Lessons Learned From a Career of Replatforming

Well, here we go! This is the first in a series of posts on “Replatforming.” I’ve never written a blog series before. I think I’ve written three blog posts in total! My first was about 8 years ago when I worked for Vitacost/Kroger. That’s it because I’ve spent fifteen-plus years helping retailers with replatforming efforts.

Replatforming brings up all kinds of connotations. Dread, Excitement, Fear, Hope, for sure.

How you feel about replatforming depends on why you are doing it, you as a person, your role, company culture, etc. When thinking of commerce platforms, one thing is for certain: Some just flat out fail. Obviously, that’s a disaster on several fronts: cost and time, for sure, but opportunity cost and perhaps an erosion of trust in your own organization.

My replatforming experiences are here to help you

What I’ve seen over the years is that most replatforming projects end up costing more money and time than was initially estimated. And, even for those that were successful, they either fall short of the expected return on investment or the ROI is too confusing to even track.

That said, replatforming can be really fun. It should be fun because you get new platforms, new partners, and probably even new hires. With all of the retail expectations innovation can bring, it can be a thrill. All the time and effort to replace a legacy ecosystem—the blood, sweat and sometimes literally tears. And, all the money out the door betting on it coming back in some magnitude—why NOT write about it?

And who the heck am I to talk about it? Well, that’s a story.

Career replatforming, from the military to tech to commerce

I have had three dramatic career changes in my life. From the ages of 18 to 63, that’s not a lot—but they were dramatic! Here’s a quick view of my background:

The first stage was when I joined the U.S. Army in 1980 under then-President Jimmy Carter (quick, name his VP?!). I loved my military career. It included a few years as an air traffic controller, a shift to the U.S. Coast Guard Academy, and a mini-career at sea and overseas. I was a ship’s captain in Gloucester, MA, an undercover Naval Intelligence operator in Panama, and did a few tours in between. U.S. Army and Coast Guard Veteran: career #1!

The second stage was when I got out! In 1997, nearly complete with my Master of Telecommunications & Computing Management from what is now NYU (and what was then Brooklyn Polytechnic) I was offered the role of Chief Information Officer at Production Resource Group in New York. Sub $50MM in revenue and I was its first tech leader as we blasted on a more than 10X growth rocket ship. We put in ERPs from scratch (still there), and a homegrown inventory and asset management system (still there). Hiring people way smarter than I was, with them often making more money than I did. I may have been the only CIO with a Sr. Director title, but I learned. From the ground up, everything was a blank sheet of paper.

From there it was all commercial businesses. CIO and head of India Operations for ATG, a super fun creative agency pre-press shop and even offered large scale printing services out of Chicago that became “Shawk!” Then it was Rosetta Stone as CIO and SVP of Customer Success. That’s the language learning company, and I was there during its hyper growth and IPO. From there CIO, CTO, and de facto COO at Vitacost, a healthy living ecommerce company bought by Kroger half-way through my watch. Then Chief Digital Officer at FTD, the flower company—plus several other brands—managing the P&L and all CIO, CTO, COO, and CMO functions. And next to last, Chicos FAS, a $2B+ three-brand retailer, again as a CDO managing tech, digital strategy, the supply chain, and customer service.

Nearly 27 years as a C-level digital leader and seller of goods and services—career #2!

Now, I am in my third and most recent career change working for tech company: A well-funded, mighty, nimble ecommerce and order management platform provider: fabric, Inc.

It feels surprisingly similar to my first CIO role building tomorrow’s ecommerce platform from a blank sheet of paper. I got to know fabric well before I joined, having implemented this wonderful technology into Chicos FAS before I left. I worked closely with fabric’s commerce platform and order management system engineers, product managers, and the whole team. In this move, I went from a hard-core operator and technologist managing tens of millions of dollars and sometimes up to 3,000 employees to being an individual contributor bringing hands-on retail platform expertise to fabric and its customers. I am here to serve product marketing and sales, getting the word out about our amazing solutions (did someone say blog?!), and demystifying replatforms.

While just being my genuine self—really that’s how this was pitched to me. I love being myself so this all works—career #3, here we go!

An experienced approach to order management for commerce

How am I qualified for this role and to author this blog series? Well during my middle career—as a C-level selling goods and services—I have built and I have bought many, many platforms. I estimate I have implemented nearly 70 platforms (yes, I tried to count). From Martech to Commerce, Supply Chain, Merchandising, Customer Service, Reporting, Data Management, and, of course, back-office and enterprise systems. I’ve analyzed 300-400 to get to 70, read more industry reports than I could ever hope to count, and relied on dozens and dozens of peers for their perspectives.

In addition, I have upgraded over 100 platforms of varying complexity. Think of all the data changes I’ve been involved with, management reporting I’ve had to do, and order management and commerce platform vendors and Systems Integrators I’ve had the pleasure of working with. For the latter, I just hired brilliant people who were smarter than I was. Don’t get me wrong: I was also leading the transformation of existing “smarter than me” associates that wanted (usually) to be part of change (don’t underestimate my change management experience!).

Across all of these projects and professions, I can only think of one failure and one successful disappointment. That ain’t too bad. Maybe others were less than perfect, for sure. With all of them, regardless of outcome, I have learned a lot (e.g. give up on real failures fast) and I am sure I can use that knowledge to help our customers do better. I can help retailers do better!

Join my replatforming journey for retailers

Stay curious and humble, learn from mistakes, and subsequent programs automatically become less risky.

Now I get to write about it at this cool tech company called fabric as we build the next-generation commerce platform. Join me on this journey to learn how they fit into an even bigger picture of transformative change. Hopefully, you trust my passion, and my credentials—I must know something, right?

OK, in my next installment, I’ll get straight to the point! Check back here next Tuesday where I’ll start where it all starts: Amid all the time, money and risk, Why Replatform?

Topics: Commerce