I want to tell you my favorite Enterprise product story and some of the great people who helped make it happen.
When I joined Typekit, I worked on Typekit Enterprise. Typekit was a SAAS thing that designers used and loved.
Typekit Enterprise was much like the regular product. The primary difference was a written contract instead of a EULA, and a yearly invoice instead of monthly charge. That will sound familiar to my enterprise product managers.
We had a contract that I remember being about 1,000 pages long but was probably about 6. Don Loeb and I had our hands full sending out contracts, getting back redlines, and sending them to our lawyer.
I think we were closing about 3 or 4 deals per quarter when I joined. I remember that revenue from individual sales was skyrocketing, but Enterprise sales were pretty flat.
Why? We looked back at our track record. We pulled out all of our contracts, and we dug up all of the email. We figured out that it was taking anywhere from 3–6 months to close a deal from the day we made first contact with a customer to the day the deal closed.
For individual customers, we already had amazing product-led growth. Enterprise clients didn’t need much more hands-on selling than our free trial gave them. Sometimes we’d extend the trial or provision a handful of extra accounts.
It was primarily the pinging and ponging of that stupid contract that was taking forever. And it was also costing us money in legal fees to send those redlines to the lawyer for them to review.
I remember telling my boss Bryan Mason “This contract is the enemy!” He bravely encouraged me to get rid of it. And our CEO Jeffrey Veen probably said something like “What he said 👉.”
My idea was to replace it with a one-page PDF order form that enterprise clients could use to configure their order.
My colleague, legendary designer Jason Santa Maria made me a pretty slick form. It turns out if you work in the business long enough you may get famous designer to make you an enterprise sales order form. This was a bigger accomplishment for me than it was for him.
It did not go smoothly at first. Every customer initially said “My legal will not sign this, they insist on making their own modifications.” And for a while I believed them. I despaired at my foolishness for thinking I could make big companies behave like regular people.
I had an idea. I started to respond “No problem! Here’s a contract you can redline. There’s a minimum fee to go this route of $50,000/year. The PDF no-negotiate version is $8,999.”
When presented as “Vendor doesn’t meet legal requirements” we lost the deal. When it’s “Save our company $42k by making a smart business decision” it was a no-brainer.
Deals started closing quickly. I think we eventually hit a pace of about 20 deals/quarter. Eventually I hired Meghan Rand (who I have learned so much from) to take over that business and she made it grow and thrive.
Since then, every Enterprise customer relationship started with that form. We eventually stopped selling Typekit any other way. Typekit was acquired by Adobe, and became Adobe Fonts. It’s now included as part of Creative Cloud and Creative Cloud Enterprise.
Here’s the moral: Something that you think is a requirement, when you look up close, is really just an incentive. You can’t tell them apart until you’ve become an expert in the customer and the sales process.
If you embed a product manager in the enterprise sales process, you can make your enterpriser product much more product-led than most people think. More on that another time.