Chris S.
Managed Services - Technical and Operations - ConnectWise PSA/RMM
Senior managed services expert with 20+ years of overall experience in IT and 15+ specifically in managed services. This experience bridges two areas: technical and internal operations. His technical experience focuses on leading senior technical work in all areas of SMB IT, with significant amounts of both project work and day-to-day technical support in addition to long-term IT strategy planning, account management, and consulting for MSP client base and MSPs in general. Technical experience is primarily but not only in Microsoft Windows Server and desktop operating systems, Active Directory and assorted common server roles, Office 365 and Exchange, Hyper-V and VMware virtualization, clustering and storage, Mimecast, Proofpoint and other email security platforms, identity management (SSO, MFA, SAML), the Azure platform, backup systems like Datto and Veeam, firewalls (SonicWALL, Sophos XTM and UTM plus some exposure to Fortigate and Palo Alto), Cisco and Cisco Meraki, Extreme Networking, Brocade, Ruckus, HP and Dell switching, Ubiquiti, and others. Chris also has significant experience and education in IT and information security in general. On the operational side, Chris's expertise includes comprehensive work in internal managed services operations, both building and expanding new and existing practices from start-ups to mature businesses. Specific areas of managed services experience aside from technical service delivery to clients includes, but is not limited to: service desk management and best practices, project management and scoping, team management and individual mentoring, reporting and dashboarding, data analytics, documentation and building or maintaining documentation repositories like IT Glue, process building and efficiency-focused strategic problem solving, internal toolset systems building and deployment, PSA/ticketing and RMMs of several vendors, and various security and management tools of many types and flavors. Chris has significant experience with EOS, Connectwise Manage and Autotask PSAs, Kaseya and Automate RMMs, Brightgauge, the entire Sophos Central product line, Auvik, Liongard, Perch, Carbon Black, Cisco Umbrella, and API integrations between all of these tools and others.
Earnings and projects
Last 6 months ÷ 6
Last 6 months: $10k
Billed in all: $91,747$92k
$2.6k in the last 6 months
Across 56 contracts
Earnings, last 30 days
Skill rankings: #1 in 1 skill of 14
Rarest: top 2% in Sophos Sophos UTM, of 45. Ranked by MRR among everyone on Upwork with the skill.
- Sophos Sophos UTM45 freelancers · 🇺🇸 #1Top 2%🇺🇸#1 of 5
- #6SonicWall24 freelancers · 🇺🇸 #1Top 25%🇺🇸#1 of 5
- #13VMware ESX Server178 freelancers · 🇺🇸 #3Top 7%🇺🇸#3 of 31
- #14ConnectWise Automate81 freelancers · 🇺🇸 #2Top 17%🇺🇸#2 of 9
- #15Help Desk Software91 freelancers · 🇺🇸 #5Top 16%🇺🇸#5 of 21
- #22Managed Services137 freelancers · 🇺🇸 #7Top 16%🇺🇸#7 of 28
- #26Microsoft Hyper-V Server236 freelancers · 🇺🇸 #4Top 11%🇺🇸#4 of 38
- #36Firewall448 freelancers · 🇺🇸 #10Top 8%🇺🇸#10 of 90