Sean Diwan

CIO at Advanced Group of Companies

Can you please provide a little introduction about yourself

Based out of Chicago, Illinois, Sean Diwan is the Chief Information Officer (CIO) for Advanced Group’s family of companies, responsible for all aspects of technology globally.

Over the past 18+ years, Sean has successfully held various CIO, CTO technology leadership roles across a variety of industries (Healthcare Providers, Financial Services, RCM, Medical Devices, Global Education firms, Banking, Insurance, Tech startups, etc.) for prominent firms globally with added focus on turnarounds, scaling, optimization, M&A, tech stack modernization, digital transformation, product development & engineering, cost efficiency, and operational excellence.  Sean holds a BA from KSOU.

What path have you taken to your current position? 

My career started actually in the law firm space where my first job was as a Litigation Paralegal Assistant on one of the largest Insurance litigation cases.  That is where I entered the Technology world - where I helped in setting up a new Litigation Document Management system and a National network of communication  - from there I worked in various industries: Law firms (Director, IT), Commercial Real Estate firm (Global Principal IT), Chip Manufacturing (Director of Software), Banking, Insurance (VP of IT/CTO), Telecom, Medical Device Mfg, Healthcare RCM firm (SVP of IT/CTO), Healthcare provider firm, and now with a Clinical Trial research organization (CIO)

Has it always been your vision to reach the position you’re at? Was your current role part of your vision to become a tech leader?

Not really. I was most interested in pursuing a more meaningful contribution path. Along the way however, as I did my best to bring Business and Technology together, thats where CTO/CIO pathway opened up and I followed it along the journey.

Have you had a role model or mentor that has helped you on your journey?

I had several mentors/role-models along the way (I would have to get their permission to quote them for sure).  But, the embodied everything I was developing my muscles in - things like: Resilience, Dealing with difficult people, staying current, dealing with ambiguity, etc..

How do you see the role of the technology leader evolving over the next 5 years?

With the recent hurricane that hit us all - AI - I see the role evolving and getting even closer to running/growing the business via enabling key capabilities such as AI, Data Harvesting - and still focus hard on Cybersecurity and Core Technologies - along with User / Customer Experience improvements - a handful for sure.

What skills do you think leaders of the future will need in order to thrive?

Business acumen, Emotional Intelligence, Ability to Listen, Leading People, Tech savviness, and Financial acument.

Is there anything in particular that you would still like to achieve in your career or what is the next step on your journey?

I would love to write a book or something to that effect to share my learnings that could help others learn from my journey.

What advice would you give to aspiring technology leaders who are just starting their careers?

It's not about today or tomorrow, it's about the day-after-tomorrow...

"It's not about today or tomorrow, it's about the day-after-tomorrow..."

What has been your most significant achievement or proudest moment as a technology leader?

Balancing the demand of Innovation, Operations, Cybersecurity, Business Growth, and People Leadership.  Staying focused with a clear "incremental" set of metrics for each - not worry about "boiling the ocean" - gain the next 10 yards, don't focus on the touchdown just yet - it's about the next 10 yards - and then keep going!

How do you measure and communicate the value and impact of technology initiatives to other business leaders and stakeholders?

A CIO Dashboard that lists key metrics covering Running, Growing, Protecting the business

What has been your most significant achievement or proudest moment as a technology leader?

Top 25 CTO in Healthcare in 2023

A big thank you to Sean Diwan from Advanced Group of Companies for sharing his journey to date.

If you would like to gain more perspective from Tech Leaders and CIOs you can read some of our other interviews here.