PF #66: Should you take the job of VP Product @ StartupCo?

Questions to ask before signing up as the head of product at a startup

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You have demonstrated many years of success in Product Management roles at established enterprise businesses. Perhaps you have worked your way to Group PM, Director, or maybe even VP Product within a large bureaucratic enterprise. Now you have the startup itch.

After a number of interesting discussions, then some informal and formal interviews, you are now staring at an offer to join StartupCo.

Awesome! Congratulations!

Wait. What are you getting yourself into? You have bills to pay? What do you know about this company?

First the Backdrop

Joining a startup can be a dream and a nightmare at once. If your professional career never involved a startup, or not in a long time, then you have lots of questions that you should be asking yourself and the company before you take the plunge.

This article is about some of the questions, from my personal experience, that are really significant to ask. The specific emphasis here is on experienced PMs that have an opportunity to join an early stage to growth stage startup as their product leader.

Why do you want to join a startup?

For many that are in large organizations, you may have huge responsibilities already. Your products may be used by hundreds or thousands of customers. You may have a team of people reporting to you and many more directly impacted by your leadership.

Is the desire to go to a startup to learn? Is it to get more responsibility? A VP or CPO title? Is it to get your hands dirty in the trenches working with customers directly again if you are now 3 steps removed from them?

The main thing is to understand why you want to make the move and use that as the context for how you ask questions and analyze all the other data you collect.

Would you invest in this startup?

If you were an investor considering funding this business, would you do it? What kind of questions would you ask.

If you are getting an opportunity to join a startup with 10-50 employees as the head of product, it means that the company has determined they are missing a key leadership position. So they are deciding that filling this is strategic for them to be successful.

On your side, you need to assess if this is worthy of investing your time. Most startups fail. Your compensation will be less generous except for the equity piece. That makes you a potential investor in addition to a key part of the executive team.

You should ask questions about the business model and finances. If they do not want to share this info with you, how can you make an investment decision?

Once you have it, what do you think? Do they have a strong premise? Is the business strategy sound? Where it is lacking do you want to be a part of finding solutions?

Key to me here is the problem they are working to solve. Is it big and have they validated it? Do they understand the assumptions that underpin what they are doing.

Do they set goals and measure progress? Do they minimize the number of plates they are spinning at once?

Remember that a startup is an organization seeking a profitable business model. So do not expect perfection here. Expect a work in progress.

What do you think of the people and culture?

Don’t think for a minute that politics do not exist in a 15 person startup. In fact, they can be more toxic here than in a 3,000 person enterprise and they are unavoidable. So meet with as many of the people you will be working with and assess how they will be to work with.

Are the execs focused on solving the big problems or on who does what? Are titles a big thing to them or do they not even know the official titles of everyone? What kind of communications and meeting culture do they have? Especially, with work from home / remote heavy startups, do they value bringing the team together periodically? How do they talk about one another?

Look for signs of excessive turnover. Turnover can be high in a startup, especially in sales roles or if they leverage contract employees. Yet, when the team is on to something, and incentives are aligned, everyone wants to stay on-board the ship. So a red flag would be significant people leaving on their own.

When meeting with the team, I want to see a group filled with ideas of where the company could go. Lot’s of people asking questions and being curious about how they can do product management better and anything else. Look for team players that are open to discuss their functions and not get defensive or protective when you ask about them.

Startups are about a group of people all doing continuous discovery work to learn. It demands inquisitiveness, open minds, and desire to always improve.

Is there a Product Team?

Most smaller startups you join will have everyone focused on a single product or suite of closely related products. Some larger startups might a a few such teams.

How do they structure product teams? Do they consider engineering and product management to be the same team? Do they have reasonable ratios of design, engineering, product management, and other roles? They probably don’t. It should be part of your job to get them there.

Do they use a lot of external agencies, contractors, or favor getting everyone on-board as an FTE?

What does the software development process look like?

This is critical to understand for a head of product, and you can certainly institute or drive change to better process models — however, knowing the as-is state, is a must starting point.

Key to understanding this is who leads engineering (e.g. CTO, VP Eng) and what is their relationship with you, as the head of product? Some organizations may also have a senior design role, what is their relationship?

When you step in the org, the existing leadership has presumably built some team and processes that they have a vested interest in. How open are they for improving what exists today?

Are there any existing PMs (or POs)? There is a good chance they do not exist and you could be the first product leader coming in from the outside. You will be shaping the teams view on what the head of product should be doing.

Does the team expect some singular expert to assign task work or do they subscribe to the autonomous team concept? Are they flexible on their development methodology or do you have a group of methodology purists? If they are a scrum shop, they may want you to step in immediately playing the PO role. Are you ready for that?

Finally, many times that VP Engineering person, who may also be a co-founder, is going to be an absolutely critical partner to you. You will have tons of product, process, customer issues, and people challenges to solve in the future. Is this someone you think you can work closely and productively with?

What about the Product?

As a product management hire, frequently people dive immediately into the product. Frankly, especially in a startup, the current product you are inheriting does not matter that much. Without a doubt it will be less mature, more debt ridden, and not as sophisticated a solution as you have been told.

This is all fine, your job is not to maintain this existing product but help the company build something far superior at solving valuable problems for 100x the number of existing customers.

By all means, get demos, review the architecture, learn the challenges, get access to customer feedback, etc. Just take this with a grain of salt. It is a starting point only.

Why you?

Are you the first candidate they talked to about this role or the 100th? Why do they thing you are right for the job? Do you see the same thing?

Did anyone have this job before? If not, who in the company handled the responsibilities that will be placed on your lap?

Who will you be reporting to? If it is a startup B2B product company this will tell you the organizational mindset. Are they going after a traditional enterprise sales process or building for product-led growth?

Before signing up, be sure to ask the CEO and your peers what success will look like in 30-60 days and how they think you can help the team achieve that?


If you can handle the risk, take the opportunity.

At the end of the day, there are no right or wrong answers to the questions I laid out above. I have views on what I prefer but you may have different preferences.

The key is that coming into a small startup as the VP Product, will give you every opportunity to help change the answers to the questions above as you see fit. You are coming in not to drive stability to help the organization and product evolve toward great success.

You will be surprised by a great many things when you join any new company. For startups there is usually so little process maturity company to your BigCo job it could be shocking. However, this lack of maturity actually enables much of the responsiveness and innovation that make startups such an enjoyable ride.

Finally, do you take the job?

I covered a number of useful questions you should be exploring. I specifically stayed away from the compensation questions. However, you clearly cannot. Be sure that you are comfortable with the risk-reward opportunity. This is another full topic I may explore later.

With that said, I have two closing comments:

  1. Take as much equity as you can. If you believe in the investment, commit to it. Often you will have some negotiating power around the mix of salary vs. equity. Max the equity piece as long as you can live on the salary component.

  2. If this fails, you became an experienced startup VP Product. There is huge demand for this experience. Whatever you learn will be hugely valuable on the next ride.