5 Tips to Getting a Job in SaaS in a Tougher Market (2025)

I know for many, this seems a much harder time to find a new job

What I can tell you is this. It’s not the crazy hiring market of 2021. But all the best start-ups and scale-ups are hiring, and even many of those doing Just OK are, too:

• I have at least 10 high quality portfolio companies looking hard for a great VP of Sales
• I have at least 8 high quality portfolio companies looking hard for a great VP of Marketing / Growth
• Every single portfolio company is looking to hire 2-30 great sales execs

If you are struggling, first ask yourself if you are great at it. Then, ask yourself if you are truly still willing to work. For real. Not 20 hours a week from home.

If so …

Then try harder to find that role.

Literally as I type this, I bumped into a great founder at $20m ARR at Starbucks growing 100%+ with tens of millions in the bank. He just raised his first round ever, after bootstrapping all the way to $20m ARR. His #1 issue? He just can’t find enough great folks to hire.

Everyone great is hiring. Not as many folks as 2021, in some cases. But almost everyone growing even at “pretty good” rates is hiring.

And it’s no easier today to find great people than it was in 2021.

However, it is true that it’s different today.

Start-ups, scale-ups and public companies in 2021 would hire a lot of folks they just wouldn’t hire today. And most bigger SaaS and Cloud companies are still hiring, but not at the same pace. In general, public companies are hiring at a slower pace than they are growing. In 2021, it was the opposite.

It’s different. If you are running the same playbook in 2025 to get a job that you ran in 2021, it probably won’t work.

So a few ideas to improve the odds that you get a job in this market:

1️⃣ Write truly great outbound emails to folks you’d truly want to work for, explaining exactly how you’d crush it, directly to the CEO / VP. Enough with the 1000 one-click job applications.

2️⃣ Consider taking a role with less strategy, more execution. So many execs I talk to mainly want to manage a team. That’s fine, but maybe it’s time to getting back to doing the work yourself. At least think about it. And don’t just say it. Prove it.

3️⃣ Do 2 hours of homework before each interview. Almost no one does this. It puts you ahead of 99% of candidates. So, so, so far ahead.

4️⃣ Enough with low effort feelers. Don’t ask for coffee or to “pick someone’s brain” or to “have a chat” and “see if maybe it’s a fit”. Make every interaction an A+ one.

5️⃣ I know it can be hard, but remember every executive is starting at email 1-2 hours a day. And hoping for an email that solves one of their top problems. So … send that email that truly solves their problem. Be the magic answer to their hiring needs. Not someone that wants to “pick you brain”.

Would you hire yourself based on that job email alone? Be honest. If not, take a pause and write it again. And better.

95% of the job application emails are … terrible. Honestly, probably 99%.