When Evaluating Candidates, How do you Seperate the Pretenders from the Real Thing?

Insights from one of Hirewell’s clients, Affirm
Mar 24, 2020
Jeff Smith
Jeff Smith
Managed Recruiting
evaluating sales candidates

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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




1. What is your sales process? Every successful salesperson has a bullet-proof sales process that they adhere to because it has garnered them positive results. I am usually leery of a candidate who is unable to articulate his process clearly and concisely - a successful salesperson relies on this process to deliver results.

i.e. Focusing on prospects with best fits (former customers or partnered w/ competitor), intro/scoping call - to understand what they like/dislike about you/competitor, demo call honing on that "reason" they like/dislike you/your competitor, Follow-up/Negotiation call followed before contract signing.

2. Describe a time when you failed/lost a deal?

This question lets me know if this candidate is self-aware, accountable and has a growth mindset. All successful sales people have made mistakes, miscalculated and lost deals before - even the best. The key is knowing if they owned the mistake, learned from it and ensured not to repeat it. One thing that gave me great confidence working with prospects as an IC was knowing that every opportunity was a learning opportunity. Great sales people approach their work with Nelson Mandela's quote at heart... "I Never Lose. I Either Win Or I Learn".

Ni Adesokan | Sales Manager




When evaluating sales candidates, I look for someone who listens and asks questions more than they talk about themselves.  I also can't stand when a candidate responds to the question, "why and how did you originally get into sales?" by saying, "I'm a people person and was always told by friends and family that I should be in sales."  For me, this response is indicative of someone who relies on personality and charm, instead of hard-work and a thorough knowledge of their customer's business.

Andrew Sawch | Sales Manager



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

Jeff Smith
Jeff Smith
Managed Recruiting

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