Underdog.io Guide to Landing a Startup Job

September 14, 2022
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In the past ten years, interest in tech companies and startups has grown dramatically. According to the fund data website Pitchbook, venture capital funds raised about $225B in 2019 and almost $300 billion in 2020, versus just $50B in 2010. Tech IPOs get top headline placement in mainstream newspapers. As a result, it seems to us that workers are more interested than ever in the startup rocket ship dream—a tiny team that grows at a rapid clip and then showers its successes upon those lucky (or brave) enough to get onboard early.

Even though, statistically speaking, it’s not very likely that you’ll ever make any real money from equity in a tiny startup, we talk to candidates all the time who say that it’s not just the stake, it’s the culture that draws them in. Long hours, a fast pace, and few resources create opportunities to tackle all kinds of new challenges. Add in a constitutional willingness to try new things, like basing tech on esoteric frameworks or executing ambitious one-person marketing strategies with sprawling automation and programmatic ad spends, and you have what a certain kind of driven, risk-tolerant, (usually young) person is looking for.

So, you’re looking to try something new—how do you land that startup dream job? In this guide, we’ll touch on all the basics you need to know, from resume best practices to visa information and equity terms (and how it’s all different from working at a big, established company).

What’s working at a startup like?

Uncertainty and urgency

Every startup is a gamble. Most go like this: a few people with spare time and a healthy dose of insanity decide to build something out of nothing—a college networking webapp, a way to let strangers rent your living room for a night, a new business model for the taxi industry. After a few months, they decide they have vetted the idea well enough to lean into it. They quit their day jobs or drop out of Harvard, maybe raise a small amount of money from their networks, and get to work trying to make that something out of nothing into something huge out of nowhere. And that’s where you come in.

Startups typically make their first hires after their first significant round of funding. From that point the company either continuously grows until it exits or fails. The atmosphere will be pretty different for employee #1 and employee #10, and the 50th hire will likely be walking into a fully-fledged company with an HR department, a beer fridge, and a company swag package sitting on their desk, but the mood will largely be the same: it’s go time, and it’s do or die.

Risk and reward

Startup employees (especially in the very, very early days) generally can’t expect the salaries that they might be able to earn at a well-established company because startups are usually cash-strapped and running as lean as possible. Instead, to supplement cash compensation, startups traditionally offer their employees equity packages—usually either shares of common stock or stock options that permit grantees to purchase common stock at specific times for a set cost-per-share. The idea is that a startup’s high-growth trajectory should drive the value of the shares up significantly over time, allowing employees to recoup their foregone wages or maybe even net a big windfall of cash at an IPO or an acquisition.

In addition to equity grants, very-early-stage startup employees can expect that their cash compensation will increase according to the startup’s ability to pay (either from fundraising or from revenue growth). It’s not uncommon for the initial hires—especially engineers—to negotiate these planned salary increases ahead of time.

Culture and camaraderie

Because the atmosphere at any startup is high-pressure, the relationships teams form can lead to either significant interpersonal friction or unusually tight bonds among coworkers. You’re in the trenches together, facing an uncertain future shoulder-to-shoulder. The hours are long, the stakes are high, and resources are scarce. As a result, startups are extremely careful to hire only when they feel like the candidate is a great fit for the team. For startup employees, though, the bonds they make with coworkers can be some of the strongest they’ll make in their entire careers.

If you’re still not sure if a startup job is right for you, check out Pros and Cons of Working at a Startup.

Where can I find startup jobs?

Startup jobs are a little harder to find than jobs at larger corporate companies, partially because posting jobs anywhere other than your own website generally costs money, and money is one of the scarcest resources at a tiny company. To make sure you’re hearing about all the opportunities that match your skills, interests, and ambitions, we recommend using a variety of sources.

Your network

One of the best places to look for opportunities at startups, especially if you’re already in the startup world, is your own network of connections—both professional and casual. If you’re able to be open about your job search, a post on LinkedIn might let contacts and former coworkers know you’re on the lookout for a chance to get involved in something early. Your alma mater might have an alumni forum full of people with whom you have something in common who are eager to help one of their own. A friend might have a friend who knows something you don’t. In all of these cases, you’ll have a significant asset: a connection to the founder or hiring manager. Asking around is a great way to surface chances that come with the significant advantage of a warm introduction.

If you don’t know anyone who knows anyone, there’s still good news here: people in the startup community love to meet each other, and tend to ascribe a lot of value to delivering or creating value for each other as acts of goodwill and relationship-building. In most places where startups take root, there are corresponding rafts of networking events, such as pitch nights, happy hours, demo days, and Meetups, that exist largely to facilitate connections between people running or working at startups. Go to a few, strike up some conversations, and see who you meet. Even if you don’t hear about an opportunity on the spot, you’ll be starting conversations that could lead to connections down the road.


Of course, there are innumerable places to find startup jobs on the internet. One of the most popular place to find job postings is Angel List, and there are also city-specific sites, like Built In NYC and Built in SF. While you can find some on LinkedIn and the bigger job posting aggregators, such as Indeed and Glassdoor, those sites are of course less focused on startups and therefore less likely to be a hiring startup’s first thought for places to find candidates.

You can also let the jobs find you—Underdog.io connects startup job candidates of all disciplines with great companies hiring in NYC and San Francisco, and engineers have additional options (like Hired, Vettery, and Triplebyte) that work the same way but focus on developers.

A third option is to haunt local startup news sites for press releases about fundraising. A fundraising round is usually a trigger for a round of new hires, so companies that just raised money are likely to have new jobs on their websites, even if they haven’t yet sprung for postings on job sites.

Let hiring managers and founders at the best startups in NYC and San Francisco find you. Join Underdog.io in less than 60 seconds.
Optimize your resume for startups

Reshuffle your resume to appeal to startups

Startups have different hiring priorities from larger, more “corporate” companies. As you’ve heard before, it’s important to tailor your resume to each job opportunity, and startups are no different—but because hiring into a very small team means each new member can have a huge impact, startups hire carefully and select for personality traits as much as they do for skillsets. For best results, take the psychology of a startup founder into account before sending along your resume. Here’s what to keep in mind:

Startups require flexibility and quick ramp-ups

In their earliest days, startups have to do a lot with a little—a go-to-market strategy is no less complicated just because there’s only one marketer. As a result, startups are typically looking for employees who are to some extent generalists within their discipline, such as product managers who are capable of doing some UX research and design as well as comfortable querying a database to examine user behavior. As they grow, they’ll be drilling down for experts to meet their growing needs (and budgets), but the initial hiring phase will be focused on building the bedrock of each department.

Accordingly, they’re looking for people who exhibit a tendency to tackle challenges even when the skills required aren’t solidly in their wheelhouse already. You’ll want to make sure your resume highlights your ability to rise to the occasion even when you haven’t necessarily done exactly what it requires before—show off not just breadth but a willingness to learn on the go.

Focusing on flexibility also gives you a chance to emphasize your specific skills. While startups may not know exactly which tools and technologies they’ll use in the future (and expect you to be able to use them when the need arises), they do know exactly what they use today. The breakneck pace of startup work means hiring managers are looking for people who will be able to commit code or take support calls more or less from day one, and that means you’ll get points for knowing their exact stack ahead of time. Be sure to list the specifics—and if you know their current tooling, put those capabilities first on your list of skills. If they need a developer who knows React and you do, you’ll grab their attention more by including React than just saying you know Javascript.

Be ambitious. Be effective.

The reason flexibility and quick ramp-ups are important is because startups need to move fast. By the same token, they can’t waste a lot of time on tactics that don’t work. The flip side of being specific is demonstrating that what you personally did in past situations was effective. Take a moment to evaluate each bullet point and ask yourself if you can put a quantifiable or impactful result next to the task—don’t take credit for a departmental initiative you didn’t run, but do list out the actual effects of what you did and how it improved the situation.

You’ll also pique interest by showing that you went after problems without being told to do so. Putting some weight on projects you proposed or led will show that you are proactive and ambitious, which are the two most important character traits in a successful startup job candidate. You can also demonstrate these traits by including extracurriculars like side projects and any entrepreneurship experience you may have, even if they don’t seem obviously related to the startup you’re trying to work at. Remember: a startup that wins is one that successfully offers a new solution to an existing problem, so the most effective startup employees are the ones that do the same without being asked to do so.

For examples, templates, and more specific advice for grabbing hiring managers’ attention, check out How to Optimize Your Résumé for Startups.
Tracking your job search

Run an effective job search by tracking each conversation

Even if you’re a hot commodity for startups, you’ll be talking to a number of possible teams before you commit to a position at the one you feel is the best fit—and every single one of those teams is focused on running a startup at the same time as their hiring process. Threads get dropped, calendar reminders get put on silent, and follow-up call dates come and go without a peep. If you want the best shot at the coolest gig, you’ll want to take ownership of the hiring process yourself. Fortunately, it’s pretty easy if you put your organizational ducks in a row.

Track every application

Whenever you send a new resume or cover letter, make sure you write down the date, company name, and role. It’s never a good look to apply twice. Doing so will also give you a good idea of which roles your current skillset seems to fit best in the eyes of hiring managers, which can help you save time (or get an early signal that your resume doesn’t fit the roles you want and needs to be rewritten).

Then, as the conversation progresses, make a note of each interaction. You’ll need these records to effectively manage follow-up. If you have a phone call or an interview and don’t hear back after a couple of weeks, it’s normal and to your advantage to reach back out and see if the company has an updated timeline or if you can provide any additional info to clear up hesitation. Just because a new urgent deadline came up doesn’t mean they don’t want to continue the conversation—they’re just busy with a million other things. Plus, reaching out respectfully shows off your organizational skills as well as your proactive nature.

At each touchpoint, you should take notes. You’ll be having a lot of conversations, so it might be difficult to remember the specifics of the last call when it’s time for the next. If you write down a few reminders about what you talked about, or which questions they asked, you’ll be better prepared to be engaged and confident the next time you speak.

Finally, diligent record-keeping allows you to do some forecasting. If you’re an anxious person, having good data on the pace of each hiring process can help you better anticipate when you can expect a touchpoint or a decision, and when you’re at different stages in multiple conversations, you’ll be able to give your hiring managers better information about when you expect to know which job you want to take.

Use the Underdog.io Job Application Tracker

To save time and help you manage your follow-up, we built a free, easy-to-use spreadsheet tool that can help you keep track of everything in your job search. If you fill in your job hunt data, the tool will also automatically deliver insights and statistics about your effectiveness and timeline.

Keep track the easy way with the Underdog.io Job Application Tracker. Read more and download on Tracking and Organizing Your Job Search.
Understanding startup culture

How do you know if a startup is a good fit?

Each startup has a unique attitude, created organically from the workstyles and values of its founders and team. Because teams are small, each employee can potentially impact dynamics and productivity substantially—and that impact can be good for the team just as easily as it can be disastrous. As a result founders hire cautiously and seek to protect their company’s culture as much as possible. As important as culture is to founders, you should consider it equally important to you.

When you’re interviewing, keep your eyes and ears open for signs that a startup isn’t right for you. If they want you on the team, they’ll be selling the opportunity to you while you market yourself right back to them. That gives you the chance to ask questions and investigate your mutual fitness so you can find a team that will amplify your career (and avoid landing in a role that might create more stress than it’s worth).

Examining work culture

One of the most important factors for your productivity at a startup is a match between the ways you work most effectively and the ways the team expects you too. Some of these considerations are pretty obvious: can you see yourself being comfortable in their office? Does your attitude towards working from home jive with their policies? Are they willing to let you come in early for your cherished 7-10 am silent productivity time, or work later hours if you’re more of a snooze-button kind of person? Does everyone eat at their desks or have lunch together and talk? Identify the factors that make you most comfortable and productive, and find out how well they match up with the way the team works today.

Other considerations may take a little more effort to discover. For example, how does the team view collaboration? If you’re at your best working with other people, but the company strongly values autonomy and teams of one, you’re probably not going to love your tenure onboard. These less explicit features of work culture are on you to investigate. Plans for building departments might make or break the role’s utility to your career trajectory. A heavy reliance on agencies or contractors might not match your tendency to do as much as possible in-house. It’s best to find all of this out before you sign up than find out later and sour your new job honeymoon phase.

Startup social factors

The other side of culture is how the team gets along as people. In a more corporate environment with dress codes and HR, relationships tend to be a little less familiar and a little more professionally proscribed, but at startups, long hours and fridge kegs facilitate a significantly higher degree of interpersonal connection. If your political tendencies, your views on diversity, or your ethical convictions don’t map, that might be an early sign of friction. While we’re not advocating finding a team of people who are exactly like you, you do need to be aware of the ways you might or might not get along with your future coworkers.

As a consequence of the tight-knit, high-touch nature of startup team membership, startups also often develop cultural tendencies that extend outside work hours. If you’re not a drinker but management hits a nearby bar every Wednesday with whoever wants to join, you might find yourself cut out of facetime and drinking-oriented social events. It’s better to know that ahead of time than be passed up for promotion because a colleague has been pitching his ideas over a dry martini for months.

Making sure you’re a culture fit is to mutual benefit. For more discussion of what and how to ask, read How to Vet a Startup’s Culture While Interviewing.
Securing great references

Ensure that you get great references

At the end of the interview process, most hiring managers will ask you to provide references who can vouch for your character and prior work. Not everyone approaches these conversations the same way, and many people simply verify history and ask for red flags. This approach is much less common among founders and hiring managers—they’re significantly invested in making sure that a potential hire is a good hire, and in many cases would rather hold off on making an offer than end up with a potentially problematic employee.

Pick references that sell you

Your references are a powerful tool—you want to pick people who can really make the case for you. If you choose a higher-up who isn’t super familiar with your work, they may not be able to answer the kinds of in-depth questions founders might ask. On the other hand, if you choose someone who saw a lot of your work but wasn’t exposed to your strategic contributions, they may undersell your proactive tendencies and creative thinking.

It’s a delicate balance, but by reference check time you should be aware of what the hiring manager thinks about you and what they think is important. Optimize for a reference (or a mix of references) who can not only reassure them about anything they might perceive as a gap in your capabilities but actively reinforce your claims about your strengths and growth potential.

Ask nicely and listen

While references are a professional courtesy most people are willing to extend, you’ll get the best results by treating the process of asking for one as a project in ingratiating yourself to the reference provider. You’re asking for a favor, so you need to make the process as easy, as unobtrusive, and as respectful as possible.

Providing the reference with enough context and information about the job and the hiring manager is key to making sure they’re prepared to hit all the high notes. If you have something you specifically think the hiring manager will bring up, feel free to mention that so the reference has time to refresh their memory before the call. During this phase, you should also get a sense of how enthusiastic the reference will be. If they have any hesitations, be sensitive to the question of whether or not it’s worth calling in the favor. A lukewarm reference isn’t going to make the sale.

Above all, be polite and easy to work with. A reference takes time out of their day to talk to you and does it again to talk to the hiring manager, so try to make the experience as pleasant as possible. If all goes well, you’ll have a powerful ally in your quest for a startup job offer.

For a more in-depth discussion about how to secure a glowing reference, check out Picking the Best Startup Job References.
Startup equity basics

Understanding startup equity

Startups, like all companies, have owners. Over time, in an investor-backed startup, most of the owners will be investors, but in the early days, the owners are usually mostly the founders and some employees. This ownership is represented by “shares,” where each one is a tiny fraction of the overall ownership. This is called equity. Being generally cash-strapped, startups traditionally offer employees some equity in lieu of more competitive salaries.

Common stock and stock options

In most cases, U.S. startups are either LLCs or Delaware C-Corporations. LLCs are each unique, so we’ll limit this discussion to C-Corps. In a C-Corp, shares exist in a few forms, called “classes,” with the founders typically having “common stock” and the investors typically receiving “preferred stock.” While there are certainly nuances, like voting rights, the main difference between the two as far as this discussion is concerned is that, at an exit, the preferred shares will typically be paid out first.

Employees don’t usually get common stock, though—their grants are generally going to be “stock options,” which represent the right to buy common stock at specific times at a price-per-share set at the time of the grant. The idea is that, if shares in the company become more expensive over time, an option-holder can eventually buy their common stock shares for significantly less than they are worth, turning a profit.

Vesting schedules for employees

One of the main reasons startups grant equity (aside from it being a less liquid and therefore momentarily cheaper form of compensation than cash) is to incentivize their employees to work for the long-term value of the company, since better performance will increase the value of the employees’ shares. To make sure that value only accrues to employees who participate over that period of time, options (and most common stock grants) come with a “vesting schedule,” which describes how the options become available to the employee.

By far the most typical vesting schedule is four years with a one-year cliff. On this schedule, the employee receives no options for the first year, then ¼ all at once after one year, and then the next 3/4s on a regular schedule over the next three years.

Valuing your equity grant

How do you know what an equity grant is worth? In general, you can’t—and in most cases, it won’t ever be worth anything, because most startups fail entirely, and of those that do successfully exit, few end up distributing significant amounts to the option-holders at the bottom of the cap table. So, unless you’re looking at a very significant (2%+) equity stake as part of your compensation, you should consider the equity to be more like a free lottery ticket than an investment.

For more discussion of shares, vesting, options, and dilution, check out Startup Equity Basics for Job Seekers.

How to negotiate your salary

Typically, in startup world, offers are made in conversation—you’ll receive (or schedule) a call, and the hiring manager will go over the equity, benefits, and salary components of the package with you. You’ll have the opportunity to ask questions at that point, and you can of course simply accept or decline the offer, but in most cases it’s to your advantage to take a day or two to consider.

As you think about the offer, do a little bit of reflection and investigation to make sure the compensation feels fair to you, and understand how you would adjust it based on your own understanding of your value as an employee. Then, if you think the offer needs adjustment before you’d be comfortable accepting it, you’ll have an opportunity to counteroffer the company. But how do you know what’s reasonable to expect?

Understand your salary range

If you have multiple offers on the table, it’s fairly easy to see which companies are coming in on the low side (and which really, really want you on board), but most job candidates don’t have this luxury—offers come on staggered schedules, or they simply only have one. In these cases, the employee might need to turn to other sources to compare.

Today, most job boards have localized salary calculators available by job title. If your city has a startup-focused job site, you can check there to see what employees with similar skillsets make at comparable companies. If not, you can manually find a group of companies at a similar stage in your area and see if they have salary data available at a site like Glassdoor.

Remembering that startups can typically afford to pay a little less than larger, more established companies, you can also check salaries in your area for similar job titles across the whole local job market, but due to typical discrepancies in title vs. experience between corporate and startup world, useful data from a non-startup source might be hard to find.

Developing a counteroffer

If your research (or other offers) indicate that an offer you would otherwise accept is too low, you can ask for more. Again, the easiest way to do so is simply to point out that you have higher offers, but if you don’t have others, you’ll need to make your case on the basis of how much value you can create for the company.

The two pieces of the offer up for negotiation are typically equity and cash. Most of the time, you’ll have to pick one of these to increase—and that’s a matter of risk tolerance. If you really think the startup is destined for super-high exits, it’s sometimes easier to ask for more equity, and (if you’re negotiating with the founders) their willingness or hesitance to give up more basis points will tell you a lot about their own confidence in their venture. On the other hand, when budgets are really tight, salary increases might feel like a more expensive concession to the company.

You should understand that your counteroffer will probably end in a compromise. If it doesn’t, you may not have asked for enough (although it’s probably too late), but if it’s simply a flat “no,” you need to know ahead of time whether that’s make-or-break for you. At a “no,” which is most typically due to budget concerns, you can ask for some guarantee that your compensation will be adjusted at a specific milestone (like the next fundraise).

At the end of this negotiation, if you have multiple offers, you’ll need to go back to everyone and accept or decline. It’s best to make this process as quick as you can, since startups only hire when they have real needs and will need to move on to another candidate.

Overview of US work visas

If you’re looking for a startup job in the United States but you aren’t a US citizen, you’ll need to contend with immigration regulations. To be eligible to work in the US as a foreign citizen, you’ll need to secure either a green card or (more likely) a work visa. These come in many flavors, but they all have some commonalities: they take awhile to secure, they’re fairly difficult to receive, and you’ll need help from a specialized lawyer.

Types of US visas

Depending on where you’re moving from, how long you intend to stay, and what you’ll be doing in the States, there might be one or more visas available to you:

  • E-3 visa for Australians: quick and easy, but limited to Australian citizens only
  • TN visa for Canadians and Mexicans: limited to whitelisted professions
  • H-1B visa for degree holders: the most common type, but capped at 65,000 per year
  • L-1 visas for inter-company transfers: only available to employees of at least a year
  • J-1 visa for internships: only available for interns
  • F-1 visa for students: can optionally include a year of work authorization
  • O-1 visa for extraordinary ability: the most difficult to qualify for

Your choice of visa application will be a decision you make with your chosen immigration attorney or the hiring company’s lawyer, but it helps to understand all the options. In addition, there are variants and exemptions for requirements in some cases, but you won’t be making the decision in a vacuum—your lawyer will guide you through the possibilities.

Do startups sponsor H-1B candidates?

The most commonly sought visa is the H-1B, which is a straightforward work-authorized visa good for 3-6 years that can come with a path to a green card for permanent residency. An H-1B visa (like most visas) requires sponsorship from a company, and is therefore contingent on a job offer—in other words, the company has to be willing to spend the time and money to help you apply for a visa you may not even receive.

Startups typically have to move too fast to be able to tolerate the effort and time involved in making a hire and then waiting months for the candidate to move through the very slow H-1B process without even a guarantee that their application will be approved. If you’re lucky, pay for expedited processing, and manage to time the job offer with the brief window each year that applications are open, you may be able to secure one, but the sheer number of caveats involved tend to scare away startups. Most H-1Bs are sponsored by larger, more established companies for this reason.

Interested in moving to the United States for work? Read more about visas on our Engineer’s Guide to US Visas.

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