Head of Information Technology

Overview:

We’re a fast-growing tech company building AI-native software for the self-storage industry. Backed by an exceptional group of investors, trusted customers, and 25+ leading industry advisors – including our recent $63M Series A – we have the resources and long-term mindset to build things the right way, scale thoughtfully, and create real impact.

Self-storage is the fastest growing asset class in commercial real estate – surpassing $65 billion annually in the U.S. last year. There are more than 77,000 self-storage properties in North America, operated by more than 35,000 independent business owners who provide service to tenants. Cubby’s mission is to empower self-storage operators – from small and medium family-owned businesses to large corporate clients – by streamlining operations, optimizing processes, and reducing administrative effort, so they can focus on growing their businesses.

We are looking for a hands-on Head of Information Technology to own and continuously improve Cubby’s internal IT, security, access, and compliance operations. You will be responsible for building reliable and scalable processes that keep our people, devices, systems, and data secure and well managed as we continue to grow globally. This is a high-ownership role for someone who enjoys both setting direction and getting into the details – from managing our Apple fleet and identity infrastructure to driving SOC 2 compliance and strengthening our overall security posture while supporting a growing, distributed team.

Responsibilities

• Own and continuously improve Cubby’s internal IT, security, access, and compliance operations as the company scales.
• Manage our Apple device fleet and end-user IT environment, including device management, provisioning, security, and support for a distributed workforce.
• Own identity and access management across Google Workspace and third-party systems, including onboarding/offboarding, SSO, MFA, access reviews, and privileged access.
• Lead security operations, including endpoint security, vulnerability management, monitoring, incident response, and remediation.
• Own our SOC 2 Type II compliance program and related GRC activities, including audits, policies, risk assessments, penetration testing, and vendor security reviews.
• Support and strengthen our cloud security and administration, primarily within GCP.
• Automate recurring IT and security processes and provide clear reporting on security, compliance, and overall IT posture.
• Partner with teams across Cubby to build practical, secure, and scalable IT processes without creating unnecessary blockers.

Requirements

• Strong hands-on experience managing IT operations in a modern, cloud-based environment.
• Solid experience with Apple/macOS fleet management and MDM, ideally Iru (Kandji), Jamf, or similar.
• Strong knowledge of Google Workspace, identity and access management, SSO/SAML, MFA, and RBAC.
• Hands-on experience across security operations, including endpoint security, vulnerability management, monitoring, and incident response.
• Experience owning or playing a key role in SOC 2 Type II compliance, audits, and GRC processes; experience with Drata, Vanta, or similar is a plus.
• Experience administering cloud environments, preferably GCP.
• Comfortable using Bash and/or Python to automate IT processes and reporting.
• Strong written and spoken English, with the ability to communicate technical and security topics clearly to both technical teams and senior leadership.
• Proactive, detail-oriented, and comfortable taking end-to-end ownership in a fast-moving environment with a high degree of independence.

It will be considered an advantage if you have:

• Apple Certified IT Professional
• Professional Google Workspace Administrator
• Google Associate Cloud Engineer or Professional Cloud Security Engineer
• CompTIA Security+ or ISC2 CC

What you can expect if you join us

• An excellent team environment surrounded by experienced high-impact peers in every function
• Generous remuneration package
• Options/Shares incentive program based on contribution
• Additional health insurance
• Multisport card
• Development of novel product and systems from scratch, with a minimum of legacy integration work
• Company-sponsored team building activities and events
• Company-sponsored lunch once a week
• Biannual performance and growth reviews
• Opportunities to work and connect with the team in New York
• Remote work from any location worldwide for two weeks annually

What you can expect from the interview process

A friendly “Get-to-Know” meeting – We will share more details about the company, teams, structure, as well as learn more about you, your technical skills and personal qualities.

Role Deep Dive – A chance to meet our VP of Engineering and dive deeper into your experience, working style, and perspective on the role.

Technical Interview – A more technical conversation focused on your hands-on experience and knowledge across the key areas relevant to the position.

Final Interview – A final conversation with our CTO to get to know each other better, discuss the role from a broader perspective, and cover any remaining questions.

If you are interested in this position, please send us your CV in English!

We will contact only the candidates selected for further consideration.