Chris Ricci is a builder by nature. He has spent the last 20 years of his career in software development and has been involved in the e-commerce game since its inception with big players like Amazon, Dell, and Sears. Today, he’s helping small businesses thrive in more ways than one. Not only is he a Startup Tech Advisory Network (STAN) Advisory Board Member, but he’s also CTO of Indigenous Software, a company providing RSB (really small businesses) and non-profits an all-in-one software solution. Chris shares his experience around the growing pains of leadership, the hipsters-hacker-hustler startup package, and the e-commerce marketplace of tomorrow.

The Talent Pool: Chris Ricci

Talentedly: What sparked your interest in software development? How did that evolve into specializing in e-commerce?

Chris Ricci: I didn’t realize this was what I wanted to do until I was almost done with an electrical engineering undergraduate degree. What I really enjoyed in work, school and life at that point was building things, and making something out of nothing. It was a part of life in electrical engineering, certainly in digital design (my specialty) but with software you can go from idea to implementation in virtually no time and with very little investment (even less today than when I started).

I came to e-Commerce by way of a fascination with disruption and the “blank whiteboard moments” that come from working on new and disruptive solutions. During the period of energy deregulation in the US (mid-1990s), I was working on utility services and billing solutions. During the first dot-com boom, I got enthusiastic about moving traditionally offline processes online (in particular digital signatures, contracts, workflow and process automation). Sarbanes Oxley was crazy-disruptive to a lot of businesses but got me into content and document management. eCommerce is really just an extension of that evolution in interests. It’s an industry desperate for a rethink, and I keep getting drawn back into it.

However, next-up is the freelance and “Really Small Business” (RSB) space. There are more than 27 million RSBs and Mary Meeker’s 2015 Internet Trends report highlighted the move to freelancing. Most freelancers are moving into self-controlled and diversified earning models that, to me, makes clear we need to prepare for changes to the shape and character of our workforce. It also means there are going to be a bunch of people (50+ million, in the US alone) needing tools to allow them to pitch themselves while staying focused on their own passions and offerings. That’s why I’m now at; we’re simplifying and consolidating the tools for content management, commerce, customer engagement and marketing.

TLY: Was there a specific moment that changed the trajectory of your career?

CR: I’m a reluctant leader. People who’ve worked for me figure this out quickly. Regardless of my scope-of-control, more than anything, I want to be building things. In the early 2000s, while consulting and hiring teams to do the development, I was forced to relinquish control of the deliverable and came to realize that in Leadership you’re still hacking and building but with different building blocks – with people and teams – instead of with software and integrations. I still struggle to let go of the technology at times but it was with this discovery, I finally came to appreciate the value and artistry of leadership.

TLY: What do you think is the most underrated skill in the workplace?

CR: Listening and humility. I worry when I encounter teams or cultures or communities of list-makers, overly-focused on building and prioritizing long backlogs, rushing through tasks without regard or contemplation of the value of it all. I love getting things done and going fast, but when I realize that I’ve been focused on the tactical for too long, it’s often because I’ve lost sight of the strategic. The engine may be running but could be pointed in the wrong direction. Listen to your customers, team members and your own data and allow yourself to be humbled and surprised by the direction it can take you.

TLY: Who do you see as your coach?

CR: I learn the most from those who’ve worked for and with me. When I’m looking for a new project or job, I look first to the team members and leaders to see what they can teach me. I can’t think of a period in my career when I didn’t feel like I was learning; what to build, how to build, how to be empathetic to my team members or the customer, how to fail, how to be at-peace, even how to relax and stop working. All of this I picked-up, bits-n-pieces, from those around me.

The Talent Pool: Chris Ricci

TLY: What is the biggest misconception of being in the software development industry?

CR: We are and need to be humbled by the lack of apparent inclusiveness and we shouldn’t tolerate the childish and vocal few that make it seem intolerant or immature. Yes, we are lacking diversity in certain areas. However, in my experience, software development is an open and inclusive culture, more empathetic than some think and extraordinarily accommodating to a variety of lifestyles, points-of-view and personalities. There’s plenty to address but for those making their living in software development, there is also much to celebrate and embrace. And, for those interested, give us a try and help us to change the shape of our workforce.

TLY: As a STAN Advisory Board member, what’s the advice you most often give startups?

CR: Ideas and business models tend to change. It’s the team’s capabilities and character that gives you the tools and energy to be successful regardless of the circumstance. I like Rei Inamoto’s; Hipster, Hacker, Hustler delineation; Hipsters bring the creative, Hackers the solution and Hustlers package and sell it all. It fills most of the gaps so I look for some element of each from the founding team and early hires. If you don’t have all those gifts onboard already, find ‘em.

TLY: Over the last 10 years, what’s been the biggest change in the e-commerce industry? How have you adapted?

CR: Moving physical to digital was e-Commerce 1.0. At that point, we were solving for customer trust. We needed complete and reliable product data, security and predictability. Get the basics right and customers comfortable spending online. Closing the loop or bringing the digital experience into the physical stores was e-Commerce 2.0 – Omni- or Multichannel – but it was bolted-on and occasionally disjointed.

In this third wave of e-commerce, we’re seeing experiences and products, and product development, that natively and comprehensively marries customer need, intent and engagement with selection, technology, the buying experience, social and customer engagement, advocacy, analytics, personalization and more. Apple, Nordstrom, Nau are killing it on the innovation front because they’re willing to build buying experiences differently. Trunk Club is reinventing personal shopping and Zappos and Amazon, well, they continue to remind us of what’s possible without the physical plant.

TLY: Quote or mantra to live by?

CR: “Courage is what it takes to stand up and speak; courage is also what it takes to sit down and listen.” -Winston Churchill

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