Managing Pipelines

John McCracken, SVP Worldwide Sales at Castlight Health and Former SVP WW Sales Jive Software

John McCracken has been the SVP of World Wide Sales at Castlight Health since January 2015. He was formerly the Senior Vice President of Worldwide Sales at Jive Software, Inc. from November 2008 to September 2014. Mr. McCracken served as Senior Vice President of Sales at Inovis. John has an 18-year record of success across senior sales management roles for several leading technology firms. He held executive management positions at American Express, Warrantech and PC ServiceSource. He served as an Advisory Board Member for iConclude.

Summary Notes on Managing Pipelines

How do you properly distribute leads to the team?

• Get in touch with the potential customer as fast as possible
• Every lead has to be touched within 24 hours

Check monthly that the lead distribution across territories is even

• If uneven, think about how to move some leads over to regions that need more leads quarterly
• DO NOT fall into the startup trap of only distributing high quality leads to top performing deal closers as that will reduce your ability to scale across the organization

What are key metrics to manage and monitor a pipeline quarterly?

• Need to have at least have 3-3.5x of what is needed in a quarter in the pipeline
• Focus on the BANT opportunities with Budget, Authority, Need, Timeline
• Need to scrub constantly throughout quarter to make sure proper leads are sticking around and getting rid of bad leads
• Watch the adds and drops on a weekly basis; if adds are high with no drops, then need to clean out the garbage and contact regional VPs to make sure pipelines are properly flushed

When do deals typically get done throughout a quarter?
Enterprise:

• 20% Month 1, 30% Month 2, 50% Month 3
  Middle Market:
• If going after a SMB, should have a more even ramp
• 25% Month 1, 35% Month 2, 40% Month 3

Do not leave 80% in the back of the quarter

• Set incentives for employees to make sure they are closing in earlier months as well

What are some tips for land and expand strategy?

• Need to work on team structure and consider having an inside team to focus on the expand piece