IT Systems Administrator

Vineskills is the preferred implementation and optimization partner of Filevine, the leading legal tech platform powering law firms nationwide. We deliver managed services, system migrations, and accounting solutions tailored for legal professionals. As a fast-growing team operating at the intersection of technology and law, we are seeking an experienced IT Systems Administrator to maintain our technology infrastructure and lead key security and compliance initiatives.

About the role:

The IT Systems Administrator will own Vineskills' internal tech stack, keep our technology operations running smoothly, and be the go-to resource for our fully remote team, helping everyone get the most out of the tools we use. You'll bring lightning-fast support with a solutions-first mindset, making sure no one stays stuck for long. You’ll proactively find solutions to simplify manual processes and automate using our tech stack. 

You'll also be the guardian of our data standards, ensuring our CRM is clean, connected, and firing on all cylinders with our third-party systems. You'll own all things Filevine, integrations, data flows, and everything in between.

This is a full-time independent contractor role open to candidates based in Latin America (LATAM).

Responsibilities include:

• Serve as the go-to resource for internal teams, handling training, troubleshooting, coaching, and helping everyone get the most out of our tech stack.
• Proactively identify gaps in tool adoption, workflows, and system usage, and drive improvements through process optimization, automation, and smarter use of existing tools (not just adding new ones).
• Design and deliver lightweight training, documentation, and guidance to improve team proficiency and consistency across systems.
• Collaborate with team members and the Filevine implementation team to identify technology needs, improve workflows, support data cleanup and migration, and assist with system configuration.
• Contribute ideas for process improvements, automation, and technology upgrades that keep our stack scalable and efficient.
• Help us build new AI forward systems. For example, we are redesigning how we take notes, use work trackers and sync that data into our CRM so everyone has context. This may involve Granola AI, Google Docs/Sheets, Zapier and APIs.

• Google Workplace and Gpanel
• Slack
• ChatGPT and Claud
• Microsoft Office 365 - Business Apps only
• Filevine CRM (we will train you)
• Zoom and Gong
• 1Password with Device Trust by Kolide
• Loom

• 2-4+ years of experience in IT systems administration covering areas of the Tech Stack above.
• Friendly, camera-on, and genuinely excited about helping people work smarter, you love solving problems and finding simpler ways to get things done.
• Solid understanding of identity and access management (SSO, MFA).
• Strong documentation habits and comfort working in asynchronous, remote environments.

• Competitive contractor rate (LATAM market aligned, commensurate with experience).
• 100% remote work with flexible hours.
• Opportunity to grow into a long-term, expanded role as Vineskills scales.
• Work with a collaborative, ambitious team that values autonomy and ownership.
• Paid time off aligned to local holidays and company norms (including a running tradition of Christmas–New Year break).
• Bonus opportunities 

• Be a part of a friendly, enthusiastic, camera’s-on 100% remote tech-forward team 
• Be a key player in securing and scaling a fast-growing legal-tech company.
• Join a team that trusts you, gives you ownership, and appreciates thoughtful, proactive work.
• Grow your expertise in Filevine, legal-tech infrastructure.
• Help shape how technology enables an entire organization, not just maintain it.
• Video introduction from our CEO, Troy