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Round of 16 / Matchup 6
AI Marketing Madness
Voting Closed

The Pipeline Battle

Both plugins grow your business by reaching new people. One builds an owned newsletter audience. The other arms you for 1-on-1 sales conversations. Scale vs precision. Only one moves on. Watch both demos and decide.

Letter Wingman

by Corey Koehler
Built for content creators who have a sizable audience on platforms like YouTube, LinkedIn, or TikTok but haven't yet launched a newsletter to own their audience. Walks through three steps: creating a lead magnet, setting up your newsletter home base, and landing your first 50 subscribers. Includes an audience value estimator.
Built for content creators who have a sizable audience on platforms like YouTube, LinkedIn, or TikTok but haven't yet launched a newsletter to own their audience. Walks through three steps: creating a lead magnet, setting up your newsletter home base, and landing your first 50 subscribers. Includes an audience value estimator.
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VS

Prospect Brief

by Jeff Jenkins
Turns prospect research into ready-to-use sales briefs. Give it a company website, LinkedIn page, and job postings. It synthesizes pain points, generates discovery questions tailored to their situation, matches your services to their needs, and builds a polished HTML one-pager to screenshare.
Turns prospect research into ready-to-use sales briefs. Give it a company website, LinkedIn page, and job postings. It synthesizes pain points, generates discovery questions tailored to their situation, matches your services to their needs, and builds a polished HTML one-pager to screenshare.
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Winner
Letter Wingman
advances to the next round
Scouting Report

The Full Breakdown

Winner
Letter Wingman
by Corey Koehler

You built an audience of thousands on YouTube or LinkedIn or TikTok. Congrats. You also built it on someone else's land. One algorithm change and your audience vanishes. Letter Wingman gets you off the rental platform and into ownership with your own newsletter.

It interviews you, builds a quick brand profile, creates a lead magnet, sets up your newsletter home base, and writes your first welcome email. Then it gives you a day-by-day plan to land your first fifty subscribers using scripts tailored to your specific platform.

There's even an audience value estimator that shows you what your subscriber list could be worth. Because nothing motivates action like seeing the revenue you're leaving on the table.

  • Brand profile interview: analyzes a sample of your existing content to capture voice and style
  • Gathers niche, audience details, and desired transformation
  • Step 1: Creates a lead magnet concept based on your existing content (or sets up a waitlist)
  • Generates lead magnet copy and a one-liner for promotion
  • Step 2: Newsletter home base setup with a checklist and embedded tutorial video
  • Writes a ready-to-paste welcome email
  • Step 3: Subscriber acquisition plan with platform-specific scripts (YouTube, LinkedIn, TikTok)
  • Day-by-day outreach plan: warm contacts, announcement posts, DM templates
  • Audience Value skill estimates potential revenue using industry benchmarks for your niche
  • Revenue ideas: sponsorships, paid tiers, and other monetization paths
Prospect Brief
by Jeff Jenkins

You're about to hop on a sales call. You've got a company name and a LinkedIn profile. That's not enough. Prospect Brief takes those raw inputs and builds a polished one-pager you can screenshare during the call. Pain points mapped. Discovery questions tailored. Your services matched to their actual needs.

It even scans job postings to pick up signals about what's really going on inside the company. Because what a business is hiring for tells you more than what their About page says.

Walk into every call prepared. Walk out with a prospect who just watched you understand their business better than the last three agencies they talked to.

  • Five skills: profile setup, source collection, analysis, brief generation, and document output
  • Input sources: company website, LinkedIn profile (copy-paste), job postings, recent news, CRM notes
  • Synthesizes pain points from multiple data sources
  • Generates tailored discovery questions based on the prospect's specific situation
  • Matches your services to identified needs and opportunities
  • Produces a prospect-facing HTML one-pager designed for screensharing on sales calls
  • Also generates an internal brief with deeper analysis for your own prep
  • Job posting analysis surfaces signals about company priorities and gaps
  • Works as a visual anchor during calls to keep conversations focused