As a founder or sales leader, you need to win faster, win more, and win bigger in 2019, and it all begins with landing better.

Answer these 5 questions to spot issues holding your reps back from landing new enterprise logos.

#1. Are your reps investing time in deals you can’t or shouldn’t win? If you know where your solution has high impact, and have the >75% win rate to prove it, add those scenarios to your ICP so that outbound SDRs aren’t wasting time on companies that don’t fit. These high impact, winning scenarios can also be added to your sales qualified lead (SQL) definition for inbound qualification.

#2. Are reps failing to create and maintain momentum during discovery? Your star sellers may be skillful active listeners. But most reps will better engage and motivate buyers when they’ve learned the real life stories behind the bullets in an ICP, and are enabled with a good set of discovery questions based on pain points and the hard and soft costs that justify the use of funds.

#3. Are reps unable to anticipate the perspective and concerns of the personas in your deals, and how each would benefit from your offering? I often find our clients’ buyer personas are too loose and intuition-driven to really help reps. For one vendor of an application development framework, almost all buying groups include an Enterprise Architect. But this vendor needs two EA personas, since some EAs come from an Infrastructure team, and some from an Application team, and this affects how they perceive and would benefit from the technology.

#4. Does your sales process conflict with your ICP’s preferred buying process? Here’s a simple, but still harmful example. When landing new customers, try-before-you-buy is really important to end user and technical personas, yet I still find vendors of on-premises enterprise software delay and put logistics in the way by requiring a SE’s site visit. Reps with tenure will have learned to adapt, while new hires who lack this tribal knowledge will underperform.

#5. Are prolonged negotiations over pricing and packaging consuming extra hours of reps’ time and delaying close? While your model may suit the originally targeted ICP, your pipeline probably includes buyers with unintended usage scenarios. In one case, roughly half the inbound opportunities we analyzed came from buyers who may be better served by inside sales reps in a transactional model rather than field sales, because they have an immediate need for just one component of the full offering.


The more you answered “yes” to these 5 questions, the more effort you and your reps will exert to close each new customer. The good news is you already know the people to guide you in fixing these problems. Your buyers aren’t hard to find, and they’re happy to help. Just ask.

If you’re a DIYer, you’ll find tips and shortcuts in my 24 Ways to Ace Your Win/Loss Analysis. Or get in touch with us if you want help.