Early star hires and the Cristiano Ronaldo moment at scale-up stage.
Cristiano Ronaldo is one of the greatest football players of all time, an extraordinary competitor and leader for Portugal. However, age eventually rendered him a tactical liability on the pitch while he remained a commercial asset for the Portuguese Football Federation.
A web of political interests emerged:
Ronaldo leveraged his personal brand to demand starting status while refusing to accept physical limits.
Former Portugal coach Roberto Martínez used Ronaldo as a shield for political protection, while Ronaldo relied on him to secure guaranteed playing time.
The federation protected its direct financial interests.
These political interests aligned until a new coach arrived, a fragile compromise was negotiated, and a status change occurred that led to open conflict and the departure of Ronaldo.
This type of dynamics can hit scale-ups when early star hires no longer belong in the starting lineup. Early employees build the MVP, secure initial revenue, and drive early survival through passion and speed over perfection. However, once a company passes 30+ employees, those same traits turn into liabilities unless the profile morphs alongside the business. They must accept that the old playbook no longer applies.
When these early hires possess deep internal networks and direct backchannels to founders, a dangerous parallel forms. If they fail to evolve, informal power dynamics shortcut the ultimate goal: building the best product and driving real return on investment. Rather than driving progress, they turn into legacy custodians: guardians of a past that once enabled change, but now actively prevents it. They bypass new leadership, fuel internal politics, and sabotage scalable ways of working.
At this critical juncture, legacy achievements and personal affinities must take a back seat to collective performance and future growth.
Managing Human Capital and Transitions
Just as in sports, founders must step into the role of a true manager, or delegate these difficult conversations to a fractional managing director who focuses on the human aspect of the company and holds transparent, direct discussions.
There are two primary paths for a former star who has grown alongside your company:
Propose a new, clearly defined role: Be explicit about the new mission and the requirement to operate differently.
Acknowledge departure as a valid option: If the shifted role or reporting line is not accepted, parting ways becomes necessary.
As a founder, delaying this decision to avoid short-term friction only endangers the future of the entire company.
Managing Titles Before You Build
To prevent this friction, manage titles and expectations carefully from day one.
Just as with founding equity, never over-distribute senior titles or over-promise roles, because you will inevitably need to hire external leadership for your next stage of growth.
When hiring early, stick to two sustainable paths:
Hire high-potential talent who can scale their capabilities alongside the company.
Hire experienced operators with a mutual understanding that their mission will ramp down while the company is growing.
Title responsibilities and skillset expectations must be managed as carefully as equity allocation.
Remember, do not fall into the trap of the Portuguese Football Federation or the new Portugal coach with Ronaldo. Be crystal clear about expectations from day one. A startup role is fundamentally different from a scale-up role, and you must communicate this distinction explicitly from the start.
When It Is Already Too Late
If you are already past this point, you are due for a product operating model audit that maps both formal and informal dynamics:
Decision-making authority
Communication flows
Ownership, responsibilities, and accountabilities
This diagnostic will very likely point to a product organisation restructuring.
And you? Would you have kept Cristiano Ronaldo on the pitch? Convinced him to stay on the bench? Or left him at home entirely?
