Welcome to my very first newsletter. Thank you to my early supporters! 🎉

Your Chief of Staff tour of duty is almost done. You’ve got your battle scars, your wounds and your medals to show for it.

You have the trust and the back of your CEO. You’ve led 10 cross-functional initiatives. You’ve helped fundraise while meeting 100s of investors. And you’ve developed your leadership skills massively in your career.

That’s not to say that there haven’t been a few bumps along the road. There have been sticky situations where you’ve had to deal with detractor stakeholders. You’ve had to talk the CEO off a ledge in making a bad business decision. And you’ve had to deal with economic growth uncertainty. It’s 2023 after all.

So what’s next? This is a common coaching question that I get from Chiefs of Staff that are nearing the 2-3 year mark in their position.

What exit opportunities exist for you as a senior Chief of Staff? The answer is many.

✅ Executive Leadership

You take a role on the executive team as a leader of a newly created business unit or function. In the best case scenario, you’ve been already running it after starting it from scratch, so you know the domain area. Plus it’s an important new line of business for the company, otherwise they wouldn’t have invested in it in the first place. You maintain strong ties with your CEO or principal even though you’ve moved on from the Chief of Staff job.

✅ Entrepreneurship

You’re inspired by your CEO and you’re itching to become your own boss. You take some time to pause and reset from your Chief of Staff job to cook up new ideas and test them in the wild before making the jump. Then you launch your company and leverage your connections with investors that you’ve already made while helping fundraise for your current company.

✅ Venture Capital

You love operating, but you want to do it at scale for multiple companies. You land a job at a top VC to implement your knowledge and know-how to their family of startups. Or you’re more attracted to the investment side, given your finance background. You make a case that you have specialized domain knowledge that would make you an exceptional investor.

✅ Private Equity

You love operating, like in the previous example, but you’re not so interested in the startup grind. You're interested in change management and financial engineering. You want a more structured work environment. You join the strategic value creation team at a Private Equity firm that takes you in with open arms because they recognize the operator value you bring to the table.

✅ Management Consulting

You’re more interested in the strategy side of the house and love thinking about hard problems. Top consultancies would kill to have your strategic mind that’s coupled with an operational background. Even better if you have demonstrable sector expertise and professional relationships in an area with low existing coverage.

✅ Another Chief of Staff Job (!?)

You realize, you actually love the Chief of Staff role because you don’t have to deal with the pressures of being #1. But you want a change of pace. So you find your next job through your personal networks which you have developed on the job. Or you join a Talent Network at a Chief of Staff firm, like Cedar, and you work with them to find your next role.

✅ No Exit

Or you take a page out of Sartre’s existentialist masterpiece and you realize, you actually love your role and you love your boss and you love your company. So no, you’re not going anywhere and you’re staying put. You want to deepen your relationship with your boss and continue on your journey with your company.

In sum, when you’re exiting the Chief of Staff job, you’ll have your pick of opportunities to choose from.

So take your time. Get clear on what you actually want. And then go get it. Onwards!

Interested in 1:1 Leadership Coaching?

At Cedar, we are building a small team of executive coaches who help Chiefs of Staff become a high performance leader. We coach folks on topics like upleveling your skills, creating trust with your boss, and of course, deciding on exit opportunities.

👉🏼 Reply to this email if you’re interested in learning more about our 1:1 Leadership Coaching for current Chiefs of Staff.

Building Out My Chief of Staff Job Board

At Cedar, we are constantly talking with CEOs, CXOs, founders and top executives about their Chief of Staff needs. Please stay tuned to this newsletter for a dedicated job board that shows open listings for Chief of Staff and senior operations roles.

PS Are you looking to list your Chief of Staff job post here? Reply to this email if you are a recruiter looking to advertise your Chief of Staff job listings.

Help Us Grow

Our mission is to impact 100,000 top executives and Chiefs of Staff. If this newsletter would help someone in your network understand the Chief of Staff career path and exit opportunities, please forward it to them.

And if someone forwarded this edition to you, please don't leave without hitting that Subscribe button now.

Thanks for reading! Stay tuned for next week’s edition.