Reposting to emphasize this excellent point.
If you’ve never been part of an enterprise sales effort you need someone to help you get it going, much less make it happen. It’s a completely different world: very expensive, very slow, weird, and very lucrative if you can get it to work.
You have to sit through some pitches for this access, and it will include lots of talk about how Salesforce helps, but there is a ton of value in the exercise.
The exercise itself is its own lesson in enterprise selling.
If you want mentorship and you are a founder, I would directly message early VP's of sales and ask for help. Also, read the great Saastr blog by Jason Lemkin.
If you mean “show the inner workings” then just say that.
And for enterprise sales there's a whole vocabulary and model to learn: your coach, understanding who has the signoff, when you're talking to someone who will waste your time -- and when someone who seems insignificant but is actually the decision maker, how to structure the deals. And how to hire, manage, and incent (mostly but not exclusively financially) them.
Any suggestions regarding how much earlier?
In one market, let’s say there are 1,000 customers who are small companies themselves and who will each pay $10,000 per year to use your service. And then there are 100 companies who are big and will spend $100,000 per year. The little companies are simple sales and buy using their credit card. The big companies are a complex sale and require a top down approach with complex approvals.
You can win the first 1,000 customers organically, but because not everyone is ready to buy all at once, let’s say it takes 5 years to win them all - in other words you’re adding 200 x $10,000 = $2M of new ARR each year. By the way, this would be a fantastic market all by itself.
But sadly, with each passing year, your organic growth from small customers brings a lower percentage growth rate. $0 - $2M is exciting and so is $2M - $4M. But $4M - $6M is only 50%. And $6M - $8M is only 33%...
If you want to keep up 100% annual growth, you’re going to need to bring in some big customers starting in year three so that you can go from $4M to $8M instead of just $4M to $6M. To win that extra $2M in ARR, you’ll need 20 large customers along with the 200 small customers from organic growth.
Now, I don’t know what your market looks like, but I’d say that the time to bring in top down sales is around when you’ve found product market fit as evidenced by steady organic growth. If you are getting repeat sales from small customers who are really happy with your product, then, chances are, big customers would love to have what you make too. They just have to be sold to.
In other words, I would not wait. Start doing top down sales as soon as your product is hitting its stride with repeated happy customers.
From personal experience, top down selling is very hard to get right. You suddenly have to learn how to make a sophisticated business value proposition rather than just saying, “here’s my stuff. It’s really great. Look who else is using it.”
It’s also hard to find good people to lead enterprise sales, particularly if you’ve been a product led founder and don’t know what good enterprise sales looks like. It’s definitely an inflection point with a lot of risk for bad execution.