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Meet Keren Moynihan: a woman on a mission to help companies predict the future

The idea of predicting the future might sound like a sci-fi plot but Keren Moynihan, Co-founder and CEO of Boss Insights, is helping private companies predict performance in real-time using AI. She is an advocate for data privacy, creating AI that unites rather than divides society and collaborative approaches to democratizing access to capital. We caught up with her to find out about her professional journey from her brief stint as an actor to her advice for making a mid-career transition.





My first job was… I loved working as a swimming teacher.  It’s amazing to teach people to swim whether they’re six months old or adults.  It opened my eyes to what happens to people as they grow up.

My proudest accomplishment is… I’m the proud mother of four babies, three humans and one startup.  For those new parents out there, they’re all under 6 … consistent sleep is just around the corner.

My boldest move to date was… Leaving banking at RBC to start working at a startup or paragliding in Rio – it’s a toss-up

I came up with the name of my business… Boss Insights predicts private company performance in real-time.  The company name is a play on words. It’s an acronym that stands for Back Office Software Systems.  Also, we deliver analytics and revenue generation opportunities for capital provider and entrepreneurs, like a boss.

I would advise anyone thinking about a career transition to… Think of the memories you’d like to have and find the working situation that will let you take steps towards building that reality.  After making sure your career will meet basic life requirements, look for a job that will inspire and fulfil you over one that offers prestige.  One colleague of mine inspired me so much by leaving her teaching job to start in sales for a tech startup. She was no ordinary teacher, finding positions in international schools and travelling the world.  Her friends and family were surprised that she’d give up summers and a pension for a career that was riskier. Fast forward years later, and her sales job has fulfilled her, is still travelling regularly, both for work and play, and is more inspired.  

If you’re not sure about what you’d like to do, speak to people to see how they’ve solved the ‘career conundrum’.  Life has a way of providing opportunities. 

My greatest advice from a mentor was… “We have two ears and one tongue so that we would listen more and talk less.” — Diogenes

My biggest setback was… My first startup tugged at my heartstrings.  Efficiency Capital offered capital to large buildings to make it more energy-efficient.  It was a triple bottom line, meaning that it helped people, planet and profit. The main issues with the business was offering a solution that the market wasn’t ready for and creating a business model that would work for the people involved.


“We have two ears and one tongue so that we would listen more and talk less.”


I overcame it by… It sold recently and is still up and running.  Even though it’s not part of my daily experience, it makes me happy to know that they’re in operations and by succeeding there’s a greater good happening at the same time.

If I were to pick one thing that has helped me succeed, it would be… Recognizing that failure is really an opportunity for greatness.  There’s power in knowing that what you can change in yourself will lead to better future outcomes.

I surprise people when I tell them… I worked as an actor for two years.  I got the chance to work in 40 different projects and test the limits.  The key part of acting is to focus on relationships – that’s a takeaway that’s helped as I’ve gone through other experiences.

I stay inspired by… Letting what happens around me have impact enabling me to grow and change.

The future excites me because… We can be the change we want to see in the world.

My next step is… Moving Boss Insights from a startup to a scaleup company playing in the global marketplace and connecting with as many people as possible along the way.