Back when I was the CEO of Bit Stew, I was honoured to have an Executive Assistant.

I’ll be honest – at first, I wasn’t sure how an EA could help me. Since it was my first time working with someone in this role, I worried it might be more time consuming for me to onboard them and manage another person.

However, the minute that the EA set foot in my office, she took initiative and started learning about me and my needs. She picked up quickly on my processes (like how I organized my day, scheduled meetings and filed documents), as well as my preferences (like which hotels and airlines were my favourite for work travel).

Before long, she was making my office a much more efficient place. Once she learned about me, she became proactive in designing better workflows and organizational systems, and as a result, took a whole lot of work off of my plate. Her ability to problem solve and take care of things also reduced my overall stress levels. For years, she helped me more than I could have ever imagined.

That’s why I was devastated to lose her when my company was acquired. My productivity took a serious hit. Suddenly, I had to learn how to use a slew of new apps, as well as take on all the tasks she was so seamlessly handling. I realized how much I had come to rely on her and how she had, in fact, played the “Chief of Staff” role in my office.

I wanted my Chief of Staff back.

Feeling strained, I looked around to see what options I had available. In the absence of being able to hire someone, I assessed various technology solutions. There were virtual EA apps, but most were powered by people in the backend who actioned the tasks – meaning there was still a manual aspect to it, which imposed limitations. There was also the option of using assistants and chat apps like Alexa, Siri or others; but there was no easy way to set up the type of business workflows I was looking for.  All of these solutions would require coding or scripting and a lot of time.  These technologies were rigid and static, with very limited ability to learn, optimize and adapt. There weren’t many options.

That’s when I realized I needed to build Charli. Because if I was facing this problem, many others were too. This was not just my challenge – it was a challenge faced by busy digital workers everywhere, whether they ran their own business or managed people, projects, clients or accounts.

Working with my first few team members, we decided on the name Charli as a play on “Chief of Staff”. We also defined exactly what we wanted to achieve:

  • We wanted to have one app, like I had one person, that a user could turn to to handle all their time-consuming administrative tasks.
  • We wanted to be able to talk to this “chief of staff” across multiple channels (such as text, chat, email and voice) just like a real person.
  • We wanted to remove the burden of work, and the stress of having to remember everything, which many entrepreneurs and professionals face daily.
  • And, we wanted Charli to learn about the user – their needs, preferences, workflows and processes – rather than users having to learn Charli.

One year later, armed by a team of highly talented engineers, developers and data scientists, that’s exactly what we’ve done. We’ve built an app that’s solved my frustrations and more importantly, that has the power to help other business leaders too – from solopreneurs, to consultants, to business owners, to sales road warriors and more.  We are on an exciting journey and I’m looking forward to the moment when everyone will have a chance to meet Charli in the near future (more on this later).