Because Amazing Software Isn’t What Makes Your Conversion Succeed

Most system conversions fail—not due to choosing the wrong product, but because agencies underinvest in the people, process, and planning required for success. 

I help leaders achieve successful conversions by thoughtfully involving their staff, preparing their data, and managing change so they not only survive "go-live" day but also thrive in the new system.

Which of these describes your agency?

Agencies heading into a major system change tend to fit in 1 of these 3 categories:

  • Legacy Users

    These agencies know they're running on outdated systems but the idea of change seems overwhelming and they don't know where to start. They are so far behind, it feels impossible to catch up. Meanwhile, their profits are declining due to inefficient processes.

  • System Hoppers

    Not afraid of change, these agencies switch systems every few years, resulting in significant costs and frustrated or disengaged teams. They are always on the lookout, thinking the "best" system is the one they haven't tried yet!

  • Burned Migrators

    Memories of conversions-gone-bad leave deep scars. These agencies are afraid to change systems they've outgrown because they've been traumatized by failed migrations in the past. They want change but lack the confidence that they can do it better this time.

Why System Conversions Fail

Migrations don't usually fail because of the technology. They fail because of the transition. Here are 6 common characteristics of agencies who experience migrations that go poorly.

  • Not getting clarity on the actual problems they’re trying to solve with the new system

  • Trying to force the new system to mimic the old system

  • Bringing over dirty data thinking they'll clean it up later

  • Making decisions without end-user insight and buy-in

  • Skimping on training and rushing rollouts

  • Not planning for stabilization and optimization after go-live

The cost of poorly managed conversions

The hidden costs add up fast—and far exceed the price of doing it right.

A poorly managed system conversion is one of the most expensive mistakes an agency can make. The hidden costs pile up fast: frustrated staff, broken workflows, service interruptions, incorrect data, angry clients, plummeting morale, and months of lost productivity. Many agencies lose far more in rework, overtime, and turnover than they ever would have spent on proper planning and expert guidance. Investing in structured support isn’t an expense—it’s protection against a nightmare you’ll be paying for long after go-live.

How to lead a successful system conversion

  • Sell the Change Internally

    I help leaders communicate the true cost of not converting, connect the new system to user-submitted pain points, and create psychological safety for being a beginner again. System conversions are 50% technology, 50% emotions. I help you lead both.

  • Prepare for Go-Live Day

    I provide training on how to structure Blackout Week journals, reenter work efficiently on Go-Live Day, maintain client service without revealing internal chaos, and create a calm, fun environment that supports learning and resets team energy.

  • Build the Post-Conversion Roadmap

    Going live on the new system isn't the finish line... it's the start! I walk agencies through the 6 critical phases that happen after launching the new system. This is what ensures long-term success—not just short-term survival.

DIY Option: Take The Online Course

$1,295 (bulk discount available)

The Confident Conversion: A complete self-paced guide for agencies preparing for system change. Bonus materials include: Selection committee guide, end-user survey templates, change communication scripts, data cleanup checklists, Blackout Week and Go-Live Day instructions, 12-month optimization roadmap, automation identification worksheets, and core values alignment exercises. Discounts available for agency groups purchasing in bulk.

Fun with Friends: Join the Mastermind

$2,480 per member for 12 months

Package includes a guided 12-month cohort + my full online course, The Confident Conversion. Perfect for agency clusters or networks changing systems together. Includes: Full access for 12 months to the online course, monthly live webinars with Q&A, peer support and sharing of best practices, personalized coaching, templates, and guided prep.

Host a Private Party: Request a Custom Webinar

$8,499 for up to 50 attendees

90 minutes of high-impact training for leadership teams. Topics covered include the top reasons conversions fail, how to prepare your staff psychologically & operationally, the 5-phase conversion roadmap, how to lead a successful blackout period & go-live day, planning for ongoing success post-launch, and time for Q&A. This package also includes a 30-minute planning session before the event to understand your group's unique needs and opportunities and coordinate the date and time of the webinar.

Ready to roll?

Contact me to discuss which option will be best for you!

Email Jessica

About Your Coach

Agency Operations Specialist Jessica Yarbrough, CIC, CISR, AFIS, IA-MBA

I don’t just teach on operational excellence — I’ve built it in the real world. My career grew from CSR to COO in under a decade, and today, I’m the first female owner of an agency founded in 1915. Under my leadership, our firm has been named a Best Employer in North Carolina every year since 2023 and earned the prestigious Best Practices Agency designation from Reagan Consulting in 2025. Now, I help other agency leaders build the kind of business where technology amplifies people, processes strengthen culture, and growth stops being accidental — and becomes inevitable.