Chief of Staff

ClearDesk; San Diego (CA); À distance; USD 150 000 - 210 000; Plein temps

Résumé du poste

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.

Responsabilités

• 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

Connaissances

Super sharp

AI builder

A finisher

Low ego, high standards

Trustworthy with sensitive information

4–8 years of experience

Outils

HubSpot

Slack

Asana

Python

JavaScript

Description du poste

About ClearDesk

ClearDesk is a remote staffing company that connects US small and mid‑sized businesses with exceptional talent in the Philippines. We place and manage ~500 Remote Team Members across home care, real estate, bookkeeping, and home services, on a simple flat‑fee model backed by a US leadership team and Philippines‑based operations managers. We're six years in, growing fast, and rebuilding how a staffing company runs when AI is part of every workflow.

The role

You’ll be the CEO’s right hand. That means two jobs at once:

1. Run the operating system of the company.

Own the weekly and quarterly cadence, drive priorities to completion across departments, prepare the CEO for every important decision, and be the person who notices what’s slipping before anyone else does.

2. Build with AI.

We’re not looking for someone who "uses ChatGPT." We want someone who can take a messy process — client onboarding, recruiting pipeline, QBR prep, board reporting — and ship a working AI‑powered version of it in days, not quarters. You’ll prototype internal tools, automate the CEO’s and leadership team’s repetitive work, and set the standard for how the rest of the company adopts AI.

Our current Chief of Staff has done an outstanding job in this seat and set a high bar. You’ll inherit a functioning operating cadence and a leadership team that already trusts the role.

What you’ll actually do

• 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

Who you are

• Super sharp. You think in first principles, write clearly, and get to the point. You’re comfortable being the smartest generalist in most rooms without needing to prove it.
• An AI builder, not a spectator. You’ve built things with LLMs that real people use. You can talk about prompts, agents, evals, and integrations, and you have working examples to show.
• A finisher. You’ve operated in a fast‑moving company (startup, high‑growth SMB, consulting, or founder) and you own outcomes end to end.
• Low ego, high standards. You’re equally good at leading a leadership meeting and fixing a broken spreadsheet at 10 p.m.
• Trustworthy with sensitive information — finances, people decisions, strategy. Discretion is a given.
• 4–8 years of experience is a rough guide; exceptional builders with less will be considered.

Nice to have:

Experience with offshore or distributed teams, staffing/services businesses, HubSpot, Slack, Asana, or light coding (Python/JS).

Why this role

• Direct daily partnership with a multi‑company founder and CEO
• Real authority: you’ll run parts of the company, not just take notes
• A green field to define how a 500‑person staffing operation runs on AI
• A clear path from Chief of Staff into a department head or operating leadership role

Compensation: competitive base + bonus, commensurate with experience. Benefits included.

ClearDesk is an equal opportunity employer.