Is your job search outdated? 23+ tips for finding a GTM job in the AI era
Recent hires share insights from the frontlines
If you haven’t actively pursued a job offer in the last 12 months, then your approach to finding a job is outdated.
We’re living through a strange paradox in GTM hiring: It has never been easier to apply for a job, yet it has never been harder to get noticed. AI has commoditized the application process, making obsolete the way you found a job just a few years ago.
I wanted to understand this shift so I interviewed GTM leaders who recently signed offer letters. I asked them what AI tools and tactics they found most effective. I asked what they noticed is different about job searching today. Then I condensed down those answers for you below.
Some of their insights I found surprising; others are timeless fundamentals that matter more now than ever.
I hope you can put these insights to use find your next role.
Glen
What is the biggest shift you noticed in the hiring process compared to your last job search?
The power of your network - “AI makes it even easier to apply to online job postings. The way in was through my connections. I would not have landed this job without a connection on the inside.”
A bias for generalists & builders - “Many roles I explored in the past were quite niche but increasingly there’s demand for folks who can generalize across different types of partnerships and be fluid and flexible in how they work. There is more demand than ever for generalists and builders.”
Outreach directly to hiring managers - “One shift I noticed was the effectiveness of reaching out directly to the hiring manager to jump start an interview process. This could be because my network and relationships with hiring managers is broader than it was before when I found the process more recruiter driven, or it could be because companies have reduced their number of recruiters.”
Showcase your use of AI - “The same way so many companies are trying to showcase how they are AI-first, the same applies to job candidates. Personally, I did not find that hiring managers explicitly asked me about AI. So I found ways to work it into the conversation organically, to showcase something I built with AI at work or outside of work.”
The drawbacks of tenure - “Tenure is no longer an advantage when companies prioritize AI-driven efficiency above all. My experience deemed me as too expensive to get past some recruiter screens.”
What was the single most helpful AI tool or prompt you used during your job search? How did it help you?
AI job searching - “Checkout AI Apply and Jack & Jill. They harness AI for you to help you find jobs, enhance your resume, etc, like an AI-native version of Indeed or Linkedin jobs.”
Use LinkedIn search like an LLM - “The search bar on LinkedIn Jobs is now an AI prompt tool. Except the UI is rubbish so you don't know that. Treat it like you would ChatGPT, Claude or Gemini. Write as detailed a description of what kind of job you’re looking for and the results will be better.”
Interview prep - “I used AI for pre-interview research and post-interview follow-up. Before interviews I leveraged AI for deep research on a company and on the interviewer based on their role.I used AI to anticipate questions and prepare answers as well as organize my own questions.Then I would have it generate an interview prep-kit with everything I needed in one file for that interview.”
Resume-writing - “ChatGPT & Claude helped me tighten all of my writing around professional experience, which was a huge help.”
Interview storytelling - “I’d ask AI to review my resume and pose potential questions I might face and offer answers for me to consider using.”
What is a job searching tactic that may have worked in 2022 but feels obsolete today?
Cold applying on sites like Indeed and LinkedIn.
OTW - “I’m not sure if it ever worked, but the ‘Open To Work’ badge on LinkedIn I’ve never really been super comfortable with or bullish on.”
The elegant resumes - “The beautifully formatted resume is now a liability. Resumes must be optimized for ATS.”
Cover letters - “With AI, I think they have lost whatever limited weight they once carried.”
Hotmail - “This was true in 2022 but it’s even more true today: you aren’t likely to land a job at that hot company with your Hotmail or Yahoo email address. Use Gmail or a personalized email address (e.g. jane@janedoe.ai).”
In a market changing this rapidly, how did you validate that the company you chose to join is actually well-positioned for this AI era?
Diligence is tough - “Unless it’s an AI-native company, or a massive global org like Google, knowing what is real and what is vaporware is not easy. You can ask questions in the interview process, you can do your research, but its still not a guarantee.”
Kick the tires - “I did a significant amount of research into the company’s differentiation in the market coupled with the metrics: the company had A/B or lift-tested its predictive AI over 600 times, with real customers, against their BAU, and won nearly every time.”
The people - “I prioritize who I’ll be working with and for, so I put a lot of weight on the discussions I had with those leaders. I also sought out the opinions of people who are more deeply embedded (and invested) in AI to get their point of view on the companies I’m considering joining.”
The business model - “I didn’t do this expliclty. What I liked about my role is that it is selling shovels and jeans to the miners. Not a miner itself. Less dependent on the model or IDE of the day.”
Go with what you know - “I may have been at a slight advantage here as I have known the company and the co-founders for many years. I know the path they’ve been on to help define and drive how AI will be used in every size of business in the future.”
So much of job searching is still about making human connections (and NOT using AI). What is one thing you did in your job search unrelated to AI that you think made a difference?
Let your network know that you’re looking - “Simply letting my network know that I was looking to make my next move - this included former co-workers and current co-workers and partners (that I trusted to be discreet). When I saw a partnership leader that I respected move to a new company, I would reach out to congratulate them and also plant a seed that I’d be interested in having a chat if they’re planning to hire or build out a team.”
Thank you notes - “I still love a good ol’ thank you note after an interview. I tried to remember at least one personal piece of info from everyone I spoke with, and wove that into my thank you note.”
Connections at the top - “Human connections are still everything - if I didn’t know the co-founders and also hadn’t been a big advocate of the company since the early days, I’m not sure I would have landed this role.”
Never Search Alone - “I am a huge advocate of a program & book called Never Search Alone, by Phyl Terry. Phyl’s book is common sense guidance for anyone navigating a career pivot or job search, and he’s also built an enormous network of Job Search Councils, which meet regularly in small groups so people can help others who are going through similar journeys. I cannot advocate enough for the Never Search Alone program. You can get the book from the library and participate for free. I got more value from NSA than from any high-priced career coach or resume service.”
Anything else you want to offer other job searchers?
Start Now - “The best time to connect with that co-worker, a person you met at the conference, former classmate, etc. was yesterday. The second best time is now.”
Your network matters now more than ever - “You’ve got to activate your network of relationships. But make it easy for people to help you. Be specific about what you’re looking for and how you’d like that person to help.”
Do the work - “Using AI will only get you so far. It is really good for helping to structure your thoughts and for preparing for interviews, but it shouldn’t replace your thoughts. You will be interviewed by other humans, and they will be able to identify if you’re giving them AI-generated or insincere answers pretty quickly.”
Find meaning outside of your job search - “Job searching is an emotional roller-coaster. Find something outside of your job search to invest your time and energy to bring you joy and fulfillment, or at least serve as a distraction. Coach a youth team. Build a cabinet. Learn guitar.”
