How to Evaluate a Product Management Job

A guide for the next step in your career

Jasper Curry
The Startup
9 min readFeb 25, 2021


Photo by Victoriano Izquierdo on Unsplash

It’s been almost ten years since Marc Andreessen famously wrote about how software is eating the world. Ten years on, and it looks like he was onto something.

Product managers are needed in nearly every industry, and it’s not slowing down any time soon. It is an amazing time to be working in tech as you really do have the privilege and opportunity to choose your own adventure. That being said, you need to tread carefully, especially if you’re early in your product career. Product management is a nebulous field that can mean many different things depending on the team and organization.

Your work is going to fill a large part of your life, and the only way to be truly satisfied is to do what you believe is great work. And the only way to do great work is to love what you do. If you haven’t found it yet, keep looking. Don’t settle.
Steve Jobs

This post is broken into three sections:

  • Company evaluation — criteria to consider when you are thinking about getting a new job in product.
  • Questions to ask — a fundamental part of de-risking a potential job is asking questions so you understand what you’re getting yourself into. We go through 7 sets of questions that will help you do just that.
  • Resources — many people have written on this topic already, so I have collected some of the best posts about navigating your product career.

Company evaluation

There is no one set of criteria that will guide you to the perfect product job, and as I’ve learned the hard way, sometimes the only way to really know if a job is for you is to try it. That being said, here are some high-level areas to consider that can give you clarity as you go about your job hunt.

Company size and stage

How large of a company do you want to work for, and if it’s a startup, what stage is the most appealing? There is no right answer here. Generally, larger companies will have more structure and focus for their product roles. Early-stage companies will typically have fewer product managers with a broader scope and more ambiguity. Product School has put together a great article and chart (below) that provides an excellent overview of the common differences of product management at small, medium, and large companies.

Source: Product School

Product reputation/history

What is the company known for? Does it have a history of consistently delivering product wins? Be careful here. There are lots of large and successful companies out there, but their past success does not guarantee they are strong in product management. Many companies that saw their growth happen prior to the digital era are now struggling to adopt modern product management practices.

Evaluating the product prowess of an early-stage startup isn’t easy because they have a limited track record to evaluate. Even if they have a few public wins, this doesn’t guarantee they have a strong product team. There’s no silver bullet here, so you’ll need to use other criteria (people, investors, etc.) and conversations with their team to get a better understanding of how they operate.

You can also try talking with ex-employees (LinkedIn has a handy search by past company filter); I’ve found just performing this search to be helpful as it provides a sense of 1) how many PMs have left the company/how long they stayed and 2) where ex-PMs have ended up. If you do get to talk with someone, try to ask for concrete examples and take what you learn with a pinch of salt; some ex-employees may have their own agenda.

Business model

There are 3 primary ways to make money via digital products: subscriptions, advertisements, or individual transactions. These high-level buckets can be broken down further into 8 business models that you frequently see, sometimes combined together.

Source: Lenny’s Newsletter (Paywall)

I personally love subscription and marketplace businesses. Subscriptions provide an inherent alignment between the best interests of the customer and the company — if you can build things that improve retention or monetization by creating more value for the user, everyone wins! Marketplaces are are multifaceted and pose many challenging product problems that if elegantly solved can turn into a thing of efficiency and beauty (hello, Airbnb).

Of course, working at a company that monetizes via other models can be just as rewarding. While exploring opportunities, I highly encourage you to think deeply about what types of business models you find the most interesting; getting expertise in one will likely follow you throughout the rest of your career.


Who will be using the product you will be working on? The most common way to think about this is B2B (business-to-business) or B2C (business-to-consumer), but you can break this down via many other perspectives like industry, business size, or even social impact.

As a product manager, it will be your responsibility to get a deep understanding of your users, so take the time to understand who they are and what type of problems they experience. If you don’t find the users or their problems particularly interesting, think carefully about if the job makes sense for you.


Your manager will arguably be one of the most important people in your life. A good one can change the course of your career, while a bad one can make your life hell.

When considering a new job, do everything you can to learn who your manager will be. Once you have their name, investigate their background, professional accomplishments, publications, etc. If you have the opportunity and it’s appropriate, try to talk with people they currently and/or formerly managed. If after doing this research you’re not excited about the idea of working with them, proceed with caution.

If the company you’re considering is a startup, senior leadership is almost as important as your direct manager — do the same research.


If you’re considering joining a startup, you know they are inherently risky. This isn’t a bad thing, and you can learn a ton even from working at a startup that eventually fails. But you’ll probably have a much better time if the company isn’t constantly going through crises or desperately figuring out how to extend their runway.

Venture capital firms specialize in doing much of the due diligence I have described above, so look closely at where a startup’s funding comes from. Backing from a VC with a strong track record of success doesn’t guarantee a startup’s success, but it is a helpful indicator that shows other smart people see potential in the market, business, and leadership.

Questions to ask

Interviewing for a product position is a two-way street. You obviously want to prove you are capable and will excel at the job, but they also need to prove it is a job and environment you will be happy in. The responsibilities and day-to-day activities of a product manager can vary wildly depending on the team and organization, so it’s essential you are clear on what it is you are signing up for if you take the job.

One of the very few ways to learn more about a job opportunity is to ask thoughtful questions during the interview process. Below is a list of 7 sets of questions to use as a starting point for your conversations. This list is not intended to be exhaustive or run through in rapid-fire succession — use it as a guide to have deeper conversations. If during the course of your discussions you find things are getting too abstract or unclear, ask for concrete examples based on what is currently being worked on.

1) Who decides what gets built? How does the prioritization process work?

Marty Cagan has written several great articles on feature teams vs. product teams — I encourage you read them if you haven’t already. With this question you’re looking to uncover how much agency product managers have and how the team approaches product discovery. The answer to this question will be fundamental to your evaluation of the job opportunity. You don’t want to be stuck working on a feature team, but you also don’t want to be stuck on a team with no clear directive.

2) How does the team set goals, measure success, and get alignment with internal stakeholders?

There’s a lot in this so you will likely break it up depending on how deeply the first question was discussed.

  • Goals — What is the process for setting goals? Who comes up with the product strategy that ultimately dictates the focus of the goals?
  • Success — Do they have clearly defined metrics that level-up to top-line goals? Ask for examples and see if the team is defining success as shipping features or if they are focusing on the outcomes the features are intended to deliver.
  • Alignment — Getting internal alignment across a company starts with the senior leadership team. How do they approach setting and reviewing goals, monitoring progress, and managing the product roadmap with the broader organization?

3) How does the team approach product discovery and experimentation?

If this wasn’t covered in earlier conversations, it’s good to ask about these parts explicitly. Figuring out what should be built is one of the hardest and most important aspects of product management, so you’ll be looking for clear and thoughtful answers.

  • Discovery — How does prototyping fit into their process? What other types of user research typically happens prior to writing code? How are engineers involved in this process? You’ll want to see that the product team has put significant thought and effort into managing uncertainty and getting out of the building to learn from their users.
  • Experimentation — Has the company invested in tooling to enable easy experimentation? If so, what are some examples of experiments they are currently running? How often do they launch new features/enhancements that fail? What was their last failure? What did they learn?

4) Where do you want the organization to be in one year from now? How about in five years? What are the biggest product and organizational challenges you’re currently facing?

There’s a lot here, but the goal is to understand if there is a clear vision for the company. Can they speak thoughtfully about where they want to go and what that will look like? Are they willing and able to speak clearly and honestly about the challenges they are facing? Working for an organization that lacks vision can be demoralizing and will often lead to frustration.

5) Tell me about the product, engineering, and design teams. How are they organized? How does the team approach estimation and what does a development cycle look like?

The first part of this question is to help you get a general sense of the size/structure of the various teams and identify if the company is using agencies or external contractors (potentially a red flag). The second part helps you understand how the team executes. There are many different ways to build digital products — are you comfortable and familiar with how they are doing things? Does it sound like an environment you would be happy working in?

6) How do you onboard new employees? How do you set new employees up for success? What are your expectations for the first 90 days?

Having worked at companies where the onboarding was virtually non-existent, I strongly feel this is important to discuss early on. If you’re expected to start making decisions before you’ve had the chance to learn the necessary background and context, you’re likely going to have a tough time. Good product teams make time and put in the effort to onboard new product managers.

7) How will we know if I am doing a good job? What does that look like and how will it be measured? What is your preferred working style with your direct reports? How do you expect to give and receive feedback? How does the product team approach coaching and training?

Being clear on how you will be evaluated and what type of working relationship you can expect to have with your manager is fundamental to your long-term success. Have these conversations candidly and work to understand how your manager views their role in your professional development.


There have been many great minds write about the product job hunt. Here are some of my favorites:

If you like what you read then why not get in touch with me.



Jasper Curry
The Startup

Product at The New York Times. Previously at Noom, Policygenius, and NBC News.