Senior IT Systems Administrator

Our Senior IT Systems Administrator is the first line of IT support for our UpKeep employees and also owns the core systems, tools, and infrastructure that keep our teams productive and secure. This is a critical, in-office role based in our Los Angeles HQ, focused on delivering exceptional technical support while building scalable, secure IT operations that support our growing hybrid workforce.

This person will be hands-on in supporting our employees day to day, while also setting the foundation for systems, vendors, and processes that scale. Ideal candidates have a passion for helping others, strong process discipline, excellent communication, and the ability to thrive in a fast-paced, changing environment.

• Owns HQ infrastructure including configuration, maintenance, security, and ensuring uptime for UpKeep personnel based in the office
• First point of contact to manage company wide help desk tickets, to ensure all tickets are tracked to resolution in accordance with UpKeeps service level agreements. 
• Provide advanced technical support, professional communication, and escalation management across hardware, software, and network issues.. 
• Manage and administer office network infrastructure (Wi-Fi, routers, conference room AV systems, etc.) to ensure reliability and uptime.
• Provide on-call support for critical incidents and lead resolution efforts in partnership with system administrators and other stakeholders.
• Leads escalations and proper handoffs of incidents to teams across the organization when further assistance for resolution is required.
• Utilizes tools and resources to stay up to date on technical knowledge in a multi-platform, fast-paced, and changing environment. 
• Support new hire onboarding and offboarding, including laptop provisioning, account setup, and orientation on UpKeep tools and IT processes.
• Own IT asset lifecycle management (procurement, inventory, deployment, recovery).
• Administer and manage core tools including Google Workspace, Zoom, Slack, MDM solutions (e.g., Kandji), and other SaaS platforms.
• Monitor and administer software licenses using Software inventory system. 
• Troubleshoot and resolve issues across hardware, operating systems, cloud applications, mobile devices, printers, phones, and connectivity.

Serve as subject matter expert on video/web conferencing tools and lead AV support for company events or high-priority meetings.

• Identify and implement process improvements to strengthen IT operations, improve employee experience, and support scaling.
• Create and maintain IT documentation and knowledge base articles for both internal use and employee self-service.

• 5 years of progressive IT experience, ideally in a fast-paced, hybrid or startup environment.
• High level of proficiency in macOS environments
• Hands-on experience with MDM solutions (e.g., Kandji), and Google Workspace.
• Strong experience supporting cloud-based SaaS tools, AV systems, mobile devices, and remote/hybrid employee workflows.
• Familiarity with ticketing systems, monitoring tools, and IT asset management platforms.
• Bonus: Experience with VMware/Hyper-V, scripting/automation, or supporting SOC2-compliant environments.

• 5+ years of experience in an enterprise helpdesk, IT support, or IT management capacity.
• Bachelor’s Degree in Computer Science, Information Technology, or related field (or equivalent hands-on experience).
• Strong understanding of modern IT practices, cloud systems, network troubleshooting, and endpoint management.

• Receptive to change – is flexible. Seeks and adopts improved approaches and processes.
• Initiates action – is results oriented, takes responsibility for actions and outcomes. Meets commitments and strives for high performance.
• Manages the workload - makes timely decisions, prioritizes effectively, solves problems, monitors results and takes remedial action where necessary.
• Technically proficient – able to apply the technical knowledge and skills required in the job role and responsibilities in order to achieve the expected outputs. 
• Takes responsibility for own learning - knows personal strengths, recognizes development needs, and takes action to improve. Is open to feedback and always seeks to learn. 
• Communicates ideas – respectfully exchange information and proposes a way forward. Listen to views of colleagues and take in diverse perspectives. 
• Works collaboratively – shares knowledge and information, fosters teamwork and contributes to a positive work environment where people want to come to work.  
• Display ethical character and competence - acts with integrity and intent, is accountable for own actions, behaves according to the company values. 
• Act as a good citizen of UpKeep.  

This role will receive a competitive base salary + annual bonus + benefits + equity. A variety of factors are considered when determining someone’s compensation–including a candidate’s professional background, experience, and location. Final offer amounts may vary from the amounts listed below.

The pay range for this role is $110,000 - $125,000 USD per year.