Chief of Staff to a Managing Partner (Remote, North America)

Full-time contractor · $4,000 to $7,000 USD/month depending on experience · Pacific Time hours · Remote (US, Canada or Mexico)

I run two things in parallel: a real estate fund manager (McKay Capital, ~1,000 multifamily units in Washington state, four closed funds, a fifth in preparation) and a growth organization inside Microsoft. The Microsoft side has its own executive assistant. McKay Capital and my personal operating system do not have anyone driving follow-through. That is this role.

You will work directly with me, with my co-GP, and with a four-person operating team (operations, maintenance, accounting, engineering). You will spend most of your day inside Claude Code against a markdown knowledge base, a Todoist instance, AppFolio and QuickBooks, and Google Workspace. If you have not used an LLM as your primary work tool for at least six months, this is not the right role.

What you will own

• Operating cadence for McKay Capital. Run the weekly and monthly rhythm: agendas, action items, follow-ups with the partners, and the overdue-item list. Success: nothing I delegated three weeks ago surprises me by still being open.
• Decision memos. Turn a messy thread (a refinance question, a budget variance, a vendor dispute) into a one-page memo with a recommendation. I read it, decide, you execute.
• Fund and investor workstreams. Track the refinance calendar, capital calls, distributions, LP memo deadlines, and budget reviews to completion. Draft first versions; the co-GP and I finalize.
• Personal operating system. Keep the task system honest: triage, estimate, reschedule, close. Coordinate with the Microsoft EA so the two calendars and task lists agree. Run household projects and the family social calendar.
• Build, not just operate. When you do something twice, automate it: a Claude skill, a script, a sheet that fills itself. You will have a code repo and a senior engineer to lean on.

What we are looking for

• Two to six years in consulting, startup operations, or a chief-of-staff or program role where you owned outcomes, not tasks
• Daily, fluent use of Claude or ChatGPT for real work; you can show a transcript and explain your prompting choices
• Written English good enough to send to an investor without my editing it
• Comfortable with spreadsheets and basic financial statements (P&L, balance sheet, DSCR); real estate background not required
• Based in the US, Canada or Mexico, available 8am to 4pm Pacific
• Spanish is useful for some vendor work but not required

What this is not

Not an executive assistant role. Not a travel or inbox job. Not part-time. It is a long-term remote contractor relationship paid through Deel.

How to apply

No cover letter needed. Answer the three screening questions with your application:

• Describe a system you built that still runs without you. One paragraph.
• Paste the last prompt you sent an LLM for real work, and the output, with any edits you made before using it.
• Your monthly rate in USD and your earliest start date.

Shortlisted candidates receive a paid take-home, then a one-hour working session, then a two-week paid trial.

Pay: $4,000.00 - $7,000.00 per month

Application Question(s)

• Describe a system you built that still runs without you. One paragraph.
• Paste the last prompt you sent an LLM for real work, and the output, with any edits you made before using it.
• Your monthly rate in USD and your earliest start date.

Work Location: Remote