How to Join a Startup

Once you’ve figured out which startup you want to join, you can follow a process to maximize your odds of getting hired. 

• ‍Note: If you don't know which startup, read that part first.

Before we dive into the tactics, there's some key advice from Anthony Chen, employee #1 at Flexport.

“When you’re boarding a rocketship that you believe will be worth billions of dollars, don’t ask which seat.”

Most candidates apply using the job board on the startup’s website and waiting patiently. That's a big mistake. At a busy startup, there's so much chaos that your application can easily slip through the cracks. Best case: they read it, but it doesn’t lead to a distinct first impression of you. 

In the early days, founders want team members who will take massive action to get things done. You can show that you're that type of person. 

How can you show you’re doing the job already before getting the job? 

A couple examples come to mind:

• Marketing candidate comes in with a list of channels to reach the market, a list of potential customers, and a pre-written sequence. 

• Engineering candidate shares a fully fleshed out product idea. They can describe the problem it solves, how they would go about building it, and the timeline they could expect. They even have rough diagrams of how the UI and UX should look.

If you aren't willing to invest this much effort into the process, maybe this company isn't the right fit for you. Find a place that makes you feel so excited that you would want to put in this kind of effort.

Once you’re ready to make an outstanding first impression, it’s time to contact the startup.

First, find the cofounder who manages hiring. It's the CEO for most roles, or the CTO for the product and engineering roles.

I recommend finding their direct email address. Then, send an email like this that (1) expresses personalized interest, and (2) introduces you as a candidate.

Hi Adam,

Owner looks cool! I read your story about how it started with you helping your mom’s business. Then that idea evolved into the all-in-one platform for restaurant’s online presence (like Shopify for restaurants). I would love to learn more about where you’re going from here and connect.

My name is Eric and I’m a frontend software engineer. I work in React primarily. I’ve spent the last X years as an engineer at Facebook, responsible for building our mobile web content tools. Now I’m looking to make an impact at an early stage company. 

Any interest in an introductory call?

Cheers,
Eric Koslow

Short, relevant, and to the point. 

If you aren’t an experienced tech industry professional, you can change the second paragraph to something like this:

My name is Eric and I’m a generalist passionate about helping restaurant owners because I grew up in the industry. I just graduated from Babson College and I’m looking to join a startup where I can make an impact. I hustle hard, get things done quickly, and am happy to wear many hats if it seems to be a mutual fit.

Obviously, adjust the message to be in your own words so that it feels authentic.

Receiving this email from a strong candidate is every founder’s dream come true. Seriously.

You will very often earn a meeting.

This type of message shows that you:

• Hustle hard and take initiative
• Are passionate about the company
• Have strong communication skills

Sometimes, you won’t get a response after your first email.

Don’t give up. Don’t take it personally. Startup founders are some of the busiest and most bombarded people on planet earth. They live in chaos.

If you don’t get a response within 48 hours:

• Keep following up on your email. 
• Add multiple people from the company on Linkedin and Twitter. 
• Follow up on other channels. 

They’ll notice you over time. It will make an even more positive impression. What startups need, more than anything, is resilient people who get stuff done at all costs. Shameless persistence is part of that.

“Don’t just send 1 email. Follow up on your email, add multiple people on LinkedIn and Twitter, follow up on other channels (like LinkedIn message). Engage with them on social media. Founders are busy. But they’ll notice you the third or fourth time, and startups want to hire persistent people – so show that.” - Kyle Norton

Once you get that meeting, how do you make a good first impression? 

‍

How To Nail A Startup Interview

‍

Start with good energy.

This should be easy. But a shocking number of candidates get this wrong.

To nail this, start off with a smile and greeting them by name. Ask them how they are doing. 

• “Hey Adam!” 
• “How are you?”
• “Doing great, thanks! Excited to learn more about you and Owner!”

Almost every good interview starts like that.

If you feel nervous, you can choose to instead interpret your nervousness as excitement. 

Some mindset points that can help: 

• Getting hired is your goal, but they need you more than you need them.
• It’s incredibly hard to find dedicated and motivated people. Startups generally hire for high potential, not high experience. If you’ve read this far and are executing on this advice, you’re one of them!
• Remember: early stage founders spend serious time searching to find people like you. Recruiting and retaining excellent talent is the most important thing they do.

After you’ve started the conversation in a friendly way, start by flipping the script. Ask to learn about them and the company.‍

You should be interviewing them just as much as they interview you.

Leading with your questions makes it clear that you value yourself. It will set you apart from other candidates. It also changes the dynamic between you, setting you up as an equal, not a subordinate.

This line works well:

“I would love to start by learning more about you and Owner, and then I would be happy to share more about myself. Does that work?” 

This is important. Most candidates just sit silently and wait to be asked questions. It’s always a positive signal when candidates come in with a set of thoughtful questions and are excited to get to know our business.

If a candidate is thoughtful in preparing for an interview, I assume that they'll be even more thoughtful in the role.

Good questions to ask a founder in an interview:

• Can you tell me more about your vision? 
• I noticed you said you were expanding into reservations in your TechCrunch interview. What are other product expansions you see coming?
• How does Owner fit into the competitive landscape of other restaurant tech companies? 
• How are you thinking about building the team? 
• What are your top priorities as CEO? 
• How does Owner become a ten-billion-dollar company? 
• I noticed you were building Minecraft servers before founding Owner. Can you tell me more about that and your life leading up to Owner?
• What are the most important cultural things you look for in people you hire? 

That last question is key for two reasons.

First, it gives you a sense of the culture they’re trying to build. Now you can judge whether that culture is aligned with you.

Second, it gives you the cheat codes: now you know what to emphasize in your answers to their questions. They've shared, upfront, what they're listening for.

Bad questions to ask a founder in an interview:

• What does the product do? 

It is a very bad sign when a candidate clearly doesn’t know what the product does. It signals that they aren’t resourceful enough to use Google or check our website. If that's the case, they’ll be doomed in a startup. I instantly end interviews when candidates ask this. 

Make sure you have a good idea of what the product does.

• When was the company founded? 

This can also almost always be found in a 10-second google search, or by looking at the LinkedIn profiles of the founders. If you ask this, it signals that you're unprepared.

• What is work/life balance at the company like? How many PTO days do employees get?

Early startup teams have to be extremely hardworking and dedicated to beat the odds. It’s a red flag in my mind when candidates seem fixated on work/life balance or taking time off from the first interview.

Next—if you really want to knock the socks off the interviewer—come prepared with a solution to a problem the business is facing. 

For example, if you’re a marketer, all early stage startups struggle to grow in a scalable way. You can help solve that problem by researching advertising channels where you could target new customers.

Or, if you’re a generalist, all early stage startups struggle with building the early team. It would be a dream come true if you came to the interview with a list of highly capable people and a written-out email sequence to get their attention.

You can get creative. Early stage startups struggle with all sorts of problems.

Founders appreciate it when you put effort into helping the business solve a major problem.

It also activates our innate desire to reciprocate. When somebody does something good for us, we want to return the favor. When somebody takes an interest in us, we reciprocate with a high level of interest in them.

In interviewing more than 1,000 candidates, I’ve had about 10 show up having brought solutions to problems (1%).

I wanted to hire each of them instantly on the spot.

Few candidates:

• Embody the right mindset of confidence, clarity, and valuing themselves.
• Understand the business, the product, and the market that a startup is serving.
• Prepare materials on how to improve the business.

Initiative is so important in early startup team members, yet so rare. When founders see it, it makes a great impression.

Know the customer, product, and market context.

It doesn’t take much to learn the basics of an industry. But it's an amazing signal to the founders.

For example, imagine you were interviewing at my company, Owner. 

Our homepage shows that we’re the all-in-one platform that thousands of restaurant owners use to power their digital presence. 

Imagine you also come prepared knowing why customers buy, the size of the market, and the market status quo.

You'll have differentiated yourself from every other candidate.

You’ll be showing that you do well even when you don’t have clear instructions. You figure stuff out.

You can add in these insights in the interview conversations to show the founders just how much you know about the business. It demonstrates how much of an asset you would be.

Now...

Imagine you prepared for the interview. You got it. You started it with good energy. And you asked thoughtful questions.

At some point, the interviewer will begin to ask YOU questions.

If you feel nervous, choose to interpret it as excitement!

Remember: they need you more than you need them. You would be making a major investment (of years of your life) by deciding to join. Early stage startups live or die by the quality of their team.

More interview tips to maximize your chances of getting hired: 

• Take a short pause after every question, to figure out what you want to say. Don’t just dive into a ramble.
• Be perfectly prepared for the cliché interview questions. (Strengths & weaknesses, major mistake, what you learned, your experience so far).
• Answer each question in less than 2 minutes. You don’t have to share every detail in your initial response. Holding back, a little bit, gives your interviewer the ability to engage by asking follow-up questions.

The more concise you are, the more balanced the talk ratio will be throughout the call. Balanced talk time makes the rapport feel better. Founders consistently say that the best candidate interviews don’t feel like interviews. They feel like conversations with a friend.

When you chat with a friend, you casually exchange ideas. It's a back-and-forth. You don’t go on monologues.

• When a candidate rambles on for minutes at every question, it’s a red flag that signals foggy thinking. I start to dislike the idea of working with them. Their long responses block the ability to have a productive conversation.

Also, if you followed the advice above, you got some of the cheat codes for the interview:

• You know what they look for in candidates—so highlight your relevant strengths.
• You know their vision—so share how you can use your skills to contribute.

After you’ve nailed the first interview, you’ll likely be asked to interview with a few more people. Repeat the above steps for those interviews. Research the interviewer going in. The more you know about them, the better.

Lead by asking questions and being prepared, then use that preparation to have a productive dialogue about the business. If you do that, you will crush it 10 out of 10 times.

There’s one more step after crushing the interview, essential to joining a startup…

Negotiating Startup Compensation 

At some point, you may be asked about your comp expectations.

It’s important that you come ready to discuss comp in all conversations.

If you’re asked in your first conversation:

“I would love to learn more about you and Owner, what the role looks like, and whether we each think it’s a fit, before discussing what fair comp should look like.”

Why? For the same reason sales calls don’t start by sharing the price. The best strategy is to let them fall in love with you first, and understand the value you can bring. Then, you can share how much it costs, so they can make a complete decision.

Plus, it gives you additional leverage in negotiation. By the time you discuss cost, they'll really want you on the team.

Just know that an early-stage startup will not pay you the same amount of cash as a big tech company. You make up for it—if you truly believe in the startup and the founders—by getting equity.

Once you’re asked about comp towards the end of the process, or presented with a package, this is how I recommend starting the dialogue:

• I would love to join Owner because I think we’re aligned in terms of values, I could be very helpful on the journey, and I love your vision and mission.
• According to Pave.com, the average comp for an engineer at a startup of this stage is $132,500 and 1.15% of equity vesting over 4 years. That’s what I think is fair.

They may say, "X is an above-average startup with above-average potential and above-average investors." 

You can respond by saying you’re an above-average team member. 

You can even add that both salary and equity vest, and they can hold you to a high standard of performance given the high compensation.

Those responses will impress the founder, because you’ve prepared so well and know your worth. If the founder is too short-sighted to offer market compensation to top talent, then it might be a sign to go find a startup which would value you fairly.

If they push back against cash comp, you have a perfect reason to ask for more equity. Don’t let them push back equity comp beneath these ranges, or you will drastically limit your upside.

I’ve pulled some benchmarks by Pave to give you a better sense. I recommend using the tool personally, or another tool like Levels or Built in. These will give you a sense of fair comp before you talk about it with the founders.

The other thing to negotiate related to compensation is vesting schedule. 

In startups, equity compensation is granted in the form of stock options. 

It’s offered in terms of share count rather than % of the company.

Stock options usually vest monthly on a 4-year schedule and a 1-year cliff. This means:

• At the end of the first year, you vest 25% of your grant.
• Then you vest 2.083% of your stock options monthly until you hit 100%, 4 years in.

Because of the 4-year vesting and 1-year cliff, it’s important to only join startups where you can see yourself succeeding for at least 4 years. Otherwise, a huge part of your compensation package will never be earned.

PRO TIP:

‍If you’re asking for more equity than the founders seem comfortable with, you have a potential lever. You can offer to vest it over 5 or 6 years, rather than 4. This might seem like it would just decrease your rate of compensation. But remember: in the case of a liquidation event (like the startup being acquired), stock options tend to become fully vested. A longer vesting period also makes you look even stronger as a candidate, because it shows you’re long-term oriented.

I’ve heard over a dozen stories about early employees leaving a startup before the 1-year cliff, securing zero equity. They end up regretting it, realizing they left millions in equity on the table.

Long time horizons are rewarded in startups.

Now, imagine you’ve found a startup you really believe in. You've impressed the team. You've negotiated a fair compensation package. How do you now succeed at the startup? 

Succeeding As A Founding Startup Employee

Now that you’ve joined a startup that you believe in, how do you make sure you succeed? 

1. Figure out the company’s top priorities.
2. Align with your manager on your plan for contributing to them.
3. Execute your plan, while ruthlessly prioritizing.
4. Follow these pro tips to ensure you maximize your collaborations.

Before planning what you will do, figure out what the startup needs most. You can ask the CEO and other leaders on your team. But it's best to also include conversations with customers (current or future). That way, you can understand the nuances of the market that you’re building the company for.

Anthony Chen, employee #1 at Flexport, had this brilliant advice:

• “The most important thing to do first is to understand the real pain points of the business. Get your hands as deep as possible in customer relations, product, and business problems. That enables you to execute as efficiently and autonomously as possible, because in a small company, nobody has time to micromanage you.”
• “As you’re executing, create systems for yourself and others to follow as you scale.”

That brings us to step 1.

<num-list>1<num-list> Figure out the company’s top priorities. 

Until a startup has product/market fit, PMF is the #1, #2, and #3 priority of every single person in the company. This means: talk to customers and iterate on the product for them, until PMF is achieved. 

How do you know whether a startup has product/market fit? 

Marc Andreessen describes it as feeling like the product is being pulled out of the startup by the market. Sam Altman says, "When a product is so good that customers spontaneously tell their friends about it, you know you've got product/market fit."

Until a startup has product-market fit, the top 3 priorities are always:

• Find product/market fit by constantly talking to customers and iterating product.
• Find product/market fit by constantly talking to customers and iterating product.
• Find product/market fit by constantly talking to customers and iterating product.

Once a startup has product-market fit, the priorities tend to be:

• De-risking the business by deepening product/market fit and recruiting an A+ team 
• Finding scalable and repeatable growth channels to facilitate customer acquisition 
• Building systems to drive better customer experiences and smoother operations

After you’ve identified the company’s top priorities, it’s important to create a plan for how you can contribute to them. Early stage startups always lack structure and planning. 

Plans in startups are mostly useless, since things change so quickly. But the process of planning is extremely valuable. It brings clarity to your execution.

<num-list>2<num-list> Create a success plan for yourself. 

The best plan I’ve seen is the scorecard-turned 30/60/90 day plan.

Here’s an example from our SVP of Customer Success, who crushed it in her first 90 days. She had great clarity on what the business needed, and exactly how she could contribute.

• What is the company’s mission, and how does my role contribute to it? 

Owner.com’s mission is to arm owners to take on their goliaths. We're starting with restaurants. We help local business owners fight back against Goliath-sized corporations, like GrubHub. These goliaths are destroying their businesses. We arm smaller businesses for success with our all-in-one system for profitable growth. It powers online ordering, marketing automation, websites, recruiting, and more. It's like Shopify + HubSpot, specifically for restaurants.

The purpose of the SVP Customer Success’s is to build a world-class customer experience immediately after owners sign up. She achieves this by managing, leading, and recruiting the customer success teams.

• What are my top 3 priorities, in order of importance? 

1. Customers must retain at a rate of 98%+ monthly
2. Customers must launch within 3 days of signing up, on average
3. Team must be made of intimidatingly good people in every single CS position, even at scale. High intelligence, friendliness, and high drive must be the standard.

• What will I get done by day 30? What will I get done by day 60? What by day 90? 

By Day 30: Implement a health score system to quantify account activation. Create automations to identify at-risk accounts and help them optimize product success. Define targets for how headcount should ramp to meet CS goals, create a knowledge base for support which details text and videos for FAQs. Own 100 customer relationships personally to better understand exactly how to build systems to help them.

By Day 60: Implement support chat solution. Recruit 2 support specialists, 2 onboarding specialists, and 2 success specialists. Ensure we meet business goals.

By Day 90: Complete implementation of customer success management system. Create accounts receivable collections process. Implement call recording across CS teams for coaching purposes.  Hire 4 support specialists, 4 onboarding managers.

We start with the mission, then the business' priorities, then the candidate's goals for the first 90 days.

Choose goals that are both ambitious and attainable with full effort.

In planning the problems you will solve in 30/60/90, it’s important to differentiate between:

• A Class Problems (high impact, usually high difficulty)
• B Class problems (medium impact, usually medium difficulty)
• C Class problems (low impact, usually low difficulty)

The impact and level of difficulty of a problem are usually correlated. In cases where you find truly high impact problems you can solve that are medium to low difficulty, place those at the top of the list. They produce a disproportionate benefit compared to their cost.

You might feel tempted to focus on the B- and C-class problems, because they are easier to get done and celebrate quick wins. But that’s a mistake. 

Instead, focus on solving A-class problems. Their high difficulty and high impact makes them a major competitive advantage for the company once they're solved. Solving the hardest problems de-risks the business. 

It's like starting a mega game of dominos by knocking down one giant domino. It takes more force to initially knock it down. But that one giant domino knocks down many smaller ones.

Often, the pockets where you can make an impact are in the most unsexy parts of the business.

Here are some places where I’ve noticed many A-class problems, post product/market fit:

• Finding and deepening product/market fit (by talking to customers and iterating product)
• Validating and proving new growth channels (post PMF, startups live on growth)
• Polishing customer success processes increase customer retention and NPS
• Upgrading internal processes and systems to make scaling smoother

For example, imagine you’re joining as an engineer. You may be tempted to dive into building new features as quickly as possible to solve medium-impact problems. It would boost retention and satisfaction. But if you notice an A-class problem with the way the codebase is architected and the startup is post-PMF—that might be a higher priority. It might be worth paying down technical debt before adding features.

Solving that one A Class problem will make solving future B Class problems and C Class problems easier and faster. It will also make recruiting and retaining engineers easier, even if it doesn’t provide a quick win for the business.

The A Class problems in the early days are almost never the things which feel sexy to work on: 

• Getting press for the company
• Doing heavy brand marketing, without clear focus on growth marketing
• Building features you think would be cool, without deeply understanding the customer

Once you’ve:

1. clarified how you can contribute to the company’s mission
2. figured out what the most important problems you can solve for the business are
3. aligned with your manager on a 30/60/90 day plan to set expectations

It’s time to get into execution.

<num-list>3<num-list> Execute your plan.

In startup, there are more fires burning than you have resources or time to put out.

They will all feel important and urgent at first. Many of them could burn down the business if left burning for long enough. 

But some fires do more damage when left burning, and are therefore more urgent.

So it’s critical to focus on putting out the most important, high leverage fires first.

One of the best things I’ve learned from Alex Bard, an outstanding investor and founder, is keeping what he calls a “ruthless prioritization list”.

Here’s how my ruthless prioritization list works:

• Brainstorm the top 20 things you could be working on for the business.
• Rank them in order of importance.
• Focus only on getting the top 3 done at any point in time. Don’t do anything else.

In order to really focus your attention on the top 3, A Class problems, refuse to focus on anything else until they are completed. This laser focus speeds up your rate of execution and makes you more effective in a chaotic environment.

The only advantage that startups have over large companies is their speed of execution. Because they are extremely small and capable teams with clear goals, they can improve way more quickly. But they lose that advantage when they get slowed down executing on countless small things that they could do. Picking the small, low-hanging fruit is a game for big companies—not startups.

<num-list>4<num-list> Remember these tips:

• Create a 30/60/90 for yourself and share it with your manager to set expectations
• Seek out a few pockets (often unsexy) where you can make an impact 
• Build strong relationships. Set weekly 1:1’s with everybody else on the team where you align on priorities, discuss the biggest challenges in the business, and more.
• Take massive initiative on solving a problem. When you see a problem, don’t just tell others about it -- start planning, sharing, and executing potential solutions. 
• Embrace the change -- in your role and in the company.
• Don’t hold on too tightly to your role or title. In early stage startups, those change all the time. Commit yourself to acquiring the skills and role necessary to make the company itself successful. When boarding a rocket ship that you believe will be worth billions of dollars, don’t ask which seat you’re getting.