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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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Plenty has been written about AI over the past two years. For much of that time, AI has been more hype than reality. I THINK 2026 is when that starts to change.
Here’s the first in a three part series of where we see AI going in the recruiting world.
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For the last few years, most companies treated AI like a recruiting assistant. It helped draft job descriptions, summarize resumes, and speed up outreach. Useful, sure. But it didn’t fundamentally change how hiring worked. And oftentimes, things needed to be double checked before hitting send.
I think that’s going to change.
In 2026, we’re seeing the rise of agentic HR. These are systems that don’t just support recruiters. They can execute work autonomously inside defined guardrails.
That shift is forcing talent leaders to rethink what recruiting teams are actually responsible for and what still requires a human.
From Copilot AI to Agentic Recruiting Systems
Traditional recruiting AI waited for humans to click “next.”
Agentic systems don’t.
They can interpret real-time funnel data, align to hiring goals, and take multi-step action. That includes adjusting sourcing spend, coordinating interview schedules, and triggering workflow changes without manual oversight.
This isn’t automation layered onto old processes. It’s the early version of a self-driving recruiting function.
The Metric That Matters More Than Time-to-Fill
Time-to-fill and cost-per-hire still matter. They just don’t fully capture what’s changing.
A concept showing up more in 2026 is Return on Autonomy. It measures the value created when humans and autonomous systems are paired intentionally.
In plain terms, the question is simple.
Are we using technology to eliminate busywork, or are we just doing the same work faster?
Because speed doesn’t help if it leads to worse decisions, a weaker candidate experience, or more noise in the funnel.
Why This Changes the Role of TA Leadership
As agentic systems absorb transactional work like screening, scheduling, and coordination, the role of recruiting leadership shifts.
The best TA leaders are spending less time managing process and more time doing what actually drives hiring outcomes. That includes aligning hiring to business priorities, building trust with candidates, and improving decision quality.
The real opportunity of 2026 isn’t more AI. It’s that recruiters finally get to focus on the work that requires being human.
The Mistake Companies Are Making Right Now
Here’s the trap.
Companies adopt advanced recruiting technology but keep the same habits. Long approval chains. Inconsistent communication. Unclear evaluation criteria.
When that happens, speed increases, but trust collapses.
Candidates don’t experience innovation. They experience silence, confusion, and a process that feels even more impersonal than before.
In 2026, the human experience of hiring is becoming a differentiator again because so many companies are getting it wrong.
What Talent Leaders Should Be Thinking About Now
You don’t need a total rebuild tomorrow. But you do need clarity.
The companies winning in 2026 are asking the right questions.
What parts of our hiring process truly require human judgment?
Where are we slowing things down out of habit?
Are recruiters trained for strategic work, or just process management?
Do our systems increase transparency, or just efficiency?
These aren’t technology questions. They’re leadership questions.
What’s Next
Agentic HR is changing how recruiting works. It’s also creating a new challenge.
As employers deploy autonomous systems, candidates are doing the same. The result is an emerging AI-on-AI hiring arms race that’s flooding pipelines with highly optimized but low-trust applications.
Next in this series: The AI-on-AI Hiring Arms Race and How to Protect Hiring Quality Without Breaking Trust
A lot of companies are going to try to AI their way into faster hiring this year and still end up with worse results. If you want to build a recruiting model that actually works in 2026, one that balances speed, quality, and credibility, we can help. Reach out if you want a second set of eyes on your hiring approach.
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