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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.





Over the last year, hiring teams have started seeing a wave of new job titles pop up across tech, sales, and operations.
Some are legitimate new roles.
Others are existing jobs with a slightly different name.
And many of them have one thing in common: AI is suddenly part of the job description.
From Go-to-Market Engineers to AI Specialists, companies are experimenting with new roles as they figure out how automation and AI fit into their teams.
But most of these positions aren’t entirely new. They’re evolutions of existing roles.
One role that is gaining traction is the Go-to-Market Engineer.
Depending on who you ask, it is either:
In practice, it is a bit of both.
As Matt Tokarz recently pointed out after closing a search for an Outbound & Go-to-Market Specialist, the role looked very different from traditional RevOps. The focus was not reporting or CRM hygiene. It was building prompts, leveraging tools like Clay and Smartlead, and enabling SDRs and AEs with backend insights to accelerate pipeline growth.
Instead of traditional RevOps work like reporting and CRM management, the focus was on:
The goal was not simply managing sales data. It was accelerating pipeline generation through automation.
One trend is becoming clear. Companies are not replacing entire departments with AI.
Instead, they are changing how existing roles operate.
Sales teams still need pipeline.
Marketing teams still need content.
Engineering teams still need to build software.
The difference is that employers now expect candidates to use AI tools as part of their workflow.
As Zac Colip noted during the discussion, we are currently in a transitional phase where companies are labeling roles with “AI” as they experiment with how the technology fits into teams.
But that may not last forever.
Right now, AI still feels new enough that companies highlight it in job titles.
But eventually, AI will likely become a baseline expectation, not a specialty.
Think about it like cloud technology or data analytics.
At first, companies hired “cloud specialists.” Now most engineers are expected to understand cloud infrastructure.
The same shift will likely happen with AI.
Instead of hiring “AI-enabled marketers” or “AI engineers,” companies will simply expect employees to know how to work with AI tools.
One challenge with these emerging roles is simple: there aren’t many candidates with real experience yet.
Many of these positions didn’t exist two years ago.
In one recent search, we started looking for a candidate locally in Chicago. Eventually we expanded nationwide because the pool of people with relevant experience was extremely limited.
This is a common issue with emerging roles:
That gap will likely persist for the next few years.
Another noticeable shift is that roles are becoming more hybrid.
Instead of hiring for narrow responsibilities, companies are combining multiple functions into one position.
As Matt Mulcahy highlighted, one example is the rise of Forward Deployed Engineers, a model popularized by Palantir.
These engineers:
What used to involve several roles, including product managers, engineers, and solution architects, can now sometimes be handled by one person. AI development tools are part of what makes this possible.
Not every industry is moving at the same pace.
As Ashley DuBois pointed out, some sectors, such as transportation, are applying AI to specific workflows like load booking and operational automation.
At the same time, some companies are adding “AI” to job titles even when the core responsibilities remain largely traditional.
In many cases, it is still essentially an IT manager role with AI familiarity layered in.
This reflects a broader transition period where companies want to signal modernization and candidates want to signal relevance.
In logistics, AI is increasingly handling scheduling, tracking, and coordination tasks.
According to Brittany Lasky, operational roles such as logistics coordinators may experience the greatest impact from automation.
However, freight brokers who manage negotiation and strategic RFPs remain in demand.
AI can optimize processes. It does not replace relationship management or strategic negotiation.
Across industries, a pattern is emerging.
Execution becomes automated. Strategy becomes more valuable.
Automation is also reshaping finance and accounting roles.
As Adam Slater noted, accounts receivable jobs that once focused on high-volume manual processing are evolving into more analytical positions centered on reporting and insights.
The work is not disappearing. The expectations are increasing.
Organizations are now hiring for:
Even roles traditionally considered administrative now require deeper technical capability.
AI is not eliminating analyst roles. It is expanding them.
Financial analysts are also expected to understand tooling, sourcing, and data transformation.
In many cases, two or three roles are being combined into one.
This raises a long-term question.
If entry-level roles become more complex or disappear entirely, how will organizations develop senior talent in the future?
The traditional model of high-volume cold calling is changing.
According to Jack Smith and Emily Canna, teams are shifting toward:
At the same time, companies are moving away from activity-based KPIs and focusing more on outcomes such as demos set and SQLs generated.
In a market saturated with automated outreach, authentic communication has become a competitive advantage.
Several clients have said it directly. They want a human in the seat.
Every six to twelve months, hiring trends in go-to-market teams shift.
As Jennifer Salerno noted, companies move through cycles.
One quarter it is BDRs.
Then RevOps.
Now it is go-to-market engineers.
Many companies experimented heavily with AI to accelerate pipeline generation.
What those experiments exposed were structural gaps, particularly in outbound strategy.
AI can support execution. It does not replace a well-built top-of-funnel engine.
Inbound momentum can hide weaknesses. Outbound forces clarity.
The companies gaining traction right now are not chasing trends. They are rebuilding the fundamentals of their go-to-market strategy.
For employers, the takeaway is straightforward. Job descriptions and expectations need to evolve alongside technology.
Across functions, we are seeing the same shift play out. AI is not eliminating entire roles. It is changing how those roles operate and increasing the baseline skill set required to perform them well.
Hiring managers should start thinking less about traditional titles and more about capabilities. That often means prioritizing candidates who can:
In many cases, the perfect candidate with the exact title simply does not exist yet. The strongest hires are often people who have developed adjacent skills and shown the ability to adapt as the tools evolve.
The broader trend is that AI is accelerating a shift that was already underway.
Roles are becoming more hybrid. Expectations are increasing across nearly every function. And repetitive tasks are being automated, leaving more strategic work behind.
Sales teams still need pipeline.
Operations teams still need coordination.
Finance teams still need reporting and analysis.
Engineering teams still need to build software.
What is changing is how the work gets done and what skills are required to do it well.
Right now we are in a transitional phase where companies are still labeling roles with “AI” as they experiment with new workflows and technologies.
Over time, that label may disappear.
AI will simply become part of how work gets done.
And the roles themselves, while evolving, will look more familiar than the titles might suggest.