Join a Rocketship: How to Get a Great Job at a Startup | Charlie O'Donnell | Skillshare

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Join a Rocketship: How to Get a Great Job at a Startup

teacher avatar Charlie O'Donnell, Xennial. VC @

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Taught by industry leaders & working professionals
Topics include illustration, design, photography, and more

Watch this class and thousands more

Get unlimited access to every class
Taught by industry leaders & working professionals
Topics include illustration, design, photography, and more

Lessons in This Class

    • 1.



    • 2.

      Funding Stages


    • 3.

      How Startups See You


    • 4.

      Conference Project


    • 5.

      Media Sources


    • 6.



    • 7.

      Using Social Media


    • 8.

      Convene People


    • 9.

      Define Success and Measure Outcomes


    • 10.



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About This Class

The Social Network, Shark Tank…  Startups have entered the spotlight in a major way, leaving big corporate cube-dwellers to ponder a greener life on new grass.  The idea of a more entrepreneurial career, helping to build a fast growing startup is interesting to a lot of people, but they don’t know how to break in.  This class will cover how you can position yourself to get that coveted job at a rocket ship through personal branding, navigating the startup community to research opportunities, and gaining a foot in the door through relevant project work.

Meet Your Teacher

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Charlie O'Donnell

Xennial. VC @


I'm the sole Partner and Founder at Brooklyn Bridge Ventures.  The fund makes seed and pre-seed investments and was the first venture firm located in Brooklyn--where I was born and raised.  Brooklyn Bridge invested in the first rounds of The Wing, Petal, Canary, Ample Hills, Tinybop, Hungryroot, Clubhouse, and goTenna among others.

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Level: Beginner

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1. Introduction: Hi, I'm Charlie O'Donnell and I'm a partner at Brooklyn Bridge ventures, a venture capital firm located here in New York. I've had a lot of experience with start-ups. I've invested in over 60 companies, helping them with all sorts of aspects of their business. There's nothing more important that I can do for our company, than to help them make a great hire. Which is why I focused on recruiting in talent as my expertise. I've spoken at universities, I've taught classes, and I've really tried to understand how great talent winds up companies and how companies can find and hire the best talent. I understand why people want to work at startups. It's exciting to think about being an early part of a small team that grows into something really big and makes an impact on the world around them. Startups can be a really game-changing aspect to your career and an opportunity for you to get known as the person who helps the next big thing get to that point. It's not always easy to break in. There are a lot of companies promising a lot of big dreams, and they're always out there looking for new talent, but it's very different than the traditional company hiring process. In this class, I'm hoping to provide some insight into that process and to help prepare you to take advantage of all the talents you have to bring to bear and to show those talents to your prospective employers. Key insight into this class is to focus on solving the problem of the person across the table. This person might be a founder or an early hiring manager or a recruiter, but at the end of the day, they probably don't have as much experience hiring as someone you might talk to at a bank or a big consulting company, or somebody that's been in the process of doing this for years. A lot of times what attracts someone to a startup is the fact that the environment is fast-paced, there can be something new and different everyday. People think they have to present a face that fits in with that environment, when in reality, you are there to help bring order to the start-up chaos. While you're thinking your background might be a little too traditional, startup is actually thinking, they'd like to hire someone who bring some structure and bring some order to what they've been experiencing. They're hiring you for your background, and they don't necessarily expect you to change just because it's a startup. I'm going to challenge you to do a fair amount of research in this class and some thoughtful self-assessment. What I'm sure of is if you complete these tasks, you'll be better positioned to see all of the available opportunities and to have a better chance to take advantage of them. 2. Funding Stages: Startups come in very different stages with different levels of sophistication in the hiring process at each stage. The very beginning, you probably are just dealing with a couple of founders. The initial founding team is usually made up of category experts who are either building or selling the product. There's not much else to a company at this stage. Sometimes, you don't even have a product and market yet, which obviously means you don't have any revenues. Generally speaking, these types of companies at this stage aren't going to have a lot of extra people. They're not going to have anybody who is doing strategy or communications, the type of roles you might see in a larger company that are really important when a company is larger and in market with a product. These types of task generally get lumped into things the founders do when they have time. This is the riskiest time in a startup's life. It's also the biggest opportunity for somebody who joins. You're going to have to figure out that balance for yourself. The company might not be around in a year, but it could also be a great ride if you're up for it. Generally speaking, early startup employees have the most upside in the accompany because they're able to get the largest share of equity. Somebody who joined Google as employee number three got way more shares when the company went public than someone who joined as number 1,000. Startups tend to think that for their goals in terms of rounds, you'll hear this term a lot around a financing. As a professional investor, I give a company a specific amount of money to reach a certain set of goals and if they meet those goals, then we might be in for another round of financing. Each time the company takes a little bit of risk off the table and maybe by selling their first customers or getting to a certain level of revenue, I'm willing to put up more money when there's less risk on the table. If you're not sure whether or not a company will be able to make it, you should be able to just ask the people interviewing you, "What are the goals for the next round?" They should have a very clear idea of what they need to achieve to continue to be a viable entity, at least until they're able to achieve profitability and stand up on their own. If you're a little skeptical, don't worry about it. Generally speaking, you're right to be skeptical. Most startups don't make it. If they don't pass a really quick reasonability test or you find yourself maybe not convinced, chances are, it's not you. The best startups have the clearest ideas and the clearest vision from markets that make sense to a lot of people. If you're still not convinced or you're not sure, feel free to reach out to someone who invests in startups regularly, or maybe even someone who covers them like a journalist. They're used to hearing multiple startups stories and that's a good way for you to check as well. Talk to multiple companies. If you spoken to 20 companies, you're going to get a much better sense as to which entrepreneurs are more convincing than others. Talk to someone who's already successful, or go out to a conference or a talk or a meet up and hear what somebody sounds like when they've grown a company to a 100 or 200 or 500 employees, you're going to get a different sense listening to that person than to someone who really isn't convincing when they're just at three people. Generally speaking, companies that aren't yet a 100 people tend to have somewhat unsophisticated hiring processes. That's what we're really focused on now. Once you get up over 50, 75 or a 100 people, it tends to look more like a small company that you're familiar with. The hiring process is more repeatable, it's transparent, it's a little more process-driven. You'd have an easier way around navigating it. 3. How Startups See You: I'd like to share with you one of those common mistakes people make when trying to get a job or startup. Everybody thinks a startup is a fast pace, flexible, slightly chaotic environment. A lot of times when you're coming from a more established industry, you feel a certain pressure to fit into that environment. So what do people do? They approach an early stage founder, and they tell them, I'm capable of doing anything, just let me know what you need me to do. This is literally the exact opposite of what's helpful to a founder. Think about the person on the other side of the table. They come in, every day is a little bit different, every day has a new problem, things aren't consistent yet. They would love to be able to walk into their job and have everything be organized and everything be laid out for them and for things to be running very smoothly. They look forward to the day when that happens. In order to do that, they need to put out as many files as possible and to make sure that each of the areas of their company is running in a really organized, really structured way. That's the only way the startup is going to make it to success. When you come in and you say, "I can do anything." That doesn't really help them make a decision. If you come in and say, I do this one specific thing really well, and that happen to match one of the things they need to get done, that makes the hiring process a lot easier. Too many times candidates are too unfocused in their interviews for a startup, because they think that's what the startup is looking for. They're afraid that they're traditional company background is going to look too rigid or too traditional for this fast-paced startup environment. So they fail 10 times out of 10 in convincing the founder or the hiring manager that they're going to help bring order to the chaos of a startup, and that's really what they're looking for. How do you do that? Think about this scenario. In many cases, you might be the first person in that functional area to get hired. So you have a team of, let's say mostly technical people hiring their first head of marketing, or their first marketing manager, how well do you think they know what the job looks like? How well do you think they would be able to vet someone who comes in with a marketing background. They don't have any expertise in this area whatsoever. So not only are you tasked with trying to convince them that you're the right person, the hidden task is to tell them what this job is all about. When you hire at a really early stage, especially when a team that matches your expertise isn't built out yet, think of yourself as a hiring consultant. As a hiring consultant, you're telling this team what they need, how to vet success, and then you're telling them why you're that person. So you have to interview yourself in the interview, to say, "Hey, at this stage of the game, here's what your sales function should look like. Here's how you would measure it. Here are the metrics that you track. Here are the structures we'll put in place to track those metrics. Here are the tools I would suggest to use them. Basically you're telling them what success is and telling them what a successful head of marketing or head of sales or whatever you're being hired for does. Then you're showing how you fit into that structure. It's more information than people are used to sharing when they're on a traditional interview. Usually in a traditional interview with a larger company, the person on the other side of the table knows exactly what they're looking for, and you're just trying to fit yourself into that mold. In this case, you're telling them what the mold looks like and then trying to fit in. 4. Conference Project: Let's say you're a non-traditional candidate or you're trying to transition into a new area that doesn't necessarily match your resume. How can you figure out what specific jobs your skill set matches in the startup world? Once you figure that out, how do you figure out which startups to approach or where they are? This is why I suggest a conference project as a good exercise to do a survey of what's out there. What do I mean? I think that candidates trying to get a job at a startup should have about a conference organizer's worth of knowledge about an industry. Think about your average one or two day conference. There's something like five or six panels a day, 1-4 speakers on each paddle, and generally topics are about trends or challenges in the industry. This is actually a good proxy for the size and scope of the knowledge you need to have in order to successfully get a job in that industry. Why not actually pretend to run a conference as a way to organize your trek throughout the industry? Imagine you're going to run a conference on a particular area or startup seemed to be clustered. If you're not sure how to narrow this scope, I've included a worksheet on how to make sure you're doing something a little more specific than just tech versus something that's maybe a little too specific, like using the block chain to grow panda bears in captivity. I don't think there'd be a lot of startups for you to choose from and certainly not a startup job. Things to keep in mind. Generally, each conference has a balance of headlines speakers versus tactical folks who are probably the most interesting and will probably give you a really specific advice on how to do a particular thing, but they might not be the people who sell tickets. Your network should be a balance of both of these. People who are really influential and then people who can give you the nitty-gritty of what each job is like. To do this exercise, create a template and starts searching out topics. Ask people in the industry. If you were to go to a topic, a particular session on a topic, in a conference, what would you want it to be about? What would be really useful to them? Maybe you can find some existing conferences that are out on the web. But I will still challenge yourself to make the topics more interesting because I'll be honest, a lot of these conference aren't that interesting. Here's another way to think about this challenge. What if you actually did it? Now, I'm not an expert event organizer, and there's plenty that's been written out there. I'm not going to tell you necessarily how to do that, but once you get a space, and it's actually a lot easier than you think. Think about it this way. Wouldn't it be easier to get a job at a start-up if you are someone who organized a really great informative conference about their area of interest? It's certainly be it a lot easier to get a job being that person than just someone who comes from a completely different industry. 5. Media Sources: A lot of people are asking me about the use of social media in terms of getting a job at a startup company. Before I tell anybody to tweet or write a blog, I remind them that startups produce a lot of content. Founders and investors are sharing best practices, things they've learned, and a lot of things about their own personal branding in order to get ahead in their own careers. So it would really be a waste for you not to take advantage of this treasure trove of information. In fact, there's a lot of expectation on behalf of founders that you've put out what they've been writing about and that you've been following the industry. Before you even think about whether or not you should be writing anything, or posting anything yourself. You should really be checking out what other people and what other expertise people have already posted. If you're a career switcher and you're thinking about moving from one area to another, you can get up to speed in a very short amount of time by checking out areas like medium or YouTube to figure out best practices. You could even create a course for yourself, or potentially find one on skill share to figure out what are the things that I need to know to be an expert at marketing, sales, PR, or any of the functional business areas this startup might be hiring for. 6. Consulting: Someone I knew recently told me they were having a little bit of a problem finding a full-time position. They were looking for something entry level as they had just recently graduated school. I suggested to them that they might think about consulting. Their immediate reaction was that they probably didn't have enough experience to be a consultant. I answered, "Okay, well, you might not have enough experience to be $1000 an hour consultant, but at some price your skills have to be useful." Because you were just asking that company to sign a one year or at least one year consulting project for $50,000 or $60,000 or $70,000, essentially a full time job. If you're not sure whether or not a company should risk an hourly rate for you, then it's going to be really hard to get a full-time gig. Consulting can be a great way for both sides to take a chance on each other. It focuses on specific deliverables and what the actual job entails, which is something that anyone going for a full-time job should really focus on and is where a company should be focused on when they hire someone. As an exercise, lay out some different types of consulting solutions transparently. Every consultant should have a really short-term gig in hand. What something that someone can spend an hour or three hours or half a day or just a day on in order to get a quick return on your time. Maybe you come in and you do an assessment of a particular area, a bit of an inventory on things they already have going on. Where you can spend the morning doing some interviews, talking strategy and spend an afternoon writing up the overview or coming up with a pretty specific deliverable in a report. These types of really short engagements can be a way to get in the door with someone and actually provide the company a lot of interesting feedback. After that one day turnaround project, think about what you'd like to spend maybe two weeks at a company. What could you get done in two weeks? They'd be reasonable deliverable for where the company is. Longer than two weeks? How about something like three months? Three months is a longer project. Maybe it's some research and going into a new area or getting a new area started and trying to deliver an offshoot of an existing product and put it in market. Either way, it's something that you can ask a lot of other startup companies what they've had consultants do for them. The consulting market is already established for early stage startups. A lot of times they don't necessarily have the budget to hire somebody full time, but they go out and get an expert for shorter term in order to get some important deliverables done. This is something that you can put yourself out there doing. If you can't get anybody to pay for it right away, I'm absolutely sure that there's a startup out there who needs that work done and be willing to be a part of a public case study for you to show off what you can do for a company if they take a chance on you as a consultant. 7. Using Social Media: Let's talk about your use of social media and what that means to get a job at a startup. Immediately, a couple of things went off in your head. You probably thought about what it's like for other people to use social media. Maybe you don't have the best reaction to that. Maybe you think that anybody who blogs or tweets is being boastful about a bunch of stuff that nobody really cares about. Here's the key. That's not what your use of social media would be like. Well, if it is, maybe you should rethink it. But I have a feeling it's not because you're taking a class in order to figure out how to hone your skills and improve in order to get a job. Right off the bat, you're someone who doesn't necessarily think they know everything. If you were to write a blog or you were to tweet, you wouldn't necessarily act like the worst behaviors out there on the social platforms. Let's get that out of the way. Your blog would be a lot more interesting, a lot more down to earth, and you wouldn't come off like a know it all because that's not the type of person that you are. One way to think about writing is in terms of being a public student. When I first started out my blog about 14 or so years ago, at This Is Going To Be I really wasn't an expert on anything and most of my writing was about what I was observing. Anybody can be observant. Anybody can point out their reactions to what experts have written and why would they agree or disagree. Just as an exercise. It's important to think to yourself, "Hey, does that resonate with me or doesn't it?" Being a public student just means you're out there trying to figure things out and making observations along the way. No one accuses a public student of being boastful or too authoritative. Writing is a great way to also practice your narrative and make sense of all of the data that you're hearing about and all the content that you're hearing about in your job search. Think about the purpose of a story. One of the reasons why human beings even created story in the first place is to remember them. Stories have a logical order. When you try and write something down or speak it to somebody else, you take all these little desperate pieces of knowledge and you try and weave them into something that logically makes sense. You can't take coffees every day or read everyone's blog and not have a means to actually process the information. Writing can do that. Maybe you might start off just journaling to yourself, but I actually think it would be much more useful to share it publicly. The interesting thing about people's worry when they start to think about sharing something publicly is that before they start writing, they're really worried about putting something out there that people might make fun of or might be controversial. Then once they post and no one comment and no one retweets it, then they're worried why no one's reading it. It's really interesting how you have the immediately opposite reaction once you actually take the time to write something interesting. Think about how useful this is to an employer. I could check out your resume, but that doesn't really tell me how you think. If I were hiring a photographer, I would definitely check out their online portfolio. But I'm not, I'm hiring a knowledge worker. Where's your brain's portfolio? How can I get a sense of how you think, even if no one's reading it, just having a medium site, or a blog, or link to twitter in your signature gives me a little bit of extra insight into who is this person that's reaching out to me with this form intro letter and this resume. Now I could actually get a chance to see a little bit more about what does that brain that I'm going to try and bring into my organization, what's it doing on a regular basis? It just helps with the conversion process. Makes it much more likely that I pull out something interesting or that I found interesting and start that discussion on a much more deeper level than just say," Hey, tell me where you've worked." This gives people a lot of insight into really functional line of thought that maybe isn't reflected in your prior resume work. That's why I think it's important to put yourself out there on social media. It's also important just as a means of making connections. You can start to follow along with someone and comment on something that they said, and you'd be surprised. Maybe you would previously emailed them about working on their marketing team to no avail because they were busy but a twitter conversation might actually land a cup of coffee or even an interview. It's important to be out there in the spaces where people are already participating. 8. Convene People: I'd like to share with you a quick story of a friend who wound up being very successful in a new and emerging area. She was trying to figure out what she should do for her next career step and my suggestion was, start a meet up. Now, this isn't a particularly normal suggestion for job changers. Usually it's get your resume out there or update your LinkedIn, but I actually thought it would be much more useful to put everybody in a room together who had the same interests that you did. To really get yourself in the flow of what's going on in your industry, what the trends are and just who's even out there, it doesn't require a lot of experience or expertise to be a convener of people. Frankly, all you really need to do is pick a bar or an event space and put it out on that you're hosting an event for a specific topic or just for people interested in an area. Usually you can find experts who are willing to speak in front of a crowd and it's oftentimes easier to find those people who are willing to give a talk in front of a big group, than necessarily spend one-on-one time getting coffee with a stranger. That may be a good intro for people you want to get to know on your network. They might not necessarily dedicate the time to sitting down with you, but if you ask them to sit down with 20 people or 50 people or 100, at least at that point, it's worth their time to get a lot of questions answered or to talk about their product or their company. You can always follow up after the fact to try and get that coffee. Newsletters are also a great opportunity to create a following. Let's say you had an interest in getting a job and how technology can be used for good and that's pretty much all you knew about your next career area. You might decide to create a weekly newsletter that covers some of the startups that are going after this. You can reach out to a bunch of people who might have an interest in this space and say, "hey, I'm going to do the work and some of the legwork to cover this particular area and to see what's going on and maybe do an interviewer or two and keep people informed." I started a newsletter about eight years ago. Now it has over 13 thousand people in the New York tech community. Little by little, each month, more people signed up for this newsletter about what events were going on in the industry or what news or trends might happen. It didn't take me that much time each week. It's really become my most powerful career tool. Don't underestimate the power of compounding and the ability to grow a network little by little over time. Surveys are also a great tool to get your name out there. Industry surveys get a lot of press and everybody wants to participate in them because they want to figure out where they are in relation to others. If you were thinking about diving into using startup tools for good, you might consider putting out a survey, maybe of non-profit customers and ask them, are they willing to use a startup for some of their core pieces of technology, or what problems do they need solved? Maybe you might survey a bunch of startups that have social missions and ask them what their biggest challenges are. Putting out a state of the industry survey. It's something that can build a lot of press mentions and really useful to a lot of people. Frankly, for the amount of buzz that can get, they don't take a lot of work. These are all a couple of ways that you might consider getting your name out there by being someone who contributes information to the industry. More so than as somebody who's necessarily the expert themselves. All you're doing is gathering and reprocessing and designing information so that it can be useful to others. 9. Define Success and Measure Outcomes: It's funny. As I was recording these videos, a friend of mine called me up asking for some advice on salary negotiations with a start-up that he was speaking to. It couldn't have been more time point. Here's the advice that I gave him. More so than anything else. You want to work with people that you trust and you feel are transparent about their situation. Maybe the company that you're going to work for, frankly doesn't have a lot of money. If they let you know and you're willing to take that risk, that's fine. But any startup that hires you should be willing to do what it takes to convince you that they're not trying to get one over on you. Maybe the salary is low, but everyone at the company is taking a low salary until they hit a certain milestone. If that's the kind of risks that you're up for, it's fine. As long as they're being fair. There's a difference between being fair with everyone and trying to take advantage of one individual person. Make sure they're transparent and honest and convince you that they're dealing with you in the same way they're dealing with everybody else. In fact, one of the things that I tell the startups that I work with is that they should be setting a budget and figuring out how much they're going to pay for a specific level of expertise and a specific job, well before they talk to individual people. This is how they get around. This is how you can get around biases that happen in the hiring process. Don't pick a salary based on the person sitting across the table from you. Pick a salary based on what the market is paying for that particular job and decide what that salary range is going to be before you even talk to any of the candidates. Know your own personal limits. The reality is, we all have a particular bar of what we need to make year in and year out to keep us happy. I don't necessarily mean what's the absolute minimum you can survive on. I'm talking about, if you like to go to the gym or every now and then you like to go to a nice restaurant, or you have a mortgage payment and you have kids or anything that is really important to you, then you're not willing to sacrifice or the sacrifice would really make you unhappy. Companies should not expect you to go below that bar. Frankly, if they don't have the budget to pay you that salary, there might be a difference between your risk tolerance and the stage of the company. That's an important signal. Because going beneath that bar is going to create a lot of unhappiness in your life, it's going to make you a less productive employee and it's going to make the whole situation probably not work out. It's important to know what you really need to go into your work environment stress-free. That's a number that you shouldn't take less than. In terms of asking about salary, you should be okay asking about what kind of budget a company has and how they're funded. In particular, how many months they're funded to? What kind of milestones they need to get to the next round and how confident they are? Do they have enough funding to get there? You don't want to a company three months in, telling you that they need to cut your salary because it looks like it's going to take longer or some financing didn't come through that they hoped. You want to make sure that they have a well-thought out plan, that has a little bit of an extra buffer, so they know that they can hire who they need and actually get their paying relatively close to market salaries. Some companies frankly, don't pay market salaries, but what they make up for it, is they make up for it in equity. Keep in mind the chances that any of this equity is going to be worth something in the future. But that might be a trade-off you're willing to make. In fact, you may be in a position to take less salary in exchange for more equity. That's fine if that's a trade-off that you're comfortable making. The other key aspect of actually closing the deal and getting this job is to make sure all are on the same page about what success looks like. Too often people who go to work at startup companies are there for six months and things aren't working out because no one actually had an agreed upon goal as to what success looked like. You think you're working really hard and actually the company had really, really misguided expectations as to what was even possible in this position. You need to get that out of the way first. You should sit down with an employer and say, "Okay, based on this level of milestone, maybe it's three months or six months or 12 months, here's what I think I can accomplish. I want to make sure that everyone's on the same page that if we get there." Of course you're going to blow through all of those goals, everybody agrees on. That's a good definition of success. 10. Conclusion: Thanks for making it all the way through this class. I hope it was useful to you and I wish you the best of luck in your attempts at joining the startup community because I know that we need as many talented people as we can get participating in these companies. Let's recap what we went through. Remember the hard part about navigating the startup world is mapping it all out and you did that with the conference project. Now you have a good sense of who are the movers and shakers and influencers and the doers in your specified area of interest and you figured out who they were, what they're talking about, what their challenges are, and some of the trends going through the ecosystem. You put together a specific description of what you can offer a startup when you thought about being a consultant, you thought about short-term projects, longer-term projects and you really focused on the kinds of deliverables that you could offer a company, which also helps them figure out what they should even be looking for from this position. You thought about ways to project yourself as a leader. Even if that just means convening other people who are already leaders by running events or by working on newsletters, or even maybe thinking about doing a podcast, which is something I didn't mention before, but certainly become very popular. Most importantly, I talked about making sure that you don't make too many concessions for joining an early-stage startup. You have minimum levels of compensation and normalcy in a work environment that you need to operate in a stress-free way. Well, maybe not completely stress-free because obviously there's a lot of pressure working a start-up, but you don't need the extra stress of not being able to pay your rent or just having really unusual aspects to add it to the difficulty of a work environment. It's really important to know that company cares about your well-being as an employee while you're trying to do your best work. So I wish you the best of luck. Feel free to reach out at any time. You can find me on Twitter at CEONYC. Happens to be my initials in the city I live in. Or you can follow my blog at this is going to be, or you also find a link to my weekly newsletter that goes out to the New York tech community, thanks and good luck.