The 2025 job market is a hiring wasteland. Funding cuts everywhere. Organizations restructuring. Even seasoned professionals with decades of experience are finding themselves competing for the same positions.
And most of us are still job searching like it's 2019.
We're polishing resumes, applying blindly to job boards, and wondering why we're getting ghosted. Meanwhile, artificial intelligence has fundamentally changed how we can approach career transitions—if we know how to use it strategically.
Laura Wigglesworth, who transformed recruiting operations at major humanitarian organizations, partnered with me to outline a seven-step process that flips traditional job searching on its head.
Step 1: AI Identifies Your Accomplishments
We all struggle with this. What exactly counts as an accomplishment when you've spent years working in complex, multi-stakeholder environments where success isn't always quantifiable?
Here's where ChatGPT becomes invaluable. Copy your current resume and paste it in with this prompt: "What are my top career accomplishments based on this resume?"
The AI will identify patterns you might miss. When Laura tried this, ChatGPT highlighted three points in seconds:
Transforming the global recruiting team and function at CARE
Launching an executive search division within FHI 360
Establishing a boutique search firm for NGOs.
But here's the crucial part: every accomplishment needs numbers. If you're struggling to quantify your impact, ask ChatGPT: "What numeric values should I have to validate these different activities?" It will suggest where to add metrics, then you can research the actual numbers.
Step 2: Extract Your Marketable Skills
Your accomplishments tell a story. Your marketable skills are what employers will actually pay for.
These always start with action verbs and explain how you accomplish things, like "building high-performing recruiting teams" and "reducing time-to-fill by 42%."
For those of us in humanitarian work, this might translate to:
Designing nationwide crisis response protocols
Leading cross-functional teams in high-risk environments
Managing multi-million dollar contracts
Feed these skills back to ChatGPT with: "Based on these marketable skills, what jobs can I do?"
Step 3: Discover Roles You Never Considered
This is where it gets interesting. ChatGPT doesn't just suggest obvious humanitarian roles—it connects your skills to private sector opportunities you might never have considered.
Crisis response experience? That translates to business continuity planning, risk management, and emergency preparedness roles across industries.
Program management in complex environments? Think project management in tech, healthcare, and consulting.
For broader exploration, try Google's Career Dreamer tool. It shows interconnected career paths and helps you visualize how your humanitarian experience opens doors beyond traditional NGO work.
Use Perplexity to get specific. Search for "mission-driven companies focused on health outcomes that are stable and hiring." Refine with follow-up questions about company size, geographic focus, or specific impact areas.
Step 4: Build Strategic Networks
Forget random LinkedIn connection requests. Use AI to identify specific people worth knowing.
Try this prompt with Happenstance: "Who at [target organization] has worked at [your previous organization] or went to [your university]?" This gives you natural conversation starters and shared experiences to reference.
LinkedIn's advanced search becomes powerful here. Search for your target role and filter by first-degree connections. These people can provide insider perspectives or introduce you to decision-makers.
Don't overlook second-degree connections. As I noted, we're all connected within six degrees. Someone you know probably knows someone at your target organization.
Step 5: Test Before You Commit
Most career advice fails when it assumes you know what you want. In reality, many roles look different from the inside.
Before investing months pursuing a direction, test it through informational interviews. But don't wing these conversations.
Ask ChatGPT: "What are 10 unique, interesting questions about [specific role] that aren't normal Google searches? What are 10 thoughtful follow-up questions? What will I learn from each question?"
This gives you a framework for deeper conversations that reveal whether a role truly fits your interests and values.
I tested three different career directions before finding my current path. There's no shame in discovering a direction isn't right for you—it's data that prevents future misery.
Step 6: Optimize Your Applications
Notice we're just now talking about resumes. That's intentional.
Don't apply to jobs unless you've done the research and have some connection to the organization. Otherwise, you're resume number 382 in a pile that never gets reviewed.
When you do find the right opportunity, tools like Hiring Coach AI can tailor your resume and cover letter to specific job descriptions. It suggests relevant terminology and helps you choose which experiences to highlight.
The platform also includes interview preparation with practice questions tailored to your background and the specific role. You can record yourself answering questions and get feedback on your delivery—crucial since most of your preparation has been text-based but interviews are verbal.
Step 7: Network Your Way In
Most positions are filled through word-of-mouth, not job boards. You want to be an “internal” candidate when permanent roles open.
One way to do that is by networking with hiring managers or their influencers, well in advance of the job ad. It takes six months for most job ads to be posted. The hiring manager spends the first three months making the case for the position, and then another three months wrangling with HR.
You have six months to connect with them and be the person they have in mind as they move the job description along to publication.
Another great way to network your way in is during informational interviews. Be sure to ask: "What challenges are keeping you up at night?" You've just identified potential consulting opportunities.
Most organizations can hire consultants faster than employees—weeks instead of months. Every external applicant will get compared to your already-proven performance.
The Hard Truth About Modern Job Searching
Some people do get hired by sending resumes blindly to hundreds of companies. But that's 50 or 100 or a thousand applications before something happens.
My fragile mind could not handle that when I was unemoployed. We are already dealing with enough rejection and uncertainty.
The tools exist. The strategies work. Use this AI-powered approach to focus your energy on quality connections and strategic positioning rather than playing a numbers game.
The question is whether you’re willing to adapt your approach to how hiring actually happens in 2025.
I created these toolkits for career pivoters who are done wasting time. Especially introverts who want to get jobs faster. These toolkits help you:
Craft better resumes and cover letters that excite recruiters.
Design LinkedIn profiles that hiring managers love.
Connect with decision makers using power-mapping prompts.
Handle ghosting (and bounce back fast).
These are the practical playbooks I wanted when I was unemployed and hearing nothing but silence.
These toolkits are free to annual paid Career Pivot subscribers.
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