General
the Pitfalls of Selling to Enterprise
03/11/25, 00:00
Who is it for?
Founders and revenue leaders at B2B SaaS companies looking for practical GTM and revenue guidance.
When to use?
When you want a clear approach to a commercial problem and a practical next step.
Selling to enterprise is difficult — but not impossible. You just need to know the pitfalls.
Selling to enterprise is difficult — but not impossible. You just need to know the pitfalls.
There are three big challenges when you start selling to genuine enterprise
1️⃣ PRODUCT: non-functional requirements
2️⃣ SALES: complex, multithreaded engagements that take forever
3️⃣ SERVICE: exceptional post-sales needs
PRODUCT
- ISO27001 / SOC II
- Single sign-on; roles based access control
- ISO9001
- High availability
- Integrations: can be massive and ongoing
- Reporting and analytics
- Change control; roll-back
- Special features for special customers!
Any one of these can be a project in itself. Some enterprises will accept that some of these features are coming - available in 6 months - in other cases, if you don't have it, you can't play.
SALES
- Masses of stakeholders, many not visible
- Formal procurement processes, with silent periods
- Organisational changes confusing needs
- Internal politics
- Opaque evaluation processes
- Lack of access to key people
- Personnel changes changing requirements mid process
- Time, time, time
You need a great deal of care, focus and clarity as to when the investment is worthwhile. And honesty as to when you are flailing about talking to people who are interested in talking, as opposed to driving a process that might lead to a deal.
SERVICE
- Extremely high expectations
- Many enterprises consider themselves ‘special’
- Demands for key features and integrations post contract
- SLAs for uptime, bug fixes, responses
- Complex change management processes
- Demands for exceptional testing
- Penalties for missing SLAs
Post sales can kill the profitability of an enterprise client. You have to keep on top of it. Enterprises will typically pay for what they want - make sure you agree pre-sale what the requirements are and ensure you cost them properly.
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None of this is insurmountable, some of it can be finessed, and if you get the right deals it can be absolutely transformational. Let me konw if you'd like to discuss the details