Mentor Spotlight: Ajit Dipak - Senior Product Manager at Amazon

Curiosity, Career Transitions, and A Desire to Learn.

Nadine Okoeguale
December 9, 2020

Ho - ho -hey! 👋 🎄

Every week, we share insights, advice, ideas and stories of a diverse range of techies. Today, we are bringing you a different, and more experienced perspective. How do you see a story from someone who has been in the tech industry for over three decades?

Ajit Dipak is one of the project mentors we have in Co.Lab’s current cohort. That’s all I’ll say. Learn the rest from my interview with him. Be ready to forward this article to friends, screenshot and take notes. It’s loaded!

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So Ajit, what do you do?

I’m currently a Senior Product Manager Technical at Amazon. The area I work in is Last Mile Technology. Think about how Amazon delivers packages to your doorstep. You order online or use the mobile app but how does the package actually get to you?

It starts from the warehouse, called the first mile, to your country or area. There’s the middle mile from the airport, train station and shipping container to the larger regions that you’re in. Then there’s the last mile that is concerned with how your packages are getting from those stations, or what we call FCs (Fulfilment Centers), to your doorstep. In the chain of movement, there are as many teams and organizations as you can imagine but I work in the final link, the last mile, and specifically, my work is involved with the app that Amazon drivers use.

My particular area of ownership within the app is what is called ‘doorstep services.’ These are any specialized procedures that the driver may have to follow with the customer at the doorstep. For example, in certain jurisdictions, Amazon delivers age-restricted goods like alcohol. We have to be very careful with who receives these packages and will need to verify the identity of the receivers and be sure that they fall within the accepted age of majority. It’s a really fun and interesting portfolio because there are so many use cases around the world and I’m involved in a lot of them.

Ajit image
Thanks Ajit, for sitting down with us!

So how did you get there?

Well, it’s been a bit of a journey. I’ve been in product management roles for the past seven years in different companies. There have been three distinct arcs in my career so far: I started as an engineer then moved to engineering leadership managing teams, then teams of teams and now I’ve been in the product management space for the latter part of my career culminating in my current role at Amazon.

I actually started programming professionally when I was 18 and still in high school. I went to university to study Computer Science at McMaster University; it’s well-known for its research and innovation in the medical field. Through my network, I was very lucky to be programming at a research centre. My first job was actually programming software for bone mineral densitometers.  My friends were working fast food jobs or at camps and there I was, cutting my teeth on medical devices. I felt extremely lucky and happy to be doing that and it was a job I kept going back to every summer as I went through university.

When I graduated, I had a lot of programming experience and a clear intention to focus on technology moving forward. That’s how I started into my first job. I worked about 10 years in programming roles working my way up from junior engineer to senior engineer and then engineering team lead.

What values do you live by, career-wise?

For me, the two main things are curiosity and a constant desire to learn and grow.

I’m the son of a librarian. My parents really value education so it was always a big part of my childhood.  When I started thinking about what to study at my post-secondary level, I asked myself, “What’s something that’s going to let you stay broad?” I thought about computers, which were relatively new back then in the 90s. I just had this intuition that computers were going to be everywhere. I’m very lucky that my teenage premonition came true. (laughs)

Back to the question,  curiosity and a desire to learn have just been big parts of my career. They’re the reasons why I’ve moved around in different industries and explored so much. They are also the reason why I haven’t just stayed in one job function. I had been programming since I was 18 and when I got to my early 30s, I felt I had about a dozen years of experience in hands-on keyboard programming work. I wasn’t having fun anymore and felt I had more to offer and that caused me to start looking into engineering leadership. After spending a lot of time working in leadership positions, I realized I was enjoying the ‘why’ of business as opposed to the ‘how’ that is, how to build software which I had already spent the most part of my career doing working as an engineer. Thinking more about the ‘why’ and ‘what’ to build in a business  led me to product management which I’ve been in for the last couple of years.

How did these values bring you to Co.Lab?

When you’re curious and focused on your own learning, there is a natural desire to pass it on. In my career, I’ve been told on many occasions: “You’re very good at teaching.” “You’re very good at coaching.” As someone who has been very intentional about their career, I’ve always thought about how I could be the best at whatever it is that I did. Most recently, being in product, I think about what it’s like transitioning into product management and anything I can do to pave that road for the next generation of product leaders to have the right introduction into the field, I’m really happy to do it.

What’s your experience been so far mentoring Co.Labbies?

It’s been very rewarding. I’ve found that the time I spend with the cohort is energizing. They are eager to learn and the group that I have currently is filled with great personalities.  They’ve bonded very well and are getting along as a team.  It energizes me to spend time hearing their ideas,  listening to what their challenges are, helping unblock these challenges, passing on some wisdom where I can, and just giving them insight into how things are done in the industry. It’s been helpful for them and it’s certainly been helpful for me. I really disagree with the idea that mentorship is just a one-way communication. I’ve gotten as much out of the mentorship as I’ve put in and that is very gratifying. I’m really looking forward to Demo Day this weekend. I want to see what all the teams come up with and in particular, what the team I mentor is able to put together.  

What advice do you have for aspiring techies?

Understand why you’re working in the area that you are. It goes back to the curiosity I mentioned earlier. People that are intrinsically motivated, the kind of people that really like a problem space or like a technology those are the kind of people that invariably are the most successful because they are just constantly learning and getting better and sharpening their skills. One of the most amazing things about the world we live in now is that there is so much you can learn on your own through the internet. I’d encourage people to remain curious and see how they can use that to their advantage.

I’d also encourage people not to fall victim to what they see as conventional wisdom. What I mean is the idea of:  ‘the only way I can be in technology is if I take all these math and science courses and I learn to program.’ Not at all. As a matter of fact,  some of the best people that I’ve worked within technology came from completely different backgrounds at first and then pivoted their way into technology. I personally think that it sometimes makes for a more well-rounded and effective person in technology. One of the best programmers I ever worked with in my whole career came from a Geology background.

You’re going to be learning for the rest of your days whether it’s in technology or not, so make some time and be intentional about your career. Don’t put limits on what you can do in the future. Instead, spend that energy and that time being curious. Keep learning.

Have you read any books that have helped fuel your values?

There’s a book called Drive by Dan Pink. I read it at the beginning of my journey into engineering leadership. It was such a great way of explaining how what we think of managing and leading people is very much outdated. And even if you don't intend to be leading people, the book is so helpful as a way of explaining how we all work, what motivates us, what excites us, and what gets us to perform at our best. It really opened my eyes as to how we work in the kind of world that we live in now and that work is defined by outcomes. Drive is a book that I read over 10 years ago, but it's stuck with me a lot.

book recommendations
A few book recommendations!

Another author that I would encourage people to read is Cal Newport. He wrote So Good They Can’t Ignore You and another called Deep Work. The most recent one is called Digital Minimalism. He is all about getting people to focus and produce their highest value. He talks about how the most successful careers are about people that have unique, deep skills that are hard to replicate. To make his point, he uses examples, not just in technology, but really all over.

I've read all the books of these two authors and I've been on their newsletters. I follow them keenly because I've just really resonated with what they have to say.

Ajit’s final pieces of advice to you…

  • Take advantage of the opportunity that’s in front of you
  • Stay plugged into communities (like Co.Lab!)
  • Update your resume all the time even when you’re not job searching
  • Speak to people who can help you with your next career move
  • Constantly challenge yourself
  • Stay curious

Awesome read, right? I told you it’s loaded! What was your favourite piece of advice out of all of these? ✨ Don’t forget to comment, like and share this post if it resonated with you… and we will see you next week!

Co.Lab provides aspiring techies with practical, team-based product experience.  We run a multi-week practical education program for product managers, designers and developers. To learn more about Co.Lab and how you can participate, join us on Demo Day this Saturday and visit our website here.

We are looking for mentors of all backgrounds - engineering, design and product management! If you are interested in mentoring at Co.Lab, reach out to Helen at

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