The AI-Forward IT Support Engineer is the visible face of IT at CAIS headquarters. This role owns the day-to-day support experience-managing the support team, serving as the senior escalation point, and making sure employees can get things done. Alongside that, this person is a genuine practitioner of AI tools, using them to manage, maintain, and engineer solutions in the Microsoft ecosystem.

The AI dimension here is practical and people-facing: comfort with tools like Claude and Codex, the ability to get employees access to what they need, and the enthusiasm to show someone how to write their first useful prompt. The goal is to be the person who makes AI feel accessible, not intimidating.

Key Responsibilties

Pillar 1 - IT Support Leadership & Microsoft Estate

• Support Team Management: Manage CAIS's support function firmwide, leveraging internal staff and MSP resources. Hold partners accountable for performance and drive continuous improvement in service quality.
• Senior Escalation Point: Act as the senior escalation point for all end-user support issues across the organization. Own complex or unresolved tickets through to resolution, ensuring no issue falls through the cracks between the support team and internal stakeholders.
• Microsoft Environment Management: Lead day-to-day administration and engineering of the CAIS Microsoft estate: Intune device policies and compliance profiles, Azure / Entra enterprise application management, and M365 service health. Beyond break-fix-this includes proactive configuration, policy improvement, and keeping the environment clean and well governed.
• Visible Face of IT: Be physically present and accessible at CAIS HQ. Build trust with employees as the go-to person when something isn't working-whether that's a support issue or a question about technology. Represent IT in a way that is responsive, human, and credible.

Pillar 2 - AI Operations & End-User Enablement

• AI Tooling Comfort: Use Claude Code and OpenAI Codex as primary tools for engineering solutions in the Microsoft environment-generating and refining scripts, automating repetitive admin tasks, troubleshooting configurations, and improving documentation. AI tooling is how this person works, not an afterthought.
• AI Access Operations: Ensure CAIS employees have access to the AI tools they need. Manage provisioning, permissions, and basic configuration for end-user AI platforms. Be the first point of contact when someone can't get in, doesn't know where to start, or needs a tool set up.
• On-Ramp & Evangelism: Help colleagues take their first steps with AI tooling. Run informal sessions, share practical tips, introduce basic prompt engineering concepts, and be available for one-on-one guidance. The goal is not deep training-it's making the tools feel approachable and getting people to their first win as quickly as possible.

Required

• Experience managing a support function-internal team, MSP, offshore, or a combination; comfortable holding vendors and partners accountable to service standards
• Strong hands-on knowledge of Microsoft 365, Azure / Entra ID, and Intune-able to own configuration and policy work, not just administer tickets
• Comfortable daily user of Claude Code, OpenAI Codex, or equivalent AI tooling-applied to real engineering and administrative tasks
• Excellent communication and interpersonal skills-comfortable engaging at all levels of the organization and able to explain technology clearly to non-technical users in plain, practical terms

Preferred

• Financial services industry experience or a similar fast-paced, entrepreneurial environment

Qualifications

• 5+ years of progressive IT experience
• 2+ years leading a support function or small team
• Demonstrated experience using AI tools (e.g., Copilot, ChatGPT, Claude)
• Hands-on expertise in automating Microsoft 365, Azure, and Intune environments

CAIS' compensation package includes a market competitive salary, a performance bonus, and exceptional benefits. If you are located in New York, New York, the base salary range for this role is $120,000 - $155,000. Actual compensation is influenced by a wide array of factors including but not limited to skill set, level of experience, and specific office location.

CAIS offers a comprehensive benefits package that includes generously subsidized healthcare with 100% employer paid dental and vision insurance, an employer matched retirement plan, wellness programs, and generous PTO and parental leave. For this role we do require a minimum of 4 days in office per week. For more information on our benefits and career opportunities, please visit our website: https://www.caisgroup.com/our-company/careers.

We use technology, including AI tools, to support parts of our recruitment process such as application screening, interview scheduling, and candidate communications. These tools are used to improve efficiency and consistency, but they do not replace human judgement. All hiring decisions are made by people, and we are committed to fair and unbiased assessment of every candidate.