Annual software contracts are usually presented as standard terms, and a good deal of what is in them is negotiable if you ask before you sign. Nobody negotiates after.
Auto renewal and notice
Most agreements renew automatically unless cancelled a set period before the anniversary, frequently thirty, sixty or ninety days. Ninety day notice on an annual contract means you must decide to leave nine months into a twelve month term.
Diarise the notice date the day you sign. Not the renewal date, the notice date. This one habit prevents the most common and most avoidable software cost in business.
Price uplift
Ask for a cap on renewal increases, expressed as a percentage or tied to CPI. Vendors expect this request from customers of any size and frequently agree to it. Without a cap, the renewal price is whatever the vendor decides, and the most consistent complaint in our enterprise review set is uplift at renewal.
If you can, negotiate a multi year term with fixed pricing. The discount for doing so is usually meaningful and the certainty is worth more than the discount.
Data export rights
Confirm in the agreement, not in a support article, that you can export your complete data in a usable format at any time, including after termination, and for how long after. Cloud access ends when billing ends, and businesses discover this at exactly the wrong moment.
Ask specifically about attachments. Many systems export transactional data cleanly and leave the attached documents behind, which is a problem when SARS asks for supporting documentation from three years ago.
The POPIA operator agreement
If the vendor processes personal information for you, section 21 requires a written contract. Ask for the data processing addendum by name and have your information officer read it. Check that it references POPIA rather than only GDPR, and that it commits the vendor to notifying you of a compromise.
Seat changes
Can you reduce seats mid term, or only add them? Many agreements allow additions at any time and reductions only at renewal. For a business with seasonal headcount that asymmetry is expensive, and it is worth asking whether a true up model is available instead.
Service levels
For anything business critical, ask what the uptime commitment is and what the remedy is when it is missed. A commitment with no remedy is a statement of intent. Ask also for the support response time by severity, in writing, because "priority support" means whatever the vendor decides it means.
What is genuinely not negotiable
For self service products bought with a card, almost everything above is fixed and the effort is not worth it. For anything with a salesperson attached, all of it is on the table. The rule of thumb is simple: if a human sent you a quote, a human can change the terms.