Service Desk Engineer II | Managed Services, Automation & AI

Job Description

Job Description

DECISION DIGITAL

Service Desk Engineer II

Managed Services, Automation & AI

• Reports To: Service Delivery Manager

• Practice: Managed Services (shared resource with ConnectWise Consulting)

• Key Partners: Service Desk Lead, Tier-2/3 Engineers, Consulting Project Managers

• System of Record: ConnectWise Manage

• Employment Type: Full-time, exempt

• Work Location: Hybrid - three days in office, two days remote, with occasional travel to client sites in metro Atlanta

• Compensation: $65,000 - $75,000 base, commensurate with experience

Role Summary

The Service Desk Engineer II is accountable for resolving client issues quickly and correctly on the front line of our Managed Services practice, and for continuously reducing the volume of work that reaches the front line in the first place.

This role is built for one of two candidates: an experienced Tier 1 engineer ready to move into Tier 2 work, or a newer Tier 2 engineer who wants to go deep on automation, workflow design, and applied AI inside an MSP.

A core expectation of this role is leverage. We are not hiring another pair of hands to absorb ticket volume. We are hiring someone who resolves today's tickets well and then removes the cause so we do not see them again. Automation and AI capability is written into the job, not deferred to spare time.

Operating Context

Decision Digital runs two delivery practices: a mature Managed Services practice and a dedicated ConnectWise Consulting division. Engineers are shared resources across both. ConnectWise is our system of record for all work.

Practically, this means you will spend most of your time on managed services delivery, with periodic allocation to MSP-owned projects and, as you develop, to ConnectWise consulting engagements. It also means scheduling discipline and accurate time entry are not administrative overhead here - they are how the business stays coordinated.

Core Responsibilities

A. Service Desk Delivery

• Own tickets end to end on the Tier-1 and Alerts boards: triage, diagnose, resolve, and communicate with the client throughout

• Resolve on first touch wherever possible; escalate only when genuinely warranted, and hand off with complete notes so the Tier-2/3 engineer is not restarting the investigation

• Manage your own queue against SLA response and resolution targets; surface risk early rather than reporting it after the miss

• Work security and monitoring alerts from RMM, MDR, and SaaS monitoring platforms - validate, remediate, or escalate with judgment about signal versus noise

• Maintain backlog health on your assigned work; no silent aging tickets

B. On-Site Client Support

On-site work is occasional rather than routine - typically a couple of visits per month across the team. But when we do go, it is usually because the problem could not be solved remotely, and you will be there alone. The bar for on-site capability is high precisely because the frequency is low.

• Travel to client sites in the metro Atlanta area for issues that cannot be resolved remotely, scheduled maintenance, deployments, and project work

• Diagnose network problems on site independently - trace the fault through the physical layer, switching, routing, wireless, and ISP demarcation to isolate root cause

• Work hands-on with network hardware: switches, firewalls, access points, patch panels, structured cabling, and PoE infrastructure

• Troubleshoot wireless coverage, interference, roaming, and AP placement issues in live client environments

• Coordinate directly with ISPs, circuit providers, and third-party vendors when the fault sits outside our perimeter, and hold them accountable to resolution

• Deploy, rack, and cable equipment during onboarding, refresh, and remediation work

• Represent Decision Digital professionally on client premises - you are frequently the only technical person in the room, and the client's impression of us is formed by how you carry yourself

• Document what you found and what you changed before you leave the site, not days later

C. ConnectWise Discipline

• Accurate, same-day time entry against the correct ticket, agreement, and work type

• Ticket hygiene: correct board, status, type/subtype, and resolution notes that a future engineer can actually use

• Contribute to and correct client documentation and internal runbooks as you work

• Treat ConnectWise as the source of truth: if it is not in ConnectWise, it did not happen

Time entry accuracy directly drives client profitability reporting, agreement billing, and capacity planning. This is a non-negotiable standard of the role, not a preference.

D. Automation, Workflow & AI

• Identify recurring ticket patterns and eliminate them through scripting, scheduled remediation, self-healing alerts, or upstream configuration change

• Propose and implement improvements to ConnectWise workflows - routing, board structure, status flows, templates, notification logic

• Help design, test, and deploy AI-assisted tooling for the service desk: knowledge-base-driven assistants, ticket triage and summarization support, documentation generation, and agreement/billing triage

• Train teammates on new automations and tooling, gather feedback, and iterate; an automation nobody trusts or uses is not a win

• Measure and report the operational impact of your work - tickets deflected, hours returned, escalations avoided

• Ensure automation serves business outcomes and client experience, not automation for its own sake

E. Project & Cross-Practice Support

• Support MSP-owned projects including client onboarding, infrastructure lifecycle, and remediation work

• Deliver assigned project tasks on schedule and communicate blockers early

• As capability develops, support ConnectWise consulting engagements alongside consulting project managers

• Respect the scheduling commitments made across practices; flag conflicts to the Service Delivery Manager rather than silently reprioritizing

Key Success Metrics

• SLA compliance across assigned tickets

• First-contact resolution rate

• Escalation rate and escalation quality (are handoffs clean?)

• Time entry accuracy and timeliness

• Client satisfaction (CSAT) on assigned tickets

• Measurable efficiency gains delivered through automation

Qualifications

• 2+ years in an MSP, IT service desk, or internal IT support role with direct end-user contact

• Solid Microsoft 365 administration: user and license management, Exchange Online, SharePoint/OneDrive, and core Entra ID identity and access concepts

• Practical Windows desktop and Windows Server troubleshooting ability

• Demonstrated ability to diagnose network issues on site, not just remotely - isolating faults across cabling, switching, VLANs, routing, DNS, DHCP, VPN, wireless, and firewall rules, and determining whether the problem is ours, the client's, or the carrier's

• Comfort working hands-on in a network closet: reading a patch panel, tracing a cable run, checking link and PoE status, and interpreting switch and firewall configuration

• Experience working tickets in a PSA or ITSM platform with disciplined documentation and time logging

• Strong written and verbal communication; can explain a technical problem to a non-technical client without jargon or condescension

• Demonstrated curiosity about automation, even if informal - scripts written to save yourself time, workflows rebuilt, tools self-taught

• Valid driver's license, reliable transportation, and willingness to travel occasionally to client sites in the metro Atlanta area

• Able to lift and position equipment during deployments and rack work

Preferred Qualifications

• PowerShell scripting ability; any exposure to Python, REST APIs, or JSON

• Hands-on ConnectWise Manage and ConnectWise RMM (Asio) experience

• Hands-on configuration and troubleshooting experience with business-class firewalls, managed switches, and wireless controllers - WatchGuard, Ubiquiti, Meraki, or similar

• Experience with EDR/MDR platforms, email security, or SaaS security monitoring

• Real hands-on experience using AI tooling for actual work - what you have built or automated with it, not what you have read about it

• Certifications: Microsoft MS-900, AZ-900, MD-102; CompTIA Network+ or Security+; or vendor certifications in our stack

• Prior MSP experience with multi-tenant environments and agreement-based billing

Our Environment

You do not need hands-on experience with every platform below. You do need to learn new tooling quickly and go deep on it.

• PSA & RMM: ConnectWise Manage, ConnectWise RMM (Asio), ScreenConnect

• Identity & Productivity: Microsoft 365, Entra ID, Intune, Azure Virtual Desktop

• Security: SentinelOne, Huntress, Microsoft Defender, SaaS Alerts, WatchGuard Firebox

• Backup & Continuity: Axcient x360, M365 backup

• Documentation & Visibility: Liongard, Hypervault

• Analytics & AI: Crushbank, Synthreo, Claude and other LLM tooling

Must Haves

• Ownership mentality - you finish what you start and you follow up without being asked

• Comfort saying clearly when you do not know something, and then going and finding out

• Systems thinker who looks for leverage rather than working harder at the same thing

• Willingness to challenge "this is how we have always done it" and propose the better way

• Operates independently without micromanagement

• Comfortable being the only technical person on site, making decisions without a teammate to check with

• High standards of precision - in the fix, in the notes, and in the time entry

Non-Starters

• Ticket-closers who optimize for volume over root cause

• Chronic escalators who pass work up rather than learning it

• Candidates who blame tools, clients, or teammates

• Loose documentation and time entry habits

• Interest in AI as a buzzword rather than as something they have actually used to do work

• Needs daily direction to stay productive

Growth Path

This role is a ramp, not a holding pattern. Within 12 to 18 months, a strong performer should be positioned for one of the following based on where their strengths land:

• Tier 2/3 Engineer - deeper technical ownership of escalations, infrastructure, and security engineering

• Automation & Systems Engineer - ownership of the automation, integration, and AI tooling roadmap across the practice

• Project Engineer - leading client onboardings, migrations, and solution deployments

• ConnectWise Consultant - moving into the consulting practice on client-facing ConnectWise implementation and optimization engagements

We will discuss which direction you are pointed toward early and revisit it regularly. Certification is company-paid - we would rather invest in you than replace you.

Compensation & Benefits

• Base salary: $65,000 - $75,000 annually, commensurate with experience

• Health care: 100% coverage for the individual employee

• Retirement: 401(k) with company match; eligible after one year of employment, immediately vested

• Paid time off: Two weeks PTO plus paid company holidays

• Birthday: Paid day off for your birthday

• Certification: Company-paid certification program available

• Work schedule: Hybrid - three days in office, two days remote, with occasional on-site client visits in metro Atlanta

• On-call: Light monthly rotation

• Mileage: All business miles reimbursed at the current IRS rate for office-to-client travel

• Wellness: Access to our rooftop gym and pool

Culture

• We believe culture is our moral center

• We are not human doings - we are human beings

• We don't motivate - we inspire

• We row together

• We believe in knowing what to do and doing it

• We invest time in your success

• We champion teamwork and cooperation

• We are driven by precision and integrity

Interview Focus Areas

• Troubleshooting methodology - how they isolate a problem, not just whether they know the answer

• Walkthrough of an on-site network issue they diagnosed: what they checked, in what order, and how they proved root cause

• A specific example of something repetitive they automated or eliminated

• How they decide when to escalate versus keep working a ticket

• Client communication under pressure, including delivering bad news

• Documentation and time entry habits in their current role

• Practical experience with AI tooling - what they built, what it saved, where it failed

• Self-direction and follow-through without daily oversight

Decision Digital is an equal opportunity employer. We evaluate all applicants without regard to race, color, religion, sex, sexual orientation, gender identity, national origin, age, disability, veteran status, or any other protected characteristic.

Decision Digital is a human-led, AI-powered ConnectWise consultancy and managed IT services provider, Atlanta-based since 1997. We're a working MSP and the team other MSPs call to get ConnectWise right — pairing platform-level consulting with full-service managed IT, cybersecurity, Azure, and Microsoft 365 for growth-driven organizations.

Company Description

Decision Digital is a human-led, AI-powered ConnectWise consultancy and managed IT services provider, Atlanta-based since 1997. We're a working MSP and the team other MSPs call to get ConnectWise right — pairing platform-level consulting with full-service managed IT, cybersecurity, Azure, and Microsoft 365 for growth-driven organizations.