Chief of Staff, a Critical Role Among High Growth Startups

The “Chief of Staff “ role has quickly moved from the political world into prominent, high-growth technology companies. But what does the title really entail?

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The Washington Post recently portrayed a secretive members-only group on the west coast, meeting to discuss the latest updates and gossip among their respective tech companies. They were referring to a very specific and self-selecting set of individuals — the “Chiefs of Staff” (CoS) from well-known startups. This may be a bit dramatized — I imagine a bunch of under 30-something american apparel startup t-shirt clad men and women huddled in a dark lounge keying into the latest industry activity while quietly judging who has real influence in their business.

The truth is Chiefs of Staff vary widely between organizations. If defining “business development” at a startup wasn’t already difficult and vague enough, the Chief of Staff has brought that challenge to a whole new level. Chief of Staffs have existed in the political sector since the 50’s. The White House CoS is defined as the highest ranking employee to the President as he/she manages communication channels, scheduling, the advisory teams and simply access.

Chiefs of Staff have gained momentum among tech companies large and small as the pace of growth quickens and the need for efficiency and structure becomes a necessity among a leadership team.

So what is a Chief of Staff in the context of tech startups, what are the responsibilities, what do you look for when hiring a CoS, and is it a necessary function given other more specific problems and needs of a startup?

As the Chief of Staff at Spring, I thought it would help others looking for these answers to give a glimpse into my journey, my always-in-flux responsibilities at Spring, and my perspective on how the CoS position is evolving and becoming a necessity.

A brief history.. of me.

It’s easiest to describe my career as a bit of a generalist or maybe.. renaissance man? I’ve worked with companies managing business development, sales, marketing, operations, recruiting, product, design, legal, fundraising and more. Foursquare gave me the opportunity to witness first-hand how to create a well-oiled machine poised to solve problems and grow quickly. At techstars, I worked cross-functionally with the class doing all of the above. Joining ChatID (Welcome) as the first employee, I helped raise money from tier 1 investors, build and launch our first product, pivot the business, sell into Fortune 500 brands, and grow our team. I joined Spring when the company was fewer than 5 employees to focus on building the supply side of our marketplace with the world’s top fashion brands while working cross-functionally with our marketing, product, and operation teams.

My transition to Spring’s Chief of Staff was a rather natural occurrence as I’d been providing coverage for gaps in the business and operations from very early in the company’s life. It’s the do-it all, do-it fast mindset that I believe is critical to a startup’s success. Startups, especially at the earliest stages can do very well having an extra hand that is able to pick up the slack where no other full-time hire is focused.

The balancing act for a CoS in a quickly growing business is to fulfill the current needs of the CEO and company while keeping an eye towards building a team that can own and manage the focus area or project specifically over time.

CoS, a critical role.

A few reasons the CoS is becoming a more recognized role among tech companies:

• CoS provides an additional layer of structure.. without necessarily becoming the quintessential “gatekeeper”
• Startups need to move quickly — time is the most critical asset. CoS fulfills areas of the company that have a direct impact on the business / product but do not always fit the core job descriptions of the rest of the team.
• CEO’s never have enough time to do it all themselves. The best CEO’s, in my opinion, are leaders with a whirlwind of ideas, who live in a ceaseless deluge of creativity and never enough time to get it all done. CoS provides coverage to run and explore new areas of opportunity without distracting or diverting resources from the rest of the company.

How the functions vary by company.

As much as the culture of a company matters in the creation of a CoS role, the CoS is more a byproduct of the company’s ever-changing needs. That is to say that while every high-growth startup has inherent differences in mission, product, team, culture, business, etc. they are all similar in the fact that the sheer pace of their growth justifies having someone who can keep visibility to the high-level vision of the CEO whilst operating at the ground level.

The devil is in the details and the CoS succeeds at facilitating the CEO’s vision (and tangential visions) while enabling other members of the leadership team to work together and get decisions at the top made faster.

Having spoken to and heard from other CoS’s, the day-to-day responsibilities can differ widely from one business to the next. One common theme is the CoS typically has wide access to sensitive data and key decision makers across the organization. Here are a few example projects I work on:

• Strategic projects — Partnerships, M&A diligence, product-focused exploration
• Bi-weekly team leadership meetings
• Board meeting prep (including presentation)
• Investor updates / fundraising pitch decks
• Quarterly Roadmap / status tracking and updates
• Business Development for product related partnerships (e.g. maintain a strong understanding of and relationships with other technology companies building interesting things in our space)
• Assorted items for CEO — filtering team information, presentations, etc.

The traits of a good CoS

The term gatekeeper has been used to describe the CoS, particularly in politics. I would argue facilitator is a better description of how a CoS should actually perceive their responsibilities. The foundation of this role for me is trust. Gaining the respect of an executive team and trust among colleagues doesn’t come overnight. For this reason — the position can be difficult to hire for from the outside vs. grooming a current employee.

• Trust
• Multi-tasker
• Entrepreneurial
• Efficient with limited resources
• Strong communicator
• Confident in managing up
• Ability to comfortably dive into most/any area of the business or product
• Good sounding board for others in the company — provide open, honest feedback
• No ego — help employees understand where you can be useful for them vs. a roadblock to the top.

Getting into the role.

I’ve seen these positions called many things with varying definitions internally or externally (generalist, founder’s associate, chief administrative officer, CoS, etc.). Often, new startups typically know they need the extra support that comes with having a CoS, but the title seems too formal given the size and roles of the founding employees. Finding your way into a CoS position depends heavily on understanding the current needs and stage of the company. Earlier stage startups are prime for the generalist or founder’s associate role. This is not an executive assistant position as much as it is a facilitator of the CEO’s priorities. Working with a variety of teams requires a broad skill-set and flexibility to work intelligently on ad-hoc projects. Speed is the greatest asset. I would also argue that a CoS could develop out of a variety of existing positions — product, operations, business development, marketing. This candidate will have deep exposure to certain aspects of the business but may need to prove the ability to work cross-functionally.

CoS career advancement.

The CoS position is well suited to be great grooming for an executive operational role in the business. Many CoS’s go on to become VP of Operations, GM, or similar at their respective or new companies. Personally, I’m learning and gaining experience working alongside great founders and a fantastic team to ultimately venture on to start my own company. Arming myself with the institutional knowledge that can only be gained by helping build a company from the ground up, will be critical to my future success as a founder and leader. In this regard, the role of CoS couldn’t be a better fit for aspiring entrepreneurs.

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