Job Search Like A Startup Expert

JOB SEARCH STRATEGY
Y-Combinator Knows A Thing Or Two.

When it comes to startups, there are not many more revered sources than Y-Combinator. Launched in 2005, Y-Combinator has been a hotbed for technology innovation. The accelerator program has launched over 4,000 companies, many of which have become household names.

Stripe, Airbnb, Cruise, DoorDash, Coinbase, Instacart, Dropbox, Flexport, Brex, Reddit, and Zapier… ever heard of them?

The program’s goal is for there to be more startups by helping founders to start them. But the lessons they share with their founders can be hijacked by anyone looking to land a job at the next generation of world-changing startups.

There are only so many hours in a day, and running an effective job search will require many of them. So, how do you use that time wisely and be more productive?

Productivity Is What It’s All About.

Let’s be honest. No one wants to search for a new job. In an ideal world, it would be fast, effective, and get your butt into a seat on a rocket ship.

Recently, the Y-Combinator Group Partners (the advisors helping founders build world-changing companies) shared their favorite strategies to be more effective and reduce distractions at work. You can steal them for your job search.

To land the startup role you want, it requires working smarter AND harder to win.

Focus on Your Customers.

Tip #1 - Stay laser-focused on your customers and what they want.

In your job search, you have one customer and one customer only.

The hiring manager.

What’s the problem that they care about?

What’s the solution that’s going to help them?

How do you stay laser-focused on that?

Spend as much time as it takes to look at your background to understand what you have in your toolkit of skills, experiences, and networks that could help then solve a problem or take advantage of an opportunity.

Even once you figure that out, it’s easy to get distracted.

Don’t Get Distracted.

Tip #2 - Avoid “shiny objects” and focus on the core mission.

With the AI craze, there is no shortage of new tools to try, programs to learn, and software to play with. Those things are fun!

There are also always tasks in front of you that you could be doing. Constant resume updates, LinkedIn optimization, job board scrolling. Those things are always there, are easy to do, and are easily accessible.

But beware of the fun and accessible.

What’s going to move the needle

Identify what’s going to move the needle and focus on that. The path to the destination is not as straightforward as in school, where there’s a defined path to graduation, or in a job where you can ask a manager.

In most of the job searches I have seen, what moves the needle is networking (and application by networking) and value creation. Test out your strategies in different ways, with different people, in different locations. See what sticks, see what doesn’t, and adjust your strategy accordingly.

Track Your KPIs.

Tip #3 - Be explicit about your target and write it down.

What are your priorities?

What is your main KPI?

What is your main bottleneck?

What do you need to do to make your KPI move in the right direction?

What’s Your KPI?

Focus on a single number.

When job searching, the most effective KPI that I have found is the number of networking outreach messages I’m sending.

Why?

Networking outreach leads to conversations, conversations lead to relationships, relationships lead to referrals, referrals lead to interviews, interviews lead to final interviews, final interviews lead to offers.

So start at the top of the funnel.

If you track your metrics, you can scientifically back your way into the total number of messages you need to send to land multiple final offers.

Stay On Track

Once you have identified your key KPI, look at your calendar and ask yourself if it reflects your main KPIs.

Ask yourself, “Is what I am doing aligned with what I have said is important?”

You Probably Don’t Need That New Thing.

Tip #4 - Avoid productivity fads

AI productivity tools, the perfect resume optimizer, cold plunges, neotropics, and productivity software.

Some of these things are good.

Most of the time, these are things that worked for someone else, and they may or may not work for you.

Don’t accept them as the end all be all and a silver bullet.

In fact, most people (I’d say all, but I don’t want to be too prescriptive) would benefit far more from removing all of these things from their lives and adding single elements one at a time.

It’s easy to fall victim to “productivity porn” or consuming content about how to be more productive (oops, that’s kind of what this edition is all about).

What you need is not another habit to increase your productivity.

It’s focusing on the one thing that will make a difference.

If you focus your job search right, you won’t need to worry about productivity because it will feel natural.

You’ll naturally be speaking about how you helped companies in the past.

You’ll naturally ask for meetings with people you’re interested in and ask questions you genuinely want to know the answer to.

Are You Cleaning Your Room Because You Don’t Want To Do Your Homework?

Tip #5 - Distinguish real work from fake work.

I have seen job hunters who have built these complex automation systems, trackers, notion wikis, and constant alerts.

This is the equivalent of cleaning your room because you don’t want to do your homework.

It feels like you’re being productive, but you’re not actually getting anything done.

There are two types of fake work: obvious fake work and non-obvious fake work.

The obvious fake work is easy to self-identify.

Watching Netflix for 4 hours in the middle of the day or during the time you had allotted to focus on other things is obvious fake work.

Non-obvious fake work is far more sinister, which is why people see months fly by feeling busy without making much progress.

Non-obvious fake work is doing things you don’t really want to do, but that also gets you no closer to your ultimate goal.

Here are some examples:

• Sending hundreds of cold applications

• Updating your resume for the 100th time

• Scrolling job boards hoping to see the perfect role

• Rechecking LinkedIn, hoping to see a post about a job opening

How To Solve For It

When starting a task or a project, ask yourself, “What is the particular goal I’m trying to reach by taking this action?”

If you don’t know the answer or you know the answer and it won’t have a significant impact on your ultimate goal, it’s likely fake work.

Don’t do it.

Go back to your KPIs and take the right action that will move the needle (likely more networking and value creation).

Maker vs Manager Schedule.

Tip #6 - Divide your day up into two parts: Meetings and creative work

The founder of Y-Combinator, Paul Graham, has written many famous essays.

If you haven’t read them, I highly recommend checking them out.

One of his more famous essays is Maker’s Schedule, Manager’s Schedule.

In summary, it boils down to this.

Humans are terrible at context-switching.

When we try to switch between creative work and meetings, we do neither well.

So, instead, block off your calendar and focus on only one.

Things On Your Maker Schedule

• Working on a resume update for a specific company or application.

• Batching individuals at target companies for networking outreach.

• Doing networking outreach.

• Updating and optimizing your LinkedIn profile.

• Crafting value deliverables for target companies.

These are most effective when it’s the only thing you’re working on, and you can go deep and shut everything out.

Things On Your Manager Schedule

• Any kind of meeting

• Networking conversations

• Interviews.

Try and batch these as much as possible.

How to Optimize Your Schedule

Block off days or times of day for each type of activity.

Maker in the morning if you’re more productive in the morning and manager in the afternoon.

Maker on Mondays, Wednesdays, and Fridays, and manager on Tuesdays and Thursdays.

Whatever works best for you.

I have tested both and found both to be effective.

Right now, I do deep creative work or work on my company on Mondays, Wednesdays, and Fridays and batch all my meetings into Tuesdays and Thursdays.

Be Cautious with Social Media.

Tip #7 - Be intentional about time spent on social media

I know I probably sound like your mother but, “Get off your damn phone!”

Social media can be especially harmful to your job search in three ways.

Distraction

The first and most obvious is that it can be a significant distraction.

Take a look at your screen time and see which apps are eating most of your time.

I can almost guarantee you much of that time could be put to better use in your job search.

Comparison

It’s good to get motivation from people further ahead than you or doing what you want to be doing at a high level.

It’s not good if those things are making you feel worse about yourself, making you feel less confident in yourself, and discouraging you from taking the action that you know you need to.

If you see yourself consuming content and feeling worse about yourself and your career, eliminate it.

Doom Scrolling

You see this often on LinkedIn with people who like and comment on posts about hiring managers who ghost candidates or people who have been on the job search for months and months.

You are not a victim.

You are the captain directing your career where you want it to go.

Avoid the pity party at all costs.

Use Social Media As A Tool.

Tip #8 - Use Social Media to build relationships with customers

Not all social media use is terrible and a waste of time.

It can be helpful, if you’re using it for your main KPI, to get more networking conversations and display your value.

Use social media to strategically build relationships with hiring managers and people at the companies where you want to work.

The best platform for this is not Instagram or TikTok.

LinkedIn, X, GitHub, Hacker News, and industry and startup communities are where your hiring managers are, and that is where you can and should be engaging on and consuming social media.

Where it can be used for good

When you open the app, ask yourself, “What purpose is this serving?”

Are you following and engaging with people at the companies or the founders and investors you want to work for?

Are you consuming stories about people in your ideal line of work?

Are you using it to build your network, land more networking conversations, build better relationships, put your expertise out there, and get more interviews?

If the answer is no and it’s not serving your goal of landing the type of role you want, then cut it!

Track It

• What do you believe is your biggest strength to offer?

• Who are your target hiring managers and companies?

• How do you get in front of them? Where do they hang out?

• What are things that they can tell you that nobody else in this hiring market has tried to fix or solve for them?

Approach your social media strategy in that way and you’ll win.

Focus Only On Top Priorities.

Tip #9 - Stack Rank Your Priorities

Everyone has tens, dozens, maybe even hundreds of tasks they could work on at any given time.

Of all the things you’re currently working on or conversations or interviews you’re in the process of, what’s their stack rank?

Can you order them by priority?

Often, we will try and tackle them all.

By stack ranking them it forces you to prioritize.

Exercise

• What are all the things you are working on right now?

• What are all the companies you are applying to?

• Who are all the people you’re reaching out to right now?

• Stack rank them from 1 to 10 in terms of importance.

• You cannot rank two things with the same number.

• Work on your top 3 and put the rest aside.

• You will never be able to accomplish all 10 right now, so focus on doing your top 3 now, and once they’re complete, go through the exercise again.

What’s Your Why?

Remember the KPIs we talked about earlier?

Focus on a single number.

What’s the most important number when you’re trying to land your next job?

Again, it’s likely the amount of outreach messages you’re sending.

Are your top priorities aligned with that KPI?

Ruthlessly Eliminate Non-Priorities.

Tip #10 - Identify what is NOT a priority

Most people think time management comes from deciding what to do.

In reality, the best mental model for time management is what you decide not to do.

There are an infinite number of things that want to take your time.

You have to make conscious decisions about what is not a priority.

The Hard Choices

This is a tricky subject because people will say, “But I go out on the weekends because I worked so hard on my job search during the week!”

Or, “I planned this trip with these people for months.”

But ultimately, you will need to disappoint some people to get to where you want to be.

Remember, it doesn’t need to be permanent.

It’s okay to disappoint people, be slow to respond to messages and emails, miss social engagements, say no to conversations that don’t serve your goal, and skip vacations.

Be Selfish

This is a critical time in your life and your career.

It should be about you and what your priorities are for your life and career.

You do not need to say “Yes” to everything because by saying “Yes” to something, you’re saying “No” to something else that you might not even be aware of.

If people truly support you they will understand.

And if they don’t understand, do they really matter?

No One Is A Good Multitasker.

Tip #11 - Avoid Multitasking

It’s not about getting more done by doing a lot of things.

It’s about getting more done by hyper-focusing on one thing at a time.

What is Your Job?

Your job is to talk to people who can influence your ability to land a job and build a case for why they should hire you.

Unless whatever you’re doing helps you do one of those two things, then it’s likely not important.

Stop trying to do everything at once.

That just leads to doing everything poorly.

Do The Work.

Tip #12 - Productivity tools don’t substitute work

At the end of the day, nothing can substitute putting in the hours on the things that will make a difference.

You’re not going to land a job with a single networking message.

You’re not going to land a job with a single application.

You’re not going to land a job with a single interview.

If you’re constantly spending your time looking for the shortcut or the way not to work as hard, then your job search is going to be a struggle.

Commit to putting in the time to do good work, and it will pay off.

OPEN ROLES
Who’s Hiring?

Island

• What They Do: Island makes a special kind of internet browser for businesses. Think of it like Google Chrome or Safari, but with extra safety features. It lets companies work smoothly online while making sure their information is super secure. This way, businesses can do their tasks without worrying about online threats or hackers.

• Total Raised To Date: $375.00M

• Last Raise Date: October 23, 2023

• Recent Raise: $100.00M

• Series: C

• Number of Employees: 220

• Open Roles? Yes

• Pitchbook Success Probability: 98% Success

Omnidian

• What They Do: Omnidian has created special technology to keep an eye on and boost the performance of energy equipment used in homes and businesses. Think of it like a security camera and a personal trainer for your energy devices. It constantly checks to ensure everything's working right, sends alerts if there's an issue, and even offers repair services. This helps people and businesses feel confident that their energy equipment is safe and working at its best, saving them money and time in the long run.

• Total Raised To Date: $89.50M

• Last Raise Date: October 26, 2023

• Recent Raise: $25.00M

• Series: B

• Number of Employees: 200

• Open Roles? Yes

• Pitchbook Success Probability: 98% Success

Abridge

• What They Do: Abridge has created a healthcare app that records and breaks down medical talks using machine learning. It's like having a smart assistant that listens in, makes sense of doctor chats, and helps users remember and understand what their doctors advise, keeping them informed and on track.

• Total Raised To Date: $63.90M

• Last Raise Date: October 26, 2023

• Recent Raise: $30.00M

• Series: B

• Number of Employees: 46

• Open Roles? Yes

• Pitchbook Success Probability: 96% Success

So there you have it, 12 productivity tips from the best and brightest at Y-Combinator, who are the Mr. Miyagi’s of the next generation of unicorn founders.

There’s a general theme here, and that is FOCUS.

It’s not about trying to do everything.

It’s about finding the things that move you closer to an offer and executing them consistently.

Let’s become career champions together 🏆

Kyle