How to Break Into AI Sales
When Companies Say "No AI Experience, No Hire"
The catch-22 that's keeping great salespeople out of the most lucrative sales market – and how to beat it
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A hiring manager recently told one of my candidates, "You've got 12 years of enterprise software sales experience and crushed every quota, but you've never sold AI, so we're going with someone else."
Sound familiar?
If you're tired of being rejected from AI sales roles because you haven't sold AI before – which is impossible since the industry barely existed five years ago – you're not alone. And more importantly, you're not stuck.
I'm going to show you exactly how to overcome the most significant hiring bias in tech sales right now, and why this ridiculous catch-22 is your most important opportunity.
The Insanity of AI Sales Hiring Right Now
What I'm seeing in AI sales hiring is insane. Companies are desperate for talent, posting roles with $200K to $500K OTEs, but then they reject incredible candidates because they want someone who's already sold their exact AI product.
It's like saying "We need someone with 10 years of iPhone sales experience" in 2008. The math doesn't work.
But here's what I've learned after working with hundreds of sales professionals: The companies that are winning right now aren't the ones waiting for perfect AI sales unicorns – they're the ones smart enough to hire great salespeople and teach them AI.
So how do you get in front of those smart companies?
Strategy 1: Flip the Script on "AI Experience"
The Reality: This bias exists, but it's not universal, and it's creating a massive opportunity for salespeople who know how to navigate it.
I recently worked with a candidate – let's call him David. Ten years of selling manufacturing equipment. Incredible track record, but every AI company kept saying the same thing: "We need someone who understands AI sales cycles, AI buyers, AI objections."
So instead of fighting that bias head-on, we got strategic.
David started researching how AI was transforming manufacturing. He learned about predictive maintenance, quality control algorithms, and supply chain optimization. But here's the key – he didn't try to become an AI expert. He became an expert on how AI solves manufacturing problems.
When he walked into interviews, he didn't say, "I can learn AI." He said, "I know exactly why manufacturing executives are skeptical of AI implementations, and here's how successful companies overcome those objections."
He positioned himself as someone who understood the buyer, not just the technology.
The Lesson: Companies think they want an AI sales experience, but what they need is someone who understands their buyers' real problems and objections around AI adoption. Your industry experience isn't a liability – it's the exact qualification they need but don't realize they're looking for.
Strategy 2: Become the "Why AI Fails" Expert
The Reality: Stop trying to prove you can sell AI and start proving you understand why AI sales fail – and how to prevent it.
I had another candidate, Lisa, coming from pharmaceutical sales. Instead of highlighting her sales numbers, we completely repositioned her story around a different angle.
She researched why AI implementations fail in healthcare – and trust me, they fail a lot.
She discovered that 70% of healthcare AI projects never make it past the pilot phase. Not because the technology doesn't work, but because sales reps don't understand the regulatory concerns, budget approval processes, and change management challenges in healthcare organizations.
Lisa created a LinkedIn post titled "Why Healthcare AI Sales Reps Are Losing Deals (And How to Fix It)" that got 50,000 views. She wasn't selling herself as an AI expert – she was positioning herself as someone who understood why AI sales fail in her industry.
Three AI healthcare companies reached out to her that week.
The Lesson: Stop trying to be the person who knows AI inside and out. Become the person who knows why AI sales stall, why buyers hesitate, and how to navigate the real-world challenges of selling transformation, not just technology.
Strategy 3: The Backdoor Strategy
The Reality: Sometimes the best way into AI sales isn't through the front door.
This is probably my favorite success story. I placed a candidate into what was technically a "Senior Account Executive" role at a company that had both traditional enterprise software and AI products. During the interview process, they focused on her track record with their core software business.
But here's what happened six months later: She became their best AI salesperson.
Why? Because she understood the account relationships, she knew how to navigate the organization, and when clients started asking about AI capabilities, she was the trusted advisor they turned to.
Now she's leading their AI sales training program and making 40% more than when she started. She didn't break into AI sales – she evolved into it.
The Lesson: Look for companies that have both traditional and AI products. Get hired for what you know, then become indispensable in what they're building toward.
Your AI Sales Preparation Action Plan
Now you're probably wondering, "How do I prepare for these conversations?" Here's your roadmap:
To Understand AI Market Dynamics:
Read "Crossing the Chasm" by Geoffrey Moore – still the best book on selling transformative technology
Subscribe to "The AI Business Newsletter" by Emerj
Follow CB Insights' AI trend reports
To Research Your Industry + AI:
Google "[Your Industry] + AI case studies"
LinkedIn search: "AI transformation [your industry]"
Join industry-specific AI groups on LinkedIn
To Build Credibility Fast:
Write ONE thoughtful LinkedIn post about AI challenges in your industry
Comment intelligently on AI company posts
Share one AI industry article per week with your perspective
To Find the Right Opportunities:
Target companies that are 2-3 years into AI development (not brand new, not fully mature)
Look for hybrid roles that include both traditional and AI products
Research companies where your industry expertise is their target market
Remember, you're not trying to become an AI engineer. You're becoming a business professional who understands how AI creates value in your world.
The Real Opportunity in AI Sales
This bias against non-AI salespeople isn't going away overnight. But while everyone else is complaining about it or trying to fake their way through, you can be strategic about it.
The companies that are going to win the AI race aren't the ones hiring AI sales clones – they're hiring diverse, experienced salespeople who bring real-world perspective to selling transformative technology.
Your years of experience navigating complex B2B sales cycles, understanding buyer psychology, and managing enterprise relationships? That's exactly what AI companies need, even if they don't realize it yet.
The key is positioning yourself not as someone trying to break into AI, but as someone who brings critical expertise that AI companies are missing.
What's Next for Your AI Sales Journey?
The sales job market is changing fast, and the window for transitioning into AI sales without direct AI experience won't stay open forever. As the industry matures, companies will start requiring specific AI sales track records.
But right now, in 2025, you have an opportunity to be part of the first wave of salespeople who help define what AI sales success looks like.
If you're ready to make this transition strategically, I've put together additional resources and strategies at MySalesRecruiter.co. You'll find detailed guides on positioning yourself for AI sales roles, optimizing your resume and LinkedIn for AI opportunities, and interview strategies that work in today's market.
What's been your experience with AI sales hiring? Have you faced the "no AI experience" rejection? Share your story in the comments below – your experience might help another salesperson navigate this challenging transition.
Looking for more sales career advice? Follow @mysalesrecruiter on YouTube for weekly insights on advancing your sales career in today's rapidly changing market.
