Senior Lead Helpdesk Engineer

Full-Time in United States - Remote OK - Senior - Operations


In this exciting and challenging role, you will join SugarShot’s Technical and Security Team as one of our TOP TECHNICAL RESOURCES in support of our clients’ users, infrastructures, networks, servers, and mobile devices. SugarShot has an international client base, operates in multiple data centers, has extensive cloud presence, and manages a large number of servers, desktops, and related networking equipment. You will work under the Director of Operations and with other Service Team professionals to fulfill your responsibilities.

This is a great opportunity to get involved in a solid, fast growing company where you'll get your hands dirty with A LOT of cool technology. Our relaxed, flexible, and remote work lifestyle encourages teamwork and dedication.

This is a remote-work position with “in-office” options (depending on your location).

SugarShot has an exciting brand and unique culture. We go our own way and we’d like you to join us on our journey to revolutionize the Managed Services Industry. You can read more about the company (and “WTF is SugarShot?”) here:

If you’re interested in –

  • Making a big impact
  • Relaxed and flexible hours
  • Remote work and work from home
  • Earned trust and responsibility
  • Working and communicating with a team of professionals
  • Growing with our company
  • Playing with the latest technology
  • Participating in fun company and department activities (even virtually)
  • Being part of something different

Then you’ll enjoy your time with SugarShot!

However, if you’re –

  • Looking for a “9-5” job
  • Looking for a corporate environment
  • Looking to be micro-managed
  • Looking to have your hand held
  • Stuck on old technology
  • Habitually tardy/absent
  • One who doesn’t deliver when you say you will
  • Not good communicating or working in a team environment
  • Someone who has owned your own company in the past

Then please DO NOT apply. You will NOT be happy here.

Essential Responsibilities & Duties

  • Support SugarShot’s and clients’ users
  • Occasional travel onsite to client locations, (depending on where you are located)
  • Log all activities in our ticketing system
  • Document common issues and resolutions for submission into our knowledge base
  • Train users, in-person and remotely
  • Administer Microsoft 365 applications and systems
  • Handle escalations from L1, L2, and L3 Helpdesk team members
  • Maintain installed hardware and software inventory
  • Ensure security and software updates are successfully applied per policies/SLAs
  • Troubleshoot server, workstation, network, and mobile hardware
  • Perform OS and application reinstalls
  • Participate as an IT team member
  • Participate in internal and client projects
  • Ability to lift 25lb
  • Perform after-hours on-call duties, per on-call rotation schedule
  • And other duties and responsibilities as assigned from time to time

Personal Qualifications

  • Must be highly detail oriented and a proven commitment to high quality workmanship
  • Must have excellent, thorough, and methodical problem solving skills
  • You must be able to work with challenging personalities and maintain a professional and positive demeanor with users at all times
  • Must have drive and a “-ness” about you that takes pride in supporting your workstations/users
  • Must be a self-starter
  • Must have exemplary interpersonal and English communication skills (spoken and written)
  • You must have a smartphone and a reliable high speed Internet connection from wherever you live
  • You must be comfortable on camera (we regularly meet on Microsoft Teams or Zoom)
  • You must maintain good personal hygiene habits
  • A good sense of humor

Technical Qualifications

  • 8+ years of experience in Helpdesk Support is REQUIRED
  • A strong understanding of Windows 10+ is REQUIRED
  • A strong understanding of Windows Server 2016+ is REQUIRED
  • A strong understanding of Mac OSX is REQUIRED
  • A strong understanding Microsoft Office is REQUIRED
  • A strong understanding of supporting Microsoft/Office 365 is REQUIRED
  • A strong understanding of VPN is REQUIRED
  • A strong understanding of WiFi connectivity troubleshooting is REQUIRED
  • A strong understanding of advanced networking (including but not limited to: VLANs, dynamic routing protocols, packet inspection) is REQUIRED
  • A strong understanding of the Internet’s architecture is REQUIRED
  • A strong understanding of cloud hosting platforms (Azure and AWS) is REQUIRED
  • Ability to write scripts to solve technical problems en masse is REQUIRED

To really stand out –

  • MSP experience is a big plus
  • Microsoft and Apple certifications are a big plus
  • Experience with ConnectWise Manage, Automate, and/or Control are a big plus
  • Cisco Meraki experience is a big plus
  • Possesses or working toward Microsoft, Cisco, Meraki, CompTIA Server+, CompTIA Network+, CompTIA Security+, or similar certifications is a plus
  • Strong VMware expertise is a big plus
  • Linux skills are a big plus
  • ITIL certification is a plus
  • Experience with Auvik is a plus
  • Experience with Veeam is a plus


  • Great pay
  • Remote work
  • Flexible schedule
  • Fantastic working environment
  • Continuing Education
  • Health insurance
  • Dental insurance
  • Vision insurance
  • Life insurance
  • Flexible Spending Account
  • Health Savings Account
  • 401K
  • Costco Membership
  • Monthly Lunch & Learn program