I currently sit in three different boxes on our leadership Accountability Chart: Visionary, Head of Sales, and Head of Finance. We finally have cash flow to hire, but how do I prioritize which seat to give away first so that I do not derail our operations or hire the wrong profile?

Question

Tyler Smith · Accepted Answer

Holding three major leadership seats means you are running three different playbooks at half-capacity. To decide which seat to shed first, you must run an objective diagnostic based on revenue risk, your personal energy, and the ease of hiring.

Start by listing the five roles for each of your three seats: Visionary, Sales, and Finance. Score yourself honestly using GWC. In which seat are you merely surviving, and in which seat do you create explosive enterprise value? Most founders excel at visionary market moves and high-level enterprise selling, while treating finance as an exhausting compliance exercise.

Next, evaluate which seat carries the highest operational risk if you step out tomorrow. In growth businesses, giving up sales too early can stall revenue if the sales process is still trapped in the founder's head. Conversely, holding onto the finance seat when you lack genuine financial expertise results in poor cash management, weak pricing models, and ugly balance sheets that repulse buyers.

Follow this three-step sequence to delegate:
- Step one: Shed Finance first if your financial reporting is reactive. You can hire a strong fractional CFO or controller to build cash visibility and financial controls without disrupting customer acquisition.
- Step two: Document your proprietary sales process and convert your tribal sales knowledge into a repeatable pipeline. Once documented, hire a true Head of Sales to own execution.
- Step three: Elevate permanently into the pure Visionary seat, partnering with your Integrator to drive strategy, big relationships, and long-term valuation levers.