9 Questions with Sheldon Fernandez of DarwinAI

July 11, 2019

Meet Sheldon

Sheldon Fernandez, CEO of DarwinAI, is a seasoned executive and respected thought leader in the technical and enterprise communities. Throughout his career, he has applied emerging technologies such as Artificial Intelligence to the enterprise. First, in his capacity as CTO at Infusion, the company he founded out of Waterloo with five partners that grew to 650 people. Then subsequently, at Avanade, the organization that acquired Infusion in March of 2017. Through his career, Sheldon has coupled his entrepreneurial endeavours with non-technical pursuits, resulting in an interdisciplinary approach that is critical to the intelligent application of AI. He completed a Master’s degree in theology at the University of Toronto in 2008, with thesis work in neuroscience and metaethics and also pursued creative writing at Oxford University.

Best piece of advice you were ever given?

Two weeks after I got married a good friend - a wise and gentle soul - told me “there’ll come a time when you’ll have to choose between being right and being happy. Choose the latter.” I’ve never looked back.

"There’ll come a fork in the road when you’ll have to choose between being right and being happy. Choose the latter."

What books are you reading at the moment?

A biography on John Steward Bell, one of the underrated physicists of 21st century who made major contributions to quantum mechanics.  The science lover in me is alive and well.

When did you realise you were wrong about something?

More often than you’d think, but a good leader confronts their mistakes with honesty, humility and a plan for action.

What is the biggest obstacle you’ve faced along your career path and how did you overcome it?

Midway through my previous venture I was fundamentally unhappy and lost on a number of fronts. It was an extremely difficult time, but I was fortunate enough to have partners who allowed me to take a sabbatical to centre myself.  After a foray that included creative writing, a Master thesis, and volunteer work in Kenya, I came back energized and with a renewed appreciate for what we had built together.

How do you ensure you focus on the right activities?

This is constant challenge in my current role – to not get so lost in tactical execution that I forget to focus on the more strategic elements of our business. To combat this I set concrete deadlines around strategic deliverables (e.g., a presentation to our company on our strategic plans for ‘X’) that I hold myself accountable to. 

"Set concrete deadlines around strategic deliverables"

What one piece of advice would you give a CIO looking to develop a new modern culture in their technology organisation?

It has to happen organically and with genuine buy-in from stakeholders and staff. I’m a big fan of the Google study which found that high performing teams are the result of ‘group norms’ – traditions, behavioural standards, and unwritten rules that govern how teams function when they gather.

I would encourage CIO's to think about how they can instil such norms in their organizations.  Without them, you are left with ineffective platitudes.

What is the most interesting technology to you right now?

I’m biased of course, but Artificial Intelligence, and specifically Deep Learning. We are truly at the tip of the AI iceberg and the disruption it will entail. 

"We are truly at the tip of the AI iceberg and the disruption it will entail." 

What is the best example you have seen of an organization that has used technology to transform itself?

I’ve been deeply impressed with Satya Nadella. His transformation of Microsoft from their tranche of stasis to first-tier innovator, particularly around the cloud, has been nothing short of remarkable.  

What is true that almost nobody agrees with you on?

The falsity of the Twin Prime conjuncture. I’ve a found a truly marvellous proof of this theorem but the margin is too narrow to contain it. (The math geek in me is also alive and well).

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