Why Chief of Staff will be a critical scaleup role in 2021

A scaleup CEO, yesterday.

There’s a lot of money flooding into early-stage tech businesses right now.

New seed funds are launching every week, follow-on funds are ballooning in size, and Series A+ funds are pushing deeper into earlier-stage deals, to ensure they can still carve out their required allocation in later rounds.

But larger rounds at earlier stages also create challenges for founders; what was a six-figure round five years ago is now seven figures, meaning revenue targets, headcount requirements and investor expectations have increased accordingly. Suddenly there’s a need to achieve so much more in a similar timeframe.

Cracking scalable growth, improving operational rigour, accelerating product roadmaps, introducing and iterating sales processes, increasing the velocity of hiring and onboarding, scaling organisational structures, introducing consistent comms, engaging investors, revising cashflow models —it all needs doing, all at once. In late seed and Series A teams, everything is on fire.

Scaling the C-level team doesn’t immediately solve the problem, since roles are tightly defined and hiring takes time. There often isn’t enough flexibility to deploy senior resource where and when it’s needed, meaning focus is another issue; a CEO might have a dozen items on their to-do list, when only the top 2 or 3 are going to move the needle in the business.

What’s needed is an experienced generalist who can support the CEO and leadership team, complement and deputise for them, roll up their sleeves and lead on short-term projects across the business as and when required.

The role we’re talking about is a Chief of Staff (CoS), and it’s one that I think will become both neccessary and foundational, as scaleups struggle to solve the inevitiable pain that occurs when the ever-increasing expectations of larger rounds collide with finite bandwidth. It’s certainly not a new title, although historically it’s been larger, more established businesses making these hires — but the abundance of early-stage investment means a retooling of the role and responsibilities is required to fit an earlier stage and size of business.

…it’s clear investors see the increasing need for high-velocity scaleups to consider a Chief of Staff, describing them as a “temporary strap-on brain pack”, “the leadership team’s sweeper”, and “a troubleshooter”.

An example is 2020’s black swan, Hopin, which has grown from 20 employees in January 2020 to nearly 300 a year later. Hopin advertised for their Chief of Staff within a month of announcing their $40M Series A in July. While that appointment won’t have been solely responsible for ensuring the business stayed on the rails during the chaos of scaling, it’s exactly that environment of cash-fuelled growth where CEOs need the second best option to cloning themselves.

A common view is that a Chief of Staff isn’t neccessary if a COO is already in place, but whereas a COO’s responsibilities are well-defined and process-driven, a CoS has permission to colour outside the lines. For example, if the COO were managing HR and People functions, the CoS might support the COO by managing a specific recruitment campaign, or leading on a project to devise a scalable remote onboarding process — they’re not going to lead long-term, but can ensure more gets done in the short-term.

By the same token, it’s unlikely the COO would have the capacity or experience to manage the product team while the Head of Product is on sick leave, or help the CRO to audit the sales development workflow, or lead a brand refresh of the business. A good CoS isn’t neccessarily an expert in all of these disciplines, but can draw from their broad experience to work in a cross-disciplinary fashion.

The area of responsibility where I’ve seen overlap between the two roles, is typically the ownership and management of performance-related metrics (e.g. implimenting and driving company-wide OKRs) but otherwise the CoS doesn’t have a fixed mandate and can support the CEO, other senior leaders and teams as required.

Having spoken to several European VCs over the past month, it’s clear investors also see the increasing need for high-velocity scaleups to consider a Chief of Staff, describing them as a “temporary strap-on brain pack”, “the leadership team’s sweeper”, and “a troubleshooter”. One successful seed investor told me that “any team that’s raised a few million pounds probably needs to consider it.”

[NB — many businesses and job specs confuse the responsibilities of a CoS with those of Executive Assistant, even though they’re very different roles.]

As a bona fide generalist, the Chief of Staff role is one that really excites me. Startup roles typically becomes hyper-specialised beyond the founding team, but this year will see significant new opportunities for experienced operators with a diverse set of skills.

2021 will be the year of the Chief of Staff. Time to help put out some fires.

I offer weekly Office Hours — to help founders and investors with problem-solving, to discuss ideas and new opportunities; anyone can sign up. If you’d like to chat, you can find my availability here.

COO at Ori Industries. Previously Co-founder at Ricochet AI (acquired). Entrepreneur-in-Residence @ Techstars & Ignite. Former Hyperlooper and Twitchhiker.