The Chief Delivery Officer role is one of the hardest to hire for.
You can promote from within rather than recruit into position. You can support an individual to grow and develop into the role. BUT … the person you need at 10 people is not the person you need at 30, 75, 300, 1,000, etc.
When appointing for the role of delivery principal you're looking for a very special set of traits and capabilities.
Those are discussed in detail in the What makes a CDO? section. For now, it's important to establish that there's a fundamental set of soft and hard skills that have to intersect in a high performance Chief Delivery Officer.
To complicate things more, the person who fills this role often plays a crucial part in the growth and development of the business.
Consequently, filling this role is both very important and very challenging.
I spoke to several CEOs/founders to hear their specific experiences of appointing someone to the role of delivery principal. This section is largely taken from their insights.
There's so many skills that are essential in this role — the delivery principal is one of the hardest things to hire for!
Alex Frison, CEO, Syde
A consistent insight, though, is both that the CDO role is vital to the business and also that it's one of most difficult positions to fill, whether by growing or promoting someone from within, or appointing through hiring.
This section looks at some of the reasons why and what you might do about it.
So, when you're looking to appoint a CDO what do you need to bear in mind?
The CDO and the growing business #
The particular mix of characteristics and strengths needed in this position in the business is necessarily different at each stage of growth. CEOs recognise that the business changes at several headcount breakpoints, commonly around 10/15 (when the founder begins to lead the business, rather than just be one of the team), at 30/35 (when the founder becomes a CEO, leading the leaders of teams), and again at 75ish (when the CEO begins to leave the day-to-day to others in order to focus on ), and then further up at 300+ also.
Jake Goldman, president and founder of 10up and partner at Fueled, is clear that the person you need in this role in a 10–15-person business is very different from what you need in a 30–50-person business, or in a 80–120-person business, or a 300-person-plus business.
The person you need at 10 people is not the same person that you need at 30 people, at 75, at 150, at 300 or beyond.
Jake Goldman, president and founder, 10up/Fueled
Jake has seen the challenges of these stages of growth up close at 10up and latterly in the merger with Fueled.
At 10up, a project manager (PM)/delivery manager (DM) was the 4th or 5th person to be hired, such was Jake's understanding of the importance of the role.
In the earliest phases of a small or young company though, he says, the business is usually pretty efficient in running client projects while also being very loose, adapting quickly to context.
That can scale a bit, maybe being adequate up to 2 or 3 simultaneous customers, but it quickly becomes fragile. As the business grows, something more thoroughgoing is needed.
Karim Marucchi, CEO of Crowd Favorite, goes even further.
Having a CDO in position is essential, he says, if the business is going to grow past the 60/75 person threshold. It's at this stage that you're creating value in the value chain for the customer and that's only possible with any consistency with a delivery principal in place.
This necessity is particularly clear in the story of growth for Syde, Europe's biggest WordPress agency. 2019 was a year of hyper-growth for Syde when they won several big clients back-to-back, and went from ~35 people to ~120 people as a consequence. Alex Frison, CEO, describes how things moved at such a pace that they carried structures and practices for 30 people over knowing they were not fit to continue. Something needed to change. So Syde created the Delivery Director role and hired specifically for the role.
A CDO for a mature business #
For CEOs and founders, it's clear that the maturing business needs to stretch forward towards greater professionalism.
Professionalism covers many things. We cover what that means for customer and project delivery in other sections of the handbook.
That said, a large part of delivery professionalism can be summarised fairly simply. It has to do with:
- comprehensive, robust, replicable processes …
- … that are clear for customers and staff
- … that reflect the organisation’s persona
- … and are in tight alignment with business objectives.
That is true for client delivery just as it is for any other part of the business. This is the CDO's role says Myles Lagolago-Craig, CEO of XWP: to set the standards, hold people accountable to them, a make them meaningful so they're a metric for progress towards successful outcomes.
There is an important balance, though.
It's vital that processes and practices are comprehensive and replicable. BUT, they need to work as a foundation rather than as the house itself. Whilst delivery processes are important, they should create space for experts to expert, and for the exercise of pragmatism and common sense attuned to the context.
In other words, in a mature business the delivery principal has to hold the tension in a fundamental balancing act between:
- systematic and thoroughgoing processes on the one hand, and
- space for creativity, innovation and situational agility on the other.
It's easy for project management to rule the roost. Tom Willmot, CEO of Human Made, talks of how easy it is for a business to focus on adhering to those high capacity delivery processes — they certainly can enable scaling. Human Made was able to take on 7-figure client projects as a result. Similarly, Alex enabled Syde to cope with sudden growth by bringing in someone to make their delivery processes robust and reliable. But it's problematic when the processes themselves become the focus, and Tom and Alex both advocate strongly for project work to remain steadfastly outcome-focused.
Promoting from within vs. hiring into position #
Businesses that have grown from small origins do their utmost to honour team members and respect those who put in their all from that start.
But there's a key question here:
Is it possible for someone internal to grow with a growing business, developing into the role of Chief Delivery Officer in the larger, expanded context?
The short answer is yes … but.
In reality, it's very difficult to achieve, and many CEOs attest to the challenges of such a praiseworthy ambition.
Most, being good people, will have tried to do this — to promote someone from within without that person necessarily knowing how to do project management at scale. And most will have found it problematic along the way, with experiences of turbulent projects, frustrated teams, a burnt-out delivery director, or worse.
As the business gets bigger and takes on more and larger client projects, there's a point at which it's not possible for one person to be involved in delivering everything. Project delivery has to become detached from any single personality.
In other words, the delivery systems and processes should be separate from the person themselves, as if they are a product for the business.
Tom, Alex, Myles, Jake, and Karim all recounted experiences of headaches promoting from within — ways in which it almost worked, but then needed to change. All said that recruitment specifically for the position has been more fruitful.