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The Chatbot Challenge review

The Chatbot Challenge publishes 198 course modules on Skool.

A review on the numbers, not an opinion: nobody here has joined The Chatbot Challenge, and nothing below is a verdict.

The Chatbot Challenge is a free Skool community, created in January 2024 and coached by Josh Rosenfeld, that teaches members to build AI chatbots for voice, web, SMS, FB, IG and other channels.[1] Its core is a free 30-day challenge to launch a VoiceAI and chatbot agency and land a first client using GoHighLevel and ChatGPT.[1]

How we measure · Report an error or ask for removal

Members
1,606
Members, last 29 days
-4
4 Oct 2026 to 2 Nov 2026
Rank by members
#1,103
of 6,074 sellers listed here
Size rank in niche
#270
of 1,230 sellers listed in content and audience building, by published members
Check the Course score
91
A, very strong
Niche
Content and audience building
1,308 listed here
Created
19 Jan 2024
Skool publishes this date
Readings
20
since 3 Sept 2026

About The Chatbot Challenge

Members get free access to more than 50 hours of VoiceAI and chatbot courses, GoHighLevel snapshots and templates.[1] Course units include Chatbot Basics, The 30-Day Challenge, VoiceAI (making and receiving phone calls with AI), an agency masterclass, and chatbot reviews, podcasts and live builds.[1]

The challenge's creator also runs Rosenfeld Marketing, LLC, whose website, rosenfeldmarketing.com, lists The Chatbot Challenge among its work.[2] The firm's main service is a fractional CTO and CMO engagement, which as of September 2026 cost $3,000 to $10,000 a month based on scope, with a $497 audit as the entry offer.[2] It also offers AI Chief of Staff, a managed AI agent that works inside a client's business, and the site says Apple was the agency's first client, in 1995.[2]

Sources

  1. Skool listing: skool.com/chatbot-challenge, as collected 26 Sept 2026
  2. Official website: rosenfeldmarketing.com, retrieved 28 Sept 2026

Compiled by Check the Course from the sources listed, to the best of our ability.

What the listing describes
NicheContent and audience buildingFormatCourseIncludesTemplates and resources

Read from the listing’s own words: what is offered, never how well.

What is inside

Course modules
198
Courses
17
Posts, all time
443
People running it
2

Counts published by The Chatbot Challenge on its own page, read on 26 Sept 2026: how much is included, never how good it is. Listed as run by joshrosenfeld.

How we knowSourced & dated
Observed on 2 Nov 2026 from Skool source page archived copy a86ba002a5d0.
Observable monthly ceiling
Not calculated

No price is published for this community, so no ceiling is calculated. Absence of a price is not a claim that it is free.

Against the content and audience building niche

Percentile among the other 1,307 content and audience building listings here, each seller counted once for size.

Size78th
smallestlargest
Check the Course Score
91AVery strong

Ahead of 91% of the 13,588 Skool communities we track, including ones without a page here, on the measures below, each read from a figure The Chatbot Challenge published itself.

  • Size 53% of the scoreahead of 88%
  • Growth 27% of the scoreahead of 38%
  • Track record 20% of the scoreahead of 93%

An algorithmic position among tracked listings: not an endorsement, a guarantee or advice. How the score works.

  • Top 25% by size in content and audience building. Measured by Check the Course.Top 25% by size in content and audience building. Measured by Check the Course.

Run this community?

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Style
Top 25% by size in content and audience building. Measured by Check the Course.
Where it goes

<a href="https://checkthecourse.com/communities/skool-chatbot-challenge"><img src="https://checkthecourse.com/badge/skool-chatbot-challenge?kind=size" alt="Top 25% by size in content and audience building. Measured by Check the Course." width="360" height="76" loading="lazy"></a>

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Evidence and signals

Listed on 1,606 members.

Evidence: measured.

First recorded
3 September 2026our first reading, not its launch
Elsewhere
Website

Tracked over time

Member change
No changeover 1 day-4-0.2%over 29 days
Price change
No price read yet

20 observations over 60 days.

Member count
1,5961,5981,6001,6021,6041,6061,6081,6101,6121,6063 Sept 20262 Nov 2026change

Observation log

Observation log
ObservedMembersChangePriceCeiling / month
2 Nov 20261,6060Not recordedNot calculated
1 Nov 20261,6060Not recordedNot calculated
29 Oct 20261,6060Not recordedNot calculated
28 Oct 20261,6060Not recordedNot calculated
25 Oct 20261,6060Not recordedNot calculated
24 Oct 20261,6060Not recordedNot calculated
21 Oct 20261,6060Not recordedNot calculated
20 Oct 20261,6060Not recordedNot calculated
17 Oct 20261,6060Not recordedNot calculated
16 Oct 20261,606-1Not recordedNot calculated
13 Oct 20261,6070Not recordedNot calculated
12 Oct 20261,607-1Not recordedNot calculated
9 Oct 20261,6080Not recordedNot calculated
8 Oct 20261,608-2Not recordedNot calculated
5 Oct 20261,6100Not recordedNot calculated
4 Oct 20261,610-1Not recordedNot calculated
1 Oct 20261,6110Not recordedNot calculated
30 Sept 20261,611-1Not recordedNot calculated
26 Sept 20261,612+17Not recordedNot calculated
3 Sept 20261,595Not recordedNot calculated
Average per week, last 29 days4 Oct 2026 to 2 Nov 2026-1
Average per week, since first reading3 Sept 2026 to 2 Nov 2026+1

Course content readings

Course content readings
ObservedPostsModulesCourses
26 Sept 2026443+819817
8 Sept 202643519817
Added per week8 Sept 2026 to 26 Sept 2026+3.300

Common questions about The Chatbot Challenge

What is The Chatbot Challenge?
The Chatbot Challenge is a free Skool community, created in January 2024 and coached by Josh Rosenfeld, that teaches members to build AI chatbots for voice, web, SMS, FB, IG and other channels.
How much does The Chatbot Challenge cost?
None of our readings of The Chatbot Challenge's Skool listing has found a price, so none is shown here, and it is not counted as free.
How many members does The Chatbot Challenge have?
The Chatbot Challenge lists 1,606 members, read 2 Nov 2026.
How has The Chatbot Challenge's membership changed?
From 1,595 members on 3 Sept 2026, our first reading, to 1,606 on 2 Nov 2026: within 1%.
How does The Chatbot Challenge compare with other content and audience building communities?
The niche median is 541 members. Pricing benchmarks by niche.
What do you get inside The Chatbot Challenge?
The Chatbot Challenge publishes 198 course modules, 17 courses, 443 posts, 2 admins. Communities with the most course content.

Alternatives to The Chatbot Challenge

Same niche, nearest in published size. Not a recommendation.