Startups vs. Enterprises: Project Management Evolution

Things are different for startups; they play poker, not chess.

Don Dodge, a Google Developer Advocate, has drawn attention to the differences between being a project manager in a startup environment and a larger enterprise. Through his experience, Don has identified key distinctions that can have an impact on the success of a project.

Starting up a business can be likened to playing a game of chance, much like a poker game. Typically, the most experienced players are successful, though it is not uncommon for a novice to beat them. For startups, successful project management requires excellent execution, but even the most capable entrepreneurs may not be successful. To avoid such outcomes, an enterprise project management system should be implemented with a more strategic approach, allowing for two steps of planning ahead and limiting risks.

Everything Is Not Black And White

Prior to beginning, it is essential to understand that there is a wide variety of business models. Could a company with one hundred employees still be considered a startup? What if the size of the business increases to two or three hundred? Although Uber currently has twelve thousand employees, it is still commonly referred to as a startup. Additionally, the dynamics of a business created by undergraduates are drastically different to those of a business started by entrepreneurs who possess over twenty years of professional experience, and have had the opportunity to transfer their learned knowledge from corporate environments back into their own businesses.

As a consequence, there are many illustrations of different business environments, from a small startup with five employees working in the same location to a multinational corporation having offices in various countries across the world. While this article will primarily focus on these two extremes, it is important to remember that all information should be taken with a pinch of salt and carefully evaluated to determine if it is applicable to your specific circumstances.

Enterprises vs. Startups

Now that we have established our starting point, let us attempt to define the two extremes to provide the foundation for our discussion. For the purposes of this article, the following characteristics can be used to define a startup:

  • A team of up to fifty members located in the same physical workspace, allowing for the development of personal relationships and familiarity among coworkers. This allows team members to get to know each other on a personal level, creating an environment of trust and collaboration.
  • There are no clear roles.
  • The founders decide most of the alternatives.
  • The company is suffering financially and has little margin for growth – staying alive is a huge concern.

On the other end of the spectrum, a business may look like the diagram below:

  • There are several departments and offices.
  • You only know your immediate coworkers and chat with people from other departments occasionally.
  • Every person plays a unique role and occupies a particular position.
  • The firm may go public.
  • There are no issues of profitability or short-term survival here.

Handling startup projects

A person responsible for a project’s success or failure

In principle, the responsibilities of project managers and product managers are markedly different. Nevertheless, in a startup environment, the two roles tend to overlap. If you work as a project manager at a startup, you can anticipate that you will be asked to assume responsibilities beyond those normally expected within a more established enterprise.

Project Managers Can Benefit From startups

Impactive Material Decisions

Making key decisions in the project management of a startup can be straightforward due to the limited number of dependencies, such as protocols, other departments, and customers. A project manager can easily hire a new colleague, alter the website, include new features, or extend a deadline with a single gathering or Slack message. This provides the project manager with a sense of authority and independence.

Starting a new business is an ideal way to put your ideas into practice and progress in your career. For example, you could try out a project management tool proposed by a colleague of yours who has experience with it. You could also consider changing from Scrum to Kanban to speed up the delivery process, which your CEO seems to be in favour of. Moreover, your CTO believes that you do not need a programmer to implement the new chatbot that allows you to search for data in Google Analytics using natural language. All of these tasks would require a lot of effort, and should be managed by an experienced project manager in a professional environment.


Due to the shortened development life cycle of startups, it is possible to go from brainstorming to having a product in production in as little as one week. This advantage is heightened by the lack of legacy code, which often results in developers having to spend considerable time reworking the codebase. Consequently, startups are able to rapidly produce results while also providing a continual feedback loop with customers. This enables startups to remain agile and adaptive.


As a testament to the power of agility in a startup environment, the well-known example of PayPal is often cited. In the first 15 months after its inception as a “cryptography for phones” solution, PayPal changed its direction a remarkable five times in order to stay competitive in the rapidly-evolving payments ecosystem. This agility allowed PayPal to gain traction amongst eBay’s customers and merchants, leading to the eventual acquisition of PayPal by eBay. This serves as a powerful example of the advantages of being able to pivot quickly without the burden of dependencies.


In general, most businesses do not have rigid protocols and processes in place to dictate how employees work. This leaves much to common sense and internal dialogue. This is why the ideas discussed previously are effective, as decisions can be made quickly without the need for multiple approvals. However, this can lead to further complications in the future. Despite this, it may be a viable compromise for a company that is trying to gain an advantage over competitors with more financial resources and a greater size.

Startups Are Hard On Project Managers

The Responsibilities Are Not Completely Described

A fluid approach to decision-making can be beneficial in providing quick, accurate judgments. However, when things do not go as planned, it can lead to mistakes and a disorganised work environment. Therefore, having a process in place can be highly advantageous. A process can be understood as a set of detailed instructions outlining the necessary steps to be taken in order to achieve a specific goal. These processes are often created in response to a failure, when colleagues start to assign blame and a company is prompted to create a process to ensure that decisions are made in an organised and efficient manner, thus reducing the likelihood of such issues from occurring in the future.

As a result of a website crash caused by the implementation of a new version, a discussion ensued among the relevant parties to determine who should have taken responsibility for informing the customer of the forthcoming release. It was agreed that in the future, certain personnel would be held accountable for specific activities prior to any releases to ensure that similar issues are prevented. The project manager and key account manager were identified as having a responsibility to contact the development team of the client and the CTO was identified as needing to take a more assertive approach.

As a fledgling startup grows and develops, it is inevitable that certain decisions will have to be taken in order to ensure that the organisation can manage the increasing complexity that comes with success. This helps to minimise the amount of uncertainty within the organisation’s day-to-day operations. However, it is also probable that a number of mistakes and errors will be made along the way as the company transitions from a startup to a fully-fledged enterprise.


As a Startup Project Manager, it is common for you to be involved in external conversations. During such conversations, it is important to be mindful of the potential for new needs and requests to emerge. Co-founders may attend customer meetings in the later stages of the presentation to convey the technical and product aspects of the offering. While they may be eager to win the customer over, it is important to be aware that the customer may attempt to leverage the lack of a lengthy track record to get the company to commit to something that is not realistic or feasible. As such, it is essential to exercise caution and not agree to deliverables too hastily.

As a project manager, it is essential to be able to advocate for the team’s needs and request additional time for the development team to assess any new requirements. Once you have obtained estimates from the team, it is important to bring these to the co-founders and discuss whether the revised contract terms are still suitable.


As a project manager, it can be tempting to succumb to the pressure of co-founders and seek shortcuts in order to meet tight timelines for roadmap items. However, this is not without its risks. With great power comes great responsibility, and if you do not exercise caution in this regard, your team may end up dealing with legacy issues even in the early stages of the startup. Taking an approach that is mindful of the risks and long-term implications is essential to maintaining a perpetual MVP phase.

Our firm has decided to construct a product listing page that includes a variety of philtres and sorting options. Upon further investigation, it is apparent that the majority of the estimated work is related to the search and presentation of the results. To expedite the process, we inquire if it is possible to provide a more basic version of the page sooner. One of the developers suggests utilising a third-party solution that requires a monthly subscription fee. The other developers discuss the implications of this and the potential for legacy issues. This option appears to be the most suitable given that we can receive a Minimum Viable Product (MVP) sooner and the subscription can be cancelled if we choose to discontinue the project. The Scrum Master agrees to this solution, provided that they are given the ability to rework the code should the project not be cancelled.

Despite the commitment to prioritise technical debt work, this is often not adhered to, unless the Scrum Master makes a conscious effort to include it in a later sprint and can explain why it should be prioritised. If the initial response to the listing page is positive, the Project Manager may be tempted to add additional features, beyond what was originally planned as part of the Minimum Viable Product (MVP). However, after six months, it may become too costly to add new features, or to restructure the existing ones. Furthermore, other objectives may take priority and overshadow the original purpose of the project.


In the field of Information Technology project management, a false positive can arise when a team develops and implements a Minimum Viable Product (MVP) and receives positive initial feedback, incorrectly interpreting it as evidence of a successful product-market fit. This phenomenon can even manifest itself earlier in the process when stakeholders indicate that they have presented the solution to the largest customer in the industry and been told the customer would definitely purchase it. Despite this perceived assurance, the customer may ultimately not purchase the product.

False positives can be a major impediment for organisations, but there is a method for minimising their occurrence. According to Steve Cohn, the Founder of Validately, validating market demand for one’s product or service is essential in order to reduce false positives. Mr. Cohn has identified three possible indicators that may be useful in this pursuit:

  • Do your customers demonstrate a willingness to invest or commit financially prior to you providing them with the full solution? Obtaining a contract prior to delivering the solution is likely the most reliable form of validation that you can receive.
  • Do your customers show enthusiasm for working with you to create a solution? Time is a precious resource, and everyone has an ever-growing list of tasks to complete. If a customer is actively engaged in the process, including involving their colleagues in the conversation, conducting thorough testing of a minimum viable product and providing feedback, then you are more likely to be on the right track.
  • Are your customers ready to leverage their good reputation to promote your business? When customers advocate for your business, whether it be through social media, at a professional gathering, or any other platform, they are demonstrating their genuine commitment by extending the reputation they have built for themselves.


As a project manager, the involvement of co-founders is often of paramount importance. As demonstrated in the possibilities section, co-founders can expedite decisions by exercising their sound judgement. However, it is not uncommon for co-founders to rely on their intuition when making decisions. This is particularly the case for those who have vast experience in the subject matter and are now developing a technology-based solution to solve a challenge they have faced in their professional journeys.

Having access to comprehensive market information can be of great benefit to any organisation. However, it is important to note that relying solely on this data when creating a business strategy can be risky. Many entrepreneurs desire to create a solution that can be applied on a global level. Even if the same market contains numerous organisations, they may not all address the same challenges in the same way. The co-founder may have an in-depth understanding of the methods utilised by their former company, but this does not guarantee complete knowledge of how other firms, particularly those in different countries, have handled comparable issues.

As co-founders often have strong convictions about their product, it is essential for a project manager to be involved in the early phases of product discovery. In this capacity, the project manager is responsible for providing a balanced perspective between the co-founders, while also educating them on the importance of making decisions based on data and utilising agile development principles. This helps to ensure that any product being developed is built on a solid foundation and is well-equipped to meet the needs of consumers.

Enterprise Project Management

The Project Manager is not the same as the Product Manager

As a business progresses and expands, the roles and responsibilities of various positions become more clear-cut and detailed. Even within a large corporation, there can be overlap between the jobs of a project manager and a product manager. The project manager would be primarily responsible for the operational elements of a project, while the product manager is responsible for putting the project into action.

The PMO is a section of an organisation charged with the oversight of all project management activities

As the company grows and its project portfolio expands, it is necessary to create a Project Management Office (PMO). This office is tasked with overseeing the entire project management lifecycle, and has the capability to implement and ensure the use of the most effective processes and techniques across the organisation. The establishment of a PMO is especially important when the organisation is welcoming new project managers who bring with them their own set of project management tools and approaches. This can often lead to a period of disorganisation and confusion, so the PMO helps to ensure the organisation maintains a smooth, efficient workflow.

As an enterprise project manager, it is essential to interact with the Project Management Office (PMO). The PMO will be varied and distinct in nature, and you may face a variety of challenges while interacting with it. These issues could include difficulty in obtaining resources, inadequate communication with stakeholders, lack of necessary funds, or the need to make difficult decisions to ensure the success of the project. It is important to be mindful of these potential issues and develop strategies to efficiently navigate them.

  • Participating in multiple forms for project start-up and completion.
  • An evaluation budget has been submitted.
  • Providing frequent status updates
  • Approving process steps or milestones.

Many project managers may find that the criteria set by the Project Management Office (PMO) is an extra layer of bureaucracy that can be frustrating and slow down the project. However, with a proactive attitude, project managers can minimise the time and resources spent on meeting the PMO criteria, and can even use the PMO to their advantage.

  • It is important to involve the Project Management Office (PMO) as early as possible in the process of establishing the reporting needs. Doing so can help to save time, as the reporting requirements can be tailored to the materials that were created during the project’s execution.
  • As a champion of the project process, it is essential to provide comments to the Project Management Office (PMO) on how procedures can be improved to make project managers’ lives easier. One of the primary goals of the PMO is to help project managers become successful and efficient in their roles. Therefore, it is important to provide feedback on how the existing procedures can be altered to facilitate their growth and development. Such changes may involve streamlining processes, creating more efficient tools, and providing better training and support.
  • If you encounter any issues with your project, you can always rely on the Project Management Office (PMO) for assistance. The PMO has a comprehensive understanding of all projects taking place within the company and is well-equipped to handle any difficulties or obstacles that may arise during the project’s execution. Utilising their expertise can be a great advantage to you and your project.

Project Managers have openings in enterprise


Establishing and maintaining enterprise stability through long-term planning conveys a strong message of reliability and trustworthiness to customers and partners. Organisations that are looking to collaborate with your business want to be assured of your reliable track record, your potential to fulfill commitments, and your expertise in the industry. This is one of the most significant advantages that a well-established company has over new businesses, as it encourages the acquisition of new customers and partners.

You can trust this organisation to help you become more closely connected with the customer. As a technology provider, you can provide your customers with the ability to keep up with the latest features as quickly as possible by adapting their own development plans to coincide with yours. Establishing such a relationship can be a challenge for a startup, as startups tend to be unpredictable and hard to rely on.

Collection Is Easier For Requirements

In comparison to a startup, a business that is established and has been running for some time has a significantly larger presence in the market. As the company expands and the tasks it needs to complete become more specialised, it needs to bring in more experienced and skilled professionals. At the same time, the organisation will also attract more experienced and high-level executives in order to ensure that the company’s vision and goals remain unchanged. All of these individuals will be able to contribute valuable market insights, which a project manager can access and use to gather user requirements.

Project Managers (PMs) can benefit greatly from having a wide network of connections that they can leverage to their advantage. Having access to multiple contacts within the organisation can help PMs to effectively influence other stakeholders and ensure that their project receives the necessary attention from senior management. Furthermore, building a strong network of contacts can be beneficial for personal growth, as it provides PMs with the opportunity to develop their communication and relationship building skills.

The sales, account management and customer support teams can be invaluable resources when it comes to understanding user needs. These teams are frequently in contact with customers, providing them with an array of information regarding user requirements and complaints. However, it is important to take into account the context of the feedback being provided. For example, the client support staff interacts with individuals who use the product, while sales and account managers may be engaging with high-level executives who make purchasing decisions but may not actually use the program.


Mergers and acquisitions (M&A) present a unique opportunity for startups that other growth strategies cannot provide. In 2018, global M&A activity has already hit a record high, with major deals such as AT&T’s $85 billion purchase of Time Warner. However, Harvard Business Review research suggests that smaller acquisitions, which are often of lower value, can be significantly more profitable. Corporate project managers should consider the potential benefits of acquiring smaller businesses with single-point solutions, instead of attempting to recreate them. Although project managers may not be in a position to make the final decision, they can present this option to the decision makers.

Enterprise Project Managers Encounter Problems


As the business grows, its reporting system will become increasingly complex. Different divisions, methods, and procedures will be implemented to meet the needs of the organisation. Additionally, brand guidelines will be formulated to ensure a consistent brand identity and recognition. It is also essential to take into account any legal considerations that may arise in the course of business operations. Acquiring all the necessary sign-offs for a joint press release with a new partner may take several weeks, so it is important to factor this time into the planning process.

A project manager must be proactive and stay prepared for any project-related challenges that may arise. It is essential for them to stay ahead of the game in order to be successful. Despite this, there are always unpredictable events which require the project manager to acquire clearance as soon as possible. Developing strong relationships with other departments can be of great help in such cases, as a project manager who is willing to lend a helping hand is more likely to receive favours from their peers.


As a project manager, it is important to remember that one should never take anything for granted. As the complexity of a company increases, the responsibilities of the project manager become increasingly more difficult, especially in terms of ensuring effective communication between members of the project team and external entities. To illustrate this point, let us consider a hypothetical situation.

At lunch, our team encountered the Design Team Leader and informed them of the need for a few new icons for the new features being developed. The Design Team Leader claimed they were already working on similar icons and would have them available soon. The next day, at the stand-up, this information was relayed to the team, and they were instructed to contact the Design Team if they needed the icons. With the features expected to be ready in four weeks, everyone assumed the icons would be available at that time. Developers inserted placeholders for the icons, and it was only during Quality Assurance that it was noticed the icons had not been replaced. Our team hurried to contact the Design Team, who had been delayed in producing the symbols due to other pressing matters. Unfortunately, no one from our team had contacted the Design Team and they assumed the icons were no longer needed. Brand rules prohibit us from going to production with any arbitrary icons, leaving our team with developed features but unable to release them.

As a project manager, there are countless opportunities to misunderstand the role you play in a company. To ensure success in this position, it is important to take the proper steps to prevent miscommunication, such as establishing two distinct approaches to the job. Specifically, these approaches can include maintaining a clear understanding of the company’s goals, as well as staying in constant communication with all stakeholders involved in the project. By doing so, project managers can ensure that their duties are fulfilled to the best of their ability, and that any potential misunderstanding is mitigated.

  • At the retrospective, it is important to collaboratively assess with the team if a different approach could help to prevent similar mistakes from occurring in the future. As a potential solution, the team could consider creating a list of all external dependencies, and then performing weekly reviews and follow-ups to ensure that the deliverables are being met in a timely manner.
  • Regular and frequent communication is a key component of successful project management. It is wise to communicate more than you feel is necessary, and to make a habit of checking in with colleagues and asking for brief updates. This will help to ensure that nothing slips through the cracks.

Move Carefully And At A Slower Pace. Nothing Should Be Broken

As a project manager, you may come to realise that the older the codebase is, the more challenging it becomes to introduce new features. This can be particularly worrying as you observe that smaller businesses are utilising cutting-edge technology to bring new products and services to market with greater speed and efficiency, thus out-competing your own organisation.

As corporations strive to defend themselves against small upstarts, they must also remain mindful of similarly sized competitors. As these startups grow, they tend to develop from providing single-point solutions to offering comprehensive platforms with a wide range of features and applications. This can lead to a problem of feature parity with other large businesses in the same industry. Consequently, it is important for corporations to stay abreast of the latest advancements and solutions in order to remain competitive.

As a project manager in an enterprise, you will often be faced with the decision between pursuing innovative developments that create new value propositions for customers, or seeking to reach feature parity with competing firms. However, many times, making such decisions may not be within your control, and you may be required to engage with several stakeholders to convince them to accept your proposals. This can be particularly challenging if these stakeholders are lacking in technical knowledge or are not familiar with the features that you are advocating for.

In Summary

In this essay, we discussed how a project manager’s role differs in a startup and an enterprise. While a project manager may need to undertake many of the tasks of a product manager in a startup, in an enterprise, they are two distinct roles. However, it is important to note that every firm has its own individual characteristics and the scenarios addressed in this essay may not be applicable to all cases. Therefore, managing complex situations may require a project manager to draw upon a variety of skills and abilities.

In conclusion, startup businesses have malleable processes allowing the project manager to make rapid decisions that have a considerable impact on the organisation as a whole. Due to the shorter development lifecycles, the project manager must remain agile in order to quickly react to any fluctuating market trends.

As a project manager at a startup, one can expect to face numerous challenges. With the growth of a company, duties can become unclear and lead to a variety of issues. Clients and co-founders may encourage the project manager to take on more than the team is able to complete, as well as suggest alternative solutions that could result in legacy issues. Furthermore, the co-founders may have preconceived notions that may not be verified, so it is important for the project manager to remain data-driven and quick-thinking in order to overcome any obstacles.

As a project manager in an enterprise setting, one can leverage the company’s history of success and prior accomplishments to create a strong rapport with outside collaborators. This, in turn, makes it easier to receive the necessary requirements from experienced professionals and colleagues who are accustomed to dealing with customers. Furthermore, a Project Management Office, even if its resources are limited, can help to reduce any issues that arise during project implementation, as well as manage any potential risks.

The successful management of business projects is inextricably linked to the size of the organisation. To avoid delays due to the need for multiple approvals and sign-offs, project managers must ensure that their preparations are thorough and that the Project Management Office (PMO) is adequately involved. As more people and departments become involved in the process, it is inevitable that miscommunication will arise, and this should be addressed by implementing the necessary structures and mechanisms to ensure that it is kept to a minimum. Furthermore, in an environment where development lifecycles are becoming increasingly longer, project managers must be aware that they are competing with both established organisations and new startups.

Recognising the differences between the two contexts in which project managers function is critical for anticipating the challenges that may be encountered when transitioning from one environment to the other. By gaining an understanding of the primary distinctions between the two contexts, project managers will be better positioned to make accurate predictions of the potential obstacles they may face during the transition.

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