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The first 30 days and "breakeven point" for a Chief of Staff (plus 3 new Chief of Staff jobs)

Plus a framework for identifying the types of communicators at work and one new Chief of Staff req we're working on

Hello, and welcome to the Right Hand Talent newsletter! I’m Zaharo, and I write about all things Chief of Staff, talent, and career excellence.

Every week, you’ll get 3 new CoS jobs that are on my radar, reqs we’re working on, my thoughts on growing in the CoS role and as a professional, top stories I’m following on X, and more.

  1. Saying “no” to things is a very, very hard skill for founders to learn.

  2. Letting go of the reigns is hard, too.

  3. If your colleagues are parents of very young children, send them virtual hugs because they probably haven’t slept well in years!

What is the "breakeven point"?

One of my favorite concepts from Michael Watkins’ book The First 90 Days is the “breakeven point” of a new hire, or the point in time where the value they've consumed = the value they've created (and net contribution = 0). After this point in time, you’re expected to be contributing net positive value to the organization.

Note that the point at which the new hire is expected to switch from consuming value to creating value is at the 90-day mark, but I think the expectation for a Director/Sr. Director or more senior Chief of Staff is much sooner than this, likely within the first 30 days. Getting up to speed FAST is the basically a requirement of the job. In the same vein, I wouldn’t think that things are going well if your breakeven point is 6 months (!).

For Chiefs of Staff, it’s very often the case where during the first 30 days you’re more focused on your Principal’s immediate needs -- such as taking tasks off their plate that don't necessarily have goals attached to them except for "get it done" -- but eventually you’ll need more structure with concrete OKRs so that you’re aligned, goaled, and evaluated appropriately.

And while Principals have a good idea of what success looks like for major initiatives, OKR crafting itself should be a collaborative process between your Principal and you, where you are actually taking on the brunt of the detailed work involved in defining scope, scale, timelines, and metrics.

The graph above illustrates the reason why Principal’s should share basically everything with their Chief of Staff to give them as much context as possible. The faster and more thoroughly they do this, the fewer roadblocks you’ll have and the faster you can reach your breakeven point.

The first 30 days — assess and align, but get your quick wins locked in

If you only saw the tip of the iceberg during the interview process, this is when you go below the surface to assess and get a deep understanding of the organization's culture, what drives key stakeholders’ agendas/projects, and how the business is run.

Ideally, your Principal is also using this time to give you the background on the executive team. When you have full context, you can build relationships more effectively and in turn, be a more effective Chief of Staff.

At minimum, your Principal should tell you about the executive team’s:

  • Genesis. Are there prior existing relationships? How did the team come together? This will inform how you approach each executive and leverage relationships for greater influence and better governance.

  • History. Has there been significant conflict in the past, or has conflict been escalating? Is there bad blood between anyone? Awareness of any past conflicts or tensions within the team ensures you aren’t blindsided and can help you anticipate when, where, and how to mediate.

  • Weak spots. What are the team's strengths & weaknesses? Knowing this means you can strategically support where necessary.

All told, think of it like a game of Sid Meier’s Civilization — you’re trying to understand the landscape and players' motivations to help you achieve & succeed in the end (though hopefully through diplomacy and not domination😂 IYKYK).

I’ll use any excuse to plug a gaming gif!

At the same time, it's essential to get aligned with your Principal. Discussions should focus on defining success for your role and setting short-term goals that contribute to long-term objectives. On a tactical level, you may use this checklist as part of your first 30 days of onboarding:

  • Meet each member of the executive team

  • Understand their vision, priorities, and expectations

  • Establish communication preferences (know what kind of communicator you’re working with! See the flowchart below to figure this out :)

  • Get acquainted with the organization

  • Meet department heads and key personnel

  • Understand departmental goals, challenges, and current projects

  • Review current strategies, OKRs, and KPIs

  • Assess alignment with the company's overall objectives

  • Identify areas for improvement

  • Evaluate existing processes, tools, and communication channels

  • Familiarize yourself with the company culture and values

Finally, you have to identify quick wins in the first 30 days. This is low-hanging fruit that can help you gain credibility and demonstrate your value early on. As a Chief of Staff, these could range from improving communication flows between departments to jumpstarting a stalled project.

The key here is to choose initiatives that are visible, valuable, and achievable within a short time frame. Quick wins are a double whammy because you’ll reach breakeven faster and you’ll build your reputation. And your Principal should be 100% on board with you getting quick wins and even point some of them out to you. They need you to “influence without authority”, but frankly, they play a really important part in setting you up to do so successfully.

Importantly, the quick wins should be visible across the executive team because that’s who you’ll be needing to establish street cred with — it’s not just your Principal but others’ buy-in, support, and influence that you’ll need to accomplish the cross-functional initiatives that you’ve undoubtedly been hired to lead as Chief of Staff.

Chief of Staff @ Bootstrapped CPG Startup

Our client is one of the fastest growing functional food & beverage brands of the past decade 😍

They're looking for a Chief of Staff to drive key projects and business priorities by providing insights, feedback, and support for all parts of the business from ideation to execution.

𝗞𝗲𝘆 𝗿𝗲𝘀𝗽𝗼𝗻𝘀𝗶𝗯𝗶𝗹𝗶𝘁𝗶𝗲𝘀 𝗶𝗻𝗰𝗹𝘂𝗱𝗲:

• Assisting in the prioritization of our COO/CFO’s responsibilities

• Sitting in on meetings with leadership, advisors, and key partners with the goal of extracting, recording, and executing on pertinent information

• Driving strategic business initiatives and managing the lifecycle of projects from development to execution

• Facilitating strategic decision-making and program management, ensuring effective communication throughout the process


• Understanding of financial principles, including budgeting and planning

• General understanding of the CPG space and CPG lifecycle (Development, Introduction, Growth, Maturity)

• Experience in organizing, directing and executing across multiple teams and departments, with a strong communication skills

• Experience in planning and leading strategic initiatives

𝗔𝗱𝗱𝗶𝘁𝗶𝗼𝗻𝗮𝗹 𝗸𝗲𝘆 𝗱𝗲𝘁𝗮𝗶𝗹𝘀:

💰 $130-150k+ & equity commensurate with 75th percentile of market for role

⚕️ 75% of healthcare, dental, and vision coverage

🤸‍♂️ Monthly gym and health reimbursement 

📚 1 book per month reimbursement

🌴 Unlimited PTO

📍 Hybrid office culture in Austin with flexibility

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.

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

🥷 Chief of Staff at Stealth — ???

My thoughts: I’m not surprised to see a healthtech company post a job under “stealth”. We’re running a few searches for healthtech companies right now and the industry is small, competition for talent is fierce, and at the same time, founders don’t want to step on other founders’ toes so avoid poaching.

From the JD: The Chief of Staff will..

  • Partner with the CEO to develop and execute strategic plans, prioritizing initiatives and setting clear goals for success.

  • Oversee key projects and initiatives, fostering collaboration across departments and ensuring timely completion.

  • Lead executive team meetings, managing agendas, action items, and follow-through.

Things that jump out at me about the ideal candidate:

  • Preference for healthcare tech experience + knowledge (same goes for our other clients)

  • Early career (only 2+ YoE required)

The thing to remember with these kinds of preferences and “bonus points” is that, as an applicant, you may very well meet every single bullet point in the JD, but you will likely be edged out by someone with healthtech experience.

A lot of the times the way things go with hiring processes is certain qualities start out as preferences and very quickly become requirements. It can take as little as a single candidate interview with someone who has healthtech experience to set the bar for the rest of the process.

💰 Salary: Up to $70k/year. Makes sense considering junior leveling + geo.

📍 This role is hybrid in Dallas, TX.

📥 Apply here.

🏀 Chief of Staff to CRO at Dallas Mavericks

My thoughts: “My next guest needs no introduction”. What an opportunity for the sports and NBA fanatics and out there!

From the JD: The Chief of Staff will..

  • Work closely with the CRO on implementing pivotal day-to-day priorities as well as cultivating strategic initiatives across sales, marketing, arena operations, business operations and business development.

  • Serve as a resource and sounding board to the CRO to provide an objective, independent perspective on ideas and issues impacting the organization

  • Engage with and facilitate optimization of the cross-departmental and organizational initiatives of the ELT

Things that jump out at me about the ideal candidate:

  • Ability to manage up and be a good sounding board

  • Emotional intelligence + maturity

  • Ability to influence across multiple levels

For more senior candidates, it usually comes down to the EQ and how well they hit it off with their Principal in these final stages. Everyone who gets to the end of a process is likely great at all the hard skills they’re looking for, it’s just the connection could be stronger with one candidate over another.

💰 Salary: Likely high 100s.

📍 This role is based in Dallas, TX.

📥 Apply here.

💼 Chief of Staff at Misen — cool cooking tools

My thoughts: I love their name, which comes from ‘mise en place’ — a culinary term that means “to put in place.” Also, their JD is short and sweet and is one of the best ones I’ve seen for this role.

From the JD: The Chief of Staff will focus on…

  • Own resource allocation including people, capital, and time.

  • Participate in strategic decision making as an equal partner. This is unlike most Chief of Staff roles and a critical part of who we are, leading to pull VS push management.

  • Drive digital improvements in both frontend and backend processes.

Things that jump out at me about the ideal candidate:

  • 1-3 years in a strategy role at MBB or similar tackling a variety of subjects.

  • 1+ years of experience directly or indirectly managing multidisciplinary teams supporting a consumer brand with omnichannel distribution

  • 1+ years contributing strategy, GTM, or implementation with a finance, sales, or marketing focus driving $50M+ in annual revenue.

  • To be fun and a good human being.

💰 Salary: $122-174k; solid range.

📍 This role is fully remote.

📥 Apply here.


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