---
title: "Jack Taubl"
description: "Jack Taubl, Director of Sales at Ocean.io, on Pipeline."
url: "https://thepipelinepodcast.com/guests/jack-taubl/"
image: "https://thepipelinepodcast.com/og.png"
---

[Guests](https://thepipelinepodcast.com/guests/)

# Jack Taubl

Director of Sales at [Ocean.io](https://ocean.io/)

[Jack Taubl on LinkedIn](https://www.linkedin.com/in/jack-taubl-14561a76/)

## On Pipeline

-   [Why Does AI Prospecting Get Worse the Longer You Use It?](https://thepipelinepodcast.com/episodes/why-your-ai-gets-worse-the-longer-you-use-it-with-jack/)

    Episode 1 · Oct 7, 2026

    AI prospecting gets worse in long chats for two reasons: models are built to compact context, and vague prompts drift. Jack Taubl, Director of Sales at Ocean.io, explains both on Pipeline, along with his fixes. He works inside Claude…

    ### Key takeaways

    -   Do open-ended prospecting work inside a Claude project, where each new chat carries context from the others, instead of one long thread that gets compacted.
    -   When Claude gives an answer you don't trust, open a separate chat in the same project and consider a different reasoning model, as Jack Taubl does.
    -   Replace prompts like "What does a good XYZ look like?" with specific requests, because ambiguous questions get ambiguous results.
    -   Ground a proposal by adding the prospect's most recent 10-K to the Claude project's files.
    -   Schedule a daily briefing to run before your day starts. Jack Taubl runs his at around 4:00 a.m.

    ### In Jack's words

    > "it's fundamentally designed to erode the longer you use it if you're staying in a single chat."
    >
    > [At 02:03 in the episode](https://thepipelinepodcast.com/episodes/why-your-ai-gets-worse-the-longer-you-use-it-with-jack/)

    > "if you ask ambiguous questions, you're gonna get ambiguous results."
    >
    > [At 02:42 in the episode](https://thepipelinepodcast.com/episodes/why-your-ai-gets-worse-the-longer-you-use-it-with-jack/)

    > "I will immediately switch to a separate chat and potentially switch the reasoning model that I'm using as well"
    >
    > [At 04:12 in the episode](https://thepipelinepodcast.com/episodes/why-your-ai-gets-worse-the-longer-you-use-it-with-jack/)