Director of Operations, VDI

RIA in a Box Careers

We are looking for a driven, and motivated team leader and senior systems engineer to contribute to the future of a fast-growing entrepreneurial company. When joining as a Director of Operations, VDI, you will be expected to provide technical leadership to our System Admins and Systems Engineers and quality support to clients for a variety of technical issues. You will be working with current staff on fixing issues remotely, using powerful remote access tools, and providing guidance for our cloud and onsite client environments. Limited on-site work at clients’ offices may be required from time to time. You will assist with projects which may range in complexity from troubleshooting Active Directory issues to deploying complete virtual or physical network build-outs.

You can learn more about our team and company culture here:

What You'll Do

  • Assist with projects which may range in complexity from troubleshooting Active Directory issues to deploying complete virtual or physical network buildouts
  • Coordinate with clients and vendors to resolve IT issues for clients
  • Assist current technical staff in troubleshooting issues
  • Create automated solutions for repeated client issues
  • Install hardware and software on an as needed basis
  • Provide client support via our remote access tools
  • Provide clients with onsite support on an as needed basis
  • Document all work of any kind for clients in the ConnectWise Manage PSA (ticketing system). Classify work according to appropriate categories
  • Assist in the review of ConnectWise Automate alerts and resolve any issues or alerts that may arise on the Workstation and Server categories
  • Collect network hardware and software information
  • Create Client Deliverable Documentation (E.g. project plans, solution recommendations, etc.)
  • Create client specific Network Documentation and diagrams using MS Visio (or a like product)
  • Maintain relevancy of all client Network Documentation

What We're Looking For

  • 10+ years of proven Windows Workstation, Window Server, and Domain systems administration experience
  • 10+ years of proven networking configuration and troubleshooting experience (TCP/IP, CIDR Subnetting, Routing, DNS, Windows TLS Cert Management, etc.)
  • 5+ years of technical lead experience, responsible for mentoring and team nurturing, within a Managed Services Provider (MSP) or equivalent environment
  • Microsoft Certified MCSE (or equivalent experience)
  • Cisco certified CCNP (or equivalent experience)
  • Amazon AWS Certified Solutions Architect (or equivalent experience)
  • Domain level administration within Windows Servers in Active Directory environments
  • Active Directory management via GPOs
  • Ability to effectively and quickly troubleshoot internet services (email, DNS, NTP, etc.) and quickly learn how to configure new network devices (firewalls, VPNs, routers, WAPs, etc.) and AWS solution equivalents
  • Experience with Microsoft 365 (Office 365, Azure AD, etc.), Amazon AWS (CLI and web console), MSP type tools (ConnectWise Automate, Manage, Control), and Multi-tenant services
  • Comfortable with remote access tools (VPN, RDP, Bomgar, Control, etc.) and in high-paced research, learn, and share situations regarding new software or technologies


  • Attractive base salary + bonus compensation
  • Unlimited paid time off, plus holidays
  • Exceptional medical, dental, insurance, and 401(k) benefits
  • You will be working directly for the Head of Operations, Virtual Desktops, in designing and developing the evolution of the Virtual Desktop product
  • Directly contributing to the growth and success of a rapidly growing business
  • Ongoing professional development and direct training
  • Comradery and real time communication with like-minded colleagues

Think you're a good fit? Apply below!

RIA in a Box® is a fast-growing, entrepreneurial financial services and technology firm, providing the leading number of registrations and ongoing compliance services to RIAs throughout the United States. Our mission is to provides the leading compliance solution for investment advisers. We put the client first by delivering innovative software and expert advice.
 RIA in a Box is an Equal Opportunity Employer. All qualified applicants will receive consideration for employment without regard to their race, religion, ancestry, national origin, sex, sexual orientation, age, disability, marital status, domestic partner status, or medical condition.