If you’re still sweating midnight tonight as the deadline for filing your 2007 tax forms, this story may come a bit late. But tax preparer H&R Block has over the last two years amassed an impressive array of social media-based marketing, all designed to become top of mind with tortured souls wrestling with their 1040s.

Block’s social initiatives are designed to reinforce two brand messages, according to Paula Drum, the company’s vice president of marketing for digital tax solutions: to reinforce the company’s overall expertise, and to announce its specific Web-based competence.

“We have a great, well-known brand, with 99% brand awareness,” says Drum. “But if you’re coming at it from the digital angle, it’s now well known as a multi-channel brand. We’re better known as the brick-and-mortar shop on the corner. We wanted to increase the awareness that Block has many ways to get your taxes done, not simply by going into one of our offices. For example, you can also drop your taxes off online. We also want to reinforce that we’ve been doing taxes since 1955, and we are the experts at this.”

Arriving at Block after stints doing e-commerce and interactive marketing in the travel and hospitality industry, Drum encountered a fairly standard Web presence. The company had a corporate site, www.HRBlock.com, where visitors could order tax software either for download or through the mail, could send in tax questions to have them answered by professional accountants for a fee, and could locate their nearest H&R Block outlet.

“But there was nothing that created awareness that we had these online services available,” she says. “How could we reinforce our brand positioning online with all the new customers, especially the Gen Ys who are growing up in this medium and choosing to connect with people in different ways? How do we make our brand relevant to them, versus just thinking that we’re the way their dads did taxes?”

Drum started building the company’s online profile by launching a YouTube contest for user-generated content—specifically, songs from customers happy with their “Super Sweet Refunds”.

“It was really interesting, because I was talking about using this new medium of YouTube,” she says. “Meanwhile, even our brand agents were saying they weren’t sure it was a good idea, that it might not be ‘brand right.’ They were very used to dealing with us as a very conservative financial services company. We don’t even advertise on ‘Grey’s Anatomy’. So this was all very new.”

It was also very successful. The “Refund” contest clips got some 4 million views in all on YouTube. They also inspired some notable imitation from digital tax market leader TurboTax, which produced its own “TaxRap” video featuring Vanilla Ice.

That initial success gave Drum’s team the credibility to go ahead with another equally risky test project: launching a presence for Block in the virtual world Second Life. Specifically, Block was preparing a beta launch of a new Flash-based tax-prep product that let the company’s professionals collaborate with users who essentially wanted to prepare their own returns. Block wanted to roll the service out in a limited way, and Drum suggested building an island in Second Life would be one viable strategy.

So in 2007 the company debuted “H&R” Block Island, a Second Life destination where the company’s tax pros could offer free advice, showcase its products and host tax-related events. And if that last phrase sounds dull, note that Drum and her team have livened up the fiscal drudgery with a healthy dose of music, dancing and other virtual interaction among the visiting avatars.

Starting in January, the company began holding a “Tax Advisor Hour” on Block Island every Tuesday and Thursday evening, and added a live (virtual) DJ to the mix in February. Several of Drum’s staffers have also run tax trivia contests on the island.

The Second Life initiative, innovative though it may be for Block’s industry sector, is still just a small portion of the company’s online marketing budget. Among other things, that relatively small expense has put off internal requirements that “H&R” Block Island meet any specific ROI goals.

“I’ve been very upfront in saying that, especially as we move into year two and think about expanding this, we should be looking at how we’re changing perceptions of our brand,” Drum says. “So there may not be an immediate ROI on this. What we’re trying to do with our emerging media is to move brand measures, so we need to be looking at broader measurements than ROI.”

In fact, applying tracking metrics to Block Island during its first year would have cost more than actually building the island, so Block didn’t apply any yardstick to last year’s effort. This year, Drum says, they’re starting to measure activity in the virtual world.

This year Block also complemented its corporate Web site with a social media site in www.digits.hrblock.com. The Web site offers serious tax advice, but it’s leavened with a number of features that recognize that for most of us innumerates, tax prep ranks with dental surgery as one of life’s pleasures. So the Digits site looks at life beyond withholding with features that let visitors share opinions on politics, art and the workplace as well as taxes. It also offers lots of content that puts an amusing or engaging spin on the subject of finances. For example, a Web game called “The Deductor” tests players’ skill at picking up deductions while dodging irksome IRS agents. And visitors can post a widget to their blog pages that offers updated schedules for Block Island events and lists the latest posts to Digits’ conversation forums.

Truman Green, Block’s fictional Web spokesman

The site also offers short video clips of Truman Greene, a fictional spokesman for H&R Block whose over-the-top enthusiasm for tax prep borders on the absurd. Greene is Block’s follow-up video effort to the “Sweet Refund” contest, but with a twist.

“We could have repeated last year’s YouTube video contest and we considered a number of concepts,” Drum says. “But I’d equate most of them to the brands that build a microsite and then try to get people to go to that site. The thought behind Truman and some of the other activities around the videos was to create something we can take to where the traffic is rather than driving people to us. Truman lives in many places: He’s on Digits, but he’s also on YouTube and MySpace and syndicated in different areas. That gives us an asset we can place in multiple channels.

“The YouTube contest was successful and we learned a lot, but we didn’t even tell our own customers about it and didn’t try to engage any other communities. The reality is that people belong to many different communities, and being able to get our own customers engaged with some of these things is great for customer retention as well as acquisition. Some people who love Truman have put his videos on their own sites.”

In what may be its most interesting foray yet into emerging media—and with possibly the greatest potential impact—H&R Block has also launched a marketing initiative in Twitter, the social networking service that lets users fire out short 140-character updates or messages (called “tweets”) to the Twitter Web site, where they can be viewed by the general public.

H&R Block began getting involved in Twitter late last year and initially saw it as just another platform for propagating brand messages about the company. “But what we learned very quickly is that the value of Twitter is really as a listening tool,” Drum says. “Yes, we’ve pushed out some brand messages, but primarily we’ve been listening and helping people who’ve had a bad customer experience, or who are just asking for tax advice or even looking for jobs. Those interactions are much deeper than simply pushing a marketing message. They’re about really being part of the Twitter community.”

The Twitter campaign paid off big last month when a Block employee monitoring tweets realized that Robert Scoble, ex-Microsoft guru and prominent emerging media blogger, posted a note that he was in an H&R Block office getting his taxes done. A message was sent off wishing him well and offering further help if needed. Scoble went on to evangelize in interviews about how that simple interaction, taking place while he was still the Block office, persuaded him that Block was a responsive and involved company and an example of what other brands will need to do to stay on top of social media.