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Your AI Agent Org Chart: When to Split Roles, When to Combine Them

16 September 2026 · 3:00 PM UTC · 1 hour
Decide when two agents beat one: the McMahon/Brian split (same data, different lens)Decide when one agent beats three: the Rancho combine (strategy + functional + build)Read a system prompt and skill list to spot where the boundary should sitAssign a human manager to each agent, and know what that role actually doesSketch your own agent org chart before you write a single prompt

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21Days
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Most teams either give everyone one AI assistant or spin up a bot per task. Both are wrong. See the real decisions behind Kowalah's own agent team — where we split, where we combined — so you can sketch your own agent org chart before you build.

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Overview

About this webinar.

Most AI programmes start with a headcount question dressed up as a technology question: how many agents do we actually need? Get it wrong one way and you build a single assistant trying to be everything to everyone. Get it wrong the other way and you end up with a sprawl of single-task bots nobody can manage.

Kowalah runs its own go-to-market on a team of named AI agents, and we've made both calls in public. John McMahon (our CRO agent) and Brian (our AE agent) look at exactly the same deal data — but McMahon owns pipeline-level judgment and Brian owns deal-by-deal execution. Same source, different lens, so they stayed two agents, not one. Rancho, our delivery consultant, does the opposite: in a human team, strategy, functional consulting, and technical build would be three separate specialists. One agent handles all three, because there's no handoff cost between them the way there is between people.

What you'll see:

  • The real system prompts and skill lists behind McMahon, Brian, and Rancho — not a diagram, the actual configuration
  • The split test: same data, different lens means two agents
  • The combine test: no coordination cost between the skills means one agent
  • What a human manager actually does for an agent day to day, and why every agent needs one

Who should attend:

COOs and Heads of AI/Ops designing their first — or fifth — AI agent. Functional leaders about to write an agent's job description and unsure whether it should be one agent or three.

What you'll leave with:

  • A working framework for deciding split vs. combine before you build anything
  • A one-page agent org chart template you can fill in for your own team

Agenda

What we'll cover

01

Split or Combine? The Kowalah Agent Org Chart

15 minutes

Charlie narrates through real system prompts and skill lists from Kowalah's own agents — including the McMahon/Brian split and the Rancho combine — and the decision framework behind each call.

02

AI in the News

15 minutes

Latest AI developments and releases from the past week

03

Q&A

30 minutes

Open forum for questions about your specific use cases

Total duration: approximately 30 to 45 minutes.

Charlie Cowan

Your host

Charlie Cowan

Founder, Kowalah

Charlie hosts our Wednesday Webinars, sharing practical AI strategies and insights to help organisations accelerate their AI adoption. With deep experience in AI leadership and implementation, he gives executives and teams actionable guidance for navigating AI transformation.

Ready when you are

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