Pranava Doctor, Group CIO at Allstate, recounts his journey from machine shop worker to tech executive at a multi-billion dollar insurance company. 

Avenue Code: Tell us about your personal career path. How did your career begin in India?

Pranava Doctor: I began by working with my brother in a machine shop making plastic molds until a friend of mine told me, “You’re wasting your time; I can introduce you to computers.” So at the age of twenty-three, I began working night shifts at a data processing company. My work involved making minor code changes, and when the developers saw my work, they invited me to become a programmer. I accepted and continued working in this capacity while completing my MBA. 

Two years later, some friends and I started our own business making, selling, implementing, and supporting prefabricated software for financial accounting, materials management, and payroll. In those days, imports were banned in India, so we had to “find” resources in order to build our own software. I used to travel to Mumbai and pick up books from sellers on the streets, then bring them back to my hometown and code. 

We didn’t have any money – not even enough to buy a PC, and our programming assignments were completed using our clients’ computers. For the first 3.5 years of starting the business, I worked from 8am until 2am and almost never took a day off. The business grew very successfully. 

AC: What brought you to the U.S.?

PD: I came to the U.S. in 1992 because of personal reasons. There were also more opportunities in the States for making money. I found a job as a developer for a banking software company and taught myself low-level coding. When someone told me I could make more money as a Sybase DBA, I obtained two Gateway 2000s, bought Microsoft SQL Server, and created a network at home to teach myself. 

I proclaimed to be a Sybase DBA and landed a job as a contractor in Des Moines, Iowa, which I accepted without even knowing where the city was – we had to search for it on a map! Two years later they offered me a job as a Systems Architect, which I accepted.

In 2000, I became the Lead Architect for the mortgage company division of Wells Fargo’s lending group. Then I was promoted to Chief Architect for the consumer lending group in 2003, which encompassed seven different business units. 

AC: What a journey! So how did you become CIO at Allstate?

PD: I joined Allstate in 2012 as the VP of Sales and Service Technology, after which I was promoted to be a Divisional CIO. I was also asked to lead the Architecture function. After Allstate acquired SquareTrade, I was deputed to be the CIO of SquareTrade. During this time, I commuted from Chicago to San Francisco.

In 2019 I came back to Allstate Corporate office and led the Program Management, Test and Release Management, and Technology Risk Management teams for all of Allstate. In 2021, I was asked to lead the architecture team along with our core engineering teams. 

Throughout my career, I’ve worked for companies with anywhere from 3 people to 300,000 people. I’ve also been involved in pioneering efforts at large corporations. Because of this, I’ve learned how to think like a startup, and yet keep in mind the considerations for a large scale organization. This helps me bring the best of both worlds together.

AC: Did you have a mentor who guided you through your work journey?

PD: My father passed away when I was 19. He taught me some life lessons which I still use on a regular basis. Being tasked to carry responsibilities from a young age made me extremely self-motivated and cultivated an entrepreneurial spirit that motivated me to seek out and learn from talented people in every company. 

AC: How would you characterize your leadership style? 

PD: My leadership style is centered around people. I strongly believe that bright ideas and innovative technologies mean nothing without people who want to succeed and have the skills to do so. I go out of my way to ensure philosophical and psychological buy-in from my team. I am impatient and want to accomplish goals very quickly, but I try to balance this with letting people take time to bake ideas in their heads so that they feel ownership of their projects and pour their spirits into their work.

AC: What advice would you give to leaders entering executive roles?

PD: Be mindful and alert. Always ask yourself, “Am I doing the right thing?” If you can look at your own actions from an outside perspective, you’ll be able to make wiser choices. Another tenet that goes hand-in-hand with this is remembering that it’s never too late to learn. There is something new to learn every day, and asking a question is more important than knowing the answer.

AC: What is your process for selecting digital transformation priorities and ensuring ROI?

PD: Digitization is about optimization. It means examining each business process and asking, “How can I take the physical aspect out of the equation?” That’s how you move the dial by either making money or reducing expenditures.

For example, claims adjusters used to travel to a physical site, take pictures, travel home, and then process an estimate. When you enable the same process to be conducted remotely, you’re removing the physical need for travel, and that’s where the cost is. Go a step further, and you have machine learning software that can examine the image of a dent in a car and estimate the cost to repair it. Uber followed the same principle by economizing the car to passenger ratio, and GE did it by installing sensors in engines to accelerate the repair process.

AC: Tell us about the current industry trends you see in the insurance space.

PD: When I was young, the goal was to become a subject matter expert. Today technology is evolving so rapidly that you don’t have time to learn a given skill in depth before market needs and resources evolve, yet you have to have enough knowledge to apply the right technologies to the right tasks.

To navigate this tension, you need to ask two questions: 

1) What are the business results I’m driving at? If you can’t answer this question, you’re probably too focused on technology for its own sake rather than technology as an enabler. 

2) What are the key factors for solving a business problem? In the insurance industry, every major carrier is working on the same innovations: machine learning, data science, artificial intelligence, 5G, etc. The trick lies in taking an outside-in perspective: instead of starting by asking what you can do with advanced technology, you have to start by asking which business problems you want to solve. 

AC: What keeps you up at night, whether it’s a problem you’re interested in solving or an idea you want to try?

PD: I’m always concerned about slowing down on learning. In fact, I just bought a MacBook Pro, installed Visual Studio, and am going to start coding just so that I don’t lose touch with the ground realities. If you’re constantly learning, your mind is constantly evolving and you’re going to survive and win in the market. 

AC: On a personal note, do you have a “passion project” you are working on now or would like to work on in the future?

PD: I love music, and I hope to learn to play the piano one day. I’m also reprioritizing my schedule to make time to read philosophy and poetry.

AC: Thank you so much for your time today, Pranava. It’s been fascinating to hear about your journey to become a CIO, and I’m inspired by your drive to continue learning every day!