Head of Information Technology

Ledgebrook is an InsurTech MGA on a mission to bring Specialty insurance into the modern era. Burdened with legacy technology and processes, the industry has not kept pace with the speed of innovation seen in other sectors. Positioned at the cutting edge of the next generation of InsurTech, Ledgebrook offers the best of both worlds: innovative world‑class technology deployed by a leadership team armed with over 100 years of insurance expertise. Our long‑term vision is to become a diversified full stack Specialty re/insurer competing with legacy carriers in product lines & markets across the globe. To get there, Ledgebrook builds its premium base by rolling out a new Specialty product every ~6 months until we prove enough traction to raise a balance sheet, become a full stack carrier and eventually compete in the reinsurance markets. Our initial product is a domestic primary and excess GL E&S policies sourced via wholesale brokers. At Ledgebrook, everything we do is driven by our culture: Care, Strive, Thrive Together. To succeed in modernizing the industry, we must first succeed in changing the way we do business. Talent density is our north star; fewer, better people working together as one. To that end we’ve replaced all individual incentives with generous equity packages‑we play as a team, we win as a team. Everyone benefits handsomely from Ledgebrook’s success.

About the Role

We’re looking for an experienced and hands‑on Director of IT to oversee all aspects of Ledgebrook’s information technology operations. This role reports to the Director of Security & Infrastructure and will be responsible for ensuring the reliability, security, and scalability of the company’s IT environment in a fully remote setting. The ideal candidate thrives in both strategy and execution, someone who can define long‑term IT strategy, manage vendor relationships, and roll up their sleeves to solve day‑to‑day technical challenges. This person will serve as the connective tissue between our end users, our outsourced IT partner (Xceedance), and our internal infrastructure and security leadership.

What you’ll do

• Oversee all IT operations, including hardware and software lifecycle management, endpoint administration, and network reliability
• Manage our third‑party IT provider (Xceedance) to ensure high service quality and alignment with internal SLAs
• Provide support for all users across the organisations situated in India, Europe and The Americas.
• Own the onboarding and offboarding process; provisioning and deprovisioning through Rippling, ensuring secure and seamless access to company systems
• Administer core IT systems including Google Workspace, Jira, Rippling, and our Google Enterprise MDM environment
• Lead the IT Helpdesk function; triage, prioritize, and track tickets via Jira Helpdesk, ensuring timely resolution and continuous improvement
• Collaborate with Security & Infrastructure leadership to implement IT controls, endpoint protection, and data retention policies
• Define and track key IT metrics (uptime, SLA compliance, satisfaction scores, etc.) to measure and improve performance
• Develop and document IT policies, procedures, and knowledge bases to support growth and compliance objectives
• Coordinate asset inventory management, software licensing, and vendor renewals
• Support SOC 2 and other compliance efforts, ensuring IT systems align with internal policies and external standards
• Champion an excellent employee IT experience, focusing on responsiveness, reliability, and user satisfaction

About you

Here at Ledgebrook we are passionate about creating a team that is on a continuous learning journey and that shares our excitement about building a company from the ground up. Some of the characteristics we hold dear are:

• A passion to deliver a world‑class service experience to every team member, ensuring technology is an enabler, not a barrier, to doing great work
• Intellectual curiosity and a desire for innovation, rather than following the status quo
• A strong operational mindset and sense of urgency to balance getting it right with getting it done right now
• A drive to win together as a high‑performing team
• A moral compass to “do the right thing, period”. We have zero tolerance for toxic behaviors

Requirements

Must haves

• 5+ years of progressive experience in IT operations, with at least 2 years in a leadership role
• Proven success managing outsourced IT providers and internal service delivery
• Experience in managing a user base across different timezones.
• Hands‑on experience administering Google Workspace, MDM, and SaaS‑based IT environments
• Strong knowledge of ITIL or other helpdesk best practices
• Experience managing onboarding/offboarding, access control, and endpoint lifecycle in remote‑first organizations
• Familiarity with tools like Rippling, Jira Service Management, and Google Enterprise MDM
• Excellent communication and organizational skills, with the ability to manage multiple priorities simultaneously
• A customer‑first mindset and ability to communicate effectively with technical and non‑technical audiences
• Working knowledge of IT security and compliance principles

Nice to haves

• Prior startup or high‑growth company experience
• Familiarity with SOC 2, ISO 27001, or similar frameworks
• Experience with identity and access management (Okta, Azure AD, or Google Identity)
• Knowledge of endpoint protection, patch management, and device compliance tools
• Background in automating IT workflows (e.g. through Rippling or scripting)
• Experience managing IT budgets, procurement, and vendor contracts

Please note: This position is open only to candidates who are authorized to work in the United States without the need for current or future employer‑sponsored work authorization. We are unable to offer visa sponsorship at this time

Benefits

• Competitive salary + meaningful equity ownership
• 100% employer‑paid health insurance
• 100% remote work, flexible hours
• Unlimited paid time off
• Work with an ambitious, smart, fun team to transform a $1T global industry
• Ownership, autonomy, purpose