Lead Helpdesk Engineer; MSP

Lead Helpdesk Engineer (MSP Experience Required) Compensation: $60,000–$75,000 base

A fast-growing Managed Services Provider based in Lisle, IL is seeking a Tier 2 Helpdesk Engineer to join its expanding technical team and take on a lead-level presence within the service desk. This MSP supports small to mid-sized businesses with IT support, consulting, network design, and cybersecurity solutions and has earned recognition as one of the Best Workplaces in Illinois due to its strong culture of accountability, camaraderie, and continuous learning.

This role is ideal for someone who enjoys being hands-on with tickets but also wants to lead by example—helping drive ticket quality, coaching Tier 1 teammates, and owning the customer experience. It’s a strong fit for a Tier 2 engineer who wants a clear runway toward Tier 2.5 / Junior Sys Admin growth, while still staying close to the day-to-day operations of an MSP.

• Work tickets end-to-end across multiple client environments—diagnosis, troubleshooting, resolution, and documentation
• Serve as a senior presence in the shared queue, helping maintain pace, quality, and proper escalation flow
• Provide remote and occasional onsite support for desktops, laptops, printers, and networked devices
• Administer and support Microsoft 365 environments (Exchange Online, Teams, SharePoint, Entra , Security Center, etc.)
• Perform account administration, permissions, onboarding/offboarding tasks, and basic system administration
• Use PSA, RMM, and documentation tools to keep environments and ticketing standards clean and consistent
• Partner with senior engineers/tech leads on escalations and gain exposure to more complex issues
• Contribute to internal knowledge articles and repeatable troubleshooting playbooks
• Help reinforce a culture of ownership—attempt solutions first, elevate thoughtfully, and follow through to closure

This is not a management role, but the right person will act as a technical lead within the helpdesk function by:

• Coaching Tier 1 engineers on troubleshooting approach, ticket hygiene, and client communication
• Helping triage the queue and identify patterns, recurring issues, and opportunities for improvementli>
• Owning the “how” behind support delivery: documentation, consistency, accountability, and follow‑up
• Supporting onboarding/ramp of new technicians through shadowing and structured guidance
• Raising risks early and helping prevent repeat incidents through better process and standards

Successful candidates will have prior experience working in a Managed Services Provider (MSP) environment and be comfortable supporting multiple client environments.

• Windows desktop troubleshooting and end‑user support
• Networking fundamentals, printers, workstation configuration, and remote support tools
• PSA/RMM/documentation platforms (Auto Task, Datto, IT Glue, Connect Wise, or similar)
• Exposure to common MSP stacks such as:
• Security/networking tools like Watch Guard, Barracuda, Aruba (or similar)

• A dependable Tier 2 engineer who can handle hybrid work without losing productivity
• Someone who stays calm under pressure and takes ownership through completion
• A team‑first mindset—help others level up, share knowledge, and raise the standard
• Strong communication (clients and internal), solid judgment, and attention to detail
• High curiosity and commitment to self‑education and continuous improvement
• Associate or Bachelor’s degree in an IT‑related field, or equivalent hands‑on experience
• After training: hybrid schedule (2–3 days onsite or at client sites, remainder remote)
• Competitive base salary: $60K–$75K, depending on experience
• Profit sharing
• Medical insurance + telemedicine
• Dental, vision, life, short‑term and long‑term disability insurance
• Legal assistance services
• Retirement plan with company match
• Certification bonuses + ongoing learning support