Problem

David Herkovitz, a Strategic AE at Dole, sold B2B cloud-based supply chain software for logistics firms managing the movement of fresh produce from farm to shelf. The buying committee was wide and technical: VP of Operations, a supply chain technology lead, procurement, sometimes a food safety or quality stakeholder. Deal cycles were long, and freshness created real urgency on paper, spoiled inventory is a hard dollar loss, but that urgency rarely showed up in his deals as a forcing function. Deals stalled in evaluation. He was single-threaded more often than not, closing the relationship he had rather than mapping the one he needed, and pipeline reviews told him a deal was "in POC" without telling him whether it was actually moving or quietly dying.

Solution

I worked with him through three full 12-week cycles.

Skills: Discovery wasn't surfacing the real cost of the status quo. Spoilage, manual tracking errors, and compliance exposure were treated as background context instead of quantified impact tied to a specific buyer. We rebuilt his discovery to end every call with a number: what does the current process cost this account annually, in spoiled product, in labor, in compliance risk. No number, no advance to the next stage. We also built a multithreading standard: minimum three stakeholders identified and engaged before a deal could be called qualified, since a single-threaded relationship in a committee this wide was the single biggest reason deals went quiet.

Pipeline management: Quota $550K, average deal size $45K, win rate 22%. That backsolves to roughly 15 deals a year, 66 qualified opportunities at that win rate, and a required coverage of 4.5x remaining quota. He'd been tracking deal count, not deal value against that ratio, so a pipeline that looked full was actually thin once weighted against a realistic win rate. Coverage became his weekly instrument: below the line, the week's priority was new opportunity generation, not more time in existing POCs.

Consistent execution: Weekly review, same slot every week. Score lead measures (new multithread contacts added, discovery calls that produced a real cost number, next-step commitments secured from the buying committee, not just from his main contact). Check coverage against the 4.5x line. Name the one constraint that stalled a deal that week and remove it before the next review, rather than letting it carry forward unexamined for a full quarter.

By the end of the cycle, deals that used to go quiet in evaluation had a name attached to every stakeholder and a number attached to every case for change.