Head of Engineering

Digitailor; Tampa (FL); Hybrid; USD 130,000 - 180,000; Full time

Benefits offered by this job

Annual performance bonus

Funded certifications & training

Remote work with travel

Job summary

System Crew is seeking a Group Head of Engineering to lead in-house engineers and contractors across multiple locations, including the US and UK, with remote work and regular travel. You will shape an engineering organisation that scales, setting clear ownership and adopting AI and automation.

You will report to the Group Managing Director, collaborate with sales on solution design, and drive delivery of complex IT transformations, cloud migrations, and security baselines while maintaining

Qualifications

• At least 10 years in IT infrastructure and systems engineering.
• Experience leading multi-country engineering teams.
• Current Microsoft certifications at Associate level or higher.
• Fluent written and spoken English.
• Willingness to travel regularly.

Responsibilities

• Lead and develop engineering teams across locations with clear ownership.
• Plan resources and workloads to deliver projects on time.
• Set engineering standards, architecture references, and security baselines.
• Collaborate with sales/pre-sales on design and bids.
• Promote AI/automation in daily workflows.

Skills

Leadership

English proficiency

Strategic planning

Team management

AI & automation

Education

Microsoft certifications (Associate level or higher)

Azure Solutions Architect Expert

Tools

Azure

Microsoft 365

Entra ID

Intune

Windows Server

Virtualization

Backup & recovery

Data centre & cloud migrations

Job description

Head of Engineering System Crew Group United Kingdom, Florida, North Carolina or South Carolina. Full-time, remote with regular travel. ______________________________ About System Crew System Crew is a managed IT services group operating from eight countries across North, Central and South America, the Caribbean and Europe: the United States, Costa Rica, Brazil, the British Virgin Islands, the United Kingdom, Germany, Switzerland and Poland. Its own engineers work alongside a network of specialist contractors, associates and delivery partners, and the group holds partner status with around 40 technology vendors. System Crew designs, builds and runs IT infrastructure for organisations with demanding requirements and supports client operations in more than 70 locations worldwide. Clients include international organisations, government bodies, global logistics and supply chain companies and regulated financial services firms, with work delivered across the Americas and Europe. Recent work includes complete IT separations of business units from their former parent companies, new-site build-outs and long-term managed service contracts. The group is certified to ISO 9001 and ISO/IEC 27001.

The Role

The Group Head of Engineering leads the group’s engineering function: in‑house engineers and specialist contractors who deliver projects, run client environments and staff the service desk, spread across seven hours of time difference from Central Europe to Central America.

The Role

carries full responsibility for how engineering work is planned, delegated, delivered and documented, and for raising the technical standard of the team. The group is growing, and the role is expected to build an engineering organisation that scales with it: one that delivers on time, runs on clear ownership, and uses AI and automation as a normal part of daily work.

The Role

reports to the Group Managing Director and works closely with sales and pre‑sales on solution design and bids.

The Role

suits someone who genuinely enjoys infrastructure engineering, keeps up with technology out of interest, is still comfortable opening a console to understand a problem, and takes pride in environments that run quietly and well.

Responsibilities

Leadership and management Lead, organise and develop the engineering team across all locations, with clear ownership, delegation and accountability for every project and client environment. Plan resourcing and workload so that projects and client commitments are delivered on time, and report progress, risks and slippage early and honestly. Run a working rhythm suited to a distributed team: clean handovers across time zones, written documentation as the default, regular one‑to‑ones and team reviews. Hire, onboard and develop engineers in several countries, manage performance, and build a layer of team leads who can run work without constant escalation.

Travel

to team locations and client sites as needed, including the United States, Costa Rica, Brazil, the British Virgin Islands, the United Kingdom, Germany and Switzerland.

Engineering and service delivery

Set and enforce engineering standards: reference architectures, build standards, change and release management, patching, backup and recovery testing, and security baselines. Act as the senior technical authority and final escalation point for complex incidents and designs. Lead the technical delivery of transformation projects, including IT separations (carve‑outs), data centre and cloud migrations, and new‑site build‑outs. Own service quality against SLAs for the service desk and managed services. Own the engineering side of the group’s management systems and their audits, currently ISO 9001 and ISO/IEC 27001. AI and automation Use AI assistants and agents daily for scripting, automation, documentation, troubleshooting and analysis, and make this the normal way the team works. Replace repetitive manual work with automation and measure the effect on delivery time and margin. Set rules for AI use that keep client data protected and consistent with ISO/IEC 27001 and client contracts. Partners, clients and commercial Own the technical side of vendor partnerships, including the certification plan that keeps the group qualified for Microsoft Solutions Partner designations and other vendor programmes. Support pre‑sales and tender work with solution designs, effort estimates and technical responses. Serve as senior technical contact for key clients, including regulated financial services firms and public‑sector bodies. Keep engineering effort within budget and contribute to service pricing and margins.

Requirements

At least 10 years in IT infrastructure and systems engineering, including substantial time at a managed service provider or in a complex multi‑site environment. A track record of leading engineering teams spread across countries and time zones, and of delivering projects on time through delegation rather than by doing the work personally. Deep expertise in the Microsoft platform (Azure, Microsoft 365, Entra ID, Intune, Windows Server), backed by current Microsoft role‑based certifications at Associate level or above. Azure Solutions Architect Expert is expected within the first year if not already held. Broad, vendor‑neutral command of the rest of the infrastructure stack: virtualisation, backup and recovery, virtual desktops, identity and endpoint security. Working knowledge of networking is sufficient. Regular, practical use of AI tools in engineering work. Full professional fluency in written and spoken English. Resident in the United Kingdom, Florida, North Carolina or South Carolina, with existing right to work there. Advantages 15 years or more of experience. Spanish language skills. Experience in regulated environments, especially financial services. Experience with IT separations (carve‑outs) and data centre or cloud migrations. Experience working within ITIL practice and ISO/IEC 27001 or ISO 9001 management systems. Further certifications in cloud, virtualisation, backup or security from any major vendor.

Terms

Full‑time, permanent. Remote, with regular travel. Competitive salary and generous annual performance bonus, plus funded certifications and training.