2 Steps to hiring great salespeople

You're looking for a perfect resume. Stop. That's a costly mistake. Your first salesperson doesn't need a huge rolodex. They need empathy—an obsessive desire to solve your customer's problems. You can teach your product. You can't teach them to care. Look for the person who asks about the customer’s pain, not their own commission. Today, do this: Write one interview question that reveals empathy, not experience. For example: "Tell me about a time you truly understood a customer's problem." Hire for character, train for skill. The journey from a successful founder-led sales effort to building a scalable sales team is where most startups hit a wall. You've closed the first few deals yourself, successfully navigating the early market and validating the product, but now you need to step back. The instinct is to hunt for a "perfect" resume, someone who can immediately take the reins and start closing big deals. This pursuit of the "experienced" hire is often a costly mistake that leaves the founder burned out, and the new hire floundering. The fundamental issue is that a highly experienced seller requires a defined, replicable sales environment, something that is often still being figured out after founder-led sales. Your first sales hire needs to be a detective, a product-market fit explorer, and a partner, not a mercenary. That's why they need to embody two non-negotiable traits: great listening skills and deep empathy. Empathy, in this context, is an obsessive desire to genuinely solve your customer's underlying problems. It is the same client-centric spirit that fueled your initial founder-led sales success. You can teach product knowledge, pitch mechanics, and CRM hygiene, but you cannot teach someone to genuinely care about the client's pain or to listen intently enough to uncover it. If your company needs help defining its path to scale and wants to move beyond the founder's initial success, consider engaging a fractional sales leader. This strategic approach allows you to systematically build a scalable, repeatable sales process and provide the critical coaching framework your first hires need to succeed. By hiring for character—specifically, the capacity for listening and empathy—you bring in raw, high-potential talent eager to learn your specific business. Then, you train for skill. Don't waste time looking for a fully-formed sales machine; look for the person who cares enough to become one. The difference between hiring a good resume and hiring great character is the difference between slow, expensive growth and genuine, sustainable scale. Key Takeaways 1. Adopt a "Character First" Hiring Philosophy The most valuable lesson is to fundamentally change your approach to hiring your first salesperson. Instead of searching for candidates with a perfect resume or an extensive client list, your focus should be on two innate character traits. The core philosophy is: hire for character, train for skill. 2. The Two Non-Negotiable Traits Are Empathy and Listening A truly great salesperson must possess two critical, untrainable qualities: Great Listening Skills: The ability to absorb and understand a client's needs. Empathy: Defined as an obsessive desire to solve your customer's problems, which is the internal motivation needed to drive long-term, ethical sales success. 3. Test for Character with a Simple Interview Tactic To ensure a candidate has these qualities, use a straightforward two-part test during the interview process. Ask your most important question (the one designed to reveal empathy) first. Then, at the very end of the interview, ask the candidate to recall what that first question was. This technique quickly and effectively reveals whether they were truly focused and listening during the conversation. Frequently Asked Questions: 1. What is the core philosophy you recommend for hiring a salesperson? The core philosophy is to "hire for character, train for skill." You should focus your evaluation on a candidate's inherent qualities, such as empathy, over their pre-existing sales experience. 2. What are the two most crucial qualities a first salesperson must have? The two essential qualities are great listening skills and empathy. The video argues these are non-negotiable character traits that cannot be taught. 3. How does the video define "empathy" in a sales context? Empathy is defined as an "obsessive desire to solve your customer's problems." This motivation ensures the salesperson is focused on the client's needs rather than just closing a deal. 4. What is the costly mistake you warn against in the opening? The mistake is looking for a "perfect resume" or a salesperson with a huge rolodex. The video explains this is a common, but ultimately costly, misjudgment when hiring your first salesperson. 5. What is the two-part interview tactic suggested for testing a candidate’s character? The tactic is to write one interview question that reveals empathy, and ask it first. Then, at the very end of the interview, ask the candidate to recall what your first question was. This reveals their focus and listening ability.