The top 3 things that make a 5-star Chief of Staff resume
PLUS some of my favorite resume hacks and tips that I used when applying :)
I didn’t think this would be the first post for the Right Hand Substack, but resume quality has been top of mind for me the past week. After launching Right Hand, I received 100+ resumes over a 24-hour period, whether through our website or this Typeform (candidates: please apply using this link! 😊)
While I review every single resume, I can’t respond to every single person with feedback because I just don’t have the bandwidth. That’s why the Typeform thank you message says “We'll be in touch soon if there's a fit!” The only exception to this is candidates who are contacted for an intro call with Right Hand — they’ll get resume feedback directly. Keep in mind: all candidates are evaluated across a number of factors, and while less-than-perfect resume quality isn’t a dealbreaker, it definitely doesn’t help you shine.
So I’ll use this post to highlight some of the major 🚩🚩🚩 I’ve seen on resumes and share my advice on how they can be immediately improved, which also improves your chances to get past multiple filters, both human and machine.
I get it — people are creative, fun-loving, original, and want to inject their own personality into their resume to reflect this and stand out. But in my opinion, that’s not the best place to do that (think about all the chances you’ll have to show that side of you during interviews IRL!). Unless you’re going REALLY big, like printing your resume on a cake, don’t worry about standing out with your resume formatting. What stands out more is a really sharp, well-formatted doc.
Here’s an example of what nearly every resume from Columbia Business School grads looks like (I’ve seen a few):
Some important things to note about why this formatting is excellent:
Times New Roman font, probably 11 pt or 12 pt throughout (including the header!). Makes it really easy to read. You don’t need your name in 20 pt or in a different font or color.
Consistent margins (usually 0.5-1 inch) and indentation
Adequate and consistent spacing between sections
It’s one page. This is a big one. Notice that the earlier experience has just a few bullet points, while the most recent have more. This saves you a ton of space and lets you pad your most recent experience (more on the content you should include here in a bit). If you have <10 years of experience, try to condense your resume to 1 page. If you have 10+ years of experience, it’s OK to extend to 2 pages, but don’t spill onto 3 pages unless you’re in academia. If you have a decade or more of experience, you can summarize earlier and perhaps less relevant work like this:
If you’re a recent grad, it’s fine to have your education at the top and to include relevant honors, leadership roles, and memberships. But if you’ve been out of school for at least a few years, your education isn’t too relevant anymore for your next gig — place it at the bottom before “Additional Information”.
As for what your bullet points should include, here’s a hack I used when I was applying for Chief of Staff roles. I reviewed a bunch of CoS job descriptions and dumped all of the bullets about the role responsibilities into a Google doc. Then, I condensed them all into major themes and bullet points, and made a long list of strong verbs that were directly applicable to the role (e.g. built, led, implemented). At the time, I was transitioning from a role in venture capital, so I looked at all of my experience and thought, OK, how can I speak to specific accomplishments and present them in a way that sound Chief of Staff-y? 😂 I didn’t want whoever was reviewing my resume to expend energy trying to make the connection between my experience and what they were looking for because — and based on how I presented my experience — I was already a Chief of Staff. I hammered this point in my interviews as well.
If you do this really well, you almost never need to tailor your resume to any company, particularly if you’re targeting the same role at companies of similar size, stage, and for which the responsibilities are equivalent. The same goes for the cover letter. Applying for full-time roles is basically a full-time job in itself — if you’re a candidate, I’ve been in your shoes and I empathize with you. The last thing you want to do is spend an inordinate amount of time customizing your resume and cover letter to every single company to which you apply only to get rejected by the ATS. It’s much more efficient to spend a ton of time getting it right the first time around making your accomplishments as relevant as possible to the Chief of Staff role itself, and then spending very little time tweaking it (if absolutely necessary) for the specific company.
One other major tip: try to quantify every single bullet point. Yes, you did X task or project, but what did it result in? The more numbers you can use, the better. You want to be seen as someone who is results-driven (and gets results), not a task completer. This is arguably the most important aspect that differentiates a stellar resume from a ¯\_(ツ)_/¯ resume. Review each bullet point and ask yourself the following questions to help quantify your achievements:
How many (hires, programs, deals, partnerships)? This is a raw number and helps reviewers understand size, scale, breadth, etc.
How much? Usually dollar amounts.
By how much? Can be described as a percentage or x-fold increase/decrease.
It’s also worth noting the things you should NOT include on your resume:
Pictures, icons, or graphics of any kind
Colorful text — just stick to black!
A list of skills — this will be evident from your experience, and can be referenced in your cover letter
An executive summary — these tend to be filled with trite phrases like “experienced professional”, “collaborative communicator”, and “passionate team-player”. Well, you’d better be! You want to avoid listing a bunch of these non-specific skills anywhere on your resume. Only if skills are technical in nature (Salesforce, Tableau, Looker, etc) should they find a home on there; and try to keep them to one line. Don’t use precious resume real estate to describe yourself with buzz-words only to repeat the same thing in the true value-add bullets beneath your experience.
Training, certifications, and memberships that are irrelevant with respect to the Chief of Staff role
Spelling misteaks 🥩
While a lot of founders just look at information about where a candidate worked and went to school before deciding to speak with them for a given job opening, the same process doesn’t necessarily apply for Chiefs of Staff. The role is so unique in that you’re not just focused on a single area of the business. Instead, you’re working across the executive team, leading a variety of initiatives that could vary wildly in terms of breadth and depth, and building out processes and systems from scratch in some cases. So your resume, its content, and the context you provide becomes critically important in evaluating your candidacy.
Think of the value of your resume in this context: the average salary range for a Chief of Staff role right now is between $130,000-$180,000. Consider that your resume is a critical building block to helping you land that job and salary, so let’s just say that it helps you get ~25% of the way towards that. If you haven’t pored over every single verb, adjective, and linker on a document that’s potentially worth $45,000, you’re doing it wrong! Once you’ve defined your achievements and quantified them, context become massively important. Keep in mind how expensive the real estate of your 8.5 x 11.5 inch resume is (~$66,000/sq. ft!) 😊
Let’s take a look at two examples of achievements with varying degrees of context for a candidate applying to a CoS role reporting to the CRO:
A: Sourced and closed a $1M contract
B: Sourced and closed $1M contract, the 2nd largest customer in company history, resulting in expansion into Europe
Wow! B > A by a long shot. Quantifying your achievement is table stakes, but getting really specific and providing supporting context as to why it mattered so much really makes it shine. In B, you didn’t just move the needle in terms of revenue, but you landed a whale and it gave your company a strategic edge in a new market. Impressive. So think about the context of your achievements, and be sure to use those 1 or 2 lines to pad your quantified achievement wisely! Because by now you can probably figure out how expensive those are, too. 😆
If you hit these 3 things out of the park — formatting, content, and clarity — and you meet the job requirements, you’ll be sure to increase your hit rate and get more invitations to interview. Hopefully these tips provide a good North star for you to craft a stellar resume — if yours is already 5-star and you’re looking to get placed as a Chief of Staff with Right Hand, be sure to submit this Typeform!
Founders who are hiring ➜ DM me on LinkedIn and let’s talk :)
If you liked reading this, feel free to click the ❤️ button on this post so more people can discover it on Substack 🙏
Until next time, Right Hand fam! 👋
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Finally, if you liked reading this, feel free to click the ❤️ button on this post so more people can discover it on Substack 🙏
Until next time, Right Hand fam! 👋