How My Current Job Search Differs From My Last Job Search

Exactly one year ago, I started a job search, and now here I am again—starting another. What happened??

My last search led to an amazing role at a venture studio, heading growth for a confidential real estate startup. But six months in, “strategic realignments” at the executive level resulted in them laying off most of the studio (30+ people) including myself.

So, here I am, picking myself up and diving back into the search. There's not much “dust” to brush off since I was doing this just one year ago. ??

That said, I’m approaching things differently this time around. I've learned a few lessons about what worked and what didn’t, and I'm here to share those with you.

Here are 5 ways my current job search differs from the one I conducted a year ago:

• People over Applications
• Growth Roles over Product Roles
• Fully Embracing AI tools
• Networking Over Networking Events
• Flow State over Hustle State

I’m blogging here again (just like last time) to clarify my strategy, help other job seekers, and show future employers how I tackle challenges. While my focus is on securing a remote Growth role at a growing B2B SaaS company, these strategies should apply to anyone.

People over Applications

In my last search, I applied to 196+ job postings, went through 12 interview processes, got 18 rejections, and received 20 referrals. Patterns emerge quickly reviewing this data: most of the roles I landed interviews for came through referrals, not cold applications.

This wasn’t surprising to me. Cold applications often go unread, buried in a stack of resumes. Even though my last system started scraping job boards to find opportunities and then networking into them to get referrals, it often led to dead ends.?

The role I eventually landed wasn’t even posted, and neither were the last 5 jobs in my career. So why did my process start with job postings then?!

This time around, I’m focusing less on scanning job sites and more on connecting with people. The job boards will help me identify companies and roles, but my primary strategy should be direct outreach to allies and well-positioned folks, regardless of job openings.

Instead of tracking how many applications I submit, I’m measuring how much outreach I do, in line with Phyl Terry’s excellent Never Search Alone book and community.

Growth Roles over Product Roles

Another takeaway from my last job search was that most of the interviews I landed were for growth roles, even though I was primarily applying for product roles. After spending four years leading product for my bootstrapped startup Reciprocity, I assumed I’d be well-positioned for a product management role.

It turns out, hiring managers see me as a “growth guy.” When it comes to choosing a PM, they wanted someone with PM experience—which I didn’t have on paper. Even after tweaking my resume to highlight my product work, it wasn’t enough to overcome the fact that most of my formal titles are all growth-related, and of course I stopped short of fabricating information.

While I still aspire to work in product and know I have the skills to do it, I’ve learned it may be easier to transition into product from within a company rather than trying to break in from the outside.

So, this time, I’m focusing on growth roles, where I shine as an applicant with nine years of experience and two co-founding stints. It’s just a matter of presenting myself to the right people.

Fully Embracing AI tools

During my last search, I discovered tools like LazyApply, Massive and ApplyAll, which automate applications to hundreds of jobs. I hesitated to use them, thinking they wouldn’t help me put my best foot forward. This time, I’ve let go of that hesitation and signed up for all of them.?

Most job applications are straightforward—upload a resume and answer standard questions about visa eligibility. AI tools can handle that efficiently. I still manually complete applications that require short answers, but I’m happy to let AI save me time on the more repetitive tasks. If anything, employers should see it as a good thing that I’m not getting bogged down in tasks better done by an AI.

So far, ApplyAll and Massive have impressed me, while LazyApply has been less effective. Watching application confirmations roll into my inbox for roles I didn’t know existed is a nice perk.

?Networking Over Networking Events

One of the great things about living in San Francisco is the abundance of tech jobs, people and events. (It can also be annoying, but for a techie job hunt, it’s a godsend). In my last search, I attended several events but, in hindsight, never spoke again to most of those people.

I know that weak links are known to lead to job opportunities and all it takes is one right person to change your life, but I’ve found that forcing small talk with strangers who aren’t excited to speak with me doesn’t add value to either party.? Instead of “showing face” at networking events, I’m making networking a natural part of my everyday life.

That means I’m authentic about my job search in conversations, inquire about friends’ work, and look for connections beyond formal networking events. When done sincerely, it deepens relationships rather than feeling pushy, and everyone is usually happy to help.

Flow State over Hustle State

Perhaps the biggest change this time is my mindset.? I treated my last search as an ‘unemployed’ full-time job, which was distinctly separated from the earlier period of “funemployment” when I wasn’t searching.

This time, I’m going in with a recent hire under my belt, 6 months of tech salary income, and the learned wisdom that one doesn’t have to separate the ‘fun’ from the ‘unemployment’. They can be two sides of the same coin.

So I take care every day to prioritize the unemployed joy and spontaneity as much as the diligence and routine that a job search requires. For me that looks like waking without an alarm, doing my full morning routine unhurriedly, saying yes to long hangs with friends, and continuing my learning journeys around clowning, deejaying, and singing that I started during my last funemployment.

I believe I can curate a flowing lifestyle that generates job opportunities, rather than one in which jobs exist independently and I must hustle for them.

Conclusion

I recognize it’s easy to stay positive in the first month of a job search, and that I may be singing a different tune 7 months in. My financial savings remain finite, as much as I’d like to live in a world of infinite abundance.?

I can’t help but remember that my last job didn’t come from hustle but rather from flow, as it resulted from a Linkedin acquaintance seeing my last job search blog post (much like this one). So, maybe the answer isn’t about grinding through applications but instead focusing on sharing content, connecting with people, and being open to possibilities.?

That’s what worked last time, which means this post is just the beginning. I’ll be writing more about the search process, and sharing tips, tricks, and case studies along the way.

Needless to say, if you know anyone hiring growth folks, please send them my way.

And how about you? How have your job searches evolved over time?

I’d love to hear about it. :)