Whittaker: What the Implementation Conversation Usually Misses — Observations

When it comes to technology implementations, especially in the nuanced world of single family offices, failure isn’t an option. But it happens more often than you’d think—and not for the reasons you’d expect. According to Ashley Whittaker, President of Global Sales at FundCount, most failed implementations don’t stem from technical glitches. They happen because of how people make decisions, handle change, and structure their teams.

After working on over 50 single family office implementations at FundCount and spending more than 30 years in the fintech space, Ashley has seen it all. In a recent conversation with John Carroll, he laid out the four key things your tech vendor wishes you knew—before you start your implementation.

1. Re-Engineering: Don’t Rush It, Don’t Avoid It

One of the biggest reasons implementations go sideways is poor re-engineering. Family offices often start their tech journey by insisting that every report in their current system must be replicated in the new platform. That impulse can sabotage the process from day one.

Ashley explained, “We’ve seen clients come to us insisting that they have 100% of their current reports reproduced exactly… You can find that 50% plus of them may not have been used in years.”

Some firms try to re-engineer everything before they even understand what their new system can do. Others skip re-engineering altogether and just recreate legacy inefficiencies. Both approaches backfire.

Instead, go into your implementation knowing that re-engineering is essential—but only after you’ve taken the time to learn what the system is capable of. Use the implementation period as an opportunity to simplify, streamline, and rethink your reporting needs.

2. Learn the New System Yourself

It’s tempting to offload implementation to consultants or even ask the vendor to do the heavy lifting. But if you don’t take the time to learn the system yourself, you’ll miss out on most of the benefits it offers.

“Learning the new system is one of the key things that you’re going to do in an implementation,” Ashley emphasized. “To do it any other way or have the consultant or even the vendor build the system for you… that doesn’t work in a software world.”

The truth is, nobody knows your data, workflows, or reporting priorities like you do. Consultants can play a supporting role—freeing up your time so you can focus on learning the system—but they shouldn’t be steering the ship. Your organization must take ownership of the system’s configuration and usage if you want to see a real return on your investment.

Ashley shared a powerful example: “With a system like FundCount, even if you don’t automate anything, our clients have reported 100% efficiency improvements. Once they automate, that can be anything up to and over 6,500%.”

That kind of leap doesn’t come from outsourcing. It comes from diving in and understanding what the system can do.

3. Data Management: Less Is More

When it comes to historical data, many family offices try to do too much. They believe they need to backfill every data point from the past decade before they can go live. That mindset creates costly delays and derails timelines.

Ashley offered a helpful distinction: “Let’s just quickly define what historic data is—it’s data that is no longer in your balance sheet. If it’s in your balance sheet, it’s current data, no matter how old it is.”

He recommends loading only current data into the system before go-live. Historical data can be added later—once the system is operational and your team understands how it works.

Insisting on full historical data migration early can destroy your budget and your timeline. “We’ve seen clients spend hundreds of thousands of dollars literally for no good end,” Ashley said. Worse, they often end up trying to correct errors down to a level of immateriality—adding insult to injury.

Before you start your implementation, determine what data you actually need to run your operations. Prioritize that. You can always add more later once you’re confident in the platform.

4. Build the Right Team—With Authority

People—not tech—make or break implementations. That’s why assembling the right team internally is non-negotiable. You need a project manager who has both responsibility and authority. They must be empowered to make decisions, call in key players, and clear roadblocks.

Ashley compared it to FundCount’s own approach: “Our project managers have the right to call on anybody within the organization to get the job done—including the CEO.”

That’s the level of internal alignment you need. If your PM lacks authority, or if you rely on a gatekeeper model where communication gets filtered through one person, you’re setting yourself up for the software equivalent of a game of telephone.

Vendors need access to the people who understand your data and your operations. Your team should include people with the right skills for each task—not just the people who are available. Someone who has managed your QuickBooks might not be the best fit to oversee a complex data migration.

Wrapping It Up

Ashley Whittaker’s advice is clear: if you want your family office tech implementation to succeed, focus on the human elements. Don’t start re-engineering too early—or skip it altogether. Commit to learning the system instead of delegating that responsibility. Manage data strategically, not emotionally. And most importantly, build a team with the skills and authority to make it all work.

The biggest takeaway? Implementation success doesn’t hinge on your vendor’s capabilities. It hinges on your willingness to engage, learn, and lead.

Ashley put it best: “You’ve got to learn the system to understand how you’re going to deliver those efficiencies within the parameters of the requirements that you have.”

Take that to heart, and you’ll be well on your way to turning your next implementation into a success story.

Want to learn more about process optimization, tech selection, or governance best practices for family offices? Reach out to us at Jon Carroll + Family or explore our Family Office Project YouTube Channel.