How To Get A Chief of Staff Role In 2026: 6 Job Search Tips
In this A Chief of Staff podcast episode, David Nebinski shares six Chief of Staff job searching tips if you are looking for a new job in 2026. You will learn how to stand-out in a crowded and tough job market. You can do it!
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FULL VIDEO
You can watch the full video of this podcast episode here!
6 Chief of Staff Job Search Tips in 2026
Look for a company trigger moment like a fundraising announcement
Look for off-market roles on Twitter, in group chats, through peers, etc
Lean into your strengths and figure out your positioning and messaging. Create a 1-2 sentence summary of what you are looking for and tell everyone you can the same thing.
Add-value to Founders by trying to help them grow their company by making introductions, sharing people looking for roles, trying their product, etc
Attract inbound interest by posting content online about the Chief of Staff role and your experiences and / or being a guest on A Chief of Staff podcast :)
Connect with Chief of Staff community builders and content creators online and in-person at my A Chief of Staff events as an example. These people may know of open Chief of Staff roles and could potentially make an intro for you!
TRANSCRIPT
Welcome to the A Chief of Staff Podcast — David Nebinski here. The last two times I did a solo episode, I opened with a little jingle, so I'm trying that out again: six chief of staff job searching tips in 2026!
As a reminder, I'm the host of the A Chief of Staff Podcast, which is also a newsletter, and I host in-person events for Chiefs of Staff in New York (and yes, I wear funky pants).
I've been noticing increased interest around chief of staff job searching lately — people asking how to land a role, people actively looking for new ones. At the same time, there's been a bit of a hidden job market lingering in the broader tech job market over the last year or two, for a variety of reasons I won't get into here.
What I do want to get into is this: the chief of staff role is unique, and you have to lean into that uniqueness. Usually there's only one chief of staff at a company — sometimes more, but rarely — and no two chief of staff roles are the same. The people who land these roles typically represent a strong, distinct combination and partnership with a founder or executive. So you have to find the role and the partnership that really works for you.
If a company is hiring ten salespeople, you can be one of ten. But a company hiring a chief of staff is hiring the chief of staff. That's part of why the role is unique — and part of why there's a hidden job market for it.
So here are the six tips. I'll rattle them off quickly, then go into more detail on each:
Look for triggers
Search off-market
Lean into your positioning and messaging
Add value to founders
Attract inbound interest
Connect with other Chiefs of Staff, community builders, and content creators (like me, if you want)
1. Look for Triggers
There's usually an inflection moment for a company — a point when a new Chief of Staff hire or opening appears. One of the clearest triggers is a fundraising announcement. When a company announces a Series A or Series B, there's often a new Chief of Staff role opening officially — or the company is at least starting to think about it.
If you see a fundraising announcement, check the company's careers page, but also try to connect with the founder or anyone else you know there. A fundraise usually means the company is scaling and growing quickly — exactly the moment when a Chief of Staff can make a big impact, and exactly when companies tend to be looking to hire one.
2. Search Off-Market
I've noticed more and more Chief of Staff roles happening off-market. I'm getting messages from founders and CEOs before an official job posting goes up. Part of the reason: once a role is posted publicly, it draws a lot of interest and demand, so founders start scoping out who's available and who's interested before going to market officially.
It may also help with recruiting costs — some companies are short-staffed on the recruiting side and don't want to run a full search process. If they can find the right person off-market, it's a win for them and for the Chief of Staff.
I also see this happen on Twitter/X, where someone will post a few bullet points about a role before an official job description ever gets written. So keep an eye out for opportunities that haven't officially hit the market yet.
3. Lean Into Your Positioning and Messaging
Get clear on what you're actually looking for. Are you targeting a Chief of Staff role at a Series A healthcare company because you have healthcare experience or a personal connection to the space? If so, put that into one or two sentences and tell everyone you can.
That specific angle is your edge — and it's memorable. When someone shares a job description with me, or asks who might be a fit, I think back to the one person who told me that specific thing. It could be an industry, a customer base, or something about the role itself — maybe you love go-to-market work because you're strong in business development or partnerships. Lean into that. It doesn't have to be exactly where you end up, but specificity sparks conversations.
I remember someone who was very specific about wanting a Chief of Staff role at a family office. He kept saying, "David, who's hiring a Chief of Staff for a family office? That's what I want." He landed a role in about two months because he was so specific.
The same goes for any unfair advantage you have — maybe access to certain founders or people at certain companies. Lean into that. It helps you stand out and make real progress.
4. Add Value to Founders
Founders want to build and grow their business. If you can help with that, they'll notice — they'll see your email, they'll see your DM. If you reach out with a specific idea, like a potential customer introduction, most founders will respond. I know I would.
Other ways to add value: help with recruiting (many tech companies are struggling to hire software engineers or people with AI experience), test their product and give feedback, flag a bug on their website, or simply share something you genuinely like about the company. All of these are ways to start building a relationship.
You can also create content about a company. I love a blog post someone [Anna Reich] once wrote about wanting to work with Jay Clouse — a deep dive referencing his prior newsletters and podcast episodes, essentially outlining what she would do if she worked with him and how he might think about growing his business. It was extremely detailed and unique — and she ended up landing a role with him.
Inviting a founder to an event is another simple way to add value. If you're attending a healthcare leaders' event, for example, and you know a founder in that space, invite them along.
5. Attract Inbound Interest
Post content online — LinkedIn, Substack, wherever — about how you crushed your first 90 days as a Chief of Staff, how you approached onboarding, how you're using AI, or how your company handled annual planning. People notice that kind of content, and they start to see you as someone qualified, experienced, and genuinely excited about the work.
I've talked to Chiefs of Staff who became known in the community simply for being active and insightful — to the point where a founder reached out to them directly to review a Chief of Staff job description before running a formal search. You may think no one's watching your podcast appearances or LinkedIn posts, but people do notice, especially when the content is specific and insightful.
Becoming a guest on podcasts is another good way to raise your visibility. As your visibility grows, people start to think of you first — "David's obsessed with funky pants, I've got funky pants too" or "David hosts Chief of Staff events in New York, and I'm a Chief of Staff in New York."
Group chats and forums work the same way. If you're actively helpful answering questions in message-based communities, people remember that — and they'll refer others to you.
6. Connect With Other Chiefs of Staff, Community Builders, and Content Creators
I host Chief of Staff events here in New York — you can find details through the Chief of Staff Podcast or newsletter. The next one is Thursday, July 18. If you're a Chief of Staff in New York, I'd love to see you there. If you can't make it but want to hear about future ones, subscribe to the newsletter.
Connecting in person lets you hear how other people are thinking about their roles — casual, "water cooler" comments like "so-and-so might be hiring a Chief of Staff soon" often surface at events. Other Chiefs of Staff are often the first to know about openings, including their own eventual replacements.
I also include open Chief of Staff roles in the newsletter, so subscribe if that's useful. I've been hosting Chief of Staff events in New York since 2021 (I've lived here for about ten years), and I try to include roles and opportunities I'm personally aware of.
Events also give you a quick "vibe check" — you can size up a founder's personality in person, and they can do the same with you. Last year I hosted a Chief of Staff recruiting event where a CEO wanted to talk to a range of Chiefs of Staff just to get a feel for different people and hear how they thought about the role.
Those are the six tips — recap:
Look for triggers
Search off-market
Lean into your positioning and messaging
Add value to founders
Attract inbound interest
Connect with other Chiefs of Staff, community builders, and content creators
Now, a bit about how I landed my own three Chief of Staff roles — all three followed a similar pattern of adding value and going off-market:
First role: I started helping and adding value to a founder I knew. I made a strategic introduction, and one thing led to another. As the company grew, I already knew the customer base, and what started as freelance work turned into a full-time role. I never planned it that way — you never really know where things will lead.
Second role: Someone wanted an introduction to a woman I knew through my podcast. In the course of that conversation, they mentioned a project they were working on and asked if I wanted to help. We worked on it together, it went well, and it turned into an ongoing, more formal role as they built out their company.
Third role: I'd been friends with someone whose company was going through a shift during the pandemic. As a user of their product, I shared some ideas about what I thought could improve it. That turned into a conversation, then an offer to help execute on those ideas — and eventually a role helping the business pivot.
There's a clear through-line: off-market roles, built by adding value first.
I host Chief of Staff events here in New York and publish a newsletter — you can find both through A Chief of Staff Podcast. I'd love to hear what's working for you in your own job search, and maybe feature your ideas in an upcoming newsletter. Let me know what else you'd like to see covered.
That's it — six tips for Chief of Staff job searching in 2026. Signing off here.
I wasn't sure whether to close with the jingle again, but I did want to say thank you for being part of this journey over the last ten months or so. It's been really fun building out this New York Chief of Staff community, podcast, and newsletter. Thank you for coming to the events and for your encouragement — I'm excited for what's ahead, and thanks as well to all the partners who've helped make this happen.
If you have any questions, send me a DM on LinkedIn, Instagram, or email. Have a great day, and talk to you soon. Bye!
Transcribed and lightly edited for clarity and readability.
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