Repositioning Your Business for the AI Era

Free Guide

You Spent 5 Years Positioning Your SaaS. Do You Need to Start Over?

The practical framework from April Dunford, Bob Moesta, and battle-tested founders on repositioning for AI, without throwing away everything you built.

  • Figure out if your core value actually changes (or if you just need better messaging)
  • Use the “strategy fork” test to know when AI requires a full pivot
  • Position AI as augmentation, not replacement—and make customers want it
  • Follow the 30-day action plan to test positioning before betting the company
  • Avoid the “sevens” that dilute your positioning and confuse customers
Repositioning Your Business for the AI Era Guide

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Your competitors are slapping “AI-powered” on everything… Should you panic?

Most founders are making expensive mistakes right now. They’re either rebuilding everything with AI buzzwords, or ignoring AI completely and hoping it goes away.

You Don’t Know If You Need New Positioning

Does AI change your core value? Or do you just need better messaging? Without a framework, you’re guessing, and guessing wrong is expensive.

You’re Afraid of Scaring Customers

Existing customers panic when you talk about AI transformation. Prospects get lost in jargon. Nobody wants to hear your 10-year vision.

You’re Building “Sevens” Instead of “Tens”

Mediocre AI features that seem safe are diluting your positioning, confusing customers, and letting competitors focus while you spread thin.


Inside the Guide

What you’ll learn

  • 01
    Does Your Core Value Actually Change?

    Use April Dunford’s framework to figure out if you need repositioning or just better messaging. Includes the “strategy fork” test.

  • 02
    Evolving Messaging Without Scaring People

    Bob Moesta’s “half-step” approach: how to introduce AI without triggering fear or confusion.

  • 03
    Position AI as Augmentation, Not Replacement

    Why “electric bike for the mind” positioning wins — and how to frame AI so customers want it.

  • 04
    Test Your Positioning Before Betting the Company

    The exact questions to ask customers, how to run positioning tests, and what signals tell you it’s working.

  • 05
    Your 30-Day Action Plan

    Week-by-week roadmap from customer interviews to market testing to rolling out new positioning.


Learn From the Experts Who’ve Done This

This guide distills insights from BoS Conference speakers who’ve repositioned real companies through major market shifts.

April Dunford April Dunford Positioning Expert
Bob Moesta Bob Moesta Jobs-to-Be-Done Co-Creator
Guy Nirpaz Guy Nirpaz Founder, Totango
Matt Lerner Matt Lerner Founder, SYSTM

“Positioning describes how our product is the best in the world at providing something that a well-defined set of customers cares a lot about. Notice I didn’t say ‘positioning describes how we use AI.'”

— April Dunford, Obviously Awesome


Don’t Let AI Ruin Years of Brand Equity.

Get the framework that helps you figure out what to do, without guessing, without panic, and without throwing away everything you’ve built. Download now.