(888) 815-0802Sign In
revenue - Home page(888) 815-0802

Sales Enablement in a Culture of Trust and Learning, with David Sill [Episode 710]

David Sill, Speaker, Coach, B2B Inside Sales Authority, and Head of Sales Enablement at DiscoverOrg.com, joins me on this episode.


  • Reps need to seek learning and invest in themselves in order to continue their development. A culture of trust is necessary for reps to try new things and possibly fail. David tells how he learned to trust in an improv class.
  • Sales organizations benefit from a culture of trust. But the expectations that are set and the tools that are used value conformity and compliance rather than trusting reps to take risks.
  • If you’re not leaving your comfort zone every single day, you’re not growing. Some sales technology squashes the willingness to take risks. How can you reach beyond the cadence to improve the ratio of activities to outcomes?
  • David explains how the leadership at DiscoverOrg.com shows vulnerability by going first. Andy would like to see more latitude in the sales process. David categorizes tiers of leads.
  • Culture starts at the top. The early cadre of sellers at DiscoverOrg — still the leaders today — built a culture of trust and learning. It takes having the right people on the team, willing to teach and show the way.
  • Values and character are essential. David talks about interviewing candidates about failures and challenges.
  • Most failures are failures in communication. Sales reps are better at explaining than listening. Managers are better at warning than coaching. Build a culture where you can call each other out on issues.
  • Development is a responsibility between the individual and the organization. It takes individual investment. People need encouragement to be motivated. To practice is the sine qua non of finding the next level.
  • DiscoverOrg adds tools to their team’s sales stack to develop enablement behaviors they want to encourage that will make more money and help the company grow faster.
  • DiscoverOrg has a process to map a rep’s career trajectory and possibilities. For sellers, that involves “buckets of learning.” DiscoverOrg uses content and training to fill these buckets.
  • Parallel to a career path is an achievement path. Teach skills before demanding of people to use those skills. Teach new managers on how to coach. Train the trainers.
  • Andy shares a mantra: Manage the process. Coach the opportunities. Mentor the people. David encourages taking learning and reflection time. Mentoring is about leading people to discover and use solutions to their needs.