AI Assistants

November 19, 2014

Predictions are dangerous to make, but I’m going to try anyway: I think AI assistants will be one of the next great enterprise SaaS opportunities. Here are a few reasons why:

1. A large existing market to provide a cheaper substitute for

~$110BN+ of secretary and EA labor costs

  • 2.56MM secretaries and administrative assistants in the US making on average $34k per year for a total of $73.41BN in wages
  • 755,210 executive secretaries and executive administrative assistants making on average $51.87k for a total of $39.17BN

I don’t have evidence for it, but I intuit that scheduling is becoming an increasing challenge for more people than ever before:

  • Teams are increasingly distributed
  • More work is done on the go but scheduling is hard to do on mobile
  • More of the workforce engages in higher cognitive activities that require significant collaboration

2. Freemium product & market expansion

  • An artificial assistant would substitute for existing labor, but the lower price point will also expand the addressable population as the product is within the budget of more employees and it can increase their productivity

  • A free self-serve product may make it compelling for individuals to try having a personal assistant when the upfront cost used to make it prohibitive to even consider. Free power users can naturally gravitate into paid users based on utilization thresholds

3. The infrastructure is ready

Most modern companies are now on the Google Apps suite which is comparatively simple for 3rd party technology to integrate with and for user’s to authorize (see RelateIQ, Mailbox, Streak CRM etc.)

I haven’t diligently studied the latest advances, but anecdotes suggest that natural language processing is now (or soon will be) smart enough to parse and engage in conversation:

  • Siri and voice recognition has made significant advances, and text is much easier to parse than voice
  • IBM’s Watson parsing jeopardy questions (this does have a defined answer format though)
  • RelateIQ intelligently parses emails and suggests follow ups you have missed

4. Winner takes most market

This is pure conjecture but I think there is a compelling case this is a winner takes most market. My initial basis for this argument is that:

  • The breakout product will own a powerful distribution channel (signatures in email) generating the most efficient customer acquisition (similar to how Survey Monkey acquires customers through each survey)
  • This is a data product, and the early breakout will have the biggest head start on supervised learning which may enable a fundamentally better product
  • I think that bot-to-bot by the same company will end up with a superior experience to one where two different AIs are trying to compete (though that could be hilarious)


I think the leading company will differentiate through better technology and exceptional marketing. EAs can do a multitude of work, but the winner will start with a monopolistic focus on scheduling and expand from there as necessary.


AI Assistants was published on (revised: ) Miles Grimshaw

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