Senior Director of Operations: Standing Up an AI-First Operating System

It is day 45 at Data and Technology Hub. You are the new Senior Director of Operations. The CEO has been running everything herself — there are no documented processes, no operating cadence, and no shared source of truth for decisions, budgets, or project status.

Five things need your attention right now:

• Funder scorecard: The primary funder has a quarterly review in 60 days. They expect a scorecard, a budget-vs-actuals update, and a progress narrative. Nothing is currently instrumented.
• Vendor approval process: The fiscal sponsor's finance team has flagged three vendor payments that went through without an approval workflow. They need a documented process within two weeks or they will pause all new vendor onboarding.
• Consulting engagements: Three active consulting engagements with community organizations have no intake documentation, no scoping agreements, and no record of what was promised.
• Executive Assistant onboarding: The Executive Assistant starts in three weeks with no onboarding plan, no systems access list, and no documentation of what the CEO needs supported.
• Success scorecard: The CEO has asked you to design the organization's success scorecard — but there is no agreed definition of success yet.

Data and Technology Hub is building an AI-first operating model. The CEO does not want a traditional nonprofit back office she wants an operating system that is lean, automated where possible, and designed for a five-person team that punches above its weight. She expects you to identify where agentic AI workflows (automated approvals, intelligent document generation, AI-assisted reporting, meeting intelligence, workflow orchestration) can replace manual overhead — and where human judgment must remain.

What to produce:

• Document 1: A one-page 30-day operating plan covering how you sequence these five issues, what you tackle in week one, and what you defer and why. Include a specific AI/agentic operations stack recommendation — name at least two tools or workflow automations you would implement first, explain what manual process each one replaces, and why you chose them over alternatives. Be specific about the workflow change, not just the tool name.
• Document 2: A short note (two paragraphs) to the fiscal sponsor's finance team about the vendor approval issue. Acknowledge the gap, propose a specific process, and set a realistic timeline.
• Video: A 6–8 minute video walking the CEO through your plan as a strategic partner — your prioritization logic, what you are protecting her from, where you need her input versus what you will own, and how your AI-first operations approach will give this small team structural leverage.