How to join a startup

Getting referrals, acing interviews & negotiating your next startup role

Everything is a sale.

As an engineer, I used to look down on sales as a not-so-worthy task.

Until I realized that nobody can fulfil their potential without sales.

In this article, I talk about how venture capital is all about selling.

And of course, getting a job in your dream startup is about sales too.

Key lessons from sales:

  • You need a lot of leads (aka getting your name in the candidates' pool)

  • Most people will say no (and that’s ok)

  • You must iterate and improve your process (take a moment to reflect on what is working or not every 3-4 weeks)

  • Showing > telling (don’t be too salesy/desperate and let your past experiences speak for themselves)

The 4 stages of recruiting in tech startups:

  • Referral or direct application

  • Screening interview

  • First round interview(s)

  • Final round interview(s)

If you are looking to join a fast-growing startup, here is the truth: the best positions at startups are never advertised.

So before you start applying to all the startup jobs on LinkedIn or Angelist, let’s look at how you can maximize your chances of getting an interview: referrals.

Paramount Network John GIF by Yellowstone

How to get referrals

  1. Direct referrals: someone you know in the industry who can hire, ideally the CEO or founder of a high-growth startup. This might not be so easy but your email contacts and LinkedIn connection are a gold mine (so don’t forget to scrape them)

  2. Weak ties: someone you met a few times but you don’t know that well. In this case, ask for a coffee chat or an “informal interview” where you can learn more about their work and their company needs.
    During an informal interview, never directly ask for a job (even if you found an open position) because you are building a relationship with someone you don’t know well, not closing a transaction.

    Here is a template with the best questions for an informal interview.

  3. Second-degree connections: After having tried the steps above, look for any connections of your connections (or friends) who might be working in your target companies. People you’ve worked with in the past are in the best position to refer you but close friends can work too. Once they make the introduction, we are back to having informal interviews

Asking for a referral

Most people want to help you but they probably would not know exactly what you are looking for unless you are very specific and make it easy for them to introduce you to someone.

Use a 1-sentence description of the opportunities you are looking for:

“I’m interested in senior mechanical engineering roles at a medical device startup, preferably in Switzerland or the UK”

The objective of a referral is to get an interview (not to get a job offer).

Cold reach out

If you can’t identify a connection to anyone in your target company, your only remaining option is to reach out directly to the CEO or another founder.

But don’t despair because, with a few tricks, you can become a master at reaching out to strangers, either with email, LinkedIn or X.

Here is a sample cold email by Ramit Sethi:

To: Jane
From: Samantha
Subject: Michigan State grad — would love to chat about your work at Deloitte

Hi Jane,

My name is Samantha Kerritt. I’m a ’04 grad from Michigan State (I know you were a few years before me) and I came across your name on our alumni site. [CREATE A CONNECTION AND SHARE WHY YOU REACHED OUT SO YOU DON’T LOOK LIKE A STALKER]

I’d love to get your career advice for 15-20 minutes. I’m currently working at Acme Tech Company, but many of my friends work in consulting and each time they tell me how much they love their job, I get more interested. [THE FIRST SENTENCE SAYS WHAT SHE WANTS. MOST PEOPLE ARE FLATTERED THAT PEOPLE WANT/VALUE THEIR ADVICE]

Most of them have told me that if I’m interested in consulting, I have to talk to someone at Deloitte. Do you think I could pick your brain on your job and what motivated you to choose Deloitte? I’d especially love to know how you made your choices after graduating from Michigan State. [THE PHRASE “PICK YOUR BRAIN” IS ONE OF THE BEST WAYS TO ASK FOR ADVICE AND FLATTER, AND “MICHIGAN STATE” REINFORCES SHARED BOND]

I can meet you for coffee or at your office…or wherever it’s convenient. I can work around you!
[THE BUSY PERSON IS MORE IMPORTANT THAN YOU. TREAT THEM ACCORDINGLY.]

Would it be possible for us to meet?
[A BUSY PERSON CAN SIMPLY REPLY TO THIS WITH A “YES” — PERFECT. NOTE THAT I DIDN’T ASK FOR THE TIME/LOCATION AS THAT’S TOO MUCH INFORMATION IN THE FIRST EMAIL.]

Thanks,
Samantha

Knowing how to cold outreach is a superpower and if you want to become an expert, check you out this masterclass.

How startups prioritize candidates

  1. Candidates from within - full-time employees working in other departments, part-time contractors or consultants

The best way to work at a fast-growing company is to have interacted or worked with them before they have an opening that matches your profile.

Putting aside moving between departments (which will require an entire article in itself), companies tend to hire people they have already worked with as this significantly de-risks their decision.

So if you are looking for a better position in business strategy at a health tech company, start by getting a temporary or freelance role where you help the leadership team screen some potential partners/acquisitions.

You can probably do this while you are still working at your current company too and before you need a full-time job.

With just a few hours/week, you’ll get the chance to show your work while getting a first-hand experience of the company culture.

To get a part-time/freelance job, keep reading the next sections as it’s practically a similar process to a full-time role, just with lower risk and less commitment from both sides.

Tip: for paid positions don’t forget to check your current employment agreement.

  1. Candidates who prove they can do the job - using case studies or previous experiences with relevant results

Do a thorough analysis of the job description and look for hints of what your KPIs would be in the first 3-6 months.

Follow up with some research on the company (website, social media, articles), and leadership (public speaking, videos, personal blogs) until you figure out which problems you will need to solve.

Most interview processes include a quick screening interview with an HR professional; use that chance to ask 1-2 questions about the specific role (more on this below).

Then put together 2 pages/slides with your previous achievements that reflect the objectives the company has for you.

Start with the following framework: “I led company X to achieve Y which led to outcome Z”. Be specific and quantify the initial situation, your process, obstacles and final outcomes. Limit it to 1 page per case study.

Working on a project before the interview

Preparing a short and clear portfolio for your position will make you stand up from most of the applicants.

But if you really want to leave a mark, work on a one-pager that proposes a solution to a few of the problems you have identified following the previous steps.

It doesn’t need to be overly scientific. The goal is to show that you have identified a few of your key future areas of responsibility and that you are proactive and resourceful in having done some work without being asked.

It’s usually not easy to find a lot of information about early-stage companies online so try to do this project after they send you their pitch deck.

The recruiting process in startups can drastically vary but one way could be to ask for a deck during the 1st interview, work on this project the following weekend and send it to the CEO on Monday, no matter if you have already heard back from them or not.

In other cases, you might want to send this project after your screening interview and ahead of your first interview with the CEO.

Pro tip: ask someone you trust to review your portfolio and your project before sending it to the company, especially if you are applying for a new role or a new industry.

Past performance is the best predictor of future performance

If you want to learn more about the startup perspective when hiring great employees, have a look at the guide “Build the right startup teams”.

Screening interview

Usually done by phone or video call (15-30 minutes) by an HR professional, oftentimes junior. In short, they are looking to remove candidates who are not a fit, either technically or professionally. So don’t be late, keep your answer short, highlight 1 or 2 achievements that are relevant to the role and don’t be a jerk.

This is not the stage to impress them with your hot takes or contrarian views.

First-round/final-round interviews

These interviews usually last 30 to 60 minutes and are 1-1 calls with the hiring person or the CEO, depending on the company stage and your role.

A 60-minute call is split into a mutual introduction (10 minutes), questions from the interviewer (40 minutes), questions from the candidate (10 minutes)

Most first-round interviews focus on behavioural questions, highlighting past experiences.

Here are my 3 favourite behavioural questions:

  • Tell me about a significant big decision you made in the last year or two that you'd change. What would you do and why?

  • Tell me about a time when you had a big work disagreement with your peer. What happened, what did you do and how did it resolve?

  • How do you define success? What is important to you?

If you are interested in a list of common behavioural questions, check this out.

How to prepare for an interview

Start by auditing your online presence (social media, blogs, Github) and make the right adjustments to best represent yourself for your next role.

Sometimes this means getting rid of old posts or not relevant projects. If this is the case, focus on having a straightforward narrative and don’t be afraid to remove content that is not relevant or that does not reflect your expertise anymore.

Make sure you have a clear answer to the most common questions:

  • Tell me about yourself

  • Why do you want this job?
    Focus on what you’ll bring to the role and how this position fits within your overall career trajectory

  • What made you apply to work with us?

  • Do you have any questions for me?

Regarding behavioural questions, keep in mind the STAR framework:

  • S - Situation: What happened?

  • T - Task: What were your responsibilities?

  • A - Action: What did you do?

  • R - Result: The outcome of your actions

To prepare for those, look back at your experiences and choose 2-3 episodes where you had a major contribution to a large project that led to a significant outcome for the company.

In simple words, you want to select cases where you have been a key player in an important project for the company.

Recent projects are also perceived as much stronger and relevant so try to find instances of projects that happened in the past 2 years.

When using the STAR approach, don’t forget to add what you learned and how you incorporated those learnings in future situations. Behavioural questions are almost always about non-straightforward situations so it’s okay to share that things turned out differently as long as we learned.

Asking the right questions

  • Forget lists of pre-made questions. Ask what you are genuinely interested in and that will help you understand more about what’s important to you

  • Don’t forget strategic questions. In addition to asking about your day-to-day role and team, try to understand why the role is open, why the company is going in a certain direction and how the next 6 months fit within the broader company mission

  • Ask questions that show you’ve done your homework. After your research, you’ll be in the best position to dig deeper into sides of the business that are relevant to your role or that you’d like to know more about

When asking questions, don’t shy away from critical aspects of the company and feel free to dig deeper if the initial answer does not fully satisfy you.

Great founders are looking for people who are curious and who look beyond their assigned tasks. If you feel this is not the case, move on. The beauty of working in a startup is having greater responsibilities than one’s previous experiences. Otherwise, you’d be better off with a large company.

Some topics are tough to be discussed openly in an interview so keep an uplifting tone by framing the question in a positive and curious way.

For example: “I’m excited about the company’s growth trajectory and I’d like to learn more. What are the incoming largest investments in terms of projects/departments/hiring and how do they reflect the current runway?”

Avoid using a confrontational tone like “What did you promise to your investors during the latest funding round?” or “Why did you lose 3 employees in the past month?”

I can assure you that there will be not enough time to answer all your questions during the 1st round of interviews so ask for their latest non-confidential pitch deck (I can’t stress this enough).

There is no real reason for them not to give it to you so it’s not a good sign if they start finding excuses.

This will also give you invaluable insights to work on your projects before the next interview as discussed before.

Mirroring

Starting from the job description, pitch deck or any other documents you have about the company, highlight keywords that reflect the jargon of people working there.

For example, a business strategy role might require you to be data-driven in your research, while constantly being proactively on top of industry news to take advantage of market changes.

Add these words to a document and use the same words in your answers.

If you want to learn more about this technique, check out Robert Cialdini's book ”Influence”.

Reference interviews

Assume the founder/CEO will do reference calls with your previous colleagues so don’t be afraid to do the same.

Aim for 2-3 reference calls and focus on your direct manager and/or the company CEO.

At this point, you are already very interested in the company and they have probably convinced you to join the team. If you are not familiar with reference calls, just keep in mind that the goal is to find hidden red flags that could turn a dream into a nightmare.

For example, a culture of harassment, pending lawsuits with current/former employees, and reasons why your future boss left or was fired from his previous company.

For these reasons, you might want to speak with former employees (LinkedIn is a gold mine), the previous boss of the CEO or the previous boss of your boss.

You are most likely going to speak with a few team members during the recruiting process. Don’t be afraid to do so over a coffee in real life as this is usually the best way to learn about the company culture without asking about it.

In an early-stage startup, it’s not uncommon for strong candidates to speak with company investors. If you feel having a chat with someone who invested in the company will clarify some questions, ask right away. In the end, you are both investors: they are investing money and you’re investing time.

Salary negotiation

At a large company, salary compensation is pretty much a formula.

In a startup, it’s not.

You’ll probably negotiate your compensation with one of the founders and there are multiple factors that play into the discussion:

  • The state of the company (revenue, money raised, profitability)

  • Your role and responsibilities within the company

  • The value of the company equity and the stock options dynamics

Great working relationships are based on mutual trust so if you are negotiating an offer with an early-stage company, they probably think you are an exceptional talent and they wouldn’t hide key company information.

Ask for metrics regarding the state of the company, including valuation and stock options financials. You should expect a stock option plan already in place after the founders and board's approval.

If you want to learn more about stock options and how this works from the company perspective, check out Chapter 3 of “How to build startup teams”.

Tip: if they ask you for an expected salary, never say a number first. Ask for a range that they have budgeted and then assess if that fits within your expectations. Sometimes it can feel like a stalling game but make sure you’re not the one to cave first. Founders have almost unlimited flexibility and your best moment to negotiate is just before joining the company.

Good luck getting into an amazing startup and if you have questions, don’t be a stranger and send me an email at [email protected].

This week's top reads

Read my comments on these articles here.

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