In the “old” days, there was a rough rule that as soon as you are bringing on more than 1–2 reps a quarter, you needed to hire a director of sales ops.
That at that point, at a minimum, there would be too much administrative work for your VP of Sales to handle it herself.
That still is probably a good rule.
But time has marched on and we’ve all learned more specialization in sales is better. We want openers opening, closers closing, upsellers upselling, success managers focused on success, etc. In the end, this leads to more efficient revenue and thus more revenue.
As part of that, we’ve realized that hiring a sales ops professional as early as possible is usually a very high ROI investment.
Capital permitting, I’d make the hire as soon as you have one manager + 4 other folks on the sales team. That team will soon enough double. You want the sales ops help scaled up and helping before then. At a minimum, I’d make the hire once you have 8 sales reps.