Head of IT & Security

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 are seeking a hands-on, strategic, and results-driven Head of IT & Security to build and scale the internal IT and security function at Dwelly. This role will focus on establishing scalable processes, standardising infrastructure, and driving security and operational discipline across the group, ensuring reliable, secure, and efficient internal operations across multiple entities and newly acquired agencies. The successful candidate will combine strong operational execution, leadership, and systems thinking, and will play a critical role in shaping the long-term foundation of Dwelly’s internal IT and security capabilities. This is a key leadership role at Dwelly. Over the next 12–24 months, you will build and scale the internal IT & Security function to support a rapidly growing, acquisition-driven organisation. You will play an important role in integrating newly acquired agencies, establishing a unified and secure operating model across the group, and driving the company’s readiness for ISO 27001 and similar frameworks. You will also define internal standards for IT, security, and access governance, ensuring consistency, scalability, and operational resilience — ultimately building systems that support thousands of properties, agencies, and internal users at scale. Key Responsibilities 1. Leadership & Strategy • Define and execute the IT and security strategy aligned with Dwelly’s growth through acquisitions • Build, lead, and scale the internal IT & Security function, including ITOps and external vendors • Establish clear KPIs across access management, onboarding speed, security posture, and operational reliability • Drive a culture of ownership, discipline, and continuous improvement across internal IT and security • Act as the primary decision-maker for internal IT and security topics across the group 2. Operational Excellence & Process Development • Design and implement scalable processes for onboarding, offboarding, and access lifecycle management • Establish and enforce security baselines across endpoints, identity, and internal systems (MFA, patching, access reviews, etc.) • Standardise workplace infrastructure across the group (devices, Google Workspace, telephony, internal tools) • Ensure compliance readiness for ISO 27001 and similar frameworks • Bring structure and control to fragmented environments across multiple entities and acquired agencies • Own internal IT and security risk posture, including access controls, audit readiness, and incident response processes • Define and enforce security policies, standards, and controls across the organisation 3. Cross-functional & Internal Collaboration • Partner closely with Engineering, Product, Operations, Finance, and Legal to align IT and security with business needs • Support secure integration of newly acquired agencies into Dwelly’s systems and processes • Act as the internal owner of IT and security topics, providing clear guidance and decision frameworks 4. Vendor & Ecosystem Management • Manage external vendors across IT, security, and infrastructure • Define and enforce SLAs, security requirements, and performance standards • Optimise vendor stack for cost, reliability, and scalability • Identify opportunities to simplify and consolidate tools across the group Qualifications and Preferred Background Core qualifications • 7+ years of experience in internal IT, security, or a related field • Proven track record of building or significantly improving IT and/or security functions in fast-growing or complex environments • Experience operating in multi-entity, acquisition-driven, or distributed organisations • Hands-on experience with identity & access management, onboarding/offboarding, and workplace infrastructure • Experience preparing for ISO 27001, Cyber Essentials Plus, or similar frameworks • Strong leadership and stakeholder management across technical and non-technical teams • Ability to design and implement scalable systems, processes, and controls • Solid understanding of security fundamentals (access control, endpoint security, patching, incident readiness) • Strong organisational and execution skills, with attention to detail • Ability to bring structure to ambiguous and fragmented environments Preferred: • Experience in proptech, fintech, payments, or other regulated / sensitive environments • Experience with post-M&A integration and infrastructure standardisation • Background in consulting, strategy, or operational transformation • Experience working with AI tools and automation in IT/security workflows Compensation and benefits • 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.