Win with a Disciplined Sales Process. With Bridget Gleason. And special guest, Phill Keene [Episode 598]

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Bridget Gleason is VP of Sales for and my regular partner on Front Line Fridays. We’re joined on this episode by Phill Keene, Director of Sales at Costello.


  • Bridget and Andy discuss travel and weather, as Bridget is just back from Tel Aviv.
  • Phill Keene, Director of Sales at Costello is the special guest. Costello helps align front-line reps, managers, VPs, and CROs about pipeline deals to identify gaps and remove roadblocks in a three-part solution.
  • Phill explains the parts of the solution. One aspect proactively simulates a pipeline review to visualize what steps are needed for deals.
  • The Costello solution works with reps on calls, capturing notes and information, and guiding a rep through a conversation to find the path to a signature.
  • Phill describes how Costello saw that reps were using only the required fields in Salesforce but they were recording copious data on paper or stand-alone apps that never made it into a CRM. Costello addresses that issue.
  • The next aspect is to look at competitor statistics, the number of problems to solve and other data points to visualize gaps in the pipeline and how to fill them.
  • Ideal customers for Costello are companies already on Salesforce, with more than 15 and up to 200 reps, following a documented sales process, and having a VP of Sales who is motivated to enforce it.
  • 50% of SaaS reps hit quota, casting doubt on the efficacy of methodologies. Phill asserts that top performers follow a process. Andy says that top performers have their own process that is not often the general company process.
  • Phill uses examples of Costello customers improving their conversions by leaps and bounds when uniformly following a methodology.
  • People buy from people. Building a rapport precedes methodology. Principles come before methods. Methods must be built on engagement and the basic principles of sales. Phill dives into Costello guidance to the process.
  • It requires hiring for sales ability and investing in training and development; reps will feel purpose and they will want to stay and excel. The primary reason for sales rep turnover is the manager.
  • The inside sales model has a low close rate compared to other industries and market segments. Andy suggests rethinking every position, especially SDRs.