Understanding the recent evolution of head of product roles

In 2023, startups and Big Tech are proving more attractive than growth-stage companies

What does career advice in 2023 look like? Great question – and one that’s weighing on all of us. My podcast has primarily focused on the careers of top performers and project managers, but I think their experiences in many ways are universal and can shed light more broadly. 

There’s no doubt we are on different footing amid the job market pullback, and there are even more nuances to navigate whether you’re considering a startup, a growth company, or something later stage for your next role. In a recent podcast I explored why late-stage companies, which can offer stability and deep learning opportunities, are overshadowing growth and hypergrowth companies as a better value in this volatile time. One of my goals here is to flesh out where startups, which have a perception of being ultra-risky, fit in. 

Beyond just viewing career by stage of company, it’s worth examining how executive roles in product management are evolving and have been impacted by the past year’s market shift. Through the Skip CPO community, which consists of almost 30 heads of product, we’ve seen distinct changes in the job market, the expectations of the role, and the shape of the executive team.

Even if you’re not in product management, or an executive today, this gives you a window into what your boss or boss’s boss might be considering. You might also envision your future self in one of these roles and what you should be thinking about as the market unfolds.

How growth and hypergrowth gave birth to the chief of product role

The head of product role didn’t rise out of thin air. The whole field known as product management has evolved significantly over the past decade, underpinned by a few key developments. “Blitzscaling,” when companies go into hypergrowth mode, is one. It emerged about 10 years ago, after distribution platforms such as Amazon, Google, and Facebook really enabled companies to efficiently find customers.

Between these major distribution platforms and the rise of mobile, startups were able to go from product-market fit to rapid growth overnight. Uber is one really good example. In just about 18 months it achieved a level of growth that took LinkedIn something like 10 years to do. The atmosphere is exciting and the opportunities feel limitless when your product goes from local to global on an exponential basis. In this frenetic environment, all the focus is on expanding and scaling – and finding experts who can make that happen. And as such, the product management function bubbled up as the primary source to enable scale.

I like to look at it this way: You have people who can build stuff, and people who can sell stuff, but you need glue to hold this together. This is where the product manager shines, and proves themself especially essential if a company is in hypergrowth. Not surprisingly, the person leading this function, the CPO – chief product officer – became a critical hire, with many boards and leadership teams increasingly seeking people to install the product management discipline. Essential in this role are skills like being able to prioritize, understanding how to collaborate, and setting goals to truly execute on them. In the past, the CEO and the rest of the executive team had handled much of this lead-up toward product-market fit. (If a company had made it to growth, that team had clearly done a good job!) But to bridge the past success with future gains requires a new person who excelled at being an org builder.

The shift in CPO roles since 2022, and what to seek out now

The pretense of hiring any chief product officer is to expand, scale, and grow. But 2022 slowed growth way down. Sustainability has risen as a priority, forcing the CPO position to be redefined. 

The fact that so many head of product roles are open today seems both strange and logical in a struggling market. Many CPOs are fleeing their roles because, from a growth standpoint, they feel like they’re on a sinking ship. Meanwhile, companies that are tightening their belts and focusing on sustainability are deciding to layer CPOs or lay them off because they think they need a different person (in reality, many heads of product are qualified to retain their roles, just are victims of impatience and panic). Yet candidates are reluctant to join companies that are shifting direction and shrinking. All of this leads to lots of open roles but fewer closed positions.

If you are out there in this market, it’s a confusing time. To make sense of your opportunities, it’s good to break everything down by phase of company – but don’t get hyperfocused on remaining in one stage of company. Be fluid. Moving in and out of phases can be an amazing way to tighten your skills. With each move you get a higher altitude view of how certain processes work and what can be done better or simply differently. Maybe in each transition you also find yourself at different altitudes – as a director, or VP, or senior director. Like viewing artwork from different angles can enrich your understanding, seeing product management from a lot of different perspectives can make you a better career professional.

So let’s examine what you should or shouldn’t be looking for, and what you should avoid or lean into, by stage of company.

Ex-growth companies

I’m on record saying that growth companies that aren’t growing anymore – ex-growth companies – are not where you should be or seek to be, particularly if you’re head of product. Now that the earthquake of 2022 has settled out a bit, these companies are trying to regain or find product-market fit. The founders and CEOs at the helm may have never done this before, so they are steering an ocean liner through Class 4 rapids. Worse, they are unskilled and have a false sense of success because their growth in the past decade stemmed from a market of “free” money and 0% interest. An urgency to regain past glory takes over: layoffs, new strategy, new expectations. 

CPOs are really going to be under the gun in these roles. It’s managing change with a constantly shifting direction, reduced resources, and near unrealistic expectations. And the equity is no longer there to justify the demands and stress involved. There is a reason so many of these roles remain open…

Healthy growth companies

Not all growth companies are bad. There are glints of opportunity. Some companies still have a great upside, haven’t had to step back, and have a good set of expectations. They, of course, are attracting top talent but may have smaller roles to offer. Instead of head of product, you might be working for a CEO who continues to lead product, or a founder who is reluctant to give up the reins. So with that open role, you might end up with ownership of a piece of the product organization, limited to just scaling the core product or acting as general manager for some new product area. If you like the culture, the quality of the business, and the executives in charge, then this gig is worth considering. The learning will be career additive, and the compensation will feel appropriate. And you might be first in line for an eventual head of product role when it materializes.

Even if there is an entrenched CPO in the company, as long as it’s a solid business, you might consider a number two role – especially within the existing climate. There are quite a few stable, later stage companies that offer a ton of benefits as well. No, they might not be in hypergrowth. But they also aren’t drastically stunted from the recent market changes. There’s a chance to develop skills you might not have in the number one position because in a narrower role, you are bound to be more hands-on in your work. Maybe you’re owning a P&L, maybe you’re delivering a product from version 2 to version 3. And all of this feeds into my belief in building toward your next role. You can really focus on skills that might be attractive to a next employer, who is looking for a number one when the market improves.

Big Tech companies

In a recent article, I emphasized the many positives of taking a role in Big Tech, or a late-stage company. It’s harder right now to get in the door, but if you do you’re likely to have strong compensation and consistency. It’s wrong to think you’ll just work there “in the meanwhile,” however. It’ll take two years just to get acclimated, so you should plan to be at one of these companies for at least four years to learn what you need to as well as have a measurable impact. Recognize that you will be asked to hone your “inside the building” skills, managing organizational complexity and building new things within a large number of constraints. Taking advantage of millions (or billions) of customers is really career additive but comes with a lot of strings attached, so be patient and sure that you are up for this type of learning.

Early-stage companies

Okay, you have these later stages of company – but what about considering an even earlier stage company? Imagine a company that only moments ago was a startup. That’s a bit of an exaggeration, but you get the picture. It raised some decent financing and has found its rhythm with recent product-market fit. It has a couple of product managers on staff, but now it’s looking for its first manager for the product management function. You can assume you’ll only have a handful of PMs in your team. It’s not about scaling the team, it’s about scaling the product. They want someone who can work with the CEO and who understands the nuts and bolts of product management, not a strategist. And this isn’t a billion-dollar company (yet or ever) so your expected compensation will be lower and the value of equity is a question mark.

So why would you bother taking on this “early stage” head of product role? In the past, I’ve advised against joining this stage of company. If you are a qualified leader, why not just wait for the company to scale further and join when it’s less risky? Though I still don’t advocate joining pre-PMF startups (you might as well be a founder instead), early-stage companies are a lot more attractive than I believed in the past. As an example, those strong growth companies are few and far between now, so you might be forced to consider early stage to find healthy businesses. And despite the smaller position, it might work in your favor. Even if you are far more senior than your peers, you won’t get layered and you’ll likely enjoy a longer tenure (three or four years versus two). Expectations are realistic, so it’s possible you won’t have to deal with a layoff or shift in direction, making your equity more valuable in the long run. And some of you are motivated by hands-on roles, in which case this might be a great match.

It really comes down to inputs and outputs. If you enjoy diving into the details of building product – working closely with the sales team, engineers, data scientists, and designers on the end user offering – then this is actually a great role that is career additive. Especially true if you’re prepared for slow growth or delays in becoming an org builder. And it’s quite possible that as the market recovers, the company will hit its stride, and then you are trusted and well-placed as it reaches its growth phase.

Startups: Are they worth considering?

Without startups, none of these other phases would even exist. Everything has to start somewhere, right? But does it make sense to take the risk of starting up when the overall environment is pretty iffy? I say yes – as long as you are really passionate about the journey. Some of the best companies have come out of tough environments like we’re experiencing now, when expectations are fairly accurate and a lot of great talent is accessible. You end up building a grittier startup with a greater potential for success. Yet I hear a lot of reservations coming from executives who are nervous about taking this leap of faith, so I want to debunk some of the myths around these objections. 

Objection: Opportunity cost is too high

“Opportunity costs” is the primary objection I hear from executives. If you have reached this point in your career, you are able to generate substantial earnings and are seen as a leader in the workplace. So you are easily qualified to get a terrific job in our industry. Starting up trades an established role for financial risk, as well as uncertainties about growth and impact. Instantly, you are a small fish in a very large pond.

Our current environment is now highly unpredictable, though, so there are risks (whether it’s layoffs, losing scope, project cancellation, or being asked to do too much) no matter which lane you choose. Don’t assume startups hold less certainty than hoping your company or your role remains unscathed. But there is no doubt that creating a job from scratch is quite different from joining a pre-existing company. So if you can’t stomach the opportunity cost of taking an attractive role, you shouldn’t opt for a startup.

Objection: I don’t have an idea

Not many people, if any, just sit, think, and – pow! – have that eureka moment with some amazing idea. However, ideas develop with lots of thinking, conversation, experimentation, and refinement over time.

So when I hear someone say, “I don’t have an idea,” I translate this into, “I am not emotionally excited about the journey of being on my own and starting from scratch.” And if that’s the case, don’t do a startup. But if you do have a passion to start a product from scratch and are just trying to get over that first hump, realize this is your first test.

There are a lot of systems in place to help you. There are incubators. You can network with VCs. Friends oftentimes are asking the same questions – swap advice or team up. Move to a tech hot spot like the Bay Area. Speaking it into the world can generate real luck, and networking can get you to the next level. If you are destined to found a company, start the journey and don’t just wait for that killer idea to come to you in your dreams.

Objection: I don’t have the right team

There’s an old adage: “Can’t never did anything.” And it didn’t. So don’t let “I can’t do this alone” stop you. Right now, with companies having gone through this retrenchment, more people than you realize are in transition. Every successful company has excellent folks looking outward. Maybe you have an idea. Or the passion and willingness to be a partner. Have some conversations. Beyond the idea, a key test of the journey is to attract a team, even if that means co-founders. Hustle your way to find compatible people who are also seeking a team. Maybe they’ll have an idea, and then you’re killing two birds with one stone.

Objection: I worry about burnout

I’m not going to gloss over how much work is involved in a startup. I’ve been a part of four early-stage companies.

But I’m also aware of the work involved in any leadership role at growth and late-stage, or Big Tech, companies. This may sound controversial, but I actually think working in those top positions is more hours than getting a startup going.

In these big companies, there are thousands of employees and a lot of meetings and directions you’re going in. You have to coordinate a broad swath of people and disparate interests across time zones. It’s meetings and more meetings. It’s keeping your boss and your boss’s boss and your boss’s boss’s boss in the loop. Plus board meetings, annual planning, semiannual planning, and quarterly reviews. Granted, these bigger companies are less brittle, and one decision isn’t going to likely make or break them. So on a personal level, yes, startups can be harder – you are involved in every significant decision and have an impact on every employee in some way. But it’s not burnout you should be worried about, it’s the personal obligation of the companies’ success falling on your shoulders.

Objection: Compensation isn’t as high

The last objection I hear is regarding the economics. I get it. You don’t want to build something and have nothing to show for it. You calculate that you could get more reliable and better compensation working at one of the late-stage companies. There’s a lot of truth to this, yes. But if you can go in, work on something meaningful, and hire a really quality team, then even a somewhat unfortunate exit could end well. Other companies will look at the team you’ve built and what you’ve achieved in product-market fit and want to wrap in what you’ve started with what they’re doing. And hiring well is much easier in this environment because there are those folks looking outward and searching for the best growth opportunities.

For my readers who aren’t executives yet, it’s worth pointing out that there’s even less to lose in starting up than when you become an executive. In this case, being a individual contributor for a small part of a company compares poorly to the learning and experience you obtain as a founder, if you have the courage. Careers are long and after the startup, regardless of outcome, you can always transition to a more traditional role.

Ultimately, if you have the passion to start up something new, go for it. Yes, there is risk, but there is some risk everywhere these days. The current economic climate is actually a good one for hiring high-quality people and finding similarly energized folks. Many of you will get your idea past first base and built enough to be sold, with a comp package that looks a lot like what you’d get as a leader at a late-stage or growth company. No matter what, you’ll learn a lot and build your career playbook for the next, next opportunity – which is what the skip is all about.

Conclusion

The landscape has clearly shifted, and whereas a year ago I would have said growth and hypergrowth companies represented the best opportunities, my sense now is that the startup realm is perhaps the most exciting and promising for advancing a career. Two of its potential downsides, risk and lower or delayed compensation, are mitigated by today’s messy environment. It’s just an emotional decision more than an intellectual one - not everyone is mentally ready and excited about starting from scratch.

Next in my stack ranking is a top role at one of the select healthy growth companies, or a number two role at a well-established company where you can dig deep, get predictable compensation, and work for an established leader. On about the same level is Big Tech, if you can find a slot and get in the door.

Following that, I think one of these early-stage companies presents a place to have a lot of impact. You’ll breathe life into the company and get hands-on experience at the same time. For a long time, growth companies seemed to be pulling and pushing forward the rest of the market. But that slice of healthy growth companies has become narrower and narrower, suddenly making the other phases that much more intriguing.

Lucky for you, this means you have plenty of good options, even in an ever-changing and complicated job environment.