How to get a Job as a Chief of Staff

Scott Amenta
Chief of Staff Network
4 min readMay 7, 2018


The Chief of Staff role has transcended beyond the political landscape into the tech, media and venture capital world. In the past few years alone the position has proliferated among young startups and their larger private (and public) counterparts alike. The CoS has become a sort of right of passage for young strategically minded generalists ready to cut their teeth building and growing companies alongside their CEOs and executive teams. Whether you’re looking to become a CoS in a new company or trying to create the role in your current organization, the position remains rather elusive.

How does one actually become a Chief of Staff in the tech/media world? Here are 5 simple ways you can navigate your way into a CoS position.

1.Join in a different position and create the CoS role internally. Most companies probably don’t have CoS at the top of their hiring plan. This doesn’t mean they don’t need one. If you already work in business development, strategy, finance or operations — something that tends to be cross functional and has wide purview across the company, you’re off to a great start. Sales or product for example, are often too specific in their day-to-day functions.

Early-stage startups tend to have similar challenges and a greater need for generalists that can get many things done across functions. That said, the CoS position is most effective when there are stakeholders owning specific parts of the business (product, customer support, operations, etc). It’s rare to find a need for a CoS at companies with fewer than 25 employees. On the flip side, more mature companies have greater structure and therefore rigidity in employees taking on wider responsibilities — they hire specialists but often recognize the need for greater support at the leadership level.

2. Create the role yourself in the interview process. This sounds crazy, but as described earlier, most companies / CEO’s still don’t know the value of a CoS until they 1.) hear it first hand, and 2.) experience it. If you really want to be a Chief of Staff and have your heart set on a particular company, just go for it! Why not start at the interview itself. Being honest about your ambitions and making a good case for why the company needs a CoS shows that you have a clear understanding of their business and the know-how to be effective in this position.

3. Find companies that are hiring for a CoS. This is the obvious path and luckily there are many companies looking for great chiefs now to work side-by-side with their CEO’s or executive teams. However, proving yourself as a capable generalist that can lead from behind, stay organized, communicate well and multi-task under a broad range of to-do’s is the real challenge. This is a public posting so you’re up against other potentially awesome candidates. Set yourself apart by doing a few key things:

1.) Ask intelligent questions about the business — you want to get to the heart of the challenges they are facing.

2.) Offer insight about their business — do your homework and offer an opinion of strategy, product enhancements, industry or business model. Demonstrating you can think critically about this company today will help you stand out instantly.

3.) Go beyond short term thinking — the questions you ask and the insights you offer should lead to observations and inquiries about the long term vision of the company, how they approach employee growth, learning and development and if they have the team to do it all.

4. Replace an existing COS. More and more companies have been hiring CoS over the past 3 years than ever before. Yet, the role itself normally only lasts 18–24 months before folks move on to focus on a specific area of their business or join another company. This is a great opportunity for prospective chiefs. Unlike other roles, a good CoS will recognize when they are ready to move on from the role and seek to hire their own replacement. Reach out to the CoS in companies you admire, you’ll be amazed by people’s willingness to grab a coffee and see if you might be a good fit.

5. Start your own company. No, you won’t be a chief of staff. But you’ll have leveled up to what many tech and media CoS ultimately become — their own CEO. This role attracts entrepreneurs and breeds them into next-gen leaders joining or building all kinds of companies.

If you believe you have what it takes to be a great operator alongside a CEO and exec team, then consider a becoming a CoS!

Looking for a new career path as a Chief of Staff in a high growth company? Let us help you get hired. Contact us at the Chief of Staff Network to share your story.

And, if this article was helpful give us a clap and share with other hopeful CoS candidates!



Scott Amenta
Chief of Staff Network

founder of Chief of Staff Network, co-founder of Propel, co-founder of Sylva, former CoS at Spring, producer @WatchRoomMovie