Tomorrow, Barack Obama is expected to name the nation's first chief technology officer—the person who will rebuild the White House out of zeros and ones.

The appointment comes on the heels the most technologically savvy campaign in history—during which Obama amassed more than 10 million email addresses, sent an estimated 2.9 million SMS text messages, and mustered an online army of more than a million supporters. His CTO is expected to employ a similar tech savvy to make the federal government more accessible to citizens.

Obama’s got 130,000 followers on Twitter who are left stranded. They should be communicating and engaging more than ever now that the really hard work has begun.

The transition team's Web site already offers a few hints of the changes to come, allowing visitors to leave questions for his advisers to answer online. (The leading question from the first round: "Will you consider legalizing marijuana?")

But dragging the executive branch into the Web world will be a colossal task. The Daily Beast consulted with a few of the legends behind today's most influential Web firms, and they dispensed some free advice:

● Craig Newmark, founder of Craigslist, has been dubbed Obama's "official technology surrogate," but he downplays his role: "I'm no big deal, have no particular influence with the Obama team, but they did reach out to me during the campaign as a member of the tech community."

Regardless, he's discussed several of the president-elect's technology proposals with the Obama team, including one that hits especially close to home: Obama's pledge to apply technology to civic participation by launching "a Craigslist for service"—a Web site where users can learn about public service opportunities.

"Users will be able to rate their volunteer experiences, and those requiring service will be able to specify skill sets and time commitments required," according to the campaign's national service plan. "Users will also be able to track their hours of service if they choose and perhaps compete for awards from local chambers of commerce or foundations."

● Reddit co-founder Aaron Swartz is tired of tussling with federal agencies over Freedom of Information Act requests, and he wants Obama's CTO to put public government data online for all to see. "We've had to do some crazy stuff to get data out of the government," says Swartz, who also runs Watchdog.net, a hub for political data and activism. "The average programmer, the first time they have to call up a government agency, [they find] it's not worth it.”

Swartz goes even further, proposing a national project to scan the millions of paper documents that live in the National Archives, Library of Congress, and other repositories—a massive program that would dwarf Google's effort to scan library books. "Imagine if we had a public process to take this and put it online—not just for one company, Google, but for the public at large," he says.

Swartz has also heard rumblings inside the Obama camp of an initiative that would harness the Internet to improve science education in America's high schools. Citizens would sign up online to visit science labs at public schools in their communities, and would then send the president’s advisers their observations on the labs' quality. In past administrations, the government would have commissioned an expensive study from RAND Corporation, Swartz notes. "Instead, you can have the American people do it, and see what their schools are like and build a community connection, and save money while doing it."

● Jimmy Wales, co-founder of Wikipedia, suggests the White House try launching similar "wikis" to connect citizens. Indeed, the president-elect's advisers have cited the online encyclopedia as a way in which Americans could meet online to mull over legislation and policy issues. But Wales cautions that the nation’s CTO should not lose sight of the goal. "Don't just throw up a wiki and hope that something miraculous will happen," he wrote in an email. "A successful wiki requires a clear vision, a clear and achievable goal. I think there are great possibilities for the use of wikis to help citizens help each other. I recommend to try and fail, try and fail, try and fail, but to never give up on the objective of the political process becoming more rational and less prone to hidden pressure group agendas."

● Fred Wilson, managing partner at Silicon Alley VC firm Union Square Ventures, says the Obama White House should keep using Twitter, Facebook, and the other social networking tools that the candidate used on the campaign trail. "Social media is not just a tool to win an election. It's an even better tool to govern," Wilson, an investor in Twitter, wrote in an email.

"For example, as of this moment, the most recent twitter post from his account was on election day... He's got 130,000 followers on Twitter who are left stranded. His transition team could be posting once or twice a day updates. It literally takes a second to do and they did it regularly during the campaign. It's not a good thing to change your approach to communicating with your audience once you've achieved your near term goal. They should be communicating and engaging more than ever now that the really hard work has begun."

● David Siminoff, a general partner at venture capital firm Venrock, envisions a blogging president setting up shop in the Oval Office on January 20. Siminoff—who has invested in social media startups such as BlogHer and SlideShare—sees Obama following in the footsteps of Lincoln, who "was intimately connected with his constituency... I think Obama is coming into that era in an odd way in that technology is allowing him to become a more intimate president," he says.

Siminoff recommends the 44th president to begin blogging regularly, perhaps assisted by a rotating cadre of college students who could follow him around and report the news of the executive branch to the public in real time. "I think you've got to make the content compelling enough," Siminoff says. "I think it's about speaking in a voice that people want to hear."

Nicholas Ciarelli is an assistant product manager at The Daily Beast.