Welcome to the Jungle: A Guide to Finding, Landing, and Succeeding in a Startup Internship | MBA Core Fellows Series

By Steve DeSandis, MBA ’21 | MBA Core Fellow

Landing a summer MBA internship at a startup company may seem like a daunting process, often described as taking to the “jungle” with your machete to hack a path for yourself in uncharted territory. Over the winter, you are starting to see your classmates locking down consulting, big tech, and investment banking internships. You may brush the “FOMO” feelings off, but you can’t help wanting that certainty about your own summer plans (especially given the additional uncertainty caused by the global pandemic). You knew the startup path would be different, but that doesn’t change the fact you may be feeling anxious, uncertain, and perhaps clueless on what startup you’re interested in, let alone the type of role you could play. You are not alone. Myself and many of our classmates have had the same feelings. While there is no “super highway” to hop on for finding, landing, and succeeding in a startup internship, there are approaches to the process that helped me break things down into manageable steps. 

In his book Entering StartUpLand, Jeffrey Bussgang, a venture capitalist, entrepreneur, and professor at Harvard Business School, offers a demystified approach for identifying what role and type of startup could be right for you. I found this book incredibly helpful and have incorporated aspects of his approach here. Anyone looking for an accessible how-to for entering “startup land” should consider picking up this book. 

I suggest an adapted methodology for finding and succeeding in a startup internship: 0) know your goals for a startup internship, 1) understand the type of startup role that is a best fit for you, 2) identify your target startups, 3) position yourself well during recruiting to land the job, 4) understand your role and expectations going in, 5) succeed by creating value, contributing, and building connections and 6) exit gracefully. 

0) What are your goals for a startup internship? 

An essential step before starting your startup internship search is knowing your goals for your summer internship experience. Reflect early on and throughout the process. Why are you interested to intern at a startup? Do you want to see whether startup life is right for you? Whether a new hot industry is as interesting as you think? Could your skills translate to being a successful business development manager at digital health startup? Whatever your goals are, be clear on them, write them down, and go into the job search with them in mind. 

1) What role is right for you? 

Roles and titles are often messy in early stage companies. When companies are quite small, founders and employees “wear different hats,” meaning their roles change with the dynamic nature of the work. Roles may be very loosely defined for younger startups with less than 20 or so employees. After a couple years in business and/or after growing to more than 20 or 30 employees, the nature of the organization, work, and roles often become more structured.  

While startup dynamism may make role and title definition ambiguous, there are indeed common types of roles in most startups based on the priorities of the company. These roles and areas of focus include: product manager, business development manager, marketing, growth, sales, and finance.  

Which type of role is right for you? Do some research on what these roles at a startup usually entail (detailed role descriptions fill most of the pages of Entering StartUpLand). Reflect on what motivates you. Which is a fit for your interests and skills? What are your strengths and challenges to work on? Are you wanting to stretch yourself to apply your skills to a new type of role? How do you see yourself fitting into and succeeding in a given role? All these roles are essential to a startup’s success and understanding which fits your interests will make the search for the right startup more straightforward. 

2) What type of startup is the best fit? 

Let’s say you decide Product Manager is your target role and your goals for the internship include determining whether this role would indeed be a good fit for your skills and whether the startup scene could be right for you when looking for full-time employment. Great! Now what? Bussgang offers a helpful framework for narrowing down the myriad of startup opportunities: pick a domain, pick a city, pick a stage, and pick a winner. 

Pick a domain: What are you passionate about in regards to the type of industry or domain? Are you more of a B2C or B2B person? Do you want to serve the needs of large customers or smaller ones? What are your favorite apps, services, or products? Do you admire a specific brand? What do you spend your free time reading or thinking about that gets you excited? Reflecting on and answering these questions honestly for yourself can provide the domain direction to narrow your interests. 

Pick a city: Startup hubs like Silicon Valley, Boston, and New York get much of the startup buzz and for good reason. These startup hubs are full of entrepreneurial people, investors, and activity, which increases a startup’s chance for success. Picking the right city for you will increase your chances of success at your first startup and any subsequent startup job searches. While this may be less of a consideration for an internship, be intentional in how you start building your startup network, keeping your goals in mind.  

While you should consider looking at these startup hubs, you should pay particular attention to the cities where your preferred domain has clusters of startup companies. You should also keep in mind that the increasingly virtual nature of startup collaboration (and the global pandemic) means more and more startups and their employees are less tethered to a physical location and may be open to hiring you wherever you wish to live.  

Aside from a city’s professional opportunities, consider how well it fits into your personal preferences, goals and relationships. Will your partner be able to find a job in the long-term? Is it important for you to see family and friends regularly? The lifestyle and culture of a city must be appealing if you wish to thrive. Do you hate the cold and want to live near a beach? Crave easy getaways to nearby hiking mountains and ski resorts? How will a city’s cost of living affect your lifestyle and goals? The city you choose will have a big impact on your startup job, future job prospects, and quality of life.  

Pick a stage: Startups describe a broad category of companies ranging from a handful of people to several thousand. Do you want well-defined tasks and structured support? Or do you thrive when given a rough direction, goal, and the freedom to explore and create? Are you comfortable working at a company where future rounds of funding are uncertain, meaning your medium-term job prospects are uncertain? Choosing the right stage startup mostly depends on your appetite for risk, uncertainty, flexibility, level of autonomy, and other personal preferences. 

Pick a winner: Picking a domain, city, and stage can be a more objective exercise based on your preferences. Picking a winner can be difficult and prone to mistakes. The best investors in the world don’t always get it right, so how can you? The best way to navigate this is to think like an investor, identifying companies in your preferred domain, city, and stage and conducting due diligence through research (e.g. Crunchbase, Pitchbook), customer reviews, and conversations (MIT alums, classmates, network). Use your best judgement when considering the startup’s team, market, and business model. You should ask questions of the founders, employees, customers, lawyers, and investors to understand a startup’s prospects. 

Bussgang summarizes to “aim high, seek out the incremental networking meetings, and pick yourself out a prospective winner. Things may not work out, but at least you’re putting yourself in a position for a little positive serendipity.”

After picking a domain, city, stage, and winner(s), you should have a list of companies in mind and be ready for the next challenge: getting hired. 

3) How can you position yourself to land the job? 

The two most important aspects for getting a job at a target startup are finding yourself a warm introduction and preparing yourself to have a point of view on the company and what you could do to add value. 

Getting a warm introduction: As a student at MIT, you have an invaluable asset: the network. MIT and Sloan alums are all over the entrepreneurial ecosystem. Start here to identify any connections to a target company. Attend and meet startups at the numerous entrepreneurial events (virtual or in-person) happening at MIT and around Boston. Use the MIT alumni database and LinkedIn to find connections, and even if they are only 2nd degree connections, they could still be willing to lend you a hand. Many alums remember what it’s like to be in your shoes looking for jobs and are eager to help. Expand beyond your more immediate networks as needed while always looking for related connections. In the process, be organized, focused, and persistent.  

Once you’ve identified a connection, speak with them to share your interests in the company and ask whether they would be willing to introduce you. Ideally an introduction is “warm” if the connecting person can offer you a sort of endorsement, stating to the founder or company contact something like, “I think Katherine would make a great fit at the company.”

Have a point of view on the company: You want to standout when interacting with a startup and the best way to do this is by 1) knowing their company, product, market, and customers, 2) having a perspective on what they do well and where there is room for growth, and 3) extending that perspective to articulate what you can do to help the company grow. Do your homework on the company. Research online, read reviews, try the product, speak with users to develop your own perspective. 

When speaking with the company, be strategic and intentional with your communications. You may be inclined to say what you are looking for in a role, i.e., “what can you the startup do for me?”. The advice here is to flip this around and approach conversations with a perspective of, “what I can do for you.” Be prepared to speak directly about the business and how your perspective and experience can bring them value. A “secret weapon” in this type of discussion is the idea to “come bearing gifts,” i.e., ideas or suggestions on how to improve the startup’s business. This positions you as less of an eager job seeker and more of an advisor who is already thinking critically about the startup’s business and thereby someone who would be ready to get to work from day one (what startups are looking for). 

4) What is my role and expectations for the role? 

Once you’re connected and into the interview process with a startup, be diligent to understand the role for which you are being recruited. Make sure this matches or is complementary to the type of role you set out to find. Will this role provide you a rich experience that helps you achieve your goals and answer questions you have about a company, domain, or work in general at a startup? Ask questions to understand the type and cadence of work, who you will be reporting to and working with regularly. Be clear with your manager on what success will look like for your role by the end of the summer. 

No job description? No problem! Many startups may have needs, but don’t have a job description at the ready for hiring (they have a lot of other things going on). By having conversations with the founders and/or team, you should get a sense of their goals and challenges. Listen carefully to this and think creatively how you could help them solve those challenges. In my case, I extended the “having a point of view on the company” to actually defining the role I would serve. I worked with the company’s founder to write-out a job description based on my interests, abilities, and needs identified within the company.  

While creating your own role may be an exception rather than a norm, this is the ideal level of alignment and understanding that you want before joining a startup. Objectives may evolve given a startup’s dynamism, but having an agreed upon focus for your role will setup you and the startup for a successful internship.  

5) How can I best succeed in the role? 

The summer internship will fly by. To succeed, you will need to quickly come up to speed on your role, those you are working with, and the best ways of collaborating to get your job done. Every startup will have their own ways of doing business, and you should already have a good sense of this before starting. In general, know that startups, by their nature, are going to be less able or willing to “hold your hand” through onboarding and expect that you will be driven – and yes, entrepreneurial – in orienting yourself to the role and work. 

Create value: You were hired because the startup most likely needs you to get something important done. Based on the objectives of your role, quickly take the lead in collecting and digesting information relevant to your work, speaking with and asking questions of your colleagues, customers, and suppliers to develop your perspective and approach. In startups, you need to work well independently and as part of the team, developing ideas that you can test with your manager and colleagues. Be open to feedback. Share your thinking, work, and questions with your manager regularly, ideally through recurring, scheduled check-in calls. Update progress through team meetings by sharing openly, inviting questions and feedback. Listening and offering perspective on your work and the work of others shows that you are thinking critically about your and the broader startup’s goals. The value you create will be measured in how you get your work done with others and also how well you support others on the team to think critically and succeed. 

You must have the courage to say yes or no to requests that arise. If you plan to get anything meaningful done over the summer, you will need to focus. There are lots of needs in any startup, and while raising your hand shows initiative, keep in mind your limited summer time frame and your current goals and priorities. You do not want to reach summer’s end and have three partially completed projects that make for messy transitions and create risks that none of the work will be integrated as part of the startup’s future. If you feel the scope of your work is changing or that you are getting pulled in different directions, speak with your manager and ask for guidance on how to adjust your focus. 

Whatever you do, don’t get lost by yourself. This can easily happen in startups and especially in remote or virtual work (which can feel isolating) and when your team is small and busy (which is often the case). If you feel stuck or uncertain in completing an objective or task, reach out to your manager or team. Be mindful of their time, but don’t let any fears of compromising your ego get in the way of a growth mindset in the role. No one expects you to have all the answers, but rather the company will look to you for new ideas, good questions, and the motivation to move the work forward through inevitable roadblocks. Talking through your questions and challenges with your manager or colleagues can spark different thinking and open you up to new ideas. 

Build connections: Your goals for a startup internship should include understanding what it’s like to work at a startup (especially if startup work is new to you). Once on the team, work to quickly understand who is most relevant to your work and also those who may be less connected to your day-to-day. Get to know them and their role at the startup. Look for ways to respectfully build relationships that extend beyond the immediacy of the work and into a deeper personal understanding. Ask those around you what brought them here and how they see startup life. These deeper relationships will help you work better with others and also help grow your understanding of whether this type of work environment is right for you.  

6) How should it end? 

The work objectives you set out to accomplish may very well have shifted after a couple months, but by following the practices above, you should have learned and accomplished a fair bit in the fast-paced startup environment. You will also have built connections and possibly friendships that have helped you understand the company and startup world better. However, the ultimate success of your summer internship will depend on how well you ensure the work is transitioned upon your exit. With the end in mind from initial discussions of success with your manager, where are you landing with only a few weeks left? Whether a tight deliverable is neatly concluding or a longer-term project is only half baked, be proactive in putting in place an action plan for who will own the work going forward. Your manager should provide this direction, but your depth of understanding can help inform how best to make the transition. Conclude with a final debrief with your manager on how the internship went for both of you and the company. Explore whether there could be opportunities to return full-time. Although this can be hard to promise for many startups, understanding these future opportunities at the company will be helpful when considering your full-time prospects.   

Finally, reflect on your experiences. What did you learn about the startup, domain, role, people, etc.? Did you accomplish your goals? Did your career goals change? If so, why? If not, why? Is the startup world and lifestyle right for you or should you adjust your approach for full-time recruiting? Be honest with yourself and those who are important in your life when answering these questions.  

An internship at a startup is a wonderful opportunity to explore, grow, and contribute to a fast-paced, exciting company. Only you know what is best when it comes time to taking your learnings forward into your second year of the MIT Sloan MBA program and future career. 

By MIT Sloan CDO