, Intune). Experience with Windows OS and application deployment, patch management, and troubleshooting Experience with endpoint management tools like PDQ Deploy, PDQ Connect, Intune, SCCM, Kaseya, or similar Proven ability to configure, troubleshoot, and support software deployments in messy end-user environments. Working understanding of endpoint and platform security best practices Exposure to vulnerability or remediation tools (Defender, Nessus, Tenable, etc.) Nice to Have: Experience with scripting, e.g. bash, zsh, AppleScript, PowerShell (Windows), Python Experience with management of Apple operating systems beyond macOS Experience with cloud-based identity providers (IdPs) such as Okta, Entra ID, Google Workspace, as well as web app auth protocols (SSO, OIDC) Basic REST API troubleshooting (using curl, Postman, etc.) Tools we use: Zendesk Microsoft 365 Slack Notion Linear PDQ Perks & Benefits: PDQ offers all of the great perks and benefits you'd expect from working at a very cool tech company, and even some you might not expect, including: 4-Day Work Week Equity Managers who champion professional development 100% Premium Coverage for medical, dental and vision for you and your dependents 100% Premium Coverage for Short Term Disability, Long Term Disability, Life, and AD&D Insurance Company Match of the first 6% of your employee deferrals Flexible Paid Time Off Policy that treats you like the adult that you are Health Savings Account (HSA) and wellness incentives Quarterly Company Values Award (team member nominated) Interview Process Homework Assignment: After applying, you’ll receive a short technical exercise based on PDQ Connect. It’s designed to take under 45 minutes and evaluate your troubleshooting and technical clarity. Preliminary Interview: If your assignment passes, you’ll meet with us for a brief interview covering HR eligibility and foundational knowledge. Cultural & Technical Interviews: Two back-to-back interviews: one assessing culture, values, and team alignment, and one deep technical discussion led by Solutions Engineers. PDQ is proud to be an equal opportunity workplace and do not discriminate on the basis of sex, race, color, age, pregnancy, sexual orientation, gender identity or expression, religion, national origin, ancestry, citizenship, marital status, military or veteran status, genetic information, disability status, or any other characteristic protected by federal, provincial, state, or local law. If you would like to request reasonable accommodation for a medical condition or disability during any part of the application process, please contact hr@pdq.com. The majority of PDQ's full-time roles do not qualify for sponsorship of employment visas such as the H-1B visa. This applies to scenarios where a candidate might possess temporary work authorization during their schooling or after graduation (e.g., CPT, OPT), but would require H-1B visa sponsorship within a few years of employment to retain eligibility for employment.
This job posting was last updated on 1/9/2026