Kevin Dwyer’s career in technology spans two decades and includes six successful startups. Red Canary asked Kevin, now the (former) CEO of Shoplogix, to share his thoughts on the shifting landscape of technology sales.

By Scott Valentine

Red Canary: You’ve built successful sales organizations across a spectrum of value propositions (purchasing with Ariba, data management with Sybase, interactive marketing with Platinum Software and now process optimization with Shoplogix). What are the ties-that-bind?

Kevin Dwyer: At a personal level, there was no master plan, though I would volunteer two common denominators across all the companies I’ve been affiliated with.

First, if you want to have accelerated growth curves, you need a timely, working product with an extraordinarily strong value proposition.

At Sybase, we kind of changed the world by the bringing notion of client-server computing to market, which people didn’t think was a viable vehicle back then. But the product’s value proposition was apparent and it solved some real business pain, so it worked. You can superimpose that idea across all the successful software companies I’ve been involved with.

The second component is people. I look around at colleagues of mine who have been doing it since 1980 and we all have fraternities of some sort. In reality, it’s way more than two things, but if a product has value and there’s good people to make it work, you have the basis for success.

RC: What’s changed in the technology solutions sales cycle over the last 20 years?

For maybe a decade, you had customers buying mostly off of a PowerPoint presentation, only to find the promises made were never fully realized. So, it’s sort of once-bitten, twice-shy. Customers are far more cautious now about moving towards enterprise-wide deployment until the solution can be proven and validated for rate of return etc.

The flip side of that is that vendors need to bring a more mature, demonstrable product to market that works as advertised. That’s a change that’s really noticeable to me.

RC: Is there a commercialization success formula that you’ve developed over the years and keep going back to, or is it more a matter of sizing up each opportunity as it comes along?

KD: The latter, I think . . . I’m living through it again now with ShopLogix.

Every startup has a lot of variables in the marketplace. I may have a sense for what I think is going to happen, but you always need to get your hands dirty and your nose bloody to find out what the deal is. Within about 24 to 30 months, you have a feel for how you’re tracking.

Ariba was so quickly endorsed that inside of a year we knew it was a winner, but those are few and far between. There’s a lot of lessons learned in that first 30 months and a lot of mistakes made too. You have to make them and you have to learn by them, and adjust.

RC: Dot-com changed the stage that business performs on. Web 2.0 has taught us that the show needs to be interactive. Care to take a shot at predicting what the next generation of tech entrepreneurs is going to sell?

KD: You know what? I wouldn’t even try. I would never have predicted early-on in terms of Openmarket and their transaction engine, and what that meant, and I was involved with that.

And I never saw the need for procurement based requisitioning. That’s really the beauty of this business though.

It [comes] back to smart kids. I sit in on presentations with a couple of venture capitalists I work with going: ‘Holy moley, I can’t believe that. This kid is like 25 or 26, why didn’t I think about that?’

I think there’s visionary people out there – business and engineering types – and then there’s guys like me that get introduced to an idea early on.

My thing is, I see how that idea could play out, and then it’s just a matter of executing. It’s about making a revenue engine out of a good idea. Get some cash flowing, and grow a business out of it as quickly as is humanly possible.

RC: Thanks Kevin.

KD: My pleasure.