Chief of Staff & AI-Driven Operations

ClearDesk; San Diego (CA); Remote; USD 150,000 - 210,000; Full time

Job summary

ClearDesk is seeking a Chief of Staff to act as the CEO’s right hand, running the operating system of the company and building AI-powered processes from onboarding to board reporting.

You will lead cross‑functional projects across Sales, Marketing, Recruitment, Training, Client Success, and HR, prototype internal AI tools, and shape how a 500‑person operation uses AI to move fast and stay disciplined.

Qualifications

• Think in first principles, write clearly, and get to the point.
• Built things with LLMs used by real people; can discuss prompts, agents, evals, and integrations.
• Operated in fast-moving companies and own outcomes end to end.
• Low ego, high standards; lead leadership meetings and fix spreadsheets.
• Trusted with finances, people decisions, and strategy; discreet.
• 4–8 years of experience recommended.

Responsibilities

• Own the leadership team’s operating rhythm: weekly leadership meeting, monthly business reviews, quarterly planning, OKR tracking, follow-through on decisions
• Turn the CEO’s priorities into cross-functional projects, then drive them to done across Sales, Marketing, Recruitment, Training, Client Success, and HR
• Prepare briefs, analyses, and decision memos so the CEO walks into every meeting with the picture already clear
• Prototype and ship internal AI tools and automations (Claude, GPT, agent frameworks, no-code/low-code, light scripting) — from CRM hygiene and reporting to client-facing workflows
• Run special projects: new initiatives, partnerships, potential acquisitions, org changes, and anything without an obvious owner
• Be a trusted sounding board and an honest voice — tell the CEO what they need to hear, then help make the plan work
• Potentially take direct oversight of one or more departments as you earn it

Skills

Super sharp

AI builder

A finisher

Low ego, high standards

Trustworthy with sensitive information

4–8 years of experience

Tools

HubSpot

Slack

Asana

Python

JavaScript

Job description

ClearDesk is seeking a Chief of Staff to act as the CEO’s right hand, running the operating system of the company and building AI-powered processes from onboarding to board reporting.

You will lead cross‑functional projects across Sales, Marketing, Recruitment, Training, Client Success, and HR, prototype internal AI tools, and shape how a 500‑person operation uses AI to move fast and stay disciplined.