Sean Cheng

Intern At A Startup - Networking Your Way In

February 21, 2021 - 27 min read

Introduction

Interning at a startup is the single best way to gain clarity on a future career path.

Because startups tend to be less rigid in their organizational structures, you can experiment with a variety of roles and projects to see what you enjoy. You also get to be in a fast-paced environment, have immense responsibility over your work, and create tangible impact on your company.

But finding an internship with a startup is hard. And finding a meaningful internship that fits your interests? That’s even harder. Most people either don’t know how to begin or end up receiving opportunities they aren’t truly passionate about. I experienced both until I realized that having the chance to do work worth doing starts with defining clear goals for yourself. This is what opens doors to high-level internships and great learning opportunities. Part of this guide will teach you how to do this.

Let’s first get this out of the way: networking is the best method to get a job according to experts. But when I began, I didn’t know how to send out cold emails, what to say on networking calls, and when to ask about internship opportunities. However, throughout hundreds of emails and 50+ conversations, I learned the best methods to authentically connect with founders and ultimately secure an internship offer— all while making sure the internship was a good fit.

I will go through step by step how I received multiple internship offers (including from YCombinator, Techstars, and Sequoia backed startups) for my 2020-2021 college gap year with no prior connections or advanced technical skills. This guide is best for people looking to work at startups without formal internship programs.

I will help you:

- Understand why networking needs to be your primary tool

- Develop internship leads with companies you’re actually interested in

- Structure an effective cold email (with examples) and track your responses

- Learn what to do before and during a scheduled networking call

- Make sure your internship will be a worthwhile learning experience

- Choose between multiple internship offers

While this guide has elements that are specific to finding a startup internship, much of the advice can be applied to other areas such as identifying academic research opportunities, interning at an established company, or full-time job recruiting. I will outline the entire process of how I went from knowing nothing to receiving multiple internship offers in fields like product management, business development, and content strategy from both accelerator and venture-backed startups.

Note: All of the advice within this guide continues to apply during COVID.

Who This Guide Is For

This guide is for:

  • Novice internship seekers who want a comprehensive guide to networking. You will learn the step by step process to getting the internship you want.
  • Experienced internship seekers who want more advanced advice on crafting cold emails, developing great networking leads, and streamlining their outreach workflow. This will help take your networking to the next level and improve your success rates.

Why You Need To Network

Hiring managers receive hundreds of resumes from online applications, and the chances of you getting chosen are slim. How do you overcome this? By creating your own opportunities. The most efficient way to do this is by reaching out to people working at places you’re interested in, whether they have an application or not. Doing this opens you up to an exponentially greater number of potential internship opportunities— the so-called hidden job market. If you can demonstrate an interest in the field of your contact and show how you can provide value, there’s a good chance that you’ll find an internship.

Developing Internship Leads

When I first started networking, I spent several weeks calling anyone I knew for an internship, not slowing down to ask myself if I was interested in their work at all. The result was that I felt burnt out and discouraged when I wasn’t seeing results. I was so desperate to find an internship that I hadn’t assessed what I wanted to get out of my experience. To avoid this you must first set your goals, identify an industry of interest, and narrow down at what stage of a startup’s funding cycle you want to be in. Then, strategically target people who overlap with your desired categories.

Setting Your Goals

First, decide what sorts of skills or experiences you want out of your internship. Whether it’s UI/UX research, graphic design, sales, or marketing, knowing which field you’re interested in will automatically narrow the types of people you should reach out to. I was interested in product development, content strategy, and startup funding so I mainly spoke to product managers, marketers, and venture capitalists.

Identifying An Industry

I found that I had better conversations when I talked to someone in an industry, vertical market, or issue area I was passionate about. I tended to be more informed and more excited about it.

During my internship search, I was primarily interested in education technology startups addressing learning achievement gaps and startups with behavioral science-driven products. I could draw upon my relevant experiences (my past work tutoring and doing behavioral science research) in these calls to ask insightful questions and display a deeper interest in their work. They could see I had done my research so they were more open to the idea of hiring me as an intern.

Funding Rounds of the Startup

Startups go through different rounds of funding to grow. These rounds determine what your internship experience will be like because they indicate how well developed the company is and what its priorities are for growth. If you want a more in-depth look into this, check out this article from Investopedia.

To identify which round a startup is in, search them up on Crunchbase and click on the financials tab of their profile. While the rounds describe levels of funding, below I will describe what qualitative factors startups are going through in each stage:

Pre-Seed/Seed (generally 1-25 employees) —> Startup is just getting off the ground. They may have a prototype of their product and are figuring out how to build out, launch, and distribute their product. Your role will most likely be cross-functional (marketing, user research, product development, etc). There will be a lot of ironing out the daily processes of how the startup is run. You’ll be expected to problem solve on your own and take ownership of your work.

Series A (generally 20-50 employees) —> Here the startup should have a solid product with some customers and revenue. Now they need to figure out how to scale across different customers and markets. Work will be centered around growth and rapid product iteration. The company is becoming more established and is beginning to build out its core team.

Series B (generally 20-100 employees)—> In this stage, startups will continue expanding their market share and begin forming teams such as customer success, marketing, and sales. The founders at this point will be quite experienced and the feel will be very much like working at an established company, albeit a lot smaller.

Series C and above (generally 100+ employees) —> Startups should now be attempting to rapidly grow. They will begin to build new products and expand to other markets. At this point, the startup should have several teams and core departments working together. Processes will be pretty well established. You’ll probably specialize a lot more in your department.

Generally, if you want less hand-holding and want to take more ownership over your projects, startups in earlier rounds are the way to go. But if you want more mentorship and guidance from experienced founders, then the later rounds will be the better option. It’s possible that some late-stage startups already have established internship programs and you might have to submit a formal application. You should still network to have the highest chance of getting a job offer.

The Intersection

When you begin, you might not be sure what career fields, specific industries/companies, or startup round interests you the most. That’s okay! It’s totally fine to cast a wide net, and as you have more conversations narrow down the type of work you want to do.

Once you identify an industry, role, and startup round try to find people working at the intersection of the three. For example, if you were interested in marketing, healthcare, and want more hands-on guidance, you would look into a lot of healthcare-related startups that are Series B and above. Maybe a prescription pill delivery startup caught your eye and you reach out to their lead digital marketer for a brief phone call. These are the types of conversations that have the highest likelihood of success.

Finding People To Connect With

Below I’ve listed a few locations to source startup leads after you’ve identified your intersection. These are just a starting point but typically if you find a startup from a top accelerator like YCombinator or Techstars they’ll have qualified founders who’ll provide a worthwhile internship experience. Startups backed by elite venture capital firms like Sequoia, Benchmark, and Founders Fund will also be good bets. Another litmus test is to do additional research on the founders to see if they’ve started any companies before. They’ll tend to have more expertise.

Startup Databases: AngelList, Crunchbase

Accelerators: YCombinator, Techstars

University Programs: MIT delta v, Berkeley SKYDECK

Venture Capital Portfolios: First Round Capital, Sequoia Ventures

After identifying a startup you’re interested in, use LinkedIn or the company’s website to track down someone working there that relates to your field of interest. At larger startups, there might be department leads you can reach out to (marketing lead, product lead, etc.) but at most small startups you’ll need to reach out to the CEO.

My experience consisted of looking at earlier stage EdTech startups for my first internship because I wanted to get exposure to all aspects of running a company. So, I searched for leads through accelerators like YCombinator, Techstars, and university incubator programs.

For my second internship, I was less industry-focused and wanted to find a Series A startup so I could get some more hands-on mentorship. I looked mainly at the portfolio of top VC firms to identify leads. I then tried to find companies with product managers or growth marketers who had either worked at or founded previously prestigious/successful companies (i.e. FAANG or if their company got acquired) because they would have more industry experience to coach me with.

But now onto the next section— the cold email!

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How to Cold Email

Cold emails are emails to people with whom you have no prior connections. They are how you’ll schedule your networking calls.

By now you should have identified a specific person you would like to talk to. To find their email, I used hunter.io and RocketReach although sometimes they will not work and you’ll have to guess people’s emails. Typically, variations of FirstnameLastname@companyname.com, Firstname@companyname.com, etc. work.

Email Strategy: Hybrid Informational Interview

If you directly ask for an internship without strong enough work experience in your initial email, it becomes a lot easier for whoever you’re contacting to say no. What you should do in this case is what I call the hybrid informational interview approach. Essentially, you hint at looking for an internship within the email but frame the message as mainly wanting to schedule a call to learn more about the person’s work. This way it’s not a direct yes/no response to whether or not they have an internship because that’s an easy message to decline.

Then, your job on the call is to come across as a competent person and impress them with your energy and curiosity since you don’t have the credentials to back it up. However, this method requires a lot more outreach and has a low internship conversion rate. Sometimes you just have to put in the work, especially when you’re first starting!

This method of networking does have the benefit of you getting to learn a lot about different jobs through your calls since they are more focused on you learning about what the person does. This was helpful for me at first when I didn’t have a good idea of what people did in different roles.

Hybrid Informational Format
  • Give a brief introduction with your name, school, and major.
  • Try to tie in any commonalities you share with the person you’re contacting (same school, hometown, interests, etc.)
  • Although you might not have directly relevant experiences, try to briefly mention things that demonstrate broader character traits like discipline, problem-solving, and intelligence. You want to show that you’re capable and won’t be a difficult person to train and manage. Perhaps you did research at school involving data analytics or were a school club leader. Sometimes you have to spin your experiences to make them more relevant. For example, maybe you volunteered at a hospital and that sparked your interest in healthcare startups.
  • Have a clear “ask” and suggest times for a potential call. The times should be reasonable (not before 8 AM or after 10 PM). I would ask for a 10-15 minute call to keep the commitment level relatively low.
  • Be respectful and acknowledge that they may not have time to meet with you.
Hybrid Informational Advanced Tips
  • Keep the email as short as possible. Try to stay around 150 words. Founders and department heads are extremely busy and will not read long emails. Be direct and to the point.
  • Write a concise subject line. I liked to use something like Call About Your Work With A Swarthmore Student?
  • I scheduled my emails to send periodically at 10 AM on Tuesdays using Gmail. This is based on several studies citing that as the time most emails get read.
  • Follow up a maximum amount of three times and space out the emails within a week of each other. This is crucial. Keep the follow up respectful and acknowledge that they may be busy.
  • After you confirm a time to meet, ask if they’d like you to send a calendar invite. This makes you seem thoughtful and prepared.
Hybrid Informational Example

Below I’ve attached a screenshot of a cold email that I sent incorporating these guidelines that got me an offer.

Link To Screenshot

Hybrid Informational Email Breakdown

Some key things to note in this email:

  1. It’s very concise and there’s not a lot of fluff.
  2. The “I would love to learn more about what you’re doing… and where I might be able to fit in” portion of the email is what I mean by asking for a hybrid informational interview. It implies the potential for an internship but makes it low pressure by putting more emphasis on learning about this person’s startup. What could’ve made this email even better is if I asked about the person’s past work experience and what led to them founding/working at a startup (i.e. putting something like “I also saw you worked as a product manager at Google before and would like to hear about that as well” into the email).
  3. I propose exact times and also politely acknowledge that if those times don’t work or the person is too busy it’s completely okay if we aren’t able to connect (“Please let me know if those times work and if now is too busy I completely understand”). This makes the tone less demanding.
  4. I didn’t have a ton of relevant work experience in the EdTech space of this particular startup since they specialized in a pretty niche field. And since I’ve never actually worked at a startup before it was a hard initial sell. But I demonstrated my analytical skills by mentioning my past research and hinted at my interest in startups through my VC work. The college access initiative was also a way to show that I was genuinely interested in education (even if it wasn’t tied directly to the startup’s work). Remember the goal is to merely demonstrate that you’re competent and interesting enough to talk to.

Email Strategy: Direct Ask

If you have more past work experience, you might opt for a more direct approach and ask for an internship in your initial email. I did this after getting more startup and product experience.

This strategy works best if you also have a very specific role in mind. You can’t just ask for an internship without having something in mind because that isn’t an actionable request.

Also, if you want to work in a particular role you need to have a strong grasp of what people normally do in that role. For example, if you directly ask for a marketing internship, during the first call they’ll probably ask why you want to work in marketing and you’ll have to a) Articulate that you understand what marketers do and b) How your past experiences/knowledge informed your knowledge of wanting to do marketing. This is hard to do without relevant experience, although it can be done if you’re very well informed and know how to spin what you’ve done in the past.

Direct Ask Format / Notes
  • Give a brief intro with name, major, and school.
  • Try to tie in any commonalities you share with the person you’re contacting (same school, hometown, interests, etc.)
  • State what role you’re looking for.
  • Connect past experiences to that particular role and show you’re qualified.
  • Show where you can add value.
  • Ask for an interview.
  • Remember to follow up a week later if there’s no reply.
Direct Ask Example

Here is an email using the direct ask approach that got me an interview.

Link To Screenshot

Direct Ask Email Breakdown

Some key things to note in this email:

  1. Clear ask of what exactly I was looking for (“help as a product intern”).
  2. I quickly tied in my social proof of my experience working at a Techstars backed company (“working at BestFit”) which strengthened my credibility since Techstars is a top startup accelerator that only admits a select few companies.
  3. Went into detail about my past product experience while discussing my book. In this situation, I had to spin it into a relevant product experience since I was talking to a software-based startup that doesn’t sell consumer products. Anyway, it worked.
  4. Mentioned where I could add value (“build out its product and speak to users”). This could’ve been stronger if I had a better idea of what the company was working on. Usually, you can’t figure this out so I just went with a generic thing that product managers did. However, what was nice was that “speak to users” was similar to what I did previously in “interviewing high school students” which made me seem more qualified.
  5. For direct internship asks I didn’t propose a time for an interview since it comes off as rude to assume they want to interview you.

Tracking Your Emails

You must use a spreadsheet to track who you’ve been reaching out to because you’re going to be emailing a lot of people (we’re talking emails to 50+ different people). A spreadsheet will allow you to schedule follow-up emails and remember what you’ve discussed with each person. Here’s a spreadsheet that I use.

The Call

At this point, you should’ve been able to schedule a call with someone you’re interested in speaking with or heard back that they want to interview you. Now your goal is to show that you’re a) Well-informed b) Smart and c) Not a jerk.

The style of your calls will be different depending on which email approach you used. Hybrid informational interviews will tend to be more relaxed, while direct internship asks will usually operate like regular interviews. Regardless, preparation before the call will be roughly the same and the call itself will be the same except for a few portions.

Before The Call

Before the call make sure you have a good understanding of their company and work history. Use LinkedIn and scour the person’s profile and their company website for the latest news. Come up with a list of insightful questions that don’t have answers that can easily be found online. Don’t stalk their Facebook and ask them creepy questions.

Solid questions include ones that dive into why the person you’re speaking with chose their particular career path, what they’re working on now, and what advice they’d give to someone interested in a similar field. If you’ve done your research then questions about industry trends or a more niche topic within their field can be good. However, trying too hard to be “smart” can rub people the wrong way so tread carefully.

Preparation is important for the call but ideally, you can listen to what they’re saying and ask deeper questions based on what they’ve just said. This takes practice and doesn’t come naturally to everyone so don’t be discouraged if your first few calls aren’t as good as you expected.

For calls that resulted from direct internship asks, make sure to prep for standard interview questions like “Why X role,” “Why this particular company,” “Tell me about your past experiences,” etc. more rigorously. Although you may still be asked these questions during a hybrid informational interview they’ll tend to be more casual.

During The Call

I liked to view the call as primarily trying to learn more about the other person’s work whether or not I had directly asked for an internship. Displaying your curiosity and enthusiasm is the best way to win people over. A side benefit of asking insightful questions is that they’ll give you a glimpse into what different careers are like and help you determine if the company is a place you would want to intern at. Going into the call with the mindset of only getting the internship doesn’t allow you to effectively evaluate the opportunity and create a genuine connection with the person you’re speaking with. A helpful reframing if you’re nervous about getting on calls is that your goal is seeing if they’ll be a good match for you.

Below is an outline of how you should structure your call with whoever you’re talking to. Of course, this is just a guideline and it will be up to you to analyze how the call is going and make adjustments accordingly. Notes on variations for a direct ask call will be italicized.

Step 1: Exchange pleasantries and engage in basic small talk

  • The goal here is to be relaxed and be yourself. Don’t come on too strong or be too aggressive. Make sure to thank them for taking the time to call.

Step 2: Transition into your reason for the call

  • There’s always that awkward moment during the call when it’s silent on the phone and no one knows who’s supposed to start the conversation. To avoid this, ask if it’s alright for you to introduce yourself and ask a few questions about their career.
    • Ex: “Would it be alright if I introduced myself and asked you a few questions about your career?”

Direct Ask Step 2: Transition into your reason for the call

  • Usually, with a direct ask the purpose will already be clear and the person will ask you to tell them a bit about yourself. If that doesn’t occur feel free to say something like “Would it be alright if I introduced myself and why I’m interested in interning at X company?”

Step 3: Introduce yourself and ask your questions

  • Give a summary of yourself. Name, major, school, activities, and why you’re reaching out to this particular person are all great things to cover. Bring up why you’re interested in their work or company. Ask the questions that you had.

Direct Ask Step 3: Introduce yourself and respond to questions

  • Pretty self-explanatory. It’ll be like a standard interview.

Step 4: Wrap up the call after you reach the time allotted (usually 15 minutes) and make your ask

  • You don’t get what you don’t ask for. End the call by saying something like, “Thank you so much for taking the time to talk. Before I end, I wanted to ask about how someone like me might get involved with your startup?”
    • If they say there aren’t any opportunities that’s okay! It’s a numbers game; thank them and ask if they might have any leads on other opportunities similar to them.
    • If they say they have an open position, congratulations! You’ve just landed an internship!

Direct Ask Step 4: End of interview + ask your questions

  • Once the interview has ended they’ll probably ask you if you have any questions. Ask them at this point. Make sure to ask what the next steps are for a potential internship.

Step 5: Send a thank you email

  • This is just basic courtesy. The person you spoke to is very busy and took time out of their day to talk with you!

Step 6: Follow Up Periodically

  • A no now doesn’t mean a no forever. Even if you get turned down for an internship, you can still stay in contact with the person you spoke to if you feel like you connected with them. Follow up with interesting articles, career updates, or stories on how you applied their advice to your work/life and how it helped you. Build up the relationship and if in the future you still want to intern with them feel free to ask again about opportunities.

In the beginning, most of my calls didn’t turn out great. Especially with the hybrid informational interview approach, I felt awkward and wasn’t able to articulate myself clearly. I didn’t have a coherent elevator pitch about why I was reaching out and that made conversations difficult because the other person didn’t understand who I was or how they could be helpful to me. But over time, I was able to refine my elevator pitch and ask better questions based on the flow of the conversation. It takes practice.

In some cases, you won’t be able to connect with the other person and that’s okay. Just do your best to help them help you. That means being well prepared for each call using all the steps I shared above.

One of my most memorable hybrid informational calls didn’t end in an internship offer but was memorable because I received an inside look into the psychology of how employers view interns. The person I spoke to shared how I could add value as an intern and be more successful in my work.

I also received book recommendations, life tips, and career insights from many of my calls. These helped me clarify how I wanted to structure my studies. For example, I didn’t realize how much data analytics is a part of marketing until after a call with an experienced marketer. After this realization, I’ve read a lot more about statistics and how I can study it. I guarantee if you view these calls as more than a means to an end, you’ll learn more than you ever expected.

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Choosing Between Multiple Internship Offers

Typically you can’t choose between multiple internship offers because startups without established internship programs expect you to start as soon as possible (usually the next week). However, if you have multiple networking calls lined up and you receive offers all around the same time, you can ask for a few days to think about it. Just be aware that this can be risky as some startups will try to find someone else during this time. This happened to me. The interviewer asked if I could start the following week and because I didn’t respond with a definite yes they never got back to me when I reached back out the next week.

Choosing between offers ultimately comes down to which company aligns most closely with the goals, industries, and preferred round of a startup that you identified earlier. Make sure to ask for examples of the type of work you’ll be doing, and if the startup has had interns in the past feel free to reach out to them to ask them about their experiences. You might want to also consider how experienced the founders are and if they seem like they might be good mentors for you going forward. Don’t be afraid to ask about how much mentorship will be provided during the internship.

After considering all these elements, one company will most likely stand out to you, and if multiple startups appeal to you equally you’re in luck! You can’t make a wrong decision.

For me, I received six internship offers throughout my initial search. I ultimately chose the company I interned at because the founders set extremely clear expectations on what I would get out of the internship and had strong academic backgrounds within education. Before the internship started I had to fill out a slide deck detailing my goals (learning about marketing, fundraising, and product development). Then, the founders gave me a list of potential projects I could work on that fit underneath each of my goals which I found reassuring. The startup was also within education technology (a vertical I was interested in) and was pre-seed (I wanted to get broad exposure to all the different aspects of running a startup). No other offer combined all these elements I was looking for so it was an easy choice.

We’ve Covered A Lot

At this point, I’ve walked you through the entire internship search process. If you followed the steps in this guide, you should be well on your way to securing your first job with a startup.

Feel free to send me your questions and thoughts via Twitter @seancheng_. I’ll do my best to answer them. If you liked the information in this guide consider putting your email in the section below to get exclusive access to new guides and posts.

Thank you to Nick Fong, Valerie Hu, Michael Wallerius, Roma Bedekar, Hojune Kim, Christina Wang, and Tim Fu for reading drafts of this and providing valuable feedback. This piece wouldn’t have been possible without their insights. Special thanks to both Kelvin Yu and Matt Maiale for answering my questions on the internship search process and serving as gap year mentors. I’ve incorporated much of their advice into this guide. Go check out their websites for more information on startups, internship hunting, and general advice.


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