Vaibhav Rastogi, a Group Product Manager at Pinterest(US Office), leads the product team responsible for collecting conversions, identity resolution, and ads attribution. This data drives ads models and performance reporting at Pinterest, an American image-sharing and social media service.

Vaibhav embarked on his Product Manager journey at BloomReach, Bangalore, managing the Search and Personalization product. After BloomReach, he relocated to the US, serving as the PM for Ads Targeting at Microsoft, Redmond. His leadership at Microsoft Ads resulted in over $100 million in incremental revenue through improved audience targeting. Vaibhav's professional journey also includes roles at Wipro and Oracle.

Coming to education, Vaibhav completed his engineering degree from IIIT, Allahabad, and pursued an MBA from IIM-Indore. Vaibhav, beyond work, finds joy in gardening, nature walks, and exploring new places through food.

Let's learn more about Vaibhav and his intriguing PM journey.

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How to move from APM to PM quickly and when to choose between a startup and a large company for optimal career growth?

Thank you for the question. Delivering impact is key to swiftly progressing from APM to PM. Starting my journey at BloomReach, a smaller company, provided a steep learning curve due to fewer people and numerous problem-solving opportunities. Fast execution and cross-functional exposure allowed quick growth—four levels in five years. Transitioning to Microsoft later was facilitated by the brand's influence. Swift progression relies on delivering impactful results.

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As a final-year medical electronics engineering student aspiring for PM intern roles in SaaS, what skills should I showcase on my resume to stand out?

Great question. The candidate-to-job availability ratio for PMs is more skewed than for engineering jobs. Thus, finding your first break can be challenging. For me, it was tough to secure interview calls, so I applied to any small company that would consider me. Prepared using “Cracking the PM Interview” and engaged in mocks with friends. After a few rejections, I finally had a few offers. My plan was to get my foot in the door and have the PM title on my resume. Subsequent job searches became easier.

So my advice is to look at smaller companies willing to take a risk. Prepare by improving your knowledge of the technology business so that whenever you get an opportunity, you can capitalize on it. Projects showcasing product management skills can also help during interviews. Some resources I like are:

• Stratechery by Ben Thompson: Great insights and analysis of the Technology business
• Lenny’s newsletter: Insightful articles on product management
• Occam’s Razor by Avinash Kaushik: Newsletter discussing problems in digital marketing
• Shreyas Doshi on Twitter

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Can you share how your day looks like as a GPM at Pinterest?

Each day is different, but a typical day involves looking at priority tasks and ensuring progress for myself and the team. It's easy to fall into the grind of attending meetings and not making progress on things. So, I have a list of important or urgent things I need to complete, and I usually start my day by making sure I have dedicated time to make progress on those. Then there are meetings for stakeholder alignment, ideation, and sharing status. I also try to fit some learning time where I read about things that interest me. Taking short breaks during the workday is important for me to keep my focus.

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Whether moving out of India was a conscious choice or life took you there? Also, what are your long-term career plans in terms of work location?

Great question! I spent a large portion of my working life in India, and I love Bangalore. My wife’s employer gave her an opportunity to move to the US, and we thought it would be fun to experience a new culture. It is also better in terms of PM opportunities and compensation. I relocated with her on a dependent visa and found a job once in the US. I would love to come back to Bangalore in a few years.

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Reflecting on your diverse experience, how do you navigate challenges when transitioning from one product management role to another, especially in different domains? What strategies have you found effective in quickly adapting and contributing value to new product landscapes?

Thank you for the question. This is an often-overlooked aspect of job transition. It is hard to change domains, and as one grows senior, it becomes even harder to make an impact in a new domain without deep knowledge. I spend the first few weeks trying to build mental models, working back from the customer, and asking lots of questions. 

For example, let's say you're a new Ads PM; you may start by asking why advertisers want to advertise on your platform. What tools will they need to make sure this is a good investment? How are they comparing platform A and B and other similar questions?

Having said that, there is value in specializing in domains. For example, I've been in the Ads domain for almost 6 years, and I can compound my impact through the knowledge I've gained over the years.

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As a GPM, how would you deep dive into a business's needs and objectives to prioritize features when you are catering to enterprise and mid-size businesses simultaneously?

This is again a great question. I'll start by understanding the stage and size of the company. If it is a small company, it is better to target a specific customer segment (whether Enterprise or SMB) and make sure the product resonates in that segment. However, the question implies we already have product-market fit and are catering to multiple customer segments. Then it becomes a question of where the company sees the most opportunity and the investment needed to tap into the opportunity, i.e., RoI. For example, the enterprise segment may be saturated, but the mid-market segment can deliver superior growth, and assuming the investment is reasonable, I would put more resources into building for the mid-market segment. This would probably leave some opportunity untapped, but our objective is to maximize returns for the available resources. Practically, we build for multiple segments at the same time and weigh the investments by opportunity size, i.e., some investment for enterprise and a lot of investment for mid-market.

I realize that the answer above seems simple, but it is difficult in practice since there are many variables.

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Just wanted to ask what you will suggest to someone who wants to transition to PM from testing? I know what skills the PM requires, but how can I show these skills and convince the recruiter that I'm the best fit?

Convincing recruiters and convincing hiring managers are 2 different topics. Hiring managers (HM) share a set of requirements with recruiters, and to make their task easier, recruiters use keywords to filter resumes. Transitioning to PM without prior experience is difficult to pass through the recruiter screen unless the HM has specifically asked for it.

A better approach is reaching out directly to the HM or going through referrals. If you can make the transition from Testing to PM in your current organization, that is the easiest, or you can look for companies where both Testing and PM roles exist and plan your transition over the next 2 years.

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While thriving as a Software Developer at Oracle, my sights are set on Product Management. Seeking advice for aspiring PMs like me to navigate the path from code to customer.

Thank you for the question. Oracle does have a PM role. It'll be easier for you to make the switch to PM internally. Once you have 1 year of formal PM experience, it is much easier to look for PM opportunities. The alternative is to look at startups as they're willing to take risks.

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What are some of the skill-sets you look for when hiring a PM in your company? And how do these expectations for the skill-sets vary for a fresher and a PM with 2 years of exp.?

The candidate skill-set depends on the job requirements. For APM or a PM with 2 years of experience, I will not look for domain expertise. However, if hiring a Staff or Principal PM, I either look at domain expertise or some experience that is transferable to my current domain. Then there are basic PM skills that are tested for any PM candidate, but the difficulty varies:

• Customer centricity
• Being able to set goals and guardrails
• Collaboration and influencing
• Comfort with engineering systems - doesn't mean a prior engineering background but being comfortable discussing high-level details
• Ability to logically structure an ambiguous problem

For a PM with 2 years of experience, the bar for product sense or customer centricity will be lower than for a Staff PM.

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Could you tell us more about the helpful pointers for growing as a GPM?

Thank you for the question. For the first few years, I was focused on execution, and as long as I was helping the team execute well and deliver impact, I grew. It also helped that I was at a startup, so the feedback loops were faster. I had to learn how to thrive in a larger company where there is a lot more emphasis on upward communication and stakeholder alignment. I also realized I now need to identify impactful problems along with execution, and if I do that consistently, I'll grow. At some point, if you're looking for a managerial role, you have a supportive environment, and you've been delivering impact, the transition to manager happens, and then you need to learn a different set of skills.

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Coming to mental models, Can you suggest a few approaches? How do you go about them?

I try to put my mental models to paper as that helps me think. To build my mental models, I try to identify all the input variables that can impact the output. Then I try to look at how much weight or importance each of the variables has and iterate on this with each product ship. Taking an example from Ads - Let's say you're a PM for Facebook Ads and your goal is to get more spend from advertisers. The input variables could be actions or outcomes that are important to advertisers (like site visits or product purchases), preference of tools (like API vs UI access), being able to integrate data into their source of truth, availability of formats (like video ads vs image ads), etc.

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