Leadership alignment
Early-stage company assessed for first institutional hire decision
B2B Software · Seed/Series A
The challenge
The founding team of three was preparing to make its first institutional hire — a VP of Sales — using Series A capital. The Series A investor had strong views on the profile required. The founders had a different view. Before the process began, both parties needed an independent assessment of the organizational gaps the hire was intended to fill and the cultural fit requirements that a successful candidate would need to meet.
What Wexler Gray surfaced
Parallel assessment at this early stage focused on leadership alignment and commercial clarity: both scored significantly below typical benchmarks (43 and 38 respectively), which operators contextualized as normal for a pre-Series A team but important to understand before hiring into the gap
Operator assessment identified that the founding team's primary commercial gap was not sales execution per se, but commercial infrastructure — the company had no systematic approach to pipeline management, pricing authority, or customer success, meaning a VP of Sales would need to build systems rather than simply manage sellers
Bearing interpretation identified the key hire profile insight: the company needed a VP of Sales who was a builder rather than a scaler, and who could operate without the formal support infrastructure that a more mature business would provide — a significantly different profile from the one the Series A investor had initially proposed
Outcome
The founding team and Series A investor agreed on a revised hire brief based on the Bearing insight. The VP of Sales appointed was a proven commercial builder with early-stage experience, rather than the scale-stage commercial leader the investor had initially preferred. The company hit its Series A commercial milestones within 12 months of the hire.
Engagement brief
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