How I "Buy Back My Time" with a Chief of Staff

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Not all remote businesses are created equal. One model might require more (or less) than another.

MaidThis is a perfect example.

MaidThis is the first-ever national vacation rental cleaning franchise and focuses on both residential and Airbnb cleaning.

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(Seriously, the founder Neel, traveled to 50+ countries while building his own location).

MaidThis has been on a tear, expanding to 20 locations, so if you want a territory, check it out soon!

Exactly 40 days ago, I hired my first Chief of Staff. For the sake of this newsletter, I will refer to her as “Kayla”.

Here is part of the job description I used to search for Kayla:

“Job Description

As the Chief of Staff at Greenbox Storage, you will play a pivotal role in supporting our startup's growth by being a dynamic team player and assisting various departments such as marketing, operations, and employee management. This is very much a dynamic position.

Reporting directly to the CEO, you will contribute to the strategic direction of the company, ensuring efficient collaboration and coordination across all functions.

• Team Collaboration: Act as a dynamic team player, working closely with departments including marketing, operations, and management to facilitate seamless communication and cooperation.

• Strategic Support: Provide crucial support to the CEO in the development and execution of strategic initiatives that drive the success of Greenbox Storage.

• Cross-Functional Assistance: Assist various departments with a hands-on approach, addressing challenges, and contributing to the overall success of the startup.

• Operational Coordination: Coordinate and streamline operational processes to enhance efficiency, supporting the startup's objectives and goals.

• Reporting and Communication: Report directly to the CEO, providing regular updates on key initiatives, projects, and operational matters. Prepare executive-level communications and reports.

• Start-Up Mentality: Embrace a startup mentality by being adaptable, proactive, and ready to take on diverse responsibilities to contribute to the growth and success of Greenbox Storage.”

47 people applied for this position. After interviewing about 5, I settled on Kayla. She’s from the Philippines and has solid experience in operational roles.

When going through the interview process, I sometimes get a feeling when talking to someone. This feeling put into words is, “Without question, I 100% want this person on my team. I have no doubts whatsoever.”

I had this feeling with Kayla. After her final interview, I sent her a job offer. Two days later was her first day as a Greenbox Storage employee.

How my Chief of Staff saves me time

One of the first days I hired Kayla, she presented me with this plan. She’s so good, she took the initiative to make her own 90-day plan without any guidance.

• Days 1-30: Become an extension of the way Collin thinks

• Days 31-60: Become an extension of the way Collin behaves (Ready and proactively share alternative solutions, and suggestions)

• Days 61-90: Become an extension of the way Collin makes decisions (Be ready to make decisions in case Collin is not around - what would he say? What would he answer? What would he suggest?)

I was blown away when she shared her plan with me. I’d never hired a Chief of Staff before, so I didn’t really have a plan / structure for her.

The 90-day plan above sounds good on paper, but how is it actually working out?

It’s working out even better than I’d thought. Kayla has earned significant trust in only 40 days. Any small - medium size tasks that I need to complete, I delegate to her.

She frees me to work on major projects and think about the “big picture”.

If you haven’t hired an Executive Assistant or Chief of Staff yet, I highly recommend it.

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Cheers,

Collin Rutherford

PS. Crypto bros 😤