CEO on training AI-driven personal assistants

Where does your enterprise stand on the AI adoption curve? Take our AI survey to find out.’s digital personal assistant that employs AI to organize a user’s life is expected to enter beta this summer. Known as Charli, this personal assistant promises to do everything from finding all related documents in email and cloud storage systems to organizing receipts and tax filings.

VentureBeat sat down with founder and CEO Kevin Collins to better understand how AI is about to transform the way we all work.

This interview has been edited for brevity and clarity.

VentureBeat: What exactly does Charli do?

Kevin Collins: It’s really about keeping yourself organized and finding what you need. If you go into email and try to find something you’re looking for, it’s a nightmare trying to search for it. If you’re going into your cloud storage to find documents that you filed a year ago, it’s a nightmare to find them. Charli is really about keeping your digital content organized, allowing you to find things instantly when you need to find them. That includes files that you might be keeping in email or cloud storage, but it also includes links to the internet. We get inundated with links to every piece of content that’s out there. [Keeping] track of it can just be handed off to Charli.

VentureBeat: Sounds like everybody can now have their own digital assistant?

Collins: We wanted Charli to be like that personal assistant for you. We’ve got a whole natural language processor in the front end of it that Charlie can understand. For example, if I say “Charli, show my expenses for this month,” it will understand that. It’s also designed for speech that we haven’t yet integrated. We haven’t integrated with Alexa or Google. We’re still at an early stage. We’re coming out of our beta program in the summer. The whole idea about Charli was providing a personal assistant for me. The name Charli is a bit of a play on chief of staff. We dropped the E because we wanted [the name] to be gender-neutral.

Venture Beat: What is the business strategy for Charli?

Collins: There will be a free version of Charli so that people are comfortable with it just doing the organization. If there are more sophisticated use cases, there’s going to be a subscription-based service. If you sign up for the premium package or professional package, you’ll get different access to different aspects of the AI. For example, the pro package will allow you to enable Charli to read your invoices and receipts, pull out the very specific information, and then send that off to QuickBooks for you.

Venture Beat: What role do you think AI has to play in this helping people and kind of navigating their work from anywhere scenario?

Collins: Getting back to that pre-pandemic normal isn’t going to happen. There’s going to be a lot more remote work. That’s going to put a lot of pressure on organizations to be far more productive with the remote workers. There’s no longer the ability to walk down the hallway to talk to somebody. There’s no longer the ability to just put something on the internal mail and send it off to somebody. There needs to be a new way of getting employees productive, and that means more automation. AI has a massive role to play.

Venture Beat: Will employees embrace that idea, or are they fearful of AI?

Collins: When we talk to our customers and our users, they’re quite excited about the potential of AI. They see AI taking a big load off for them. There’s a glimmer of hope that AI can take some of the pain away, but there is an undercurrent of fear of what that means from a job perspective. Is it going to take jobs away? And the short answer to that is yes. You will see a shift in the labor market. A lot of these manual tedious jobs that require a lot of people are now going to go away, but there’s going to be demand for other types of jobs, especially in skilled labor. There is a shift in the labor market that’s going to affect different people in different ways. Some are going to be negatively impacted, while others going to be positively impacted.

Venture Beat: What else are people fearful of when it comes to AI?

Collins: The other fear, and I think it’s a real one, is that there is an inherent bias in AI. We’re starting to talk about that a lot more. There’s more emphasis on auditing the AI algorithms. There’s a lot more emphasis on making sure that they are behaving in a standardized way that is positive rather than negative. AI is mathematical models. They’re trained to behave a certain way, and they’re trained by people and organizations. There is an underlying fear that they’re going to be trained in a negative way.

VentureBeat: Do you think we will get to the point where we have instances of AI that are optimized for opposite outcomes that will eventually do battle with one another?

Collins: I would say yes. We want Charli to be biased [in your favor] because it’s your personal assistant to a certain degree. But we need to introduce diversity into that, so that means competing viewpoints. If you’ve got various decisions that have to be made, there has to be a decision criterion that comes from diverse AI models. You have to be able to consult those diverse models and make a decision on which one suits the case or the instance. AI has to be very contextually aware, which means different training, different algorithms, and they have to compete against each other for the right decision at the right time for the right reason.

VentureBeat: Don’t I just wind up with multiple personal secretaries making different recommendations based on their biases?

Collins: That actually gets into some of our intellectual property because we don’t want multiple personal assistants. You want that one personal assistant, but you want that personal assistant to have a diverse set of inputs in order to make the right decision for you. There are competing AI models that have to really fight each other in order to make a confidence-level decision for you. It’s your personal assistant inspecting these competing decisions and making the right decision for you. You don’t have to deal with multiple personal assistants, you deal with one, but you want the confidence in that one to make the right decision.

Venture Beat: How long does it take Charli to be trained?

Collins: It’s a loaded question. The short answer is this is really hard. To get Charli to be brilliant at doing all this takes a couple of years, but for Charli to learn some basics to understand how to organize your life is quite quick. I’ve been using Charli now for a little over a year. Charli rarely comes back and asks me questions anymore, whereas at the beginning Charli was asking me a lot of clarification questions. It’s just not a matter of going to the shelf, getting a machine learning algorithm, and thinking it’s going to work out of the box. That doesn’t happen anywhere. You can go and get all these algorithms out of the box, but you have to invest in the data, the training, the testing, and the automation of the continuous learning processes. That is a very heavy investment. For other companies considering this, they’re really going to be in for a bit of a shock of how much work it is to get this right.

VentureBeat: How will we ultimately know Charli is getting it right?

Collins: We’ve invested a lot in guardrails because we need the AI to behave a certain way. There are a lot of guardrails around laws, restrictions, rules, and policies for humans. We need those types of constraints in AI as well. That is another heavy investment area because we just don’t want AI to think outside the box for us. We want AI to simply take the pain and aggravation of automation off of our plate. There’s a massive investment that went into testing AI.


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