Why the Best Don’t Get Hired

You might think the best candidate always gets the job. But in a competitive market, that’s often not true. The best candidate often loses to the one who looks like the perfect fit.

I recently tracked the job search of a Program Manager with years of experience in enterprise software. They had led large-scale programs, worked with high-profile clients, and successfully managed complex projects. They applied for a Program Manager role at an insurance tech SaaS company—a position that, at first glance, seemed like an easy win. But they didn’t get hired.

The reason? Their experience was in government clients, not insurance. Even though they had all the right skills, the company prioritized someone who had already worked with underwriting workflows and policy management software.

In a strong job market, companies hire people based on potential. But in a competitive market, hiring managers often choose the safest bet—the person who has done the job exactly as they need it.

The Harsh Truth: Good vs. Perfect Fit

When a hiring manager has thousands of applicants, they don’t ask:

• Who has the highest leadership potential?

• Who has the most impressive resume?

Instead, they ask:

• Who has already done this job in this industry?

That’s how great candidates lose to someone with a narrower—but more specific—background.

How to Make Yourself the “Perfect Fit”

If you’re struggling to land roles, it’s may not be because you’re unqualified—it’s because you don’t look like the safest bet. Here’s how to fix that:

1. Mirror the Job Description in Your Resume & LinkedIn

• Hiring managers scan for exact wording from the job description.

• If the job says “managing cross-functional teams for SaaS deployments”, and you’ve done something similar, don’t just say “Led technical teams”—instead, write: “Led cross-functional teams to deploy SaaS solutions”

• The closer your language is to what they’re looking for, the better.

2. Research Industry Jargon & Key Terms

• Look at job listings in your target field to see what terminology appears frequently.

• Search LinkedIn profiles of people currently in your target role and study how they describe their work.

• These terms often include industry-specific acronyms or core responsibilities like "underwriting processes" or "SaaS compliance"—make sure they appear in your resume and LinkedIn profile.

3. Adjust Your Job Titles If Necessary (Without Lying)

• Some companies use unique titles that don’t translate well.

• If your title was “Technical Program Owner”, but the industry standard is “Technical Program Manager”, update it on your resume for clarity.

• Just ensure it accurately reflects what you did.

4. Gain Relevant Experience—Fast

If your background doesn’t exactly match the industry you’re targeting, here’s how to quickly gain relevant experience:

A. Get Real Projects (Even Without a Job)

• Freelance / Contract Work – Find small projects through Upwork, Fiverr or direct outreach to companies.

• Volunteer for a Startup or Open-Source Project – Many startups need help but can’t afford full-time hires.

• Unpaid Projects – Build a portfolio site, case study, or prototype showcasing your work.

B. Use Your Current Job to Build Experience (If You Have One)

• Work on a Cross-Department Project – Find ways to collaborate with teams in your target field.

• Automate Tasks – Use scripting, analytics, or tech solutions to improve workflows.

• Partner with IT or Engineering – If you’re in a non-tech role, volunteer for tech-related tasks to gain industry exposure.

C. Certifications (Only When They Make a Difference)

• Only pursue certifications that hiring managers value.

• Worth it? AWS, Scrum, PMP, industry compliance (e.g., HIPAA for healthcare tech).

• Not worth it? Random online courses with no hiring impact.

5. Networking Can Differentiate You & Get You Introductions

• Cold applications often get lost in the pile. Warm introductions make a huge difference.

• Ways to get referrals:

  • Reconnect with old colleagues who now work in your target field.

  • Ask for an intro through LinkedIn (send a polite DM).

  • Attend local or virtual industry meetups and network.

• Hiring managers are far more likely to take a chance on someone referred by a trusted connection.

6. Control the Narrative of Your Application

• Be clear about why you’re a fit and make sure others can easily see it.

• If your resume, LinkedIn, and interview answers send mixed signals, hiring managers will hesitate and decline.

• Tell a consistent, compelling story that positions you as the perfect fit for the role.

  
  

Final Thoughts: Positioning is Everything

You don’t need to fake experience—you need to connect the dots for hiring managers. If your resume, LinkedIn, and interview answers send mixed signals, they’ll reject your application.

Make it clear why you’re the perfect fit and ensure your entire application tells a consistent, compelling story that aligns with the role. The easier you make it for hiring managers to see you as the safest, most obvious choice, the more likely you’ll land the job.

I’m launching a new podcast at applicationowl.com/coaching. If you're interested in a free consultation on how to position yourself as the perfect fit, check it out.