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Affirm is a financial technology company that empowers shoppers to buy the items that they love and pay for them over time in a way that best matches their monthly budgets. It was founded in 2013 by PayPal co-founder, Max Levchin and Palantir co-founder, Nathan Gettings.
Affirm HQ might be in the Bay Area, but their roots are everywhere. When they decided to aggressively grow their team in Chicago, they came to us to help partner with them on their Sales, Customer Success and IT Engineering hiring locally. They wanted a partner that knew how to win the ground game in Chicago and had intimate knowledge of the market. We, naturally, always want clients like Affirm, so it was a win/win!
We asked some of Affirm’s sales leaders to share insights on how they find top sales candidates. Here are a few questions their team always asks during the interview process to separate the talkers from the real deal.
Candidates who are the “real deal” will talk the talk when it comes to sales chops. If asked “how do you prioritize your pipeline?,” they’ll be able to clearly articulate exactly how they determine who to reach out to first, second, etc…, and why.
Folks might say that they like to make calls, or that they like to help others, but people who understand sales know that it’s all about the activity and the numbers. They have a thought-out and methodical approach to filling the pipeline and staying on top of prospects for the close.
I also find that people who get sales demonstrate their skills during the interview with questions like, “what reservations do you have about me, if any?” or “what are the next steps?”. It can actually put the interviewer on the hot seat, but that’s great! Using every interaction to move toward the close is a fundamental skill for successful salespeople.
Alisha Johnson | Sales Manager
Having worked at the intersection of technology and travel for 10 years now, my favorite question to ask reps is, “What excites you about selling to the travel vertical?” You wouldn’t believe how many answer with a short, “oh because I LOVE to travel” or share tales from their favorite trip. Most people I know love to travel and have many memorable travel tales, but I’ve met many people who don’t like selling to the travel vertical because it’s hard, nuanced, and can be very slow to adopt new technology. Candidates who share stories of their previous travel partners, selling wins, and especially losses typically resemble the “real thing” and catch my attention.
Johnston Gilfillan | Sales Manager, Travel
Affirm is a financial technology company that empowers shoppers to buy the items that they love and pay for them over time in a way that best matches their monthly budgets. It was founded in 2013 by PayPal co-founder, Max Levchin and Palantir co-founder, Nathan Gettings.
Affirm HQ might be in the Bay Area, but their roots are everywhere. When they decided to aggressively grow their team in Chicago, they came to us to help partner with them on their Sales, Customer Success and IT Engineering hiring locally. They wanted a partner that knew how to win the ground game in Chicago and had intimate knowledge of the market. We, naturally, always want clients like Affirm, so it was a win/win!
We asked some of Affirm’s sales leaders to share insights on how they find top sales candidates. Here are a few questions their team always asks during the interview process to separate the talkers from the real deal.
Candidates who are the “real deal” will talk the talk when it comes to sales chops. If asked “how do you prioritize your pipeline?,” they’ll be able to clearly articulate exactly how they determine who to reach out to first, second, etc…, and why.
Folks might say that they like to make calls, or that they like to help others, but people who understand sales know that it’s all about the activity and the numbers. They have a thought-out and methodical approach to filling the pipeline and staying on top of prospects for the close.
I also find that people who get sales demonstrate their skills during the interview with questions like, “what reservations do you have about me, if any?” or “what are the next steps?”. It can actually put the interviewer on the hot seat, but that’s great! Using every interaction to move toward the close is a fundamental skill for successful salespeople.
Alisha Johnson | Sales Manager
Having worked at the intersection of technology and travel for 10 years now, my favorite question to ask reps is, “What excites you about selling to the travel vertical?” You wouldn’t believe how many answer with a short, “oh because I LOVE to travel” or share tales from their favorite trip. Most people I know love to travel and have many memorable travel tales, but I’ve met many people who don’t like selling to the travel vertical because it’s hard, nuanced, and can be very slow to adopt new technology. Candidates who share stories of their previous travel partners, selling wins, and especially losses typically resemble the “real thing” and catch my attention.
Johnston Gilfillan | Sales Manager, Travel
If you have any further questions or want more insights on vetting salespeople, feel free to contact me at jeff@hirewell.com or find me on LinkedIn.
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If you’re hiring in 2026, you’re dealing with two realities at the same time.
First, traditional signals like degrees and pedigree are losing their value.
Second, Gen Z is reshaping expectations around speed, transparency, and trust.
Together, those forces are pushing talent acquisition into its next evolution.
As we outlined in Agentic HR Is Here: What Talent Acquisition Really Looks Like in 2026, recruiting is becoming more autonomous at the execution level. But autonomy alone doesn’t solve the core hiring problem.
You still need a better way to evaluate people.
That’s where skills-first hiring comes in.
The Degree Barrier Is Collapsing
For decades, degrees were used as a shortcut.
Not because they reliably predicted success, but because they reduced perceived risk and simplified decision-making.
That logic no longer holds.
Roles are changing too fast. Job titles mean less than they used to. And in a market where AI can generate a polished resume in seconds, pedigree is an even weaker signal.
Companies need capability, not credentials.
Skills Intelligence Is Becoming the New Operating System
The bigger shift isn’t just skills-based hiring. It’s skills intelligence.
Instead of organizing work around static job descriptions, companies are starting to think in terms of capabilities. Work is assigned based on skill, not hierarchy or tenure.
This is the same evolution happening across workforce planning more broadly. Not headcount planning, but capability planning.
And it’s the only model that holds up in a fast-moving market.
Why Skills-First Hiring Is Accelerating Right Now
Skills-first hiring is gaining traction because it solves multiple problems at once.
It improves quality of hire.
It increases internal mobility.
It reduces bias tied to pedigree.
And it aligns better with how work actually gets done.
But it’s also accelerating for a more practical reason.
The resume is no longer reliable.
As we covered in The AI-on-AI Hiring Arms Race, recruiting teams are now dealing with a flood of highly optimized, AI-generated applications. Many look great on paper and collapse under real scrutiny.
When that happens, skills-based evaluation stops being a “nice to have.” It becomes the only way to restore signal.
Gen Z Is Forcing the Issue
Now layer in Gen Z.
By 2026, Gen Z is one of the fastest-growing segments of the workforce. They are also the least tolerant of slow, opaque hiring processes.
One of the most important data points in the market right now is this:
A majority of Gen Z candidates will drop out if a hiring process exceeds 22 days.
Speed, to them, isn’t about impatience. It’s about competence.
If a company can’t run a clear, efficient hiring process, candidates assume it can’t run the business well either.
Ghosting Is No Longer a Candidate Experience Issue
It’s a trust issue.
A large percentage of job seekers report that looking for work negatively impacts their mental health. The biggest driver isn’t rejection.
It’s silence.
Waiting to hear back. No closure. No clarity on next steps.
For Gen Z, that lack of transparency is a dealbreaker. It signals misalignment, not just poor communication.
In 2026, how you hire is inseparable from how you’re perceived as an employer.
The New Hiring Deal in 2026
For Gen Z, the hiring experience is part of the offer.
They expect:
- speed and clear timelines
- skills-based evaluation
- consistent communication
- honest feedback
- values alignment
If the process feels like a black box, they assume the culture is the same.
This is where skills-first hiring and agentic systems intersect. Technology can speed up execution, but only leadership can ensure the experience remains human.
What Talent Leaders Should Be Doing Now
The companies adapting fastest in 2026 are focused on a few fundamentals:
- Shortening the hiring process
By removing unnecessary steps, not by cutting corners. - Shifting from resumes to proof
Work samples, structured interviews, and skills assessments matter more than pedigree. - Improving transparency
Candidates don’t need perfection. They need clarity and closure. - Designing hiring for humans
Technology should reduce friction, not replace basic respect.
Final Thought
Skills-first hiring isn’t just about fairness. It’s about accuracy.
And Gen Z isn’t asking for special treatment. They’re forcing employers to modernize a hiring process that’s been broken for a long time.
The companies that adapt will hire better, faster, and with less churn. The companies that don’t will keep blaming the market while losing candidates to competitors who simply run a better process.
Most companies agree with skills-first hiring in theory. Very few have operationalized it in a way that actually improves outcomes. If you want help redesigning your hiring process for 2026, especially around skills-based evaluation and candidate experience, we can help. Reach out and we’ll walk you through what’s working right now.
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