Ads that appear next to search results are one of the most valuable forms of online advertising, because they are matched with users’ searches for things they want to buy. You see an ad next to a result for what you’re looking for, then you click on the ad instead of the result, and make a purchase. But organizing large search ad campaigns gets complicated, because these ads are matched up with a user’s search results based on keywords submitted by competing advertisers.

That’s where Clickable comes in — and one reason why it has just raised a second round of $14.5 million from some marquee investors. The New York-based company provides web-based project management software that helps small to medium sized businesses organize their search-ad campaigns, replacing Excel spreadsheets that many of these advertisers currently use. It’s dashboard-style interface lets users plan search ads across search engines, including Google, Yahoo and Microsoft.

Clickable launched publicly in February — although we’ve been tracking it for some time — and it isn’t saying much about how it’s doing beyond that it’s gaining up to 200 new clients per month. But the funding is certainly a positive indicator for whatever is happening behind the scenes. It has raised a total of $22.5 million so far. The latest round was led by The Founders Fund, with existing investors Union Square Ventures and FirstMark Capital participating. Earlier individual investors also joined in, including Jon Miller, a former AOL chief executive, current Yahoo board member and Velocity Interactive Group partner, and Peter Thiel, co-founder of PayPal and Managing Partner at The Founders Fund.

Clickable is trying to be a comprehensive site for newbie search advertiser needs. It has built out its home site as a sort of learning community for beginner search-ad buyers — a group that otherwise experiences a lot of “churn,” with many people trying these ads and leaving, chief executive David Kidder tells me. The site includes user guides, case studies and other educational features. This community, in turn, has helped the site on search engine rankings, leading to more first-time customers who find the company through searches.

Among other features, the software includes a recommendation tool that lets advertiser see how well their chosen ad keywords are performing, or if a competitor’s keywords are doing a better job of reaching desired users. This feature recommends potential keywords to help an advertiser better target their ads and beat out competitors — faster and easier than crunching data about keyword performance within spreadsheets.

Larger companies providing search-ad optimizing services include SearchForce, Marin Software, Efficient Frontier and Omniture. These companies charge significantly more for complex optimization software designed for larger advertisers, while Clickable is aiming for advertisers who spend between $1,000 and $50,000 per month, Kidder says.

Closer competitors to Clickable include ReachLocal, Yodle and other companies aiming for small businesses that want to bring in more business through search results. These companies, like Clickable, also use on-the-ground sales teams and search ads to drum up business. Also of note to Silicon Valley advertising technology folks: Clickable made the point to me that its New York location has helped it develop relationships with media-world clients including advertising agencies — early users that have in turn helped the company refine its product. Finally, perhaps Clickable’s most direct competitor is Enquisite, which offers its own search ad keyword recommendation web software.

While Clickable is initially focused on search ads, it also plans to move into offering optimization services for clients running video ads, and other forms of online advertising.

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