Key Takeaways
- Max Freeman looks for sales reps at companies with north of nine figures in revenue that suffer from low Net Promoter Scores.
- Sellers who rank in the top two at low-NPS companies have learned to win against product headwinds, making them lethal when paired with strong software.
- Ramp targeted former investment bankers to sell to CFOs because they understand finance, bring high analytical horsepower, and treat eighty-hour weeks as normal.
- Freeman pays Sales Development Representatives double the market compensation rate while requiring four to six times the output: 40 to 60 booked meetings.
- Ramp scales go-to-market efficiency by treating sales as an engineering problem, driving quota-to-compensation productivity ratios between 7:1 and 12:1.
The Mispriced Asset in Sales Hiring
Most software companies run the same recruiting playbook. They search LinkedIn for account executives who spent three years at a high-flying SaaS company, pay market rate, and hand them an ordinary quota.
Max Freeman did the opposite at Ramp. He treated sales recruiting like Billy Beane assembling the Oakland Athletics. Instead of paying top dollar for obvious résumés, Freeman hunted for two mispriced talent pools: junior investment bankers and reps selling hated software.
Early on, Ramp staffed its go-to-market team with former investment banking analysts. On paper, they lacked traditional SaaS closing experience. In practice, they held two massive advantages when selling finance software to CFOs.
“One, bankers are programmed to work. The concept of a nine-to-five is completely foreign to these folks,” Freeman noted. “Two, they have intelligence and they have business acumen and a lot of horsepower that is not always found when hiring for sales talent.”
A 24-year-old banker can open a three-statement financial model, speak the buyer's language without stumbling, and maintain credibility with an executive team. They also view a sixty-hour tech workweek as a light schedule. Several of those early banker hires now run large divisions of Ramp.
Hunting for Sellers at Low-NPS Giants
Freeman's second talent pool targets enterprise software companies that scale despite their product.
“I am a huge fan of Moneyball and you have to treat go to market recruiting like Billy Beane,” Freeman explained. “There is so much alpha in finding what companies have grown revenue... north of nine figures, but have done that despite having a low NPS score.”
When a company hits $100 million or more in revenue with terrible customer satisfaction, customer momentum is not driving the pipeline. The sales team is dragging revenue across the line through sheer grit. Reps at those companies fight broken user experiences, churn risks, and angry buyers on every call.
Drop an average rep into a company with high product-market fit, and they look brilliant. Drop them into a company with low NPS, and they miss quota. When you extract top performers who hit quota despite bad software and hand them a product customers actually like, their output explodes.
Paying 2x for 4x Output
Ramp does not discount talent to save cash. Instead, Freeman pairs above-market compensation with aggressive quotas.
“We'll pay 2x what a standard SDR is going to make,” Freeman said. “But guess what? You got to book 40, 50, 60 meetings, which is four to six times what a standard SDR has to book.”
By treating sales design as an engineering system, Ramp engineers sales capacity to target productivity ratios between 7:1 and 12:1. Instead of managing ten reps who each schedule ten meetings a month, Ramp hires five top-tier operators, pays them above market, and automates administrative friction so they can book fifty meetings each. You get fewer communication silos, cleaner data, and higher output per seat.
What to Do With This
Audit your sales hiring pipeline this week. Make a list of three software companies in your industry with poor user reviews and over $100 million in ARR. Reach out to their top two account executives with a pitch focused on your product quality.