Building, selling and deploying software for enterprises is really, really hard work.

This is for many reasons. 1 key reason is that they have a lot of "Enterprise requirements" that small and medium businesses typically do not. For example...

Business Requirements
- Deep configurability of some key features/workflows
- Integration into existing enterprise tools
- Co-branding considerations
- Analytics/reports
- Enterprise pricing plans
- Customer support and system SLAs (and methods of measuring)

Technical Requirements
- API for integration into custom systems
- Security (surviving PEN test)

Internal Concerns
- Threat/fraud modeling at scale
- Scalability (including 3rd party rate limits)
- Resiliency/uptime
- Monitoring for all of the above

But here's the thing.

Most people's intuition and experience would lead them to try to find the "Venn diagram overlap' between the requirements of all their enterprise clients and get those requirements done first.

This might seem intuitive and logical, but it is wrong.

Instead, you should...

1. First, ensure you are selling to the SAME kind of customer, trying to solve the SAME use-cases for the SAME reasons. You should define 'Same" very narrowly. Uncomfortably narrowly. This is because customers, use-cases, and intentions that might seem similar can actually be wildly different in terms of product and business requirements. If you get this wrong you will never properly productize and scale your offering.

2. Recognize that, for each customer, their circle of blocking requirements are all blockers for them. They don't care about the Venn Diagram Overlap. They care about their circle. Also, recognize that you want to get customers up and running as fast as possible (to get case-studies, revenue, and momentum on the board.

Given this, work diligently to...

a) Stack rank your clients and choose which will go live first, second, third, etc

b) Work closely with your clients to make their circle of blockers as small and precisely scoped as possible

You need to push HARD here. Question their real concerns/pain vs. what they THINK they need. Be careful about requirements that might break your business (E.g. Whitelabel for a b2c/b2b2c product should be a non-starter)

c) Work closely with your clients to try to make their circle of blocking requirements overlap as much as possible with other clients - not for the purposes of prioritizing those overlapping items, but for the purpose of minimizing the total set of items inside all the circles.

d) Work on one circle at a time and get each client up and running one by one.

e) Manage expectations with everyone and keep clear and constant communication. Use project plans and Gantt charts if you have to.