When I joined Twiggle as their first VP Product I was the thirteenth employee. Along with the founders (the CEO and CTO), most of the employees in the company at the time were developers. As the VP Product at a startup, I knew I had to work hands-on, and hiring a product manager to take the load off of me would happen only when it became absolutely necessary.

Shortly after I started, the CEO surprised me by saying I should hire a product manager. He had a person in mind who he’d worked with in the past. I wasn’t sure I needed someone back then, but since the CEO requested it, I decided to interview him anyway. He was brilliant and talented, and I ended up hiring him. Initially I gave him only tactical hands-on assignments. He did everything I needed very well, so gradually, I felt very comfortable giving him more and more ownership. Eventually, he managed the entire product from the execution standpoint, while I focused on the strategy and long-term planning. It turned out that hiring him long before I thought I would need him was a great thing. Little did I know that creating a solid product strategy takes such a major chunk of the product leader’s time.  

Since we started early, when I really needed him, we were both ready for our jobs.

Most companies hire a product manager (and other positions) too late. They only start the hiring process when they already need the person. It usually means that the workload is already unbearable. What makes it worse is the long time it takes to hire them: it usually takes three to four months to find the right person, who then needs to give a one-month notice, and then it usually takes an additional month (or up to three, at times) for them to learn and become productive at their work. This process can cause you to chase your tail for over six months. Don’t wait until you are out of breath. You should begin much earlier.

Keep in mind that nowadays, when so much money is invested in tech companies, and top talent is in tremendous demand, finding the right person takes even longer than before.

But starting early is not enough. Once you decide you need to recruit a product manager, who should it be? This is one of the most popular questions I receive from my consulting customers as well as CPO Bootcamp participants. Here are my best tips.

Why Are You Hiring?

The first thing you need to figure out is why you are hiring a product manager. It’s an essential question because it impacts directly who you should hire.

Many founders tell me they are looking for someone to lead the product, but this could be very tricky. They cannot (and should not) let go of defining and designing their product themselves so early. Developing the product has a significant impact on the company’s strategy, and founders must live the market and their customer’s needs in order to define the company’s strategy.

If you do decide to hire a VP Product early on, make sure you set expectations on both sides. They should understand that they will work with you hand in hand and that the job will be very much hands-on, at least at the beginning. This process will help avoid disappointment on both ends. If the person you bring expects to lead the product alone and be hands-off – it might lead to a significant misalignment, which could, in turn, cause them to leave the company and cause you a painful loss of time and money. 

But whether you are a founder or the new VP Product, at some point, you will need to delegate the work to someone else so that you can focus on strategy. Understanding whether you need someone for leading strategy or leading execution makes a great difference, so you should know which of the two you are aiming for.

Who Should You Hire?

Assuming the primary reason you hire the first product manager is to offload the day-to-day hustle of product execution so that you could work more on strategy, there are still many questions to answer. Should you hire a senior product manager? They might want more leeway than you are willing to give. But a junior one might require micro-management and close monitoring until they are fully onboarded and independent, and you cannot necessarily afford that either.

Here are a few guidelines to navigate these questions: 

Senior is generally better than junior, as long as they are willing to do the work since it is challenging and time-consuming to train junior product managers in a startup’s hectic environment. 

I found that two to three years of product management experience should be a great fit, but pay close attention to what kind of experience they have. I have seen people with that experience level that actually led a product from start to finish, while others have just written user stories that were almost dictated to them by someone more senior. Both would appear the same in their CV.

Hire someone who is both capable and willing to do the work. I recently learned from my customers that in the current job market people with 2-3 years of experience expect to be the Head of Product in a young startup. I personally find that insane, since the level of responsibility of the Head of Product in a startup is typically much higher than what someone with 2-3 years of experience can handle well. I realize we can’t fight the trends in the talent market, but it is dangerous. I might write more about that in the future. Whatever you do, don’t create misexpectations, because it will only lead to frustration on both sides.

Understand exactly what you can and want to delegate: You should get into the details of what this job actually looks like. Start by jotting everything you are currently doing and seek out places where you can let someone else handle them. It doesn’t necessarily mean they take full responsibility. You can always stay in charge, but they can still help you in various ways. This mindset shift is essential to finding the right balance and eventually the right person.

I have done this exercise myself recently when I created a job description for my COO (still looking for one, BTW, if you can recommend someone, please send them my way here).

At first, I didn’t think there was much I could let someone else handle, but when it became clear they were here to help me, not replace me, it suddenly became a beautiful full-time job.

A side note for VPs who manage additional roles like design, tech writing, customer success, or product marketing: it is very tempting to hire a Head of Product that will own it fully and reduce your load, but my recommendation is for this to be a last resort. The product management part is so crucial in a startup’s success, that you need to invest more time in it, not less. 

While the execution can be managed by someone else, there are many other ways to solve this: let one of the product managers own the horizontal planning process, embed design and tech writing into teams led by product managers, bring a program manager (it has to be a great one, or else it will do more harm than good), or hire/promote someone as a group product manager, expecting them to execute the entire process and so on. But the strategy should still be on you. 

Letting you have free time to lead the strategy was the whole point of hiring to begin with, remember?

The Compromises You Can and Can’t Make

As you probably experienced, it is an employee’s market out there. Everyone is hiring, tons of money is involved, and great talent is quickly snatched. I know of quite a few CPO Bootcamp alumni whose job search lasted only a few weeks. 

As an employer, this is highly challenging since good people are hard to find. It isn’t easy to persuade them to choose you rather than the competition. It has always been tough to find good product people, but nowadays, they are even rarer.

That could cause you to make compromises in order to make sure you hire someone quickly enough. But not all compromises are worth it. Here is a quick guide to knowing which is which:

• Salary: you can pay as much as your budget allows and be flexible. But also consider that it’s easier to give someone a raise later than to pay a premium for work you are not happy with. Make sure you feel comfortable paying them what they demand and do not feel it’s a mismatch. 
• Experience level: You can hire someone more junior than you intended but highly talented, so you are basically betting on their talent. If you do that, make sure you’re willing and able to help them grow. It takes time, but from my experience, great people are quick learners, so that it could turn into a positive ROI quickly. I have done this in the past, and it was often easy to push them into the deep end and watch them swim. 
• Domain knowledge: You can find someone with excellent specific knowledge relevant to your product. If you need to compromise between a good product person or somebody with great domain knowledge (but poor product skills) – go with the good product manager. Knowledge is more easily obtained than real experience.
• Organizational structure and titles: This is a compromise I recommend making only for the right person. In your search, you might run into great candidates who are even more senior than you need. But they won’t join as “plain” product managers. They will only join you for an executive role and probably demand to report directly to the CEO. If they are outstanding people, and you see a great opportunity, this is a great compromise to make. But if they just want the title and chain of command without relevant experience, this is a major warning sign.
• Cultural fit: The one compromise you should never make at a startup is cultural fit. Do not hire people with a bad attitude or if they are not team players. No matter how talented they are, they could poison your entire company, especially if they are in a senior role. They will not only struggle to make the impact you need from them, but they might also cause others to leave. In a large company, it is painful, but in a startup, it is a death trap.

Like with product goals, hiring the right person also requires understanding exactly why you are doing it and what you hope to achieve. With that in mind, go get the best people you can. 

Good luck!