Moving from a startup to an enterprise as a product manager

Where a product manager works affects their life, skills, and career. Startups and enterprises, i.e. large IT companies, are at opposite ends of the tech company spectrum, but they do have some things in common. Core product management skills are used in both environments, and both places have motivated, smart, and skilled professionals that want to help their customers. Both settings offer rich experiences that grow talent, however they differ in the types of skills that are most developed. 

A startup teaches product managers how to move fast, tackle new problems, and wear many hats; an enterprise provides a chance to hone the product management craft and learn from successful experts in the field. Enterprises typically move slower than startups by design, and much of the extra time is spent communicating and negotiating with stakeholders. Because of the large user base, the impact of a product manager is usually broader than at a startup.

How do you know if moving from a startup to an enterprise is right for you? We spoke with product managers about their own experiences with making the switch from startup to enterprise. They talked about the pros and cons, what their transition looked like, and what resources they used to help when we asked the following questions:

• Why did you decide to switch from startup to enterprise? Can you describe your path before and how it led to this decision? (#)
• What were your first steps in the transition from startup to enterprise? (#)
• How long did the transition take, from the moment you decided to switch to the moment you got the product management job in enterprise? (#)
• What were the easiest and hardest parts of making the switch? (#)
• Which skills from working on a startup did you find useful in an enterprise product management job? What are the things you had to “unlearn” from your startup job in order to become a better enterprise product management? (#)
• What new, important skills did you gain after the transition? (#)
• What are the pros and cons of transitioning from startup to enterprise? (#)
• You have experience working at a startup and working for a large enterprise. What’s common, what’s different? (#)
• Could you give some advice to someone who has started to think about moving from startup to enterprise? (#)

Thanks to these product managers for their expert advice on transitioning from a product management role in a startup to an enterprise:

• Vinay M. Aradhya (Senior Product Manager at Flutter Entertainment plc)
• Matthew Brightman (Product Manager at Google)
• John McDonald (Senior Product Manager at HEB)
• Debbie Motilewa (Senior Technical Product Manager at AWS)
• Alberto Suárez (Technical Staff Product Manager at Walmart Global Tech)

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Why did you decide to switch from startup to enterprise? Can you describe your path before and how it led to this decision?

Our experts had different reasons for working in the enterprise world. Some of them left the startups they founded, some startups were acquired, and some startups ran out of cash. One of our experts started in nonprofits and academia before even entering the startup and enterprise worlds. But why were the next phases of their careers a jump to enterprise companies?

While each product manager we talked to took a different journey, a common reason they made the switch was to ultimately grow and improve their skill sets. Working in large enterprises changes your focus from a zero-to-one product to a one-to-many product. Enterprises provide the opportunity to develop a data-driven mindset, learn how to manage large organizations, and practice creating a story around your work for a broad audience. Product managers learn to deal with many different stakeholders and an increased scope. The scale of enterprise products and their numbers of customers are larger, forcing a product manager to think through complexities not typically seen at startups. Enterprises typically have less pressures around funding and employee attrition compared to startups as well.

No one path leads to becoming a product manager at an enterprise company. Experiences tend to build on each other. Some product managers progress through a series of startups before they join an enterprise company. For example, they may start at a seed stage company, then move to more established startups, then make the move to enterprise. They may go through different industries, types of products, and organizational structures. Others may get an MBA and work directly for an enterprise company. And just because you work for an enterprise company doesn’t mean you can’t go back to a startup; the enterprise skills you gain will give you a different perspective in startup mode.

Matthew Brightman (Product Manager at Google)

I like to joke that I achieved startup bingo before joining Google; I’ve founded two companies of my own, worked in companies from seed to Series C levels of maturity, and even experienced an acquisition. 

While I’m immensely grateful for my startup experience, I slowly became aware of how it was leaving me with some experience gaps and biases in my decision making. For example, it can be challenging to develop a data-driven mindset when you’re working on zero-to-one type projects with sparse engagement data, or to know what your company’s organization chart should look like if you’ve never been part of one larger than 100 people. 

Ironically, my long-term goal is to be a founder again. It could seem like joining a larger company is a deviation away from that goal, but in reality I feel like it’s gotten me closer. If expertise is just pattern matching, being at a larger company with world class culture and processes has exposed me to a more robust data stream, including skills like managing up or weaving a narrative for your workstream that can be tougher to develop at earlier stage companies but which are still critically important founder skills. 

John McDonald (Senior Product Manager at HEB)

I discovered my passion for product management at WellAware, the startup I helped build prior to joining HEB. At WellAware I ultimately held the position of Head of Product, but found that I still had a hunger to learn from other companies and teams. For most of my time at WellAware there were no other product managers, so I learned about the role through networking, books, and Google, but this was not enough to satisfy my desire to sharpen my skills with other product teams and leaders. I made the decision to join HEB (a massive enterprise here in Texas), as I still had the ability to work with a relatively scrappy “startup-y” team, but within a much larger digital group that I could grow with and learn from.

Debbie Motilewa (Senior Technical Product Manager at AWS)

I’ve had a very unconventional career path. Then again there is really no conventional product management path. I started my career in the nonprofit industry, then moved to startups and then academia (I have a PhD in Corporate Social Responsibility). Then I made a switch to core product management for a multinational corporation. About three years ago, I worked with a group of partners to build a tech startup called Afrohub (think Amazon for Black-owned businesses). Prior to this, all of my startup experiences were dominantly in the service industry and occasionally manufacturing. This was my first time working on a purely tech product that had its revenue coming from platform growth. For two years I loved this experience, it was very different from anything I had ever done before. I worked with developers, monitored online visits, enhanced the sales funnel, improved our website, and drove total engagement. It was amazing. At that point, I knew that my next job would be doing the same thing, but at a larger scale. My current position offers me the opportunity to hone my various product management skills with more flexibility and less worries about funding and employee attrition. 

Alberto Suárez (Technical Staff Product Manager at Walmart Global Tech)

At the end of 2020, we were running out of cash at my startup. Our runway was maybe two months long. This was the first year of the pandemic and it was maybe the worst year of my life. We were having a lot of cash flow issues. Five years before the pandemic started, we signed an agreement with an investor. But after the pandemic they broke their deals and pulled out of the deal and never invested in the company. And after that happened we decided to shut down. I decided to look into the corporate world after maybe eight or nine years of being in the startup world.

Vinay M. Aradhya (Senior Product Manager at Flutter Entertainment plc)

The reasons for switching depends on one’s career goals. Starting from scratch in a startup offers the chance to take a product from 0 to 1, finding a problem, a solution, and a product that fits the market. Enterprise offers the choice of selecting a product and taking it from 1-n. I co-founded a company in the beginning of my career, this helped me a lot in learning the skills needed for product management. 

What were your first steps in the transition from startup to enterprise?

As with any transition, first steps should be focused on gathering information and determining goals. Some professionals may come from backgrounds other than product management. In this case, it’s important to learn about product management practices and key terms through education. This also helps to determine what areas of product management your career should focus on.

Another way to gather information is to interview with a lot of different companies. Interviewing will make you aware of the market value of your skills and any gaps, how different product management teams are structured, and a variety of product management interview strategies. You’ll also uncover what it is you truly want out of your career and what you’re willing to compromise.

And of course there are practicalities that help to determine first steps as well. For example, if a certain location or salary is needed, these factors can help narrow down to only the most fitting jobs and career paths. This isn’t a bad thing; when product managers are aware of their own requirements, the resulting job is a better fit.

Debbie Motilewa (Senior Technical Product Manager at AWS)

I started by reading more about product management. I had been doing the job for years, but under the CEO title. I needed to learn the buzzwords, speak the language, and get buy-in from more experienced business leaders. So my first step was learning. I learned about core product management and specifically product management for enterprises that operated at scale with customers all over the world. 

Matthew Brightman (Product Manager at Google)

I’m fortunate that every one of my startup experiences has been a stepping stone towards the next, and ultimately to my current position. I worked my way up from a seed stage company of my own to a leadership position at a Series A company. This led to a product management role at a more established Series B company which led me to Google. With each role, I was exposed to a different industry, a different team, and a different type of problem to solve, which contributed significantly to my personal growth. 

As such, my transition may not be typical. There are a lot of folks who will join a large enterprise after an MBA, acquisition, or straight out of university. It’s key to remember that there’s no one-size-fits-all path and that you just have to find the one that works for you. 

John McDonald (Senior Product Manager at HEB)

My first step, once I decided I needed to move on, was to talk to a LOT of companies! I probably talked with over thirty companies over the following months before I made my decision, which, while chaotic, was a really good move. Not all of these got to the final round (probably eight or so did), but I took the shotgun approach. Because I had been at the same firm for almost a decade, I really wanted to give myself the chance to learn about what industries, technologies, and problem spaces existed. I learned so much through the experience and made some meaningful professional connections along the way. 

I also got much more competent at the product manager interview. I learned what the market value of my skills were, how different companies structure product management teams, and different philosophies for interviewing and testing product managers. I discovered how other product teams are run, what the common best practices and pitfalls are, and frankly a lot about myself. I figured out what I actually care about in an employer and job, and where I am willing, and not willing, to compromise on these professional desires.

Vinay M. Aradhya (Senior Product Manager at Flutter Entertainment plc)

My first steps were understanding my core strengths and finding the right opportunity. I wanted an opportunity where I could add value and make an impact on the users, customers, and business. 

Alberto Suárez (Technical Staff Product Manager at Walmart Global Tech)

I got offers at the same time from two companies. One company said I would eventually need to move to Virginia. I wanted to stay in the Bay Area and Walmart has some home offices here and the entire Walmart Labs organisation. It was described to me as the only startup inside of a big corporation. That made a lot of sense to me and I decided to join the team.

How long did the transition take, from the moment you decided to switch to the moment you got the product management job in enterprise?

For our experts, making the transition from startup to enterprise took about three to six months. 

Various factors contribute to that timeline. Talking to a lot of companies of course takes time, and waiting until you have the right offer can also lengthen the transition period. Also, in general it takes a bit longer to interview at a large company. There are more stakeholders and rounds to go through and they typically have longer timelines. Other considerations can affect the timeline as well, such as needing to shut down the startup before proceeding or agreeing to a longer transition period so your startup can better prepare for your departure.

Matthew Brightman (Product Manager at Google)

For me, it was less of a conscious decision to switch than a natural transition. Many startup experiences resemble S-Curves: you join, go on a journey of rapid growth and change, and then things taper in one way or another. Sometimes the product doesn’t work out, sometimes there’s a culture misfit, or sometimes you’re just ready for a change. When the opportunity to join Google came around, I was just ready for a new challenge. 

From the moment I interviewed until I joined was probably six months. Partly this is due to the longer time it takes to interview at a bigger company, but also in part because I wasn’t 100% sure I was ready for the change. I decided to stay at my current company for a few months before it became clear that moving to Google was the right step. 

John McDonald (Senior Product Manager at HEB)

I would say it was about three months. Like I mentioned above, I interviewed and networked a lot, but this was by design. I wanted to absorb as much as I could before I made this important decision. This included getting to the offer round with multiple companies and turning all but one of them down.

Debbie Motilewa (Senior Technical Product Manager at AWS)

I want to say I was lucky to have had the easiest and fastest transition. However, I’ll say I made the decision to switch at the right time, I had God’s favour, and everything fell into place easily. I had my first conversation about making the transition with a friend in March 2021 and by June 2021 I got an offer to join the organization I currently work for. So I’ll say three months. 

Alberto Suárez (Technical Staff Product Manager at Walmart Global Tech)

To shut down the company was around five months. The process from end to finish was from July 2021 to December 2021. 

Vinay M. Aradhya (Senior Product Manager at Flutter Entertainment plc)

It was roughly about 3 months of dedicated search and interviews. 

What were the easiest and hardest parts of making the switch?

Because these experts were already working in product management, making the transition to enterprise product management wasn’t that difficult because they already had the general skills. Product management practices are generally the same across the board, and at enterprises the scope could even be more focused than at a startup. Already having product management skills meant it was easier to describe their value to an organization, and an existing product management network made it easier to land interviews. 

However, these product managers had to learn effective communication in the enterprise environment. There are many more teams to collaborate with, stakeholders to convince, and teams to organize. They also needed to get used to their ideas and projects being double-checked and refined rather than having a “move fast and break things” mentality.

The table below shows a summary of what was both easy and hard when making the transition from startup to enterprise.

Vinay M. Aradhya (Senior Product Manager at Flutter Entertainment plc)

The easiest part was discussing what value I can bring to the table. The hardest part was to get a call from the hiring manager or recruiter. 

Matthew Brightman (Product Manager at Google)

People say that product management is different at a bigger company, or that certain bigger companies do product management differently. I didn’t find this to be the case. It was still my job to figure out what the team should focus on, to sell the “why,” and to craft requirements that gave the team the autonomy to figure out the “how.” If anything, product management at a larger company is more focused than at a smaller company, as many of the other hats you might wear as a product manager, e.g. data analyst, UX designer, and scrum master, are absorbed into other bespoke roles fulfilled by one of your teammates. The day job was probably the easiest part of the transition. 

The hardest part for me was learning how to speak enterprise. People in startups love to say that big enterprises are slow, and this is true to some extent, but not because people work any less hard. Whereas a startup might have a “move fast and break things” mentality, larger enterprises are typically concerned with minimizing false positives. Inherently, that means there are more hoops to jump through to make sure you’re not getting it wrong. The result is a kind of slowness, but also a meticulous stress testing and sharpening of your idea to ensure its correctness. For me this was difficult because it meant there were more people to convince, and more forums in which convincing was necessary. At first, it felt like I was in a play where someone forgot to give me the script, but over time I developed a fluency that feels very similar to what an accomplished founder might have when pitching their idea to investors, employees, or advisors. It teaches you to translate your story for the right audience at the right time, and at the end of the day there’s little difference between telling that story at a startup or big enterprise. 

John McDonald (Senior Product Manager at HEB)

At WellAware, I had complete visibility and control over our entire product suite. This meant that there was very little friction from the time I had a hypothesis, to the time I wanted to test, validate, design and build a solution. At HEB, and I would imagine most large tech companies, there are MANY teams that all control a specific sphere of the product or business. This means that the smallest feature could take months of back and forth with dependent product squads and stakeholders until you have the green light to move forward. 

Let me be clear. This is for the most part a very good thing. If HEB was run like WellAware, my Texan neighbors would be lighting my house on fire. It wouldn’t be good. But there is a happy middle ground, and I think I am still learning what I personally believe that middle ground should look like. And for what it’s worth, organizing an enterprise digital product development team is really, really hard. I don’t envy my leaders.

Debbie Motilewa (Senior Technical Product Manager at AWS)

The easiest part of the transition was that I already had the relevant product management experience.The hardest part was the experience was technically in what a developer would call a “different language.” So I needed to speak through my startup experience at interviews in a language that showed I understood the core of product management at enterprises. 

Alberto Suárez (Technical Staff Product Manager at Walmart Global Tech)

The easiest part was that I had some friends working for both companies. So they just put me in contact with the hiring managers. It was more of a network thing. I had the necessary background and I had a network that I constantly nurtured. The hardest part was so many mock interviews.

Which skills from working on a startup did you find useful in an enterprise product management job? What are the things you had to “unlearn” from your startup job in order to become a better enterprise product manager?

Working in a startup teaches valuable skills that can be applied to the enterprise product management experience. Speed and bias for action are two key skills that are incredibly helpful in an enterprise setting. Because enterprise projects typically move more slowly, any time that can be lessened can have a huge impact. Customer empathy is another important skill. In a startup, you can’t rely on an enterprise brand to get customers; you have to solve their problem better than the competition. Product vision, creativity, and intuition are also beneficial skills in enterprises.

Some of our experts felt that they didn’t really need to “unlearn” anything, however others pointed out that building consensus and getting alignment in an enterprise is quite different than in a startup. In a startup a quick conversation can lead to a new feature, but in an enterprise one conversation doesn’t scale. It takes time to discuss with and get agreement from multiple stakeholders before a project can move forward. Another habit to unlearn is the need to constantly wear multiple hats. Enterprise projects are too big to have one person do everything, and if they try they may be actually be taking over someone else’s role. This behavior can lead to bad feelings and damaged relationships if it’s not stopped quickly.

Vinay M. Aradhya (Senior Product Manager at Flutter Entertainment plc)

I believe in one of Amazon’s leadership principles which is “the leaders are right a lot.” Product vision is one of the crucial skills needed along with many others. Creativity and intuition are needed a lot when we don’t have enough data available to make an informed decision. I didn’t have to unlearn anything, but I had to use different skills to optimise the product and features I was responsible for.  

Matthew Brightman (Product Manager at Google)

The speed that I learned at startups became a superpower in my enterprise product management job. Even though there are more processes at a larger enterprise, the scrappiness you learn at a startup can shave days or weeks off your timeline in a big enterprise. While others may wait for a resource to be available, the startup mentality teaches you to just get it done and worry about perfection later. 

The biggest thing I had to unlearn was regarding consensus and alignment. I definitely hit a few roadblocks at first in my enterprise product management career when I thought I had sufficient alignment but in reality I had barely scratched the surface. In a startup, a conversation over lunch can lead to a new feature being launched by dinner to great fanfare, but the same isn’t true in a bigger enterprise. There are simply more people to bring along whose opinions are necessary to sharpen the narrative, ensure alignment, and launch successfully. You might need several reviews, office hours, and one-on-one meetings at an enterprise to do what a quick hallway conversation can accomplish at a startup simply because conversation doesn’t scale linearly with the number of people on a team. 

John McDonald (Senior Product Manager at HEB)

Two startup skills have been particularly useful: bias for action and skepticism. Bias for action simply means pushing to try things, learning, and iterating, as opposed to the more standard enterprise mindset of getting every duck in a row before trying something. Regarding skepticism, it is common at big companies for someone higher up to assign tasks or projects and for the product managers to dutifully nod heads and do the work. Being skeptical means that you ask questions, and seek to understand if the thing you are being told to work on is actually the right thing. It means seeking to understand your customers more deeply, instead of assuming you know them.

If I’m being honest, I haven’t really had to unlearn anything. I’ve certainly had to refine or reframe some expectations and skills since joining HEB, but I would say that for the most part everything has transitioned nicely!

Debbie Motilewa (Senior Technical Product Manager at AWS)

The most important skill I gained from my startup days is customer empathy. In the startup world, your customer is literally everything. You usually don’t have the big name to back you up or make sales. A customer would not say, “I am buying this product because of the brand.” Your product needs to be solving real user problems. The features you build must be very closely tied to the jobs the user is trying to perform. If customers don’t see this clearly, then they’ll most likely not buy or use your product. 

On the other hand, a skill I am actively unlearning is wearing multiple hats. In the startup world, I was the researcher, data scientist, customer representative, marketer, and so many others. While the dream life is to easily drop all these jobs, in reality doing all the roles builds a certain type of trust in one’s ability. I remember I had a researcher working with me on one of my earlier projects in my current job. At the research stage, I did almost every single thing. I coined the research questions, drew up the structure of the research, sourced participants and practically started running the entire research by myself. Luckily, I was able to catch my flaw early in the project. If I hadn’t, I would have severed the working relationship with the researcher. 

What new, important skills did you gain after the transition?

Transitioning to an enterprise product management role expands expertise. Because there are more people working together in an enterprise, product managers get better at building relationships, managing stakeholders, and leading teams. A big part of a product manager’s day in an enterprise is to effectively collaborate and influence a bigger crowd than at a startup. Shared decision-making is common in enterprises, so consensus building is another skill that is gained.

Because of the larger audience, product managers at enterprises gain skills in storytelling and influencing. Product managers need to translate their messages to a variety of stakeholders that all have different backgrounds and goals. Making sure that everyone is up to speed on important initiatives ensures a product manager can influence projects even when not in the room. Empathy for others is something that can also be developed in enterprises because so much time is spent on teamwork rather than moving as fast as possible. 

Deep data analysis is another skill gained from working at enterprises. Most startups, especially in the early stage, don’t have the large amount of data needed to be completely data-driven. At enterprises data is typically readily available. There’s also access tooling to consider. While most startups don’t have access to a variety of data analysis tools, many enterprises make this tooling available to the product managers. Using data to make decisions and set goals can be a game changer in product management.

Vinay M. Aradhya (Senior Product Manager at Flutter Entertainment plc)

In a larger enterprise, building relationships and stakeholder management are crucial. So is leadership. It’s important to lead a product team. 

Matthew Brightman (Product Manager at Google)

The most important skill I’ve learned after transitioning to being an enterprise product manager is better storytelling. At a startup, your storytelling skills have to be sharp, but they can ossify in one way or another. You might give the same pitch to investors or customers one hundred times until it becomes second nature, but it’s essentially the same story. 

In a larger enterprise, you need to translate your story to a myriad of different audiences or stakeholders who all require varying degrees of depth. Learning how to speak to a VP or SVP of a large enterprise is somewhat similar to an elevator pitch in its brevity, but there’s more to it than that. Beyond communicating up, there’s simply just many more stakeholders that need convincing or with whom you have to set proper expectations. 

A director of mine framed this skill nicely when he told me I had to do a better job of influencing the conversation when I wasn’t in the room. At first, this seemed like odd advice and a practically impossible task, until it clicked one day. As an enterprise product manager, you have to juggle alignment with many different parties and keep everyone up to speed on a complex narrative at all times – and that’s not easy! 

John McDonald (Senior Product Manager at HEB)

Really digging into data. I didn’t have access to the depth of data analysis tools at my startup, and this has both been a learning curve and a massive aid in helping me do my job better!

Before I had access to the degree of analytics I have now, my release goals were loose and hard to measure. Now that I have data that can help me answer essentially any question I have, I am able to get very specific about what my goals are for a release and what other guardrails I need to put in place. One of my first major releases at HEB was implementing “contextual add to cart,” meaning if you want to put a banana in your cart, you are first given an option of what quantity of ripe and unripe bananas you want, giving you more control of your shop and mirroring your decision-making when physically in the store. Any change to a critical UI element like an Add to Cart button has the potential to dramatically impact your Metrics that Matter Most (conversion rate, in this case). I set up some analytics reports before and after the release, and was able to measure whether or not the per-item conversion rate was impacted at all, as well as some other guardrail metrics to make sure users weren’t getting confused. It felt amazing to be able to dig in post release and see, with real data, how users were responding, and how the rest of the funnel was impacted. (And I’m happy to report we exceeded our goals with this release!)

Debbie Motilewa (Product Manager II at Microsoft)

Teamwork and collaboration, influencing a bigger crowd, patience (things are not as fast paced as in the startup world), shared decision making (there are more chefs in the kitchen here), experimenting, and generally building a structure around product management that works for me. 

Alberto Suárez (Technical Staff Product Manager at Walmart Global Tech)

I will say that the new skills I gained were patience and working smart but not too hard. I was not as sympathetic as I am now. And I think that living life makes me understand how important it is to be empathetic with others. Being empathetic with others is the secret recipe of life. And I think that when you are a co-founder in that roller coaster life, sometimes you are not. 

What are the pros and cons of transitioning from startup to enterprise?

Enterprises bring particular benefits to product managers. The larger user base means a product manager can have a bigger impact. The product manager is surrounded by many colleagues with a lot of knowledge and experience. The product management practices are usually established and working pretty well. Managers are better trained, the business is more robust, and the work better defined. Product managers are exposed to more people, data, and workstreams, which helps to achieve excellence as there’s more data to show what’s working. Also salary and work life balance is typically, though not always, better than at a startup.

However, there is always another side. Because enterprises typically have large products and features, releases can be slow and time consuming. Product managers are usually working on existing products and maintaining successes, rather than building something new. There can be less freedom and more obstacles. It’s also more difficult to get promoted quickly because the company is later in its growth curve and personnel processes are more defined.

Vinay M. Aradhya (Senior Product Manager at Flutter Entertainment plc)

The pros are a bigger user base that leads to larger user impact, along with colleagues with wealth of knowledge to learn from. The con is that the larger something is sometimes the slower it gets to release. It’s not always the case, but I’ve seen it in some bigger organizations.

Matthew Brightman (Product Manager at Google)

The largest pros of transitioning to enterprise PM is low variance and high exposure to data. Startup experiences can range from awful to amazing and everything in between. While you can get better at spotting the good ones as your career progresses, you may end up learning what not to do just as often as you learn what to do! In one case, I had a friend join a company only to have it announce its bankruptcy the next week. That had to be pretty painful! At a larger company, you’re significantly less likely to have extreme outcomes like these. Managers are better trained, workstreams more well-defined, and teams are more robust to market fluctuations. In parallel, you’re exposed to more people, workstreams, teams, and data, which, in my opinion, allows you to accrue operational excellence faster because you get more data points on what’s working and what’s not. Effectively, your blueprint for building an organization has both more precision and more accuracy. 

The largest con of being an enterprise product manager is linearity. That is, it’s tough to get promoted quickly since processes are better defined and the company may be later in its growth curve. There’s also more internal competition, a higher bar for hiring, and robust processes for promotion, which means that an enterprise may not be for you if your ego revolves around your title or headcount. In my experience, I’ve found folks who optimize for excelling at their craft, solving tough problems, or stability do best in enterprise environments.

John McDonald (Senior Product Manager at HEB)

I would say that so far my experience has been that moving to an enterprise is a great way to quickly absorb best practices and learn from other product managers and product teams. My eight months here have felt like a multi-year crash course, as I have been proactively reaching out, asking questions of others, and seeking this knowledge. It would also be possible to join an enterprise and not treat it this way, and consequently not really learn/grow much at all.

A con is that you will often find yourself maintaining and iterating on existing (and likely successful) digital products, as opposed to building something new, and unproven. Part of the excitement of my startup days was building something truly revolutionary and new like exploring new tech, markets, etc. You might get this experience at an enterprise, but your chances are probably slim.

Alberto Suárez (Technical Staff Product Manager at Walmart Global Tech)

The cons are worries that you have to adapt a lot in terms of the environment and people, less freedom, and more obstacles. People in these kinds of corporations are really territorial. And sometimes they are just pushing back due to anger or ego.

The salary and stability are the pros. Before Walmart I was working Sunday to Sunday. Now I would say that I never receive a text from even my manager or any stakeholders on the weekends. Right now I don’t have any more meetings today and have from 3pm for me.

You have experience working at a startup and working for a large enterprise. What’s common, what’s different? 

At both startups and enterprises there are intelligent and driven product managers that want to do what’s best for their customers. Talented people exist in both environments and most people care deeply about the users. Both environments can also be innovative. Even though an enterprise environment is different from a startup, there are opportunities to become an intrapreneur and create new value for customers in an enterprise.

A big difference between startups and enterprises is that enterprises move slower by design. Product managers must do a lot of communicating and negotiating to accomplish their goals. At a startup, there are rarely established processes and most things are broken or haven’t been created yet. Usually there is no one else that can fix it, so product managers have to tackle a lot on their own. At an enterprise, being aware of people’s roles is key so that a product manager doesn’t cross the line into someone else’s responsibility.

Matthew Brightman (Product Manager at Google)

It can depend on the stage of your career and your goals at any given moment. Some folks employ the earn vs. learn mental model, i.e. you go to startups to learn and the enterprise to earn, but I don’t necessarily agree. Enterprise roles are what you make of them, and you can be an intrapraneur just as much as you can be an entrepreneur. Sometimes it can be even easier to be an intrapraneur because the ingredients, assets, and data you need to innovate are more available in an enterprise environment than a startup environment. 

That being said, I have seen some folks struggle when transitioning to startups after working in enterprise, especially if it’s their first time. At a startup, everything is typically broken or non-existent by default, and there’s rarely a team member in place who can fix it for you. Some people thrive in that environment, and some find it terrifying. 

John McDonald (Senior Product Manager at HEB)

The biggest commonality has been that in both places I have found smart, driven, and customer-oriented product people that deeply desire to positively impact their users. One of the biggest differences is just that things move a lot slower at an enterprise. Again, much of this is deliberate (and good), but you need to get used to doing a lot of talking, cheerleading, convincing, and waiting to get your features across the finish line. At my current professional stage, being a part of a large product team is what I want and need. I’ve gained so much from being here, and the eight months I’ve spent at HEB have already validated my decision to take this job over some very appealing startup offers that I also received.

Could you give some advice to someone who has started to think about moving from startup to enterprise?

The first thing to do is to determine goals and priorities. For example, if the goal is to sharpen product management and communication skills, an enterprise environment is a good choice. If working on new problems and doing a bit of everything are priorities, a startup is probably better. If there’s equity to consider that could be worth something in the future, it may also be a good idea to stay at a startup. 

Once these goals are established and a move to an enterprise is the right direction, decide if there are particular companies or industries of interest and do a lot of research. Connect with product leaders in these areas and be sure to understand the culture because large companies each have distinct cultures. Also in terms of culture, keep in mind that the startup mindset that a product manager is responsible for everything in the company can be destructive at an enterprise. While it’s still good to have passion for the work, there are many things in an enterprise that are outside of a product manager’s control. Learn to let go.

Lastly, if an enterprise product management role doesn’t work out, switching back to a startup is always an option.

Vinay M. Aradhya (Senior Product Manager at Flutter Entertainment plc)

Start by setting a goal, like what industry, company, etc. you are interested in, and identify what skills are required by that company and understand what is lacking. Connect with product leaders for informational interviews to get a clear picture of the role requirement. Join product groups, attend meetups, and network with people to understand how their organisations function. 

Matthew Brightman (Product Manager at Google)

My advice for someone thinking of transitioning from startups to enterprise would be to remember that emotional ownership is different at an enterprise than a startup. As a former founder, I’ve always had the mindset that everything is ultimately my responsibility. The buck stops with me. The CEO does the dishes. I’ve found that can actually be a detrimental mindset at a larger enterprise. While it’s still good to have an appropriate degree of passion and interest in your work, the fact of the matter is there are things outside of your control at a larger company and sometimes it’s best to just let it go. You’re not the founder, and that’s okay. Also, you can always go back to a startup if you don’t like it. 

John McDonald (Senior Product Manager at HEB)

You need to ask yourself what is most important to you, right now, professionally and recognize that you are not locked into any one path. Just because you are at a startup now, doesn’t mean you need to be forever, and vice versa. And going from one to another doesn’t mean you can’t go back at some point!

Are you looking to deepen your learning of the craft of product management? I would argue that in more cases than not, an enterprise is your best bet. Are you looking to learn holistically how a tech company runs, do a bit of everything, and get to work on net-new problems that are still untested or unproven in the market? Do you have a ton of equity at your current company, and think it could be worth something one day? Maybe stay at the startup and keep growing there. Ultimately this is SO nuanced and personal, I find it challenging to provide any blanket guidance, but I am always open on Medium and LinkedIn to connect with others and help you explore your path and options. Best of luck!

Debbie Motilewa (Senior Technical Product Manager at AWS)

If you are thinking about transitioning, I’d say go for it. Get the experience and try a new thing. If you don’t like it, you can always go back to the startup world. Plus you’ll be going back with a larger network and new skills.

Alberto Suárez (Technical Staff Product Manager at Walmart Global Tech)

• Research a lot about the culture of the big corporations because each company has their own culture. In startups, you can just roll out new code. It’s not like that in the big corporations. You need to be really careful what you’re going to roll out because once rolled out it will be really difficult to roll back.
• Being empathetic with others is the secret recipe of life.
• When you have friends, you are never lost. It’s all about human relations.
• You don’t need to be good at everything. You need to recognize your strengths and potentiate them, and be aware of your weaknesses.
• Always listen and before speaking and think about whether it is essential to speak.
• Focus on delivering things and do not allow noise to distract you.
• Keep quiet until you make it because it’s not about who shows up more; it’s about who does more
• Don’t let your ego lead you to make a wrong move, always remember to work smart.
• If one does not know to which port one is sailing, no wind is favourable.
• It is not about who knows the most, it is more about who is willing to learn more.

We’d like to thank Stephanie Walter for incredible help in creating this article.