Hiring your first head of sales can be a major unlock for you and your company. The right leader can ramp your sales team faster and more efficiently than you can and give you many hours a week of much needed time back in your schedule. At the same time though, putting additional distance between you, your customers and frontline sales reps can create misalignment if the product, sales team, and sales motion isn’t mature enough. It’s a delicate balance, and generally speaking, we lean towards staying in the role of head of sales as long as possible if you’ve been successful getting this far. Below we offer a few criteria to consider as you think through the right time to hire your first head of sales.
1 . Your repeatable sales motion actually works
In the early days you are testing the market, calling in favors from old relationships, showing up uninvited to client’s offices, and doing hand-to-hand combat to land your first sales. This is an invaluable learning experience, giving you deep insight into your customer personas, workflows and problems, and also their objections to your specific product.
Your sales motion is “repeatable” when you have established a playbook including:
- You know which decision-makers to target;
- You have a clear understanding of how long the sales cycles are;
- You know what you are you charging and why;
- You have a standard hiring profile for new sales reps;
- You have a standard onboarding process; and
- You have a standard supporting ratios for your new hires (i.e. each sales rep gets gets 1/3 of an SDR, and 1/4 of a consultant);
- You have at least 2 sales reps hitting quotas.
Once you have a “repeatable” sales motion and it actually repeats (i.e., you are regularly executing that playbook and closing clients), then you might be ready to hire a head of sales. If you’re failing on either side of that, then you likely have more work to do on your product or the sales motion.
If you don’t have a repeatable and repeating process in place before you hire a sales leader, then you will likely have no idea how to benchmark their performance. Are they not selling because it’s impossible to do so? Or because you just made a bad hire? The best to way simplify that is to take the first option off the table by crossing through that threshold yourself.
2. You have enough traction to attract an elite growth-stage head of sales
The very best growth-stage sales leaders don’t want to get caught up in finding product-market fit. They want to walk into an organization they believe has already demonstrated the ability to scale and then apply their approach/playbook to drive 10-100x output.
This means if you try to fill the role too early, you just won’t successfully attract top talent. The best candidates will shy away without demonstrable traction. Showing that you’ve closed a significant number of deals (i.e. 10+ customers, although this is dependent on your industry segment) and that that you have at least two sales rep meeting quota can be a good minimum threshold for traction.
Once you’ve achieved that, those stats will speak for themselves and you’ll of course have learned a hell of a lot about your customer pain points, your selling points and objection handling.
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