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How to manage your CEO

Tactical advice from the Chief of Staff at Helcim, 1 new CoS req we're working on, 3 new CoS job opportunities, and more
 

But First, 3 Shower Thoughts:

  1. People sugarcoat things when you ask for advice because they don’t want to hurt your feelings. But they shouldn’t. Clear (and truthful) is kind.

  2. The more you work on your patterns, the more you see others’ and can empathize more deeply.

  3. We need a new phrase for “net worth” that decouples our colloquial understanding of worth (e.g. inherent value) from financial terms.

 

How to Manage up

This week's issue features a post by Miranda Russell, Chief of Staff at Helcim, a payments company that helps small businesses accept credit cards and save money while they’re getting paid. Miranda shares some tips she has used over her two years as a Chief of Staff to help hold the CEO accountable. 

A few fast facts about our guest writer:


  • Miranda spent 5+ years working for a multinational company with over 10,000 team members before deciding to pivot to a sub-25 people start up

  • She is obsessive about keeping her Peloton streak alive and well 

  • When not working she's embracing her introvert habits and walking her dog, baking, or reading 

  • As an avid reader Miranda aims to complete at least a book a week for a 50+ book reading goal each year 

 

As a Chief of Staff you’re responsible for keeping the organization accountable. The company’s operating cadence and cross department visibility is often a large part of this role. Since you’re already keeping the entire team aligned on shared goals and setting up processes to hold individuals accountable, extending accountability to the CEO should be a natural extension of your role in theory. The reality is that it can be incredibly difficult for a CoS to hold the CEO accountable in the same way they might hold another manager or individual contributor within the organization accountable. This can be due to the dynamic of the relationship, a lack of trust, strong personalities, or simply a lack of processes. CEOs are accountable to a wide range of stakeholders including employees, investors, fellow executives, and themselves. Setting accountability expectations can help elevate the CEO in their role by positioning them as a trusted and reliable leader for the organization. Here are some processes that can be implemented to assist in holding the CEO accountable:

Create regular check-ins


Knowing when you’ll be able to meet with your CEO helps set the operating cadence for the office of the CEO and gives you an opportunity to check in on pending to-do items that are with your CEO. These meetings should be a two way conversation between you and your CEO to pass information and tasks back and forth.

If the meetings are becoming too top-down where information and tasks are only flowing down to you, consider if a reset may be needed. These. check-in meetings are a great time to review tasks in bulk and having designated review time can feel less overwhelming when you’re talking through a document or reviewing a project board vs. sending individual emails for each inquiry.

Set Weekly Priorities

This should be done as a part of your regular weekly check-ins. If you have multiple check-ins per week (for example I meet with my CEO on Mon/Wed/Fri) use the first meeting of the week to confirm both of your priorities and top of mind items for the week. Any unaddressed agenda items and tasks that are being carried forward should also be reviewed to confirm if the priority has shifted.

Set up recurring retros as part of your operating cadence

The office of the CEO is not exempt from completing project retros. At the end of the quarter or on a cadence that makes sense for your organization, be sure to review what was completed in the last quarter and how that work aligns with the company goals. Were there items that never ended up being addressed? Dig into why that was - were they no longer the priority, was there just not enough time to get to them? And what was the impact of these items not getting done.

Manage your to-do list AND theirs

A never ending to-do list is a common trait for a CoS and for a CEO. You should have visibility into what your CEO is working on, due dates, and priorities. Ideally you have a project management tool that can help manage this.

At Helcim, we have created project boards for each team including the Executive Team and the expectation is that everyone, including the CEO, enters their tasks to track and report on their current work.

Use 1:1’s to share feedback both ways

If you were dropping the ball on projects or missing deadlines you better believe you’re going to hear about it during your 1:1 with your CEO. If the places are reversed and your CEO has missed deadlines or failed to follow through on key tasks, you can use the 1:1 to share this feedback in a candid manner.

Tie your feedback to the impact it has on the organization, when tasks are missed or dropped by the CEO do you see the impact in team morale, is the team less aligned on what the top priorities are, is there a waterfall effect on other teams who were waiting for the information or guidance?

Speak up in the moment

One of the hardest things to do in the CoS role can be to contradict the CEO in the moment. However, to hold them accountable, it is often easiest to resurface information or share a reminder immediately if a discussion is pointing to an accountability issue.

For example, if the CEO is overcommitting to projects, taking on tasks that should not be their responsibility, or committing to attend or participate in events that you know will cause conflicts. These are all times you need to surface the potential conflict so you can discuss the issue and keep the CEO accountable to their commitments.

Even with all these processes priorities are going to change, conflicts will arise, and deadlines will slip, that is part of the fluid nature of working in the CoS and CEO partnership and that’s okay. As you build your relationship with your CEO and find effective ways to hold them accountable to their many stakeholders you will help elevate them in their leadership position by building trust in all those who report to them and work with them on a regular basis.


 

Search Spotlight


Chief of Staff @ Legal Tech Startup

Our client is a late-stage legal tech startup revolutionizing the legal sector through innovative, cloud-based solutions that empower legal professionals to excel in managing their practices and serving clients effectively.

Role Summary: The Chief of Staff will play a crucial role in enhancing the executive team's efficiency by directly supporting the CEO in strategic project execution and decision-making. This position involves working closely with senior leadership to solve problems proactively, and carry out a variety of strategic initiatives tailored to the CEO's priorities.

Key Responsibilities:

  • Collaborate closely with the CEO to drive key projects and strategic initiatives.

  • Enhance internal operations for maximum efficiency and effectiveness.

  • Lead project management efforts, ensuring alignment and execution across teams.

This role might not be for you if:

  • You want a strategic role vs being hands on and in the weeds

  • You aren’t excited about being in-office 5x/week

  • You want to work 9am-5pm

We're looking for candidates with a truly relentless work ethic to complement that of the founder they would be partnering with, and the highly structured systems-thinking and analytical rigor to match.

Ideal candidates will have 5-10 years of experience overall with management consulting and SaaS startup experience. MBA preferred.

What They Offer: 💰 Top of market compensation (base salary + bonus + significant equity) ⚕️Medical, dental, vision, and disability insurance 👨‍👩‍👧 Maternity and paternity leave 🎉 Additional benefits 📍 5x/week onsite in Salt Lake City

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!

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

Job Opps

🔀 Chief of Staff at Poggio — automating enterprise sales workflows

My thoughts: Poggio is remote first! I wrote recently how these aren’t a ton of remote CoS roles, but there are exceptions like this one. Adding some of these market observations here:


• 100% remote roles are far and few in between (~ <5% of open roles) • Competition for them is fiercer than ever (1000+ applicants in 48 hrs) • Employers want their CoS hybrid or fully onsite (in person 3-5x/week) • Employers want people with CoS experience already (1-2 years)

The CoS at Poggio will drive internal and external processes for the business, sales, growth, and customer acquisition initiatives, and special projects.

Ideal candidates swill have experience building financial and operating models driving highly complex and cross functional initiatives from 0→1. Nice-to-haves include exp with data analysis, including using BI tools and SQL.

💰 Salary: Not listed but given the finance/analytical skills it’s probably in the mid 100s+

📍 This role is remote.

📥 Apply here.

📊 Chief of Staff at Alembic Technologies - marketing event conversion and correlation engine

My thoughts: Alembic examines data streams, including web, social media, and broadcast, along with sales data, to detect 'signals' within omnichannel marketing and sales efforts, which are then linked to conversions and revenue, providing insight into the factors contributing to revenue generation.

They count NVIDIA as a customer and raised a $14 million Series A last month.

I absolutely love when JD’s include what the role is not. Alembic says this Chief of Staff role isn’t

  • just a stepping stone

  • a glorified assistant (hooray!)

  • defined by clear cut objectives

Rather, the CoS will lead strategic initiatives, create and streamline processes, and develop and track KPIs, along with owning special projects end-to-end.

📍 This role is onsite in San Francisco.

📥 Apply here.

👐 Chief of Staff, Growth Markets at Paypal — the faster, safer way to send & receive money

My thoughts: They’re a mixed bag on this one!

What I love is that they acknowledge that the “confidence gap” and “imposter syndrome” affect the types of applicants they get. What they’re referencing here is that, oftentimes, women will not apply to a role if they’re not 100% qualified (whereas men will apply if they think they meet ~50% of the requirements). Kudos, PayPal.

They’re looking for a Chief of Staff with to work closely with the General Manager of Growth Markets to drive strategic plan execution, optimize organizational routines, and manage critical initiatives.

Ideal candidates will have 3-5+ YoE in strategy consulting or product strategy, strong quantitative and analytical acumen, and experience “selling, supporting, and implementing E-commerce payment services”.


💰 Salary: The JD states “The U.S. national annual pay range for this role is $52,800 to $136,510” ….😔. While this might be factually true, it’s irrelevant for this role. Here’s compensation data from Carta based on a Director of Ops role in San Jose, CA which is a reasonable comparison with respect to leveling/seniority (and keep in mind this is for a startup valued at $1-10B while PayPal’s market cap is ~$67B):

This checks out^

📍 This role is based in San Jose, CA.

📥 Apply here.


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