IT Support & Systems Engineer (Part Time) at Trust & Will in Remote

Founded in 2017, Trust & Will is the leading digital estate planning platform, trusted by over one million users. We provide modern, accessible solutions to help families protect their legacies with attorney-approved, legally valid documents tailored to individual state requirements. Our seamless online platform simplifies the estate planning and settlement process, empowering individuals to create wills and trusts while also partnering with financial advisors, attorneys, and institutions to make legacy planning more inclusive and affordable.

About You

We’re looking for a skilled, motivated IT professional who’s comfortable working hands-on while thinking strategically about how to scale support through smart tooling and automation. 

• Embodies ownership in action: you see a problem, you fix it, you look for ways to prevent it from recurring.
• Comfortable with AI tools and eager to integrate them into everyday IT workflows where they drive efficiency.
• Self-driven toward ambitious goals with a bias for high-quality, timely delivery.
• Thrives in the hands-on, fast-paced environment of a small remote-first company.
• Strong problem-solving skills with an instinct for translating needs into scalable solutions.
• Excellent communicator and collaborator who works effectively cross-functionally.
• Passionate about enabling people through self-service, clear documentation, and smart automation.

About the Role*

As a key member of our remote IT team, you’ll play an essential role in shaping a modern, efficient IT environment at a fast-growing startup. This role combines hands-on support with opportunities to drive strategic initiatives — whether that’s optimizing our endpoint management, tightening security posture, or finding the right places to apply AI and automation. We’ve already invested in tools like Risotto (our AI-powered ITSM platform) and automated many workflows, so you’ll be building on a strong foundation rather than starting from scratch.

This is a part-time, hourly position averaging 25 hours per week, with occasional flexibility in hours based on business needs (e.g., covering during team absences). Core availability during Pacific Time Zone business hours (M-F, 1–6 PM PT) is expected.

*This is an hourly, non-exempt role.

Responsibilities

IT Support & Ticket Management

• 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.

Endpoint Deployment & Management

• 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.

Onboarding & Offboarding

• 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.

Identity & Access Management

• 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.

SaaS Management & Vendor Operations

• 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.

Asset Lifecycle Management

• 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.

Network & Office Infrastructure

• 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.

Security & Compliance

• 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.

Automation & Tooling

• 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.

Documentation & Knowledge Sharing

• 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.

Qualifications

• 2–5 years of IT experience in a fast-growing startup or similar environment.
• This is a part-time, hourly position averaging 25 hours per week, with occasional flexibility in hours based on business needs (e.g., covering during team absences). Core availability during Pacific Time Zone business hours (M-F, 1–6 PM PT) is expected. Being located in San Diego, CA is preferred but not required.
• 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)

Bonus Points

• 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.

Employee Benefits & Perks:

• Compensation: Salary + Equity
• Our salary range for this position is $48 - 60 per hour, in addition to compensation we also include an employee equity package as a component of our offer along with other benefits and perks outlined below. 
• Extra
• Financial wellness benefits (unlimited 1:1 sessions with a UBS financial coach)
• Guest speakers & reimbursement for learning opportunities
• Family-friendly work environment. We support the complexity of a remote world with the needs of families
• Optional company-sponsored events and travel throughout the year
• $250 Work from home stipend + Apple accessories 

About Trust & Will: 

• We are a remote-first company, giving our employees the flexibility they need to work in an environment that best suits their needs. Our hiring process is also conducted virtually unless otherwise noted. We are a company that was founded in San Diego, CA, and offer a collaborative co-working space that is available for you to use if you'd like but not required. #LI-Remote
• We are proud to be a certified B Corporation, using business as a force for good. We are committed to building a healthy, sustainable, and engaging working environment for all employees, their families, and communities. We publish an annual impact report to outline our positive contributions to our world and set an example for all employers.
• Trust & Will's mission is to help every family leave their legacy through affordable, accessible estate planning. That starts with the people we hire and the ways in which we support the development of their unique talents and capabilities. We are committed to prioritizing ways to make our company and industry more inclusive. This means we must be revolutionary in the way we value diversity to revolutionize our business sector. At Trust & Will, everyone has a seat at the table and space to be their authentic selves because only in a company that is inclusive and diverse can we truly stand in our members' shoes.

California Privacy Notice: Trust & Will collects personal information from applicants including identifiers, professional/employment history, and education information to evaluate qualifications and communicate about your application. California residents have the right to know what information we collect, request a copy, correct inaccuracies, or request deletion (subject to exceptions). To exercise these rights, contact legal@trustandwill.com. For more information, visit our privacy policy.

Trust & Will may use AI tools to assist with administrative recruiting tasks. All final hiring decisions are made by people. For accommodations, contact people-ops@trustandwill.com.