Time-stretched founders often underinvest in CEO support - preventing them and their business from getting the full benefit.
In a previous piece, we covered the enormous impact of building a CEO office - and the importance of getting this in place at the right time.
Unlocking this potential, however, does not end with the (hugely important) decision to put in place a dedicated CEO office function. Having seen many founders go on this journey, we know it has to be done properly if it is going to actually allow a founder the time to focus on important business decisions. This means finding the appropriate hire, onboarding effectively, and thinking strategically about scaling this function from the outset.
It all starts with the right hire
A CEO office may end up scaling in tandem with the business, but it will generally start with a single hire to support the CEO - that could be a chief of staff, a strategy associate, or head of the CEO’s office. If you want to future-proof the success and growth of this support function, it’s crucial to get that hire right.
The exact responsibilities of this first hire depend on your needs, but having long-listed hundreds of CEO office candidates for our portfolio - and interviewed over 100 - we have a strong sense of what hiring well for this role looks like.
Your first CEO office hire can have a range of backgrounds, but in all cases will come from a high-achieving background. That impressive track record will also be important to attract more junior talent around this individual if and when the time comes.
The backgrounds of individuals in these roles vary, but startup operations is common. They may have worked in venture, professional services like management consulting or law, or in the industry that your startup operates in, such as healthcare.
Robin Trickett - now a VP of Strategy at cybersecurity startup Binalyze - explains that their level of experience can vary depending on the needs of the company: “A CEO office can be effective across different domains: strategy, operations, and execution. If your primary gaps are around owning strategy, you are likely to need a hire who has seen the high growth scaling first hand than if your needs are primarily execution based.”
However, there are some essential attributes the ideal candidate must possess to succeed in this position. They need to be analytical and self-driven, enabling them to independently pursue and achieve goals. This self-driven quality, when paired with thorough onboarding, creates a powerful synergy. The right hire, immersed in the company's vision and operations from the start, quickly develops the ability to anticipate needs, manage their own workload, and drive initiatives forward with minimal guidance.
Crucially, they must also be adept at navigating interpersonal dynamics. Building relationships across your business is vital to effectively drive forward the CEO's agenda. They need to be willing to get their hands dirty while maintaining a strategic perspective. With proper onboarding, this combination of attributes results in a hire who functions as a natural extension of the founder, amplifying impact through proactive, self-directed action rather than requiring constant management.
This will require a strong cultural fit with the CEO — above and beyond what would be required of another senior hire. They won’t be the final decision maker but they will provide necessary advice based on synthesized information - hire someone who can understand you and the company deeply.
This was something that Brandon Deer - now Chief Strategy Officer and GTM COO at UiPath, where he started in the CEO Office - said was sometimes overlooked. “A candidate can be great on paper - but a chief of staff is going to be, interpersonally, the closest to the CEO. This means the relationship hinges on chemistry and trust.”
“A candidate can be great on paper - but a chief of staff is going to be, interpersonally, the closest to the CEO. This means the relationship hinges on chemistry and trust.”
Brandon Deer, Chief Strategy Officer and GTM COO at UiPath
One hire can’t be your silver bullet
It’s vital to understand that this role can’t do everything. A single hire can’t solve every problem, and a member of the CEO office is also not an EA to help you manage your diary. Therefore, strategize upcoming work spikes that are pressing and prioritize someone who can help you with this. For example, if you know that regulatory topics will be important, hire someone with this experience. The same goes for fundraising. One of the things our talent team here at Bek often help founders do is rigorously assess the support you need best, and prioritize the most vital skills.
Mostly though - you have to think hard about candidates’ potential: are they a capable all-rounder who can grow into the role and adapt as the company changes? For example, you may want them to be more aggressive in helping you advance your goals in the early days of a company, and then grow into more of a mediator, who can help coordinate different functions smoothly as the company grows and the business becomes more complex.
Hiring someone with potential, who can develop with the function and the business, will also ensure that the individual stays with you and the company longer. The longer they can stay in the role and learn the company and its challenges inside out, the higher their performance and the performance of the CEO office function will be.
Not a quick fix-all: onboarding and embedding your hire
This hire can be hugely impactful - but they aren’t a quick fix-all. Hiring the right person is only the first step in establishing an effective CEO support function. The onboarding and embedding process is often the make-or-break factor in realizing the full potential of this role.
Many founders, after setting up a CEO office, find themselves puzzled when they don't see the anticipated improvements and continue to struggle with the same challenges. In our experience, this disappointment can be traced back to inadequate onboarding in nine out of ten cases.
We have personally seen an instance where a CEO lost a very capable and well-qualified chief of staff due to onboarding. There was no competency issue, but the CEO hadn't given the new hire the opportunity to really understand the business and his own ways of working. Communication became strained, expectations were misaligned, and eventually, it was clear that the role wouldn't work out.
It may feel initially counterintuitive - given that a founder takes this step because they are struggling for both time and bandwidth - but onboarding requires a considered effort - from both the CEO and the team. To see the gains that this function can deliver for you and your business, you need to lay the groundwork - just the same way strengthening your core sets you up better for all exercise. And it is not at all too time-consuming as you would imagine.
If a CEO office is going to be an extension of the founder and drive forward their agenda, then they need to be totally aligned. This alignment comes through deep immersion in your work and your business. Rather than viewing onboarding as a separate task, it's about involving your new hire in your day-to-day activities and decision-making processes. It doesn’t all have to fall on the founder either — bring in other departments.
This immersive approach takes time - weeks of building a meaningful connection and providing opportunities for practical learning. Egem Eraslan, Founder and CEO of Midas, bluntly talks about the reality of onboarding a chief of staff: “I spent more time with them than anyone else at that period of my life, including my family.”
Here are several effective strategies we've seen founders in our portfolio employ:
- Shadowing
Give your new hire the opportunity to shadow you for a few weeks or months. This allows them to observe how you work, understand your schedule, and ask questions in real-time. Even after this initial period, provide ongoing opportunities for them to shadow you and understand your priorities.
- Cross-departmental immersion
It is important that your hire spends time with heads of other departments, understanding their roles and challenges and building relationships, but the immersion should be deeper than this. So they understand the fundamentals of the business, have them spend a day in roles at a range of levels across the company, such as account executives or customer success teams, to gain a ground-up understanding.
- Spend time building rapport
Make time for free-flowing conversations to discuss business issues. Open up dashboards and let questions and insights emerge naturally. But beyond this, it is important to invest in getting to know each other over coffee or drinks. Personal connection can enhance communication and mutual understanding.
- Clear communication
Be transparent with existing teams about the scope and remit of the new role to avoid miscommunication or uncertainty. This means that getting the internal comms right is vital - being clear with existing teams as well as your new hire about the scope and remit of the role is essential to avoid any miscommunication.
While this can seem like a lot of time investment upfront, it's crucial to remember that this process is about integrating your new hire into your workflow, not creating additional work. The time spent now will pay dividends in the future, as your CEO office becomes a truly effective extension of yourself, capable of anticipating your needs and acting autonomously in alignment with your vision.
We have worked with founders through the process of setting up a CEO office and have seen how well it works with effective onboarding and integration. Occasionally, however, we see founders pay too little attention. Those who do run the risk that their investment in a CEO office falls short of its potential.
A CEO office that evolves with you
While it might start with a single individual, this first hire can be the anchor for a function that can scale with you and your business as it grows.
At the start, your first hire will have to wear a lot of hats as your entire CEO office. They might be following up on the actions from your meetings, while also working across business units to make sure all of the data is collated and digestible for you. They might be attending business unit meetings to ensure that the CEO’s strategic agenda is represented, while also helping to prepare for board meetings.
The inherent ambiguity of a CEO office role, Brandon explains, is something that anyone who takes it on will have to adapt to: “There is no clear linearity in a chief of staff role, so ultimately it suits people who are comfortable with that, and who can find their own areas of interests and business need that they can build into over time.”
While you can have high expectations of your first CEO office hire, inevitably they will not have every skill, and over time are likely to build specific strengths and areas of ownership. Beyond this, as the business grows, their bandwidth will become increasingly limited. At that stage, you can identify where additional hires in the CEO office might be needed to support your scaling journey most effectively.
The fundamental person requirements of your second and subsequent CEO office hires are the same as the first, although as the office grows in size, there is potential for some hires to be more specialized.
Often, this can mean hiring support in areas where the head of the CEO office feels least comfortable - e.g. data skills to support keeping track of essential numbers and projections. Or it might be recognizing that, for example, your chief of staff doesn’t have the time to focus on more intensive cross-functional projects, and hiring a strategy associate to meet that need.
Take the time to review and anticipate your most pressing needs for the next year and invest in getting the right support in place accordingly.
If you're interested in learning more about implementing or optimizing a CEO office, we're always open to discussing experiences and sharing insights on this crucial aspect of scaling leadership.
