Chief of Staff

Chief of Staff to the CEO

ClearDesk · San Diego (North County) · Full-time, in-office

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.

We're also more than one company now. In September 2026 we launched three new businesses that we incubated inside ClearDesk — each built on our talent, operations, and AI playbook. In 2027 we're formalizing that into a proper incubator, with two more companies slated to launch next year. The Chief of Staff sits at the center of all of it.

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 — across ClearDesk and the companies we're incubating.

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 (and each new company we launch) 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

Help run the incubator: support the three companies we launched in September, build the playbook for how we stand up a new company (entity, team, systems, go-to-market), and help launch the two companies on deck for 2027

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 — or an operating role in one of the incubated companies — 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.

Energized by zero-to-one. You like the ambiguity of a brand-new company as much as the discipline of running an established one.

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, launching or operating early-stage companies, 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 front-row seat — and a hand on the wheel — as we turn ClearDesk into an incubator: three companies launched, two more coming in 2027

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, an operating leadership role, or a leadership seat in one of the companies we launch

How to apply

Send us three things:

Your resume or LinkedIn

One example of something you built with AI (a link, a Loom, or a short write-up) — what problem it solved and what happened

A short note (under 200 words) on what you'd change about ClearDesk after 90 days, based on what you can learn from the outside

EMAIL ALL THIS TO View email address on click.appcast.io

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

ClearDesk is an equal opportunity employer.