First Line IT Support Engineer

Toronto, Canada

About RedCompass Labs

RedCompass Labs are payments experts focused exclusively on payments modernization. Over the last 23 years, RedCompass Labs has delivered 500+ projects across the world’s major payments schemes and platforms, including ISO 20022, SEPA, Swift, the Real-time Payments Network, and FedNow, ISO 20022 migrations, and FIS OPF, Finastra GPP, and ACI Worldwide. Its flagship Payments Expert Agent is an AI solution purpose-built for the full payments modernization software development lifecycle. Trained on decades of deep payments expertise and more than 30,000 curated documents, the agent is certified to SOC 2 Type II. RedCompass Labs supports clients from offices in London, Warsaw, Brussels, Miami, Boston, Toronto, and Pune. For more information, visit www.redcompasslabs.com.

Role Description

We are seeking a dedicated and proactive First Line IT Support professional to join our Global Corporate IT team. This is a hands-on role suited to someone with solid 1st line experience who is comfortable resolving the majority of incidents independently and is ready to take on more complex troubleshooting that sits at the boundary of 2nd line. You will be the first point of contact for our employees, playing a critical role in their day-to-day productivity and their experience of IT as a function. The successful candidate combines strong technical capability with a genuine service mindset — someone who can diagnose a problem quickly, explain it clearly to a non-technical user, and leave the person feeling supported rather than processed.

What you will be doing

Provide first-line technical support to employees via phone, email, remote support tools, and in person . Act as the first point of triage for incoming tickets, accurately categorising, prioritising, and either resolving issues directly or escalating to 2nd/3rd line with clear, well-documented context. Troubleshoot and resolve a broad range of hardware and software issues across Windows and macOS estates, including connectivity, authentication, peripherals, and core business applications. Manage the full lifecycle of end-user devices: imaging, configuration, deployment, asset tagging, and decommissioning of laptops, desktops, mobile devices, and peripherals. Administer user accounts and access across Microsoft 365, Active Directory / Entra ID, and other core business systems — including starters, leavers, and movers processes. Install, configure, and maintain software, including license management and patching where appropriate. Support audio-visual and meeting room technology, ensuring conference rooms and Teams Rooms are reliable and ready for use. Maintain accurate records in the ticketing system, ensuring tickets are updated regularly with progress, resolution steps, and clear closure notes. Contribute to and maintain the internal knowledge base, writing clear, accurate documentation for both IT colleagues and end users. Deliver IT inductions for new joiners and provide ongoing training and guidance to employees on tools and best practice. Identify recurring issues and trends, proposing improvements to reduce ticket volume and improve the user experience. Ensure compliance with company standards, security policies, and IT procedures at all times. Collaborate closely with global IT counterparts to deliver consistent, high-quality support.

Required Skills and Experience

Proven experience in a 1st line (or blended 1st/2nd line) IT support role within a corporate environment, ideally supporting several hundred users or more. Strong working knowledge of Microsoft Windows 10/11 and macOS, including troubleshooting at OS level (not just application level). Hands-on experience administering Microsoft 365 — including Exchange Online, Teams, OneDrive, and SharePoint — at user-administration level. Familiarity with Active Directory and/or Entra ID (Azure AD): user and group management, password resets, MFA, and basic security group administration. Practical experience with endpoint management tooling such as Intune, Jamf, or equivalent. Comfortable troubleshooting networking basics: Wi-Fi, VPN, DNS, IP, and common connectivity issues, with the judgement to know when to escalate. Experience using a ticketing system (e.g. ServiceNow, Jira Service Management, Freshservice, Zendesk) and a working understanding of ITIL principles such as incident, request, and problem management. Excellent problem-solving skills with a structured, methodical approach to diagnosis. Strong communication skills — able to translate technical concepts into plain language and adjust tone for different audiences, from junior staff to senior executives. A genuine customer-service mindset: patient, empathetic, and focused on the person as well as the problem. Strong organisational skills, attention to detail, and the ability to manage competing priorities calmly. Ability to work independently and take ownership of issues through to resolution, while also collaborating effectively across a global team.

Desirable

ITIL Foundation certification. Microsoft certifications (e.g. MS-900, MD-102) or Apple certifications (ACSP). Experience supporting a hybrid or globally distributed workforce across multiple time zones. Exposure to scripting (PowerShell, shell) for routine task automation. Experience with mobile device management for iOS and Android.

Why Join RedCompass Labs?

Work on high‑impact financial technology projects that shape the future of payments and AI‑driven innovation Join a trust‑based, transparent, and collaborative culture where your voice matters and ideas influence outcomes Enjoy real ownership and autonomy in how you approach challenges, deliver work, and grow your expertise Be part of a diverse and inclusive global team across Canada, the UK, Europe, and Asia, where fairness and meritocracy guide every decision Collaborate daily with senior industry experts and leaders, accelerating your professional development Experience a human, respectful, and well‑structured recruitment and onboarding journey designed around clarity and mutual fit Grow through continuous learning, cross‑functional work, and exposure to both consulting and product‑building environments Join a company that values integrity, curiosity, and continuous improvement, and empowers you to make meaningful impact from day one.

Competitive Package

Competitive base salary and a performance bonus (up to 10% of annual salary) Medical insurance for you and your family 22 days of annual leave + public & bank holidays

Please Note

Before applying, please review the requirements carefully: We can only consider candidates based in Toronto, Canada - applications from outside this region will not be considered. This role requires a on-site 5 days a week presence in our Toronto office. Candidates must be able to attend regularly on an agreed basis.

RedCompass Labs is committed to building a diverse and inclusive workplace, ensuring fair and equitable opportunities for all. This commitment drives innovation and enables us to deliver better outcomes for our clients.