Full-Time

IT Systems Administrator

Multiple Teams

Posted on 9/10/2025

Side

Side

201-500 employees

Agent-owned real estate platform with tech support

Compensation Overview

$110k - $130k/yr

San Francisco, CA, USA

In Person

Requires being on-site 4–5 days per week.

Category
IT & Security (1)
Required Skills
Datadog
Bash
Python
Atlassian
Requirements
  • 3–5 years of hands-on IT systems administration and end-user support experience in a modern SaaS environment
  • Demonstrated ability to manage IT support tickets and resolve issues efficiently with a customer-service mindset
  • Experience with enterprise tools like Okta, Google Workspace, Jamf, Atlassian, 1Password, and Slack
  • Familiarity with MDM, SSO, conditional access policies, and identity governance
  • Understanding of networking concepts and best practices
  • Basic scripting skills (Python, Bash, etc.) a plus
  • Strong attention to detail with a security-first mindset
  • Proven experience supporting a hybrid workforce in a fast-paced environment
  • Excellent communication skills and the ability to work cross-departmentally
  • Strong documentation and process-oriented thinking
Responsibilities
  • Serve as the primary point of contact for IT support, managing the helpdesk queue, resolving tickets, and escalating when necessary
  • Troubleshoot and resolve technical issues across systems, applications, devices, and networks
  • Administer, maintain, and support systems across our SaaS and endpoint ecosystem (Okta, Google Workspace, Jamf, Slack, Zoom, Atlassian, etc.)
  • Monitor system health and performance, applying patches, updates, and policy changes as needed
  • Manage user provisioning/deprovisioning and access workflows in coordination with HR and Security teams
  • Enforce device compliance and security policies through MDM platforms (Jamf)
  • Maintain office network infrastructure, including configuration, firmware updates, and security for UniFi equipment
  • Assist with security monitoring and remediation using tools such as Datadog and SentinelOne
  • Document IT processes, create knowledge base articles, and maintain accurate system records
  • Partner with the IT Director on strategic improvements to systems and processes
Desired Qualifications
  • Basic scripting skills (Python, Bash, etc.) a plus

Side Inc. partners with top-performing real estate agents, giving them ownership of their own businesses plus time-saving technology and premier support. It uses a proprietary app to automate transaction management and provides back-office, compliance, and recruiting resources so agents can focus on clients. Unlike traditional brokerages, it targets extraordinary agents and enables them to launch independent firms without a brokerage using customized plans and vetted tools. Its goal is to help high-performing agents run scalable, compliant businesses while expanding its national footprint.

Company Size

201-500

Company Stage

Late Stage VC

Total Funding

$263.5M

Headquarters

San Francisco, California

Founded

2017

Simplify Jobs

Simplify's Take

What believers are saying

  • Side launched over 500 companies since 2017 for top agents.
  • Recent partnerships include Distinct Concierge and SIMPLE Real Estate.
  • AI tools in Side App enhance document validation and offer extraction.

What critics are saying

  • Redfin's agent-owned model competes directly within 12-24 months.
  • NAR settlements shrink agent economics starting August 2024.
  • eXp Realty undercuts with higher splits in 6-18 months.

What makes Side unique

  • Side exclusively partners with top-performing agents, not average ones.
  • Side enables full agent ownership without operating a brokerage.
  • Side's proprietary app automates transactions, saving 4-6 hours per deal.

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Benefits

Competitive compensation packages

Comprehensive medical, dental, and vision

Wellness perks

Flexible work hours and time off

Professional development funds

Transparent culture

Pet friendly workplace

Pre-tax commuter & FSA benefits

Growth & Insights and Company News

Headcount

6 month growth

1%

1 year growth

2%

2 year growth

3%
Cision
Nov 30th, 2022
Top-Producing Realtor® Don Ashley Partners With Side In The Wellmakers

The WellMakers Group, Founded by Don Ashley I aim to double down on our service-first strategy as we continue to help our clients reach their goals. Don Ashley today announced The Wellmakers Group and its partnership with Side, the only real estate technology company that exclusively partners with high-performing agents, teams, and independent brokerages to transform them into market-leading boutique brands. The collaboration will ensure that The Wellmakers Group’s client-centric, tech-driven service is powered by the industry’s most advanced platform

Cision
Nov 22nd, 2022
Mythos Real Estate Partners With Side, Leveraging Pristine Back-End Sy

Michael Mena, Founder of Mythos Real Estate Mythos Real Estate is a refreshing company designed to improve my clients’ lives, help my agents grow, and become an industry leader. Mythos Real Estate today announced its partnership with Side, the only real estate technology company that exclusively partners with high-performing agents, teams, and independent brokerages to transform them into market-leading boutique brands and businesses. The alliance will ensure that Mythos Real Estate, a coastal-friendly, client-focused real estate brand, is powered by the industry’s most advanced platform

Cision
Nov 21st, 2022
Coastal Villages Real Estate Partners With Side To Make More Clients’

Judy Griffin, Founder of Coastal Villages Real Estate We fight hard for our clients’ best interests while creating a seamless process that ensures that everyone is satisfied with the results. Coastal Villages Real Estate today announced its partnership with Side, the only real estate technology company that exclusively partners with high-performing agents, teams, and independent brokerages to transform them into market-leading boutique brands and businesses. The alliance will ensure that Coastal Villages Real Estate’s people-centric service is powered by the industry’s most advanced platform

Cision
Nov 18th, 2022
Jump Real Estate Partners With Side In Jump Living To Empower More Peo

Jillian Petrash, founder of Jump Living We at Jump Living understand that real estate transactions require a leap of faith. Jump Real Estate today announced the launch of Jump Living and its partnership with Side, the only real estate technology company that exclusively partners with high-performing agents, teams, and independent brokerages to transform them into market-leading boutique brands and businesses. The alliance will ensure that Jump Living’s local expertise and trustworthy guidance are powered by the industry’s most advanced platform

Cision
Nov 17th, 2022
Reference Real Estate Partners With Side To Grow Its Values-Driven, Cl

The Reference Real Estate team For us, the client experience is always top of mind. Reference Real Estate today announced its partnership with Side, the only real estate technology company that exclusively partners with high-performing agents, teams, and independent brokerages to transform them into market-leading boutique brands. The collaboration will ensure that Reference Real Estate’s high-touch, tech-driven service is powered by the industry’s most advanced platform

INACTIVE