Reggie Marable: Inside Silicon Valley’s Fastest Growing Sales Machine & How to Prospect, Outbound and Close Enterprise Deals in AI

Reggie Marable is the Head of Global Sales at Sierra, a conversational AI platform for businesses. Sierra enables companies like ADT, Sonos, SiriusXM, and WeightWatchers to build AI agents that transform customer experiences. The company has rapidly become a hypergrowth leader in Silicon Valley, recently securing a funding round that values it at $4.5 billion. Before joining Sierra, Reggie was the Head of Sales in North America at Slack and the Area Vice President of Enterprise Sales at Salesforce.

In Today’s Episode We Discuss:

• What I Learned from Failing Early as a CRO

• The Most Effective Sales Strategy and the BS Sales Methodology

• How to Build Sales Processes from Scratch

• When and How to do Verticalised Sales Teams

• How to Become World Class at Sales Prospecting and Outbound

• How to Use Proof of Concepts to Win Enterprise Deals

• Enterprise vs. Self-Serve: Both or One and How

• Building a Sales Team from Scratch

• Structuring the Hiring Process

• How Founders F*** Up Hiring in Sales

• Handling Salary and Title Expectations

• How to Run Effective Deal Cycles

• How to do Onboarding for New Sales Hires

• How to do Post Mortems in Sales Processes

• Negotiating Enterprise Deals