Shopping cart optimization is one of the most often ignored area for small-to-mid sized ecommerce businesses.
This is a brilliant, simple solution - there are several "AI" cart abandon programs such as Upsellit.com, and other live-chat solutions, but Olark's inclusion of user data, cart value, and simple IM integration will make a big difference.
I'm 100% going to test this, and will report back about conversion results vs. other live chat or AI tools.
I worked on a team that developed one of the automated chat bot retention systems. Thanks for quoting "AI", as ours was really crude, but at the same level of other offerings. If memory serves, we cycled through basic pattern matches on normalized words to spit out canned replies and coupon codes to catch people leaving a landing page.
This is another one of those things that you'd figure people would hate and be annoyed by, but actually ends up being really effective. A company like ThinkGeek probably couldn't leverage it, but someone running a CPA weight loss offer definitely could. In a large way.
You nailed it - "Automated Chat Bot Retention System" - I've tested most of what's out there, always stunned by how well they work for most of your run-of-the-mill "offers" - I'm curious to see how this new system compares w/live operators and that level of simplicity - good solution I think.