A scaling B2B software company had a strong internal sales lead ready to step up, but the board was pushing hard to hire an external VP of Sales. The founder brought the call to Alfred. Rather than pick a side, Alfred laid out the org-design tradeoffs of each path, benchmarked the comp on both an internal promotion and a market VP hire, and named the real risk on either route — so the decision was made on evidence, not pressure.
The reasoning
The hire-versus-promote call is rarely about the candidate: it is about the shape of the company you are building. Hire an external VP and you buy proven playbooks and speed, but you risk a culture clash and a long ramp; promote from within and you protect trust and context, but you stake the number on an unproven leader. The real risk sat in the gap between the two — and that is where Alfred focused.
What did that mean in practice?
Org design first
Before naming a person, Alfred mapped the role the company actually needed — scope, reporting lines, and the shape of the sales org a year out.
Comp benchmarked
Alfred priced both paths against the market — base, variable, and equity — so the founder could see the true cost of a senior external hire versus an internal step-up.
Risk made explicit
Every path carries a downside. Alfred named the failure modes of each — ramp risk, culture risk, retention risk — instead of letting them stay unspoken.
The team came first
Whoever took the seat, the existing sales team had to stay motivated. Alfred weighed how each choice would land with the people already doing the work.
