Apero Advisors

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The future of GTM data and AI agents

Apero Advisors Podcast/Harris Kenny, OutboundSync/

Apero Advisors Podcast/Nov 2, 2026

Episode 3 of the Apero Advisors podcast. Benyamin Holley sits down with Harris Kenny, founder of OutboundSync. Harris shares how his CRM consulting agency led to a product that syncs cold email activity into the CRM, how he found his first customers, and why he is rethinking what a small software company should build now. They talk about the shift from the old bootstrapped SaaS playbook to products built for AI agents. Harris explains why he thinks data waterfalls hide bad sources, why a high fill rate does not guarantee good data, and what it would look like to give customers an answer they can trace back to its source.

Notes

  1. 01

    OutboundSync started from Harris's CRM agency work, syncing cold email activity into the CRM.

  2. 02

    He talks about finding first customers and asking people what they will buy, not what they think of an idea.

  3. 03

    The old bootstrapped SaaS playbook is changing, and he is building products that get better as AI gets better.

  4. 04

    Data waterfalls can hide bad sources: a high fill rate does not guarantee good data.

  5. 05

    He describes a different approach that traces an answer back to its source.

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