How AJ closes complex enterprise deals with Olli

The meeting had not gone well. A technical lead at one of the biggest names in global fintech watched Honeycomb's team demo features he was already walking away from — and said so. AJ Kurtz had one shot to recover the relationship, and it had to land perfectly.

Before Olli: Brute-Force Context

AJ is a strategic AE focused almost entirely on cold outreach. No pool of warm inbounds, no repeat-purchase motion — just the daily work of getting the right message in front of the right executive at the right moment. Before Olli, that meant hours of manual synthesis: reading LinkedIn profiles, archiving blog posts, stitching together call notes, then sitting down to write something that didn't sound like every other email in the prospect's inbox. Quality over quantity was already the philosophy. The bottleneck was time.

Then he started working with Olli.

The Olli Experience: Speed Without Sacrificing Judgment

The shift wasn't about offloading the thinking — it was about offloading the synthesis. AJ still identifies the right context: the prospect's LinkedIn presence, recent posts, past call transcripts, Gong recordings. But instead of spending hours turning that raw material into a tight five-sentence LinkedIn message, he hands it to Olli. "Olli is the best writer," he'll tell his team. Not because it's the flashiest LLM — because it stays professional, stays true to the message, and doesn't try to be clever when clever isn't what closes deals.

That distinction matters in his market. Executives at financial services firms aren't looking for witty openers. They're looking for someone who actually understands where they're going. Olli gives AJ the output that gets him close to right on the first pass — and that changes the economics of outreach at scale.

The Playbook: Context First, Always

AJ runs two main Olli plays. The first is account plans — dropping in deal history, call recordings, and desired outcomes to generate a starting framework that he then edits down into something precise. The second is LinkedIn messaging. When he's earned a direct connect with a target executive, he treats it like one shot. He loads Olli with everything he knows about that person — their team's conversations, the initiatives they're tied to, the signals from job postings or public posts — and asks for a message that's brief enough to actually get read. For Honeycomb's observability day in New York, that playbook helped him get five target accounts in the room and into real conversations with Honeycomb executives.

The Human Layer: What Olli Can't Do

The fintech recovery story is the clearest example of what AJ brings that Olli can't. It was three days of thinking — understanding exactly how this director's technical priorities had evolved, where Honeycomb's demo had created the wrong impression, and what would actually rebuild trust with someone of that caliber. Olli helped sharpen the message. But the judgment — what to say, what to own, what to reframe — that was AJ. "I always go in and edit after the fact," he says. "There's never a situation where it's totally baked." The tool is a multiplier. The rep is still the rep.

"Get the full breadth of what might move the needle," he'll tell anyone who asks. Then let Olli help you get it down to something a busy executive is actually going to read.