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What kind of Pokémon is a Chief of Staff? (Plus 3 new Chief of Staff jobs)

Why a Chief of Staff is a Psychic/Steel type, Chief of Staff SparkNotes by Dan Glenn (CoS @ GoodLeap), a new Chiefly episode, CoS to CEO @ a CPG startup, and more


But First, 3 Shower Thoughts:

  1. LinkedIn News has the pithiest headlines on the entire internet.

  2. Use a North Star (and intuition) to guide your decision-making.

  3. The 90s band Creed is making an epic comeback and I’m here for it.


And a new Chiefly episode!

Before we dive in, I wanted to share that a new episode of the Chiefly podcast just dropped!

This one’s with Ashley Burgio, COO at DayTwo. We did a deep dive on her transition from Chief of Staff to COO, key skills she learned on the job, why Chiefs of Staff have to find “the mess”, and more.

Check it out here!


Chief of Staff SparkNotes

Today’s stream of consciousness and SparkNotes-esque post is in collaboration with Dan Glenn, Chief of Staff at GoodLeap, a sustainability fintech that has raised $800M by notable investors including Brookfield, WestCap, NEA, and Mubadala Investment Company.

First, what is a Chief of Staff? They’re a strategic advisor and right-hand to a leader, and help drive communication, collaboration, and decision-making velocity across the executive team.

In a few words, they’re also:

  • A professional juggler/fire fighter/Rubik’s Cube Officer

  • One part psychologist & psychiatrist, and one part ultimate hype person

The Chief of Staff position is a critical component of the organizational brain stem, but the role also varies wildly between a number of possible levels.

These levels include the following:

  • EA+ — The most basic form. A high-powered administrator/logistician who carries out priorities as defined by others.

  • Air Traffic Controller — Knows every where/when/why and is a master logistician, coordinating many team members and executives, and crucially…prioritizing them.

  • Junior Executive — All the above, but also trusted with various special projects or even business units. Capable of running key meetings with or without the supported executive.

  • CEO Avatar — A fully trusted and fully-formed Chief of Staff that runs projects, solves problems, and coordinates between multiple or all executives and their departments. To a limited degree, empowered to speak on behalf of the CEO.

To be effective, a Chief of Staff must be confident and competent as a baseline, but more so than anything else, one must be completely trusted as an honest broker to truly succeed.

You also must be able to be strategic and prioritize! You will spend your day fighting reactivity in favor of proactivity.

At a tactical level, a Chief of Staff should be punctual, organized, a capable thinker, and calm.

At the very least, the responsibilities are broad, challenges significant, and the strain severe, hence the short shelf life of the position: typically 18-24 months but rarely longer than 36 months.

A committed Chief of Staff will spend many days as first in, last out, often splitting this distinction with the Founder/CEO themselves.

The role is not for the faint of heart, as you will spend your days playing chess against masters of the game, debating against some of the most persuasive and strong-willed people in the world... because as may often be the case, you spend as much time locking horns with your own team as you do with others.

One of the most difficult aspects is the requirement to make someone else’s life and interest at the center of your own. Do not underestimate how challenging this can be.

To be successful in the role, practice these phrases:

  • “Which alligator is closest to the boat?”

  • “Is this the best use of our time?”

  • “Let me take care of that” and “Let me take that off your plate”

  • “What can I help with?”

  • Strive to say...“That’s already done.”

The Chief of Staff Pokémon (Strategemon?!)

If a Chief of Staff were a Pokémon, they’d represent a blend of intellectual foresight, raw horsepower, and the resilience required to stay cool in high stakes environments. Let’s call it Strategemon 👾. Here’s what this Pokémon might look like:


  • Psychic/Steel (see: ability to see around corners, and nerves of steel!)

Key Abilities

  • Foresight: This ability allows Strategemon to predict opponent moves several turns ahead, giving it a tactical advantage in battles, mirroring a Chief of Staff's need to anticipate future challenges and prepare accordingly.

  • Execute: Lets Strategemon analyze the battlefield or any environment in real-time, identifying the most efficient and effective course of action. Once a plan is in place, Execute ensures that every move is carried out with meticulous precision, maximizing the impact of each action towards achieving the strategic goal.

  • Telepathy: Strategemon can seamlessly coordinate its allies in battle without the need for verbal communication, symbolizing a Chief of Staff's ability to keep teams aligned and focused on common goals.

  • Time Bend: This rare power allows Strategemon to manipulate short bursts of time, effectively multitasking or speeding up its actions. It represents the Chief of Staff's skill in managing multiple work streams simultaneously and prioritizing tasks efficiently.

Signature Move

  • Harmonize : Strategemon emits a harmonizing frequency that boosts the morale and performance of its allies, akin to a Chief of Staff's role in fostering a positive, productive team environment and being the culture standard bearer of an organization.


  • Overload: When faced with too many attacks simultaneously, Strategemon's reaction time slows down, a nod to the risk of burnout in a high-pressure Chief of Staff role.

  • Isolation: If Strategemon is isolated from its team, its effectiveness decreases significantly. This highlights the core aspect of teamwork and collaboration for a Chief of Staff, which is key to their ability to thrive long-term.

Ideal Habitat

Strategemon thrives in environments that challenge its strategic and intellectual capabilities, like complex battlefields where it can continually adapt and grow

Compatibility with Other Pokémon

Strategemon works best in tandem with Pokémon (Principals) that need help executing and have complementary key abilities.

Search Spotlight

Chief of Staff @ Bootstrapped CPG Startup

This CPG startup is building the next big deodorant brand in the US 😍 Founded on the principles of science-backed ingredients and customer-centric product development, our client's products offer safe, reliable, and convenient options for managing sweating and help people gain confidence and comfort in their daily lives. The company is hiring a Chief of Staff who will be heavily focused on: • Brand development • Supply chain optimization • Business operations Ideal candidates will have 3-4 years of professional work experience and a minimum of 1-2 years of experience in operations at a CPG startup. Additional key details: 💰 $120k+ base salary 📍 This role is remote

If you're interested and want to learn more about the company, just apply here! I’ll get back to you ASAP if your experience aligns with what they’re looking for.

Know someone who could be a fit for this role? Feel free to share this blog post!

Other Right Hand Talent searches:

Check out our job board for the full list of opportunities with our clients!

Know someone who could be a fit for this role? Feel free to share this blog post!

Job Opps

👶🏼 Chief of Staff at Patch Caregiving — childcare benefits for frontline workers

Why I like it: Founded by Stanford MBA alum Sarah Alexander, Patch Caregiving emerged from a mission to address childcare instability for shift-based workers, spurred by the realities of the Covid pandemic, e.g. how hard it is for lower-income employees to get childcare and how much the world relies on “frontline” workers.

Patch Caregiving is looking to bring on a Chief of Staff to the co-CEOs to lead strategic relationships, ow a portfolio of customers, and lead financial analysis to inform key business decisions.

The top skills and experience they’re looking for are 3+ years of experience in management consulting, banking, venture capital, or a comparable role at a high-growth start-up, as well as experience with deck-building and comfort with data analysis in Excel.

📍 This role is remote.

📥 Apply here.

🙏 Chief of Staff at Monument — virtual alcohol treatment

Why I like it: The low/no-alcohol movement started gaining steam a few years back and it shows no signs of stopping. More and more people are giving up alcohol to lead healthier lives, but it can be challenging to take a step back from alcohol when every social meetup is seemingly centered around its consumption.

Enter Monument — an online platform that helps people change their relationship with alcohol. Monument partners with employers to offer virtual alcohol treatment, including community-based peer support, therapy and physician care.

They’re looking for a Chief of Staff to help provide operational support, optimize processes, assist with strategic planning, and rovide analytical support for decision-making.

Ideally, candidates will have 6+ years of experience in GTM operations, bizops, project management, management consulting, or strategic roles in a fast-growing company.

💰 Annual salary is scoped at $155,000 – 175,000.

📍 This role is hybrid in NYC (3x/week).

📥 Apply here.

🏢 Chief of Staff at Apartment List — helping you find the perfect apartment

Why I like it: The role reports to the COO. You don’t see a ton of these in the wild, so it’s an amazing opportunity to help run (as they describe) “one of the most robust and complex organizations” within the company.

And I’m not surprised to see “communication proxy” and setting the “business rhythm” ranking high on the list of responsibilities for the Chief of Staff because these are the sorts of critical needs that bigger organizations have, which are a side effect of more headcount, more teams, and increased complexity overall.

According to the job description, ideal Chief of Staff candidates have proven experience in management consulting, bizops, or strategic planning, with a track record of critical thinking and problem-solving. Apartment List also values strong business acumen and a data-driven approach to decision-making.

💰 Pay is $112,000 - $155,000 + variable compensation + equity, but this is listed as a contract role on LinkedIn (I assume that variable + equity are part of total comp if you convert to a W2 employee).

📍 This role is remote.

📥 Apply here.

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My Bookmarks on X

  • George, a self-taught engineer, shares what really goes on above the IC level at tech companies

  • As your seniority increases, your real job is to disagree with people

  • Sam Altman seeks to raise more than the entire GDP of Japan for his new venture

  • Major VC firms are coming under fire for allegedly funding Chinese tech companies that are linked to Beijing’s military

  • Tucker Carlson interviewed Putin and memes abound re the Russian President answering basic questions with long-winded history lessons


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