Senior Technical Support Analyst

About us

At Trainline, our purpose is to empower greener travel choices, connecting people and places. Trainline enables millions of travellers to find and book the best value tickets across carriers, fares, and journey options through our highly rated mobile app, website, and B2B partner channels.

We're Europe's leading independent rail platform, helping millions of travellers find and book the best-value rail and coach journeys across our app, website and partner channels.

Our job is to make the green travel choice the best choice. By building a better train travel experience, we help more people choose rail - creating a positive impact for customers, our business and the planet.

We're a team of more than 1,000 Trainliners from over 50 nationalities, working across London, Paris, Barcelona, Milan, Edinburgh and Madrid. Now is a brilliant time to join us and help shape the future of travel.

Introducing the Workplace Technology team at Trainline

Our Workplace Technology team owns and manages the corporate technology stack of business and workplace solutions, driving innovative, cost efficient, future ways of working.

The Tech Support team is a critical part of the Workplace Technology team, ensuring Tier 2 and Tier 3 support services are delivered effectively and efficiently within a culture of continual service improvement, aligned to Trainline values.

The team is principally responsible for end user computing across a MacOS estate under central management using JAMF Pro, and a Microsoft Windows estate integrated with Azure Active Directory and Microsoft Windows Servers. This is a highly visible team, also providing dedicated AV/VC support for meeting rooms and internal events - ensuring high availability, instilling trust, and enabling a seamless experience for Executive-level presenters.

About the Role

This is not just a senior technical position - it is a leadership role within the team. We are looking for someone who takes genuine ownership: of problems, of standards, of team capability, and of the overall service we deliver to Trainliners. You will be the go‑to person when things get complex, the one who sets the bar for quality, and the one who actively lifts others to reach it.

You will work closely with the Workplace Technology Lead, acting as a technical anchor for the team - driving consistency, mentoring your peers, championing best practices, and making sure nothing important falls through the cracks. If you see something that isn’t right, you fix it. If a junior engineer is stuck, you help them through it. If a process is broken, you own improving it.

Technical Leadership & Team Ownership

• Acting as the technical escalation point for the team - owning complex incidents end-to-end and ensuring nothing stalls without clear direction
• Mentoring and upskilling junior and mid-level engineers: pairing on problems, reviewing their work, and sharing knowledge deliberately and consistently
• Setting and maintaining quality standards for ticket management, documentation, and technical investigations across the team
• Driving team readiness - identifying skill gaps, flagging them to the Lead, and taking initiative to close them through coaching or knowledge sessions
• Leading by example in attitude, thoroughness, communication, and follow-through - shaping the team culture through daily behaviour
• Supporting the Workplace Technology Lead with operational decisions, workload balancing, and service improvements

Incident, Problem & Request Management

• Owning the full incident lifecycle for complex and high-priority issues - from triage and investigation through to resolution and post-incident review
• Conducting deep root cause analysis: reviewing logs, correlating cross-system patterns, engaging third-party vendors, and documenting findings clearly
• Ensuring the team’s ticket queue is healthy - proactively monitoring dashboards, reassigning where needed, and preventing SLA breaches before they happen
• Driving problem management: identifying recurring incidents, initiating investigations, and leading permanent fix efforts rather than accepting repeat workarounds
• Owning escalation quality - ensuring issues are fully investigated, clearly documented, and appropriately packaged before being escalated to Tier 3 or vendors

Microsoft 365, Azure AD & Identity Management

• Advanced administration of Microsoft 365 services: Exchange Online, SharePoint, Teams, OneDrive, and the M365 Security & Compliance Centre
• Azure Active Directory: user and group lifecycle, Conditional Access policy design and troubleshooting, SSPR, MFA enforcement, and RBAC
• Leading SSO/SAML integrations for new SaaS platforms - configuring, testing, and documenting alongside the security team
• Owning access package governance and token management processes, ensuring alignment with policy and audit requirements
• Supporting licence governance: E3/E5 procurement, assignment, cost awareness, and flagging any out-of-policy requests to the appropriate stakeholder

AV/VC & Events Support

• Taking ownership of the AV/VC estate - maintaining full health of meeting room systems including display hardware, conferencing codecs, room controllers, and peripherals
• Proactive health monitoring using remote administration tools, with performance analytics and regular firmware/software updates
• Leading in-person and remote technical delivery for internal events and Executive/all-hands presentations
• Acting as the senior point of contact for AV issues, ensuring fast resolution and minimal meeting disruption across all sites
• Documenting AV configurations and building runbooks that enable the wider team to support the estate confidently

End User Computing & Device Management

• Advanced MacOS and Windows 11 management via JAMF Pro and Microsoft Intune/Autopilot - including policy authoring, troubleshooting complex deployment failures, and estate-wide configuration management
• Overseeing the quality of on/off-boarding processes: laptop builds, IT inductions, IAM compliance, deprovisioning, and asset retrieval
• Driving IT Asset Management maturity: inventory accuracy, lifecycle planning, hardware refresh adherence, and secure disposal compliance
• Working knowledge of Android and Linux environments; able to support edge cases confidently

Security, Compliance & Governance

• Championing security standards across the team - ensuring all activity aligns with ISO 27001, PCI-DSS, and internal policy
• Leading the team’s contribution to audit and compliance reviews: ensuring evidence is well-organised, processes are followed, and findings are acted on
• Owning the leavers process for sensitive cases - coordinating deprovisioning, data access controls, and asset recovery in line with CISO and privacy requirements
• Supporting MFA rollout, access policy governance, and SSO governance initiatives with appropriate rigour and documentation
• Ensuring all advice given to the team is backed by security sign-off and documented reference - not informal Slack approvals

Documentation, Process & Continuous Improvement

• Owning and continuously improving the team’s knowledge base - SOPs, runbooks, known error records, and onboarding guides must be accurate, accessible, and up to date
• Identifying process inefficiencies and owning their improvement: not just flagging them but designing, implementing, and embedding the fix
• Driving automation and tooling improvements - proposing and where possible implementing AI, ML, and scripting solutions that reduce toil and improve consistency
• Ensuring approvals, decisions, and audit trails live in the ticketing system - not in Slack channels

Our Tech Stack requires solid experience of

• Windows 11 and Apple ecosystem in an enterprise environment (+ working knowledge of Android & Linux)
• Mobile Device Management: JAMF Pro and Microsoft Intune - policy creation, complex troubleshooting, and deployment strategy
• Microsoft 365 administration - Exchange Online, Teams, SharePoint, OneDrive, and M365 Security & Compliance Centre
• Azure Active Directory - user lifecycle, Conditional Access, SSPR, MFA, and RBAC at an administrative level
• Modern workplace solutions: Autopilot, Intune, MFA, and cloud migration strategies
• Platform integrations, SSO/SAML - configuration, fault diagnosis, and documentation
• AV/VC hardware and software: room systems, conferencing platforms, and peripheral management
• Networks: TCP/IP, DNS, DHCP, LAN, WAN, and wireless
• Windows Command Line / PowerShell & Apple Scripting / BASH - beyond basics; able to write and adapt scripts
• SaaS applications including Slack, Atlassian suite, and cloud printing solutions
• ITSM platforms: lifecycle ticket management, SLA reporting, and queue ownership
• Security tools, best practices, PCI-DSS, and ISO 27001
• Runbook authoring and technical documentation to a high standard

Desirable Certifications

• Microsoft 365 Certified: Endpoint Administrator Associate (MD-102)
• Microsoft 365 Certified: Administrator Expert or Security Administrator Associate
• Azure fundamentals
• Apple certifications for MacOS: ACSP (ACTC), JAMF 100
• CompTIA A+ or Network+
• ITIL Foundation v4 or V5

We'd love to hear from you if you...

• Take genuine ownership - you don't wait to be told, you see what needs doing and you do it
• Have the technical depth to anchor a team: complex problems don't rattle you, they motivate you
• Actively lift those around you - you share knowledge freely, coach patiently, and take pride in the team’s performance, not just your own
• Communicate with clarity and confidence at all levels, from a junior engineer to an Executive stakeholder
• Conduct thorough, methodical investigations - you dig into logs, correlate patterns, and document what you find before reaching conclusions
• Have a genuine security-first mindset and understand why governance and audit trails matter
• Spot broken processes and own fixing them - not just flagging them
• Work autonomously under pressure, exercising sound judgement and knowing when to escal
• Are happy to be onsite as needed, including for events and critical incidents

The Interview Process

• Recruiter Call
• Competency-based interview with 2x Engineers (45 mins)
• Panel interview with key Workplace Technology stakeholders (30 mins)

Additional Information

Enjoy fantastic perks like private healthcare & dental insurance, a generous work from abroad policy, 2-for-1 share purchase plans, extra festive time off, and excellent family-friendly benefits.

We prioritise career growth with clear career paths, transparent pay bands, personal learning budgets, and regular learning days. Jump on board and supercharge your career from day one!

Our values represent the things that matter most to us and what we live and breathe every day, in everything we do:

• Think Big - We're building the future of rail
• Own It - We focus on every customer, partner and journey
• Travel Together - We're one team
• Do Good - We make a positive impact

We know that having a diverse team makes us better and helps us succeed. And we mean all forms of diversity - gender, ethnicity, sexuality, disability, nationality and diversity of thought. That's why we're committed to creating inclusive places to work, where everyone belongs and differences are valued and celebrated.

Interested in finding out more about what it's like to work at Trainline? Check us out on LinkedIn, Instagram and Glassdoor.

Please note: This role requires 5 days a week in our London Farringdon Office.

More information:

Enjoy fantastic perks like private healthcare & dental insurance, a generous work from abroad policy, 2-for-1 share purchase plans, an EV Scheme to further reduce carbon emissions, extra festive time off, and excellent family-friendly benefits.

We prioritise career growth with clear career paths, transparent pay bands, personal learning budgets, and regular learning days. Jump on board and supercharge your career from day one!

We're operating a hybrid model and ask that Trainliners work from the office a minimum of 60% of their time over a 12-week period. We also have a 28-day Work from Abroad policy.

Our values represent the things that matter most to us and what we live and breathe everyday, in everything we do:

• Think Big - We're building the future of rail
• Own It - We focus on every customer, partner and journey
• Travel Together - We're one team
• Do Good - We make a positive impact

We know that having a diverse team makes us better and helps us succeed. And we mean all forms of diversity - gender, ethnicity, sexuality, disability, nationality and diversity of thought. That's why we're committed to creating inclusive places to work, where everyone belongs and differences are valued and celebrated.

Interested in finding out more about what it's like to work at Trainline? Why not check us out on LinkedIn, Instagram and Glassdoor!

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