Are you structured for scale?
Scaling up is its own kind of hard. Some of the very things that got you to this current level of success have to be broken to get to the next level.
The first question to tackle is whether your business model is sustainable at scale. This is a hard look-yourself-in-the-mirror question. It takes some deliberate planning and a realistic frame of mind. Unbridled entrepreneurial optimism has to take a relatively smaller seat for this process. What is it truly going to be required to increase your business by 2x, 10x or 50x? Does that math work out as you add more customers, expand to more territories and add new products? Can you sell more with proportionally more profitability and proportionally less overhead in the long run?
After that’s out of the way, the hard changes start to come into play. What worked before may not work in the next phase. Here are some areas to consider:
what you (the CEO) actually spend your days doing
where funding comes from
how decisions are made and communicated
how work is done - processes, repeatability and flexibility all take on new meanings
right people with the right mindsets in the right seats
systems and tools needed for the job
vendors and suppliers for your products
vendors and suppliers for your business support infrastructure
what is done in-house and what is outsourced
what your customers expect from you