How to Join a Startup

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

• ‍Note: If you haven’t figured out which startup you want to join, read that part first.

Anthony Chen, employee #1 at Flexport, had important advice to give before we dive in to the tactics.

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

Most candidates make the mistake of applying using the job board on the startup’s website and patiently waiting, but that’s a bad idea. At a busy startup, there is 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 as a candidate. 

What founders are looking for in the early days are team members who will take massive action to get things done, and you can show that you are that type of person here. 

So, how can you show you’re doing the job already before getting the job? 

Some examples that come to mind:

• Marketing candidate who comes prepared with a list of the best channels to reach the market, a lead list of potential customers, and a pre-written sequence. 
• Engineering candidate who prepares by sharing a fully fleshed out product idea, describing the problem it’s solved, how they would go about building it, what timeline they could expect, and rough diagrams of how the UI and UX should look.

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

First, find the cofounder who manages hiring. This will be the CEO for most roles or the CTO for the product and engineering roles.

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

Hi Adam,

Owner looks cool! I read your story about starting by helping your mom’s business, and how that evolved into Owner – building the all-in-one platform for restaurant’s digital 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 and was responsible for building our mobile web content tools. I’ve spent the last X years as an engineer at Facebook, and 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 swap out the paragraph introducing yourself for 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.

It will almost always get you a fast meeting with the cofounder making hiring decisions.

It demonstrates 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, and this will make an even more positive impression. What startups are looking for more than anything is resilient people who get stuff done at all costs, even if it means being shameless in persistence.

“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), and 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

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

‍

How To Nail A Startup Interview

‍

It’s no secret that first impressions matter. 

So it’s important to start with good energy and a good mindset. 

For such an easy one, it’s shocking how many 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!”

Good interviews almost always start with good energy. It sets the tone.

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

Some mindset shifts which can help: 

Getting hired is your goal, but they need you more than you need them.

It’s incredibly hard to find people who are dedicated and motivated. 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 such people!

• 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.

If you’re not willing to invest this type of effort in the process, it could mean that you’re either not a good fit for a startup at this stage or that you don’t want to join that company enough. Find somewhere you feel so excited about that you would want to put this level of effort in.

After you’ve started the conversation in a friendly way, start by flipping the script and asking to learn more 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 and will set you apart from the other candidates that the founder is looking at. It changes the dynamic between you, from a conversation where you are lower to one where you are equals.

So this line could work really 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, because most founders are used to candidates that 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 actually get to know our business. 

If a candidate is that thoughtful about preparing for an interview, I assume that they will be even more thoughtful once they’re in the role itself.

Good questions to ask a founder in an interview:

• Can you tell me more about your vision? 
• I noticed you said X in Y. 
• 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? 
• This is a key question for two reasons: first, it gives you a sense of the culture they’re trying to build and allows you to evaluate whether that’s aligned with you. 
• Second, it gives you the cheat codes on what things to emphasize in your answers because they share what they look for with you upfront.

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. If they aren’t resourceful enough or don’t value their time enough to use Google or check our website before committing to an hour interview, they’re doomed in a startup. I instantly end interviews when candidates ask this. 
• Make sure you Google around and read enough about the company that you have a good idea of exactly what the product does. 
• When was the company founded? 
• This can almost always be found in a 10 second google search, or by looking at the LinkedIn profiles of the founders. Signals that you didn’t prepare if you ask.
• What is work life balance at the company like? How many PTO days do employees get?
• Early startup teams have to be extremely hard working and dedicated to beat the odds, so 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 repeatedly and scale-ably. A solution to that problem might be researching advertising channels where new customers can be targeted and planning out ads to reach them.

Or, if you’re a generalist, another problem all early stage startups struggle with is in building the early team. Coming to the interview with a list of highly capable and relevant people and a written out email sequence for how to get their attention would be a dream come true.

You can get creative with this. Luckily, early stage startups struggle with all sorts of problems – meaning that you can take liberty in the solutions that you suggest. 

The more effort it feels like you put in to helping the business solve a major problem, the more the founders will appreciate it and the better the impression will be.

This also plays on our innate desire to reciprocate as humans. When somebody does something good for us, we like them more and want to return the favor. So when somebody takes an interest in us enough to come prepared to help, we reciprocate that high level of interest in them.

In interviewing over 1,000 candidates now, I’ve only ever had about 10 show up having brought solutions to problems (1%).

I wanted to hire each of them instantly on the spot, just for that. 

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 and yet so rare. When founders see it, it makes a great impression.

Know the customer, product, and market context going in.

It doesn’t take much to learn the basics of the industry that the startup is in, but it is an amazing signal to the founders of the company when you already know the market. 

For example, let’s say you were interviewing at my company, Owner. 

A quick glance at our homepage shows that we’re the all-in-one platform that thousands of restaurant owners use to power their digital presence. 

If you can come prepared knowing why customers buy, what the market size is, and what the market status quo is –– 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, and 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, and to demonstrate how much of an asset you would be. 

• What do customers do before the product? 
• Example: Before Owner, restaurant owners have to cobble together 15 different solutions, paying thousands each month in total, to power their digital presence.
• Why do restaurant owners decide to use the product? [Owner example] 
• Because if they don’t, people don’t order directly from their website. 
• So they lose 25% of each transaction to companies like GrubHub and all of their customer data. Before Owner, they try to cobble together 15 different tools but it’s too time consuming and expensive.
• How big is the market for the product? 
• With this one, you have to assume how much each customer will be worth to the company at scale and then multiply that by the price of the product.
• Example: a quick Google search shows that there’s 400,000 independent restaurants in the United States. Since they’re each worth $1,000/m to Owner, our market size (powering the restaurant's digital presence) in the United States is $48 billion.

So – after you’ve prepared for the interview, started it with good energy, and asked thoughtful questions, the interviewer will flip the script and begin to ask you questions.

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

Remember: they need you more than you need them. It’s you that 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 is asked to figure out what you want to say. Don’t just dive into a ramble.
• Be perfectly prepared for all of the cliche interview questions (strengths / weaknesses, a major mistake you made and what you learned, walk me through your experience so far)
• Answer each question in less than 2 minutes. You don’t have to share every little detail in your initial response. In fact, holding some back gives your interviewer the ability to engage by asking follow-up questions.

The more concise you can be, the more even the talk ratio will be throughout the call and the better rapport will feel. 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 back and forth. You don’t go on monologues for 2+ minutes at a time.

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

Also, if you followed the above advice, 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, it’s likely that you’ll be asked to interview with a few more people in the company. Repeat the above steps for those interviews and research the interviewer going in. The more you can 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 that is essential to joining a startup…

Negotiating Startup Compensation 

At some point in the interview process, you may be asked what your comp expectations are.

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

If you’re asked in your first conversation for comp expectations, this is how I recommend responding:

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

Why? For the same reason why sales calls don’t start by sharing the price.

The best strategy is to let them fall in love with you and understand the value you can bring before sharing how much it costs, so that they can make a complete decision.

Plus – it gives you additional leverage in negotiation because, by the time you discuss cost, they will really want you on the team.

Just know going in that in an early stage startup, you will not be making the same amount of cash as if you joined a big tech company. The way you make up for it (if you truly believe in the startup and the founders) is 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 if you’re interested: 

• I would love to join Owner because I think we’re aligned in terms of values, that I could be very helpful on the journey, and because 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

If they try to refute that by saying that 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 that they can hold you to a high standard of performance given the high compensation level. 

Those responses will both 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, to get a sense of fair comp before having a conversation about it with founders of a startup.

The other thing to negotiate related to compensation is called 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, meaning:

• 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, one potential lever to pull might be to offer to vest it over 5 or 6 years rather than 4. While this seems like it would just decrease your rate of compensation, it’s important to remember that in the case of a liquidation event (like the startup being acquired), stock options tend to become fully vested. This also makes you look even stronger as a candidate because it shows you’re long-term oriented.

I’ve heard over a dozen stories of early employees leaving a startup before the 1 year cliff (meaning they get no equity) and then massively regretting it when they realized that they left millions in equity on the table. Long time horizons are especially rewarded in startups. 

So – once you’ve found a startup you really believe in, impressed the team, and negotiated a fair compensation package for yourself –– how do you maximize your odds of success? 

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 getting into planning what you should do and in what order, it is important to figure out what the startup most needs. This can be done by asking the CEO and other leaders on your team, but should also include conversations with customers (current or future) so that 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 to share…

• “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.”

So, that brings us to step 1.

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

It’s important to understand that, until a startup has product/market fit, the #1, #2, and #3 priority of every single person in the company should be talking to customers and iterating 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’s definition complements it well: when a product is so good that customers spontaneously tell their friends about it, that’s when 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. 

While plans in startups are mostly useless since things change so quickly, the process of planning itself is extremely valuable because 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 as a result of having this clarity on what the business needs, 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 help local business owners own their businesses, online – starting with restaurants. We help local businesses fight back against the corporations like GrubHub that are stealing their customer data and destroying their businesses, with a suite of tools that help them take back control. Our all-in-one solutions powers online ordering, marketing automation, websites, recruiting, and more. Like Shopify + HubSpot, but specifically for restaurants.

The SVP Customer Success’s purpose is to build a world class customer experience immediately after owners signup for the platform – 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.

Notice how we start with the mission, then the most important business priorities, then what goals the candidate should accomplish within 90 days.

Choose goals that are simultaneously ambitious but 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 over. 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 are solved, and de-risks your business. 

Like starting a mega game of dominos by knocking down a giant domino, they require more force to initially knock down – but then knock down many smaller related domino’s as a result. 

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

The places I’ve noticed the A Class problems usually are, 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, if you’re joining as an engineer, you might want to dive into building new features as quickly as possible to solve medium impact and low impact problems that the customer experiences – improving customer retention and satisfaction. 

But if you notice an A Class problem with the way the codebase is architected and the startup is post-PMF, it might be worth paying down technical debt before adding more 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 that advantage gets lost when they get slowed down executing on countless small, minor things they could do, much like larger companies do.

<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.