Your company is on a nice trajectory, and you are in a growth phase. You are bringing in more engineers and designers. The amount of necessary communication increases, and you feel that you need to be in multiple places at the same time. You are jumping between meetings with customers, human resources, ops, and eager engineering and design teams waiting for specifics on the next product.
You need help. You need someone who can execute on your vision and also help validate your assumptions. You need to build a product team around the outcome you want, not the features they are supposed to build. You need to find a sparring partner for product strategy, and you need to create a hub that will provide updates on the status of product development when you need it.
Well, my friend, it sounds like it’s time to bring in your first product manager.
First, determine if you really need a product manager
Finding the right product manager is very important for a startup, so let's dive into the specifics and help you learn what to look out for so that you can bring in the best candidate for the role.
I personally have been an early product hire, and I have brought several products from zero to one. I’ve also helped companies and CEOs establish a business on top of that.
Here is a short checklist that will help you decide — definitively — that you need a product manager:
What experience should the right candidate bring?
If you feel like it’s time to bring in a product manager, you will have several questions and elements to consider.
Let’s go through product levels first. You’ll want to start with the level of experience they have under their belt. Based on the experience you need, you will be able to narrow down your search from the top.
Product managers that are just starting out, all the way up to ~3 years on the job will have mostly focused on specific product initiatives or features. They will be able to drive a bullet point within your roadmap. Analyze what the feature needs, drive development, and measure success once launched.
A senior PM will likely have led a product line or cross-company product initiatives. Or maybe even a product at a smaller company. At this level, a product manager will have 3-6 years of experience. They know how to develop a roadmap for their product. They can work effectively with cross-company stakeholders. And they can own end-to-end features. They become system thinkers. They can talk to customers and distill feature requirements out of their conversations and deliver on them.
The Dream Level: A Principal PM/Head of Product/Director of Product Management
Honestly, as your first product hire, this is the experience level you want. These people should have more than 8 years of experience. They’ve owned product lines and/or business units and worked as head of product. They have developed roadmaps and they’ve had responsibility for a significant business. These are the people that are a perfect fit for a first product hire.
They can take your plan for the company and run with it. They will be able to tell you how many people they need to be able to execute against your roadmap. They can do yearly and quarterly planning, get all stakeholders on the same page, and drive the ship while you handle CEO tasks.
You don’t need to go beyond that level of experience. High-level folks are not usually hands-on product management. If they’ve been a VP with 8-10 direct reports and your company is not growing that fast, they may not be as hands-on as required for your immediate needs.
What product manager characteristics do I need to look for?
Now that we’ve established that you want a hands-on, execution-oriented person with ~6-8+ years of experience, let's look at some more industry specifics.
The role of a product manager is a central one. You can expect a product manager to be in the middle of engineering, design, marketing, sales, customer support, ops, and whatever other product related company departments you have. If you are the CEO of a company and you’re reading this, you’re likely thinking, “That sounds like my role.” To be sure, there might be some overlap between PMs and founders. But the product manager will have a few fewer things to worry about, which allows them to focus on one thing: the product.
General characteristics that translate to success
There are five general characteristics that I would recommend focusing on: communication, passion and energy, quick thinking, empathy, and humility. Several of these characteristics are self-explanatory. But you might wonder, Why humility? Product management, working with a team of smart people with strong opinions, requires an open mind. A good product manager wants to give everyone on the team a voice, and should be open to suggestions and differing opinions. They should also be open to learning. They also tend to constantly self-assess their skills and behavior. The combination of someone with these characteristics, an open mind and the drive to take extreme ownership will make them an unstoppable PM.
Product managers tend to fall into two categories. I have interviewed around 50-60 product people for startups, from junior to head of product roles. This section will help you select the right candidate for your startup.
Product manager type 1: The product visionary and strategist
This is the person that helps you develop a vision. They pull in customers, teams, stakeholders, and salespeople. They want to dive deep.
They run ideation sessions, get the team fired up, and are motivated to develop concepts and ideas. They distill information and keep thinking about it. They will be able to set up learnings into a strategy and vision. They know what the market needs and how your company can get there. And they know what the path of the company should be.
They will be able to set up a roadmap for the next 12 months, and a higher level roadmap for the next 2-5 years. They think big. They zoom out. They can drive that process.
They also pitch it to the team, get them excited and keep them motivated. They find the north star and constantly remind the company where they need to go.
You need to decide if you find yourself in that position. If you are a visionary type of leader, you might not need to hire someone to develop a vision. If you are the founder of the company, you should have a plan for your strategy, and a PM of this type won’t bring the value you are looking for. When you already have a vision and a strategy, it’s a matter of getting there.
Product manager type 2: The product operator and executor
This is the type of person who gets stuff done. In the right scenario, you have a roadmap and you wish someone could tell you how many engineers, designers, and other folks you need to achieve all the milestones on time.
You know where the company needs to be in five years. But you want to know if your customers want your company to be there. And you need to know what they need along the way to get the company to the five-year mark. Most of all, you need your product to develop to this point.
You need someone who can take your roadmap, tell you what they need to deliver, and build a well-oiled product development machine and deliver all your features and milestones.
They will plan quarters, and set deliverables per quarter. They will set up sprints, go to sprint plannings, and make sure all engineers are unblocked. They will follow up on customer needs. They have a prioritized list of things that need to be done in a ranked order. And they make sure the teams deliver on agreed deliverables. They will write epics and stories, and follow through with design and engineering until the feature is DONE and released.
I know that ideally, you want both options in one person. Someone who can be a sparring partner in helping on the vision and strategy. But let’s be honest, if you hire someone that develops a different 5-year vision than you have, they better bring damn good data to convince you. And even then, you might know better.
Again, a head of product should be able to develop a product strategy and deliver on it. But they will be stronger on one of the two. Whichever one you need, they will be a valuable asset.
Hire the right type of PM at the right time
PM Leader Jonathan Golden from Airbnb categorizes PMs in buckets of pioneers, settlers, and town planners. The role depends on different phases of company development. I like that analogy.
Pioneers
Pioneers get excited about the new, the unknown. They see the risk but also big rewards if an endeavor works out. They have characteristics similar to founders. If you are very early and need to prove out a lot of your assumptions, this is a good hire to look for.
Settlers
Settlers care about scaling and growing a product that has found a place in the market. The product hypotheses have checked out, and now it's time to grow, grow, grow. They will operate with a focus on metrics and growth milestones. They love to look at analytics dashboards and evaluate every knob they turn to see if they result in growth.
Town Planners
Your product is hitting scale. Your engineering team tells you if you bring on more customers, you will hit new scale ceilings, and the platform has to be built out. And this is when it’s time to bring in town planners to accommodate your needs. They have a bit more technical background and have worked on scale products before. These PMs will focus on overall infrastructure and will be able to spot non-scalable systems across your product, like technical tools, backend architecture, customer support systems, etc.
You can read more on this topic in First Round Review.
Specifics for your company and industry
You likely won’t find a perfect fit — someone who has the same exact industry and product experience. But it might be worth checking out competitors' product folks on LinkedIn, and asking if they’d like to chat.
The following are some things they should have experience with:
If you are a B2C or B2B company, you should find someone who has experience in that field. There are big differences in selling, talking to customers, release cycles and release preparation, and this is good base knowledge to bring. This is not as important in more junior roles, but it is super important for your head of product. You want them to be familiar with the way customer relations work and how your sales team works.
If you’re building a SaaS product, for example, find someone who has done that. If you want to build hardware as part of it, that’s good experience to bring to the table. Building end-to- end systems involving hardware is very different from just focusing on software. You want this experience in your head of product.
Lastly, you are probably building a completely new product or a set of new products. Going from zero to one is a very valuable set of skills. If you find someone that has done this, it will be great. Look for those Pioneer and Settler qualities from the section above.
Taking industry specifics into consideration, this is where you can make tradeoffs. And that doesn’t have to be a bad thing. Some industries have developed very high-tech, very user-friendly products. Maybe look into those, if that’s not the case in your industry.
Great product managers will be able to understand and dive into your industry quickly, and understand the ins and outs by doing market research and talking to your customers. This opens up the field of candidates and can lead to some very interesting conversations with the people you are looking to bring in.
What would the team structure and ratio between Product, Engineering, and Design look like?
For a full product with frontend and backend, you would assume a ratio of 1 PM to 1 designer and 8 engineers. It depends on the type of product. More technical products with barely any UI will have more engineers, up to 12 per PM, and very little design involvement. You can then add a technical writer to that team — especially if you are building out APIs for external developers.
Where to look for the right candidate
LinkedIn is a great tool to get an idea of people who might be available. LinkedIn’s tool “Recruiter” will help you in a big way. It lets you define your keywords and search for candidates. You can even filter by “Open to work.”
LinkedIn has built a fantastic tool. You can save candidates and even provide multiple people access to your pipeline, screen them, and reach out to those candidates. You can also track replies, etc. LinkedIn makes looking for talent easy. It takes some time, but it will help you refine the skillset you are looking for.
If you are looking to get involved more deeply in product communities, there are some fantastic ones available to you. Just to list a few here: Mind the Product, Women in Product, and Product Manager groups on Facebook and LinkedIn.
How to interview a product manager
Your pipeline is growing, and you are seeing some interesting candidates who want to talk. The most important thing is getting a strong sense you can get along well with your potential hire. If you gel, great! You will have a lot of long conversations and sometimes difficult decisions to make, and you want to be sure that you can develop trust in the person you choose.
The candidate needs to be an excellent communicator. What writing code is for engineers and design is for designers, communication is for product managers. Good indicators for caution are if you struggle to get in a good question-answer flow with them, or they give long-winded answers that go from one story to the next and you’re not sure how to best politely interrupt.
They need to be able to sell the company vision and strategy to engineers, designers, and customers. They need a good level of energy. That is hard to measure, but if you feel they don’t come across energized and motivated, they won’t get anyone on the team excited. Bruce Springsteen knows You can’t start a fire without a spark.
For specific skills, pick some questions that dive into situations that you want to analyze. For example:
How organized are they?
How do they collaborate with others?
How do they give everyone on the team a voice?
How do they influence decisions while making everyone feel heard?
How do they guarantee on-time delivery of features?
How do they talk to customers?
Ask them open-ended behavioral questions that aim for info on these skills and frameworks.
The hiring loop
You will need to screen candidates in initial conversations. Once you feel good about a candidate, bring them in for a full round. They should meet all your key leaders and people they will work with. (Not every engineer, but at least the engineering manager or lead). A product manager is such a critical hire (especially in a smaller company) that you want to make sure they get along with everyone. When I interviewed at a 35-person startup that was just raising Series B, I interviewed with 8 people. It took several days. This is very common, and PMs will accept that. They also want to make sure they get along with everyone!
As the last step, you can consider also bringing in a product-focused board member for this important hire. You want the board to trust your first product hire. Consider how you want this product person to meet them. Again, this should be one of the last stages of your interview. You don’t want to ask your board members to weed out the bulk of people.
It really is all about the right fit
The first project manager hire is an important one. Don’t see it as just bringing in someone to help make timelines and build features for you. Find a partner that can drive the product strategy, keep the team on track, and emphasize your customers.
BONUS - A targeted list of interview questions you can ask
Here are a few good questions targeting the areas discussed above:
Would you rather formulate a plan or carry it out? Why? Give me an example of a plan you have implemented.
This is the question that separates the “doers” from the “planners.” Give the person a task, and find out what they would do to make it happen. These people are highly detail-oriented. How will they follow through and help you achieve your goals?
While strategists show the way and the resources needed, they are less likely to execute hands-on.
Some people are “doers” — they like to be given a task to do, and they’ll make it happen. They too are often detail-oriented. Few people can succeed at both planning and executing the plan. For candidates who tell you they like to control both planning and execution, get specific examples of how they have gone about it. It will be good to explore if they draw help from others and know to delegate, to monitor results, and drive the overall process. If they are managing a team, you should learn about their management ability in this context.
Do you like to juggle a lot of activities at once or do them one at a time?
This is a crucial skill. It comes right after communication. A day in the life of a PM is filled with focus work sessions to write PRDs, and meetings in between. Plus, there’s constant context switching. Find how the candidate thinks about this. People who juggle a lot of tasks at once usually like variety and diversity. However, this sort of candidate may also tackle too many projects to get them all completed, and may be easily interrupted. Dig deeper to find out what keeps them focused when needed.
Describe a way you have improved the organization of a system or task at your last/present job?
Candidates that have that “zero to one” background or have been in fast-growing startups have no doubt faced this situation. They will constantly see systems that need improvement for bigger teams, longer backlogs, and more need for communication.
Applicants who are well-organized and have frameworks in place often look for ways to improve upon old procedures and systems. If this is the case, he/she will volunteer examples quickly.
If we hired you, what could we count on you for without fail?
Listen carefully to what the applicant speaks clearly and confidently about. You want to find out about the candidate's self-awareness and dependability, and delve into details. For example, if they tell you they “do their best work every day,” then follow up and ask for an example of that. You are looking for a concrete example that they are confident about sharing.
Tell me about a situation where you had to convince someone on your team and resolve a conflict.
Product managers don’t have authority. But they need to be a leader who people want to follow and trust. A product manager needs to gain the trust of their team. You want to hear how they’ve dealt with conflicts about priorities. How did they convince others, and what was the outcome? Make sure they also talk about how they collaboratively solved conflicts. The goal is to give everyone on the team a voice. Every experienced product manager should have lots of examples to talk about here.
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