Cross-sell efficiency depends on either product adjacency or overlapping buyer personas. Resourcing structure, processes, incentives, enablement, and business rhythm come next once you have enough proof from your customer base showing early signs of cross-sell. First, look for those signs. Identify customer segments where cross-sell is already happening. Talk to sales, support, and customer success teams involved in these deals. Review transcripts and CRM notes to scale insights. After this, you will get a sense of what’s driving cross-sell—product adjacency or advocacy, where one department trusts champions in another.
When driven by product adjacency, the pace can increase dramatically by removing friction around discovery, evaluation, and value finding. This can be product-led (PLG motion). When driven by customer advocacy, the sales motion needs to be sales-led. Look for introductions and patiently wait for contract renewal dates if there is an incumbent. Sometimes you may need to wait for the incumbent to grow complacent and make a mistake.
In either case, robust analytics and deep customer knowledge are required. CFOs and leadership will always support these initiatives, and budget won’t be a problem since this is one of the most cost-efficient ways to grow revenue. However, you need to show that it works, share your understanding of roadblocks, and explain how you will deploy resources to remove them within a time-bound plan. Generating enough pipeline for an AE or AM to hit their quota through cross-sell is the main challenge. Therefore, a separate qualification engine or team to evaluate and transfer these opportunities to the cross-sell team is essential. Set the expectations right (temper leadership expectations especially when you are fine tuning operations). Speaking from my experience at Freshworks. Let me know if you need help building the case.
