I've been spending quite a lot of time recently looking at businesses that are starting to see a bigger enterprise opportunity. Some have built successful SMB or mid-market businesses and are beginning to move upmarket. Others have already won impressive enterprise customers, often much earlier in their development.
Both can arrive at the same problem. The business has proved enough to know that enterprise matters without necessarily having worked out how to repeat it.
For a successful mid-market business, the temptation is to take what already works and move it upmarket. But enterprise customers bring different buying groups, greater complexity and often require the proposition to work harder. At the same time, the existing commercial engine is still generating today's revenue. Taking your best people away from it to build something less proven carries obvious risk.
The other route starts with enterprise customers already being there. Those early wins might have been driven by founders, exceptional relationships or a huge amount of senior leadership involvement. The customers and revenue are real, but winning the first few enterprise customers and building a repeatable enterprise sales motion aren't quite the same thing.
There is an awkward stage between proving that enterprises will buy and being ready to scale an organisation around them. It's tempting to jump quickly to whether you need enterprise salespeople, a VP Sales or a CRO. Sometimes the answer will be yes. But it's worth understanding what you're asking them to build first.
For me, there are six practical questions worth answering.
Where should we focus?
Enterprise markets get very big, very quickly. A long list of companies might theoretically buy the product, but a small number of well-chosen accounts will probably teach you far more. Where do you have a genuine reason to win, and which customers could help establish something bigger?
Is the proposition ready?
A successful point solution doesn't automatically become an enterprise proposition by selling more of it. Larger customers bring different buyers, broader problems and often an opportunity to create considerably more value.
Can we repeat what's already working?
Founders and exceptional sellers carry a huge amount of context in their heads. They know the stakeholders, the politics and how far the proposition can flex. The challenge comes when the next five people need to make those judgements without them in the room.
Are we equipped to win larger deals?
Enterprise opportunities involve more people on both sides. Product, technical teams, executives, legal, procurement, security and partners can all become part of the deal. Somebody needs to keep those moving parts aligned around the customer.
Who has the capacity to build it?
Building a new commercial motion takes real work, while the same people are often being asked to deliver an aggressive number through the existing business. However good the team is, there are only so many hours in the week.
What capability do we need next?
The existing team may be able to evolve. You may need additional enterprise experience, or the opportunity may justify a permanent commercial leader and larger team. That decision becomes easier once you've learnt enough about the motion you're trying to scale.
None of this means spending a year designing the perfect enterprise model before starting to sell. Most of the answers come from working with real customers. You learn where to focus by pursuing accounts, sharpen the proposition through actual conversations and discover what's missing by trying to execute.
The first enterprise customers tell you there is an opportunity. The next stage is working out how to win them without needing the same people, circumstances and effort every time.
