191: Hiring Reality Check

191: Hiring Reality Check


So you want to land a great job or an amazing hire. Here's what you're probably overlooking.

Cultivating Resilience is a weekly newsletter about rebounding from setbacks and reinventing the future—by 3x founder and executive coach Jason Shen.

On paper, our labor market is doing great. In practice, people are on edge. High earners ($100k+) in particular are significantly more concerned about a loss of income now Jan 2024, compared Sept 2020.

I know a lot of folks are either actively looking for work after a mass layoff, or passively looking in case they are impacted by a future one. Sometimes these individuals come to me for coaching—though most of my clients are founders and org leaders.

And the thing is, landing a good job in tech these days is hard.

Of course it depends on a ton of factors like your relevant experience for the jobs you're applying for, the strength and reach of your professional network, how well you interview / negotiate, etc.

How's Your Top of Funnel?

But I think people don't always realize how much of marketing, sales, or other acquisition motion is a numbers game. As a quick aside:

Last week I had my biggest tweet of all time—a PG essay mindmap that did 250k impressions, which resulted 15k engagements (6% conversion rate) and in 77 follows (0.03%) and 37 newsletter subscribers (0.015%).

đź‘‹ welcome new friends!

Granted neither my Twitter profile nor this newsletter weren't really optimized for anyone specifically interested in "mind maps of insightful essays" but still, it's a reminder that you gotta shoot a lot of shots to generate a handful of wins—whether that's streams, first dates, or term sheets.

The principle holds true for job applications.

Getting To Yes

My friend Tal Flanchraych is a serial entrepreneur who recently left a stint leading new ventures Indeed and started ApplyAll. It's a tool to uses AI help jobseekers apply 100's of jobs based on your criteria (location, title, salary) at once.

She's been publishing customer success stories, and to be honest, even the wins feel kinda brutal.

In one example, a growth marketer applied to 529 jobs to get 2 offers. She used ApplyAll to add 473 additional applications to her job search. (full post)

She had ~8 final round interviews (mix between 3rd interview and takehome assignment) and both job offers came from ApplyAll jobs.

In another example, a laid off marketing exec spent more than a year looking for work.

He had extensive experience with brand name companies in Silicon Valley who was also a former NFL athlete and combat veteran.

We don't know how many total jobs he applied to, but he submitted 493 applications via ApplyAll before successfully landing an SVP of Marketing role. (full post)

I know this feels like an ad and yes ApplyAll costs money ($150+) so here my disclaimers are:

  1. I've not used it myself because my coaching practice is continuing to grow (10 active clients!) so I'm not looking for a job
  2. I don't get any commission for hyping this tool. It just makes a ton of sense and Tal is a friend and a founder I respect

Hiring Execs is Hard AF Too Though

You might think that given how hard it is for candidates to stand out and land roles, that hiring managers would have it easy.

And sure, it's nice to be able to get 1000+ applications for a given job, but as someone who founded a tech hiring platform and has a 5M view TED talk on the topic, the hard part then becomes figuring out who is actually a great fit.

Talk to any hiring manager and they'll tell you that it's exhausting to sort through applications, figure out who to contact, interview, and make offers to.

And you can't be sure that the people who have applied are actually the right talent—often the people who would be best for your open role are happily employed and not even looking.

It's hard for the average person to get insight on the difficulties of hiring senior talent. As a coach, I sometimes get a peek into this but even then, it's rarely the full focus of our sessions.

Which is why I want to share a fairly exhaustive post from Tara Viswanathan, cofounder and CEO of Rupa Health. Her company went through an interesting pivot that I document in my book The Path to Pivot, which is why I follow her closely on Linkedin.

She broke down how she was able to hire a Head of Engineering role for her Series A funded healthcare company in 8 weeks from kick off to signed offer during the holidays (Dec-Jan).

It required 300 hours of her time as CEO including many of nights and weekend calls with candidates (senior talent sometimes preferred / requested this) from a 200 candidate target list. She prioritized this above everything else she was doing as CEO (which requires the ability to delegate and a great team to run the ship while you're away.)

Prior to the actual job interviews, she also completed 20+ calibration learning interviews with top VP of Eng and CTO's to understand how great candidates think and behave. Many people don't realize how important this time consuming step is.

You have to really lean on your network to get these busy people to talk to you for a job they aren't even going to do, but it's a recommended practice for hiring execs. It does help demonstrate your commitment to the role and can elicit a larger network of people willing to support your search.

The work doesn't stop there.

If you aren't a well-known company that pays top of market (ie FAANG + Decacorn startups + Wall Street), convincing an amazing candidate to take a chance on a relative unknown is not easy. Plus if your top candidate turns down an offer, the next person might no longer be available.

And even after all that work, this new hire might not work out and then you have to run the process all over again.

While you start getting paid at a job right away, an executive hire might not start adding value for the company for 3-6 months as they take time to get up to speed and you start seeing their initial decisions pay off.

In the end, a truly stellar senior leader can be transformative for a company and free up a lot of time and energy for the CEO to lead in other areas. Similarly a landing a job that pays well, with great coworkers, and enables meaningful work is a huge contributor to our well-being—so the effort is worth it.

But whether you're a leader whose hiring or a candidate who is searching, the truth is that you'll have to search a lot farther and deeper than you may have expected to get a truly great outcome.

That's the reality check.


PSor more reality checks on how tech's current preference for hiring senior candidates might impact the ecosystem down the road, this video is a good warning.

How I Can Help You

As most of you know, I'm now a full-time coach and CEO via my firm Refactor Labs. With that, I have a couple ways I can help. Reach out if any of these speak to you or your organization.

🧢 Executive Coaching: 1:1 + small group sessions that unlock transformational growth through extended partnership.

🛠️ Participatory Workshops: Interactive seminars designed to learn and practice crucial skills for navigating complex transitions—storytelling, emotional intelligence, experimentation and more.

🎤 Keynote Talks: High energy presentations that challenges audiences to dream bigger and act bolder in the pursuit of excellence.

Coming soon: Templates, exercises, and other low-cost ways to build resilience and develop your outlierness.

Recent Issues

190: How to Do Great Work
đź’ˇThis issue of Cultivating Resilience is brought to you by The Next Chapter, a small group coaching program for founders & outliers in transition (final week to apply!) A couple of months ago, I wrote about timeless pieces of wisdom that I come back to again and again. 153: Timeless WisdomUnpacking
189: Deadlines are Magic
Don’t sleep on the power of attaching a timeline to your goals, big and small


188: Join the Club
Building a startup is hard. Through shared vulnerability and a love of scotch, Derek Flanzraich created a space for NYC to let their guard down and build each other up.