Chief of Staff

We are two founders building businesses, brands, and a life together, and we are looking for a Chief of Staff who can take recurring work off our plates and run it without us in the loop.

This is not a traditional Executive Assistant role, and it is not purely a business operations role.

You will work closely with both of us across business priorities, content, growth initiatives, personal logistics, travel, appointments, projects, and the dozens of things that come with building companies while still protecting time for life outside of them.

Your job is not simply to execute what we ask.

Your job is to understand what we are trying to accomplish, anticipate what needs to happen next, and take ownership of moving things forward without waiting for detailed instructions.

We work asynchronously. We will not always be available to answer questions in real time, and the role is built so that we do not have to be.

The Standard (Read This Before Anything Else)

Two behaviors decide whether this works. If either is missing, this is not the role for you.

• You drive through obstacles instead of routing around them silently. If the plan was to call and you cannot get through, you find another way or you tell us, before quietly switching to something worse and hoping it is fine.
• You escalate contradictions, you do not resolve them against us. If someone gives you information that conflicts with what we told you, you bring it back to us in one line and let us decide. You do not silently take their word over ours.

What Success Looks Like

You make both founders easier to operate.

You know what is happening across the businesses and our personal priorities, and you keep the important things moving.

You notice things before we do.

You follow something through to completion rather than simply completing your portion of it.

When one of us gives you an objective, you think through the next two or three steps instead of waiting for each one to be assigned.

You understand when something requires one of us and when you can simply handle it.

Over time, more things happen without our involvement because you own them.

The goal is not to keep a better task list. The goal is to make sure things happen.

1. Recurring Execution and Reporting (Day-One Priority)

This is the core of the role at the start.

• Run our recurring reports and send us finished output, not raw work to review
• Own repeatable workflows end to end once they are handed off
• Turn anything we do more than once into a documented SOP so it never needs us again
• Keep everything captured and tracked in ClickUp

2. Priorities and Follow-Through

• Managing priorities and commitments
• Tracking important projects and follow-ups
• Protecting founder time
• Identifying bottlenecks
• Following up with people without being asked
• Making sure decisions turn into action
• Recognizing when something is stalled and moving it forward on your own initiative

3. Inbox and Communication

Nothing should sit. Everything should progress.

• Organizing and managing the inbox
• Flagging priority items
• Drafting responses and keeping conversations moving
• Ensuring timely follow-up across all threads
• Communicating on our behalf where appropriate, in English or Spanish depending on the recipient

4. Brand, Content, and Growth Operations

Both founders are building founder-led brands, and you will help create the operating system behind them.

• Content planning, scheduling, and distribution
• Short-form video and social media workflows across LinkedIn, Instagram, TikTok, and YouTube
• Podcast or guest coordination, production, and publishing where relevant
• Audience growth
• Newsletter and email initiatives
• Partnership research and outreach

You do not need to be the expert at everything. You need to learn the process, coordinate resources, use technology and AI, and make sure execution happens consistently.

5. Revenue Support

We expect this person to care about growth, not just administration.

• Research prospects and opportunities
• Manage and track LinkedIn outreach
• Maintain accurate, organized lead lists and a clean CRM
• Execute outreach and manage follow-up
• Coordinate sales activity
• Identify areas where better execution could create revenue

6. Personal and Family Operations

Our personal and business lives are not managed in separate worlds. You will help us manage both.

• Personal appointments and calendar coordination
• Travel planning (flights, hotels, itineraries)
• Reservations
• Household contractors and service providers
• Research and purchasing
• Family and school logistics
• Gifts and important dates
• Follow-up with service providers

7. Systems and Automation

We do not want to solve the same problem repeatedly. Part of your responsibility is recognizing when something should become a system.

• Build and improve workflows
• Create simple SOPs
• Improve our use of ClickUp and other tools
• Identify opportunities for automation
• Use AI extensively in your work
• Research and implement new tools

Requirements

Type: Full-Time

Location: Remote

Language: Fluent English and Spanish

Hours: Full working-day coverage on an async basis. No standing meetings required.

Compensation: $1,000 to $1,200 USD per month

Reliable internet - we provide the software but you need to have your own computer and headphones