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On Staying the Course
JOB SEARCH STRATEGY
ON STAYING THE COURSE.
Good morning everyone, or good afternoon to all you European readers!
Today, I want to address something I heard multiple times this week.
It’s an issue I see pop up all too often, and it’s one of the major reasons why people derail their job search.
I’ll call it…
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“IT’S SO COMPETITIVE OUT THERE”
Everywhere I turn, I hear people talking about the competitiveness of the job market.
It feels competitive, but what does the data say?
In their H2 2023 State of Compensation Report, Carta shared data showing that last year more people left than joined startup companies.

That’s the first time that has happened since Carta was founded in 2012.
As I looked at this data, two things stood out…
Beware Of Getting Caught Up In Headlines.
“50% DECREASE IN YEAR OVER YEAR STARTUP HIRING”
That sounds terrible, and it is a massive decrease.
But, if you don’t look at the data from prior years, you would think startups are worse off than they’ve ever been and hiring a fraction of the number of people they used to, which simply isn’t true.
The number of people who joined a startup in 2023 is close (or at least much closer) to the “normalized” totals of 2019 and 2020 before markets got incredibly inefficient and the startup funding bubble burst (-4% vs 2019 and -6% vs 2020).
What we saw in 2023 was simply a return to normalcy after the startup hiring market went crazy in 2021 and increased by 46% year over year and maintained that level through 2022.
Startup hiring increased by 86% between 2021 and 2022 vs the prior two years so it only makes sense that there would be some sort of correction and that we wouldn’t see hiring continue to rise to the stratosphere.
The Numbers Check Out.
The fact that hiring has returned to pre-pandemic normalcy doesn’t feel reassuring to the average startup job seeker and that’s because while the supply of jobs has returned to a normal level, the demand has never been higher.
I don’t have the data on the total number of startup job seekers, but if you take the >500k people who departed startups in the last two years and add them to the tens of thousands of people who were laid off from big-tech or other non-tech industries there is far more demand for these jobs than recent memory.
While some people might think that people would be turned off by startups because of the turmoil in fundraising and company closures, I have seen the opposite.
More people are coming from non-startup companies and looking to get into startups because of the opportunity to get exposure to company building, expanded role responsibilities and scope, and to work on products and missions they are excited about.
We had the great resignation, but this feels like a great awakening.
People want to work again, and they want that work to be something they care about.
They feel like their best chance to do that is in a startup (and I agree with them).
In summary, startups have returned to their previous hiring numbers, but demand has never been higher, and companies, with the decrease in fundraising, are scrutinizing every new hire they make and determining whether they should hire, automate, or offshore, which means that the numbers back up what you’re feeling.
It’s highly competitive in the startup job market.
DATA BITE: Even taking into account 2023’s 18k startup job decrease, Carta’s data shows that since 2019, there have been a net new 853k startup jobs created. So the number of people working in startups is still much larger than it was in 2019.
DEVIATING FROM BEST PRACTICES.
Two conversations I had this week stood out to me as a microcosm of the current startup job search and the challenges job seekers are facing.
Sr. Director of Customer Support.
The first conversation was with a member of the UpEmployment Accelerator who recently landed a job as the Sr. Director of Customer Support.
She joined the accelerator in early March and landed her role 64 days (~2 months) later.
After people land a job, we jump on a call to prep them for their new role and hear about their experience in the job search.
One of the questions I always ask is, “Where did you struggle?”
She said, “You want to apply to jobs, you want to get a job, but you’ve got to put in the work to find the right job. And I struggled with that. Like, if you only had two hours, should I be focusing on doing the things you recommend to find those target companies or just apply to jobs. And in hindsight, I wish I would have focused on doing the work and maybe not focused on applying so much and get to that target list sooner to start doing the focused work. Because I feel like I got distracted.”
“You get lost in all these applications. I mean, you do so many of them because you think in your mind, ‘Oh my god, if I do a thousand or a hundred a day, something’s got to stick.’ Well, to be honest, nothing stuck.”
What worked for her were the methods we describe as best practices.
Get crystal clear on the specific types of companies and roles you want, and then focus the vast majority of your time on networking with people you know at those types of companies and doing cold outreach to build relationships with new connections.
Her networking paid off, and she was referred by a previous manager to the position she landed.
This is coming from someone who is inside a program providing hands on assistance, tools, services, resources, and mentorship on the best practices to land a job in a startup.
Those who aren’t getting this support can waste months deviating from these best practices without any results to show for it because there’s no one to get them back on track.
Technical Program Manager.
The second call I had this week was with a technical program manager recently laid off from Amazon.
He has been on the job search for two months so I asked him about his current strategy.
“I filter for jobs with less than 10 applications and jobs that have easy apply so that I’m able to complete maybe say 30 or 40 applications. On any given day, you could say I apply for maybe 50 to 60 roles. In the first month, I was reaching out to people, but that did not really help because I believe people are getting overwhelmed at this point because there are so many people in the market looking for jobs and everybody, everyone reaches out to these people.”
He wants to work in a smaller startup company, but when I asked about what types of companies he was applying to, it was all over the place.
This is exactly what the Sr. Director of Customer Support was referring to.
Deep down, you know and have heard that focusing on a small targeted list and networking has a higher likelihood of landing you a job but it doesn’t create the immediate feeling of traction so you abandon that strategy in favor of something that FEELS like you’re making progress.
People abandon the best practices and revert to the “traditional job search” of mass application on the off chance that they’re the one who wins the easy-apply lottery.
STAY THE COURSE.
I often get asked, “How should my strategy change in an employee vs employer advantaged job market?“
My answer has always remained the same.
It shouldn’t.
The roles at the best companies will always be competitive and there’s a tried and true method to land those jobs.
That method is not sending applications en-mass.
Sending mass applications has never been less effective.
There are many factors that have made this tactic decrease in effectiveness.
The easy apply button made it as simple as one click to send an application to a job regardless of how well you fit that job description.
Remote work increased the number of people who were relevant for that position.
AI resume assistance has made it easy for people to customize their resumes to match the job description as accurately as possible.
For a small fee, AI bots will now apply for hundreds of jobs for you every month.
The result is overflowing ATS systems for every role with dozens of resumes that match the characteristics the hiring team is looking for.
But in any market, the things that do stand out are the unscalable methods that demonstrate your interest, excitement, and perfect fit for the role.
That means:
Having a clear understanding of the size, stage, and industry of the company you want to join.
Having a clear understanding of the specific role characteristics you want and why.
Crafting a personal story that resonates with people you network with and your target companies that makes it clear you’re someone who doesn’t just want A job, you’re looking for THE job.
Using your prior results and current personal drive to craft unshakeable confidence that only it’s a matter of time before you find the company that understands the value you can bring.
Updating your personal branding on LinkedIn to demonstrate your subject matter expertise and results-driven in that specific field.
Creating a targeted list of companies that match the characteristics you’re looking for.
Focusing on engaging with your network to learn how they navigated their career and describing the specific role you’re looking for next so they can provide connections, recommendations, and referrals.
Focusing on engaging with people at your target companies to better understand who they are, what they care about, and the problems they are solving.
Crafting targeted outreach that makes you stand out, including video introductions, video testimonials from prior colleagues, and value deliverables.
And continuing to execute that process until you land a job.
In short, it’s clarity of direction, networking, value creation, and preparation.
It’s hard to dig deep and understand what you really want and only focus on that direction.
It’s easy to see a job and click apply.
Your mind will tell you, “But I could be applying to jobs right now!”
And that’s true.
But the Navy Seal mantra of “slow is smooth and smooth is fast” is more true.
These conversations and focused efforts often don’t see immediate results.
You don’t get the dopamine hit of looking at your job tracker at the end of the day and seeing 50 job applications submitted.
What you do see is more traction with fewer people and fewer companies which leads to better results.
If the last two years of running UpEmployment have taught me anything, it’s that the method I laid out above works.
In the first month, you’ll lay the groundwork and start to execute your strategy.
In month two, you’ll have enough reps that you’ll be prepared for an opportunity when it arises.
And midway through month three, you’ll have one or multiple opportunities fall in your lap, often seemingly out of nowhere, that you’ll crush because your preparedness has met opportunity.
Sometimes those opportunities come sooner but, on average, they come in 2.5 months.
That progression will not happen if you’re randomly applying to companies in different industries, of different sizes, different stages, and for different roles.
So, even though it’s difficult in this moment, I encourage you to stay the course.
Continue executing the best practices that have been the proven way people have landed career-accelerating roles at dream companies.
Do not get sucked into the siren song of sending hundreds of applications every week.
And if you need support along the way, I’m always here for you.
Let’s become career champions together 🏆
Kyle

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