IT Support Specialist – Level 2

YourSIP IT Services is a growing Managed Service Provider supporting businesses throughout the Tampa Bay area. We’re known for taking a modern, client‑focused approach to IT — building long‑term relationships, solving real problems, and giving our technicians ownership over the work they do.

As a Microsoft CSP Partner, we specialize in the adoption and delivery of Microsoft 365 modern work solutions, alongside core managed IT services that keep our clients productive, secure, and supported.

We’re looking for an IT Support Specialist – Level 2 who enjoys working directly with users, thinking holistically about systems, and taking ownership of issues from start to finish.
It is a hands‑on, client‑facing position, not a Level 1 support role, call‑center, or ticket‑churn position.

You’ll work across multiple client environments, providing remote support from our Palm Harbor office as well as local onsite support as needed.

This is an excellent opportunity to learn a wide range of modern technologies, gain exposure to diverse client environments, and have a real, visible impact on both client success and the growth of our IT services team.

As an IT Support Specialist – Level 2, you’ll serve as a trusted technical resource for escalated and more complex support needs. You’ll be responsible for diagnosing issues, implementing effective solutions, and ensuring problems are fully resolved — not just passed along.

Success in this role requires strong troubleshooting skills, good judgment when working with users, and comfort operating in a fast‑paced MSP environment where no two days look exactly the same.

• Serve as a primary, client‑facing technical resource for advanced support requests
• Provide Tier 2 user support across desktops, applications, systems and access issues
• Troubleshoot and support Windows desktop environments and core business applications
• Support Windows Server fundamentals, including Active Directory, file access, and login‑related issues
• Diagnose and resolve network and connectivity issues, including DNS, DHCP, VPNs, and wired/wireless access
• Deploy network equipment: firewalls, switching and Wi Fi
• Provide helpdesk‑level administration and troubleshooting for Microsoft 365 environments (beyond basic user creation and password resets)
• Own issues end‑to‑end, including investigation, resolution, documentation, and client communication
• Participate in client projects such as onboarding/offboarding, migrations, system cleanups, and environment improvements
• Work collaboratively with teammates and assist with escalation support when needed
• Perform onsite client visits for support and project work as required

• 3+ years of IT support experience in a professional environment
• Strong troubleshooting skills across user systems, networks, and server fundamentals
• Comfortable supporting multiple users, systems, or environments
• A customer‑first mindset with the ability to communicate clearly with non‑technical users
• An ownership mentality — you take responsibility for solving problems, not just escalating them
• High School Diploma

• MSP or multi‑client experience preferred, but not required
• Associates, Bachelors or technical degree in technology related field
• Microsoft 365 administration or troubleshooting experience
• Exposure to security tools, backups, or device management platforms
• Relevant certifications (Microsoft, CompTIA, or similar)
• Full‑time, on‑site role with local client travel (Tampa Area)
• Occasional after‑hours or on‑call rotation
• Must be local to the Greater Tampa Bay Area
• Not a remote position
• Driving:
  Clean driving record, employee provided vehicle
• PTO, Paid Holidays and Technical Certification Assistance

This role is a good fit for someone who:

• Enjoys owning problems and seeing them through
• Likes working directly with users and clients
• Wants exposure to multiple environments and technologies
• Is looking to grow within a true Level 2 MSP support role,
  not an entry‑level help desk position