IT Support & Systems Engineer (Part Time)

Trust & Will is the leading digital estate planning platform, trusted by over one million users. They are seeking a skilled IT professional to provide hands-on support while driving strategic initiatives in a fast-paced, remote-first environment.

Responsibilities:

• Act as the primary point of contact for IT issues, providing tier-1 and tier-2 support across the organization
• Manage and prioritize IT requests through Risotto, our AI-powered ITSM platform, ensuring timely and effective resolution
• Continuously improve Risotto's AI capabilities by refining workflows, training responses, and optimizing deflection rates
• Log, track, and resolve IT incidents while maintaining a high standard of customer service
• Oversee device management for macOS using Kandji and Windows using Intune
• Maintain and refine Intune configurations to ensure seamless, secure device management across the Windows fleet
• Implement and improve zero-touch deployment strategies for all endpoints
• Monitor device health and compliance, proactively addressing issues before they impact end users
• Maintain and optimize our automated onboarding and offboarding workflows, ensuring reliable access provisioning and device setup for new hires and departures
• Collaborate with People Operations to continuously improve the employee lifecycle experience
• Troubleshoot and iterate on automation where edge cases arise
• Administer and enhance our Okta environment, including SAML/SCIM integrations and Okta Workflows
• Manage access policies with a least-privilege mindset, conducting regular access reviews
• Automate access provisioning and deprovisioning where possible to reduce manual overhead
• Manage the SaaS application lifecycle: tracking licenses, renewals, usage, and spend across the company's tooling portfolio
• Conduct regular SaaS audits to identify redundant or underutilized tools and drive cost optimization
• Identify and address shadow IT by maintaining visibility into unsanctioned tools and working with teams to consolidate or approve them
• Manage the end-to-end hardware lifecycle for a remote workforce — procurement, configuration, shipping, tracking, retrieval, and secure disposal
• Maintain an accurate asset inventory with clear records of device assignments, warranty status, and refresh cycles
• Coordinate with vendors and logistics partners to ensure timely delivery of equipment to new hires and replacement devices
• Manage Meraki office network infrastructure including Wi-Fi, switch and firewall
• Support conference room AV systems and video conferencing technology
• Provide remote connectivity support, troubleshooting VPN and network access issues for distributed employees
• Maintain and enforce security policies across platforms such as Google Workspace, Okta and other third-party tools
• Support SOC II compliance efforts by documenting IT security measures and assisting with audits
• Identify and flag shadow IT, unusual access patterns, and potential security risks
• Identify opportunities to automate manual IT processes, whether through scripting, no-code platforms, or AI-powered tools
• Evaluate and recommend new tools and technologies that improve efficiency, security, or the employee experience
• Collaborate cross-functionally to surface automation opportunities beyond IT
• Contribute to and maintain an internal IT knowledge base with clear, up-to-date documentation
• Ensure Risotto's knowledge base is well-maintained so AI-assisted support stays accurate and helpful
• Build self-service resources that empower employees to resolve common issues independently

Requirements:

• 2–5 years of IT experience in a fast-growing startup or similar environment
• Expertise with macOS and Windows, including device management tools like Kandji and Intune
• Proficiency administering at least three of: Okta, Google Workspace, Slack, Atlassian, 1Password, Notion, Rippling, OpenVPN, AWS
• Familiarity with SOC II compliance requirements and security protocols
• Experience with AI-powered ITSM platforms (e.g., Risotto) or traditional ticketing systems (e.g., JSM, Freshservice)
• Experience managing SaaS application portfolios
• Familiarity with network infrastructure fundamentals (Wi-Fi, VPN, firewalls) and office IT setup
• Comfort using AI tools in your workflow; you don't need to be an ML engineer, but you should be someone who naturally reaches for AI when it can help
• Strong troubleshooting skills with a proactive, automation-minded approach
• Excellent communication and interpersonal skills with a customer-service orientation
• This position is available to candidates residing in the following states only: California (CA), Colorado (CO), Florida (FL), Georgia (GA), Idaho (ID), Illinois (IL), Maryland (MD), New Jersey (NJ), New York (NY), North Carolina (NC), South Carolina (SC), Pennsylvania (PA), Texas (TX), Vermont (VT)
• Being located in San Diego, CA is preferred but not required
• Experience building or refining AI-assisted support workflows
• Hands-on experience with Okta Workflows, scripting (Python, Bash, PowerShell), or no-code automation platforms
• Experience managing Meraki network environments or similar enterprise networking stacks
• Track record of running SaaS audits and driving measurable cost savings
• Experience managing hardware logistics for a distributed, remote-first workforce
• Familiarity with AV/conference room technology
• Familiarity with how AI tools can be applied to IT operations
• Experience supporting a remote-first workforce with distributed tooling