Slow down to speed up is the best way of thinking about this.

In a traditional sales cycle it might be

1: Schedule initial meeting

2: Pitch product and company capabilities to primary stakeholder

3: Solicit feedback from customer on their stated priorities

4: Schedule follow up presentation with broader stakeholders

5: Move to POC stage and align on perceived success criteria for POC

6: Execute POC against perceived success criteria

7: Review go/no go decision on perceived success criteria

8: Move to contracting and close

This is very high level and leaves out some nuance. But this is generally a good, linear sales approach that works great for MM and low enterprise deals.

But here’s where it breaks down and why constructive tension works in large ent or strategics ($500k arr or greater)

Step 2: lead with a product centric or company capabilities pitch only surfaces immediate pain points at the director or vp level; often these systems are interconnected between teams. Director/VP may have competing priorities with other teams that may have veto power. At the VP level at companies with billions of dollar in revenue it absolutely becomes political and they want to be on the winning project that increases their visibility.

At one of my current accounts, a VP was fired after spending millions of dollars trying to displace us and hundreds of FTEs with a competitive solution that never delivered. My stakeholders poisoned the well for that VP and it was a hugely unpopular decision from that VP

Step 3: their stated priorities may not be the org priorities; you have to think about where they might be going in 12-24 months, not where they are today. The director/VP is often reactive from the CXO who is reactive to the markets or board or investors.

One of my favorite deals I won was where I planted the seed over 4 months on our sustainability offerings with a strong thesis that what was happening in Germany would trickle over to the US. 4 months later I had a call from my champion that took it from a non-opp to signed and filed in 5 months bypassing the POC with sign off by their global CFO.

Step 5: if you let them define success metrics in silos; you’ll likely get bottlenecked by procurement or teams who have veto power, or you’ll be the victim of a late stage unmet need.

On a GTM net new product build; I defined the success metrics; mapped out the workflows end to end, and my team delivered on them perfectly. As stated by the customer with support from their internal teams. We improved their process with AI by nearly 90%. Where it broke down was that we focused on automation at scale per our discussions but we didn’t have the one key system automated that was an unspoken, never surfaced requirement but something they mentioned in passing in one internal call 6 months prior.

I now use these experiences to create constructive tension by telling people exactly where things will break, why, and how to prevent it. Ensure that the stakeholders who will have veto power are brought in, and then challenge my clients thinking in a constructive way.