Welcome, aspiring & current Chiefs of Staff!
If you’re reading this, you might be:
In the throes of submitting your resume to various Chief of Staff positions
Considering whether or not a Chief of Staff position is right for you
Curious as to what a Chief of Staff is
Navigating the murky waters of the Chief of Staff role
Considering your next role post-Chief of Staff & wondering what’s out there
My mom 👋🏼
I’ll be (attempting to) publish bi-weekly newsletters to answer the questions that I often get asked when folks are thinking about being a Chief of Staff. I’m also hoping to dive deeper into challenges that I’ve seen arise time and time again when people actually land the position.
So if you fit any of the categories above, or want to support me in my writing journey, submit as few or as many questions below and subscribe to read the answers!
In this inaugural issue, I’ll be answering this question that I’ve received in my LinkedIn inbox time and time again: How do I get a Chief of Staff job?
(PS if we’re not already connected on LinkedIn, shoot me a request!)
How do I get a Chief of Staff job?
This is, without a doubt, the number 1 question I receive on a weekly basis. It can often feel like a conundrum of sorts when it comes to applying for Chief of Staff roles: on the one hand, there seem to be hundreds of Chief of Staff roles popping up daily on LinkedIn and everyone and their mother wants to hire a Chief of Staff. On the other hand, when you do submit an application, you often don’t hear back and wonder which ATS blackhole your resume has landed in. These are the 4️⃣ tried and tested ways that I’ve been able to help candidates land a Chief of Staff role:
1️⃣ Pitch the role internally at your current company
Just because you’re looking to step into a new role, doesn’t mean your company won’t be up for it. I look at examples like Ellise McDonald (Chief of Staff at Wise Systems), Jake Bengtzen (former Chief of Staff at Finicity, acquired by Mastercard), and Piero Marlia (Business Partner/CoS equivalent at Google) who came from sales type roles within their companies and moved into a Chief of Staff role when they looked to see more of the business and work more closely with an executive.
If there are executives or leaders at your company that you’d like to shadow more closely, toss out the idea of you taking on a Chief of Staff role by their side. It will also be a chance to stay within a company where you have plenty of context and don’t need to relearn a company culture and operating rhythm from scratch.
You also don’t need to pitch the Chief of Staff role as “all or nothing” - i.e. “I’m interested in being your Chief of Staff and if I don’t get it, I’m going to look elsewhere, bye!” Soft pitch the role by scheduling some time with the executive you’d like to support and ask if there are opportunities for you to work more closely together. Take on projects that can help alleviate the workload for your potential principal and when the working relationship is established and trusted, you can then float the title of “Chief of Staff” with them and see if you can make a formal title transition.
2️⃣ Pitch the role externally at a company you’d like to work at
Even though hundreds of companies are hiring for Chiefs of Staff, there are still so many executives out there that don’t know the force multiplying benefits of having a Chief of Staff. A Chief of Staff job posting might not exist simply because the CEO of a startup hasn’t thought to hire one just yet.
Maybe you’ve even seen something like this blurb below on job posting pages and this is the perfect opportunity to pitch a Chief of Staff role to a company you’re excited about.
“Creating the role for yourself” is a common Chief of Staff job strategy that I give to many aspiring Chiefs of Staff because it shows tenacity and taking initiative from the get go. Instead of looking for Chief of Staff roles and having the company/mission be secondary to your job search, flip the order of operations and look for companies and principals you would want to work with. Maybe you’re looking for a female founder to learn from or it’s really important that you work at a socially impactful company. Find the places that you would be most excited working at and pitch yourself as a generalist, Jill of all trades, operational catch-all. You’d be surprised at how many companies are looking for GPSGs: General Purpose Smart Gal/Guy.
If you want help on crafting your perfect “cold outreach” email to a company you’d love to work for, let me know! I’ve sent hundreds, if not thousands, of cold emails in my career and we can work together on fine-tuning your pitch!
3️⃣ Shadow an existing Chief of Staff
If your organization already has a Chief of Staff, this is great news! It means your company is already bought into the efficacies of a Chief of Staff and would happily consider more candidates moving into a Chief of Staff role in the future.
Ask to shadow the work of a current Chief of Staff at your company and offer up your time to help with the projects on their plate. As any Chief of Staff knows, there’s an infinite to do list and if you’re able to offer any of your functional knowledge and support, you’ll gain additional access and oversight into the company by nature of working alongside a Chief of Staff.
Additionally, because Chief of Staff tenures tend to span 18-24 months, you can put yourself in the running to be the replacement candidate when the current Chief of Staff is ready to move on from the role.
Be forewarned that the existing Chief of Staff may not want to leave their current post and shadowing does not always guarantee that you’ll be able to step into the post at your current company, but either way, you’ll gain some new responsibilities and skillsets to add to your resume that will better position to be a Chief of Staff internally and externally!
4️⃣ Ask for a warm intro
My last piece of advice, which can sometimes feel like an “oh-duh” moment, is to ask for a warm intro! I’ve facilitated hundreds of these warm intros throughout the years and even if it’s not directly to the CEO or hiring manager, a foot in the door is better than nothing at all. Two pieces of follow up advice when it comes to asking for a warm intro:
👆🏼 Make sure to have your 3-5 sentence blurb ready to go when you’re asking for a warm intro. Whenever I’m looking to introduce two people in my network to each other, I always ask the “askee” to send me a short blurb to share with the “asked.” This puts the onus of the introduction on the “askee” instead of the facilitator. An example of a good blurb:
[NAME] is interested in [ROLE] at [COMPANY] and would love to chat with you about working at the company and any insights you might have on the role. [MENTION some relevant experience that you have for the role - keep it short! This shouldn’t be a regurgitation of your LinkedIn or resume] She/he/they are especially interested in [COMPANY] because [TALK about what is most interesting about the company]. Let me know if you’re open to an intro and the best way to connect you two!
✌🏼 Build up your warm intro network by connecting with people regularly, not only when you’re looking for a new role. I try to adhere by the “20 people a week” rule (DISCLAIMER: this is a totally made up rule I created): every week, find 20 people that you feel like would be a good addition to your network on LinkedIn:
People you would like to work with
Peers in similar roles to you
Aspirational people who you would like to follow in their footsteps
People at companies you admire and might want to work at some day
Many people I talk to feel like it might be disingenuous to connect with people you don’t already know, but isn’t that what networking is? It’s not for reconnecting you with people you’ve already met, but instead connecting with folks where you might be able to help each other in the future. If you don’t connect with them now, how will you know if there are opportunities to work together?
I also have a lot of thoughts on LinkedIn networking and content, so if you’d like to read an entire newsletter on that in the future, let me know!
If you’ve enjoyed this issue, consider subscribing and sharing. Additionally, feel free to reply to this email with feedback on whether this was helpful to you and any suggestions you might have.
👋🏼 Until the next issue,
Clara
PS: I’m going to work hard to keep all the content in my newsletter free so that it’s accessible for everyone, but if you want to help support my writing endeavors, you can buy me a matcha 🍵
Been looking forward to this. Thanks, Clara.
Hey! Would love some examples of cold outreach example emails - what's the best way to find some examples you've sent?