A couple years before Digital River started to lose the confidence of investors in 2007, another company had entered the space: FastSpring, launched by four proven software entrepreneurs. Digital River and FastSpring are two actors among many in the industry focused on selling more online. Comparing the two sheds light on a hugely important but immature sector.

When you buy online, those last few moments of a sale are often turned over to some third party who steps in as the merchant-of-record, which may include managing fraud, taxes, chargebacks and probably building those last few web pages or the in-app store. That work represents a market estimated to be somewhere around $1.2 trillion annually. It’s an industry that arose from downloadable software but has moved into subscription services, media, online games and physical products. It’s complex and getting more so as companies take their wares global.

In 2013, Digital River processed $30 billion in sales and FastSpring $130 million. Digital River has been the troubled global leader in this space for twenty years, a brand that companies like Lenovo and Microsoft trust to protect them from fraud and penetrate new markets. It’s CEO, David Dobson said that you can look forward to more big names coming into Digital River’s fold over the coming months. The companies have been won over by the $100 million in investment that Dobson prioritized as he came on, upgrading the platform’s infrastructure, improving its flexibility, countering downtime and backing everything up.

Dobson said, “This is a story of transformation. An incredibly powerful company from a software standpoint, as a platform, starting to move into new markets. I’m not ready to declare victory. We have to prove ourselves to the market.”

Digital River is probably not as big as it should be and it is also not as valuable as it has been. Dobson marks the first dark moment in the company’s history as the 2009 departure of Symantec, which had accounted for 30% of Digital River’s revenue. It left, Dobson said, because Digital River never cut it a break on price as it grew.

But, was Symantec really the key loss or the just the most notable one in a larger trend? When Symantec left the company, Digital River’s stock took a sharp dive, yet it had already been falling, decisively, since its high of 59.61 in 2007. The overall trend would continue down, to the point that, as of late 2011, it would drop below 20 once more and stay there.

Meanwhile, FastSpring, as Jason Foodman, one of the co-founders explained, pitched its business on customer service and updated technology. The company built each clients’ store to be fully integrated with the look and feel of the rest of the client’s site, and then it would be there with a real person whenever questions arose (either from the client or one of the client’s buyers). Second, he said, a new era had arisen in object oriented software that Digital River hadn’t caught up to yet. FastSpring’s platform yielded a faster setup, gave its clients more flexibility around making packages of products, mixing them and discounting in sophisticated ways.

FastSpring is still tiny compared to Digital River, yet it’s easy to make the argument that Digital River’s recent investments are following where companies like FastSpring have led. Which may be why Pylon Capital, a search company, acquired FastSpring for $12.4 million. FastSpring grew gross sales 37% in 2013, and its new CEO, Tom Tzakis, expects that same growth to continue.

There is a lot of overlap in the basic offerings of these businesses vying for that trillion dollar market, but Tzakis articulated something about what’s happening, saying “Companies like us are able to focus on certain attributes of our business that we find the most appealing.”

In other words, it’s not so much that the difference between what the companies actually do so much as what each emphasizes. For FastSpring, that leads with customer service. Foodman said, “From the get-go we took a very different approach to customer service, really placing a key emphasis on that in an industry where it really wasn’t.”

With that focus, its team has the space to do the handholding startups may need. If one of those new companies ends up becoming the next Adobe, it could move a company like FastSpring a lot nearer becoming the next Digital River.

Another company in the space, BlueSnap, which was acquired as Plimus in 2011 by private equity firm Great Hill Partners for $115 million, emphasizes its global acumen (also, in best YouTube videos). Ralph Dangelmaier, CEO, pointed to mobile payments’ 60-90% abandonment rate, explaining, “Number one: it’s not easy, it’s not uber-lite … the second problem is, it’s not local.” So, BlueSnap will use a buyer’s IP address to lead with the payment method (and in the language) that people in a given country are most likely to use.

Which isn’t to say other companies don’t do that too. Some do, or they will soon. In this business, all players seem to think every facet of the work is the table stakes.

One of the few true differentiators between competitors seems to be the sheer number of buyers in Digital River’s portfolio. At scale, buyer volume becomes powerful. For example, if the same buyer uses Digital River’s services in Microsoft, Adobe and a few smaller companies’ stores, this allows it to profile customers. They can use this data to offer marketing services to their clients, upselling buyers based on products that their models tell them similar clients want.

The market Digital River seems to emphasize going forward are those enterprise clients for whom this kind of service is key. Though they have small clients, too, the bulk of their business comes from companies moving $10 million to $1 billion in annual sales. That said, FastSpring is also winning over big companies, including Toshiba and Random House.

Yet for the investment community and developers looking to do work with meaning, will the future of this industry be defined by the company serving the top brands in mature industries, or will it be defined by the company empowering startups that most people don’t even understand yet, the kind that create whole new markets?