Fail Often & Fast: Taking the Leap to Upgrade Your Technology.

• Author: Gilmore, Trevor
• Position: Tech Talk

Coming from a technology forward background, I was in a bit of shock in 2015 when I joined my firm as its first official CFO in its 40-year history. Founded in 1974, the year that ERISA was signed into law, we are one of the original employee stock ownership plan advisory firms in the country.

On my first day, I noticed colleagues had Lotus Notes installed on their computers. Excel workbooks were hardcoded, rather than formula based. Typewriters were commonplace on old steel desks. There were no databases to speak of; file cabinets consumed much of the office. I worried that an earthquake would literally cause paper to trap people! I had my work cut out for me. I had to be the finance leader and usher the firm into the modern era.

"Fail often and fast" is a familiar philosophy in the business world especially the tech sector. I've embraced this mentality since becoming an entrepreneur at 22. Once I became a CPA years later, I used this approach to find a tech solution for a real estate client who had more than 100 QuickBooks files to track their investment funds and partnerships. As we looked for accounting solutions, I told my boss that we were "failing fast," and she was shocked until I explained what I meant: You can only succeed if you try. And we succeeded.

As finance leaders, we're often the ones to drive real change for our clients and our organizations. And depending on leadership, that might be challenging. That is where the value proposition makes or breaks a change.

Rather than rush into immediate recommendations, I spent my first year observing how everything works and asking lots of questions. I took a lot of notes, and devised my first five-year technology plan.

Toward the end of that first year, we were about to go live with our new online employee stock administration program (an SAAS-like offering) and my questioning led to the realization that we needed outside engineers to review the source code and hackers to attempt to get into the system from the outside before going live. That way we could fix any issues before someone exploits our vulnerability. From my view, this was a critical part of software deployment.

My technology goal for the second year was, you guessed it, the cloud. We had a room that hummed with our servers for email, files and software--the heat generated from them required a backup A/C unit that was always on. Server updates and an occasional spotty internet connection would cause our email and file...