Ever since creating my own Pokemon card selling & trading business in the 5th grade and implementing marketing and promotional campaigns to neighborhoods far beyond my own (promotional grab bags, weekly sales, consultations with "competitors" on their sales strategies), I have been passionate about finding ways to help others discover the products and interests I love.

Squarespace is a product unlike any other because the possibilities for what users can do within their "space" are nearly endless. Luckily, many customers are taking note of this and subscribing to Squarespace. However, the constantly evolving nature of the online advertising ecosystem ensures that new ways of attracting and acquiring customers are constantly developing and changing.

I believe Squarespace's advertising strategy should mirror its overall end message to users- provide a simple, minimal, and useful experience rather than adding to the clutter and congestion of an already messy web.

When thinking about the emerging advertising strategies of 2014, I would structure my strategy by keeping several ideas in mind...

The Core Channels

I think that Search remains one of the most successful methods overall for Squarespace to continue pursuing due to the intrinsic nature of "search": when someone searches for something, it is because they are explicitly looking to achieve a goal (in this case, creating a website/brand/online presence/place to store and structure their ideas). Squarespace can continue to differentiate itself in this channel by developing more and more targeted Adwords campaigns designed to appeal to niche groups within its verticals, while also continuing to target the broader group of "anyone looking to create a website". Not only are targeted searches more effective because they appeal directly to small groups rather than casting a wide net, but they are also cheaper due to lower competition.

I would group Social advertising in this field as well. Although it is much newer than Search, the added context of social validation makes Social a valuable channel that isn't going anywhere. Social also allows users to be targeted based on extremely detailed fields such as Life Events and interests. Social is even melding with Search in situations where a user searches on Google and uses the social validation of Google+ to choose certain pages/products over others. The possibilities are endless for the added functionality of Search/Social (someone searching for Squarespace is able to see the number of their friends who have Squarespace websites on the search results page).

Recent and Emerging Trends

More than ever, companies are experimenting with different formats as technology expands what is possible with advertising. I believe that companies are finding out...

What works organically

TrueView videos on Youtube which only charge for full views and give users the power to skip ads that are irrelevant to them, thereby saving time for the user and money for the advertiser. Squarespace can leverage existing video campaigns in this channel.
Certain types of Branded and Sponsored Content. Squarespace developing video content designed to help users "develop their online brand" or "create an e-commerce store" and sponsoring it across websites such as Youtube and eHow. Note: This should only be done on websites that match Squarespace's brand image and target audience.
Additional forms of media like Podcast advertising. This channel is so great because Podcasts have loyal followings in very specific areas of content. Therefore, Squarespace can target specific podcasts (or podcast networks) such as Designer podcasts or Small business podcasts, and thereby target audiences who would actually benefit substantially from Squarespace rather than focus on broad groups of users unlikely to convert after hearing an ad.
Limited amounts of Remarketing, which allows Squarespace to follow people who have already visited the site and remind them of their interest in subsequent days. Conversions are higher for this method because you are targeting users who have already expressed interest in Squarespace through their visit.

What doesn't work (and can harm a company's brand despite acceptable conversion rates)

Certain Sponsored Posts on facebook that take advantage of the wonders of social validation but end up privacy-related controversy that overshadow the inherent benefits of advertising to friends of people who have liked your product
Native stories that are TOO sponsored (stories that show up in the feeds of content sites but come across as advertisements rather than actually useful content because they don't add anything useful for the publisher's audience)
Ugly and obtrusive banner ads that clutter a user's experience and could possibly even cause harm to the advertiser's brand image. Overall, Squarespace should limit its banner presence on most publishers due to the overall "noise" that banner ads cause on most sites where they are present
Unmonitored Affiliate programs- while affiliates can be an effective, high ROI way to acquire customers, affiliates should be monitored to ensure they are not using deceptive practices (such as forced clicks and false advertising) to draw traffic to Squarespace

The Possibilities for the Future

The online advertising industry is maturing and is still relatively in its infancy. But that newness is so exciting because there are so many untapped methods for acquiring customers that haven't even been considered yet or are just beginning to emerge. Here are a few areas I find really exciting...

Interactive advertisements that take advantage of technology advances to allow users to play around with Squarespace design tools without ever leaving the page they are on; ability to test the product before clicking essentially guarantees higher conversion once an ad is clicked
Added "targetability" in facebook/google (i.e. targeting people who have recently added a life event to their timelines, such as starting a business, getting engaged, or joining a band. These life events are prime examples of Squarespace's desire to target the right customer at the right time)
MOBILE- Mobile is where everything is going (especially for certain demographics such as teenagers, whose online presence is essentially driven by mobile rather than desktop); I think companies need to become completely agnostic of devices in their advertising strategies and should instead focus on delivering the right content to users at the right time, whatever device they are on
Leveraging data from business aggregators like Yelp to determine what types of businesses are least likely to have websites listed and then targeting those verticals directly
Targeting additional verticals directly, such as Teachers (posting syllabi and homework)

The ever-changing nature of the world of online advertising is fascinating and I would love to help Squarespace define its strategy going forward and then help manage and run its efforts across multiple channels and verticals.

Thanks for reading,

Alec