Chief of Staff & AI Operations Architect

ClearDesk; San Diego (CA); Remote; USD 180,000 - 240,000; Full time

Benefits offered by this job

Benefits included

Job summary

ClearDesk is seeking a high‑impact Chief of Staff to run the company's operating rhythm, translate CEO priorities into cross‑functional projects, and ship AI-powered tooling. You will prototype internal tools, automate repetitive work, and lead strategic initiatives acrossSales, Marketing, Recruitment, Training, Client Success, and HR.

You'll work closely with a multi‑company founder, enjoy genuine authority, and help scale ClearDesk as an incubator with three launched companies and two more

Qualifications

• AI builder with hands-on experience delivering usable tools and workflows
• Experience building with LLMs, prompts, agents, evals and integrations
• Think in first principles and communicate clearly, with strong execution
• Proven ability to own outcomes end to end in fast-moving environments

Responsibilities

• Own leadership team operating rhythm and cross-functional project delivery across departments
• Prototype and ship AI-powered tools and automations
• Prepare briefs and memos for executive decisions
• Help incubate and scale new companies with playbooks and GTM plans
• Drive high-visibility initiatives and strategic partnerships

Skills

AI builder

LLMs опыт

First principles thinking

Generalist

Tools

HubSpot

Slack

Asana

Python/JS

Job description

ClearDesk is seeking a high‑impact Chief of Staff to run the company's operating rhythm, translate CEO priorities into cross‑functional projects, and ship AI-powered tooling. You will prototype internal tools, automate repetitive work, and lead strategic initiatives acrossSales, Marketing, Recruitment, Training, Client Success, and HR.

You'll work closely with a multi‑company founder, enjoy genuine authority, and help scale ClearDesk as an incubator with three launched companies and two more