Trust & Will Remote - USA Full-time

We’re on a mission to help every family leave their legacy with a fast, easy, and secure way to create, manage, and distribute their estate plan online. Since 2017, we’ve helped hundreds of thousands of families plan for their future with a streamlined and intuitive approach that makes estate planning simple, affordable, and accessible. We’re backed by leading names in venture capital including Jackson Square Ventures, Link Ventures, Revolution’s Rise of the Rest, Halogen Ventures, and more.
If you would like to join us, we are looking for an IT Support & Systems Engineer to play a pivotal role in bringing all IT management functions in-house to cover all support processes and automation, device and tooling administration, and security access needs.
About You
We are seeking a highly skilled and motivated individual who possesses the following qualities:
– Embodies ownership in action; Holding yourself accountable for the development of a robust in-house support function
– Self-inspired towards ambitious goals and ensuring timely high-quality delivery and support
– Appreciates the hands-on nature, pacing, and flexibility required when contributing effectively in a small remote-first company
– Excellent problem-solving skills and the ability to identify, source, and translate needs into scalable solutions
– Strong communication and collaboration skills, with the ability to work effectively with cross-functional teams and stakeholders
Passion for enabling people through self-service and documentation

About the Role

  • As an IT Support & Systems Engineer, your responsibilities will include:
  • Device Management and Identity Access
  • Provide first-level support for hardware, tooling, and access needs
  • Oversee onboarding and offboarding processes, managing accounts as well as hardware provisioning and de-provisioning for new employees and contractors
  • Implement a support ticketing system and prioritize self-service capabilities and documentation
  • Lead towards appropriate SSO solutions
  • System Stability, Security, and Upgrades
  • Ensure stability, performance, and security of device hardware, network access, and IT systems
  • Conduct regular system and access checks
  • Implement preventive maintenance measures for SOC 2 compliance
  • Data Backup and Recovery
  • Develop and implement reliable device data backup and recovery strategies
  • Diagnose and resolve hardware and software issues promptly
  • Manage device connectivity, security, and network access
  • Documentation and Compliance
  • Create and maintain detailed documentation of system configurations
  • Document employee onboarding/offboarding processes, IT support procedures and maintain department access templates for applications and tools 
  • Implement and maintain measures for compliance with relevant standards
  • Cybersecurity Measures
  • Implement cybersecurity measures to safeguard systems, data, and applications
  • Manage virus protection and ensure continuous security updates
  • Operational Efficiency and Automation
  • Collaborate with teams to optimize tool configurations
  • Develop and implement automation scripts for routine tasks
  • Optimize operational efficiency in device management and security through automation.
  • Utilize monitoring tools for proactive issue identification
  • Vendor, Device Management, and Technology Integration
  • Manage relationships with external vendors
  • Evaluate and integrate new technologies
  • Stay informed about industry tooling, regulations, and compliance standards
  • Monitor current device inventory and status, facilitate the ordering of new devices, manage lease renewals and upgrades, repairs or recycling/donation of current devices and ancillary hardware
  • Establish and administer standards for allowed tooling across the organization
  • Cost Optimization
  • Optimize IT costs through efficient resource management
  • Identify and propose cost-saving initiatives, especially in device management and application access
  • Reporting and Communication
  • Facilitate IT management and reporting
  • Work closely with cross-functional teams to understand and address IT needs
  • Ensure timely installation of software updates, patches, and security fixes
  • Coordinate system upgrades and enhancements, including application access and management
  • Provide requested SOCII audit report requests


  • 3-5 years of proven success as a Systems Administrator, IT Operations, or in a similar role
  • 2+ years experience with IT administration of productivity suites such as Google Workspace; IT tools such as JAMF, Kaseya, Hexnode, Apple Business Essentials; process management tools such as JIRA; VPN tooling such as OpenVPN; antivirus solutions such as MalwareBytes; communication tools such as Slack; and monitoring solutions such as Drata
  • Strong knowledge of operating systems (MacOS, Windows, Linux)
  • Proficiency in scripting languages (e.g., Python, PowerShell, Bash) and/or cross-application integrations for automation needs
  • Understanding of cybersecurity best practices and experience implementing security measures, familiarity of NIST standards
  • Familiarity with antivirus solutions (e.g., MalwareBytes) and managing virus protection
  • Excellent problem-solving skills and ability to diagnose and resolve IT issues, and provide real-time IT support to remote users
  • Strong documentation skills, including maintaining detailed records of configurations and procedures
  • Ability to work collaboratively with cross-functional teams and effective communication skills

Bonus Points for:

  • Experience working in a tech company and/or high-growth startup
  • Experience supporting a remote workforce
  • Familiarity with agile development methodologies and tools (Scrum, Kanban, JIRA)
  • Strong JAMF marketplace experience
  • Okta/SSO implementation experience
  • Familiarity with SOC II compliance

Full-time Employee Benefits & Perks:

  • Our salary range for this position is $92k – $125k, 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.
  • PTO
  • Unlimited time off that you are encouraged to use
  • Quarterly company-wide breaks (think Winter, Spring, Summer, and Fall break)
  • 1 PTO day a month to spend with friends, family, or however you choose
  • 4 days/year to volunteer in your community
  • Health and Wellness Benefits
  • Fantastic health benefits including medical, dental, vision, life insurance, and generous parental leave 
  • Financial wellness benefits (Equity & tax advisory support, savings options, and employee-sponsored 401k)
  • A informal mentorship program, guest speakers & reimbursement for learning opportunities
  • Extra
  • Flexible work schedule + hours
  • 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
  • $500 Work from home stipend + mac & Apple accessories
  • Join an Inc. Magazine Best Workplace & Inc. 5000 winner!