Case Study: How Diann Upgraded Her Email Marketing by Moving from Kajabi to Kit

Before migrating to ConvertKit (now Kit), Diann Wingert, a business coach and host of the podcast, ADHDish, was using Kajabi for her email marketing. It was kind of working for her business, but something about the pricey all-in-one platform was missing the mark.

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Her list was growing and she was consistently sending weekly newsletters, but engagement was low and replies were rare.

The challenge: A stagnant email marketing strategy and a platform that couldn’t keep up

While her open rates looked good on paper, she sensed that something was missing.

“I felt like I was just going through the motions.”

Worse, she was paying for an expensive all-in-one platform that didn’t give her the flexibility she needed to actually grow.

Could Diann have simply integrated Kajabi with Kit? Absolutely – I’ve worked with several clients to do this.

But since Diann had decided to move her website to Squarespace, she saw the opportunity to rethink her email marketing completely at the same time. She had already chosen Kit, but didn’t want to risk a messy DIY migration, especially with a VA who was still new to the platform.

The solution: A strategic, guided Kit migration built for business growth

Rather than a full-service migration, Diann chose my Audit & Plan package – a hands-on, done-with-you consulting offer that gave her team a clear roadmap for migrating from Kajabi to Kit.

Here’s what we focused on:

Comprehensive System Audit — We reviewed everything inside her Kajabi setup, including opt-ins, automated email emails, segmentation strategy, tagging structure, and automations.

Strategic Simplification — Diann had built up a lot of great content over time – which also meant a lot of moving pieces. We pared down her system to the essentials that actually supported her coaching business, reducing overwhelm for both her and her audience (many of whom live with ADHD).

Step-by-Step Migration Plan — I created a detailed roadmap her assistant could follow confidently, ensuring nothing was lost or duplicated in the transition.

Training and Voxer Support — Diann had real-time access to me during the migration to troubleshoot questions as they came up, keeping the process smooth and stress-free.

This wasn’t just about moving from one platform to another.

It was about building a system that matched Diann’s mission: helping entrepreneurs turn their ADHD brains into business assets by uncomplicating how they show up and connect with their audience.

The immediate results: A smooth migration and and a clearer, stronger email strategy

The migration from Kajabi to Kit went off without a hitch.

But even more importantly, Diann walked away with an email system that finally matched her business goals.

And Diann’s new setup wasn’t just functional – it was purposeful. Every form, tag, automation, and email – heck, even the decision to use a double versus single opt-in – was intentionally designed to support her work as a business coach and podcast host focused on ADHD entrepreneurs.

Instead of feeling tangled up in tech complexity – a common trap for business owners managing ADHD brains – Diann’s email marketing now felt streamlined, supportive, and energizing.

“Working with Bev was a dream. She is both low-key and very professional. Her process is well thought out and comprehensive. I loved her ‘done-with-you’ consulting package, which allowed both my assistant and myself to get up to speed in a reasonable period of time. Having access to Bev via Voxer during the migration period was an added plus. Highly recommend.”

The long-term Impactevolving beyond the basics to deliver real value

More than a year later, Diann’s approach to email marketing continues to evolve.

“My first decision to up my email game was switching to Kit and hiring you. But now, I realize that just sending weekly emails isn’t enough. They need to be valuable. I don’t want my marketing channels to compete with each other—I want them to lift each other up.”

Rather than simply recapping podcast episodes in her weekly newsletters, she’s:

✔️ Testing A/B subject lines to optimize open rates

✔️ Linking to external resources to provide broader value

✔️ Creating actionable strategy sheets that help her subscribers put ideas into practice

She’s even planning to use Kit’s Liquid logic to create more personalized subscriber journeys — helping her audience stay focused and supported without unnecessary noise.

Why Kit was the right choice for an ADHD-focused business

For Diann, moving to Kit wasn’t just a technical upgrade, it was a strategic one.

  • All-in-one platforms may sell convenience, but specialized tools provide deeper functionality and better long-term results.
  • Kajabi’s email tools felt clunky and like an afterthought – an add-on rather than a core feature.
  • Kit offered the segmentation, automation, and flexibility she needed to build a system that truly served her audience and honored their attention spans.

“If I’m going to use email marketing, I want to do it well. That means moving to a platform that has features that will actually allow me to grow and refine my strategy.”

Is your email marketing system making you work harder than you need to?

If your email marketing feels complicated, overwhelming, or disconnected from the way you actually want to serve your clients, you’re definitely not alone.

And you don’t have to figure it out on your own.

Whether you’re looking for a full-service setup or a strategic migration roadmap like Diann, I can help you create a system that’s clear, streamlined, and built for the business you’re growing into instead of the clutter you’re stuck managing now.

Book a zero-pressure call and let’s build an email marketing system that actually feels like a business asset.

Now booking Email Automation VIP Days for May 2021