85: The AI-Assisted Job Search, with Taylor Desseyn

Job postings are climbing and plenty of engineers still can't get a reply. Erika and Brittany sit down with Taylor Desseyn to ask why, and what to actually do about it.

Taylor opens with the disconnect: postings are up against a three year look back and Randstad's state of the market report just logged its first positive quarter in a while, but doom and gloom travels further on the internet than good news, and big tech layoffs control the headlines. The practical reason roles feel unfillable is that hiring managers frequently have a candidate picked before HR ever posts the job, with referrals stacked up ahead of the application pile.

From there the conversation moves through the three stages of rejection, no reply, no interview, and no offer, and what each one actually tells you. Taylor argues the technical interview is on its way out in favor of proof of work, and that the question candidates should prepare for is not what you built but how it moved the needle. He shares his hot take that junior engineers now need to build something, get real users on it, and enter organizations closer to mid-level, illustrated with a student he mentored who did exactly that. Brittany connects it to the collapse of the old concentric circles of scope, where senior now carries what staff used to carry and everyone owns a project from day one.

The second half gets practical. Taylor walks through building a career.md file, a position by position brain dump of wins and real numbers, and using ChatGPT or Claude as the brain with personal AI assistants as the hands. He covers standardizing a resume template so AI output doesn't look generic, why AI slop is a function of what you feed it, and how to replace spray and pray with watchers, a shared Notion inbox, and contextual DMs to the people actually doing the hiring. His framing: use AI to get to the DMs faster, not to apply more.

On networking, he recommends opening your phone contacts before opening LinkedIn, having one to two conversations a week even when you're happy, and ten to fifteen a week when you're searching, because the effort you put in today pays off six to twelve months later. He makes the case that everyone should have a podcast or a 15 minute livestream, with a caution that outreach has to be contextual rather than cold. He also covers negotiation, where he prefers bullet points over scripts, keeping a separate compensation doc, always giving a specific reason for an ask, and being the last person to talk.

The episode closes with how Taylor maintains community at 500 to 1000 notifications a day, why he thinks human connection matters more in the AI era rather than less, a counterpoint about his brother who has built a great career without posting anything online, and a fun segment where everyone competes to be the worst AI career coach possible.

Taylor Desseyn has spent 15 years in tech recruiting, hosts the Guidance Counselor 2.0 podcast, and is VP of Global Community at Randstad Digital, powered by Torc.

Hosts

Overcommitted: https://overcommitted.dev

Brittany Ellich: https://brittanyellich.com

Erika Eggemeyer: https://github.com/eggyhead

Guest

Taylor Desseyn: https://tdesseyn.com

LinkedIn: https://www.linkedin.com/in/taylordesseyn/

Email: taylor@torc.dev

Taybot, Taylor's AI job search coach, text: 628-246-5885

Links

Tab: https://tab.bot/

Kiki: https://kikilabs.ai/

Boardy AI: https://www.boardy.ai/

Pally: https://pally.com/

Instinct: https://instinct.com/

Willow Voice: https://willowvoice.com/

Assistant Benchmark: https://assistantbenchmark.com/

React Summit: https://reactsummit.us/

Taylor's All Things Open talk in 5 bullets: https://taylordesseyn.beehiiv.com/p/the-whole-ai-job-search-talk-in-5-bullets