1st Line IT Support Analyst – Microsoft 365 Specialist

Location: Borehamwood, WD6 1JD
Salary: £25,000 – £30,000 DOE + Excellent Benefits
Contract: Full time, Permanent
Benefits: 20 days holiday plus bank holidays, Bupa Cash plan with EAP support after 1 month service, 4% Pension contribution (matched by employee), Stock options after 1 years’ service, Private Health Insurance after 2 years’ service

Are you passionate about Microsoft 365 and looking to build your career in a modern, forward-thinking IT environment

At Chalkline, we’re not just another IT support company. As a Microsoft Solutions Partner in Modern Work & Azure Infrastructure (with an Advanced Specialisation in Azure Virtual Desktop), we pride ourselves on delivering exceptional client experiences while developing and supporting our people.

We’re growing, and we’re looking for a 1st Line Technical Support Analyst with hands-on Microsoft 365 knowledge to join our friendly Service Desk team.

What you’ll be doing as our 1st Line IT Support Analyst:

• Acting as the first point of contact for clients, resolving inbound support tickets and calls.
• Troubleshooting and supporting Microsoft 365, Azure, Intune, Windows Servers, and networking tools.
• Monitoring proactive alerts and carrying out preventative maintenance (backups, patching, disk space checks, etc).
• Delivering outstanding customer service while developing your technical expertise.
• Working with the latest technologies: Microsoft 365, Azure, Intune, Windows, macOS, networking & server tools.

What we’re looking for

To hit the ground running, you’ll ideally have 2–3 years’ experience in a 1st line support role and proven knowledge in:

• Microsoft 365 administration & support (essential)
• Microsoft Azure & Entra
• Intune & Active Directory
• Windows Server (2019 / 2022 / 2025)
• Networking basics – routing, switching & firewall rules
• Printer troubleshooting & general IT support
• Strong written and verbal communication skills

Why join us

We invest in our people and their future – offering training, certifications, and opportunities to grow. Alongside a competitive salary, you’ll also benefit from:

• 28 days holiday (including bank holidays) + your birthday off (increasing with service)
• Healthcare – Medical Cash Plan + EAP after 1 month; Private Medical Insurance after 2 years
• 4% matched pension contributions
• Share scheme – join after 1 year of service
• Regular team socials & away days (think axe throwing, darts, mini golf & more!)
• Free parking, training programmes & career development opportunities

Ready to apply

If you’re passionate about IT support and have the Microsoft 365 expertise to make an impact, we’d love to hear from you.

Click APPLY today to join Chalkline and take your career to the next level!

No agencies please.