63 AI Job Search Tools – Which ones to trust and use carefully
Plus a sales leader's breakdown of his 57-day job hunt (must-read!)
This week’s edition is packed with AI tools changing the job search game, strategic approaches to job hunting, and deep dives into salary negotiation tactics.
📌 Reminder: The Notion Job Tracker is live! Track your applications, stay organised, and automate follow-ups. Grab it here, and let me know how it’s working for you!
🎙 New Open To Work Podcast Episode
How to stand out when applying for roles at top companies
This week, Matthew is joined by Mews CEO, Matt Welle, to discuss:
⤷ What impresses hiring managers during interviews
⤷ How to stand out in competitive hiring processes
⤷ Why diversity matters & how Mews approaches it
⤷ Strategies to stay one step ahead in your job search
🎧 Listen on Spotify
▶️ Watch on YouTube
What’s happening this week?
⤷ The 63 AI job search tools you need to know
⤷ A sales leader's breakdown of his 57-day job hunt (a must-read!)
⤷ How one Candidate landed 4 offers in 45 days—step-by-step approach
⤷ Deep dive: Salary negotiation strategies that work
Featured Post: The 63 AI Job Search Tools You Need to Know
By Aakash Gupta
AI is reshaping job searching.
Exercise caution. I would treat some of the tools mentioned with Aakash with a degree of scepticism. New platforms are introduced every week. Some will help, and others might hinder you.
There are two areas I would approach with a warning.
⤷ Some candidates are using AI interview co-pilots that suggest answers in real-time. I don’t know how they can read and look like they know what they’re talking about in real-time, but hey, ho.
⤷ AI tools can mass-apply jobs for you and optimise your resume. - The question you have to ask yourself is if you want to give up ownership of this. Think twice.
Aakash spent 3 weeks testing 63 AI-powered job search tools to see which ones work, and it makes for an interesting read. You’ll see in a later post that Dan used massapply - and I would be interested to see his takeaways about that specific tool.
Key categories covered which are more of interest for you to look at:
⤷ AI tools for finding jobs & sending cold outreach
⤷ Resume optimisation & ATS hacks
⤷ Interview preparation & AI coaching
⤷ AI co-pilots for networking
AI is changing how candidates apply, Interview, and negotiate, which will happen sooner or later.
Please let me know if you have any experience with these tools or would like us to explore this further.
Notion Job Tracker is Live!
If you're tired of manually tracking job applications, this tool helps you:
⤷ Stay organised with a clear dashboard
⤷ Automate follow-ups so you never miss an opportunity
⤷ Track job applications without messy spreadsheets
📌 Reminder: Clear the existing data before using it! Let me know if you need a walkthrough video.
A Sales Leader’s 57-Day Job Hunt Breakdown
By Dan Dougherty
Dan treated his job hunt like a sales pipeline—and landed 4 job offers in 57 days. Here’s how he did it:
⤷ 200+ targeted companies identified using Crunchbase & LinkedIn
⤷ 70 cold emails sent (11 directly to CEOs!)
⤷ 17 interviews from cold outreach
⤷ 4 job offers in under 60 days
Key takeaways:
⤷ Treat your job search like a sales process (prospect, outreach, follow-up)
⤷ Test multiple resume versions to see which gets better responses
⤷ Track everything in a spreadsheet to measure progress
This wasn’t a spray-and-pray strategy. Dan ran his job search like a highly optimised sales process.
1️⃣ Researching & identifying target companies
Dan started by prospecting 200-250 companies using Crunchbase and LinkedIn.
Here’s how he broke it down:
⤷ Used Crunchbase to find recently funded startups with hiring needs
⤷ Filtered LinkedIn job searches to uncover relevant roles
⤷ Researched leadership teams to identify hiring decision-makers
⤷ Prioritised companies that aligned with his skills & experience
Why this works:
Focuses on companies actively growing & hiring
Targets leadership teams to make direct connections
Saves time by avoiding companies with hiring freezes
2️⃣ Optimising his Resume & outreach strategy
Instead of sending out a single generic resume, Dan:
⤷ Created 5-6 different resume versions to test formatting & keyword optimisation
⤷ Used ATS resume scanners (Rippling, Kickresume, Enhancv, Massive) to improve match rates
⤷ Wrote personalised cold emails to hiring managers & CEOs
⤷ Tracked responses to analyse what worked best
Results from cold outreach:
70 targeted cold emails sent (11 directly to CEOs!)
24.3% overall response rate
36.4% response rate from CEO outreach
Why this works:
Multiple resume versions increased his chances of passing ATS filters
CEO outreach had the highest response rate—going straight to the top works!
Tracking responses helped refine messaging for better results
3️⃣ Interviewing & converting to offers
Dan didn’t just focus on getting interviews—he tracked & optimised his conversion rates at every stage.
His full breakdown:
⤷ 17 first-round interviews (from cold outreach alone!)
⤷ 10-second interviews
⤷ 7 third-round/case study interviews
⤷ 4 job offers received
Key Interview Conversion Rates:
First → Second Interview: 35.3%
Second → Job Offer: 66.7%
Third Interview → Job Offer: 57.1%
Why this works:
Tracking progress like a sales pipeline helped refine his approach
High CEO response rates led to faster interview cycles
Prepping multiple resume versions ensured he had the right one for each role
4️⃣ Tools & subscriptions he used
Dan didn’t rely on free job boards—he invested in paid tools to optimise his search.
Subscriptions that helped him win:
⤷ Crunchbase – For prospecting high-growth companies
⤷ Pavillion – Executive networking group
⤷ LinkedIn Premium – To get direct access to hiring managers
⤷ Kickresume.com & Enhancv.com – Resume optimisation
⤷ UseMassive.com – Auto-applying to jobs - again, be careful.
⤷ Hunter.io – Finding hiring manager emails
Why this works:
Investing in research tools gave him access to better opportunities
LinkedIn Premium helped him message hiring managers directly
Resume tools ensured he was getting past ATS filters. Side note: I question this last statement here, and I wanted to keep it in. There is no such thing as ATS filters.
5️⃣ Key Takeaways for Job Seekers
Dan’s process proves job hunting isn’t just about applying—it’s about strategy.
What worked best for him:
⤷ Cold outreach to CEOs & hiring managers had the highest success rate
⤷ Tracking his progress helped him refine and optimise along the way
⤷ Investing in tools gave him an edge over other candidates
⤷ Resumes need to be tailored & optimised for each role
His advice to job seekers:
“Don’t just send out a million resumes—be strategic.”
“Follow up with hiring managers and decision-makers.”
“Treat your job search like a sales funnel—track everything.”
“Take calls, even if they don’t seem useful—you never know.”
📌 How one Candidate landed 4 offers in 45 Days
By Cecilia Haynes
Cecilia applied 85 times and landed 4 offers.
Here’s exactly what she did to maximise her chances:
⤷ Created a video resume to stand out
⤷ Built a project portfolio to showcase past work
⤷ Followed up on every application with direct outreach
⤷ Used LinkedIn search to target hiring managers & recruiters
Her results:
85 applications → 49 interviews → 4 offers
Average time from application to offer: 12-35 days
Minimal reliance on networking—mostly cold applications!
📄 Read Cecilia’s full breakdown
Find everything on the Open To Work Toolkit
The toolkit is live and evolving. Let me know what’s working for you and what needs improvement.
Here’s to a successful job search in 2025.
Warm regards,
Matthew Parker
Founder of Open To Work Community
Darren Bush
Founder of Open To Work Toolkit
www.gethiredtoolkit.com |