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

This episode is brought to you by Capchase, helping software and hardware companies close deals while accessing TCV upfront. Learn more at capchase.com/20vc.

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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