IT Support Engineer at Dwelly

About Dwelly Dwelly — a UK-based, AI-enabled lettings and property management platform, that is growing through a roll-up strategy acquiring estate agencies. The company leverages two arms: i) acquiring existing letting agencies, effectively buying its highly sticky, recurring revenue-type landlords portfolios, and then ii) building a top-notch technology to automate tenant management, payments, and post-rental property maintenance. The company seamlessly integrates AI services to automate all business processes within brick-and-mortar real estate agencies, integrating them into a tech-enabled digital letting platform in two months to radically improve the user experiences and increase efficiency of the business. We’re a fast-growing, product-focused company, backed by top-tier investors and led by a team with deep experience in real estate, technology, and operations. Position Summary We’re looking for an IT Support Engineer to join our growing team and take ownership of internal IT operations, technical support, and agency systems integration across acquired businesses. This role sits at the intersection of support, infrastructure, and M&A integration, ensuring our teams stay productive while newly acquired agencies are successfully connected into the Dwelly platform. You will work closely with internal stakeholders, external MSPs, contractors, and the integration team, with direct impact on business continuity, employee experience, and acquisition success. Key Responsibilities 1. Internal IT Support & Employee Lifecycle Management Own day-to-day IT support for the internal team through our ticketing system, ensuring issues are resolved quickly and effectively. Manage employee onboarding and offboarding processes, including device setup, account provisioning, access control, and maintaining accurate access records. Support end users across tools such as Microsoft 365, Google Workspace, Slack, Notion, Jira, and other business-critical systems. 2. Infrastructure Coordination & Technical Operations Act as the technical point of coordination with our managed service providers (MSPs) and third-party contractors, tracking delivery, escalating priorities, and providing technical direction where needed. Troubleshoot infrastructure issues such as VPN connectivity, remote access, networking, email delivery, and device management. Maintain and improve internal systems reliability, security, and operational efficiency across a distributed environment. 3. Acquisitions Integration & Agency Systems Consolidation Work closely with the integration team to assess the technology stack of acquired agencies and centralise technical assets. Support migrations from legacy environments, including on-premise Windows servers, websites, email systems, domains, hosting, file storage, and user accounts. Connect newly acquired agencies to Dwelly’s core platforms including payment systems, referencing providers, and operational tools while minimising disruption during transition 4. Automation, Administration & Continuous Improvement Administer and optimise internal tools including Jira, Slack, Notion, Microsoft 365, Azure, Intune, Google Workspace, and related SaaS systems. Identify repetitive manual processes and automate them through scripting, APIs, workflows, or AI tools wherever possible. Continuously improve support operations, documentation, access management, and system scalability to support Dwelly’s rapid growth. Qualifications and Preferred Background Core qualifications • Strong communication skills and fluency in English. • Higher degree education. • Experience supporting macOS, Linux, and Windows environments. • Experience administering Microsoft 365, Google Workspace, Slack, Jira, and Notion. • Strong networking fundamentals including DNS, VPN, SSL, firewalls, SSH, routers. • Ability to troubleshoot hardware, software, access, and user support issues independently. • Strong problem-solving skills – ability to approach challenges logically and propose practical solutions. Preferred background • Experience with Azure, Entra ID, Intune, Active Directory, Autopilot. • Experience with WordPress, hosting environments, domains, redirects, migrations. • SQL knowledge across MySQL/PostgreSQL. • Experience with APIs, webhooks, Postman, Swagger. • Experience supporting acquisitions, migrations, or multi-site environments. • Scripting ability in Bash or PowerShell. Ways of working • Startup mentality: resilience, adaptability, and ability to thrive in a fast-paced environment. • Customer-centric mindset: focus on delivering value to end-users or clients. • Highly proactive, with the ability to identify risks early and solve problems before incidents occur. • Ownership mindset with confidence managing MSPs and contractors. • Enthusiasm for AI tools and process automation. Compensation and benefits • The role is fully remote, providing flexibility and enabling seamless collaboration with our geographically distributed team • Competitive salary with the potential for equity options based on performance, recognising exceptional contributions to our integration success What is it like being a Dwell-er Feel free to check out Dwelly Core Principles. That’s about what we believe in, how we operate and make decisions What we offer is not a fancy office or a static workplace. Instead, this is solving one of the world’s most complex problems in the largest consumer industry in the world (residential rentals), to improve the experience for over 30% of households (more than 5 million in the UK, and over 100 million including EU and US) that live in rental homes This is about disrupting the largest, most antiquated industry in the world, with one of the strongest operational and technical teams that exist in the UK and the EU. We work hard, and we shoot for extremely ambitious results. But we want people to be proud of what they’ve built and be able to look back and say one day “hell yeah, that was me that did it all” • Customer obsession rather than competitive focus • Passion for invention • Operational excellence • Long-term thinking By applying for this position, you consent to the processing and storage of your personal data for recruitment purposes for up to 365 days, in accordance with our data retention policy and applicable data protection laws.