Stage: $10-40M
The team has worked well cross functionality to deliver the first $10 in ARR. No small feat. Customer signals on pain you are solving, understanding of your value proposition, early customer champions are found - you feel as though you have Product-Market fit, which can change:). But maybe you got there with 1-2 superstar sales people. Often at the end of a month or quarter - saving the company at the closing bell to meet or exceed targets. A bit scary but more common than you are led to believe.
As the CEO, the question rages in your mind. Do I have the right person(s) in my Sales leadership to scale. Can we grow 100% next year with this team and leadership? What does scale mean and look like for us? Now aptitude and coaching become the dominant traits you need in your sales leader. Below are some critical attributes of the person who will take you from $10M and beyond. Perhaps you have that leader already, but some suggestions to stress test that theory before making a leadership change.
Do you know precisely who your ideal customer profile is and why they buy? Seems basic but one might be surprised:).
How do you qualify potential customers in or out, and customers to expand (NRR)?
What is their plan to further reach that customer demographic?
Do they have a sales process that one can repeat to achieve?
In hiring, have you crafted a "Ideal Sales Person Persona" - ISPP?
What is the strategy to acquire the talent above (ISPP) as you scale?
Understand their views on manager level hires, get help assessing.
Sales training and enablement - Does this exist? Do you own a sales playbook? If not, time is your enemy.
Data - Has she instituted key KPI's, measured frequently depending on cycle, rigor of using metrics in performance reviews, building of a funnel with marketing and channel (tops down/bottom up)? Is reporting transparent to all?
What is the strategy to grow ASP and NRR, is it well defined and clearly communicated?
People Management - have they moved out under-performers. And done so in a professional manner.
This is a primer to stress test, do I need to go acquire the next stage sales leader. More often than not it will be a different leader than your earlier stage but do not fall victim to pattern matching or broad stroke conclusions. Stress test the above areas. And if your conclusion is yes, we need a new sales leader for our next phase of growth, the above thinking will better equip you to design the role and expectations.
